BE704636A - - Google Patents

Description

  

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  "Derivatives of fatty acid amides"

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 EMI2.1
 The present invention. relates to cholesterol lowering agents. More particulièremont. ello ooncor "! agents8 useful for lowering the high levels of chel '*: erol in read without.



  Atherosclerosis, which is a simple form of art6 #. 09 key ... intine roso, is an adult back disease for which no known satisfactory treatment is required. Although the water of the athôrooclvr0sc has not yet been known, nalGi6 the 'nbrou *' sos discussitn,. '"1 in academic circles, we generally admit: orJont that one of the u.:!l1jf'c3liE' .t: toJln histol1a.thologiqucB the most i 'J: 1rtan-tes do is the deposition of lipids in 10, anti, Consequently, ncQ, ruchorchoe have been consaor6iie in lAd' r JliSlIo parturbated with lipids ot one this upstart to atnuor la (ur extrtm - riuiit alov '.' c cholesterol in the blood.



  0.-. e tai; 1; ooe% to '. certain number of fact: 3 clinics 0; oxperimontals yes indicate the relation ontro the atherosclerca "and the tfi%: Ciw; lcv6o; 1.i. 'Jholcstr.! rol dN1l the blood. Therefore, the itino had poi: it of a; a, itn = pvrn.ettan 5 de will reduce the high level of cholestery of the sanp is Qrm0nt iportnnto for the prevention: ', oa of atherosclerosis.



  Don of efforts have been devoted until now to the nd3e at the point of llf '; 01 ".tS do oc tY1.?o in view of do = X41, iro the toncur on Cholesterol ot we tested aliniquo1il <.: nt a number of compounds, but none, of which no have been found to be completely satisfactory. Some are ass-, z efficacos, but they produce n-2Condair.is neàstis effects which are not negligible, while The others have inadequate efficacy, so they must be administered in high doses. A 3X'OUPQ of compounds * currently used in practice for the above purpose. Above coliprond dos unsaturated fatty acids, One in particular the linoldiquo aid.

   The reason for the aquollo aci-

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 of linoleic is used, residue in its harmless character vis-à-vis the human body. However, its effectiveness is not very high and ello is uncertain and poorly defined. Accordingly, large doses must be administered to obtain at least appreciable effectiveness as a cholesterol lowering agent.



   We have found a group of compounds effective as cholesterol lowering agents and which are substantially non-toxic.



   According to the present invention, there is provided an agent for reducing the tone of cholesterol and comprising an N-substituted fatty acid amide corresponding to the formula:
 EMI3.1
 in which R represents a synthetic or natural C13-C25 aliphatic chain, saturated or unsaturated, branched or straight comprising an OH group or not.

   As examples of RCO, there are the following fatty acid residues: in the case of saturated acids, myristic acid, palmitic acid, stearic acid, isostearic aoidos, araohidic acid, beheniquo acid , lignoceric acid, cerotic acid and montanic acid and, in the case of unsaturated acids, the residues of the following acids:

    tsuzuic acid, physetoleic acid, myristoleic acid, zoomaric acid, palmitoleic acid, petroselinic acid, oleic acid, elaidiquo acid, vacceniquo acid, l gadoleic acid, erucic acid, brassidic acid, selacholeic acid, linoleic acid, linolenic acid, eleostearic acid, ricinoleic acid, parinariquo acid, arachidoniquo acid, eicosatetraenoic acid,

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 eicosapontaenoic acid, dooosapentaenoic acid, hempseed oil fatty acid,

     linseed oil fatty acid, Petilla oil fatty acid, styrax oil fatty acid, oiticica oil fatty acid, oil of oil fatty acid kaya, oil fatty acid from walnut oil, fatty acid from poppy oil, fatty acid from oil from carthamo, fatty acid from watermelon oil, fatty acid from oil d3 soybean, sunflower oil fatty acid, rice bran oil fatty acid, citro-trouillo oil fatty acid, kaoliang oil fatty acid, fatty acid of sesame oil, fatty acid of corn oil, fatty acid of rapeseed oil, fatty acid of cottonseed oil, fatty acid of cliva oil, 'mahogany oil fatty acid,

     taubaki oil fatty acid, goldGot oil fatty acid, castor oil fatty acid, araobido oil fatty acid, fatty acid palm oil, palm kernel oil fatty acid, coconut oil fatty aoido, beef tallow fatty acid, lard fatty acid, coconut oil fatty acid bone, choval fat fatty acid, locust oil fatty acid, chrysalis oil fatty acid, shark liver oil fatty acid, fatty acid soybean oil, fatty acid from sardine oil, fatty acid from caranEua oil, fatty acid from mackerel oil, fatty acid from scombrésoce oil,

     barons oil fatty acid, Saurel oil fatty acid, Moruo liver oil fatty acid, Trout oil fatty acid, Saurel oil fatty acid mulot, oil fatty acid from tuna, fatty acid from menhaden oil (monuko), fatty acid from menhaden oil, fatty acid from plouronocto oil, fatty acid from eel oil, different types of fatty acids from baloino oil, fatty acids from body oil, fatty acids from skin oil, fatty acids from oil from head, fatty acids of liver oil, fatty acids of residual oil and acids Arm of egg oil, as well as

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 oils analogous to plants,

   land animals or marine animals. In addition, their stereoisomers or double bond positional isomers can also be employed,
Among the above acids, one can optionally remove the saturated fatty acid from natural fatty acids approximately by a suitable method, for example a cooling method, a urea method, a rooristallization method, a cold method. with metal salts, a distillation method and the like.



   In addition, in the above formula, R 'is a group d- or
 EMI5.1
 / -01-lower aloly-bonzyl. a d- or 1-c-substituted racemic interior aleoyl-benzylo group having substituents on the benzene ring, for example a lower alkyl group, a halogen atom, a lower alkoxy group or a nitro group,
 EMI5.2
 a racemic d- or 4P-O (-bonzyl-bonzyl group or an adamantyl group, R "represents a hydrogen atom or R 'and R" represent an oyclohexyl group and, in the case where ROO represents a isostearoyl group, R 'represents, in addition to the radicals ci-
 EMI5.3
 above, an alkyl, alkenylo, ayoeloaloeoylo, alcoyi-oyolo- alocylot hydroxyayoloa3.aoylo, alooxy-oyoloalooyl, aleoyl- aryl, hydroxy-aryl et alkoxy-aryle, halo-ary1ge halo-alooy1-any,

   halo6eno-alooyl-haloz6no-arylo, alkoxy-halog4no- arylo, uralcoylc, a3coy3. aralkyl, hydroxy-aralotylot alkoxy- avaleoyl or xao..alooyl inféniour-Rralooylo and nu pr68Qnto an atomo dllvdrogèno, one or the other due BV (MDGB represents Ruz or a heterocyolic group (comprising 7 atomow of carbon or less) constituted by NR'R "containing an atom of oxysene or not.



   The starting amines are the d isomers. or #optics of
 EMI5.4
 c-alcoyl inférieurbnnzy3.an.nos as the d ... au, mt? ayl-

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 EMI6.1
 bontylminet d- or ..- ethy.-bvnzy.ar.nv, d .. or 1 .. 0 (propyl- (ii.- or 1 -) .. bcnzylumino and d- or -t butyl (n, "4- - C'1 t -) - 'or.s..x.ir.c, as well as dos d- or ... rac6mic aminos folios quo Ion derived from -alkyl izE'r. vux..bo.z91am3.nos substitas slab IV. .1? t:) n.tio 0 (by a lower alkyl group tal than a group ml t ':

  . ()! ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl ot also having, in the phenyl radical, radicals those tols that one or more members selected from the halogen atoms, for example example of fluorine .. chloro, bromine ot iodine, lower alkyl groups as much as methyl groups
 EMI6.2
 ethyl, r.-pop9lo, 1-propyl, n-butylo, i-butylo ot t-butylo, lower alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy, as well as the radical NO2.



   These active optically active aminos can be readily resolved by the method described, for example, in "Journal of tho
 EMI6.3
 ChoIi1ica.J. Education ", Vol. 42, page 296, from raoé-miquos aminos synthesized according to the method described for example,
 EMI6.4
 in "Bulletin of the Chemical Societies of Belgium" # Vol. 72s pages 195-407. Do more, the d- at 1 ..; 'b (JnYl The racy bonzylwn1no8 can be easily resolved according to the method described in "J. P3; 'acltt (hou.",' 2,7, t 19.!, 237 (1921).



  In addition, dicyolohoxYlamino $ ot dos adamantylamines can also be used.



  In 10 these dos 3.sostéaroy.am, das, in addition to amines. mono- or dialkylamino acids such as mono- or dimethylamino, mono- or diethylamino, mono- or di-n-propylamine, mono- or di-i-propylamine, mono- or di-i-propylamine,
 EMI6.5
 mono- or d ..- nbutylsn.inc! mono- or di-1-butylanine, nono- or di-t-butylamine, mono- or d1-dodecylinu,

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 mono.

   or di-palmitylamine, mono- or distearylamine and the like, as well as mono- or di-alkenylamines tollos such as mono- or diacrylamine, mono- or diarylamine, mono- or dicrotonylamine, mono - or dioleylamino, mono. or dilinoleylamine, mono- or dilinolenylamino and the like, cycloalkylamines such as mono- or dicy-clopentylamino, cyclohoxylamino and mono- or dicyclohop- tylamino, as well as said cycloalkylaminos substituted by one or more members selected from among the lower alkyl groups such as methyl, ethyl, n-propyl, i-propylo, n-butylo,

     1-butyl and t-butyl, hydroxyl groups, lower alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy, as well as methyl groups, ethyl, n-propyl, i-propyl, n-butyl, i-butyl ot t-butylo N-substituted aromatic amines such as diphenylamines or aniline substituted by one or more mombros comprising hydroxyl groups , alkyl groups tols quo methyl, ethylo, n-propyl, i-propyl, n-butylo, i-butylo and t-butylo, halogen atoms tols quo chloro, fluorine, do bromo and ioda, CF3,

   as well as alkoxy groupos such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy or t-butoxy, anilinos substituted by lower alkyl groups such as N-methyl, N-ethyl , Nn-propylot Ni-propyl, Nn-butylo, Ni-butylo and Nt-butylo, substituted arylaminoes comprising N-lower alkyl-anilinos substituted by the above-mentioned substituents, heterocyclic aminos such as pyrrole, pyrrolidino, morpholine , piperidino ot hexamethylene-imino, dos aminos tollos quo bonzylamine ot di-benzylamino or said amines substituted by one or more members comprising hydroxyl groups,

     dos lower alkyl groups such as methyl, ethylo, n-propyl, i-propyl,

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   n-butylo, i-butyl ot t-butylo, alooxy groups such as
 EMI8.1
 metho.-cy # 6thoxy, n-propoxy, i-propoxy, n-butoxy, i-buto: ut t-butoxy, dos alooylos groups i.n5r.ouxa aubetitu6s tole quo groups -methyl, 0 (-ethyl, 0 (-n-propyla, e Racemic -i-propylo (-n-butylo. Q / -1-bUtyl and o (-t-butylo), so that 'N ... substituted lower alkyl groups such as N-methylo, 11-ethylo groups , Nn-propylut Ni-propylo, 11-n-butyl # Ni-butyl and Ht-butyl.
 EMI8.2
 



  In the present invention, isogtGacicuos acids are stearic ao1d08 having side chains, eg, 3-, 4-, 5- to 16-nethyl hoptadecanotquos acids. However, these acids and the other acids have C18 comprising back cat-
 EMI8.3
 noa lateralon must ttro included in the present invention.



  These substances are free from double bonds and, therefore, ollos have the advantage of being rolativompnt not sus- coptiblos to oxidation.



   For the preparation of the N-substituted acid araidos of the present invention, any known method of preparation for the preparation of the acid amide can be accomplished.
 EMI8.4
 



  By oxomplo, (1) a fatty acid of formula 11000H is reacted directly with uno amino of formula MT, it is assumed that there is no dehydrating agent that a compound of
 EMI8.5
 disubstituted carbodiiliidu, p-tolubn-suiPon3cuo aoido or p-tolunv-aul.on3rlo chloride or the like in an aqueous or organic solvent, (2) a fatty acid of formula RCOOH is converted to a halide of acido do fornulo .m0X, where X represents a halogen atom ("organizes Synthoaiz", Vol.

   57, page 56), then we word the acid chloride obtained on contact with
 EMI8.6
 / R 'to Hoina an equimolar amount of 1' aquino of formula EIT "- n, t R the presence of a basic condensing agent, (3) is made

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 EMI9.1
 react directly a lower alooyl ester or a glyceride of an acid Uras of formula 000011 with the amine of formula HlK / lll
 EMI9.2
 we preaoncQ or absence of a solvent ot an al3Out of condensing.
 EMI9.3
 
 EMI9.4
 in which R "'represents an alouylo or haloalkoylo radical of 1 to 4 carbon atoms, avoo the amino of formula HN, R" is the presence of a baniquo condensation calayer;

     in the pro-
 EMI9.5
 Given (1) to (4) above, R, Ft 'ot R8 have the same meanings as those indicated above. The methods (1) to (4) are described below in more detail.



   (1) (a) We have already described several searches in losquol-
 EMI9.6
 los dioyclohexylcarbodiimido was used in the synthesis of a polypoptide. However, we have never mentioned the synthesis of an anide using a higher fatty acid for pre-
 EMI9.7
 Therefore, the method of the present invention is important.

   In particular, it can be said that the process of the present invention is very advantageous in that the desired product is easily isolated by filtration and separation of the precipitated urea when the reaction is completed, without any special operation and being. given that said urea can be used again after having been regenerated by a treatment such as dehydration.



   For the disubstituted carbodiinide to be employed in the present invention, there may be mentioned, for example, dicyclohoxyl-.
 EMI9.8
 carbodiimidop diisopropyl-carbod11m1do, d1phenyl-carbodiimide ot n * importo quol autro dialooyl-carbodi1mido, dioyclcnlcoyl-

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 diaubstituted carbodiimide or phenyl-carbodiimido.

   Either of them is also useful. In the process of the present invention, when carrying out this process, a fatty acid, an amine corrosive to a disubstituted carbodiimide, for example, is separately dissolved in a.

   organic solvent such as an organic solvent for an aromatic hydrocarbon tol quo benzene or toluene, a hydrocarbon solvent such as n-hoxano, a cycloalkane, petroleum ether or gasoline, an ether solvent you quo diexane, ethor or tetrahydrofuran or an alkyl halide solvent such as chloroform, ethylene dichloride or carbon tetrachloride or else an aster solvent such as acetate do methyl, ethyl, propyl or butyl, These solutions are immediately mixed at room temperature or with cooling in the case of a significant release of heat, so as to obtain approximately 1 in the molar ratio,

   then the mixture is stirred according to the required conditions and left to pour out at room temperature for about 3 to 24 hours, after which the corresponding urea, which is a by-product of the reaction, precipitates. After removing the precipitates by filtration, the desired product can be obtained from the filtrate. In addition, the disubstituted carbodiimide in excess can be decomposed with acetic acid or the like under appropriate conditions.



   The urea recovered is dehydrated and the carbodiimido obtained can be used again for the main reaction (b) The aforementioned amino and fatty acid is dissolved in an appropriate solvent tol quo lo bonzene, toluene, xylene, chloroform or carbon tetrachloride and the like.

   To the solution is added sulfuric acid. do phenol-

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 sulfonic acid, p-tolueno-sulfonic acid, chloride of p-
 EMI11.1
 tolueno-sulfonyl or an acidic or basic ion exchange resin, by oxonpy 1 "'IRA. 400", 1 "' IR-50", or IIIR-12011 or read "Amberlito 15, 21, 26 or 27 "as a dehydrating agent. Then, the solution is heated using a water separator to separate and remove the water formed. The solvent is then removed and the product formed is purified, so as to obtain
 EMI11.2
 a deeir6 product with a high rundonent ot in a simple way.



  Alternatively, the desired object of the presonto invontion process can be sufficiently achieved by simply heating the solution in the presence of a dehydrating agent) employing, as a solvent, an organic tertiary amine tollo and pyridyl.
 EMI11.3
 no, picoli.ao or lutid3, nc, a plus of the aforementioned solvent.



  (c) Thermal dehydration process <We heat the arrl.nu and the aoidu the aforementioned fat to about 130-3000G laying a pericdo c01Jlr.sù between a few hours and a few tens of hours, evuntuollenent we p 6sonco of an acid catalyst such as that boric acid, to obtain a desired product. In this case, the forced water can be removed from the reaction system or the reaction can be carried out in an autoclave, in order to maintain the temperature above.



   (2) The condensation reaction of an organic amine with an acid halide is also known. However, to the best of the knowledge of the Applicant, no mention is made of the preparation of anti-atherosclerosis agents using this method. The Applicant has found that by adopting the method, it is possible to obtain an amide derivative useful as an anti-atherosclerosis agent with a favorable roundness, under moderate non-oxidizing conditions.



   The object of the invention can also be achieved when an excess of a basic condensing agent is used.

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 such as an oustic alkali, for example potash or lithium caustic soda, an alkaline-torrous hydroxide tolerated by calcium or barium hydroxide, an alkali carbonate tolerated by lithium, sodium or potassium carbonate, an alkaline-torroux carbonato tol quo carbonato do ealoium or do barium, uno amine tortiairo such as trimethylamine, triethylamino, dimethyl-aniline, pyridino, pioolino,

     an anion exchange resin or an excess of the starting amine or either of the aforementioned aminos.



   In this reaction, as a solvent, we use oau, uno
 EMI12.1
 organic keton tol1o quo acetono, mfth11.ethyl-aeton or m4thyl-isobutyl-retono, ostor tol quo methylo acetato, othylu aootato, propylo acetate or butylet aQ6tate or uncoro ethyl ether, propyl ether, tetrahydrofuran or dioxane, a hydroarbon solvent tol that n-
 EMI12.2
 hox = o, lu o7clohoxanue benzene or toluene, an aloyio halide such as ethylene diohloride, chloroform or carbon tetrachloride, a tortiairo amine such as dimethylformamide,

   pyridine or piaolino or oncoro either starting amino acid alone or in a suitable mixture.



   For the reaction, any low temperature ranging from the freezing point to a point near the boiling point of the solvent can be employed. Additionally, it is desirable to carry out the reaction in a stream of an inert gas such as azoto or helium.



   (3) (a) Process in which glycerides are used:
We mix the above-mentioned oil glyceride and an equimolar amount of uno amine avocado a basic catalyst such as sodium methylate, sodium ethylate, potassium butylate.
 EMI12.3
 sium, potassium hydroxide or sodium hydroxide ot ana-

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 logues, or alternatively with an acido tol quo catalyst ammonium chloride or boric acid and the like,

   then the mixture is heated to about 50 - 300 ° C. for a period of between 30 minutes and a few tens of hours, in order to obtain a desired product. Even in the absence of the basic or alkaline catalyst, the desired product can be obtained with favorable roundness when the amine is used in excess. In this case, the desired object can be achieved in the presence or absence of an inert organic solvent.



   (b) Process in which esters are used:
An ostor of the aforementioned fatty acid or of a mixture of fatty acids obtained from the aforementioned fats or oils is mixed with uno amino, then the mixture is heated to about 100 - 300 C for a period of time. between 30 minutes and a few tens of hours, the aforementioned basic or acid catalyst and an inert organic solvent are present or absent, so as to be able to achieve the object of the process of the present invention. In this case, an alcohol formed can be removed from the reaction system or an autoolavo can be employed.



   The reactions due to two processes (a) and (b) mentioned above must be carried out in an inert gas such as nitrogen, in order to prevent the formation of peroxides, coloring matter and by-products. inconvenient analogues.



   (4) The reaction of the mixed anhydride process, which is carried out at a low temperature, is practically completed at about 0 ° C. The unsaturated fatty acid derivatives. In particular, there are unstable substances which under certain conditions undergo oxidation, polymerization, positional or geometric isomerization and the like as a result of heat in air.

   Therefore, it has been found that the process for the preparation of starch derivatives of unsaturated fatty acids

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 In accordance with the present invention, which is a low temperature reaction, was of considerable importance to obtain excellent results.
 EMI14.1
 zanzi lof <solvents employed in the reaction of the present invention are ether, dioxane, tetrahydyofuran, dicM-crothano, chloroform, carbon tetrachloride, ethyl acetate, acetate. ethyl, lo benzene, toluene, xylene, acetone and methyl isobutyl ketone.

   As basic materials, tertiary amines soluble in organic solvents, such as
 EMI14.2
 trimethylamine. triethylamino, dinethyl-aniline, diethyl-anilino, pyridine and the like. However, in some cases inorganic bases such as potassium carbonate and sodium carbonate, or basic ion exchange resins can also be employed.



   In order to prepare this mixed anhydride, a lower alkyl ester of 4 carbon atoms of halo acid of 1 to 4 carbon atoms is reacted with a fatty acid of the formula RCOOH, in which R a los mtmos meanings than those indicated above. among the halo-lower alkyl esters are, for example, chloroformates and acetates.



   The chloroformiatos and acetates to be used are the
 EMI14.3
 chloroformate and methyl acetate binds chlorotorcate and ethyl acetate, as well as chloroformate and butyl acetate and the like.



     The efficacy of the compounds was tested using mice fed a specific diet enriched with cholesterol and bile acids. The tone or cholesterol of the mouse back blood was increased to 3 - 6 times the normal level. The amide compound was also mixed with the specific regimen in an amount of 0.2% and administered continuously orally for 8 to 12 days. Then the total content was evaluated

  <Desc / Clms Page number 15>

 
 EMI15.1
 for cholontero in animal blood serum. During testing, no adverse side effects such as prevention of body weight gain and others were observed.

   It is 4 no- +, yet the indicated compound is superior to linoleic acid. In addition, in the group to which linoleic acid was administered, some cases were sometimes observed ineffective as a result of the individual differences of the drugs. animals and the efficacy has varied
 EMI15.2
 dérablomont, mtmo in lu mt3mo individual animal. It should be emphasized, however, that these phenomena were by no means observed in the group to which aoido amide was administered.



   A further important effect of the composition of N-substituted acid starch according to the present invention is to prevent the deposition of cholesterol and fat in the liver, which is produced in animals fed a rich diet. esterol. The linoleamide compounds appear to improve the function of the reduced closed lipid metabolism of the liver. This efficiency is also favorable due to the fact that the lipid metabolism is mainly based on the function of the liver. During administration of nucleic acid, this efficacy has never been observed. The results are shown in Table 1.



   The extremely low toxicities of the acid amide compounds of the present invention are illustrated in Table 2 in which the acute toxicities of certain compounds of the present invention are listed in mice.

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  TABLE 1
 EMI16.1
 
 <tb> Cholesterol <SEP> Cholesterol
 <tb>
 <tb> Compound <SEP> of <SEP> serum <SEP> of <SEP> liver <SEP>
 <tb>
 <tb> blood <SEP> mg <SEP>% <SEP> ng / 100 <SEP> g
 <tb>
 
 EMI16.2
 ¯wmr..a ... W aH .... n ..., .. ¯.rra. "R..wwA.w..rrwrw..rw.rwH ...,. N .... rmrr.rs ... rrrr¯r, ...- wr ..... orr
 EMI16.3
 
 <tb> [I] <SEP> Witness, <SEP> (none <SEP> composed <SEP> added) <SEP> 546 <SEP> 3505
 <tb>
 <tb>
 <tb>
 <tb> Aoido <SEP> linoleic <SEP> 324 <SEP> 4585
 <tb>
 <tb>
 <tb>
 <tb>
 <tb> (+) <SEP> N - ([alpha] -methyl-bonzyl) -
 <tb>
 <tb>
 <tb> linoleanide <SEP> 267 <SEP> 764
 <tb>
 <tb>
 <tb>
 <tb> (+) <SEP> @
 <tb>
 <tb>
 <tb> cleamide <SEP> 288 <SEP> 797
 <tb>
 
 EMI16.4
 (+) H- (-methyl .. 'bonzyl) - linol6nanido 269 784 (+) isôstCaridbunzyl) z51 isostéaraL11do 251 761 C *) dcaacurtha.munzylara3.do of oil 2? Â of carthamu 273 790 (+) -methyl- b <.:

  soybean oil m! lylDJ1lido 280 805 (+) -methyl-bonzylDJ1lido oil
 EMI16.5
 
 <tb> do <SEP> lin <SEP> 291 <SEP> 796
 <tb>
 <tb> (+) <SEP> [alpha] -methyl-benzylamide <SEP> from oil
 <tb>
 <tb> from <SEP> liver <SEP> do <SEP> cod <SEP> 251 <SEP> 743
 <tb>
 
 EMI16.6
 ('-) a (thyl-.bunzylrua.do of oil
 EMI16.7
 
 <tb> (the <SEP> cuttlefish <SEP> 248 <SEP> 748
 <tb>
 <tb> (+) <SEP> [alpha] -propyl-benzylamide <SEP> from oil
 <tb>
 <tb> da <SEP> cotton <SEP> 262 <SEP> 800
 <tb>
 <tb>
 <tb>
 <tb>
 <tb> [II] <SEP> Witness <SEP> (none <SEP> composed <SEP> added) <SEP> 521 <SEP> 3308
 <tb>
 <tb>
 <tb> Acid <SEP> linoleic <SEP> 329 <SEP> 4491
 <tb>
 
 EMI16.8
 e-) '(o mdthyl-bnzyl) -. 3inoJ.carn.do 286 908
 EMI16.9
 
 <tb> (-) <SEP> " <SEP> -cleamid <SEP> 283 <SEP> 808
 <tb>
 
 EMI16.10
 (-) "-linol6nam:

  Ldo 253 7G7 (-) "..isost6axamido 246 777 (-) (o {-6thyl-bunzy1) -lino1ôam.ido 251 S21
 EMI16.11
 
 <tb> (-) [alpha] -methyl-benzylamide <SEP> from oil
 <tb>
 <tb>
 <tb>
 <tb>
 <tb>
 <tb> from <SEP> safflower <SEP> 276 <SEP> 898
 <tb>
 

  <Desc / Clms Page number 17>

 
 EMI17.1
 (..) 0 (-methyl- banzylam1do of soya oil 271E 799 (-) 0 (..methyl-bonzylcunid0 of linseed oil 290 ?? 6 (- ethyl.-bcnzylam.do of sardine oil 261 ? 44> (-) 4 (- métl-bonzylt.i, do moruo liver oil 250 ma c? $ 3CO1HCH- 290 "5 CH3 01? H; S; sCONHrHO 295 13; S0 3 013? COI # yH-o 302 1620 CH; Ol; S1L? CONHfH-Q 2s2 1020 CH;

   C15I! ;; 1 CONHH-Q 30o 906 CH C15H: .sl CONHrHO 314 1160 CH3 1 'lH "l ONHf HO 2? 4 992 C2H5 a.?H3COrrx çx! I v;: 502 1042 C zH-

  <Desc / Clms Page number 18>

 
 EMI18.1
 Huila do arrthiuno-CONH! H 290 992 C3 Huila do 30.C7C-COßÎHOH 277 960 C4 IIIJ Control (none, compound added) 471 3130 017HlCOlnI9HCl 225 9 X5 Cl 171 CONH1H Cl 315 856 Chez Ol? H31COlTHTH-o- 385 1511 CH, 017H; lCONHCHO Br 322 1341 Ho. A17x; ia0xilH ± MOx, 242 1065 C2H5 C7H31c orrtçH.- .. cH3 237 1047 axj t: .. J.



  Control (no compound added) 595 3145 el? H, 100119H-Q-CI !:; 2'1-0 828 5 n

  <Desc / Clms Page number 19>

 
 EMI19.1
 017 H3, CONHC CH: 321 908 C2H5 C17II71 C # r.dCH-4,> - Cl 217 826 OUF (ô ci <{) r (25Z 1000 I 251 1000 CE: f (ci 1731 ') µ? 3 1? C17% 1 CONHßH -. -OOB; 234 1007 At CH; CH 1 isc-Cl? HSCOIIHCH -; - CH3 297 905 c2H5 CI-13 o179COlm? Ho 222 913 CH5 CH; 1 HuilQ do carthamo-CONHOH 1 -.Q 216 1003 C2H5 3 CE3 Oil do soicho-OONHO 1 -HD 232 922 CH3 IV] Control (no compound added) 372 2640 Aoido linoleic 351 312l OlIi29CONH-CH 238 729 CH2

  <Desc / Clms Page number 20>

 
 EMI20.1
 at 1? g 31 oo Il 214 544 du "200 500 2. Il 208 623 C17HCO-? Ho 245 831 OH2 j d-" 222 729 t "263 ses iso-Ci7ü35C0" 221 609 d- 209 561 1 ..... 252 639 Oil do carthmao-00 "220 575 d- u 204 515.

   Il 253 632 Oil of linseed-c0 "249 800 Oil of soiche-CO" 223 631 Oil of foio do of roquin-CO "248 621 Oil of sardinv-CO Il 231 607 IJ Control (no compounds added) 508 3270 Linoleic acid 314 4550

  <Desc / Clms Page number 21>

 
 EMI21.1
 Lino16amido 260 784 Linoiônamido 261 1071 Isoatéaranido 266 821 Amido of oil do ./\-/ carthrono RC0h 2? 8 1081 Auido d'huHo do faithodomoruo 249 920 Anido d'huila de soicho 258 830 Amido d'huilo do sardino 269 1005 [ Vil] Control (no compound added) 508. 3535 Linoleic acid 341 4550 ieostéaroYl-NH-o 2? 8 1081 1sostôaroy1-N <8,201 1053 isosted ArOY1-1; nTH g65 1061 CH; isostea.OY1-lm? Ho- on; 232,868 CH3 isost6aroyl-NHOHV;

   290 1100 isostearOY1-lijfOCH3 300 1090

  <Desc / Clms Page number 22>

 
 EMI22.1
 Control (no compounds6 added) 472 2652 N02 1? Hl COlf.dCUO 299 .1003 H /; - 1 2 1? Hl) l c # mH'Ü 28? 992 CH 1 2 H "1 CONliCHO 2 340 1603 H3" = T '1 2 H31 COlmcH. O NO2 31980 2331 c2U5 1-01? H5colmβH - () - NO2 294 a2. cH - "3 i-Cl? H5001fHrHN02 62 1305 Ï-ol? H35 coiiec N02 rice62 1305 OF.3 NO 1? 9COlmrH-U oo 1091 c2Ho5 N02 1? II33COlTHrH-Q 309 1113 \ = Gold N02 H \ dl0 due to safflower- CONFICH 312 982 1 CH, Huilo do soiche-001rHCH 1 - -C N02.;. 100 1502 1 \ =:

  = / CH3 (1

  <Desc / Clms Page number 23>

 
 EMI23.1
 Oil No2 Huilo do foie. do moruo-CONHfHV z 1403 en, [j1µ Control (no compound added) 336 2200 C1731CO1Ji-f'4 288 721 C17H, COlm 294 1120 CwXa9C010El 279 750 iso 1? H, 5COUU. @ 280 761 Oil do oarthtme-001 \ THD 292 745 Oil do lin-C0> 1lI 30o 802 Huilo do foio do 1Il0ruO-CONH- @ 270 777 Huilo do snrd1na-CONH- @ 259 756 [x] Iléinoin 55iE 3'93 1 7H'1 CONH1I! '\ JCH :; 228 e2o.



  CH3 e17x33o0rr / c2A, 04 1010 CE3 017O #! H; I5 96 1210 H3 '. 398 1210

  <Desc / Clms Page number 24>

 
 EMI24.1
 t? 1? H3C021IiH- -.C2H 254,841 CH .so-e? H35COnx. ¯CH 303 923 ipso-0 CH 3 305 o? H2gcorrxçH - c3 249 1000 OH5 C17B29CONHfHa, 295 1015 chez HuilQ do carthamo-00 3 2o 841 5 Huile do carhuno-CC: iiC -CE 3 299 1014 Ruilo 1 - 299 1014 4H Huilo do harong-001MOH.F \\, \ - "5 262 823 CH3 Huila do '" "± ± Ô3 315 1022 at Exil Witness 595 3451 G? HC02dH H, 230 845 Chez Cl? H31COI3zCH- (j} -TO 275 1011 CE3

  <Desc / Clms Page number 25>

 
 EMI25.1
 01nlaomryH02 315 1098 Chez OIMOU OCH3 325 1061 bu 017H, lCOm #! H- <::

  > -OOR, 552 1125 6H, 01qµ, CONHEÉ ± Br 299 1039 lµ C19H33CONHCH., R.-Br 253 921 6u, 253 C? 33COr $ H! l ¯ 277 1009 OH3 aï 2 O17H3CONHÇ- 362 1342 C2H1-- 017H, CONH? H-Ó N02 289 289 906 2HS C2 Cl? 3CONHrHÙ 315 1125 V2 115 dl CZ? H3'COITFI H 5 382 1210 CH,

  <Desc / Clms Page number 26>

 
 EMI26.1
  1? 55 "5ù ± 9" 5 306 1069 a, Cl? H É ç 3 t] 3 318 .1.5 ..0 "F-; s C17H35oorr" 309 929 .sa.-Q1H35COItH 'H c1 299 l05 3 isc- Cl? H35CU.'iCH i .C 239,906 so-CxII - SCUI;

  & CH. 1.,., 256 929 113 iao-c * a35CarmcH ro2 321 1222 "H3 aa-cZ735ÇOtxH-l..ocH3 bzz 1191 3 i -17H55C" / X $ Cb 3oC g 9 CH, io-C7H35COIHiC I OCH3 33 3 1094 OH3

  <Desc / Clms Page number 27>

 
 EMI27.1
 Cl 79C? NJlTH0 309 1125 Cl 1 0179CO! L! 7.Ó1 27P 995 S! S / C1 C $, 9COrrl H -, \) 30o 1029 CH3 -¯- C? R29CONIij H-N02 245 1004 CZH I5 c7xCorrx g pa zus 1325 C2Ii5 0 NEC 240 C17900NRf 240 62 3 01712900NR7H-Q 2? 5 1G32 CIi2 6 dl CH29conH x3 35 1450 C2H, 5 017% 9 coimîH-î-- OCE3 ga 0179COlm? Ho-OCl! ::> 280. 870 25 al? 9CONRRD - "'CI! ::> 3J9 1620 0 1? 1111> 9 GONHÎ 339 1620 2H5 It

  <Desc / Clms Page number 28>

 
 EMI28.1
 huilo do cxTthano-'l01 IÉÉ. /. Ba 350 1062 2H, hu11C 'do O "'." Hn.nO..CON ".rIÇH-o '.

   Bx 255,825 2H; huilo do o, irthmuo-GoiYHCH.4 '' 1-B .: âi2 1 231> - czx5 oil do CDJ''jha.mO..CCNHH-o-N02 270 985 huïlo 113 270 11ui10 do NO 2 291 1109 S. 5p oil car dl fi OCR 1229 do oa.rtih oil. "'JjIC-OCNHîH. \ .;) - OCH 78 1229 * 4oartl1C1.I11C-0 oil (1NHrH-o- CH 388 1411 1 huila do acrßha.mmo- COWiiH ..- pCH3 300 9 (14 OH3 huilo dl dl Q65 huilo plouronocto-CONHCH 365 a2115. Oil d 290 oil du plouron * cto-oO! MCH-d 290 714 2H5

  <Desc / Clms Page number 29>

 
 EMI29.1
 huüo 1 ci 323 $ 13 8 oil do P1ourononte-oONHCH-Q "323 1158 J2HS - oil do Urdino - CONHO 1 - N02 27 :; 967 OH3 sardine oil-0 1 N02 339 1450 H3 oil do saed3.no.-CONHCH / \ 222? II - CE2 oil of Snrd.ino-c # m1-Q 320 1069 6 "2 huilo do errd.tno-CONHÇA \ ¯OCH3 340 1215 CH3 Oil of sa.dino-COIJïi;

   H. / \ pCH3 279 88? CH3 g3ardïnG-CoNHOH oil OCH3 350 13 09 JH3 Blood cholesterol content (%) gI 'Control 100

  <Desc / Clms Page number 30>

 
 EMI30.1
 ...... CH3 iso-.C? IiSSCON'HGH $ 5 62 Il -lrnCH2clI ... C 8 Il -! NID 68 -IfIIO 60 u .... UHÛOH? 2 "- * 1 ± / CH, I11I - jJrrH 54 Il -NII - () - CX3 CH3 "-1OE ± / 0H 68 Il -1mb. 42 -iOE ± j 55 -lfli ± 63 u 3 62 -I / !! C; p 60 Il -lmCOOCH3 ..53 ".N 44 CH3

  <Desc / Clms Page number 31>

 TABLE 2 LD50 (P.O. mice)
 EMI31.1
  17X31C '(Ô> 50 9 / its CH- Cz x3corr cH g / kg CH3 cx3CONHCH-t v-- CE3> 50 g / kg 5 C17H;

  ) l COUH1H-Q> 50 g / kg Cli-¯1CONH- (J)> 50 8 / k8 .so-cH35coyr> 50 G / ka 2 01? Hl OONH? HQ> 5o slks H2 1? 113l 00NH1> 50 s / ks ô

  <Desc / Clms Page number 32>

 
Further, the compounds of the present invention were administered to rabbits in a dose of 200 mg / day with a rich diet.
 EMI32.1
 on oholostorol, pvvr get the r6sul.iiatd .ta.v.'I'c.'blIJS indicates where "after.



  Blood serum cholesterol, mg. %
 EMI32.2
 Compound 2 so- 4 Bù- 6 Do- 8 so- 10 ao ..



  Compound mainOO3 nainos mai u3 s mainon mainos Control 250 563 890 1150 1750 Pt-sitosterol 250 438 875 106 1200 N N-dicyolohQxyl- lino1éddo 250 120 62 62 65 017 113 a ONHOII- / nN 250 130 65 60 52 1 \ B <JB <Reduction rate of cholosterol of Dosn sorum compound in rabbit blood (after 9 weeks) Control 0 0}? - Sitost6rol 800 mg / kg / day, 2 1 Cl? H3100NHßnCH 100 Ng / kg / day 6 0 CE3 C17H31COl # yH- o-CH 100 mg / kg / day 59.2% 02H 5 (diz 17I31001lliCHD-Cl 100 mg / kg / day 80.1% l7H3l 6H Chez Cl 0 17 il '31 COIUMH.C-01 1 100 ing / kg / day z I, I, '\: J CH3

  <Desc / Clms Page number 33>

 
 EMI33.1
 Cl'f% lcowyn-o- OH3 100 mg / kE: / Day 58t: S9 Chez cil i. '' / H> 'CO1V'HIï-C..CH 100 g,' k, J ': 59tll {* " ....



  CG'F5 CH3 cz, x29aoH 100 ng / kg / day:; 4.5% CE3 orx3 huilo do oanthmo COlmy! L: O # 100 mz / ks / àouw 60.6 iC2R5 r 'soicho oil c0NHj Ù 100 nzPrg / day 67.3% soicho oil C4NÜÇ 1 ..- mapzs / atour 6,> 'CE3 All the products of the invention are new.
 EMI33.2
 compounds unknown in the 11ttrauro.



  As noted in tabloau 2, no fatal case, nor any import toxic symptom, -tut has been established in such large doses (by voio oralo) that 0.5 g per 10 g, in particular 50 g / kg of body weight. Likewise, no significant toxic symptoms or fatal cases were observed when the administration was administered.
 EMI33.3
 journollomont, laying three somainoo, to mice, los aaides one quuntit6s do 19, 0.5% or 0.2% in 10 neimo. The appetite 4tc3.t normal ot los functions digoativos 6taiu.it: I.l1 '>. Í.ll' ..!. 1geos. When we examined the intomo3 organs by disouctiont on Il. t 0. observed no appreciable change.

  <Desc / Clms Page number 34>

 



   The cholesterol reducing agents according to the invention can be administered orally. Usually, the orally administered amount is 0.1 g - 20 g per day, preferably 0.5 g - 5 g per day with continued oral administration for one to five months, usually for three months. The cholesterol reducing agent may be preestorated in any suitable form customary for oral administration. Thus it can be coated in a capsule or be presented in a liquid form, in the form of tablets or a powder.

   When preparing the agents in these various forms, the active compound can be mixed or impregnated in a suitable solid carrier or again, it can be mixed with a liquid carrier such as a comostiblo oil, preferably an oil. containing linoleic acid. You can also use a mixture of sweet or several amide dosages. N-substituted of the invention. It can also be used by mixing with linoleic acid,
The present invention will be described in more detail with reference to the following examples given solely by way of illustration and not limiting the invention in any way.



  Example 1
A mixture of 10 g of linoleic acid and 5 g of # (-) [alpha] -methyl-bonzylumine was heated and refluxed for about 8 hours in 300 ml of toluene in the presence of 0.2 g of p-toluene-sulfonic acid using a water separator.



     After the reaction, the formed toluene layer was subjected to acid washing, alkali washing and water washing, and then dried and concentrated, to obtain 12.3 g of a. desired product with a boiling point of 200-221 0 / 0.05 mm do Hg.

  <Desc / Clms Page number 35>

 



  Elementary analysis:
 EMI35.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.40 <SEP> 81.70
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 10.77 <SEP> 10.88
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3 <SEP>, the <SEP>
 <tb>
 
 EMI35.2
 In the oxcmplua 2 - 3? included in 10 tobluau below we used! Auxiliary dehydration product!
A. p-tolueno-sulfoniquo acid
B. p-Toluenesulfonic acid chloride
C. Sulfuric acid
D. Phenol-sulfonic acid
E. "IRA-400"
F. "Amborlite-15" solvents a. Toluèno b. Pyridine c. Bonzène. d. Chloroforma c. Xylèno f.

   Carbon tetrachloride

  <Desc / Clms Page number 36>

 
 EMI36.1
 80E? NHCH- (] Rail
 EMI36.2
 Ëxen-J aurl Duration pc% H% N% pie Fatty acid 1 1 liaire '801- de la * L ##### ¯¯¯¯ ########### ¯¯..¯¯ ¯¯¯: pIe! Fatty acid -RA "ÉùaÉln vant reactioni" C / nmHg '------------ 1 -------------- 1 --------- --1 ¯¯¯¯¯ ¯¯ ¯ dration; ! (hours)! rique, tick 1 rique laughed tick. tick ----- I ----------------- j ----- f ---------------- j-- ---------------; ------ i -------------------------'- ----- 1 2! -Oleic acid CB A a 8 µ 203-2l4 / 0.05 i 80.98) 1 i 81.22 Il, 24! II, 46 3.63, 3.44 3 Oleic acid II CH- B bu 20 µ 2J4--218 / 0.07 80.98 81.10 11.24 II, 42 3.63 3.43 4 Linoleic acid 1 CH 3 A of 10) 200-217 / 0.05) 61.4O 81.65 10.77 10.90 3.65 3.41 5 Linoleic acid CB D e 10 J 202-218 / 0.05;

   81.40 81.65 lu, 77) 10.90 3.65 3.42 6 Linolenic acid CIl} a lu 204-2l3 / 0.05) 81.83 82.00 10.30 10.62 3.67 3 , 32 7 Linolaemic acid CH i 10 2oc -, - 214 / 0.05 81.83 82.13 10.30 10.54 3.67 3 * 4-5 8 Isostearic acid OE3 Air. 12 206-217 / 0.04 80.56 80.70 '11.70 il'.75 3.61 J 3.58..t: Isostearic acid CE3: b 20 202-218 / 0.06 80.56 80 , 70 11.70 1 3.6l '10 Safflower carthame oil 02H5 8 (2O5-2l? / O, 06) 11 Soybean oil CH3 e 8 204-216 / 0.05! 12 Sesame oil CH3 200-218 / 0.06! Castor oil CB Ouch! 196-216 / 0.05 13 Castor oil 1 CIl} b 8 186-218 / 0.05 Jill 14! Corn oil C 2H5 20 186-218 / 0.05 / 15 Cottonseed oil CH3 A 8 189-208 / 0 , 06 q> ¯ - ## --- ################## .... #. ##.

  <Desc / Clms Page number 37>

 
 EMI37.1
 



  16; Olive oil 3 H 1t33..20 d / '0.05 to, Linseed oil M3 D 3-207 / 0905 16! Olive oil # 3 DIa 10 133-207 / 0.05 /; 18 rapeseed stream 1 ClJ3 o / - <6'jL2 / 0.05 18 Rapeseed oil A a 193--2l4 / 0 ¯ .9 Rapeseed oil 1 ClJ3 12 193-2-14 / oto6 2p, 1 Rice bran oil. 1 # 3 C 8 11 193-218 / 0.05 'Sunflower oil 1 il, OE 188-210.06: Sunflower oil f CH3 A 191-215 / 0.05 2' Chrysalis oil 3 191-215 / 0 , 05! / 22 'sect pleuro- CH 1: 8 196-22 (, / 0.03 23 1 liver island a 8' I96-22G / 0 '0'! Shark liver 1 ClI3 .A. 1 to 10, J.86 -209/0, 06 24 = Bel eine oil 10 ..: .E4--220 / 0,05 25 Cuttlefish oil 1 C "3 10 198-21p10,06 35 oc! Desarine oil M3 a '198 -219 / 0.06 27 Sar oil: in. ClJ3 il 20 201-218 / O, pB <-7 mackerel island.

   CE,! 2W-217 / 0.0.5 L, 2: i IR Mackerel Oil CH; 200-217 / 0.05 28 Scombréoo- / o.es soce 6contré- Cil5 187-216 / 0.06 29 Herring oil CH C2e5 e A 187-216 / 0.06 30 Herring oil 3 A d 1o 186-215 / 0.05 30 Desaurel oil CH3 10 184-213 / 0.05
 EMI37.2
 
 <tb> 184-213 / 0.05
 <tb>
 
 EMI37.3
 31 Menbaden oil CH3 z liver needle 182-222 / o $ oa 1 cod Oil: height CH3! il 8 192-218 / o, o5 j fil,!

  <Desc / Clms Page number 38>

 
 EMI38.1
 1 ---------- liver t Liver oil CH3 182-217 / 0.06
 EMI38.2
 
 <tb> 34 <SEP> Oil <SEP> residual <SEP> @ <SEP> CH3 <SEP> 8 <SEP> 184-223 / 0.08
 <tb>
 
 EMI38.3
 35 Demenuse oil CH3 il A e 8 176-226 / 0.08
 EMI38.4
 
 <tb> 36 <SEP>:

  Oil <SEP>. <SEP> decarthame <SEP> C3H7 <SEP> 10 <SEP> @ <SEP> 199-204 / 0.02
 <tb> 37 <SEP>! Oil <SEP> decarthame <SEP> C4H9 <SEP> A <SEP> e <SEP> 10 <SEP> 197-209 / 0.03
 <tb>
 
 EMI38.5
 to - S ---------------- 1 ------- 1 --------- S ---- 1 ------ to --------- 1

  <Desc / Clms Page number 39>

   Example 38
In 50 ml of toluene, 10 g of linoleic acid, 5 g of (-) [alpha] -methyl-benzylamine and 10 g of dicyclohexy-lcarbodiimide were dissolved individually. The solutions were mixed together in one portion and the mixed solution was allowed to stand at room temperature for 8 hours.



   After filtering the solution, the filtrate was washed with acid, alkali and water, then dried, concentrated and distilled, to obtain 11.1 g of a desired product of a point d. boiling 201-209 C / 0.04 mm do Hg.



  Elemental analysis:
 EMI39.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.40 <SEP> 81.51
 <tb>
 <tb> H <SEP> (%) <SEP> 10.77 <SEP> 10.88
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.51
 <tb>
 
Examples 39 to 74 are shown in the table below.

  <Desc / Clms Page number 40>

 
 EMI40.1
 



  C H B ple Acid lAmine! BH: zC = I # Sol: t P.E.! #### L - ## .....



  RIO "B f thetic Theo- Analy- Theo-! AnalY-1! ### # - ########## '---------- 1 - at tick risk tick ric tick Linear acid CE - () JEther J 200-200 / 0.04 81 81.77 10.77 3.65 3.45 ji 1 LinoUic acid 0E5 Ethen 2Oo-zo8 / o, 04 µ 81.4O 81 77 10.77) 10.73 3.65 3.45 d 40 Linoleic acid CH} 'in <0 Dioxane 204-208 / 0.04 81 '4S'! 81.65; 10.79; J 10 '91 3.65 3.38:' i '1 41 1 1. t Oleic acid C Í. I.! CH CH CH- i f Dioxane 203-219 / 0.06 80 98 '! i Bl, 03! at 11 24%; ! 11.34 3 63 3 49 42 Linolenic acid CH3 -0! TetrahYcU-0-205-217 / 0.05; 81 83 82.06 10; O 10.K5? .67 3.4? 'jj "jjjjj jjjjjjj / j j3) 1 /: Curanne î Iii J?' zij.? 43 Isostearic acid oe, Ether 208-218.07! 8o 56 80.71 il 70 11.86 3.61 3.54 '2O8 2l8 / 0 0? / 80 '06 Ù 80'? 1 '' 44 Ostearic acid.

   M3 Toluene 200-214 / 0.05J80.56 80.98) 11.70 d / 11.87) µ 3.61 3.48 t fi: 1, .. safflower ce5l I 201-214 / 0.05) Oil fatty acid! C2fI5f 'roltiene 201-214 / 0.05 j *' ::: I: * '46 soybean oil OE3 -0 Chloroform 195-218 / 0.05 1 .. oil 3 1 Toluene 189-218 / 0.07 t 1,47 i, of Acid sesame fatty oil. 1 f CH; t -0! t Toluene! [

  <Desc / Clms Page number 41>

 
 EMI41.1
 48 '- CH3 oil fatty acid I! -0 f Tetrachloride 193-21} /O.01 ridn Tetrachloride 193-213 / 0.07 ÉÎàÉ / bzz) of carbon 1 f 1 i of ric.1D d-0 oil J -0 ji of carbon 1 of rapeseed oil CH3 Benzene /194-211/0.06 rapeseed 50! CiI5 oil fatty acid. pyridine 196-215 / 0.06 olive oil f "Benzene 1, its oil fat II Benzene 185-214 / 0.06 / its oil fIt.



  52 oil fatty acid CR7 :: Toluene la8-218 / 0.05, cotton M3 Toluene 53! Oil fatty acid CH3 -0 Toluene; 3, gg.-21g / O p $ 54 i Oil fatty acid CH7 :: Ether 1g5--21 $ j0.06,! d f peanut;. 1 E <r 195-awb, 06 55 c1 of oil fat f CH3 -0 Toluene t 191-219 / 0O6 olive Oye3 Toluene 56 3acid 'gxuas oil C3 -0 Toiuéne 196-2l5 / O.05 56, cide "fToÍuene oil fat 196-215 / 0,05 c.ry8alide 57 1 A.ci3 oil fatty acid Benzene 205-222 / 0,03 d shark liver .." "... - - - ......- ¯¯¯¯, ¯ - .. --......-..-..-. '.... - ........- .. ......- 11'1> 81

  <Desc / Clms Page number 42>

 
 EMI42.1
 58 'Oil fatty acid CH3' Toluene 181-228 / 0.05! ;

  of cuttlefish 3 # 59 = Oil fatty acid C3,! Ether 192-226 / 0-07 'of sardine J Ethen 192-226 / o, 07 µà d,> "' 6lÎ of oil JEther j '' / Ô 5 Oil fatty acid CH3 = Ether 194-216 / 0 mackerel 3 if 61 {Oil fatty acid CH3 benzene '1ß0-217f0? 06' from scombrésoce "# <SC 'bEéS C x- z Grana oil acid! Ws - () Ether 192-218 / 0,05 ide herring of ethnae OEµ j -0 'etsen 192-218 / c, oo 63 Oil fatty acid CE3 Toluene: L82-2.18J0,05! Of saurel # / gnas oil-i EO / Chloroform 186-2l6 / 0.05) Oil fatty acid - / \ 'Chlorofo = 3 186-n6 / C), 0.5 from cod liver') 2 $ 6-J '.G / 0.45 65 Oil fatty acid CH Tetrahydro- 180-219 / 0.05 from trout 3 # .furanne 66 Oil fatty acid OE3 y \ iTéttlvd> j 194-225 / 0.05 Ida mullet - "turanne { furan z fatty acid CH 'Toluene oil 189-215 / 0,06 of menuse 3 d / "

  <Desc / Clms Page number 43>

 
 EMI43.1
 r 68;

   Oil fatty acid 8 5 - (") Dioxane. J 193-226 / 0.05 's of menhadeZt! #! 69. Oil acid 03, j Zl Benzene 196-229 / 0.0-5! ! of winter eel CE5 lBenzene 196-229 /, 5) '70 oil fat CE fi Dionue 389-22t / 0.45 of pleuronc.cte t #! 71 'Oil fatty acid G $ - / Benzene 17.3--225 / 0, C6 de baloi - at, hUiie 3; C 1 Benzene 17; -22 ± / Q C6 72 Î À C- 4d e éé; = oil CH3 -; Tc; .uaue 39 --218i, E3'l: of liver 73 Llcidegras <oil! 2H5 - Toluene 194-228 / 0.08 1 residual '#' #. z Fatty acid d- haî 1 C3 Y - (J JDioxcnne 199-209 / 0.06 decarthame C5b) / Moxane 199-2a9 "; OE) --------- to -------- -------- 1- -

  <Desc / Clms Page number 44>

   Example 75
For 24 hours, a mixture of 10 g of linoleic acid and 6 g of # (-) [alpha] -methyl-benzylamine was heated at 180 ° C., removing water from the reaction system.

   The reaction mixture was immediately subjected to distillation, affording 11.3 g of a desired product boiling 203-221 C / 0.07 mm Hg.



  Elementary analysis
 EMI44.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb>
 <tb> C <SEP> (%) <SEP> 81.40 <SEP> 81.56
 <tb>
 <tb>
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 10.77 <SEP> 10.86 '
 <tb>
 <tb>
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.55
 <tb>
 Examples? 6 - 103 are shown in the table below:

  <Desc / Clms Page number 45>

 
 EMI45.1
 RooNA- 0: & CH, - C4 1 X a 'OË5] Rua a C3117
 EMI45.2
 ! pie Acid 1 ture of the i p.E. - ##### .... ¯¯ ### .. ¯¯ i # J..



  RGWH 'ture PE ---------- i ------------ Nu' .La- réaC- ,, reaction .c / ... Theo- i, Analy Theo- Theo- Anale-j, (hours> s) "1 1 tick tick -1 tick tick tick -1 76 Isostearic acid 0 180 24) X6-Zl8 / O, 06 80.56 80.6? 11.70 11 , 98! 61 3.38 77 4 '1 oleic acid lof fi 180 24 206-217 / 0.05! 80.98 81.28 II'24111'5 3.63 3.39 z79 '78 Linolenic acid 0 180 24 209-216 / O, 06 81.83 81.95 10.30 / 10.54 3.67 3.38 79 Oil acid from J 1 cart;

  hame o) 180 24 l 194-219 / 0.07 81 1 Oil acid yellow of 200 20 197-221 / 0.05 mals of oil c 180 20 195-208 / O, C6 82 Acid of oil of x 180 24 197-215 / 0.05 Ethnic cotton 705
 EMI45.3
 
 <tb> Acid <SEP> of oil
 <tb>
 
 EMI45.4
 sesame oil 160 198-206 / 0.04 fi 1 84 Oil acid 160 198--206 / 0 0E castor oil 0 160 36 200-222 / 0.04 85 Oil acid ¯ olive 180 188-211 / 0 * 06
 EMI45.5
 
 <tb> Acid <SEP> of oil
 <tb>
 
 EMI45.6
 rapeseed 180 24 206-216 / 0.05

  <Desc / Clms Page number 46>

 
 EMI46.1
 y Ù 87 j Acid of hiii 1 of J! 180 198-214 / 0.06 to 180 1 24 198-2riz i 88;

   Linseed oil acid o j in 24 188-215 / 0.05 1 89 =. Bran oil acid o j 180 j 181-213 / 0.07}
 EMI46.2
 
 <tb> 90 <SEP> Acid <SEP> of oil <SEP> of <SEP> liver
 <tb>
 
 EMI46.3
 t of shark j x j 180 d 24 1 (18% -22 À / O, 05
 EMI46.4
 
 <tb> 91 <SEP>! * Acid <SEP> of oil <SEP> of
 <tb>
 
 EMI46.5
 ;

  whale 0 1 0 26 175-225 / 0.04
 EMI46.6
 
 <tb> 92 <SEP> Acid <SEP> of oil <SEP> of
 <tb> {mackerel <SEP> o <SEP> 180 <SEP> 24 <SEP> 193-208 / 0.06
 <tb>
 
 EMI46.7
 93! O-ilile acid 180 183-2l5 / 0.07 3 Saurel o! 180 24 189 - PI5 / 0.07 94 Acid from cuttlefish oil o '2OO (18 186-214 / 0.06! 95! Acid from liver oil 208 (18f - 214 / 0.06 from cod 200 () 18 183-222 / 0.08 96 ± ± hereng cide of hct3.le of 2IO () 'ha, tolbnile 210 (") 18.

   193-215 / 0,04 97 acid oil of sardine oil o 180 20 196-220 / 0, 08
 EMI46.8
 
 <tb> 98 <SEP> Acid <SEP> of oil <SEP> of
 <tb> pleuronecte <SEP> o <SEP> 180 <SEP> 24 <SEP> 194-221 / 0.05
 <tb>
   () In an autoclave

  <Desc / Clms Page number 47>

 
 EMI47.1
 1> oil acid oil acid menbaden o 180 z 190-218 / 0.06 '100 <Liver oil acid o 180 z 195-22Q / OtO5 101!. Real oil acid 180 186-215 / 0.05 / ÉÀIÎe 0 180 20 186-215 / 0.0.5 102 '.t'kcide of 202-21G oil ji jca thame + j 180 20 202-210 / 0.04, 103 i Safflower oil acid.

   130 25-211 / 0.05, carthawe IBO)!

  <Desc / Clms Page number 48>

 Example 104
For 30 hours, a mixture of 10 g of methyl linoleate and carbon dioxide was heated at 180 ° C. in a nitrogen atmosphere.
 EMI48.1
 6 g of t-) O <-methyl-bonzylamine by removing methanol from the reaction system. The reaction mixture was distilled to obtain 12.3 g of a desired product boiling 200 - 216 C / 0.05 mm Hg, [[alpha]] D25 -59.5.



  Elemental analysis:
 EMI48.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.40 <SEP> 81.60
 <tb>
 <tb> H <SEP> (%) <SEP> 10, ?? <SEP> 10.81
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.48
 <tb>
 Example 105
Laying 3 hours, we heated to 150 * Ci a mixture of 10 g
 EMI48.3
 Methyl esterate, 5 g (-) o-methyl-bonzylamine and 1 g sodium methylate, excluding from the reaction system the methanol formed as a by-product in this case. Then, the reaction mixture was washed with acid, alkali and water according to the usual methods, then dried and concentrated to obtain 12.3 g of a desired product of a point d. boiling 205-226 0 / 0.06 mm Hg.



  Elementary analysis!
 EMI48.4
 
 <tb> Théoriaue <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 80.56 <SEP> 80.50
 <tb>
 <tb> H <SEP> (%) <SEP> 11.70 <SEP> 11.78
 <tb>
 <tb> N <SEP> (%) <SEP> 3.61 <SEP> 3.74
 <tb>
   Example, 106
To a mixture comprising 10 g of ethyl oleate and 5 g of
 EMI48.5
 (") O'methyl-benzylamino, a solution of 0.5 g of sodium in 8 ml of ethyl alcohol was added. The mixture was reacted.

  <Desc / Clms Page number 49>

 at 160 ° C. for about 2 hours, removing ethyl alcohol during the reaction. Then, the same treatment was carried out as those described in Example 2, to obtain 12.0 g of a
 EMI49.1
 product derived from a P, Eo of 208-218 C / 0.06 mm Hg.



    Elemental analysis:
 EMI49.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 80.98 <SEP> 80.89
 <tb>
 <tb> H <SEP> (%) <SEP> 11.24 <SEP> 11.18
 <tb>
 <tb> N <SEP> (%) <SEP> 3.63 <SEP> 3.80
 <tb>
   Example 107
For 12 hours, a mixture of 10 g of carthamo oil and 6 g of (-) [alpha] -methyl-benzylamine was heated to 200 0 in an autoclave, then immediately distilled to obtain a solution. obtain 13.0 g of a desired product with a PE of 197-226 C / 0.05 mm Hg.



   Examples 108 - 139 are shown in the following table

  <Desc / Clms Page number 50>

 
 EMI50.1
 RCONHLCH 0 R "" 1 Ilimit x 8 "" "Cil5
 EMI50.2
 Exem- '1: Exem- Tenpâra-i Duration i; , r¯'.¯C% H% N% F Ester or. B "": p1e of; Turkish 'do! de la Cata-! 801-! P.E. ## ¯¯ ## ¯¯¯¯¯¯¯¯¯¯ '--1 ------------, PJoe j glyceride 1 8 ref- the reac-: lsrsor reaction; r.ant 'C / mm .flg = Théā Ana1y-: Théo- À'.na ly-1 Thdo-:

   Analysis (0) 1 (hours) i tric tic ric tic; riqueJ tick 108 'Linoleate! :; z¯¯ fi:;,, methyl jo 4 200 12 Î 200¯2ltf / 0.04f 81 t4O 81.58 10, 'j% "10.93 3.65 3a 109 1 Ethyl linoleate jojz 180 48 203 -209 / 0.05, 81.40 81.56 10 7.7 io, 80 3.65 3a3 $ - 110 Oleate m- 110 Oleate y 0 160 z CtBu, 120 (k-227 / 0.06-. 80 , 98 81.21 11.24 11.42 a 'a63 3 a' '' i tby1e i 0 J 160 1 Z: OtBu f 1; 80J98; 81.21 Il..24 Ii f Il, 421}, 63 i 3.44 Methyl 3 160 2 NaOCHxi CR30H, 206-218 / 0 eo7i 80.50 80.78 11.70 Il, 99 3.61 3.46 112 Linalenate Cie 200 3967 methyl! 200 14 i206-218 / 0.05! 81.83 81.89 10.30 10.56 3.67 3.3 ::

   methyl j ;! bzz Methyl ester 113 of carbohydrate 1 r .. thame car-t. il- 200 14 198¯209fp, 05
 EMI50.3
 
 <tb> 114 <SEP> Ester <SEP> methyl
 <tb>
 
 EMI50.4
 114 of seed oil Sema 200 '198-213 / 09 051 Iu 115 methyl sane l' 1 4 200 12 J198-213 / 0.05 l '1 "1' 1 11.5 Es: methyl ber 1 of ric oil ' -nj 0 1 180 42 '199-218 / 0.05 116! Methyl ester!! rapeseed oil! cz 180 40 il88-209 / 0.05 -..- L -. ## -. ¯.¯ j.¯L - # .. # .. ¯.L-¯ ## L ## L # .L # -¯! ¯¯¯¯

  <Desc / Clms Page number 51>

 
 EMI51.1
 ! - fi,! i "'1! ... ¯ il? Methyl ester!! t! olive oil 0 2 150 3 Na1: 188-209 / 0.051 lI8, Atethyl ester" t.! 118 'Methyl ester;

   oil from his 1 He! bzz! 1o methylated rice ester! 4 180 10,! 189-214 / 0.15! 113! Estermethyliqme 1 180 5-208 / 0.05i of cottonseed oil x 1 180 38, "195-208 / 0.051 120! Methyl ester of oil from the! Chrysalis z 1 180 38 Ï!, 193-216 / 0.06j z Methyl ester of sardine oil 1 180 1187-218 / 0.0511 sardine law 180 42 187-218 / 0.051 122 Estermethyl ester! 322 of 180 z Ii fish oil 180; ie7-212 / 0.05t bed
 EMI51.2
 
 <tb> 123 <SEP> Ester Methyl <SEP>;
 <tb>
 
 EMI51.3
 oil! t. 19? ¯22410.05 pleuronecte 0 180 197-224 / 0.05 124 Car oil- 190 199-215 / 0.051 'thame car- z. 190 20 199-215 / 0.05 '125 3in oil 0 4 190 18! 187-iL, </ o, # l i 1261 Soybean oil bone 4 190 18 195-218 / 0.06 j 127! 'nem1 Tour oil- 1 o! 4,200 12 196-212 / 0.06 1128 1 Oil from March i! o 4,200 12 t 195-218 / 0.07 ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯: f. :

   

  <Desc / Clms Page number 52>

 
 EMI52.1
 i J: 1.! if! 't 129 Liver oil; 190 t; 184-215 / 0.07 '; 129 shark: t: goose 190 -184-215 / 0,0? F Oil 180 130 'Cuttlefish oil 0 4 180 16! 190-216 / 0.07; 131 '! Sardine oil 4 190 14 194-218 / 0.07; 132 1 t rcau Maque oil- o 4 190 15. 193-20G, 1, C6 133iBuiladescom- il f 2C0 :: 9--2I8O! brésoce 200 Le:

   J.21â / OtC6t Oil iare3g! o i. 4 20 t 12 19¯2I8! ',' ?. ±. , 134 Harerigi oil 0 4,200 12 19-218 / 0.04; 135 '!, Oil sai - el o 4 200 189-214 / 0.06 .:, 11135 tHui1e of sa'l1. "El! 1 0 4 200 12 {' i 189-.2:! .. 4/0, O6: 135 Pile oil- Iii l ronocto o 4 190 12 1 195-217 / 0.05J 137: H: uil <eden.en- 214 137 j 1 haden - Oil a6n- or 4 190 14 193-214 / 0.04. t 138 1 Liver oil! o 4,190 12! 193-226 / 0.06J 139 Residual Htzi3e a: 4,190 16. '108-217 / 0.07 If!:! 1 t; i: - i t j

  <Desc / Clms Page number 53>

   'Example 140
Linoleic acid chloride (30 g) was dissolved in
50 ml of anhydrous ether.

   While cooling and stirring at 0 - 5 C, the solution was added dropwise to a mixture of
 EMI53.1
 z. 2.5 g of 1 (-) -methyl-bonsylamine in 100 ml of anhydrous ether and 8 g of trimethylamine. After the dropwise addition, the reaction mixture was boiled for 2 hours to complete the reaction. The ethereal solution of the reaction product was washed with acid, alkali and water, then dried, concentrated and distilled, to obtain 42 g of a desired product of a PE of 209- 218 0 / 0.05 mm Hg.



  Elemental analysis:
 EMI53.2
 
 <tb> Theoretical <SEP> Analytical-
 <tb>
 <tb> C <SEP> (%) <SEP> 81.46 <SEP> 81.38
 <tb>
 <tb> H <SEP> (%) <SEP> 10.77 <SEP> 10.81
 <tb>
 <tb> N <SEP> (%) <SEP> 3.45 <SEP> 3.61
 <tb>
 Examples 141 to 175 are indicated in the following table:

  <Desc / Clms Page number 54>

 
 EMI54.1
 o c6-Yethyl-benzylanine (-) --¯u x C-Ethyl-benzylamine (-)
 EMI54.2
 Acid halide product Produi Exe Acid halide -aSSSî-! H% N% plus 1 Solvent re of "" "! -------; --- .. '.. --1 --¯¯¯¯¯¯1 No Acid xi con den-: C / mmHg 1 Theo- 4naly-1 Theo- ànely-1 Theo- "ànaly-jation; tick tick 1 tick tick! tick: tick ,.



  141 / Oleic acid if j / CO- ketone! / 2O8-2l? / 0.05 80.98 81.14 / ll, 24 fIt 1 i 3.94 141 J Oleic acid CI! 0 facetone 2CO3 2o7-21? / 0.05 80.98 j 81.14 il, 24 11.30! 3.63 3 65 1 uran / ea.uf: 143 .Isostearic acid Cl o. Ether t Trimé 206-219 / 0.06 i 80,, 56 8O, 7 '! - 11.70 Il, 92 3.61 3.40: thy1aminei 144 t J Isostearic acid ci Toluene Pyridine 203-21 - // 0.05 80.56 80.71 il 70 Il, 85 3.61 J 3.40 145 1 Linoleic acid CI '1 1 Toluene ipicoline 206-213 / 0.0.5! 1 "11 '70 ll' 85 '1 145 Linoleic acid CI! O 1 etone" Pico1ine! 206-213 / 0.05 fIt f 81.40 81.64 10.77 10.83 3.651 ', 69 146 Linoleic acid Methyl-Trietil- 203-216 / 0.06 81.40! 81.73 10.77 10.92 3.65 3.31 butyl amine <j 146 "linolei ketone. amine '') '' 147 Linolenic acid 1 CIl Ether iTriethyl-1 202-218 / 0.05 'j 81.83) 81.92 10.30 10.54 3.67'. 44 .L ::

   J 148 Linoleic acid! d o Benzene Ï Dimétby j -1 204-216 / 0.04 81.83 81.96 10.30! 10.65 3.67% EOII 148 Linoleic acid IBenzene {aniline 81.83 81.96 10.30: 10.65 3.67 laniline 149 F amine oil acid II III /) '. L * 149 Oil acid Cl! <ROH 197-208 / 0.05 water 1 x DiOJ # U1Jl.e! KOII KON 1,197-208 / 0'05! yew water! 150 Safflower oil acid Dioxane / KOH 198-211 / 0.05
 EMI54.3
 
 <tb> water
 <tb>
 
 EMI54.4
 Safflower Dioxane / KOII 198-211 / 0.05 151 Acid soybean oil Acetone / ïL, CO- 196-210 / 0.06 'soya ci Acetone / 1 l C03 If 1 <) 6-210 / 0.06 thread! ! t! ... ¯ ---' ----------- .......... ..-- ¯ -.: .. ¯ ------ ¯. ..- ------------ ¯! .¯ ---------; .., ------.; .. ¯ .---. ¯¯ L¯¯¯¯ = -----..-- = ....

  <Desc / Clms Page number 55>

 
 EMI55.1
 



  # - ###### - - vzw z¯ - ¯¯ 152 Oil acid of ci 0 [1 iEther: Pyridine j 1 198-2l4 / 0.06! , sesame of oil F i C1 Ether Iridine; 198-.4 / 0.06 153 i 'Castor oil from ¯ = Ether oil! Ibrri dine 193 -. $ / 0 153 '1 Ù oil acid with pyridine j 193-218 / 0, w. 154 Cl oil hyacid; ÎEther::

   Pyridine 2G7-22? I, O 06 155! ; Oil acid n./nrtc:i "of olive Cl x .Toluene Trimel86-21? / 0.05) thylamine 'i µ6 j Aido dlhpii rice bran Ci o toluene 2'ri.ëthyl-' z son r., iz amino 157 Oil acid from j) j .-. # -, / 'cotton: from oil cïs o Benzene 1> yridine 194--213 / 0.05 158 Oil acid from Î t;: chrysalis Cl o Toluene Pyxidine 19b-à ± / O, 06 159 ÉÎÉd Cl! / Na0H 208-22l / 0, D8! na3: a of oils 0! Acetone /: N&OH 208-221 / u,! - 'tj l ea, iz Acid of linseed oil ci o Ether jryridine .i9U-2i1 / 0.06; 161 Acid of icc-pip / oo oil'; 161 sunflower 1 CI to TetradCO- # 3a0H 195-212 / 0.05 sunflower Cl; o Ù 1 'NaOH 195-212 / 0.05.



  162 oil oil Cl 'Methyl- 8C: 03 189-21.5 / O, Ot- lipleuranecte' 'butyl #% C () 3
 EMI55.2
 
 <tb> acetone
 <tb>
 

  <Desc / Clms Page number 56>

 
 EMI56.1
 165: Oil acid d! ! x Acetone / water! 'NaQH, 185-218 / 0.04 163. -Oil acid of Ii CI F x 3% acetone = 2aOH i 185-218 / 0.04! = shark liver l 'i 164 Cl to ketone oil / water licide; ria2C03 184-209 / 0.05 164 = whale .de Cl. ",: f 0 Acetone / water; lfa2C03 i 165; oil acid of t Cl to;! Dioxane / 110aOH 1: 186-217 / 0.05 1, cuttlefish 1 d water 166 = Cl oil acid 1 x) Dio3canne / K2C03 1 198-213 / 0.05 # sardine t water;! Z Cl oil acid from Toluene-Pyridine 195-211 / 0.05; maquerea7a 168 t i.cid.e ci. 1 h'.1il of CI: o Di ox; q nne / 1 HaOR 105 e scombri5soce =. Water i 169 'Oil acid of CI o Toluene pyridine x - ßz.'7, .h5! - 170 'Acid' t oil herring Cl!. i!;

   NaOS; 18-214 / 0.05! , 170 1 J..oil acid Cl o i Acetonuf ucz;. &, AO 11 'i81.l {' O.ú5
 EMI56.2
 
 <tb> will know
 <tb>
 
 EMI56.3
 1'71 t! aaure1. oil key 1 i PYridine 1 171 Oil acid c cs r CI o Toluene Pyridtne! 1925/005! mùnhadcn; 1? 2 Oil acid; ci z c etone / water; I: 1j: rt i 134- 2 {} 8 /> 05 1 toie of cod fi ': 1? 3' Oil acid from Cl? n 'Ether: Pyridinc 196-215 / 0.04' oil liver; <0 1..ketone / ce.uÏ fi! i KOa 188-218 / 0.06 174! Oil acid; d! or! Acetone / water iKOB 183-218 / 0.06: residual f l i, CI - t oil cide! ..



  175 'Oil acid of ci i 0 iAcetone / cauiNaOR 189-205 / 0.06! 1 '' l ¯¯¯¯¯ <¯¯¯¯.¯¯¯¯. 4 Î? ¯¯¯ ¯¯¯ Î Î

  <Desc / Clms Page number 57>

 Example176
Lying for 7 hours, a mixture of 100 g of carthamo oil, 43 g of d (+) [alpha] -methyl-benzylamine and 2 g of boric acid was heated to 140 0. Then, the reaction product was dissolved in ethor. The obtained solution was washed with 5% aqueous hydrochloric acid, 5% aqueous caustic sodium hydroxide and water, and then dried, concentrated and distilled, to obtain 121 g of. a desired product of PE of 202-209 C / 0.04 mm Hg.



   Examples 177 to 223 are shown in the following table.

  <Desc / Clms Page number 58>

 
 EMI58.1
 



  RCONHCH- 1 Ref
 EMI58.2
 
 <tb> TemperatureDuration <SEP>. <SEP> erase <SEP>. <SEP> Acid
 <tb>
 
 EMI58.3
 ! Exemplel Glyceride Amine R "- de la de la P .. C / m Hg boric reaction 'c.on (hours) boric reaction (hours). I: (0) 177 - Linseed oil d (+) CH3 ij 140 201 -222 / 0.05 5 178! Soybean oil (-) i EC 2CO-218 / 0.06 178 Soybean oil (-) EC 3: U 2CO-218 / 0.06 5
 EMI58.4
 
 <tb> 179 <SEP> Oil <SEP> of <SEP> sunflower <SEP> d <SEP> (+) <SEP> C2H5 <SEP> 4 <SEP> " <SEP> 198-219 / 0.06 <SEP> 3
 <tb> 180 <SEP> Oil <SEP> of <SEP> sound <SEP> of <SEP> rice <SEP> d <SEP> (+) <SEP> C2H5 <SEP> 6 <SEP> 201-225 / 0.04
 <tb>
 
 EMI58.5
 1 181 Corn oil d i +% C3! 200-21 <, 05 1 182 Sesame oil. 1 (-) C} "3r ti 189-213 / 0.3 Hazile cotton. It! '' '! 183 Cottonseed oil (-3 C4H9 150 203-230 / 0.0? 184 Castor oil d (+) 4 B "9 140 205-218 / C. (JE ..



  185 5 Shark liver oil L (-) 3 4- 193-3jCC% 3
 EMI58.6
 
 <tb> 186 <SEP> Oil <SEP> of <SEP> cuttlefish <SEP> d <SEP> (+) <SEP> CH3 <SEP> 6 <SEP> " <SEP> 190-222 / 0.05 <SEP> 1
 <tb> 187 <SEP> Oil <SEP> of <SEP> sardine <SEP> l <SEP> (-) <SEP> C2H5 <SEP> 6 <SEP> " <SEP> 198-224 / 0.05 <SEP> 1
 <tb> 188 <SEP> Oil <SEP> of <SEP> mackerel <SEP> l <SEP> (-) <SEP> C2H5 <SEP> 8 <SEP> " <SEP> 200-218 / 0.06 <SEP> 0.5
 <tb> 189 <SEP> Oil <SEP> of <SEP> scombrésoce <SEP> d <SEP> (+) <SEP> CH3 <SEP> 202-218 / 0.06 <SEP> 1
 <tb>
 
 EMI58.7
 ! ¯ ..... ¯L- # ¯ ###! ¯¯¯¯! ¯¯¯¯L # ¯¯¯ - ## ¯¯¯L

  <Desc / Clms Page number 59>

 
 EMI59.1
 
 <tb> 190 <SEP> Oil <SEP> of <SEP> herring <SEP> l <SEP> (-) <SEP> CH3 <SEP> 140 <SEP> 188-219 / 0.05 <SEP> ' <SEP>
 <tb>
 
 EMI59.2
 191 Saurel oil a (+) 'ca3 160 199-z28 / o, 04 z Cod liver oil, (-) C3H,., 4 160 6-232 / o, Q2 z9' Pleuronect oil d (+)

   CH9 r 6 2pp¯2? 3 / pp
 EMI59.3
 
 <tb> 194 <SEP> Oil <SEP> of <SEP> whale <SEP> d <SEP> (+) <SEP> CH3 <SEP> 7 <SEP> 200-218 / 0.05 <SEP> 1
 <tb>
 

  <Desc / Clms Page number 60>

 
 EMI60.1
 Acid or ester ¯..y 195 Linseed oil H ci (+) CH3 145 201-222 / 0.05! 196 Soybean oil H) ± (-) ECµ 200-219 / 0.05. 3 J 197; Sunflower oil H gas CH 5 196-221 / O, 05 3 198; Rice bran oil CH3 d (+) CH3 5 205-225 / 0.05 199 Corn oil CH3 d (+): C2H J = 5: 200-220 U, tJ6 3200 Sesame oil H Ô (-) G33 18à-2l5 / 0.03 3 201 Cottonseed oil CE3 (¯) rLH fi 205-230 / 0.05 202) Castor oil CH3! (, -: ± R 6 c08--2i9 / 0 Otr 203 Shark liver oil;

   H a C, .3¯ 5 198-225 / 0.05! 3 a 20+ Cuttlefish oil C93 d (+) C.511 7 I38-224jO, c35 205 Sardine oil e 2 "5 d C3H, ±? 198-225 / 0.05! 1 206 Mackerel oil H d C3 3 200-21S / C.OS! 207 Sconbrésoc e C (-) C499 200-22f / 0, C7! 3 208 Herring oil d (+) C4H9 189-2-19 / 0.05 209 Saurel oil OE3 3 "1 .3 8;" 198-230 / 0.03 1210 t Cod liver oil H (-) c3H7 8 208-230, / 0.02 1211; Pleuronect oil H (-) C499 5 20O-225/0 'C4 3 212 Whale oil H d (+) 3? 2a0-219 / 0, Q5 3 - - - - - - -----.

  <Desc / Clms Page number 61>

 
 EMI61.1
 xem- RC00 ¯ ... Durôe <"'"' - ""; ##### ¯- "f --- l1% ---- ple ########## .01. Of the erasure Acid PE C% g 9 ('g pIe: 1 eti of boric! .CI ----------: ---------- i N f R f .A, (hours (oc mm g! Theo- - Anal 3r- *, 1 Theo- Analy-! Theo-.

   Amlyl,; 1 ures! (OC) t f f ¯.¯ i tick tick; ¯; - t ----- ¯r .. ¯, ¯ ¯ 214 Cle2g a .50. J203-223 / 0.05! 81.83! 81,? C '10.30 10.17 3.6? 3 & T 214 j j 1 17'291 R 1 '1 d (+) 1 ca, 1.50! 203-225 / 0.04j '81.83) 81.78! 10.30! 10.17 ', 61 3.69 214 C1 3 (-)' 3 145 2 203-225 / 0.041 81, 8 81,? 8 10.30 10.17 3, E '/ 3.691 215 1 "'; 1 H l, (-) cg 3 Il 5 140 j 2! 200-219 / 0.05; 81.40 81.19) 10.77 10.69 3.65 3 87 2t6 cl? H3I CH3 d M j CiI5 if 8 145 1 j 204-221 / 0.05! 81.55 81.49 t 10.90 f 10.81 3.52 3.42 217 c 15931 C2H5 d (t) r-2-95 145 1; 200-219 / 0 , 05) 81.55 81.38 10.90 10.80! 3e52 3'65? 18 Ci35 'zso- H a (-) "3. 5 3; , 200-220 / 0.06 # 80.56 80.33; 11.70 11.54 3.61 3.65 18 Iso- (+) Inca .. 145 '200-220 / 0.06j 80.561 80.33:

   II, '70 111.54; 3.61 3.65 '¯19 1 iso- 1 H "(-) 5 145 3- f' 205-216 / 0.051 00.56 Î 00.42 11.70 Il 4 3.61 3.71 17" 5 205-216 / 0.05 80.56 80.42 11.70 11.43 3.61 3.71 20 so- 1 H 1 (-)! o! 8,140 2 1205-219 / 0.051 '80.73 80.69 11.80 11.79; 3.49 3.3 "9! 23 17I31 3 d, (.) M3 8 140 2 200-209 / 0.05 81.40 81.31 10.77 10 3.65 3t49 fi !, 1221 c l7H3l CH3 d ('C3H'j 145 z 200-208 / 0.05 81.69 8I, 4.9' 11.02 11.00 3 4O 351 '! 23 cl? R33 1 CE3 4 145 201-205 / 0.01 80 , 98 80.88 11.24 Il, 21, 3.53 ...



  '"########"' * '' *** #### '### "" - "' '##" -'-' ### '' - ". ## - ..rm.t.. '1 ..

  <Desc / Clms Page number 62>

 



    Example 224
For about 8 hours, a mixture of 10 g of linoleic acid and 5 g of (+) [alpha] -methyl-benzylamine in 300 ml of toluene was heated in the presence of 0.2 g of p-tolueno acid. -sulfoni- that using a water separator.



   After the reaction, the toluene layer was washed with an aqueous solution of acid, alkali and water, then dried and concentrated, to obtain 12.1 g of a desired product of a. PE of 200-211 C / 0.05 mm Hg.



  Elemental analysis:
 EMI62.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.40 <SEP> 81.71
 <tb>
 <tb> he <SEP> (%) <SEP> 10.77 <SEP> 10.93
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.38
 <tb>
 
Examples 225 to 259 are shown in the following table, in which! Dehydrating agent:
A. p-Toluenesulfonic acid
B. p-Toluenesulfonic Acid Chloride
0, Sulfuric acid
D. Phenol-sulfonic acid
E. "IRA-400"
F. "Amberlite-15" Solvents a. Toluene b. Pyridine o. Benzene d. Chloroform o. Xylene f. Carbon tetrachloride

  <Desc / Clms Page number 63>

 
 EMI63.1
 a-Re \ ==. /] ROIµ $
 EMI63.2
 3xem-- fi.

   Pxodui auxi- 1; i 1 Duration ic% T "H%" "1; If ple Fatty acid Street liaire: 801-, de la; FE; N desby- vant set on 'C / m Hg Theo- 1 Tea t.nal7-'" ' -é "dratati on 1 (hours),, 0- i Jilla y- 0- Jill Y-.LU 0- Ana1y-;, üratatioa - - ri ue. tiq ri ne te riqae 225 Oleic leide f 1 # -! A leaked: 8 ¯ = 203-211 / 0.05 80.98 81.21! i 1I, 24.11.45 3 to 3 3a t.5226 oleic acid: CH3:

   B b 20 f 20.5-216 / 0.07! ± 80.98; 81.19 11 11.24 11.41 3.63 3, .g 227: linoleic kcide M3 b d! 10 200--211 / 0.05i 81.40 81.63 10.77 10.93 3.6 $ 3.41 228 Linoleic acid M3 D 'e; 10 f; 201.-2I0 / 0.05 ± 81.40 81.66 in, 77 10.9? 3.65 i 3.43 229 Linoleic acid 1 CH3 iDe: 10 f 201-213 / 0.0511 81.83 82.09 10.30 10.6l! 3.65 3.32 230jAcidelinoléniqae CH%! e! 10! 201-213 / 0.05 81.83 i 82.09 10.30 10 a59 3.6? 3.4TJ 230 f ': linoleic acid 200-2.12 / 0.05; 81.83! 82.12 10.30 10 59 3.67 3.4! L1 .: 231 cide 3.soseari e GH3 AJ f 12 206-218 / 0.04J 8i, 6 80.78 11.70 il, '76 3.61 3.5'f 232 isos1; eric acid CH3 B b 20 f 201-219 / 0.06 '80.56 80.79! He, 70! 11.98 bzz 3.46: 233 Safflower oil C2HS F e g 205-217 / 0.06! i .....



  23. Soybean Hume CzTI5 A e 8 20-2.0%, 05 fI f: .. 1:.,.



  234 1 Soybean oil CH3 f 2OJ.-210 / 0.05 ** i * 255-Sesame oil eH3 A f 200-213 / 011061 il! 236 'Castor oil EC, A d 8 197-215 / 0.05]! . 3 ¯. 9? 5 /, 5 i t r

  <Desc / Clms Page number 64>

 
 EMI64.1
 - z Corn oil = C2H; B bu 20! 185-218 / 0.05J 238 ei Cottonseed oil CS 3: f 189-209 / 0.06; 239 Hui.le 8'olive i 3 j D a 8. 183-2o8 / U, CS ± 240 Linseed oil EC [3 c to 10 F i87-211 / 0.05 241 i 'Rapeseed oil CH a 12/19> 2l6 / 0, 06): 41! Rapeseed oil CH3 242 Rice bran oil CH3 za 8 = 193-210 / 0.05 243 ', Chrysalis oil CH3 C' a 8 188-214 / 0.06, 244! Sunflower oil ; C113 e; 8 '119 3 / 0.061 245 Huïle cï.e pleuronecte Ch 3 D 8 39G-22Ci 0.05i 2L6 Hhile àa liver de 1 (246' Oil shark liver CE- '' 187-209 / 0.06!: Shark cïe fo .e CH3; a 10 '187-209 / 0.06.



  247 Whale oil CEL E a 10 187-2G''CJJo, 05 24-8 Cuttlefish oil CH- 3 at. a j 8 193-2.8, IJ, 36! z 'Sardine oil CH- B b 20 201-219 / 0.06 2% 9 SardoEe oil 3! t 250 1 Mackerel oil CE F i a! i 200-218 / 0.05 Oil ce "* 3 1fez! 251 Scombrêsoce oil! C2115 c! 187-217 / 0.06i: 252 Herring oil OE3 d! -10; 185-215 / 0.051 252 Oil, hoeve % OE 185-2l5 / 0 253 Saurel oil CH3 a 10! 184-212 / 0.05} z Oil: .3e nenüadea CH3 a 10 1 .82-222i0,08

  <Desc / Clms Page number 65>

 
 EMI65.1
 255;

   Oil It! : 8! 190-218 / 0.05 255 -Norue liver oil, i 190-218 / 0.051 256! Liver oil CE 3 D f 12) l89-217 / 0.06! 257 1 Residual oil CII 3 A to 8! 184-221 / 0.08; z Hail of menuse CE A e 8 j 1'75-220 / 0.08i 259: Safflower oil i c3H 12 199-211 / 0.041 ------------------- ---------- ¯-: ¯ ---------------- ¯L --- ¯1

  <Desc / Clms Page number 66>

 Example 260
For 30 hours, a mixture of 10 g of methyl linoleate and 6 g of methyl linoleate was heated at 180 ° C. in a nitrogen atmosphere.
 EMI66.1
 (+) o {-methyl ... benz, ylamine, while excluding, from the reaction system, the methanol formed as sulfur. After the reaction, the reaction mixture was distilled to obtain 12.3 g of a product.
 EMI66.2
 desired result of a P.E. of 202-215OC / 0.05 nm of Hg. L 5 + 59.5.



  Elemental analysis:
 EMI66.3
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 61.40 <SEP> 81.62
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 10.77 <SEP> 10.85
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.46
 <tb>
 Example 261
A mixture of 10 g of methyl isostearate was reacted,
 EMI66.4
 5 g of (+) o (.. 1Ilthyl-boIlzy: 1.Drl1nO ot 1 3 of l1lét.hy: to.to of sodium, at 15000 for 3 bc ,, - tos on c: c.uu: r, From the reaction system, the methanol formed as a by-product. The reaction mixture was washed with acid, alkali and water according to the usual methods, then dried and distilled, to give 12, 3 g of a desired product with a PE of 207-220 C / 0.06 mm Hg.



  Elemental analysis:
 EMI66.5
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 80.56 <SEP> 80.49
 <tb>
 <tb> H <SEP> (%) <SEP> 11.70 <SEP> 11, ??
 <tb>
 <tb> N <SEP> (%) <SEP> 3.61 <SEP> 3.81
 <tb>
   Example 262
To a mixture of 10 g of ethyl oleate and 5 g of (+) [alpha] - methyl-benzylamine was added a solution of 0.5 g of sodium in 8 ml of ethyl alcohol. reacts the mixture at 160 C for about 2 hours removing ethyl alcohol. Then, the same treatments were carried out as those described in example

  <Desc / Clms Page number 67>

 261, to obtain 12.0 g of a desired product with a P.E. of 208-219 C / 0.06 mm Hg.



  Elemental analysis:
 EMI67.1
 
 <tb> Theoretical <SEP> Analytics
 <tb> C <SEP> (%) <SEP> 80.98 <SEP> 80.88
 <tb>
 <tb> H <SEP> (%) <SEP> 11.24 <SEP> 11.17
 <tb>
 <tb> N <SEP> (%) <SEP> 3.63 <SEP> 3.81
 <tb>
 Example 263
For 12 hours, a mixture of 10 g of carthamo oil and 6 g of (+) [alpha] -methyl-bonzylamino was heated at 200 ° C. in an autoclave, then it was distilled. immediately, to obtain 13.0 g of a desired product with a P.E. of 197-220 C / 0.05 mm Hg.



   Examples 264 to 296 are shown in the following table.

  <Desc / Clms Page number 68>

 
 EMI68.1
 



  RCONEC31, F% 1 \.! 0 Ru le = Cl x Rn in = C05 L N
 EMI68.2
 ; ¯¯; femp- Duration. 1j z, .¯¯ C% 3% N 9â 71J; Ester Example, erasure 'de la Cata- soi-1 P.E. ..



  No or Rlu of reli of the; reaction t 1 wind lyser 1 0 1 ------- 1 ---------'-----------; glyceride:; ference; reaction,; "C / Hg Theo- i.na.1y-1 yi Theo-i.: .. nal7-! (OC) i (hours) Il rique = tique 'rique tique 1 riquej tique Il! ¯¯¯ -.:64 '. Li.! T::. T!; I, 264 ′ Linoleate -!, Methyl o 263 200 ′ 200 -211 / 0.04 81.40 81.59 ′ 10 7; 20.91 3, 65 3.44 Ethyl 263 200! ;; 200-211 / 0.04; 81.40 81.59 '10.77; 10.91: 3.65 3.44' -1-65! Linoleate: ethyl ioc ^ 60 180 48 i 201-209 / 0.05. 81.40 81,%; 10.77 10.88. 3.65 3.33.



  266'Keyedem- i 2exil It! '! 1 f 21.44 1! thyle: 0 261 160 4 1 KOt; Bu! <204-221 / 0.06: i 80.98 81.20 il 11.24 f: 1.1.44 3.63. 3.42 28i 262,160 Na isostearate; CH3oe;: 206-219 / 0.07i $ 80 77 11.70 11.98 1 3; 4-7.i methyl 101 262 160 1 NaOCJI3 CH30H! 206-219 / 0.07! 80.56 80.77% II, 70 11.98% 3.61 3; - ?: 288; 1 inethyl olenate o 263 200 '205-218 / 0.05! 81.83 81.88 1 lU ,, r'5 3 s6'7 t 3, l; imethyl 263,200 '205 -218 / 0.051 81.83 81.88 10,, 30 10.55 3 at p: 269r Raethyl ester 263,200! 81., 83 81.88 10.30 j 3 ':. 1' ....



  269 ethyl ester of icarthane oil 26-e 200 198-209 / 0.0511 2fi0; Ester uet3yli 4- f ..... "Rj 'oil of 263,200 d;' 198-2Ilf .. 'ssôsame': oil 263,200 12! L98-211 / 0.05; 271;! Detethyl ester -!
 EMI68.3
 
 <tb>: that <SEP> of oil <SEP> of
 <tb>
 
 EMI68.4
 .ricin 260 180 1199-215 / 0.051. castor 0 260 180 42 199-215 / 0.05 '

  <Desc / Clms Page number 69>

 
 EMI69.1
 272tMethyl ester / 0. ' -: rapeseed oil 1: Ji: 28ü 180 40 J 201-220 / 0.06!
 EMI69.2
 
 <tb> 273 <SEP>: Ester <SEP> methyl <SEP>
 <tb>
 
 EMI69.3
 -Olive oil 0.150 x -NaO CH3i i88-2o9 / 0.05 274 'Methyl ester 1.261 fi 150 i 188-209 / 0.05 Bran oil from ..' = 2? 5;

   Nethyl ester! j 0 263 190 10 f '! ! i89-2ivo, 05
 EMI69.4
 
 <tb>: '275'Ester <SEP> methyl
 <tb>
 
 EMI69.5
 cottonseed oil x 260; tRn 193-208 / 0.05i; 2'76 Methyl ester; ±: f! 260 180 38 f 193-208 / 0.05: id of ebr7salid oil Cl'1. "" "Ysa-260 80 - f! Î 193-212 / 0.061 'J' -277 Esternethyl 260 180 d -153-212 / 0.061 2771 Methyl ester 180 of sardine oil 260 180; 87-215 / 005) .2v8, methyl ester 2781 Net ester:? Jylic 260 180 1. of fish oil 260 180 42: 87 -8 / 0.05}; 279; Esternetbyl oil of pleuro- If !!! Inocte of picuro- oil '260! No; 197-223 / 0.051 f inects 260 180 il97-223 / 0 051; 280 safflower oil 263 19, D 20 990/0 05! 1,280 Linseed oil trI "1 263 190 lS9-210 / 0'05 i 2811 Linseed oil 1 0 d 263 fi 190 18 1187-21610.06 282 3rd o 263 oil 190196-21106;

   2821 Soybean oil 0 263 190 1 18 If 1 il96-217 / oo6i 283 Sunflower oil! 0 263 j 200 12! L94-212 / 006! 284 Corn oil 200 I2 95-213lez i 2841 Liver oil 263 200 195-213 / 0.07, 285 Liver oil # 263 100 12 "184-216 / 0.07 / Î shark 263 6/0, (ï,. ¯.¯¯ #### ¯¯ ########

  <Desc / Clms Page number 70>

 
 EMI70.1
 
 <tb>, <SEP>) <SEP> 286 <SEP>) <SEP>; <SEP> Oil <SEP> of <SEP> cuttlefish <SEP> o <SEP> 263 <SEP> 180 <SEP> 16 <SEP> 189-217 / 0.07
 <tb>
 
 EMI70.2
 287 * Sardine oil 1 µ o 263 190 14 i 191-213 / 0.07
 EMI70.3
 
 <tb> 288 <SEP> Oil <SEP> of <SEP> mackerel <SEP> o <SEP> 263 <SEP> 190 <SEP> 15 <SEP> 193-209 / 0.06
 <tb>
 
 EMI70.4
 ; 269 Sconbrésoce oil = o 263 j 200 12 i 191c..213 / 0.05! : 290: Herring oil 0 263. 200 12 196-213 / 0! '291;

   Saurel Oil o 263 200 12 -'-. lbFr-2./O:(ü = 292 Pleuronectus oil / o 26 190 12, 135-217 / 0.05 '' 9f Jacn oil. a -. a o 263 190 14 G4
 EMI70.5
 
 <tb> 294 <SEP> Oil <SEP> of <SEP> liver <SEP> o <SEP> 263 <SEP> 190 <SEP> 12 <SEP> 193-200 / 0.06
 <tb> 295 <SEP> Oil <SEP> residual <SEP> o <SEP> 263 <SEP> 190 <SEP> @ <SEP> 16 <SEP> 188-218 / 0.07
 <tb>
 
 EMI70.6
 296 Carthara oil i 263 200 18 1 2pC-910.02 (R- = c) <R;

  x = c 3,> j j

  <Desc / Clms Page number 71>

   Example 297
Individually 10 g of linoleic acid, 5 g
 EMI71.1
 do d (* o (-thyl-bcnzylamine and 10 ml of d1oc1hexy1-carbod11mio in 50 ml of toluene. The solutions were mixed together once and the mixto solution was allowed to stand at room temperature for 8 hours. After filtering the solution, the filtrate was washed with acid, alkali and water, then dried, concentrated and distilled, to obtain 11.1 g of a product.
 EMI71.2
 desired result of a Bzz. do 201-209 a / 0.04 µm of Es.



  Elemental analysis:
 EMI71.3
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.40 <SEP> $ 81.66
 <tb>
 <tb> H <SEP> (%) <SEP> 10.77 <SEP> $ 10.91
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.42
 <tb>
 Examples 298 to 332 are shown in the following table.

  <Desc / Clms Page number 72>

 
 EMI72.1
 d- 1 pun
 EMI72.2
 ¯¯17 JQ "'f.'" ..-.....- 1 "" ------ ........ ¯ --- -......... .



  > E: x: em-! i [kdne 1 'BN = C = NB 1 1 g p.E. : / '1 i fiJ i .u jD no F 8 "" B fl Solvent C / nm Hg. Theo- Analy-. Theo-:;. Na1y- Theo-; .Ana1.7- .¯¯¯¯; ¯¯¯¯¯¯¯ ¯¯¯? 1 bzz bzz-. tick tick: tick 'tick tick' "" #############.



  '! '-. ! -. ''. ':! j 298 "" ide linoleic CH3 D! Ether 200-209 / 0.04 81.40: 81.67! 10.77! 10.93 3.65: / 3 '44 II. 299 'linoleic acid CB D ",' Dioxane 201-209 / 0.04. I. ' 81.40. 81.68; '' 10.77; 10.91 3.65 3.33! 299 Linoleic Oyeµ Dîoxanne 2Ol-209 / O C4 / 81 40 '/ 81 68' J 91: 300 Oleic acid C $ 3 r¯ \ ¯i.

   Dioxane 203-209 / 0.06! f 80 98 81.05 it! 5.63 J 3.48! 300 Oleic acid; ! CE i CB CB #! Dioxane j; 203-209 / 0.06; J! :;! j 80.98 ff fi: l1.24 U 44 i 3.63 3 48 #v 301 Linolenic acid! C'H3 to Tetrahydro-211J0.05) 81.83 '' 82.05 10.30; / io, 65 / 3.67 3.4g 302 Isostearic acid j CH - / "'\ # Ether, 203-214 / 0? 80, 56 8C,' J2 ll '70 Ô 11.97! 1 ô' 61 3.51 302 J..isostearic acid oe); Ether / 2oo-214/0 80.56:

   E0.88 11.70 j 11., 97 O;, 61 f 3.51 1: 303 Isostearic acid f CH. 3 ¯¯ Toluene, 200-ü4 / 0.0 $ 80s56 $ Oa88 11.70, J. 11.87 3.61 3.49: 303 f I.k.cida isostearic CH3 ID; Toluene f; 200-214 / 0.0511 80.56 'f' J 80.88 1 f 11.70! 11.87 j 3.61 3.49 I. 305 f J 1 Soybean oil: '. <: I3 9 - # rirl -------- i ----- l ---- l-l-l ---

  <Desc / Clms Page number 73>

 
 EMI73.1
 306 Sesame oil 41 Cff3 D j Toluene 189-216j0.07 =: 3d? Castor oil JI Tëtrachlo- Ig2-21'319.0? : ride de j / carbon ± carbon 308 Rapeseed oil. OE3 Benzene ZQ.-217., J0, C'6 309 Olive oil;. C2H5 Pyr: idJ ne I9o-2z5r: 0 thread 310 Rice bran oil CiI3 '0. B <.-> nzàne 3ti5¯ß: .j. / OS 311 Cotton oil CH 3 Toluene 193-21 .5 / 0.0.5, Cotton oil CH3 To1uèno - 193-215 / 0.05, Oil nais 312 DaiS oil 30 .

   T01u9! Le 3 / 'S 313 Peanut oil j CI3 D Ether lg¯g / pp6 314 Olive oil CH3 D 1 Toluene 1gI-219 / D, 06 J15 Chrysalis oil Toluene i9o-a5 / o, 05 316 Liver oil of CH3 Benz4ne 204-2MO, C5 1 16 Liver oil of 1 CJI Benzene, 0'05 --- -----------..---------- ..... ------ ... -4¯-¯1> .. 1. --- ,, 1. -. "" "----......

  <Desc / Clms Page number 74>

 
 EMI74.1
 



  317 'Cuttlefish oil Î' t CH3 D! ' Toluene 1'19-225 / 0.051'318 Sardine oil; EC 3-0: Ether 190-220 / 0.07: '319 Mackerel oil CH3 1 D -Ether 192-215I0.05; 320 Scombrésoce oil 'CH3! .. Benzene Ig0-21w / O, pE,; ! 321 Herring C-Ti 3 to -0! Ether j 191-2t / 7, U5; 322 Saurel oil, CH -C \ Toluene:! 181-219 / 0.05 '322 Saurel oil CH3 D Toluene 181-21910.05 j j 323; : Liver oil from i CH3 .0 Chlorofomol 185-.220J0,05; cod. Liver Chloro.fo:rne 185-210 / 0.05 cod z Trout oil fi CE- D Î Té1; rabydro-! 180-21.9 /, o, 05 32+) Oil% list 1 OEj furan 18 -219 / O ¯1 325 # Oil r.u3..et ft "uran 325 Mullet oil CH 3" 0 Tet 191-225 / 0.05) t 1 --- 'furan j -5 / 5 t 326 1 Menuse oil'; CH3;

   If Toluene i 187-215 / 0.06 1 327 '* Menhaden oil J 1 CZI5! f Dl Dioxane, / 195 - z25 / o '05 jL¯¯J! ¯¯¯¯¯¯¯¯¯¯J

  <Desc / Clms Page number 75>

 
 EMI75.1
 ! 328 'Eel oil CE 3 -0! Benzene 3 196-220 / 0.05 i:;., 1 ..



  329! Pleuronectus oil 'CH3 -0 j 187- 22r ,, / 0.05 329! Depleuronecte oil CH3 '\ i 1 Dioxane 18? -22G / 0.05 330' Whale oil OE3 Benzene i: 175-21910.06! J 3! -.



  331 = Liver oil C;! I - / "\ Í Toluene 1'-219 / (J .07.



  331; Liver oil 3: \. # / 'Lek-? 332 Residual oil r; r ^, 191-22 f 332; . Residual oil C2 H5 il V! rvluà .... o 191 - 2-D CC,! i ¯¯¯¯¯¯¯¯¯j¯¯¯¯L -.-. # .- # L # ..-..- .. #. L # ¯¯¯¯¯¯¯L

  <Desc / Clms Page number 76>

 Example 333
 EMI76.1
 To a solution of 12.5 g e.o (+ (7-methyl-bonzyl, amino ot 8 g of trimethylamine in 100 ml of anhydrous ether was added 30 g of linoleic acid chloride in 50 ml of Anhydrous ethor, while stirring at 0-5 C. After the addition, the reaction mixture was boiled for 2 hours to complete the reaction, then the ethereal solution was washed with an acid. , alkali and water, then dried, concentrated and distilled to obtain 42 g of a desired product of a PE of 207-217 C / 0.05 mm Hg.



  Elemental analysis:
 EMI76.2
 
 <tb> Theo <SEP> laughed <SEP> that, <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.46 <SEP> 81.58
 <tb>
 <tb>
 <tb> he <SEP> (%) <SEP> 10.77 <SEP> 10.91
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.41
 <tb>
   Examples 334 to 369 are unfair in the following table.

  <Desc / Clms Page number 77>

 
 EMI77.1
 o -Métbyl-benz, ylanine xc {-E1ihy1.-benzyl # nne + o (-Propyl-benzy1.amine Õt-Butyl-'benzyZanine .. ¯ '\. ¯ ------------ ----- ¯.¯-
 EMI77.2
 1 1 '' '1 a% J E% 1 N% Acid halide Solvent Agent ,, 7D! lU, r "Acid halide f RCCV 1 X; Sol Agent FE --------------! z -------! Ple acid RCCX! 1 Solvent condensation. OC / lm Hg 1 Thàol 'Analy-! Theo- 1 "--1.

   Tea '"-al ..¯¯¯: ¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯; ¯¯i ¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯; j ric tic ric; tic ric tic 334 .Oleic acid 0 -! Cl acetone i 1, C03!; 205-217 / 0.051, 80.98 81.11 i Il) 24; .. Il, 41! 3.63 3, 91 335 Oleic acid o! Cl rTétrabydro- Na0E 207-216 / 0.05 8C 98 81.09 Il, 4l1l, 35 3963 3.66 tj iunring '*' '336 Isostearic acid, fol Cl!; Ether J Trinethyl- 2 <6-218 / 0.06J 80.56 80, '17 11.70! ll, 91 3.61 '3.42 336 d Isosteanic acid o) Cl Ether amine 1 <Z-z18 / 0.061 '] & 0.56 j 1 80,' / 7/1 11 '70 [1 11' 91 ') 337 J Isostearic acid o! CI 'Toluene Pyridine 203-214 / 0.05' 80.56 i 80.72 11.70 11.89 3.61 3 48 Isostearic acid TOluene! Pjr: i.dinc 203--21LI- / fJ: 05 80.56 80.72 11.70 Il, 89) 61 3.48 338 Linoleic acid fol Cl Acetone Picoline l:

   ZOO-215/5, <J5! 81.40 i 81.62 lO '7? ) 10.81 3 '65 J' 62 339! Linoleic acid or ciitethyl- 1 Toeiémnyl- '20C-: 2lÓIC'1.05 81.40 81.70 10.77! 1C, 94 3 65 3933 butyl # amine j !, t -t 'te6toue amine 340 Linolenic acid Cl. Ether Triethyl- 201-217 / 0.05 81.83 81.93 10 3o 1 iO 5W 3 67 J 4 #' 340; Linolenic acid Amino ether 81.93 10.30! 10.5! I- 3.67 '"' \ ... i <azine .... 1341 Linolenic acid) Cl -, Benzene Dinethyl- 05-215 / 0.04 81.83 81.95 10.30 10.63 3.671 3, t.
 EMI77.3
 
 <tb>



  ,aniline
 <tb>
 
 EMI77.4
 342. Oil acid of x Cl 1 Dioxmme / KOR 198-208 / 0.05 carthane water.



  343 Oil acid j Cl Acetone / KàW3 j soybean oil! ! water K2C03 195-2l0 / 0, O6! 344 Oil acid 0 Cl Ether Pyridine t 344 Sesame oil Ether Pyridino 198-21110.061 '

  <Desc / Clms Page number 78>

 
 EMI78.1
 ######. ################## ..



  ! '345 Castor oil 0 ClEther * Ether l'yrîèl 1 n 193-216 / OtC4 346 Rapeseed oil oi ClJEther Qyridine 201-222 / 0.06 347 olive pulp x Cl Toluene i 1 T' 'thyl j 188- 213 / 0.05 348 Rice bran oil; o Cl i Toluene Tniétbyl 187-213 / 0.06 Rice bran oil CI with anine 187--213 / 0.06
 EMI78.2
 
 <tb> 349 <SEP> Oil <SEP> of <SEP> cotton <SEP> o <SEP> Cl <SEP> Benzene <SEP> Pyridine <SEP> 194-218 / 0.05
 <tb> 350 <SEP>: <SEP>; <SEP> Oil <SEP> of <SEP> chrysalis <SEP>; <SEP> o <SEP> Cl <SEP> Toluene <SEP> Pyridine <SEP> 190-214 / 0.06 <SEP>
 <tb>
 
 EMI78.3
 551 Corn oil C1 cetane / water 1 "NaOH;

   203-2? ./ 0.08 352 Linseed oil Cl Ether i Pyridir8 lS0-215 / O 06
 EMI78.4
 
 <tb> 353 <SEP> Oil <SEP> of <SEP> sunflower <SEP> o <SEP> Cl <SEP> Tetrahydro- <SEP> NaCH <SEP> 195-212 / 0.05
 <tb> furan / water <SEP> '' '0'5
 <tb>
 
 EMI78.5
 354 Pleuronectus oil o Cl M é'1- F E: 2CO3 188-214 / OeO4
 EMI78.6
 
 <tb>) <SEP> butylacetone
 <tb> 355 <SEP> Oil <SEP> of <SEP> liver <SEP> of <SEP> Cl <SEP> Acetone / <SEP> 183-218 / 0.04
 <tb> shark <SEP> water
 <tb>
 
 EMI78.7
 356 Whale oil Cl! Acetone / ia2C0 bzz water 357 ± Cuttlefish oil ci Dioxane / NAOU 180-214 / 0.05) 557 Cuttlefish water NaoH 18o-214 / o bzz Sardine oil! Cï 1 1 Oxam /:

   R200 190-213 / 0.05 -water. ###. '' "'" ############### -

  <Desc / Clms Page number 79>

 
 EMI79.1
 359 Raquerel oil - -o - ### - # Pyric'üne- '192-211 / 0.05; 359 Naquerel oil o Cl! Toluene Pyridine 192-211 / 0.05 360 Scombrésocef o Cil f Dioxane / NaOH! 190-210 / 0.05
 EMI79.2
 
 <tb>, water
 <tb>
 
 EMI79.3
 j 361 Herring oil 0 t; C1.

   Toluene Pyridine f 193-214 / 0.05 1,362 'Saurel oil' 0 Cil J Acetone / 1 NaOH 1,183-219 / 0.05 363 'Aehhaden oil 0 Cl! Toluene Pyridine! 193-223 / 0.05 364 Liver oil reads! i EOH 1 185-209 / 0.05 364! Liver oil o j Acetone / KOH 186 = 2C9 / 0.05 j norue! water, i 365 / Liver oil x Cl Ether P3ridine 190-214 / 0.04 d 366 Residual oil CI law Acetone! 'KOH; 187-2l9 / 0, OG
 EMI79.4
 
 <tb> water! <SEP>
 <tb>
 
 EMI79.5
 , 367; Nenuse oil o Cl! Acetone / i NllCH 138-208 / 0.06 1 368 1 Carthano oil 1 Cl Acetone / d 1 NaOH 1 193-206 / 0.06 l! 369! :

   Carthane oil t Cl Acetone /! NaOH 197-211 / 0.08
 EMI79.6
 
 <tb> 1 <SEP> water <SEP>
 <tb>
 
 EMI79.7
 ------------------------ 1 --------- Î -------- L ------ -1 ------------ <L

  <Desc / Clms Page number 80>

 Example 370
Laying 24 hours, we heated to 180 C, a mixture of 10 g
 EMI80.1
 of linolenic acid and 6 g of d (+) / -methyl.-bonzylamino by removing water from the reaction system during the reaction.



  After the reaction, the reaction mixture was immediately distilled to afford 11.3 g of a desired product with a m.p. of 203-221 C / 0.07 mm Hg.



  Elemental analysis:
 EMI80.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.40 <SEP> 81.66
 <tb>
 <tb> H <SEP> (%) <SEP> 10.77 <SEP> 10.90
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.42
 <tb>
 Examples 371 to 396 are +; indicated in the following table.

  <Desc / Clms Page number 81>

 
 EMI81.1
 



  RCONBCH a - '. CII 1 N. =: F 8 "C $ 7C 2 5 Kidney
 EMI81.2
 Exem-i z ¯ ¯.r. ¯ ¯ Duration -¯ - ". W.



  . '1:' ... m-ll r '"" re Duration, N%) Pl rature of the P; ¯ ¯ ¯ ¯; deny- 1 ¯id T! "" 'f) o1! - i .. <e Acid 8 ""; of the ! reaction '0 C / mm TT¯ # -' ## '"-' #### - ### .- t ############### ###### ##### ....., * N aa 1 é ti! 1 Théo-, naly- Théo- r 1 é ti! EI! Lf 1In. ' ., 1. Nn..é. 1 1. I "'- éo 1 al (C) eur s: rique tique, riquotique, riquej tique - - ------ ------- --- 1 ------ ------- ------ ric t-î-que rique tique rique; tick 3'71 Isostearic acid o! 180 24 205-218 / 0.06: 30:56 '80.77 11.70 11.97 3.5. z, 372 .t \. 1 oleic acid 0 180 24 205-217 / 005 s b0, g8 81.30 11.24 11.63 3.65! 3.29 373 1.tÍ linolenic acid) j 0 180 24 20S-21C / 0, C6 81.83 81.96 10.30 10.61 3.67 3.38 bzz. Oil acid of o in 24 'n5-219 / 0.07! 3'14: i .. oil acid 'o'! .: 180 IS5-2l9 / 0,07 i carthana '"" -' "375 1 Oil acid of, .. 0:

   . 200 F- 198-221jO, a5! Soybean oil 200 'j 198-.221 / 0.05 375? Today: ade o! 180 d 194-209 / 0.06 3'1! i üCi.de d1C411 .a. of o. 180 20 194-209 / 0.06 *,!
 EMI81.3
 
 <tb> 'but
 <tb>
 
 EMI81.4
 J: oil leaves z24 Iii 377 f 4 oil acid 180 24 196-213 / 0.05 cotton 378 l cotton oil or 160 36 198-206 / 0.04 3'18 sesame oil 160 198-206 / 0.04 379 Oil acid of or 160 36 200-221 / 0.04 {3'79 castor oil 160 36! 200-221 / 0.04
 EMI81.5
 
 <tb> castor
 <tb>
 
 EMI81.6
 380 Oil acid; 0 180 24 188-211 / 0.06 380 -olive 180 188-211 / 006 wire j

  <Desc / Clms Page number 82>

 
 EMI82.1
 z Oil of o 180 24:

   200-2I6 / 4.05. ßcolza. 382 halle ide of 180 193-211 / 0.06 'sunflower 383 oil acid of 1 o 180 24. $ 8 -216 / 0.05
 EMI82.2
 
 <tb> 384 <SEP> Acid <SEP> of oil <SEP> of <SEP> o <SEP> 180 <SEP> 24 <SEP> 189-215 / 0.07
 <tb> 'sound <SEP> of <SEP> rice
 <tb>
 
 EMI82.3
 z 2> x 18C 24 18% -22G / 2,5fl oil cide
 EMI82.4
 
 <tb> liver <SEP> of <SEP> shark
 <tb> 386 <SEP> to acid <SEP> of oil <SEP> of <SEP> o <SEP> 180 <SEP> 26 <SEP> 172-223 / 0.04
 <tb> whale
 <tb>
 
 EMI82.5
 387 j Oil acid of ou 10 24 193-05 / 0.0 !: 5! LaQ9 <rQau naquercau
 EMI82.6
 
 <tb>: <SEP> 388-Acid <SEP> of oil <SEP> of <SEP> o <SEP> 180 <SEP> 24 <SEP>; <SEP> 189-216 / 0.07
 <tb> saurel
 <tb>
 
 EMI82.7
 339;

   = seichedhui2e de o J () 2W 18 185-3./G,06
 EMI82.8
 
 <tb> 390 <SEP> Acid <SEP> of oil <SEP> of <SEP> o <SEP> () 200 <SEP> 18 <SEP> 188-223 / 0.08
 <tb> liver <SEP> of <SEP> cod
 <tb>
 
 EMI82.9
 39l) Oil acid of or (") 210 18 193-21 / 0.0.
 EMI82.10
 
 <tb> herring
 <tb> 392 <SEP> Acid <SEP> of oil <SEP> of <SEP> 180 <SEP> 20 <SEP> 190-220 / 0.05
 <tb> sardine
 <tb>
 
 EMI82.11
 393 o 180 24 oil acid! 197-221 / 0.05
 EMI82.12
 
 <tb>! Pleuronect
 <tb>
   () In an autoclave

  <Desc / Clms Page number 83>

 
 EMI83.1
 ---- -------- - - -------- --- -----
 EMI83.2
 
 <tb> 394 <SEP> Acid <SEP> of oil <SEP> of <SEP> o <SEP> 180 <SEP> 24 <SEP> 190-218 / 0.06
 <tb> menhaden
 <tb> 395 <SEP> Acid <SEP> of oil <SEP> of <SEP> 180 <SEP> 20 <SEP> 193-220 / 0.05
 <tb>! liver
 <tb>
 
 EMI83.3
 396 1 oil cide res - o 180 2U 185-216 / 0.05)

   
 EMI83.4
 
 <tb> dual
 <tb>
 

  <Desc / Clms Page number 84>

 Example 397
Has a solution of 14 g of linoleic acid and 5.5 g of
 EMI84.1
 tr16thylanino in 100 ca3 of tetnhydnofunan, 5.9 g of ethyl chloroformate was added, while stirring at a temperature between -10 and -5 C. After the addition, stirring was continued. at -5 C for an additional 20 minutes. Then, while stirring at -5 ° C., 6.5 g of d (+) [alpha] -methyl-benzylamine were added dropwise. After the dropwise addition, the ice-water bath was removed and stirring continued until the temperature reached room temperature.

   Then, the temperature was gradually raised and stirring continued at 40 ° C. for 20 minutes. After cooling, the t-trahydrofuran was removed by distillation under reduced pressure and the residue dissolved in ether.



  The solution was washed with a cold dilute aqueous solution of hydrochloric acid, sodium carbonate and water and dried over anhydrous sodium carbonate. The ether was removed by distillation and the residue was distilled off in vacuo, to obtain 15.8 g of a desired product of PE of 202-207 C / 0.03 mm of Hg, [[alpha ]] D + 50, o.



     Elementary analysis
 EMI84.2
 
 <tb> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 81.40 <SEP> 81.72
 <tb>
 <tb> H <SEP> (%) <SEP> 10.77 <SEP> 10.89
 <tb>
 <tb> N <SEP> (%) <SEP> 3.65 <SEP> 3.42
 <tb>
 
In the same manner as in Example 397, 1 mole of each of the fatty acids and 1 - 1.1 moles each of the basic substances were individually dissolved in a solvent in an amount equal to 7 - 10 times the amount. amount of acid.

   To solutions, while stirring at a temperature between -5 and -10 C, we have

  <Desc / Clms Page number 85>

 
 EMI85.1
 Add dropwise to 1-1.1 moles of chloroform. After the addition, the mixtures were stirred at high temperature for 10 - 30 minutes. Then, while stirring, to the solution, 1 - 1.1 moles of each amino derivative were added dropwise.



  About 10 minutes after the addition, the reaction was completely complete. In some cases, the mixtures were optionally heated to 40-50 C. Then, the mixtures were treated according to the usual methods, to obtain, with yields of 40-85%, the compounds indicated in the Examples. 398 to 551 of the tables below.

  <Desc / Clms Page number 86>

 
 EMI86.1
 



  2O $ ww
 EMI86.2
 ; , ¯¯ j j p E 56 il # 1 N% Die: Acid Ruse P.E. ##########; #########; ####### j µf "" C / n11 $ g Theo- i .'lnaly- Thôll j IIÀÙ-1 ÎÀhéo- µ ànalyl .... ¯¯3 ¯ ..... ¯ ... r ..,. w¯ ..... ¯¯¯.¯.¯¯¯¯! bzz¯.¯.¯ rique; tick tick; tick creek {tick! i 'j - ------------ Î l) Î /) 398 Linoleic acid. ; d-CH - 201-209 / O, 04 81.40 to 81.66, 10.77 'loe95 3.65 3.58 399; Linoleic acid -t-m 3,200-209 / 0.04. 81.0 si, 58 10.77 '10.84: z 3.63 3400 oleic acid d-EO3 205-209 / 0.04. 80.98! = 81.04-11924 11.34! 3s63 3.58; i 4oZ Linolenic acid a-cH3 205-213 / 0.05 81.83 82.03 10.30 10.35 .3.67 3.47 s 402 1 1 atciâe isostearic d-CS,)) 205-2l3 / O 05 80.56 fez 11.70) lO 35 3.61) 3 '4? 403:

   Isostearic acid d-CH3 202-2l4 / O, O? j 8O, 56) 80.62 ll, 70 11.91 3.61 3.52 403 Isostearic acid fl-cH 203-? a.3j4, ü5 ¯ 80.56 80.73 11.7o ii, eg 3.61 3a '/' + Calta-d-Cë oil. 5 199-213 / 0.03 405 Soybean oil, -4H3 193-215 / 0.04 4O5 Soybean oil (cEs j 19> a5 / o, c4) 4O6 Sesame oil d-CH3 188-2l4 / 0.07 407 Castor oil d-CH3 194-211 / 0.07 4? ) Hùiie "in d-" 3 19 + -2ll /, 7 i 408 Rapeseed oil yc-CH 190-210 / 0.06 Ô ----- Ù ------------- -to ------ L ----------- 1 ---------- É ---- 1 ----- É ------- ---at

  <Desc / Clms Page number 87>

 
 EMI87.1
 
 <tb> ----------------------------------------------- -------------
 <tb>
 
 EMI87.2
 409 Olive oil d-C 2H5, 193-215 / 0.06
 EMI87.3
 
 <tb> 410 <SEP> Oil <SEP> of <SEP> sound <SEP> of <SEP> rice <SEP> l-CH3 <SEP> 185-210 / 0.06
 <tb> 411 <SEP> Oil <SEP> of <SEP> cotton <SEP> d-CH3 <SEP> 195-214 / 0,

  05
 <tb>
 
 EMI87.4
 ! 412 Maize oil a-cH3 1 191-2i8 / o, o5.
 EMI87.5
 
 <tb>



  413 <SEP> Oil Peanut <SEP> <SEP> d-CH3 <SEP> 193-217 / 0.06
 <tb> 414 <SEP> Oil Olive <SEP> <SEP> d-CH3 <SEP> 191-209 / 0.06
 <tb> 415 <SEP> Oil <SEP> of <SEP> chrysalis <SEP> d-CH3 <SEP> 198-215 / 0.04
 <tb> 416 <SEP> Oil <SEP> of <SEP> liver <SEP> of <SEP> shark <SEP> d-CH <SEP> 202-222 / 0.04
 <tb> 417 <SEP> Oil <SEP> of <SEP> cuttlefish <SEP> d-CH3 <SEP> 178-225 / 0.04
 <tb> 418 <SEP> Oil <SEP> of <SEP> sardine <SEP> d-CH3 <SEP> 194-222 / 0.06
 <tb> 419 <SEP> Oil <SEP> of <SEP> mackerel <SEP> l-CH3 <SEP> 191-214 / 0.05
 <tb>
 
 EMI87.6
 420 Scombrésoce Oil 3 ZWOO5
 EMI87.7
 
 <tb> 421 <SEP> Oil <SEP> of <SEP> herring <SEP> d-CH3 <SEP> 191-218 / 0.05
 <tb> 422 <SEP> Oil <SEP> of <SEP> saurel <SEP> d-CH3 <SEP> 184-219 / 0.05
 <tb>
 
 EMI87.8
 42 3 Cod liver oil - (3 1855-214 / 0,

  05
 EMI87.9
 
 <tb> ----------------------------------------------- -------------
 <tb>
 

  <Desc / Clms Page number 88>

 
 EMI88.1
 j j 1 4z # P j Trout oil J CH.3! 180-218 / 0.05 - 1 425 Olet oil d-CH3 193-225 / 0.04)) Menuse oil d-CH 3 189-215 / 0.05 t 42 Nenhaden oil, C2H5 193-225 / 0.05 f [4z8 Eel rail 1 d-CH; 195-219 / 0.05 3 t 429 Pleuronectus oil E ..e - (: 33 or: L88-22J /, 05 i 430 Huilc- do baloînc ',, - 3 "'? - 431 Liver oil 3 192 -211 / 0.05 431! Liver 192-2l ',' / O, 05 432 Residual oil d-czF5] 191-222 /> 8) L ---------- - --- ---- L

  <Desc / Clms Page number 89>

 
 EMI89.1
 11, C% fl% N9S PJ Amino Acid "C / na'Hg Theo-Anal7-.

   Théo- l.na1y- Théo- J] na17-t '1 1 rique tick tick tick ## - j j -----) <---- 'j ------ (---- 1--1 433 Linoleic acid F 202-212 / 0.04 J 81.55! 81, '70 10.90 11.0'7 3, e52 3.56 4Jµ, Lininoic acid; QzCH EH3 b - 1> 81.55 <81.0; 10.90 11.70.50) o.56,434 Linoleic acid 203..216 / 0.05 31.55 81.65 10.90 11.05; 3.52 3.64 434 1 1 linoleic ide NH2CH-d "t 203--216 / 0.05 1 j 81.55: 1 i 81.65 10.90 111.05!!! I 3, 52 31, 64 CH 3 '#:! JI l 435 àc 1 "noléiquP NEÉÉ ± # -cE 2gus ôî4% J 55> 9O) 52) 435 Linoleic acid 1 NH2CH (d) CH- 2Oe-214i, O l 81.55 81, 74 10.90 11.08 3.52 3.72] CH 3! CH3 436! [Linoleic acid 1 GH-O 199-216 / 0.05 81.69 81.87;

   11.02 1?., 48 3.40 3940 6A llzl) 1419 III! 4? Ac1.de liDo1é1.que 1- 1 22O-22 / 0.08 14.69? 4, 'l? 9.65! 9.71, 51, 48 437 Linoleic acid NH # - 220-223 / 0.03 74.69 74.77 9.65 9171 3.35 3.48 \ == / to Il !! i 1

  <Desc / Clms Page number 90>

 
 EMI90.1
 bzz - ¯. '1 ¯.n ----- 7 ------ .. t Í r & 1: t 1, - t --1 438! Linoleic acid NH2CH I 1 222-224 / 0.07 d 74.69? 4.82 d 9.65 9.75 3.35 3.37 1 4} 8! .:. amino acid xqzrd Q fi 222- * </O> 07) t 14.69 74.82)! 9.651 9.1: S: s.: S5! : S,: S1 Ô i; r i + 1439: Linoleic acid rCH 1 i / 1 22 -226 /, 8) 74.69 74.58 9.65 91196! 3.35 3, <9 d 44o iào iinoiéiqae m% cHggpci 1 / ci zz>? </ o, 08 69, oi j 69.9O j 8.69 8,? 9 3.1, 3.3.



  440! Linoleic acid! ': 1CH. Cl. I ê25-40 / 0.08 69.01 69.90. 8 ', 691 8.79 j 3.10 3.32 j' CE- 3 QÙ), jj Ù) 441 Linclean acid j% pÔBl) "2'5.-23 /, 2 É?, 5 67.66 8 , 72! 8.76 3.03 3.27 441 If 1,! 1 Linoleic acid L 1 1 ', 225-2;> 4 / 0.2 I! F!;. 67.52 t j- t! 61.66 8.12 j Í '8,76 Ii i,! 1 1: S, O: S t ": S, 21 442 Linoleic acid NH2CH / 223-238 / 0.1! 67.52 1 67'5411 8.72 su bzz 3.08 3 d 443 Linoleic acid t 8.82 j 3.19 'f' 443. Linoleic acid t # Ó 224-2% / 0.1 1 6'7.52 61,681 8,121 8,82 3,031 3.19 443 Acid i "iéiU en, '- * /)'? L 0 '?" '); . '¯¯ .¯¯¯, ¯¯¯¯¯¯.¯¯¯¯¯¯¯¯¯¯¯¯.¯¯ ---. -. --- .--- ¯¯¯¯¯- ¯¯¯ ...., -... ¯¯ ..... r, .¯ ..,.

  <Desc / Clms Page number 91>

 
 EMI91.1
 



  "" #### "#" Y ### j ¯ ij 444 Linoleic acid NN 2 EC Br 218-237 / 0.09 = F 68.06 68.09 8.82 8184.9 3.05 445 Linoleic acid NHL [] <3210-224 / 04 '81.55 31.58 IC,' 3 / t la, 94 ¯; 3.52 / 1 d, 58 Cg 3 H5 1) 446 Linoloic acid 1 NH 21 N == /; / 1)? +, 69; ? 4,? 3) 9.65: 9.83 3.55 5.50) 447 Linoleic acid NH (d) CH-n \ -ci 217-226 / 0.08 i '? 4.69' 74963 9.65 Il 9, 70 3.35 3.25 CH3 I 448 Linoleic acid i 2 CH 220-223 / 0.09 78.40 78.29 10.48 1d.34 3.39 3.38 3 id uxzoed '3 l zo9-n3 / o 09 7s, 4o 7s,> io, j in, 35) 3.59 3.29 z Linoleic acid iZH2ÇH, / \ 209-223 / 0.09 78.40 78.38 10.48 3.4.33 3.39 3.29 cHr --L ## - J-¯¯ ## - ¯¯¯L¯¯ - #### ..-. ## - ##

  <Desc / Clms Page number 92>

 
 EMI92.1
 ¯'l'L¯¯¯¯-: ** r "* '*"' ": i; -!.



  450 Linoleic acid NHCH - ocH 218-223 / 0.1 78.40 - 78.57. 10.48: 10.37 s 3.39! 3.24 450 1 h linoleic NH2CH Cg I 1218-223 / 0.1. 78.40; 78.37 10.48 1. ': .-, 37! 3, G + 0 3 fi! .



  ; '451 j. Oleic acid 1 J "µ 212-222 / Q, C8' 81.29, 81.31; '11.45: ¯ 11,% 5 é' = 3; 39 i 451! Oleic ilcid; 1CH- o-C2H5 212-22210.08 i 81.29. 81.31 11.45 11.45 3:39 3.54 451 Oleic acid L.! 212-222 / 0.08 81.29 81.31 - 11, 45 11.45 3.39 '3.54! I 1' '' '' = '¯ li.S2 r, Oleic acid. I, HH2CH- (C - (2gs 212-223 / 0.09 81.44 <83., $ 6 .1.55 -U, 59 3.28 .'Ss $ 8,452 .Oleic acid? NHziH ± J-czH 25 * "! 212-22:) / 0.09 81.44 81.56 f À 1 11.59) i 3.28 j 3> * Cii5 ::. I fi µ / j 1 453 Oleic acid 1 NH2'G "H - Br 224-231 / 0.09 67.24: ii 67.3t j 9> 5 8, 4! 3.01 3.29 '1'! CH3 I fit i 1 45r + ¯ Isosteaxic acid NH2CH - CH i 202-217 / 0.08 ± 80,? 3 80.74 '± 11.83;

   12.9 '3.49 bzz 455! t Acid '' 3 EC 3 208-231 / 0.1 '81.33 j 1' '12.11 (! 12.22! 3.06'!! 3.18 455 Isostearic acid ÇH --- n-- l- # r 208-231 / 0,1! 81,33, 81,42 12, U i 12,22 ', 06 j 3918 Ji! ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ .¯¯¯¯¯¯¯¯ '.¯¯¯ 5¯¯¯ 3 ¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯ ... ¯¯¯¯ ¯¯¯¯¯ - .¯¯. ¯¯¯¯¯¯¯¯

  <Desc / Clms Page number 93>

 
 EMI93.1
 . !. ! t 1 1 "¯¯. ¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯" "" "7": '4 56 lcide i sOS'éar3.qt.e; :

   NH2CH-Q-Cl 221-228 / 0.09 Il 74.02 74.23: 10 a'4'3: 10:56 3.32 3 s'1 1 <- {3 f t t i 1) i 1 457 Acid isos1; éar1que! i 'NH2 ..' H - Br 3 223-21 / 0.1 66.95, 9, ';' 9> û Î 3 .: 3, Îkcià iSÔSfIÎIQÙ It! :?, ÙÙ) (9, Аk ¯ Î 9,% to / "), ÔÙ 1 µ 5, Ô 458 .. \ isostearic cide 1 î î i N1LCH CH, ft-oCH-x l! I 22C-22L; / 0.05 !, 6l> 7'l'64i, i 11.34 n, 45 Iii t. T 3.35 3.25 458 Isostearic acid CH / \ OCH3 i) 220-22 / 0.05 ?? a '':;? I. A-! A..i, 34 11a45. A35: = J 3,25 l 'il! F' 45g Isostearic acid i ± i:

   NH 2 CH 1 OC 2 5; 20-23C1t3, Og t -? 8'14 ': i? 8 a2l'! ' 11.53 III 459 Isostearic acid: N1I2FOOC2H5 220-2.3CIO, 09 t 78.24, 53 11.55 11! 3.14 3.09 bzz. 60 Iinolenic acid BE, H [J tC¯8. 220-237 / 0.08? 9, z; ? 9e73 10.18 zozo 3.29 3933 460. \ Amino acid '3 1220-237 / 0.081 79.61 79.13 10.18 \ 10.9> 3.29 \ 3.33 lit 461 llcide lina3.é tn..¯- ocg .o, m; 3au 461 Linolenic acid 1 CR, =, OCH3 (j. 215-z29 / o 1) 79 61) 79.77 lotis 10.32 é s, 29 l 3.40 ¯¯w.¯¯¯¯¯¯¯.¯¯..¯ ..¯..¯-¯¯¯¯¯¯¯¯¯¯..¯..¯¯¯¯¯.,. ¯.,. ¯..¯¯¯¯. '5 ¯¯¯¯¯¯¯,. ¯ ... ¯ ...,. ¯¯¯.¯.w: ¯¯ ¯¯ ... a ¯ .....: .......... ¯.r

  <Desc / Clms Page number 94>

 
 EMI94.1
 462! Linolenic acid f NH2CH 221-242 / 0.09 81.97! 82.04 10.45 10..65 3.54 3.48 462 Linolenic acid 221-242 / 0.09 81.97 82.04 10.45 10.65 EO3 463;

   Linolenic acid NHgCH CH, # ¯ i 21? -23F3 / U, 2 75.09: 25 19 9.14 1, / 2 '' ±, 36 3.37 '' 3 z! ' NH # - / - CS oil acid. ! : i 193 -.... "f'1 Ci! 0, lin biih3 ôH5 CH3 zi Oil acid of ii / S NE2CH \ 222-228 / 0.08] ± lin 3 L i 466 'Oil acid de -OE3 204-209 / 0.06 - Carthane GrH3 Oye3 467!! Oil acid from mcn- 3 203-212 / 0.06! 467 Oil acid 203-21.2 / 0.06 crrtharre:

   C 5 'Cg 3 = s ¯; '¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ...... ¯¯¯.¯ .. = .. ¯¯.¯¯¯.r¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯.¯ ... ¯¯.¯¯¯¯¯¯¯¯¯¯¯r ... ¯..¯ -. ¯.- ¯ ... ¯¯.-

  <Desc / Clms Page number 95>

 
 EMI95.1
 468 Oil acid of NH2CH zg¯g-2z9 / o, 06 '3 i 2Hs z Oil acid of BHCB -' Br 22--224% U, 1 carthane! \ == cantbane Cpb 1,470 NHCE oil acid - C-Hy; n9 "235/0, C6! soybean 471 j Oil acid NH2Cri 3 ± rFZ4C, / Ù, 05 bzz. sunflower cie -0 ('- 4R9 sunflower' =" 472. Oil icide OE-C% 1 21'7-221 / 0 906 472 Oil acid BCH - ci 217-227 / 0.06 Castor 1 = OE3 bzz * 3 bzz Oil acid from NH2CH --- OC2H $ 220-226 / 0.06 rapeseed 1, 3 (

  <Desc / Clms Page number 96>

 
 EMI96.1
 --....-. w..r.-..- ..



  4 '/ 4! Oil acid of NH.G "rI f çg3 22.-J - 229 / 0,0-5 cotton CC'OZ! 475! Acid of olive oil '21 Ô25 '' ''): 2Ii2-C2H 215-22? /, TT '== "4'76 Oil acid% CI, - \ D \ - OM3 22C-.225 / C..05 peanut yro' z77 hilcide (d) oCg 222--22Ej G6 477! Oil acid NEL, CE - "- OC3., 222-226 / 'C, C6 from locust! 3' j Î.) / 13 f 3478 Oil acid, ci 231-240 / 0.05 d chrysalis C2H5 l 479 Oil acid of 1 NH2CE-6-CE3 223-240 / 0.05 shark liver z3 (shark liver M3

  <Desc / Clms Page number 97>

 
 EMI97.1
 480, Oil acid of rIH2clrH - .. ocH5 217-231 / 0.05 sardine t \ == 0 sardina G "H3 481 Oil acid of NH2CH Br 220-225 / 0.06 naquerel EC 3 482 Acid d NH2CH oil 195-220 / 0.06 haioeig 1cH 3 CH 3 3 483 Acida oil of NH2j H4H, ..

   201-230 / 0.05 Saurel Saurel ¯3 ¯ bzz NH2CH Oil Acid, 40 -% - 200-225 / 0.04 Cod Liver C "3 Jl 485 Oil Acid NHÇHy-O # - 196- 236 / 0.05 485 Oil acid 2 196-236 / 0.0.5 mullet 3

  <Desc / Clms Page number 98>

 
 EMI98.1
 , -3 z J Oil acid of = Nr'iG 181-241 / O, U6 neidsadcn "5 1" = "487 ethnil acid ci 195-24O / 0.08 487 Oil acid of I # - j 195-2Q - pleuronect 488 gjg / gj # giio ÎzzµH ± PCHS '5 2 Q-235 /, 5) 488! .'ide of oil ce5 204-235 / 0.05 residual 3! ¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯¯1¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯! #### i

  <Desc / Clms Page number 99>

 
 EMI99.1
 ------------------- - ## - -. ## -. ### # - - "g%" r "N '%'" '' -r : o '- "" ".. pJ.e' 3acid fraction 3racti amino 1 µ cn 1 / ÇQg ± Ç [µµÇµ ± Î c% 1) é¯ N% J Acid fraction Fraction at! 1ino! cC I1D = éō ¯¯¯ jla 1 -Théo- 'aly- ± lhéo- ¯ Lualy-;

   1 1 tick tick tick brick tick click ¯¯¯¯¯¯.,. ¯..¯¯¯..¯ ¯ .. ¯.¯¯¯¯¯..¯¯¯.¯¯¯ --¯¯¯.¯¯¯¯af .¯¯¯¯¯ ± ¯¯¯¯ ¯ ¯.¯¯.¯ ¯¯¯¯¯¯¯ ¯¯¯ ¯¯¯ 489 Linoleic acid 1 1. NH-CH-NO2; ; '¯ 23; 1.5111 i i f 72.86? 2.93) 9.4; 9.60 1 î 6.5 '+! 6.49 " <3! '3 j il' f 490 j; Oleic acid 1 Í CH-o 22 1 1.5124 thread 72.93 73.06 9.97 10.03 il 6.30 6.25! 490 j ooecid C-7t l 'l-rc 2.1; ':!' ! 73, C6 j 9.9? j 1 6.25 z-5 '2 Iii! ! . '; 491 d: ¯tClene cide; t3Ii CH NO! ! 23 '/ i, 510O 1 j3.60 73.80 9.7-5: 9.30 i 6.36 6,.;.



  492 160 1 XHCE '' 1! ! 5154 26 06 J i! 492 t linoleic NR2 CHIF t 1 i 1 1.5154 ¯? 3 26 1 "> 56. 1.52! Il!!, Ef 6 24 C2H5 2 492! Lino1éiquo" 2 "5 73'261 '9.561: 1 6.331 f . f 493 Linoleic acid "2 26 1.5109 72.86 72.89 9.41 g, 48 f 6.54 # C, 37 fi 1 ¯¯¯¯ ¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯L ## -. ## ¯¯¯¯¯¯¯¯¯¯¯-¯¯¯¯¯¯J¯¯¯¯¯¯! ¯ ¯¯¯.¯ ... w ...... ¯..¯¯¯¯¯¯¯¯..¯¯¯¯¯.¯¯ ¯.¯¯¯¯¯¯¯¯..¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯.

  <Desc / Clms Page number 100>

 
 EMI100.1
 



  494! Isostearic acid! ) hHGH # -N0 j 1 27: 1.5156: fi 1 72, le i 72.24 - 10.25 10.40 t 1 6.48 ±, 34 3 \ == acid <E> 3, NC2 1.5152; 2.18 2.20 1 1495 -Isostearic acid% ca 72.18 72.20 10.25 10.36 6.48 6.34 490 Acl & elsostêarlque. EC 3 S8: 1.5152; 72.18 '72.20; 10.25, 6.48 6.4 496: Lci: the oil of NH2CH 22 1.5139 '! carthane 0E3 1 3 2 497! Oil acid from j CH gQ 2 20: 1.5131 soybean oilc) 'XHGHQ G2p¯ 1 z2) 5107 /, j Î j 498 Oil acid from NH2C, "22 1.5107) C-q3 2 499) / "ztElÔ-E0 oil acid 3/22 / 1.5122 / 1 castor oil NE 2 CH- N02 1.5122 'castor" j #, 3 = --------- L --- 1 ----- to ------- É ----- to. - .--- -i.-.-.-..- -, ù.- .. . - .. i -.-- -

  <Desc / Clms Page number 101>

 
 EMI101.1
 500., lCÒP @ flle ± p µ SB ± CH ± Po 24) 1.5123 500, Icjd 'pgp2 1.5123 Ma: Ls / ¯.I j' C37 501 Oil acid;

   NH2CÜ- z3 1 5bzz9 cotton == 'C càton Cg3 N02 5O2 Iwida d'hnil 1% ± CH $ Ro 1.5153 502 -Lr-ida iffl2cff oil, olive -0- "') 2 25! 1 , 5133 M3 503 Oil acid from E]; RHjCH ±? P 1,53.19 503 lin c ': uile t \ 51-19 i 504 Oil acid from \ 1 "" 4.51 1.5139 rapeseed \ == (- 5) i ± liiii d'i (r 3 p z..5 'z. "39 505) Oil acid [jj M% OEfl # -No [18) 1 d 1.5123 505 àcJ -de dlhilile IQH2G, 'H-1-p2 1.5123 rice bran == 5

  <Desc / Clms Page number 102>

 
 EMI102.1
 506; Oil acid of: 1CHNO2; 23 to 1.510.



  1 chrysalis 1! cH3 t "!!:% z Oil acid of NH2CHN02 22 1.5122 'c25 i dO 2 508 1 l .. oil acid of! I3, H20H 20. µ 1 1.5148 liver dG: ±' cquin jj! shark liver! 1 .. t 509 '1 Oil acid of 1- CH - 0 2 23 t 1.5134! 1 1 -whale CH- t J f 510! Oil acid of! KHàOE 28! 1.5120 cuttlefish "! "N0 dry CH3 2 i! 1 I! 1.! 511! Oil acid NH2Off 23; 1.52211 sardine & i: 3 2 fi

  <Desc / Clms Page number 103>

 
 EMI103.1
 f '! } '512: 1 iCH-o-N02 ethnilic acid! 23 1.5145 qu 1 == il naqqeneau 513 i Oil acid of i 1% # - "1 i 28 1.5235 1 scoobrésoce! Rice 3 '= - <NO! . ! 514 =! j Acid. of ILCH CS oil, 2 "2 1.5114 ';) 51Q' j Î id 'drbii 1 o 2' j) õ 'i herring ry * # e / f /'.) i) 1 { <! 515 cidc d.hui1e / r !! 1 1.5138! 515 Oil acid NHGH 1.5138 saure1.

   CH3. 2:) ï! ' 516! mI.2C1I02 oil killer i! 3211.5149 Î 1.5149! nenha.den = 2 nenhaden 1 1 oil acid N0 Ii oil acid diz, N02 fi- 517! Oil acid dG NH ,, CH- 32! 15150! decreased liver 1 = l 5 ¯

  <Desc / Clms Page number 104>

 
 EMI104.1
 T i NH 2 CH oil acid 25 5208 liver j F OE 3 1 2 519 -N H2CE-0-02 oil acid; 21, 5, I, j14Q; 'CH /' 520 residual \ -NO JGV lÀxilÉ ÎÉ 2 '! residual <J02 -5133 1. i C2H5 - = r

  <Desc / Clms Page number 105>

 
 EMI105.1
 "112 &% - 0
 EMI105.2
 - '"- 11%! Acid fraction Fraction! Property' - ## - ## - J - ## - L ---- J - ## - h 1; i acid raCu.Lon Fr riété tanaly - Theo-: Analyf;:

   ric tic ric tic riquei tic: ------- 1 -------------------------------- 1-- ----------------- i ------ I ------- I ------- I -------: - ----- J ------ j 521! Linoleic acid d (+) m.p. 45 .48 C. Î 83, Ell j 83.76 9.87 la, 08 3.05 3.14 522 ùE (-) m.p. 45--48-C. 83> 60 83.69 9.8? 10.04 3.05 3.14 523! J dl () P.F. 45C-48 C.! 83.60 83.67 9 87. 10.03 3.05 7.13 524 Oleic acid i dl (+) 1 Waxy SeDi-solic;

   83.24 83.35 10.26 la / 32 3/03 il14 525 Lsost5aric acid / dl (1) at "1 82.88 Ô 83.04 10.65 10.44 1 3.18 526 .. \ cide isostearic of "Î 82.88 / 83.05 10.65 10.89 '3.02 3.08 526 (-) 8?, 88 83.06 1 10.65 10, 67 3.02 5.08 527 ( -)) 82.88 83.06 j 10.65 10.67 5.02 3.08 528 Mnolenic acid d-1 83.97j 84.12 9.47 9.73 3.06 3.22 528 Acid gBas d 'oil do j dl (- <-) "83.97 j 9.41 9.13j 3.06 3.22 / 529 fat flax '1mile (:!:

  ) 530 Oil fatty acid from d (+) 55D) safflower from) d (+) 531 '(-) J 53rez) j dl (i)

  <Desc / Clms Page number 106>

 
 EMI106.1
 
 <tb> 533 <SEP> Acid <SEP> of oil <SEP> of <SEP> soybean <SEP> dl <SEP> (¯) <SEP> Semi-solid <SEP> shoeshine
 <tb> 534 <SEP> Acid <SEP> of oil <SEP> of <SEP> dl <SEP> (¯)
 <tb> sunflower
 <tb> 535 <SEP> Acid <SEP> of oil <SEP> of <SEP> castor <SEP> dl <SEP> (¯)
 <tb> 536 <SEP> Acid <SEP> of oil <SEP> of <SEP> rapeseed
 <tb> 537 <SEP> Acid <SEP> of oil <SEP> of <SEP> cotton
 <tb> 538 <SEP> Acid <SEP> of oil Olive <SEP>
 <tb> 539 <SEP> Acid <SEP> of oil Peanut <SEP>
 <tb> 540 <SEP> Acid <SEP> of oil <SEP> of <SEP> lo- <SEP> "
 <tb> custe
 <tb> 541 <SEP> Acid <SEP> of oil <SEP> of
 <tb> chrysalis
 <tb> 542 <SEP> Acid <SEP> of oil <SEP> of <SEP> liver
 <tb> z <SEP>)

    <SEP> of <SEP> shark <SEP>
 <tb> 543 <SEP> Acid <SEP> of oil <SEP> of <SEP> sardine
 <tb> 544 <SEP> Acid <SEP> of <SEP> oil <SEP> e <SEP> of <SEP> maquercau
 <tb> 545 <SEP> Acid <SEP> of oil <SEP> of
 <tb> herring
 <tb> 546 <SEP> Acid <SEP> of oil <SEP> of
 <tb> saurel
 <tb> 547 <SEP> Acid <SEP> of oil <SEP> of <SEP> " <SEP> "
 <tb> 547 <SEP> Acid <SEP> of oil <SEP> of
 <tb> liver <SEP> of <SEP> cod <SEP>
 <tb>
 

  <Desc / Clms Page number 107>

 
 EMI107.1
 548! Dl oil acid, -)! Seni-sollde mule shoeshine.

   l 1 j mule
 EMI107.2
 
 <tb> 549 <SEP> Acid <SEP> of oil <SEP> of
 <tb> menhaden
 <tb> 550 <SEP> Acid <SEP> of oil <SEP> of <SEP> " <SEP> "
 <tb> @@@@@@ necte
 <tb> 551 <SEP> Acid <SEP> of oil <SEP> resi- <SEP> " <SEP> "
 <tb> dual
 <tb>
 
 EMI107.3
 ---, - ¯¯-¯¯-¯L¯¯, ¯¯¯¯¯¯¯1¯¯¯¯ ¯¯¯, ¯ ¯ ¯

  <Desc / Clms Page number 108>

 Example 552
A solution of 14 g of linoleic acid in 30 ml of ether, a solution of 7 g of [alpha], dimethyl-benzylamine in 30 ml of ether and a solution of [alpha], dimethyl-benzylamine in 30 ml of ether were mixed together once. 11 g
 EMI108.1
 of dicyclohoxyl-carbodiimide in 30 ml of ether, then the mixed solution was allowed to stand overnight at room temperature.
 EMI108.2
 



  The d: 1.cyclohexyl-carbodiimido was decomposed to the oxoea with 2 cm3 of acetic acid and the precipitated dicyclohexyl-urea was removed by filtration. Then, the filtrate was dissolved in 100 ml of ether and the ether solution washed with 5% aqueous hydrochloric acid, 5% aqueous caustic soda and water, then it was dried, concentrated and distilled, to obtain 16.1 g of a desired product with a PE of 198-222 C / 0.06 mm Hg.



  Elementary analysis;
 EMI108.3
 
 <tb> ,, <SEP> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 81.55 <SEP> 81.76
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 10.90 <SEP> 11.02
 <tb>
 <tb> N <SEP> (%) <SEP> 3.52 <SEP> 3.82
 <tb>
 Examples 553 to 60 are shown in the following table:

  <Desc / Clms Page number 109>

 
 EMI109.1
 Duration :. c% i H% Fui% i Amine Acid Ivant of PE. -------! "'----! ------------ j --- 1 --- i .li.cide e! BN = C = NB 1 Solvent reaction C / um Hg 1 Theo- Analy-1 Theo- "Theo- i Ana1y-: 1 j [j (hours)] / rique 1 tick Î riq: ej tick tick,, -3 ------- jji #### # ..- -r--.



  3 Linoleic acid) f #! 3 fi 1 J Ether; 18: 1 203-218 / 0.05i 81.55 81.66 10 'O 1 l' l 06 3.52 3.68 C "3 '; 1 (d) - j - -, t linoleic; CI) Î Ç - - / Ether âQ8-Z2ll'O OVÎ j 81 55 j 81? 6 / / 10 90 ll 23 3.52 3 71 (d) EtIbie 81, '76 10.90 11.23 -j52 3971 Linoleic A.ide ; OE'3 Ether Z08-22VO, 04! 8.l, 81.76! 10.90 .23}, 52 linoleic / xHIi i)) - j) Toluene) f 199-217 / O, 05) 't 81 , 8?) 'F 3.4o' - I Linoleic acid, NH2CH f 1 -0 Toluene; 18 199-217 / 0.0 81.69! 81.8? 11.0211.45 3.40 3.52: 1 ... f (j 1 .... 3 C25 5, ..: .. :: J; Iinoleic acid: NH 2 Mb bmzene 18 20-22? / 0.08 74.69 74.79 9 e65 9.91 3.35, j.



  Eyelash 72. ljj law [.



  Linoleic acid; nzµI + Ô - ,, zltne 222-225 / 0.0.72 74.69 j 7., 81 9.65 9.93 5.55 3. * 3 * 9 Acid linoleiN # J-.ne t222-225A) , 07J 74.69 74.81 9.65 9.93 3.35 3.39 es- '!

  <Desc / Clms Page number 110>

 
 EMI110.1
 ---- vr .. 1 - "'." ----- j t #. - 7 ";. I 1 if.: 'F 558' 'Lineleic C ide lEICH ± -ci i! Benzene 18 j 220-225 / G, 08;? 4.69 74, 38 S, 6S 39: 3.35> 3 .59!! 558; nucleic acid 1 # CHci 3) -Q! 1 Benzene! If 220-225 / 0oa 74.09 74.38 9.65 9,% 3.35 Il 3.59 i.

   CH 3 .. / V1! Bealzène 25-240 / 0, C3J! '69.01 63.56 j 8.79 3.10 3.52: 559,: .. linoleic acid Im2CH If (-1 Benzene! 225-240 / 0.031 69.0 69.58 3.69! 8.79 }, 10 3.52 cy¯,;> ij, 1 ¯, 1 j Ô g, 1 '? 1 [1 1 (1] " <i 560: Linoleic acid: ICH-Er 1 j '225-235 / 0,2! 67.52 67.63 1 1 f 3.23 v560: '¯: linoleic acid; IrI2Cg! .-Er i-CH <¯3ITouènc! -:, 225-235 / G, 2 67.52 3 67, E3 8.72 8.76 5.03 392-9 CE 3 i i. l $? I s61 lcàde 1 ÎlHzclb. çx 1 "l '1 1 1 j 0 to 67.61 1,,; 8,? 2 8z77 j fµÎ> 1 i ..cide t Br i) 225-233 / 0.1 i; 1 l 8.77 3 , 03 d 30.



  561; : "linoleic cide! lm-CE - --Cae3j Dioxannei Il 225-2330.3 67, .52 67.61 8.72 8. ,, 77! 3.03 rice ig] - =. / CH!. 'ca , -3 d 1 3 1 lf: ...



  ! .,.: .. f -.cde linoleicJ C'H 1 # ¯ (3a Ether 221-23 $ / 0.1 67.52 * J 67.70! 8.72 j! 8.GO 3.03:. 'f . at .



  't 562. ¯ "' linoleic acid! - IM2 Ether f 221-238 / 0.1 6?, 52 67, 70 8.72 8.80 3.03 t $ j2µ" '-LI rrr: rl' IY! : I '. f seen '% l "' 1 1 1] .... c..



  '! , \ == / 1 1. ...



  !; t IiI f! ! i t - 563: 3.inoZeic acid: t NIi2 iH-- Hr -0 Benzene 20 1222-238J0.09 '68.06 i 68.29 8.821 8.94 2.94 3su f' 1> é '563i Î <j '' ± linoleic acid 'jj' i 'XHzcE-- à5 1 Bn Î j 1 j' - Benzene f -, 82) 3,06 C2fI5 JI: II ", 1 ......, ... ........ .... - .¯ ... ................-...- ¯ ... ¯¯¯ ---- ¯-.¯ .... .. ......... .... ¯ ....... ¯ ............... ... ....

  <Desc / Clms Page number 111>

 
 EMI111.1
 



  - ,, "- o -, - tl 'z¯¯ 1,. Ï Acid: linoleic! (): Benne! 18 J208-221 / 0.04 81.55 81.55 10.90 1 3.52 3, 68 '4-! Linoleic acid: I3Fi2CE --- t) Og Benzene i 18; 20 $ -221i:) a04;. 8155 = i $ I, r7'lr 10.90 Il0,? 4. 10.74 3, 52 3.68 1 \ = / JI f IiI: 1 to 1 Ù j> 7 Î, 1 j 1,; 5: Linoleic acid: 1 NH2CH- GZ ', iD! Chlorine-! Î 12 1 1' 220-z25 / O, 0fll! Fi 74.69. J 74.83! 9.5.5 3; s3 j Ii 3.35 3.50 NR21 form f 'j ;.



  ! t # fome i j 1 1) 1 1 É Ô) "É 1 1 .... t:," f f "'." 'ciàe i; noiéiouel (d) i Chloro-! "21-227 / C, OS; '..., R. C: fi r Ec i. $: 6 9.90! 3> 35 2;, 61..Linoleiu acid. 0-' .r- \ 1 G ..: i4, = 9, 3 =, 5,,. 3s35 3,25 1 Î 2 L3 1 -! 1 [fQIye l 1:! I 1 !! Il! Cil ..:.



  7: 1,. \ Eida the inoleic! CHb '3' If D! Benzene: 22 (') - ;: 25 / 0.0911 78.40 J i 78.09 10.48 l (., 32.i3.39 3s s.: ..



  1: CH3 j ..- 1-4 +3 OCR JI! 1 ... ¯ '' ..cide f ri "3 J Taluene 12; 218-223 / 0.09! 78.40 j 78.08 10.48 FT¯0.3 $ 3.3.:. Linoleic water 2Î \ Toluene ¯ 218-223 / 0.09! I ï 78.08 t; 1:!. C ',? 5 3.39 f. .. ..



  : i - i ....: w wi Î / / / / Î /) / .. fi 't = i: 1 ido liMic] NCHOCJ f D Toluene 12 220-225.1 78.40 78.07 10, 48. 1 (), 31 3.39 3.26 4ido lino1éiQUej CH '= T-vv Toluene 12 1 <'78.40; ? 8, CJ1 10.48 10.31 3.39 1 3.261 "! CS-, lIt fil -:! 3 j¯ 1 J. I f: - .: fi '1.



  .. - ..... ¯ ------- --------'-- 4 ..1> .. 80. .III .. ---- ...... "¯W" I ' <fi '-4¯-- v -...-- "" ---- ---......... 4¯--

  <Desc / Clms Page number 112>

 
 EMI112.1
 v ¯¯¯¯.-. - ### -. - '' -------------------------- '' -------!.



  ,; "CH, 3 i. I! I.!! R! 1 J t 570 Oleic acid; NH2CIIÔCil5!! I -0 JBenzene 1 6 21I-22 / 0.08 ±:.:: Ô1.29: 8I, 41: 1 Il, 45 !, 1 11 jf 3.9 3s51 'i.'! " i 571 Oleic acid s: CH l \ 2H5 -0 Benzene 3 l. 213-22310.09: 81.44 EI '65. 11.55! fi! 1J., 69 3.28 ['3.50 to:; j ",! ri to [.572ideoleic! oleic acid NH. f Cï - Br - Toluene 6 2? 6-230, C9: 67.24 87s- '.; 9.05 to 1 Ï 8.8i 3 , 01 d / '3.39 d 1:, 5? 3fAcid 1 isostéa- hHCE ± @' j \ = t '"i - t Toluéne 8 d 1 80,? 3 80.91 11.83) t 3> 9 ) Z 5? 3f..l <; ide Í isostéa- mIzCH-Q- #} Toluene f i 2G0-2l7 / 0, CB BO, 73! ï 'f: 8091 11.83 12.03!,, 5.49 3, .Eif .: .- .: 573Isostea-NCECH acid. JToluêne! 2CO-217 / O.C8; 1.03 3.49! 3,%: 1 "" rra 1 l. 1 1. (1 /. ..... fI 'j j 1' ..



  I3H.2Cg 1 Ether it! :.



  574 Isosteal acid - XHgCH $ E-oej '7 ") Ether: 10; 209-23l / 0.1 81.33 81, 52 12.11 12, J2 3.05 j 3,:" ,. f J "' + i H5))! J t! 1 i fi zli '1 "l Î i rique 1 i CH-oC1! 1-0; 10 221-228.09 74.02, 74.33 10.43) 10.66 3.32 3.61) Î 1 risk OE 1! ! Î l j.



  ! ¯..¯¯ ... ¯¯ ... ¯¯¯¯¯.¯ .. ¯¯¯¯¯¯: ¯¯¯¯. (, ¯¯¯¯¯ ¯ t¯ ¯ ¯¯¯¯¯¯; ¯ ¯¯¯¯ ¯¯

  <Desc / Clms Page number 113>

 
 EMI113.1
 :; 'Ù'; -icide isostea- /, WCH ± -3n 1: J Ether 6 d, 223-24l / O, 1,66.95 1. 67, Ù6 1 1 9.44 9.58 '3.00 3.21 eric' 223-241 / 02 '66.95 67.06 9.4-4]. '1 3.21! fi7 ',; / / acid mque "", isostéa-; ,) (RIICHfl # -OCH b j 3 3; + to) ± 'j / Diokanne' / µ 12 221 226 / Ô 05 t. 3-0 Dio: Xanne fI 12221-226 / 0 77; 64 7774 11, 34; Ji 65 3935 3.15! j - ± 'ln 1' Di. '221-22 <, J 1 77.74 't 1 11, 1 7Sjlcide (i isostéa- lNfca, ± -OCH 1 j I µ J S.! ".'O, .M 78.32! N,! To j 11.5B 1 ( 5,1 "Ï 3, Q8 isosteal risk:

   NF / iI, o- 02H5! hexane.!.? 2? 2- ':! 3:!:' O, I) 9 18) 1411 '78, 32! 11.53 f 11.58! 3 E ric C- "15 hexane '== 5 d,' 1 ml NH CH-IC C2H5 Ether 20-0.08: 79.61 79.93 10Lo, 3l 3.29 79: 1: l. cidc lino1- 2 1 dērr z-5i 1 J "-: Ether 12 22O-259/0 O8i 79.61 '79 .93 10.18! f 1.0.31! 3.29 3.3r.1, nor quo! ui'3 ":. #: 'Il: SOcidelijool- ÏCE -. O # L - /" \ ydro- -! R 1 t 79.78 101-18; 2 ...'. lino1 & -! 2? 5 furan 218-238 / 0.1 '19? 8 10; 1811 10,: 12 * .. *: mque Ibydro-furan. : t = 1: j 1 -Leide linoleum- j-0-3! 'Benzene S21-240 / O.C9 81.97 e2.06 1,094.5 10.69, ** t lino1- NR2 # -Q- # 3 Benzene .221-240 / 0.091 81.97 / 82.06 10.45 10.65 3, o54 t28

  <Desc / Clms Page number 114>

 
 EMI114.1
 ! ---------- 1 .......- r 1 ------ ¯¯ ¯¯¯¯ ----- ¯ .... ,, --- - .. -., ... ----- ......- -...----- 1, i CI! the - '.! 1 j t f .: 1,582:

   Linole lcid- CH-o -O. ! Benzene 10 m 219-239/0, 2 m 75.09; 75.19 9.14-10.09 3.36 3.6? 'j i H3 = 5S3: cidc' of oil 1 NBCH - CH / #. Benzene i 10 1 / 199-219 / D C9 '] /'; 1 1 i 1 do lin CH 1 lin 3 bzz, j 1 µ 1 /] j, j]; ; '' t '' 5E4 1 oil acid # - ci 1 ', 1 fi' j j 1 Ben # ene ''. 1 2? O-é3Q / 0 "b) i j 1 1;, j 1 j lin 224--234fp.:6 - lin" 3 '' # <'thread, linen !. j t I! fi! t fi 585 =. oil cide i? tE2CF tj tBene 203-20git., JO j.585!: "oil cide NH2CF-D-CH ;: -0 i) 20-2091 {., OGf u :: iw .. carthane l '! if' .....



  1 t'f '' j i -}! 'f 1.



  Ù 586 / L Oil acid GXjCH ± Q Î Benzene j 10 1 2O3-2lÙ / 0 06Ù! 586 Oil acid CHQ) Benzene j 3-211 / 0: O6 1ft carthane <c it ;. :: f: f "." 1 I .. ;; J .. '1 i i ** / Cn) j #) 1! ! 1 58? = of oil carthane acid; RH 2 CH - / \ i Ether 219-228 / 0.06 '58% in oil acid (-s. # - Ether 219-228 / 0, O6i if cartharle r <cr 1 Cil z .. * '. '1. '

  <Desc / Clms Page number 115>

 
 EMI115.1
 568 'Acid in)) m% llj / -Br -0 Ether i 220-226 / 0.1' C-2 "5; 1.589 'Imil. Dej! NII2CH' XH ... . -Q er 4! 219-23? / 0.06 589. Oil acid Nil Ethe: r soya:; nï! 8 / 'Eoàa 590! Acid d-hlc e-0 1 1 * / Ô' 3h 1 ; ' Soctoumesoi. C:; I !. 1 <A) '591 Oil acid of NHCH - Cl)) () .B.: R..7.E: n (1 1. ;;: 218-228 / 0.01 castor' "-.1 ; castor oil! 992 1: "'oil cide of! 1: CH-o-OC5 l' j '-0 1 ToJ.uene! 1 22J.-228 / 0.041 rapeseed b" 25 z) f 5931 Acid d' hu1J.e.

   (1 Ii! Ether 'J.O 22; -231 / 0.0S 59! Oil acid NH2CE4 \ -OOE3 Mher 223-23110, r-15 cotton 7' -.J

  <Desc / Clms Page number 116>

 
 EMI116.1
 594 Oil acid NBCEV-c Benzene '' "i 214-229 / 0.05 .594 Oil acid Î i 'Î25! Benzene 214-229 / 0.05 olive G 3 02g5' # 'i: 10 21-.229I0.05 595! Of oil NH # y-OCH (- / * '\ j; r! 220-227 / 0.06 595 Lcid of oil NH2CH4 Benzene? -20-227 / 0.06! = d aracbid; 3 1! f -ji 5 ', 6 E-1 iiiil acid of NA.2 d) Hl - OCH3;

   4 \ / 2; i'xrnne 12 223-22? / O, 06 locust CH # 1 j 597 Oil acid ï%, (m - Cl -3 - / \ Tbicro-! 233-242 / 0.05 ) 597 ù-oil cide of XHCEjà * ± J 'chlcro' 23J-? 42/0 chrysalis 1 / = 'form C2H5 () CE3 i 598:. Oil wax of = NH2CH- (0 CH3 -0 Toluene ! io 225-241 / 0.05 shark liver C "3 '# 599 Oil acid of NH CH - C2H $ - /) Tetra- 5 218--232j0,05 sardine 2 j \ -! hydro- 0H3 a' furan L- # L.¯ ### L ## .. L.¯-.L - # ..- L # ¯.

  <Desc / Clms Page number 117>

 
 EMI117.1
 



  ', - ¯ "!. #' T ')"; .600; NH2CH Oil Acid Iir; Dioxannej 18 22J.-227 / 0.06 # .quoreau CH f mackerel '= 3 t t 601 j ± oil acid of,,. Acetozw 5 193-223 / O, 07 601 Oil acid 1 ClI -0 j Acetone 193-223 / 0.07 '1: herring "5 1 3 j I 1 j 602 f 1! C1do do CH- oil o-CL; .Hg 1 i Ether 10 202-231 / 0.06 saurel "i 3 1 605 i Oil acid) j NHzjE ± fi-CH -0 Benzene 20 199-227 / 0.05 norue liver C4 1.11C 2 604 Oil acid of NH2CH OCH - (*) Acetone 94- 37 / mullet ± lltli "Î ± F '5"' '? /' "Dulet 3 605 Oil acid of NH2 CH 1 OCH3 -0 Ether 5 t 181-241 / 0'061 Jill #, 1, if 1

  <Desc / Clms Page number 118>

 
 EMI118.1
 "!! 606% Hil / Toluene oil acid 1 186-24l / O, 08 6061 Oil acid deilili 2 -0 Toluene 18 186-241 / 0.08 pleuronecte '== * # plem * necte C2R5 #? 7! Oil acid ICH -'- oc-E ..

   benzene 201-235 / 0.06 60? ± NH2CH pCgs' Benzene 201-235 / 0.06 "?)! Residual oil;" <CH-. 3 = 5 # <) ")) ji /" = ¯¯¯¯¯¯; ¯¯.¯..¯¯..¯¯¯.¯¯¯¯¯.¯¯¯¯.¯¯.¯¯..¯, ., L - - -.------ .. --- .---- ----

  <Desc / Clms Page number 119>

   Example 608 -
For 20 hours, we heated at 180 C, a mixture of
 EMI119.1
 28 g of linoleic acid and 14 C of t: {, r-d1 methyi-benzy1amina. After separation of the water, the reaction mixture was distilled to afford 33.3 g of a desired product with a m.p. 119-219 C / 0.05 mm Hg.



  Elementary analysis:
 EMI119.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.55 <SEP> 81.77
 <tb>
 <tb> H <SEP> (%) <SEP> 10.90 <SEP> 11.04
 <tb>
 <tb> N <SEP> (%) <SEP> 3.52 <SEP> 3.49
 <tb>
 Examples 609 to 663 are shown in the following table:

  <Desc / Clms Page number 120>

 
 EMI120.1
 1 ¯ --------- - 620 Linoleic acid I # -f-ca,! 180 12 2O8-224 / O '05' µ '81' 55 '81.69 10.90 10.98 3952 3172', lucid linoleiqn; e cH \ == / 3; 380 208--224fo, o5 10.0. 1 1 3bzz 621 i Linoleic acid V-d! 175 220-225 / 0.06 74.69 74.81! 9.65; 9.92 3.55 3.45 621 Linoleic acid N ci 175 12 220-225 / 0.06 74.69 74.8: 9 65 9192 3.35 3.45 (d) 1S0? 21-2 5 / O , 08? @, 69 '? =; 83) 9.65 9.9C J, µ5 3.61 622.

   1i.2a3eic acid; mCH- # Cl (d) 180 't2? 21-225 / 0.03 21 [k 69' 3t '- .: g 9.65; t3i, 5 <35J 3.61 622 11-Noleic acid 1 i 62 ', AG3. Lino3e3.Ctz. OCEI 3 3i5 22O- rice 08 zou i8.85 Io ,: '39 ¯ 2g "s 623 Linoleic acid' OE2 175 220-224 / 0.08 78.40 78.85 10.3 10.63 3.39 3, 2Ye., 6) Acid iéi e CE- b / 1? 5 22 -'4 /, 8? 8 * 4)? 8.85 i 8) 1> 65)?> '9 * .. LC "3 rf if CC" 3 624- Linoleic acid EI2CH-d 180 18 218-230 / 0.1 78.40 78.59 10.48 10.61 3a '. 3.7} 624r Linoleic acid <* / 0f t 3 Ou3 18O 218-223 / 0.09 78.4O, 7858 10.48 ï 10.61 3 139 3.48 Linoleic acid RHÕE-OCH H5 lH 180 2l8-223 / O, 09 78.4O '? 8.58.10.48.10.61 3.39 5.48 625 Acid! 7.f.o3Li acid ue 2 (/ J oCH 3 180 218-223 / 0.09 78.40? 8.58 10.48 10.61 3.39 3.48 M3 1 --- ¯¯ --É ------ l ---- '

  <Desc / Clms Page number 121>

 
 EMI121.1
 Temperature% / f1 1 1> le, Acid fraction Frac1ïi.on am.ino:

   crossed out. da la I -------- ----- - - .. t-- - µp Acid fraction Amino fraction of the reaction: OC / ma Es Theo- 1 Analy-i Theo- 1 Analy- Theo - Lnal- '"reaction (hours) C /' I! JD rique 1 tick tick risk / tick tick '- ###. ------- ¯ f (OC)! ------- -j 'I: ie, ¯t! l Tii fTT 609' TO 'linolei OE3 XO 1 202-219 / 0.05 81.55 1. t 5, L8 609!;.: .. linoleic cide f 1 CH' 1,200 12 202-219 / 0.05 81.55 81.61 10.90 11.02 3 $ 52 3.48 CH 3 \ = '' {! 610; Linnl'iqao acid NHS-C3. 205 12? '18 -% 0 / 0.05 1 1 81, 55 1 '81, 6 "5 10.190 11.05]) 3.52' 3.48 Î '' 3 i 1. VJ: J. 3 lj 1: \ 1: 19? -209 / O, 03 81.69 81.79 1?, C5 µ, 3l,;, 1 Inolei NB # 180 12 j 197-209 / CI, 03 81.69 t 81'79111.02 11.05 3.40 5.3l ,.



  * '--if1 2% - It! / Ù ci r6l2! Linoleic acid li q 180 20! 220-22 '; 0.071 74.69'? L, 81 9.65 9> bE 3.33 3.2'7: f! T OE3 ci. 6l} i M1 of linoleic 1 NH-CH r <180 24 222-225 / 0.05 74.69 74.83 9.65 9.893.35 3119 613 d linoleic acid --- 1 - "= l 18O <222-e25 / 0.05! 9.65 1 [9.89 3> 19 CS He!

  <Desc / Clms Page number 122>

 
 EMI122.1
 614 Linoleic acid 'OE2, -x 175! 21; 21.9-224 / 0.05 i "74.69 74.84: 9.65 9.84 3.35 3.28 614 Linoleic acid CH 3 175 fit 1 2l90-224 / 0.05 74.69 74.8W i 9.84 3.55 3.28 615 Linoleic acid 1! III2CH-Ó CI 200 20 i 22;} - 24VO, CS. 69.01 e3 -3.69 3.7 "-! ;; ; 3,10 3,3C) 615 Acid lmoléiqe 5) / Î i 200, /) f 2J 223-2 # l / 0, C3 ¯ Î i 69,01 Î Ô) 'C3, ± 3' j / Î 3, 63 'g O, iL: - i (µ, 10 3.3o 616. i Lino3inu acid!! I Í! NB: 2CH & - CH} f 175;

   21> -? 0 / <. , 52 67, // 8, -72 8, lic) 3,, r, 13 1- 1. 3.45 616, Ac3.ô.e li; n3 éiOEue CE 3 175 6µ?, W 67; /./ &, 72/18, '% Q) Î µ, Vµ) ï. 3.45 j ¯ ¯ Br Ii! i bzz¯ f, j -617 Linclean acid! NH #. Br z 12 222..23D / G ::!. 67.52 G7.71 6.72 8, P3 3.C3J 3.43jj If:? Î "$ 616 Linoleic acid Br 200 i 12 220-237 / 0.09 it 6?, 52 3.85 3, 03 3.2 ..

    6181 '1J-noleic acid IM3 200 1 2 1 220-2 ;; 7 / 0.09 1 67.52 6? , 741 8, 721 9.85 3.03 1 3,: 1 CH3 619 Linoleic acid / RHIl ± fi-Br 175 21 222-234 / 0.08 68.06 68.31 8.82) 8.90 2, 94 '1.619 Linoleic acid 175' 222-234 / o, 08168.06 68.31 8.82 8.90 2.94C05

  <Desc / Clms Page number 123>

 
 EMI123.1
 4 "H - ##; 1 a26 a., Oleic acid i: 112CHC2H5: 200 12 208-220 / 0.08 '81.29! 81.41' 11.35 3.39 3.09 527:

   Civic Acid CB-y-CHe 200 210-225 / 0.09.62 11.55 11.36 3.28! 3.19 c> 27-oleic acid iH2, CH - C2H5 2m 12 27.0-2? Ii f, 3; '8 .'-, E2' 55 -l 6! 3119 c 2 H 528 Oleic acid i Ci -.- 3x 1? 5 a2-'r-23C., C3 67,2-t 6r /, 41 9105 9a-:, j.1. 3.32; i .e oié-e xaz <i <> j - Br; 1.> 5 ') "Li Î 29: Acid isostea-NH"> CH- -OE3 175 18 21510, 08 30.73! :! 80.90 II, E; 11.9T-! . '3.29 1. rique IEC riqne? 3 i30 Acid isostea-NHp # V-C-CH z 16 2G -23 "v / <lsQβ; 81.33 81.4? 12.11 121.2-2 'S, 76' 3I e 1 s: i: 4c.de riqus ïsostéa-.

   NH2C.R - Cl C I == CE3 3'5 3.8 221-22 $ / 0.08 z3.02 -! 3 3.32 3s ±: i. = 31! ; ! Acid! ! jmpCH - Cl 175 za-228 /> 8! 74.02? <?? 3 10.43 10.33 3.32 3.46! jrîque <-j)% = '

  <Desc / Clms Page number 124>

 
 EMI124.1
 J --- ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯-. ########################## ###### "" "" "" "}! 32 5 / '9" /; 2 # ± / j 200 12 i =? 2-2 # 3r / O, Gi! 66.95 67.06; 9.44 9.60 3 (i $ 3 '01' rique tTJ!>, Q¯ OE3 533:

   Isostea- IOE2C.9-f- OOE3 175 18 222-2 ^ 6 / 0.05>? 7.64 '77, & '3'-' 3 - St3 '33. 339 rique'! ! cg3 i. ,, j 0 i É. i 34 Isostea-I2 - (! s) -G2H acid; 17.5 1 <22-2? 3/0, C? . "6'Ï 7: L ': 11.55 j 1 11.51' l? ¯4 33 -rique c, 1" 635 Acid lîmlànque i Nfi2C3- 2H.J 175 18 1.8 2 '+ 3, JoG' 8: 79.61 d / '79> 6) 10.18 10,:%. . ', 29; 3.45- j \ t -. /,% O = * 0 '"1 .. -r 636 Molenic acid c ..- ocg3 180 18 216-237 / 0.1 79, tDi. 79.49! 10, 18 10.3l 3fi 35% i, ± Ô "" j é 2g5 ..i '[65? Acid! CH3 ¯¯' 175 21,,. 1> "5 jjj 1> 59) 3.54 -: ¯. ¯! 3 ¯ L ¯L - #! ¯-¯L -.-... i -.-.-.--, # -. L - .. l

  <Desc / Clms Page number 125>

 
 EMI125.1
 -----: - 7 - 7 "F '" f - - - "" j' T:

   ! 638 = Linolenic acid NH2ÇH 150 23 212-222 / 0.08 75.09 74.98 9> 14 9 34 3> 38 i 3.47 EC [3 i 639 of j CS-Q-oa! 220 12 d 19S-226 / O.OS f. 1 lin of NH-CH 1'I1'T oil: x 220 12 198-228 / 0.08 i j !! . o! ! ! 'j i 640 Oil acid of NIL, CH - C1. 130 24 -; - 03-209 / 0.06! t 3 'ceE-' f i 641 Oil acid from! !., j N: .I2C \: 'CIL 15ü' 24! 203-215 / 0.07 #J! <-5. "1 ..



  OE3 Iii 1 .. '. i 1 ..: 1. . ' 642. Oil acid H., CH-1 175 18 27.'9.-228 / (3.06 '"j carthane' -! H == <.T "'3 642 d Oil acid do! Bzz 175 219-228 / 0.06 carthaae CiI5 643 Oil acid from NE2 200 12 218-224 / 0.05 -carthame (33 2" 5 safflower 1 - " '= <oc-'R '... ¯¯¯¯¯..¯¯¯¯¯ ¯.,. . ..¯ i: ..----: "------ = .----- ..1.¯¯¯¯¯-! - <-. "-

  <Desc / Clms Page number 126>

 
 EMI126.1
 644 Oil acid of NH2CH- (150 18 220-223 / 0.1 carfhane C2H5 k fit-5 1 Oil acid of NV-CBy 25 CH 200 12 2't.F3-2j4 / 0.0 soybean C3 ? i 1649) tiiggeli; =. = tJ + epÔ-Cr4Eg 175! 213-238 / 0.05 j 64 "J Ac; -tie ahille rii bzz '- 1'75 218-2 .. # 05 sunflower - ic * cl bzz Acid t3.'ll.e de ci 170 215-225 / 005 castor hi - C, 48 Oil acid from NCH.; OC2H 2 20 * -228 / 6 rapeseed '=' = -5 M3 649!! Oil acid from 11H 2 4 0GH 3 175 18 223-231 / 0, C), 5 cotton N -. F.; F ¯; i. C3?:

   ..

  <Desc / Clms Page number 127>

 
 EMI127.1
 



  650; ! Oil acid NH2CL c25 150 12 214-229 / 0.05 CE olive,! "= - '- 651!: Oil acid 1 NHCKÔXCù 175 12 220-226 / 0.06 peanut"! ca 3 te locubte j - J <; 2H5 653 Acid d% hLiAle de #. I'I i \, 3 i 180 12 .33-242 / 0.05 chrysalis' 1 CjH 6Y> Acido OCH3 180 j 6-! Hle F ItT acid, ç. 0 Og 100; 225-243 / 0.05 1 Î 1 liver of rcqoin 21 CH -1: .- '655 Acid of h, .. e of 2? -0-2 175 20 209 -;> P8 / 0.05 55 sa .rd3.ne 2 bzz z)

  <Desc / Clms Page number 128>

 
 EMI128.1
 'j' '-, -----) C56 Oil acid of Î: cH-- 175! 20,218-224 / 0.05.



  : i Daquercau i i CIl3 1 f! '., Ji t .. t Oil acid Nose j' 200 - 18 194-218 / 0.06 '657! Oil acid of "] /" 3200 18 194-218 / 0.06! herring ± .I. CH 3 653 Acidc 1 '"a'00 IHCE-Cjij' l '; 08O 19? -23fl / 0, e6 653;! Acid 1" la-' Ir, do z.2cj - .. ei 160 18 19? - 23 ^ / o, c6 1 1 saur: 1, j GB3 / 1 1 1 fi! t t III 659 Oil acid CH-o-CiL 175 -J 18 198-219 / 0.05 659 Oil acid ./ -. 5 175 18 198-219 / 0.05! : CI cod liver. 1 "# .....; j fi 1 1 660 Oil acid of i NIiZCH-r 175 1 18 1 193-240 / 007 lauiet 1 f 1 Llu1e1; CH} 1 IIi!:) Uulet 'E-' 661 Oil acid of ti NH2OE OCR 3 180 1 $ ti 183-239 / 0.06 merJ2aclen 1 3 '= "nenbaél.en. CH 3 J ¯! ¯¯¯¯¯¯¯¯¯¯ -.--. 1 - --- -. , --- ± .-, - - ---- ------ 1 --- to ------------------

  <Desc / Clms Page number 129>

 
 EMI129.1
 ; - ..

   Cl! j! ; 662 Oil acid from! CH-6 175 18 i 194-237 / 0.08 pleuronecte = 5: 663 Oil acid NHC3 - ccH.- c00 18 201-230 / 0.06 residual E3 \ = 663 î residn,: lle 1 ëR :; 1 2Cô 1/18 ¯¯¯¯¯¯¯¯¯¯¯¯ #. #. ¯ # ī¯) <'! ' <¯¯ ¯ ', ¯'! ¯¯¯! i i! t

  <Desc / Clms Page number 130>

 Example 664
 EMI130.1
 To a mixture of 13.5 g of p-d3-methyl-benzylamino, 7 g of trimethylamine and 100 ml of anhydrous ether} was added a solution of 29.9 g of linoleic acid chloride in 50 ml. of anhydrous ethor while cooling with stirring at Q - 5 ° C. After the addition, the reaction mixture was boiled for 2 hours and the ethereal solution was washed with acid, alkali and do the water, then we dried it. concentrated and distilled,

   to obtain 38 g of a desired product 6.



  Elementary analysis.-.
 EMI130.2
 
 <tb>



  Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.55 <SEP> 81.69
 <tb>
 <tb> H <SEP> (%) <SEP> 10.90 <SEP> 11.12
 <tb>
 <tb> N <SEP> (%) <SEP> 3.52 <SEP> 3.44
 <tb>
 
Examples 665 to 719 are shown in the following table in which: Solvent: a. Ethor b. Dioxane c. Tetrahydrofuran d. Aceton
 EMI130.3
 e. M6th - ,, "1-IsObutyl - ^, etone f. Benzene g. Toluene h Chloroforma i. Dimethyl-formamide k. Water

  <Desc / Clms Page number 131>

 
 EMI131.1
 ----: --------------------------------------------- ---------- i ---------------- ë ------------ H -% ------ f ----- w -% ----- i Fraetion aninn Agent of Theo- Amly-i -Th-60-- Analy-1 pie Acid fraction Amino fraction of i vant -C / I = Hgnique 'tique Theo - help tick tick i 1 I 'VE C3 K2CO3 Il! 200.02. he; 1 61.67 '. 10.90 t 3.52 il # l * Ui.

    i lJ / F) l / i. l.? l "?) l. 1! OE3 '., Î' - cHj 'N OE kd 209-221 / 0.0?) j 81.05 1 81.7l 00.90 1 j 10.1µ / t õ2 3.42, , 66 Acid chloride NH2CHV 1 NaOH k, d 208-221 / 0.051 81.55 81.71 $ C) o 11.1 j:?>, 52 3.42 linear - C "3 ll. '1' It! -, 25 .3,40 3,19 i-Z.547 Chloride cilacid 1 1 f CH-U CH K2CO3 d 200-209 / 0.03 81.69 / 81.90 11.02! 11.25: 5.40 3.19 Minolie C¯H 1 linoleic CÊ.5 fit: "": ''. <. **: llll /.-* '2 3 1 l 1?> 9)? l 9.i 9> 5):

   Uf "z-168 Dlacid chloride i Na 2CO3 74.69 74.82 9965 3935 S68! = Dlde 1 CHb 2 = 215-221A., 74.69 74 9.65 d 9.83 3.35 3-,, linoleic 1 f 1 C "3 ..- / 1. ..: ..: j. .: .. :: :: f 009 i oru: te acid lOE2CH '11 L ..! 22O-228/0, J 74.69 74.85 9.651 9.84 3135 3.12 liDo3.é: l.q "" L3 f, '/ l' 'j' 'bzz) linoleic l', 1

  <Desc / Clms Page number 132>

 
 EMI132.1
 ¯¯tr .. --- - --... - - ... :::,. - T- <; "" #############; ######; T ¯¯¯¯¯¯ eyelash 74.69 '74, 84 9.65 19-87> 7. Acid chloride e! 1'1 \ Lc;! -: a i 216-223 / 0.06! 74,69J74,84J 9.65, 9.8'7 '1 j ¯ µ 3.35 3> 11 linoleic \ ¯¯ "Q' 3 '2fl5 1 1 0 i 1' 'i' '' 1 1] 671 Chloride d 'acid' NR. OE- 76 c NaOH k, b; 218-239 / 0, () 6t 69.01 69.22 8.69 8.81 3.10 2.94, 11.! lo1éiquo 1 "l / '"' l '.' bzz9 '' 'linoleic.

   CH 3! 672 NH.CH - Br acid chloride OB '221-236 / 0.0 67.52 67.78 .; 8.72! ! 8.90 J 3.03 2.90 j 672 Acid chloride EH-,) B r NAOR ēēī - 23610.08 67..52! 67978 8.72 8.90: 3.03 2t90 * .linoleic xI + zEAJ-B OE 3 fiaOH '' d 221-256 / O, osl 6>, 52 67.7s s,? Z) a, 9o J, c5) z, 9o CE 3, 'jj 673 Acid chloride! % # ill% 3. '\ -! 1! '215-229 / 0' 672. 67.76. 8.72 8.92: 3.03 2, B1.Ii i i linoleic 7 Cil 3 "to ', .i. ..



  Br i "!. Q OÎ Q 74 'Chloride; decides NF- CH - 2CO3 218-235 / 0.08. 67.52! 67.71 8 72 1 3.03. 2.86"': ..



  &] 4 C1iloe of NHCH '1 23) 218-235 / 0.08: 67.52! 67.71; ) Ù 2, .i: linoleic linoleic 3 lit - 1 j Î ": 1: j fC2H 375 'Chloride i -.' Acido! CH-Br CzE5-¯ 68.06 68.31 '8.82. 2.94 2.67 216-233 / 0.07i 68.06 (58 8.82 2.67 375 'Chloride e.1 - cide IqH 2 CH-4 Br NO! 216-23; $ / O, 07 68.06 68.31; 8.82: 8.99 2.94 2.61? 5: linoleic 2H5 i C / 1 'Î f) 2.6-235 /> 1 1 68, 6) il! 2, ¯ 2n6?

  <Desc / Clms Page number 133>

 
 EMI133.1
 ¯ ..., ¯ # ¯ ..r ... ¯¯ 676; Acid chloride 'NH2CH-Q-CH3 NAOH k, c) 208-222 / 0.05 81.55 Bi'.70 f 10.90 f 11.05 3.52 3a4'2! linoleic 1 # 3 1 = Iii! 1 II.



  677 Chloride! of NSp # - / "- ci (/) SCO- acid; e 218-223 / 0.06 74.69 74.75 9.65 3.35 3.02! ' l,; 677 'Acid chloride rls2c'H--'! LC03 218-223 / 0.06j f 74.69 d 74.75 9.65 9178 3.35 3, p2! linoleic 3! '{- that OE3 il 678 =!, Acid chloride ilH2H a3 <-C1 Na0 &:: kb '217..227 / 0.05'?: 1..22fp, p5 74.69 1 .. 3.1 '' 678 Acid chloride NaOIl 'k' ti 21? .22 ? / O, fJ5! 7 / .69: 74.82q, 65 9.92 3.351 3.12! ! 1, lJ.no16ique "! <Yrr '=',! 1 CCE-! ! > i i: 1 ue of help C # - ') j- \ l, JJ zie.9-2 i rô I 0 1 3 ,. ".



  679 Acid chloride EC: 0 219225 / 0.051 78.40 7, 7 O 10.1.;. 6: 10.72 3.39i 5; 1-aj. linoleic -S¯ 3 OCE = '1,680 Mi. 7a acid chloride, ç i218-232 / 0.081 78.40 78.52 10.4-8 1- :) rt'k #; 1 ..



  : linoleic '*.' i, 1,! 1 1 "1 68l. ¯ NH2CH-Q-oCH3 llaoe k Acid chloride, ï 216-229 / 0.07 78.40 78.62 10.48 10.69 3.39 3.19 linoleic == ' Jino1éique --- CH 1 1 d. F

  <Desc / Clms Page number 134>

 
 EMI134.1
 ! 3 1 '1I' '' '1 i ", 682 oleic acid NH2 & -Q-C115 3 KaOH k, b! 206-221 / 0.06:!; 81.29 81.42 11.45 11.65 j', 39 ! 3.19 662 'Oleic acid NE ÔIÉbcj NaOH lkb 206-221 / 0.06! / 81 29 1 81 42 11 40 ll, 65 3.39' 3> 19 682 .. acidQ oleiqt: 8 NHCH 1 C2i'fs NaOH 81.29 81, + 2 'Iii 11.65 3.39 3n.9 1. 1) 1:' '= i ¯ i 1 j' 503 Acid chloride 'i 1'; CH-o-C2! I5 i fia ° tH [k, b. 2O8-225 / 0O8 '81.4% j 81.51; 11.55 11.62; 3.28 3.08: oleic' C2II5 - 1 e ij,) É to "; ; 1 i j [i; f SiGL '': oleic Acid chloride; 1T3CHJ- K-, CO, 12223-235 / 0.06; t 67.2t 67.39 9.05! 9.23 3101; 2.89:; [; 4:

   LnI Acid CbJ? CH-Q- CO} 223-235 / 0.06: 67.24 6.69! 9.05! 9.23 3:01! 2.89. 'oleic -1 fil' "680. Chloride leioUe i XH ± CH- l 3 Oyez II '! ii 11,% - 1% 4fi G85:! Acid chloride NECH - CH- NaOH 200-215 / 0.08 80.73 80.88 11.83 11.96 Ghlox = acid ure fit! 200-21 f30,? 3 8 3, 96 - 9 3 6B5: Acid chloride! "3 BaCH 200-215 / 0.08f 80 ,? 3 80.88 11.83 1], '961-3-tjJ isostearic CE t JI ..... i .. "fIt ....-- t u! - P- Ù (5) 686: Acid chloride 1 '' i" / 209-230 / 0.08 81.33! 81.42! 12.11 12.35 3.06 294:

   Acid chloride r-- '3! 23pfp 08 81.42. 3bzz: ::! 686; oe. of NH2CHOC-eH3 acid; t. 1209-230 / 0.081 81.33 81.42112.11 12.35 31061 2 ..: 1 -isostearic \ ...... i C-t1 CE, 't3,! ' é: 5 3 there! j)! t ':' 6à7 'Aciàe chloride / Î WLCR ± # - mµ µ Î Î Î 74.02 74.22 10.43 lO, 60 3.32 3.16 657 "iS Stearic 1; i 3 s FI? 4 , 02 74.22 10.43 10.65 3.32 3.16

  <Desc / Clms Page number 135>

 
 EMI135.1
 ##. - - f ¯ ¯.-¯-¯¯ ¯-¯. ¯.¯¯.¯¯ 1 1 r.¯ 688 Acid chloride r i NH2CH --- Hr ¯ N CH3 a 218-22 / 0.07 66.95; 66.99 9.44! 9.61! 3,; 2.93 isostearic iscst6aric l I}! i !! 1 {Il 1,689 Acid Chloride! = 'G'H pCg3 NaOH k, d f f 21% -22' / 0 0> 77.64 ?? 81 J 11.34 11.51! 3.35 3.16 '689! Nil acid chloride 2 om Bath k, di 217-227 / 0.05,' 77.64 "77.81 t Il, 34 Il, 51 3.35 3.16 t isoster3xic M3 J, III '1 690 Acid chloride:

   CH-o-OC2H5! Nc1cH3 fH3 9--230.3 78.14 d 78.32 1 Il, 53; 11.68 3.14 307; isostearic t 2H. 3 '. i 1.



  691 Acid chlorine! --- OC2H \ N 3 CH CH3; a. 218-240 / 0.0 '79, 61 79.79; 10.18 10.31) 3.29 3.8. linolenic CE, z-5 ... i :: 1 ....,: '? : .. 18! ': d f Chlor vre Ranz lit; 3.29 .u.



  692 Nu Nid Acid Chloride 212-225 / 0.07. '79, 61 '79 77 10.18 10,; O! 3.29 38. iinolenic III! ::.: r i xinolenic c I '' 3 i '! C5 l 'III 1693 i NH2 -Q-eH3 acid micride 2OO-225 / 0.05 81.97 82.23 10.4'su lot5s 31514- 3.19 linclenic 21CH l1no1éniqua: CH'1 1! i! 'J f 3': 1 ::. 1 ...

  <Desc / Clms Page number 136>

 
 EMI136.1
 vs . ".) µ j] 1 (i 694 Acid chloride el" 1. Ô f 201-212 / 0.03i 1 1 9.14 9.32) 3.36 3 694 Acid chloride i CH-Ó z11 I 201-212.10.03i 75.05 75.24 9.14! 9.32 3.36, 31'26 3! ) i 2 3 j i! ! J201-212 / 0! f 75.05! 75.2. ; 9.14! 9.3, 3.3. 3! l !!;! 695 oeoerei'vde / j * hiE) ¯ j Na H 1 j (a cG -21 0 O 1 j)! Iin oil; 3 5% 1 / - If; : i flòrured'j ± de ū! NaOE: 1219-228 / O.05 / / Ii.



  ;; 96 'ÎS' -O-- 3! OH i! b i J2I9-228 / 0.05) '' linseed oil 1 CH3 i: i ::.! f fi :, he ,: 69'7: Acid chloride! CH-Q- # 3 1 l! BaOR k i 218-233JG 05; 'j! i .... i 'car oil - f' 'Ii! . ". 1 '. Thaa ...:.:.



  1; haunts CR :? f .., .. ::: ... 1> E.r! Îldd'ÉÀÀ 'J $ I! f. 1.



  698! Acid chloride: j f NaOH k, b f 2J.8-228 / 0.05 .. fI.:. f: carbonan oil, C, H); é o..s'! If 1 Ii! i 1 '1 t 1! t! .. ". .. f 1.



  699 Acid chloride gas i Kco, 1 to iej 'Î 2zs-zz6 / o osl 699 Acid chloride: CH-' "IS! C03 121.8-226 / 0.051 d oil car-! 1." == 'oc H! 1 f 1; heme 1,., OL 2 5 fI

  <Desc / Clms Page number 137>

 
 EMI137.1
 - ## ## # ## # - # - # # #! ? 0o! BBpCH-Br Acid Chloride 1 '220-231 / 0.08} f 700;

   Acid chloride K2C03 c 220-2} 1 / 0.08 safflower oil: t 2g5 "" It! C¯R 1,701! NH2CH.Q- C3H acid chloride .... ¯ N fez! 216-233 / 0.05 i soybean oil C,% H- 1 3! ! 702 BHCH-CC.HQ Acid Chloride! ; N 702 Acid Chloride: NR2CH-Q-OC4H9, i)! 215-236 / 0.05 24 "9 'Nesol Tour-C3H Tour Oil? 703 Acid chloride j ci NACH 214-e-26 / 0.05! ! 703 Acid chloride CH -Ó- '1 Cl CI 1 NaCH k, c; 214-226 / 0.05 Castor oil Castor oil J "! 3 = 704 Acid chloride CBQ-oë5 1 ti Ira OH t 1 tk, b 219-229 / 0.05) CH3 oil = i) 3 / T "\., 705 Acid chloride NH2GH --- OCH3 'g2CO3 k, d 223-234 / 0.05 cottonseed oil! reads 3 ¯¯¯¯¯¯¯¯¯¯¯., L ####### ī¯¯¯¯¯¯¯! ¯¯¯¯ # ¯L

  <Desc / Clms Page number 138>

 
 EMI138.1
 j [Nliccil -hue acid chloride; % Co 215-232 / 0.05 d olive oil -C! 3 3 215-232 / 0.05) 706. gwge + ggiie% c3 d) 2l5-232 /, 5 Acid chloride CH! CH :;

   / 3 7C? Acid chloride lOE2CH-f N CE 3 S 219-227 / 0.06) peanut oil CH J OE3) 3 203 Acid chloride CH-o-OCH3 / 1 ' <S- aij "of locust oil; Ce5 == 3! I Acid chloride at / Cil 3) NJ e 233-245 / 0 * 06 709 duS'ca- 0- 24.06 of chrysa- oil, ; 1ide 02H5 if '"cH- 3 t>) OCR 710: Acid chloride N1i2CH- <"'' i 228-241 / 0.05! of shark OE3 711 1 1 J o: acid ure NH2CH-o- C5! J! 1 K2C03 209-228.05 CH- J sardine oil ¯ C "3

  <Desc / Clms Page number 139>

 
 EMI139.1
 1 - - - a ---------------- i .¯¯ ....... ¯ .; ! 712! Chlorinated acids, 03'-By.

   KOH 'Tc.b 218-220.05 <! rhlor-are ac; id: rice KOU 218-224 / 01.05; of sa- '== quereau 713) / Chlcxnwe KOH k, c l9 @ 219 / O, 05 7 1 Acid chloride - 1H2G: i kob Ic, e 194-219 / 0,0.5 - Wht; i .3a de hereng OE3lg3 1714 1 Ô Chlomine decides '1 NH ± 6JI' fl & 199-23l $ / O, Oo j of oil a.3 c3lirvl. µll 715! <Chloride 3'acid NHCS "-CH- 3; N 1 t 198-224 / o, 05 1715 of oil-liver lOE2CU - (/ (-'a3 '--N--' 198-224 / 0, 05 of cod liver oil C, x9 J15 Acid chlorine XIIOE- 0 in f 193-2Q / O, 00 15 Acid chlorinated NE., CH-- 3 N 193-242 / OtO5 of oil m 'ôOÙ ç oil mulut fiI3 OCR 717 Acid chloride NE x 2 00 eu is3-239 / a, 5 from hu-ledemehhaden!

  <Desc / Clms Page number 140>

 
 EMI140.1
 ci% 18 g âaleu ¯: 8 3 bzz 199-235 / 0.05 of pile oil. * -! \ == * 199-235A? Fez i1iii1i1idt'iÎ'iÎ 2iJJj '3 z) -? /.

    j ronecttt C,) BL 1719 NHCH- Aid Ch3oride. 'HaçH v 200-233 / 0! residual oil on 3 OC2H, 5 200-233 / 0.05

  <Desc / Clms Page number 141>

   Example 720
For 12 hours, a mixture of 14.9 g of methyl linoleate and 10 g of [alpha], p-dimethyl-benzyl-amino was heated at 180 ° C., removing the methanol during the reaction. After the reaction, the reaction mixture was dissolved in 200 ml of eth 2 and washed with 5% aqueous hydrochloric acid solution, to recover about 2 g of excess amine. The ether layer was washed with water, dried and distilled, to obtain 18.9 g of a desired product.



  Elemental analysis:
 EMI141.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.55 <SEP> 81.58
 <tb>
 <tb> he <SEP> (%) <SEP> 10.90 <SEP> 10.99
 <tb>
 <tb> N <SEP> (%) <SEP> 3.52 <SEP> 3.49
 <tb>
 Examples 721 to 800 are shown in the following table!

  <Desc / Clms Page number 142>

 
 EMI142.1
 ----------------- - 1¯ ------------------------------ ---------- 1 ---------------------- .---------------- ---- Temp- Duration -C R56 g EX. ' Ester on! ## - '= Fx. B glyceride RMOAI = Amino fraction; lyseur, & action. oc / = lis ¯ ¯ ---- - --- yc r e; A: yseur: react; ionir ac on Tbéo- Analy-: Theo- Anal Theo-fAna (hour.) T Theo- Analy- 'Theotics: Theo-; Ana-; ¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯ {¯¯¯ J¯¯ ¯ ¯ (From):

   (hours)} tick tick tick tick: tick tick ¯¯ ..... ¯¯¯¯ ... ¯.- fI. he! ; # '? ! i i - ## -. #) 1 j ####. '721 Acid C "3! Naos 3 150! 200-21510.02 (8.55; 81.73. 110.98 10.98; 3952 linoleic 3 2 d! JNaO #!! 150 4!} 200-215 / 0.02; 81.55; 81.71 10.98 j 10.98! .J 3.52) 3.



  OE3 1: J 722j Acid Chez NI2C ',. Ti CFI 175' 208223/0 0.5 81.55 8lt77 10 "90 1190.5 3v52; linoleic 5 i = '3 fi 81.5581.771 10.90 11.05! 1 3, CIl Ii! 1 1! 'J23.cf.de CB, s = NH2CH ¯ - .80 12 201-209 / 0.03 81.69 = 8I, 82 11.02 11.4-0 3e4O 3, 1 linoleic 1 ..! Linoleic! -5 t 4:.. W ':!. CI I80! Z-, 69 f!' 1 "ilinoleic 3 t â 180! 21221/0, O6: 74.69 74.82 9.65! 9968 3.35 '.1: ..,! I 1180; 74.69 74.81 9t7O 3.35 3.2 fit. fIl 1 '7251 i 1 Jcide 1 ;. CZI5NH2CH 1 dl 180 12 f '; 221-221 / 0.051 t I! 74.69 1 74.81 9.65 9.10 3.35 3.2 linoleic CH7: 1 d! ! f 3 IiI 1: l,;, r .. i ...... ¯.,. ¯ ...

  <Desc / Clms Page number 143>

 
 EMI143.1
 



  } # - - - - #! j! I! j 61 Acid ICH; II! NH2CH-o-C1. 180 12,111-231 / 0.06i 14.69; ? 4.3! 9.651 9.77 r 3.35 3.26! . linoleum 1 J jn2 --Cl 180 i 12 J217-231 / 0.06i? 4.69. 9.65 t 3.35! 3.26 linoleic OE3 linoleic! j :; 1; t Ii! 7 Acid '. cg3 !: NH2CH Ôc !! Cl 0 - lso 12 i "218-239 / 0.06:. 69.01 69.31 8, e9! 8.81 j 3.10: 3.08 If f: linoleic l in 3 = Il!;; Il!, Acid! Cs, uf 175! 218-233 / C, 07i {j! 67.52 8.72 ii 3900 B Acid j 3: N1I2CH-Q-Br 1 7 5 14 218-233 / CtO7 67.52 6? A'72 8, '2 8.92! 3.03;:;, 00 linoleic' 'H linoley M3 \ / lit 1 Acid! CE- 2CH Br 175, 216--2z9 / O, 0'Ji, 6Î. $ 2,', t 6'a ?? 1 8.89; 1 1 .. #: linoleic 3 CH-t ": '! Acid CEL 1 -6 175 216-232 / 0.08; 67t52 67.70! 8972 8.83 3.05 ... linoleic "! 9 days CH-z.



  .c.do .i5 z.4 I! 1 8.93 linoleic 'ks, 1 W2C 1 175 14 214-234 / 0.07' 68.06! 68.3l 8.82 8193 3994 2t? 9 linol-Sique '= fit, linoleic 1 2115! ¯ .... ¯.¯¯¯¯, .., .. ¯¯¯.,. ¯¯..¯., ..... ¯¯¯ ..... ¯.¯ .... .¯¯ ...., ... ¯¯¯ ..., ........ ¯¯: ..... ¯ .... ¯¯ ......... ..¯

  <Desc / Clms Page number 144>

 
 EMI144.1
 732 'Acid! 1 x 175 'j 1 81.55 81.61! 10.90 10.94 3.52 '3.32: 732' Acid N $ CH -.-- 2o5-224 / o, o5 81.55 & 1.61 10.90 10.94 3.52 3e 32 linoleic 5 ; f? - * /. l (l i.>) Î. '"1 l" 733' Acid! ; i CH3 u 'NH'H 3 / \ -; 175 14 '216-229 / 0.06! 74.69 =? 4, ô1 9.65 9, $ 1 bzz 3.35 3.30 "0înoléiqpe Î CH3 75VAcid) CH 'tHµÉÉ-ò 1 l? 5 20> -22? / 0.05? 4.6> ? # ,? 9 9.65 9.82 3.5 '3.15? 3-t Acid CH3' t2 H \ ¯Cl - 175 '14 215-227 / 0.05 74.65 74.79;

   z 9.82 3.35 t. 315 '' linoleic! OE3 liPleioUe O # - 73 ') aEcid CEL I3H CT3 3 iNaO C "3 zz 219-231 / 0.05 78.40!' 78.62 10, IL8 10.62 to 5 * '') 'linraLeiqute CS3? 3 / toell> ié.que) ii iéi 5) <JJ ''. i? 5)? 8> #? 51). )! 3> 39 ... L.



  736 icK3 acid 3; i NH2 # H t bzz 12 217-232 / 0.08! 78.40 78.51 10.48 10.61 bzz 3 ... t.



  .linoleiqua j "! 3 ==! :: j: '737 Acid CH3 NHÇH - * - eC3-! $ OCH3 150 ± 23.6-229 / 0.0i? 8, LO? 8,> 1 10.48 10.66 3.39 3.2? 737 * i * ,. c: Lde CS KOOE3 150 216-229 / 0.07 78.40 178.51 10, IkS 10.66 3.39, linoleic ji CE 3 Ù

  <Desc / Clms Page number 145>

 
 EMI145.1
 acid OE CH 3 145 205-22o / O, 06 [81.29 81.43 11.45 ll, 6% j 3.39 3,% '738'Acid CH3, CIi - C2H5 - ± GH3 145 21 205- 221 / 0.06 61.23 =: 81.43 11.45 r ¯ 31.64 3.39 3.3 'oleic i 173.91 Acid OE 3 im-oe 0 05 t rraoBt 135 4 z 2o7-2z2 / o, o? - 81.44 81.61 11.55, 11.59 3.28 3.18 oleic 3; 2 5; 74oJ Acid OE3 '' NH # - Br -! 160 20 219-233 / 0.06 67.24) 1 6? 4V 9.05 9.23 3.01 2.95 oleic C "3) 741 Iso- acid: CH 'NC3- <f-CS 165 80.73 80.89! 11.93; 5.49 34 J!. ' Iso-Acid cH 1,165 18 '199-221 / O.0? / 80.73 80.89 11.83.11.93 3.49 3; '34:

   stearic jµ * eue 5 j ::: tu / - \ i - 3 00, 742 icide iso- i 0- - 175 18 205-230 / 0907.1 81.33 81.51 3.2.1. 2- Y- 3.06 9.5: stearic .2 \ == / 743! -leid iso-) m- 70-ci 175 2 -234/0005 74902 74.11 10943 10.51 3932 3t3O 743 Acid iso- NBCH - ci - 175 230-.234 / ü, o5 74.02 74.11 10, 43 10.51 3.32 3.30, 'stearic) 21J9? )>. '. >. .> j {.w ......... rr ...-. w .... ww-.r.-.- .. rar.r ... wr.rr-r.,. m ... rrr..nr..r.rwrwwmrr.r.¯sw¯..rrnrmrwrrs.rar..nw.r wi .-. nrw .... r -.- r.-v .... .rw, ... wr.wwrw ... r..ww..rswr..r "". wv

  <Desc / Clms Page number 146>

 
 EMI146.1
 bzz, ¯¯ 1 '. f, j 't t, 744 Acid iso- Gas = NCg 1'S 9218-238 / 0 05 66.95 6-7.09 9.44 9 61 1-3.00 3101; stearic! f-0- <it 218-238 / 0.05! f 66.95 '! ! 67.09; ; ! 9.44 9.61! 3.01 'f: f t 1 fI! , t f t t. , j: i ': l, J. bed ; ? 45. iso- cide M3 M3 175 16 '217-3 / 0.0 ?! 77.64 77.77! : 1I, 34 Il, 5 <t- i 3.35 ± stearJ. that:

   M3 It! ! 3.1? f;) i l 1! irr 'f:!: i ..



  If 'f' 0-! - =: ': J j! : 175} 16 19-233 / 0,! 78.14? 8.31 11.53; 11.61! J i. ' 3.14! j f 3.06 1746 Stearic Acicia ise- 1 tk '? C / -OC2H 175 16. 2i9-233fo, os J: 78.14 78.1 t i 11.5: 5! 11.61 i 3.14 '3106' stearic! r TT fil 74? I..lcide J.1DO-: CIL 1 Jm., # - Ó 5 '1 -! 180! 16 2lFs-2 79.61 79.66 10.18 1031! 3,291 3. Lenic W'3 180 -238/0, - v6l 79.68 10.18 10.3.-t 3 29! ï .... '¯.: ¯11 Ii ..



  7481 lenic Li no-CH3 iF f 6C1I-Q-oCH ,; 180 16 210-225f0 '06 79.61 79.67 1 10.18' f 20.51: 3.29 3se tti, lel.11. That! ...



  .1! -l'j 749, -lino acid - m NFi2G - 3 -; L 180 16 202-222 / 0.05 81.971 82.03 10.45 10.54! 3954 t 3.31 d lénjquo # 1 fi! i: f 3 f:! He! f! f

  <Desc / Clms Page number 147>

 
 EMI147.1
 He! 16020202 / 0.03 75.09; 75.19, 9.14 /, 9.23> 3.36 "3.08 750Aciaelino- i CH3 NHCE 160! 200-212 / 0.03 75.09 75.19 9.14. 9.231 336 3.08! Lenic CIL ft 'le QUe t yarn il' tIf! î51'-ido d'hui- '- 155! l If i; le de lin d' hui-f; CH3 1 CH: 155 î 1: 203-216 / 0.061 I! 1 !! 1 \ - 3,, 1 "[CH j 1 52jAcid! dthui-: fi:; "1 CH): cH0-: Cl: i - 160 20 J 218-232 / 0.05!!: Flax CE5) 1 - 1 16)! 2.8-52"! 1. f CH), J wire J! Ji! j 'O 1' - j i '53 Oil-CH acid,! 1! J! 160 1! 20 218-241 / 0.05! He! 753AC: today-ICH3! LCH '= T! - 160 20; . 218-.243./O,OSÎ 1 ""! The of card- 3 ¯ t \ == / 3 .... 1 1thaIae CE ;? Ji: fi:

   Ji. th-e Key5 ... Jo Acid. l '1 Cvh3 iH2CH-1 (bzz, 1 i! it 160 f, .. 1 .. 1 t' s4jàciàe to, "oe 1) XHzE ± Q - j 160 18 'j215-2 & 9 / o, 05µ 1 j; jj, jj: fl., j OO le de -car- fil CH ... thame C2H, 3 i 1 1 fi .. i: 551 Oil acid-Î 0I! 3 CR.r \ (d) - j 160 215-230 / 0.05 here reads 1 55. Today-CH.

   NH2CH- 160 ji 21.5-2300,05 'le> - 1 *% ilocz, 1 "' / 'l,! Thane le de car- 5' = (. 00 2 -:;,! IL 1: i! Ii , "; 3 1 ¯¯¯¯¯¯¯¯¯¯¯¯¯¯

  <Desc / Clms Page number 148>

 
 EMI148.1
 756 Oil acid of CH3 a NH2CH - Br - 160 18 220-241 / 0,05 756 j î 1 1 tx1aael- "'t / 16o) 22" "' 'safflower C, HJ 757 Oil acid do CH3 = 'IPH2CH - C3 175 18 215-231 / 0.05! Soybean C3H7' = 758 'Oil acid' i C3117 130 '209-233 / 0.05 758 sunflower (the 3; 1 IZH2CH - CC Hg '' s 130 L2 = cOQ-233.G ,, US: = sunflower .3 - \. J ^ '4H9 C3H7! 759 j Oil acid of 3,) 1. É "l1 /' 37 180 14 212 -228 / 0.0.51 Î59 castor oil; .le! j NH2CE i 1fez0 y Oil acid of CH3 2115 i 'KCtBu 145 z- 213-228 / 0.05! colza es, '= colza CE 3 6i' Oil acid CE, NH # - OCH, 180 220-234 / 0.05J 761 cotton of oil! NH2GH-- 3H7 loch3 180 220-23 / 0.05 d;

   C t C, H 3

  <Desc / Clms Page number 149>

 
 EMI149.1
 jc> e-1 Oil acid CH 3 C213 z 12 215-23E; /0,0.5 olive! CH3 '-7 763 Oil acid CH 3 NH2; H - pCH3 i 180 12 # 219-229 / 0.05 ± peanut 3! ff \ = / peanut .. CH3 "-3 764 Acid dlhtilp OE3 OCH3 180! 3 12 219-2 33 / a, 06 from locust" t # -3 rice Oil acid / "3 INH 2 OEe ci 175 z + 229 -2v5 / 0.06 from chrysalis j 3 d 2, = / OCR 766 Oil acid 1BH2CH Cg - 180 J228-241 / 0.05 766 from oil liver 180 IL2 228-241 / 0 from shark liver Ù / 767 Oil acid NH # "- 0 -! 175 209-231 / 0.05J 767 Oil acid z3) *% 11 /> - 2>) -) j 75 - "/??! Of sardine 3, 7 OE3 j 3 1 .. ¯¯¯¯

  <Desc / Clms Page number 150>

 
 EMI150.1
 768 # BHCH-¯-Br # 180 Oil Acid i 'i 12: 216-227 / 0.05! 216-227 / 005 7E> 8; mackerel.

   CH3 NH2CH - gr 180: 216-2270.05; Daquereau 1:; t fi 1 t; ! : J f 769 'Acid of hïtil r mCa-. 135; 154-219 / 0,0 '- 769 with oil acid (CH lllicE' Na0Et '1µ5 (Î l54-219 / Ô, OSÎ ",; herring f - çg f 3 1 (t' 'CH i. I 770 Lcide drlc C3 NBCh- '-0 200.' 770, ': ": id, cPh'D.le of' J, CR3 - 0E5 ¯ a.ti-0-c4H9" i 200 10. 1-2ql / O, 05i Sd.UJ: '¯- CH 1 ..;. I J.! Saurol' 3. 'Î J. iti, - 771 f. J ..1.cidc of oil i! CH3!,: RCH # 3 Jr \ .- 210 199-225 / ù, 05i. 771 Acid h-cilode C3 'F ZTH2CH- CH - 210 139-225 / 0.05 toiedenorue 1 liver of norue tiri ± C4g9 if;.; 772! Acid d 'oil 1 OE /. / Î -) f 165 1 16 / i 19% 2WQ / 0, zero ooi: t3' 1 fi! t µ3 1/773: Oil acid of] 0E3 = h'Fi2CH OG 1 - i 160,18,183-239 / 0.05.



  ; nenhaden CHx 1! '!

  <Desc / Clms Page number 151>

 
 EMI151.1
 / 1?> J) gjµde 1 (1µµie df CH-!! 1 Ô j 1 - 150 i 18 l; 202-240 / 0.05; 1 pleuronect 1 1 pleuronect O. "5 ft TT! 775. 3 Acid d 'CE3 CHfi "" \ - ociI5 z -... 1L: -5; 20 2OO-25/0, 05i 775! CB oil acid,! NRS .'.- MH-. -! 15 200-235 / 0.05 residual tf fi! 7'16! Hui1'3 ds lin.: N1l2CH: -: '80 16; lo / t-.21e / O, 06 776!! Linseed oil 3 1;; 130 1 1.218 /0.06 1 t ', Î 777 Linseed oil NS2 # (;) - 1! - 1 180!' 1.6: 200-232 / 0.05 5 778 Coal oil1; hame: W OH NI1; 140 4 1 1 J .99-2 ;; 9 / C .041 'z)' aI3 / "'Î 779 Carthane oil;

   BmCH [] Hp. 1 4 5 202-231 / 0.05 Î 1 niJ.e * .1 FQ ¯H- CR, H31! 04! J.45 202-2}: i / 0, 051

  <Desc / Clms Page number 152>

 
 EMI152.1
 ]]] 780) Safflower oil, j Q 1? 5) 2OE-240 / 0.05]) 780 Safflower oil *** "200-240 / 0.051 'Oil Î i NHZC,' H 3" Ce-5 1? 5 i; ? 81 Safflower oil NH2GH-- Br 1 * 75 12) 1 zo, -5 / o.05)! ' 781; Carthane oil 175 "1 ij! 203 235 / 0,0 '782 Etil.e de soya i riH.2cH - 3g? 170 21 i 19s-z33 / o' oµ 732 Buile soya 1 3g? 170 198-233 / 0, 05 'jt 785 Sunflower oil mI + ±> r.1) -)' 1 175 21 '199-235 / 0.05!!! C3H?! - 784! Castor oil NH2CH 175' 21 3; 1202-239 / 0.05;

   H3 39/5 / Rapeseed oil NELCH -'- OCS.- - 175 '' 200-228 / 0.05! '785 Rapeseed oil 1 L 25 175 22 t 200-? 28 / O, ÔS L .... J. 1 1 '' ï '[: 0 j, i> to>, j

  <Desc / Clms Page number 153>

 
 EMI153.1
 786 H-. 3. Cotton i f NJLCH -0- OCIL - 175! 23 1208-235 / 0 t, t05 C3H? - '1 f Ii t f 1 i' l8? ! Olive oil NH 2 CH j "'C5 175 21' 2CO-236 / 0,04J C" 3 i 7S8 Oil dl of NFi2CTi 1 r ocli - J 180 bzz? .GG-2 + jO, C $ j il ± : "'oi 1 t CH3 = 1 789!! Locust oil 11 OeIL - 160! 22! 200-233 / 0, C5! G2H $ ... 1 CIL Ii fI C" 3 Chrysalidoi oil NZ> Cfl le 145 198 -'- D44 / 0.05e 790! Enilc declii-ysalidej NH? # L¯c 145 198-244 / 005? 90 Huila chrysalis! C2H5 145 198-21 <4 / 0.05;

   C-3 lu Liver oil from rTg2, CH 3 155. 20 212-242 / 0.05 i ftur

  <Desc / Clms Page number 154>

 
 EMI154.1
 ) i 9 sardine bubble 2 G = H 'OC., H. 5 = H 3 BO z 4 20C-233 / C, 05 -OE3 793! Naquerel oil 'NH2CH-- i6 20 198-232 / 0.04.



  ) '1 j * 4) = 1,; -XzOOE3 ;! 450 190-220 / 0.05) GI CH3 3 795 Saurel oil l # CB-CJ 15o 24 / j i94-î41 / o, Q4î 795 Hu3..le surel NH2CH - '' 1-C4H9 l50 19--2 + 1. / C, EJr \ === / j [j 796 RHCE liver oil -) "1 150 jjj 1 j 190-225 / O, C0j 795 Huila liver NHp # H3L 150 193-225 / O.C5 morne norue C4% "= 797 Null oil f - OCE3 z 180) 12! L95-242 / 0.05

  <Desc / Clms Page number 155>

 
 EMI155.1
 f - "'-"' - "'---------"' --- "'---------"' ''; '' '' '--- --'''-'' '' ''-'' - ''-''......., .....-... "" 798 Monlmdon oil 210 10 Ë4l / 0.09 199 Oil pl <mrc- va 0.6 m 10 16242 / 0.09 aeota 1 \ :.} 000 JlW.la ... t4 ",, 11.

   Ml: 0Jl-Q- LO; JJ, 160 10 200..f2 ,, / O, O, ¯¯¯¯¯¯¯ .. ... JJ -.- ----------- -------------------------------------- "- ¯..u. ----- ---------------- ¯w-

  <Desc / Clms Page number 156>

 Example 801
Mowing 8 hours, using a water separator, we carried. at reflux, a solution of 14 g of linoleic acid, 7 g of [alpha], p-dimethyl-benzylamino and 0.5 g of p-toluenesulfonic acid in 100 ml of toluene. The reaction mixture was washed with 5% aqueous NaOH solution, 5% aqueous HCl solution and water, then concentrated and the residue distilled, to afford 16. , 1 g of a desired product of a PE of 203-216 C / 0.06 mm of Hg.



  Elemental analysis;
 EMI156.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.55 <SEP> 81.71
 <tb>
 <tb> H <SEP> (%) <SEP> 10.90 <SEP> 10.99
 <tb>
 <tb> N <SEP> (%) <SEP> 3.52 <SEP> 3.42
 <tb>
   The oxomplos 802 to 856 are listed in the following table where: Condensing agent:
A. p-Toluenesulfonic acid
B. p-Toluenesulfonic acid chloride
C. Sulfuric acid
D. Phenol-sulfonic acid
E. "IRA-400"
F. "Amberlito-15" Solvent: a. Toluene b. Pyridino c. Benzene d. Chloroform e. Xylene f.

   Carbon tetrachloride

  <Desc / Clms Page number 157>

 
 EMI157.1
 liapr4rwrr3rrr..rrw.wr.rir.Y, .... araww.lYfwrwr.rr.sIWYLII.wr.Ywri.whwfYY..rrYa..Y '.. s .¯ ... rso.lcriw / i. ... rW r.rcrriL1'.Www- .. ¯¯.rpy ".wrrir..GC.4scGl: .aYraüaS.cJfYitYl.ïGwaSC.cWtlflülcwi; iCiP: WicwiiYOCIii 'om-,. bzz i 0 Ii S'! 6Bt **, lesta Ami 1,801 .... 44 la t - "'' '' '' '' ''. '' '' '' '' - '' '' '' 1 '; 1.w 'r Aoidw is 1 J!' 6a.ctiÙt11 C / 1 \ 1fl tr; i Th6o ...! Amly-1 21IL60- - Anly- Tho ...

   A.nal7- --- 1 ----------------; ± ii, r3, r <a ique 'iqu & ciqut tique r <0! ' ! .1..LL l'4t 02 1 Aci41 lipidic 1 mf.a t A &6; 199-210, OS 81, 81, 10.90) 11.11 3.52 3.46 f! 03 Aoi4cliMl6ique 1 (d) - A -. '3 i, Ël 10.90 11.09 3% 52 3b4a Â014.0 111'10161q'1o rmayft'-T, 111. "Sl.M 10.90 11.09)., A J,'" 3WC cm is ig :; .; ; Ââaliat9; 13? / E µ19 n, "1 1 .. \, l'II? LlS, t \ Z3f -".! '' '' 11 thread A9m HMKitM b a </ 9.6? ? 4.69? T.M 3 9.69 .S 9.ui.



  \ Br l ', 1 "11111 A) HasitM Eiëë.ee? T, 69 1" --- ## rr.mmnrrTT # ¯- * T - # - T-! Nrr ###' - "--'- * == '--- # - r ---- - # -'- - - -: - * - rrr .-- "# - TTT - tT - * -" -' "! r '"" "; - == - 3. = # = # .R- * Tf.: Tr # (TrmTt

  <Desc / Clms Page number 158>

 
 EMI158.1
 4 ----- .. 11. ", -" ,,,,,,,., -...- --............ V-¯¯.A1f .1 ----'- ¯¯118. <1 VII ..., .. 1.1. "..--- t ---" "-" "-, ...., .. V-" '' '' '' "" 1 '' '' '' '. r "¯", 807 ï 1% H ± FCi) 1 B) (b Î ï 18 /; 2l6- * l /. 5) (? 4> 69) j? 4.79) 1 9.65 1 9.7 tj 3.35 'Q 3> 19 80? Linoleic acid NBC3 - / "\ - ci b! '216-221 / 0.05 74.69! 74.79 9.70 3.35 3.19' c = 'f !! 508 acid CIL 1] 1. t 8, E, 93, 10 3, Ol NR2CE-c. 220-238 / O6.69.01 69.22 8t69 8182 3.10 3.01!; - 808 Linoleic acid! NHCS- "i 3 = -Cl t 'A! , 220-238 / 0.06! '69.01! i 69.22:

   ! 8.69 '8.82! 3.10 3.01 809 Linoleic acid '/ 1 R ± EC ± Ô- 1% 3 Bn JJ 1' -.2 '215-238 / 0.09! a5-238 / o, 09/1 / '67.52 / 67.74 6.72 8.93)' / 3, Q3 1 / 2.98 j J..cidc l1n01éi <r.tO; N1J2m-Q-Br ,, 1 67.52 67.74: 8.72, O}: fil. wire! to, ciàe 1 im2ez-b 1 il; ! >) 6?, 52, f G,? 2 If! 810 Linoleic acid HH ,, C3. 222-235 / 0.1 67.52 67.82 G, 72 8.90 303 2.96-i.

    ol ..:. * 811 Acid llHµFi ± $ 217-2e9 / 0.0W '67.52 / 67.62 / ±,? 2 8.9cl 3.03 2 / µ 631 Linoleic acid IM2 A 16 217-229 / 0.04 67, 52 67.62 E, 72 8, '. K' 3.03 2 "3 :: i1 812 Linoleic acid IM.20n-f *% - mr '1' d 16 220-239 / 0 $ 06 68.06 il 68.171 8,82 8,9 2, 1 2''781 @, 5 ..... ..: "'¯ -"' '' - IIII; t '' '' 'Mii' '' IIIWiI-i & iNIIiIWfi.WAtiOo1 -... G; t .'i> A8i "" "" - ¯ -. JiI¯¯8lī "'8i"' '' ''! Miif ... L..¯-.a .. ..... "¯¯¯¯¯¯J¯¯

  <Desc / Clms Page number 159>

 
 EMI159.1
 # - ## - - - # - --P- - j! 13! Linoleic acid! CH-Q- # 3 B b 1 212-223 / 0.051 81.55 81.75 10.90 j 11.08 Il! 3.52: 3.40! !! ! 3 \ == y) reads 1114 Linoleic acid: NH2CH-Q-C1.

   AT ! e i 16 2118-222 / 0.07 74.69? 88; 9.65 9.76. 3s35 $ 3.1; : g, ¯-.5 j (d) Iii 3.35 3.19 il5 Acid linolei'L.oi c: ao-C1 3.3 f 22s7-.2.v /.^., G6 'f' 4.6 1 74 , Sl 9.65; 9.02) 3.35 3.19 'the' V9 ,, .i: '! Ii "il6 Acid t OG.H3 fIl 6-218 / 0.04j '!) 78.40! 78.80!'! 10; 3.39;.! ' ! 16 Jteide li, oldique ', CH / ¯ g.: A 2 2: L6-? 18/01 ii 78,6c 14-8;. ** "- 1 tfj' fi ... in (L7 0CI3 j 7S .40 10.48 j 10.53 3.1: ugly linolei, that NC 218-229 / 0.03! 78.40 28.46 10.53 3.p39 3119 / * tT! 'I * - j Linoleic acid ** X 2l8-2.29 / 0.03i 7E, t {)! 10.53 1: t 3.1; 1! ::;}:, f! , Lt3 I linoleic acid IOEP- OCR 1215-226 / 01 ,,.; ,, 78940 '78 9 52 10.48 10.62 3.39 3.20 ISLileic acid 1 B b! J215-226.03J 78.40 fit.



  CH3 ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯L¯¯ # L-¯¯ # L¯¯¯L¯¯L-¯¯L

  <Desc / Clms Page number 160>

 
 EMI160.1
 -¯w ... ¯'V r "" "-. - .... 4.



  319 'Oleic acid iF3'! AT ! at ' . 10 205-220 / 0.07J! ! 81.29., 39 3.29 319 '/ # oleic acid 1) f NH2CHC j- :) t a i 10 1 1 i205-220 / 0.0'7ft! 81.29! i 11.45 11.56 1>, 39 3.29 820 'Oleic acid l / µ 2l - 5 1 f. : 3 r F 81.62; 11.55 Î. 'j 3.28 j 3.09 20 .. Oliqtle acid 1H2CH - C2H C2g5 1 ,. 2I3-223 / O, O? '= $ 1.44 s ¯. = 81.62; i:: 11, $$: 'l3, fJ. ¯ t i B21) Oleic acid = ^ - 1-CH ..- B 't B b 18 [) [22 @ 238 / O, 07 / f s 6 ?, 24-; '67.51' Q, 05 (9.01) - 3.01-; 2.89 B2l: "cide .que NH2CH-o- 224-238 / 0.07; 67.24- 67.51 9.05 9.11 3.01 2.89 M3 \ === / fi '1: 5 if! 1 B22 Acid isostéa- = ICH - CH3 1 c! 12 2G0-215 / O, Oi i! 80.73 =, 91 11.83 '11.94 3.49' 5.33 tric lsostéa-! "L-" here 00.73 ! 80.91 111.33 11.94 3.49 3. that 63. ..R.



  ! t reads '"Îl"' b23! Isosteal Acid Î llHjOE ± hECb 16 80.33) 1 1 3.06 '' 523! Acid isostea- NH2CH-QC- #, Ad 16 t 206-224 / 0.07i 81.33 fi 1.52 12.11 12.42) 3.06 d 3, Ol ric "t ## t" 1 rique '+ 5 M3 !! He!: . :: fIt.



  J24 Isostea- '1 i mL9H -0- C1 Cl e 14 2'!. 8-239JUs06 71F '02 74,21 [10' 43 t 1 10, .56 3.32 3.06 'nr ric rique iji 1 , ¯¯¯¯¯¯J.J2¯¯¯¯¯¯ 1.¯: ¯¯ # ¯¯¯¯¯L - #### L ## L - ## - J. ## L

  <Desc / Clms Page number 161>

 
 EMI161.1
 825 ...---. - - j NBCH-f-Br J D 14 215-P:> 6/0905; 66,9.5 67,13 9,44 9,57 39 col 3905 825 kidc isostéa- Í CH "'-Br à' 'à a5-a6, o' 05 '1 66' 90 '6? 1! 9.44 9 07> 'ce 05 826 Acid isostea-SHzOE- 0OE E a 14 208-23O / 0.05 7?, 6W? 7.7 "ll, 3 + 11> 45 3> 35 3.1 @! ! r1q \ 10 M3 OM3 i: 1; , 827 / isosteatic acid, Í CE: -o-oc., N5 3 B / b 20 1 i; i 218-244 / 0.051 78.14 78.37! He, 53 11.68 3.14 3.02 laugh it! ; 1 d 023 Linole acid - NHCH '25! A e 216-230 / 0.05 79.76 10.18 3.0.35 a2S linoleic acid 216-230 / 0.0.5i 79.61 79.76 10.18 10 ,,. 705 3 "29 3bzz. Inique 1ino1- "r ± $ A. 1! 79,61 79, '16 1.1.10.18 lO) 513'29 '3-1> 1.,.: \ M.que OE3' \ J Here, !!:

   mm ** 829 Linole acid- 'OE-Z-CIH- Ne == \ or OCK3 l! l 1.>? ' '79.61 79.75 10.18 10.30 3.29 3il 1,829 nique J.inoU- "!" =' OCI '? J 215-227 / 0.051 79.61? 9t75 10.181 10.30 3.29 inique 1 Iii 830 Limle acid- 1 ii. CR-o- CIL ai 16 212-220 / 0.05, '81.97 1 i 1 82.18 10.45 10.50 3.54 3.47 1 nique 1 ---: J. . 1 CH- - :; ,. ! - 1 1 i. f. 1,

  <Desc / Clms Page number 162>

 
 EMI162.1
 ..---. - ------ r-- ---- .--- ----...



  831: Acidelinol-! ! 4 ----------- "1 i 'j 1, 1. 1 j Î 1 3.33 j C31 i, -cide lin016- moe 10' 1198-218 / 0.03 (15.09 1 75.21. 9.14 9 3.36 3133 nique 1 1! Tif t 83? /Itrd.h <. '"* hrm-CH. g 12 3-2 - = /. 31' 832! 'Oil acid!:! F-03 Fia 1 18 .203-213 / 0) fI.: 2O:? - 21 / 0.03 f!, 83-> rice oil "3 z203-213 / 0.03 linseed /" lU M3 r '! 853'. Acid in oil RHCE-Cl cx) 1 'B Î êûO- 205 / 0.03 f 1 l 833 Oil acid ICE-Cl b;!! 200-218 / 0.03;: i 833,: Oil I.cid NH2CH-Q-Cl B bi 20 2û0-21 $ / 0.03 flax 3 834 Oil acid 1 IICH-o-CH3 f M3 a 12 f "203-215 / 0.03; 1 II! 1 i! he! .... 1: Î 1 'safflower Wear! Safflower l' l CH .... "=" 1 1 i! +1 t i t i 1 ....,. 10 '-:> lit ... goose' y 1 \ ..:.; ...



  $ 35 Oil acid! sorting ..



  835: Oil acid CR - A to j 12! 209-224 / 0.051. : -1; of carthane Î CZI5 t - t f! , 1 t i 1 1 t t 1 l: ..! ..: r 836 Oil acid Here (208-2200.05) t! there! 836 t "- oil eide 1208-220 / 0, Q5; f; ide safflower 1.! - L 2 R .. t 1.; F. !!. 1 fIl 1 1 1 l. L 1 I-- -------- '- -------------------------. -

  <Desc / Clms Page number 163>

 
 EMI163.1
 1 Î 837 LiH2CH-- 8r e z- oil acid 220-225 / 0.03)! carthano 'Ô' # 5 j 5/0903 838! CH / C A Oil Acid! a z r-.L% .-- 232/0 538 soybeans d.bniie 37 12) 21 -232 / 0.05 soybeans! . 31 3-7 j) 839 1 Acid of hcilc do f mCsV-OC.Hq to a. 10 208-232 / 0.05! sunflower! "ib 'i 1 WF0 hvilô ci acid 205-225 / O, Q5 P, 401 2G y-Ci c oil acid, 20-225 / 0.05! castor 2-05-22 841' ethnilo acid t 0Cg;

   d) 22O-229 / O, 05 841! Oil acid fU-C- () C2H c 220-229 / 0.05! rapeseed il '' i uV¯ / C "3 842 Star acid from) '13) j C5 12 j 1 '.4, OCR oil cider, 218-23 cotton = * 3 / 0.05 - -C3H7

  <Desc / Clms Page number 164>

 
 EMI164.1
 ...... bod 1 1 i;.! i sw5 ieide at, bniie µ] a [[>) 2oe-226 / O, 05): 843 Oil acid --x NH2CH-- '' 'E a 14 204-226 / 0, .05 1 d. olive CH- 1 é:! j open j j 3 1 s j J j 844 Oil acid! ! i i Nll2CH-o- i i! AT ! i e 10 1 i 218-228 / 0.05, peanut i 1 == j 1. i; i f i t 1 i 3! ::: r i 1 i C45; . '. cidod'h'lcde ICH - / - (X j.O 215-225 / 0.05! i iJ4.5;: .ciao d. z: anj 10 de lCH'r <y; .a: x 1: ..: .1.0 2: i.5-25 / C;, 05 f locust $ 5 1 itj "C,; I" 1 '.CH3 "ix c46; j 4àcido dbnilc de rfi 3 i 252'2 # l "'5 846:

   ltcido d ::: milo #ICl;: 9 232-2l! -1/0, 05 chrysalis f! chrysalis "2" 5 EYE 84? Oil acid BHpCH- / -CS ocs "! A!! E 225-24t / 0.05! Oil acid CH- -GH e. 10, 84-7; ..1 cde of CH oil z44 / 0.05); shark foio CS3 t * = # j / dd il!. * 1 10 206-220 / 0.06 F34t3 * sardine from J 2g'OC2H5 C 9 d 2 6-22 /, 6 ff 1 CH; t. -

  <Desc / Clms Page number 165>

 
 EMI165.1
 -; ------------------ r ---! oil acid 1 f3,. 1. i j 8 * 9) 3 naquareau 2; ï # a 12 214-23Z1'O, OS i mackerel oil acid NEgOE / -) C f) 194-228 / 0, 5 1850 1 ", oil ide of 1 Nfi2CH-Q CJ a 12 J 194- 05 yc83 \ 3 h3.rcng IIi!] '1 l' "? 2% O 851 j: cidQ. = H; . â3 1 fH - O-C4 a 10 12.07 d 1 saoro1.

   CH3 f "f! 1 ÎlÉ5d.Ù lÉÎl i / µÔ j; / j 'to (' 1 52; .cid.od'3nH.lo do I'H2CH-Tj- t, 'H3 i 12 I9f3-228 / p , p5 fj5?;: t.cj, do d standard dtJ Im2CH L "H3 F 198-228 / 0.05 1 1 4- ') ij 1 f 1 --c- 8 853. \ eUe of oil of 1 Nfi2CH-oO Air 8 193-238 / 0.06 j IlUJ..et f *% 1 / -% f J fj "" / ") 854 Oil acid i, #, 854 Oil acid from 1 CHQ d 12 188-238 / 010511 1 nenhaden 1 188-238 / 0.05 '. 1. OE3 r tif ii

  <Desc / Clms Page number 166>

 
 EMI166.1
 ..Iiod. el 1 there) 855! Oil acid of 3 F NH2CH .. 9 A IcI 12 194-237 / O, 0 $ pleuronecte = bzz) E * '& É ±' <'j 856; NBC3 oil acid. ' '-OC i. 1 200-228 / 0.05: 856: Oil acid # :, o- CiI5 200-228 / 0.05 i residual hµ / ÉÔ '5 r.t ..



  . i::! ..:.

  <Desc / Clms Page number 167>

 



  Example 857
For 8 hours, using a water separator, a mixture of 28 g of linoleic acid, 21 g of [alpha] -benzyl-benzylamino, 300 ml of toluene ot do 0 was brought to reflux. , 4 g of p-toluenesulfonic acid. The toluene layer was washed with acid, alkali and water, then dried, concentrated and purified by chromatography in an alumina column, to give 29.2 g. of a semi-solid product.



  Elementary analysis!
 EMI167.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 83.60 <SEP> 83.70
 <tb>
 <tb> H <SEP> (%) <SEP> 9.87 <SEP> 10.08
 <tb> N <SEP> (%) <SEP> 3.05 <SEP> 3.08
 <tb>
 
Examples 858 to 887 are shown in the following table in which: Agont do dehydration:
A. p-toluene-sulfonic acid B. p-toluene-sulfonic acid chloruro
C. Sulfuric acid
D, Phenol-sulfonic acid
E. "IRA-400"
F. "Amberlite-15" Solvent: a. Toluene b. Pyridine c. Benzèno d. Chloroform o. Xylene f. Carbon tetrachlorume.

  <Desc / Clms Page number 168>

 
 EMI168.1
 



  ¯] the%! Exem-! i; ! Tough; C 7 "7: 1; 7f1,; 1 t Sol- Pro- ¯r Théo - !. Anal7-1: PRO Acid" "É to Àté Théo kwly-1 Théo- 1 ànaly-Î Théo- Î &naly-Î:;;;. (hours) i! ric, tic i1qle tic! ric i tic; 858 1 Linoleic acid 4 (+) 11 t!! b 20 1 45 -50 '\ 83160 i 83.71 / 1 9.87 i 10 , 04 3 3s 05 3.15 D -17.9 i 359 Il 1 (-) e 12 ". S3s60 83.79 l 9tf? ': 10.01? ¯ 305: 3.14 859 aI: 1i.de ::! ; 1 '::,] arai # - s I :! "/ IX D' & ID +16.9 i J i 1 86O> ole1qle acid) ...

   D t i Î c 10 Seui- / 85.2l !. 83.36 10.26; 10.32 3.03 3.14 860; Oleic acid j di () = e n solid 1 / t361 Isostaric acid i dl {t) i i a: .C - f E2.88 = 83.02 10.65 10.4I 3.02 Ù 3.10 1 '862' <+> 'i' 10 - 82 s 88 83.05 f 10.65 10.87 302 3.09 f 863 1 1 (-) j, a lp "i 82.88 1 83, t? 6 j 10, 6.5" 1 lQ '69 302: 3, O? 1; I '863 il' 3.12 ..! . 10! - 85.97! 84.12 9.47: 5.C5 3.12 863 BEi Acid iīnoiéniqic- i dl () A a 10 1 Î! 83.91 fi '84, .2 94? '1 9? 2 {3.C5 .12 865 Oil fatty acid i dl (t) A a 10 Il! flax () a) 866;

   Linseed oil fatty acid d (, ji, 1 A ita 10 IIi t 866 Oil fatty acid carthane carthane!! If: ', 96? Oil fatty acid! 1 (-) AJ a 1 10 . 1 i ¯ Decarthame, t.!! I ¯¯¯¯¯L - ## - J¯-! ¯-L ## J¯¯! ¯¯! # - ## - #### - ##

  <Desc / Clms Page number 169>

 
 EMI169.1
 
 <tb> 868 <SEP> Acid <SEP> bold <SEP> of oil <SEP> to <SEP> (¯) <SEP> P <SEP> f <SEP> 10 <SEP> Semide <SEP> safflower <SEP>; <SEP> solid
 <tb> 869 <SEP> Acid <SEP> of oil <SEP> of <SEP> dl (¯) <SEP> a <SEP> 12
 <tb> soybean
 <tb> 870 <SEP> Acid <SEP> of oil <SEP> of <SEP> dl <SEP> (¯) <SEP> A <SEP> a <SEP>! <SEP> 12
 <tb>;

    <SEP> sunflower <SEP>
 <tb> 871 <SEP> Acid <SEP> of oil <SEP> of <SEP> dl <SEP> (+) <SEP> A <SEP> a <SEP> 12
 <tb> castor
 <tb> 872 <SEP> Acid <SEP> of oil <SEP> of <SEP> dl <SEP> (¯) <SEP> A <SEP> 12
 <tb> rapeseed
 <tb> 873 <SEP> Acid <SEP> of oil <SEP> of <SEP> " <SEP> D <SEP> a <SEP> 12 <SEP> "
 <tb> cotton
 <tb> 874 <SEP> Acid <SEP> of oil
 <tb> 874 <SEP> Acid <SEP> of oil <SEP> " <SEP> A <SEP> a <SEP> 12 <SEP> "
 <tb>.

    <SEP> 875 <SEP> Acid <SEP> of oil
 <tb> peanut <SEP> " <SEP> A <SEP> a <SEP> 12 <SEP> "
 <tb> ' <SEP> 876 <SEP>! <SEP> Acid <SEP> of oil
 <tb> from <SEP> locust <SEP> a <SEP> 12
 <tb> 877 <SEP> Acid <SEP> of oil <SEP> of <SEP> @ <SEP> i
 <tb> chrysalis <SEP> a <SEP> 12
 <tb> 878 <SEP> Acid <SEP> of oil <SEP> of
 <tb> liver <SEP> of <SEP> shark <SEP> e <SEP> 12
 <tb> 879 <SEP> Acid <SEP> of oil <SEP> of
 <tb> sardine <SEP> " <SEP> A <SEP> a <SEP> 12 <SEP> "
 <tb> 880 <SEP> Acid <SEP> of oil <SEP> of
 <tb> mackerel <SEP> " <SEP> A <SEP> a <SEP> 12 <SEP> "
 <tb>
 

  <Desc / Clms Page number 170>

 
 EMI170.1
 i; 881 1 herring Oil acid of dl (+) A a 12 Seoi- demī 882 Acid of hezi.le of solids J 882 j Acid of oil of aolide:

   saurel A to 12
 EMI170.2
 
 <tb>) <SEP> His ?! <SEP> Acid <SEP> of oil <SEP> of <SEP> @
 <tb> liver <SEP> of <SEP> cod <SEP> " <SEP> A <SEP> a <SEP> 12 <SEP> "
 <tb> 884 <SEP> Acid <SEP> of oil <SEP> of <SEP>) <SEP>; <SEP> @
 <tb> mule <SEP> " <SEP> A <SEP> a <SEP> 12 <SEP> "
 <tb> 885 <SEP> Acid <SEP> of oil <SEP> of
 <tb> menhaden <SEP> " <SEP> A <SEP> a <SEP> 12 <SEP> "
 <tb> @
 <tb> 886 <SEP> Acid <SEP> of oil <SEP> of
 <tb> pleuronecte <SEP> a <SEP> 12 <SEP> "
 <tb> 887 <SEP> Acid <SEP> of oil
 <tb> residual <SEP> " <SEP> A <SEP> a <SEP> 12 <SEP> "
 <tb>
 

  <Desc / Clms Page number 171>

 Example 888
28 g of linoleic acid, 21 g of [alpha] -benzyl-benzylamine and 23.2 g of dicyclohoxylcarbodiimide were individually dissolved in 50 ml of toluene.

     The solutions were mixed together once and the mixed solution was allowed to stand at room temperature for 8 hours. After filtering the solution, the filtrate was washed with acid, alkali and water, then dried, concentrated and purified by chromatography, to obtain 22.5 g of a semi-solid product. desired solid.



  Elementary analysis!
 EMI171.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 83.60 <SEP> 84.01
 <tb>
 <tb> H <SEP> (%) <SEP> 9.87 <SEP> 10.08
 <tb>
 <tb> N <SEP> (%) <SEP> 3.05 <SEP> 3.21
 <tb>
 Examples 889 to 918 are shown in the following table:

  <Desc / Clms Page number 172>

 
 EMI172.1
 III T - ¯¯ "'' '' '' '' '' '... ¯ ... 6" "- .¯w - ¯¯¯ā.



  C% H% N% ¯¯ :: en- Pro) le! Acid, mine 0 = Solvent! -7 D priety "ThêoI" 1na] Ii'Théo- 'Analy-JThéo-'Analy-; : tick: tick tick tick; tick; tick 1789 Linoleic acid d - / "\ # * Ether 16.0, 45" -50; '83.60 83.80 9.8'7:: 10.04 3.05 3.14 d Iinoiëi.qtle (i)' --./ FrthG'r al 'acid. ! 3.0 "ru 3.1 '890! R FF 1 i Dioxane + 16.0, 83.60' 83.71 9.87: 9.99 3.05 3.25 f (-) - (¯) -; Dioxaime ''! 16.0 83.60 83.71 9.87. 9.99 3.05; 3.25 j.

   Oleic acid dl OR3 CI, Tetrahy-Seni- 83 24 83.50 F 10.26 10.42 3.03 3.19 EO3 drofuran solid '-' 3 '/ "drofuran: i solid P92: Isostearic acid i. D1 (): -0! 'Ether *' 82.88 83.01. In, 65 10.79 '3.02 3,.? S93 d (+)' --1 Benzene::. P 82.88 i 83 , 05 10.65, if 10.79! 3.02 3, bzz il j. Tiifft 894 toluene 894 (-). I -. Toluene 82.38; 83.12! 10.65 10.83 3.02 3 , 2> (, 95 .c3.de lino3én.i.que; dl (+) - '#'. Toluene i "83.97 84.12 9. '? 9.71 3.06 3.16 896 t¯ Oil of lia dl (:!;) -0! benzene '"Q97! Safflower oil d {+) - / \ Benzene" j Oil of - Il bzz Toluene t! ! : .r-. ! 'J99 Cartiiane oil dl (+) Toluene It! 1 earthae.

   F dl {+) \ # / 1 strand .. ¯..r ..... ¯¯¯..¯¯¯¯r.¯.¯¯¯¯ ...., ..... ¯¯ ¯ ... ¯ .... ¯¯ .. ¯¯ -¯

  <Desc / Clms Page number 173>

 
 EMI173.1
 5w Oil acid of -0 .Chloroform! Semisoja solid 901 d oil fcid! 901 Sunflower Chlorofome Oil Acid \ # / 9O2 '-± fi Toluene Castor Oil Acid \ # / 903 j Tj Oil Acid - / \ Toluene 93 Oil Rapeseed \ - / Tolûane # Acid 3 - Toluene cotton oil \ #! # 05 Oil acid; 'Olive toluene 1' # 905 Oil acid - Benzene) 'peanut \ # / etr? Ch3.de 907 Oil acid + - () Locust benzene 908 Oil acid ¯ - Tetrachlom- de chrysalis re de car-: chrybalide lbone lu - \ I-yridine oil acid shark liver #

  <Desc / Clms Page number 174>

 
 EMI174.1
 ! 910 1, Oil acid of t-O i: Benzene # solid sandine j. Î j solid! 1 l 911;

   ,. Oil acid of I! ! D Ether mackerel 1 licid of h, zile ',. thor 912 1 D oil acid; Ether! ! .. herring \ #r: i 913 1 d of 1 D oil:; Ether µ. sc.urcl \ # / 's <ta '... 1 1 914! Huila da f j acid! D j; T => 1t! Na! .. j i 1'oie de nOJ. "Ue 1 i" # j s i. f 915 culet de j f! If D s f Toluene i! 915: .. clde nw.ot oil Tol-uene l! 'j 915 Oil acid e fi) Toluene nenhaden \ #' meIJhaden --J 917 J oil acid) To2; ene 917 pleuronecte To: 't: è = tc pleuronecte \ # t 918 Acid d 'oil f 1 Toluene! i / residual 1 Î Ô 16 '"! r .., ¯ ¯ =:

   i

  <Desc / Clms Page number 175>

 Example 919
Standing for 24 hours, a mixture of 10 g of linoleic acid and 11 g of [alpha] -benzyl-benzylamine was heated at 180 ° C. The reaction mixture was purified by chronograph to obtain 14.2 g of a desired product at 45-48 C, Elemental analysis:
 EMI175.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 83.60 <SEP> 83.76
 <tb>
 <tb> H <SEP> (%) <SEP> 9.87 <SEP> @ <SEP> 10.02
 <tb>
 <tb> N <SEP> (%) <SEP> 3.05 <SEP> 3.30
 <tb>
 
Examples 920 to 942 are shown in the following tables.

  <Desc / Clms Page number 176>

 
 EMI176.1
 : - 1 -! erJpê- Duration C% B%%! Exer1-j erature: of Pxo j 1: pIe: 3 acid ration:

   Amine! money from! , j - ¯ ----- 1 - t. ple Acid fraction Amime Agent of the faction! priety Theo- Analy-) Theo-y-! 'reaction-! (hours): Theo- priety -; Théo-: knaly- Théo- 1 ÉÉà) "J f ----- 1 (CC) I (hours rle -1 tiqiie rique; tick 1 riglie tique 1 l '!'" 1 1 J t 1920 'Acicle linoleic 140 36 '1 l 520 linoleic id (+) 1 140 36 45 -> 83.60 83> 72) 9.8? ) 9.98 3.05 1 3. ") 921 'Linoleic acid.; 1 (-) 140 36 / 85.60 83.69 9, 57 9, g8; 3.05 3.22 932 Oleic acid dl 140 83 , 24 83.34; 10.26 10.41 3.03 3.06;

   922 oleic acid () 140) 4083.24 (8µ, µW j 10.26) 10.41 5.06 923! .. isostearic acid: J.UI3 dl (i) 150 40 82.88 83.05 10.65 lfll,? 7 3.02 3.05 92li 1t fi d (-t-) 150! 4O 82.88 85.06 1 10.65 10.71 z 3.13) 925 1 (-)! 180 36 82.88 83, '10.65 1: 82 3> 2 5, 9., 926 Lino1enic acid dl ()) il j 150 40 i 83.97 84.12 9.47 9.63. 3.06 j 2199] jgj 927 Linseed oil dl (t) 150 40 J (/ 928 Cextham oil d (+) 180 40 ::: 0101- 929 Carthane oil (->) 180 929 Carthane oil 1 (-) 180 36 950 Oil of carthaae dal (+) Acid 180 16 fil. J '-boric;

   !. !

  <Desc / Clms Page number 177>

 
 EMI177.1
 
 <tb> 931 <SEP> Acid <SEP> of oil <SEP> of <SEP> 140 <SEP> 40 <SEP> Semisoja <SEP> solid!
 <tb> 932 <SEP> Acid <SEP> of oil <SEP> of <SEP> 150 <SEP> 40 <SEP> "
 <tb> sunflower <SEP> @
 <tb> 933 <SEP> Acid <SEP> of oil <SEP> of <SEP> Acid <SEP> 150 <SEP> 20 <SEP> "
 <tb> castor <SEP> boric
 <tb> 934 <SEP> Acid <SEP> of oil <SEP> of <SEP> 150 <SEP> 40 <SEP> "
 <tb> rapeseed
 <tb> 935 <SEP> -'Empty <SEP> of oil <SEP> of <SEP> 160 <SEP> 40
 <tb> cotton
 <tb> 936 <SEP> Acid <SEP> of oil <SEP> 150 <SEP> 40
 olive <tb>
 <tb> @ <SEP> 937 <SEP>! Acid <SEP> of oil <SEP> 150 <SEP> 40
 <tb> peanut
 <tb> 938 <SEP> Acid <SEP> of oil <SEP> of <SEP> 150 <SEP> 40
 <tb> chrysalis
 <tb>
 
 EMI177.2
 z {Acid cl 9 hui 1-- dc 150 40 939 i l .. huib acid LlO
 EMI177.3
 
 <tb> 94C <SEP> Acid <SEP> of oil <SEP> of <SEP> 150 <SEP> 40 <SEP>

  "
 <tb> 94C <SEP> sardine <SEP> 'oil <SEP> 150 <SEP> L <SEP>: Y
 <tb> 941 <SEP> Acid <SEP> of oil <SEP> of <SEP> 150 <SEP> 40 <SEP> "
 <tb> mackerel
 <tb>
 
 EMI177.4
 941 Oil acid 150 days 40 942 Oil acid 150
 EMI177.5
 
 <tb> ', herring
 <tb>
 
 EMI177.6
 --.------- "'' V. 111 l" "" "",!

  <Desc / Clms Page number 178>

 Example 943
Laying for 50 hours, we heated at 180 C in an atmosphere.
 EMI178.1
 nitrogen ro. a mdlango do 10 g of linoleum do + methylo ot of 11 <2 of 0α-bonzyl-bonzylamino, removing the nitxlanol from the reaction system. The reaction mixture was purified by chromatography, to afford 15.3 g of a desired product; melting point 46-49 C.



  Elementary analysis
 EMI178.2
 
 <tb> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 83.60 <SEP> 83.61
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 9.87 <SEP> 10.09
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.05 <SEP> 3.25
 <tb>
 Example 944
Laying 3 hours, we reacted at 150 C, a mixture of
 EMI178.3
 10 g of ethyl isostearate, 11.2 g of o (-bonzyl-bonzylamino and 1 g of sodium methylate), the methanol is removed during the reaction.

   Then the reaction product was dissolved in ether and the ethereal solution was washed with acid, alkali and water according to the usual methods, then dried and purified by chromatography. , to obtain 15.8 g of a desired semi-solid compound.



  Elénontairo analysis:
 EMI178.4
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 82.88 <SEP> 83.78
 <tb>
 <tb> H <SEP> (%) <SEP> 10.65 <SEP> 10.21
 <tb>
 <tb> N <SEP> (%) <SEP> 3.02 <SEP> 3.16
 <tb>
 Example 945 For about 2 hours, a mixture was heated to 160 ° C.
 EMI178.5
 of 10 g of ethyl o16ate, of 11 g of o (- enyl-benzlamin, of 0.5 g of sodium and of 8 ml of ethyl alcohol, then removing the latter. carried out the same treatments as

  <Desc / Clms Page number 179>

 waters described in Example 857, to obtain 14.0 g of a desired product.



    Elemental analysis;
 EMI179.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 83.24 <SEP> 83.66
 <tb>
 <tb> H <SEP> (%) <SEP> 10.26 <SEP> 9.91
 <tb>
 <tb> N <SEP> (%) <SEP> 3.03 <SEP> 3.21
 <tb>
 Example 946
At 22 hours, a mixture of 10 8 carthamo oil and 11 g of [alpha] -benzyl-bon-zylanino was heated in an autoclave to 200 0. Immediately thereafter, the same treatments were carried out as described in Example 857, to obtain 15.0 g of a desired product 6.



   Examples 94? to 987 are shown in the following tables;

  <Desc / Clms Page number 180>

 
 EMI180.1
 : '' eap- Duration: - deletion Duration: Pzb-; pie. Acid fraction i Amine Agent: de la Ptu- -, -: - - ', "No Acid fraction! Reaction; react; in: prlé10é Theo- aly-! Theo- xa3 = Theo- .naly-' ¯rt ¯¯¯¯s (OC); (hourē): tick tick; freeze tick t tiq11e #, ########## - ------ ... - .. .....: -....

   J .b. "'.1; - vI--' -" .. "'f 947 fj I1é1e I lino1eate dt) t; 1 160 49:! 45 ¯501:: 83.60 s3.72: 9.8? 0 , 3! 3.05 2.94 d 948 d 1 (-): III 160! 48 83.60 83.74 9.87: 10.06 3.051 2.87 949 'Ethyl oleate d (+) 140' 48 Semi- 83.24, 83.34 10.2; t 10.41; 3.03 2.90! Solid 550 sf; methylol isostearate dl (: t) 'NaO C -3; 14o 14 i 3 "82.08 83.10 '10.65 O, F33: 3.02 2, & 3,951 140 82.88! 83.09 10.65 10.82! 3.02 2.91; 951 (+) 140 49! 82.88 83.09 10.65: 10.82 ,, 02 2.91 É 52 1 '! Z 56 i Ft "t; 2: 82, F38 f 83.1. 10.65 10 72 3.02 2.24 i 952 i (-) 160 82.88 8.11 10.65 1.0.72 3.02 2.84- 953JLiDolêato de méthyl du 180 d 83.97) 84.21 9.47 9.63 3.06 2.87 b. ' t ..



  '954! Linseed oil di z 50 fi:! j! 955 Carton oil 180 50 955 Oil - car1; hane d l (+)! 80 Iii j 1 f:.:., 556: - / (-) z 50 1 1 !! t * 957 Methyl ester d (+)! l70: 60 "X".! safflower oil CLecarthane oil i "1 itff Ir;!: fI '¯j¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ -.... ... - - ------ ............ ----------------- ........ . --......................... 1 ... 4 .. --- ¯-PV'l ..... <t. '"

  <Desc / Clms Page number 181>

 
 EMI181.1
 
 <tb> erase <SEP> 3) urea
 <tb>
 
 EMI181.2
 pie Acid fraction Agent of T ... <-n priëté] ple Acid fraction Reaction agenti r-property
 EMI181.3
 
 <tb> reaction <SEP> (hours) '
 <tb>
 
 EMI181.4
 = -. .,. ¯¯¯¯ - ¯¯ ..

   ---)
 EMI181.5
 
 <tb> 958 <SEP> ballast <SEP> methyl <SEP> of acid <SEP> Acid <SEP> 160 <SEP> 50 <SEP> Semi-
 <tb>! <SEP> of oil <SEP> of <SEP> soybean <SEP> boric <SEP> solid
 <tb> ' <SEP> 959-Ester <SEP> methyl <SEP> of acid <SEP> 160 <SEP> 50
 <tb> oil <SEP> of <SEP> castor
 <tb> 960 <SEP> Ester <SEP> methyl <SEP> of acid <SEP> 160 <SEP> 50 <SEP> "
 <tb> oil <SEP> of <SEP> cotton
 <tb>
 
 EMI181.6
 961 i Estcr net acid 160 93;

   
 EMI181.7
 
 <tb> oil Olive <SEP>
 <tb> 962 <SEP>; Ester <SEP> methyl <SEP> of acid <SEP> 140 <SEP> 50
 <tb> - <: -> <SEP> 'of oil Peanut <SEP> <SEP> '
 <tb>
 
 EMI181.8
 963! Esternethyl acid 180 66
 EMI181.9
 
 <tb> oil <SEP> of <SEP> liver <SEP> of <SEP> shark
 <tb>
 
 EMI181.10
 964 160 (65
 EMI181.11
 
 <tb> oil <SEP> of <SEP> sardine
 <tb> 965 <SEP> Ester <SEP> methyl <SEP> of acid <SEP> 180 <SEP> 56 <SEP> "
 <tb>
 
 EMI181.12
 mackerel oil go! Ester = 18qu66 ethyl acid
 EMI181.13
 
 <tb> oil <SEP> of <SEP> herring
 <tb> 967 <SEP> Ester <SEP> methyl <SEP> of acid <SEP> 200 <SEP> 65
 <tb>
 
 EMI181.14
 denorue bzz liver oil)

   
 EMI181.15
 
 <tb> 968 <SEP> Ester <SEP> methyl <SEP> of acid <SEP> 140 <SEP> 80
 <tb>
 
 EMI181.16
 i = pleuranect oil
 EMI181.17
 
 <tb> 969 <SEP> Oil <SEP> of <SEP> soybean <SEP> 140 <SEP> 60 <SEP>; <SEP>
 <tb>
 

  <Desc / Clms Page number 182>

 
 EMI182.1
 ----- f ---....-.......... r .......... 1 .... ..

   V ..... -4- i 1 i .... 1 "" "-;
 EMI182.2
 
 <tb> 970 <SEP> Oil <SEP> of <SEP> sunflower <SEP> 140 <SEP> 60 <SEP> Semisolid <SEP>: <SEP>
 <tb> 971 <SEP> Huila <SEP> of <SEP> castor <SEP> 160 <SEP> j <SEP> 60
 <tb> 972 <SEP> Oil <SEP> of <SEP> rapeseed <SEP> 160 <SEP> 60
 <tb> 973 <SEP> Oil <SEP> of <SEP> cotton <SEP> 180 <SEP> 60 <SEP> "
 <tb> 974 <SEP> Oil Olive <SEP> <SEP> 160 <SEP> 60
 <tb>
 
 EMI182.3
 19.75 IRUJJC arachnid 160 t 975;

   Peanut oil 160 60 ..! j i 976 Locust oil I6ü 60 11 y97 "f i Hu3.13 d.c; ohrylide 160! 60
 EMI182.4
 
 <tb> 978 <SEP> Oil <SEP> of <SEP> liver <SEP> of <SEP> shark <SEP> 160 <SEP> 60
 <tb> @ <SEP> 979 <SEP> Oil <SEP> of <SEP> sardine <SEP> 160 <SEP> 60
 <tb> 980 <SEP> Oil <SEP> of <SEP> mackerel <SEP> 160 <SEP> 60
 <tb> 981 <SEP>! Oil <SEP> of <SEP> herring <SEP> Acid <SEP> 160 <SEP> 60
 <tb> 982 <SEP> Oil <SEP> of <SEP> saurel <SEP> boric <SEP> 140 <SEP> 60 <SEP> "
 <tb> 983 <SEP> Hune <SEP> of <SEP> liver <SEP> of <SEP> cod <SEP> 140 <SEP> 60
 <tb> 984 <SEP>;

  Oil <SEP> of <SEP> mule <SEP> 140 <SEP> 50
 <tb>
 
 EMI182.5
 985 of nonhaden the 50 j
 EMI182.6
 
 <tb> 986 <SEP> Oil <SEP> of <SEP> pleuronect <SEP> 140 <SEP> 40 <SEP> "
 <tb> 987 <SEP> Oil <SEP> residual <SEP> 140 <SEP> 50
 <tb>
 

  <Desc / Clms Page number 183>

   Example 988
 EMI183.1
 To a solution of 22.5 g of </ - bonzyl-bonzylanino ot f3 g of trinethylanino in 100 ml of anhydrous ether, a solution of 30 g of chloride of linolenic acid in 50 ml of anhydro ether was added. The reaction mixture was boiled for 2 hours after the addition.

   Then, the ethereal solution was washed with acid, alkali, and water, then dried, concentrated and purified by chromatography as in Example 857, to obtain 48 g of. a product desires.



  Elemental analysis:
 EMI183.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 83.60 <SEP> 83.79
 <tb>
 <tb> H <SEP> (%) <SEP> 9.87 <SEP> 10.04
 <tb>
 <tb> N <SEP> (%) <SEP> 3.05 <SEP> 3.27
 <tb>
 The examples 989 to 1019 are shown in the following tables:

  <Desc / Clms Page number 184>

 
 EMI184.1
 Example- 1 c% 1 x% j N% ple Acid. Solvent j D priet6f Th6o- 1 4nely- [Theo- 1 ÀnalY-1 Ehé - 1 riquej tique; tick tick risk tick - l, 1 î -jj --i 1 --- 1 1 ---- jf ---- # (---- 1 1 ---; 989 Linoleic acid (Çl) * dl +) - tbyl Ethc3r j 47-50 '83.60 83.88; '9.8'7 9.99 3.05 bzz Î -amino i)' Î '' µ ¯ '990 (Cl) / d Wace Acetone 1- 16.6- 83.60 83.79 9.87 9, 91-3.05 2.88s 91 (Ci).

   (- Pyridine Toluene 1'7.8 83.60 83.71 9.87 10.21 3.05 2279 992 Oleic acid (Cl) dal (+) j "Benzene! Seni-! Fi3.2ü 83.53: 10926 10, 34 3.03 3.00 "! Soli-de- '993 Acid isostea = 3.qgie (CO) (dl (+)! K., CO iHethyl-" 82.88 83.09' su z 3.02 2 , 81 1, j isobutyl- 1,. 981 994 jd (+) j ketone 82, fE3 83.09 10.65: 0.90 3.02 2.79 995 (Cl) / (+) KO $ water 82, 88 to 83.09 10.65; / 10.90 3.02 2.79 995 "(Cl) É (-) KOS Dioxane /" 82.88 63, olo j 10.65 10.87 3.02 2, 99
 EMI184.2
 
 <tb> water
 <tb>
 
 EMI184.3
 P.B, ti 99fus:

   Linoleic acid (Cl dl () DiQethyl-.Et.her 83.97 8-tk, 12 9.47! 9.67 3.06 2.9r, "996 '' ido linlé" (C0'i Ù "aniline Eth 2 j 67 9cj'7 leuile lîn (+)! Toluene ** t * 957 Linseed oil Triethyl- Toluene 998 'Safflower oil (Cl) ld canine Toluéne 1999 "1 l1 = 11 1l 111 1000 (CI)! Da () j a -------------- TO ----- i ---- '-to - 1 --- S ----- L ----- 1- ---------------------- too bzz

  <Desc / Clms Page number 185>

 
 EMI185.1
 .

   i pNôe Acid Agent Solvent Il Property No ------> --------- l ----- 'iil --- i i ** - 1- Pi "
 EMI185.2
 
 <tb> 1001 <SEP> Acid <SEP> of oil <SEP> of <SEP> soybean <SEP> (C1) <SEP> Pyridine <SEP> Toluene <SEP> Semi-solid
 <tb>
 
 EMI185.3
 i ï 1 n S 1 with touring oil (G "l'XzG 3 Meth3rl-isobu-"
 EMI185.4
 
 <tb> tyl-ketone
 <tb>
 
 EMI185.5
 1003 Castor oil acid (01) Diaethylaniline'Toluene I004- Rapeseed oil acid (Cl)! Tri! Aethylanine Ether 1005 Cottonseed oil acid (CIL) 1111-j-ridine "
 EMI185.6
 
 <tb> 1006 <SEP> Acid <SEP> of oil Olive <SEP> <SEP> (C1) <SEP> K2CO3 <SEP>! <SEP> = <SEP> Acetone / water <SEP>
 <tb> 1007 <SEP> Acid <SEP> of oil Peanut <SEP> <SEP> (C1) <SEP> NaOH <SEP> Tetrahydro-
 <tb>
 
 EMI185.7
 ! 100S Locust oil acid (C1);

  KOH -Dioxin / water '1008 locust oil (CI) -. KOH Dioxin / water. 1009 Cary oil acid / 3 iMethyl-isobu-
 EMI185.8
 
 <tb> salid <SEP> (C1) <SEP> 2 <SEP> 3 <SEP> tyl-ketone
 <tb> 1010 <SEP> Acid <SEP> of oil <SEP> of <SEP> liver <SEP> Na2CO3 <SEP> Acetone <SEP>)
 <tb> from <SEP> shark <SEP> (C1) <SEP> 2 <SEP> 3
 <tb> 1011 <SEP> Acid <SEP> of oil <SEP> of <SEP> sardine <SEP> (CI) <SEP> Triethylamine <SEP> Toluene
 <tb> 1012 <SEP> Acid <SEP> of oil <SEP> of <SEP> naque- <SEP>
 <tb>
 
 EMI185.9
 1 13) reau d'hniie hare "(Ci) And" r
 EMI185.10
 
 <tb> 1013 <SEP> Acid <SEP> of oil <SEP> of <SEP> herring <SEP> (C1) <SEP> Ether
 <tb> 1014 <SEP> Acid <SEP> of <SEP> oil <SEP> of <SEP> saurel <SEP> (C1) <SEP> "
 <tb>
 
 EMI185.11
 1015 Acid of liver oil Acid of liver oil
 EMI185.12
 
 <tb> cod <SEP> ¯¯¯ <SEP> (C1)

  
 <tb>
 

  <Desc / Clms Page number 186>

 
 EMI186.1
 ".Trl> .tl¯¯¯¯ --.......-- r-- ... ¯ ....--. ¯ ..



  , 1016 Mullet oil acid (Cl) N a OH Acetone / water Seoi- Mullet oil acid NaOK Acetone / solid water
 EMI186.2
 
 <tb> solid
 <tb>
 
 EMI186.3
 1007 Oil acid neHwden (C0) 1 Tynidine Ether solid 11011 t Oil acid from nenhaden (Cl) 1 Iyridine Ether! 101.5: ide depleuro- 1 day oil! Toluene j 1019 1! residual oil acid (C1); ti: Ether I t = É --------------------------- 1 --------------- o -------------- oÉ

  <Desc / Clms Page number 187>

 Example 1020
Lying 8 hours, using a water separator, a solution of 20 g of linoleic acid was brought to reflux, then brought to reflux.
 EMI187.1
 17 g of o (-m6thy1-p-nitrobenzy1amino ot 0.5 8 of aoido p-tolueno sulfonic acid in 300 ml of toluene.

   The toluene couoho was washed with an acid, alkali, and water, then dried and tested to obtain 22.3 g of a desired product; nD23 1.5111.



  Elementary analysis!
 EMI187.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 72.86 <SEP> 72.67
 <tb>
 <tb> H <SEP> (%) <SEP> 9.41 <SEP> 9.21
 <tb>
 <tb> N <SEP> (%) <SEP> 6.54 <SEP> 6.66
 <tb>
 
The examples 1021 to 1051 are shown in the following tables in which: Auxiliary dehydration agent:
 EMI187.3
 A. p-1oluen03-ùl.t'oill.que acid
B. p-Toluenesulfonic Acid Chloride
0. Sulfuric acid
D. Phenol-sulfonic acid
E. "IRA-400"
F. "Amborlite-15" Solvent: a. Toluene b. Pyridine c. Benzene d. Chloroform e.

   Xylene f. Carbon tetrachloride

  <Desc / Clms Page number 188>

 
 EMI188.1
 : - Duration C: HC '"Ilfof ExeI! L-" Duration e 5 Plô Acid Anine Sol- de la oc: - ¯i- - "---: ---,? Acid: Amine fAgent for reaction * n Theo - = Analy- '-lhéo- Ana1y-j T'neo-F 3, y- .¯¯¯j¯¯¯¯¯¯¯.¯¯¯¯¯¯¯¯L - # ¯¯¯¯¯¯ ¯!! Z¯- (hours)! B ric tic risk! Tic ri c tic 1021; '. Oleic acid 1 CJI..r \ A a 8 231.5123 72.93:, 16. 9.97 Zo, l3 G, 30 i 6.05 No 2 5 i! .. !!! ') {! Ji!. ..,!,, Z2 1022cidelinolenic jf CH-o-N02 B;! 20: 23 1.5100 73.60 '73.90 9.15 9.52! 6,%! 6.12 Ii!. 1; 1 1023' Li --- olenic acid NJ12C E- r .. A aj 10, f. 22,51,515! 73, 26?, 52! 9.56, 9,? 2 16, 214 1023 Liolonic acid ICE- ej 1.5153! 73.25! 956 9.72 6.33 6.14 µ2m5 0 2 CO? Eet.



  1024 Linolenic acid # - D! c 10; 26 1t5109 72.861 72.99 9.41 9.58 '6.54 6.3?: T ;.



  CH l'1 d 2 J! F r, r r E. . .



  *. * <(d)!:! 1025, isostearic NH 2 O 2 C a 14 s 2E3 1 t515S; 72.18 1 72.32 Il f 10.25 fez 0.50 6.48 6.21 <thread, C "3 f. 1: <## ¯¯¯¯. ####### ..

  <Desc / Clms Page number 189>

 
 EMI189.1
 



  1026 1 ÎsCStearic acid 2 '28 1, 72.22Lo. 25 10 e ej 1026 isosteanic acid / / NHll0z '/ / 1 3152 1? 2.18 III 6.48 6.11 If 1021 1 Oil acid XHjCHQ b 12! ! 25 1.5138 l to the M3 card l028! Acid! oil f - NCHV-NO 12! 20 1 L 1028! .1! .. cider 'oil CH-o- N02 95131, III j-soybean <- {5 \ == / 201.5131 J i 1029! Acid! of ICB oil -! : e! 1029 Il9 1.5114j ille oil acid! , f sesame / 2 / Ùé. 12, 191.5114 '* * .....



  1.30 .. b-leide t. 1 C 122 1.51 castor t z)> *? 1 l. * Q: ..... 1 1031 Oil acid from C3R7 J. 1 12 20 1 95133j,) t j <7! i If,. ## i.¯¯¯¯¯¯¯¯¯¯¯¯¯¯j¯¯¯¯¯¯¯¯¯¯J¯ i ¯j¯¯¯¯¯¯¯¯!

  <Desc / Clms Page number 190>

 
 EMI190.1
 
 <tb> Duration
 <tb>
 
 EMI190.2
 exeat 1 Duration pie Acid; # i-mtréaMn <"D 0 ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯; ¯¯¯¯¯¯¯¯¯¯¯¯¯J¯¯¯J¯¯¯;

   (hours); j¯¯¯¯¯j! J "" "'!!! (hours)! 1032 Cottonseed oil acid; t lTff2CH- (A at 12 23 1.5129 j' -g" "N02 bzz) -, 3i02 1033 Olive oil acid 1 ± 1L.H 3T, ïj2 a 8 25 i5139; 1034 Linseed oil acid SHF "(] 1OY4- Linseed oil acid 'Ô" 2 é 128.5 115119 M3 IÎ02 1035t Colzg oil acid pS- A) bzz z 14, 1.5159 1035 Colza oil acid 'N0 14.51Z 1.513'9 EO3 N02 t a. "2 1036 Rice bran oil acid --02 11 # a z.0 18 I, 7I23 C "3

  <Desc / Clms Page number 191>

 
 EMI191.1
 ----------------- M ----------------- T -------------- ---------------------------------------------: t.031 J . miJ.e cbrys3J.ide CHo-1I02 JO (1 J., 5100 lD37 i. cbtysalide 1 1 1 ï D 10 r ¯: s. 23: 1.53;

   Oil acid depleuronecte fIHOEfi-aO 1,: l '5123 1038 Oil acid pleuronecte CR 1 "" "\ .- N02 1.5123 2-5 1039' Dôhniie liver reauin 1 'ZHOEd ± 2Î5 / oj, 514 @ 1039 'liver oil acid recmin h " <0 "') i! I e; 12 i 22 1.5144;! 1..cide of oily. Liver REQUIN -' [g 3 1. ; : ï.2 1 J t. ! '. i i! i 1 104O Oil balaine JMCH- ± -K5 l 2µ j 1> 513% 1040 Oil acid unwrapped NCH-Q-NO 3 d. AT ! J! d; ! ! 23; 1.5134 j III 1041 Acid from cuttlefish oil,?; lYQ B b 20! 24.51 J., 5J. 21 j '.

     - UM '"" N0)' 3 CH! fi; ! 1042 Sardine oil acid (XHOE 9 e 12 # 23 1.5221 CH 0 2 - - f "1 l !! l '- È

  <Desc / Clms Page number 192>

 
 EMI192.1
 1 t t ;:.! 1043 NBCH Mackerel Oil Acid - NO 1. i il ''! 1.514? 1043 Mackerel Oil Acid .w-40: 'B b; 20: 225! 1,51407 * ix 3!: 1 j: i! 1 1044 Oil acid scombrêsoce d j, 14 26.5! ! ; 1.5237 1044 with scombrésoce oil CH .... 9 \ l4! 26.5] 1,523? III 1 !! ' !.



  3. ! t t - ', Tr,; é 1045 4ciae 'l: uile herring lffi'Jt.'R- {'. .. ') .1.t \ ..'- ". Ii il. 10 1.5114 1045 Acid of herring herring NE at 30 1.5114 \ - CR3 t' t ', t if 1 1046 Acid of herring Saurel oil HEp # - '! j 30 s 1.5133 1 1046 1 .Acid ci' oil will know IffL # - (-}! J 1.5138 j -I C1I3 t..rn '; w-J2 batch .cïc' ! e oil nenhaden I!; Il! 1,5iet-9 1047 BELCH-NO- D nonhaden oil acid a 1 z 1.5149 èB:} "no 2; zo 1048, Liver oil acid Etorue NH # - 'y 30.5 1.5139 1 1048;! Cod liver oil NH2CH- j E ¯ r 12 f' 30, 1., 1 "" CH j¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯LL # - # ¯)! ! LL ....

  <Desc / Clms Page number 193>

 
 EMI193.1
 



  ..... ¯., ¯¯¯ ... ¯¯¯¯¯ .... ¯¯¯ ... ¯, ...... ¯. ¯¯¯ ##### 1049 Acid from liver oil N H2CE 'e 12: 24.5 ¯ 1.5230 m 2 1050 Acid from nen-e oil NH? CH f 1 NA a 12 2 1.9140 CH iosl j A = ide dliiiiile aiaie XlHzcù. # '6Us ñon t 1.5133 1051 -Acid residual dliiiiil Gg- 120.31 1051 Acid d.1. resign ,, g5 A j! 20.3 1.¯¯.¯-¯¯¯¯-¯ ....,. W..¯.¯ ................ ¯ ..... .¯ ... .¯¯¯¯ .... ¯¯¯¯¯..¯ ..., ....., -., W. j

  <Desc / Clms Page number 194>

 Example 1052
 EMI194.1
 20 g of 1ino16 acid were dissolved individually:

  1.quo, the g of o (-mothyl-o-nitrobonzylaaino and 20 g of dicyclohoxyl-carbodiimide in 100 ml of toluene. The solutions were mixed together at once and the mixed solution was allowed to disperse. at room temperature for 8 hours After filtering the solution, the filtrate was washed with acid, alkali and water, then dried, concentrated and distilled, to give 11. 1 g of a desired product; nD23 1.5140. Elemental analysis:

   
 EMI194.2
 Th6or1 <read Ans.l: '(t1 qu
 EMI194.3
 
 <tb> C <SEP> (%) <SEP> 72.86 <SEP> 72.68
 <tb>
 <tb> H <SEP> (%) <SEP> 9.41 <SEP> 9.03
 <tb>
 <tb> N <SEP> (%) <SEP> 6.54 <SEP> 7.01
 <tb>
 Examples 1053 to 1073 are: listed in the following table:

  <Desc / Clms Page number 195>

 
 EMI195.1
 -. ## ## <## - ###### -. ### ### - # # - t'IL en-! ; i Agent! 1 oc i 7f1! JO! Np, .e Oat Acid. - # = J.'t-! Solvent; Theo- Analy- Theo- Analy-;

   Theo- Analy-! Acid 'i BN * C * 1 B S l' Theo-. ànaiy-Î Théo- ànaly-] Théo- Analy-t B D rique '. tick; tick tick tick --- --- #### ---------- --------! --------- 1 ¯..¯¯.¯. ¯ ... ¯.¯¯¯ i .---. ¯¯ ¯ ... ¯¯¯..p ¯¯ .... ¯ ¯..¯ ¯ ¯: l¯,: e-! 1) 55 Oleic acid; i 'y ,,' 77 Cg 1 J 0; i i Ether 1 i 25 1.512 / i 72.93: t 73.22 9.97 µ Ô 10.12! 16.30; 6.05 G C5 N02! (1 l ') 54 Linolenic acid! , 1; ! ; 73, GO 73.66 j 9.15 9.43 6.36-6.12 imH imoenic acid! \ -y 1 Tniué; e 1.51061 He! . ! 1. 9.43) 6.36 6.12 C-5 i i! 1 it; ! I! 1 t55 Linoleic acid i NH2ßH, V¯! 1 -0 'Benzene! 2? 1.5155 / 73.26; 73.61 I !! 9.56; 9.72; 6.33; 6,2F3 C¯H 0 ..., i 1 1! ". ..-. 1: 1 ....



  ##, [lj "156 j Linoleic acid ICH -0 Benzene j 28 1: 510ô 7é.86) 73.05 9:41 j 9.6ô Ó, 54 6 '? 3: i: bzz3 bzz) ....



  '- **! 1.



  (dj Iii ..



  57 NH2CH-Q-N02 isostearic acid! . . ± J Cycle-! 29 1, sls31 72.18? 2.3? ) 1.51p, 4F3 6.48; 6.39 <-) \ == / 2 j \ -y hexane It! / TT 3 i i i i i ¯L # -.- '. ###. # .-. ## -.-- L ## L # .- ¯L

  <Desc / Clms Page number 196>

 
 EMI196.1
 1038 Acid '! CE- CH- - l, 5153j t <72.18! 72.38 10.25! 10.47 i 6.36 "'(1) µ / 72 * 18 1 * 25 00.47 6.36! 1058! 1sostearic acid f f02;' 3 CH- J f Benzene! 1.5153j j, f '12 .18 72.38: If "1.0., 25 1 10., 47 6.48 JI r 6.36 1 'hÀil 1 J,.! J 1 1059: Oil acid NCH #.

   Chloro- 1.5137! ! safflower fmr '= m: foine caxti! ae. : i ¯ - IJJS 0 = fozne l '!' 3 2 ', 1 1060 Oil acid NH # - NO.,! 3 \ # -, Tétraehlo- 1,513l! '10 -E,. ^ T of oil' Î ± Ôlµ> ÙkIÉk / j z1- 1.5131 = soybean C-H 1 = C3.,: Rure de, j 'CBÀÎbÔfi3 z-.5 caruvne t. 1 1061 NHCH- oil acid! - / \ i f Benzene! ! t 22 1.5U5! ! 1061 CB j Benzene l, 5ll5Îsesaae "ÎQj" z-) sesane CH 1 O 2 kcide:; .... 1 3 i fi, OOOO 2 ÀiÉÎI '1Ô2 ..1 IOo2; r l.cide hui.le if ..



  1062! Oil acid CH - NO! - / \ Ether 1,5122 ': *' = i'icili 2 - \ ¯ / castor C '\ .... / fi iii .... ii to i ". / 1063 Acid i {: oil of CS - NO 1 ü ± ¯ Benzene - 1 1 ...



  1063: NH2CH oil acid - p 2 ¯ / \ Benzene 1 20 1.51321! 03H'l j! f

  <Desc / Clms Page number 197>

 
 EMI197.1
 '1064: oil acid; ; NH2CH .. Benzene '24 1.5127 cotton)] 3 1 m l065 jfidq of lIHjOE oil $ wo fi Benzene, 22 j 1.5142 1065Acided'huilo f IH2CH - N02 - "Benzene 22 1.5142! Of olive YY olive OE3 ÉH j 1066 .cida 4 ':. Nilo de / [I3HCHQ / j' Toluene! Toluene 24 1.5122 lin 1 p '2 i;.' ¯ '' t
 EMI197.2
 
 <tb>
 <tb>
 
 EMI197.3
 1067! NH2 oil acid CI, -F% - .Pyridie 22 1.5124- '/ plenronecto' 1 - = 2 \ -y 1068 CH oil acid - 10 J jj Dioxanoe 25 1.5133 1069 d-acid 'hvil 3 ÎTetrahydno-, 1.513O = t 1069 Oil acid from' OE2 - / \ j furan 25 195130 cuttlefish furan ri '1]

  <Desc / Clms Page number 198>

 
 EMI198.1
 1070 oil cide.

   NH2C Pyridi3ae 1.5145 1070 i.: oil cid NSCB - /) Iridine 1.5145J! sardine OE3 02) [! .> .. +.



  1071; Oil acid NH # -. - / \ Benzene 1,141J 1071 Oil acid; NFi2CI3 Benzene 24 1.5I41 sanrel OE3 "'j leu72 Acid ia .'- u.3.lr de 17ï: 3-1, 1 t JS-ulier; 22 1.5214! Liver (' i ,, 02" - " i liver 3 i Tolerates 1.5036 residual 1G2 j [1 (1.51361 ----------.---------- S ----- L ----- -¯ = ¯-¯¯¯1¯¯ --- ¯¯à - ¯¯ --- ¯¯¯¯-¯¯i

  <Desc / Clms Page number 199>

   Example 10'74
For 24 hours, we heated to 180 0, a mixture of
 EMI199.1
 10 g of 11nolé1q # acid and 9 g of 0 (-ndtirl-r-ni.trobeazyiavm3no, removing water during the reaction.

   The reaction product was dissolved in ethor, and the ethereal solution washed with acid, alkali, and water, then dried and concentrated, to afford 11.1. g of a desired product; nD28 1.5138 Elemental analysis:
 EMI199.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> 0 <SEP> (%) <SEP> 72.06 <SEP> 72.63
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 9.41 <SEP> 9.24
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 6.54 <SEP> 6.86 <SEP>, <SEP>
 <tb>
 Examples 1075 to 1105 are shown in the following table:

   

  <Desc / Clms Page number 200>

 
 EMI200.1
 Ex.! Temp- Duration C% Il% EX. rature Acid! 1. of the N! At11ne acid ..I.o.gen1 ;. of the . summer! VS ! ¯m. --1 ------- r ..., '1 reacti- (hours)! D Theo- i Inaly-1 Theo- Analy-I Theo- Analy-1 ... -.-... w. ! :,; Cr ric; , tick rique, tick rique = tick 1075.JLcide <j oleic ': rr2 / \ ¯¯ /, {! iso 2. lit 1 22 i, 5z22 72.93 t! 73.20! 3 = 9.9? j j 10.17 '"6.30, .2 C¯H 2 j. i i i: i!!.



  'i !.



  1076J Acid UduLeNE3 (j) H! 180 1,5004! 73.60 73.G1 9.15! ) 9.32! 6.36! ! 6.16! 10761 amino acid; N1LCH-; 'Mar 02 180 24 24 1, 500! -: 73., 60 73.Cl! 9.15: 9.32 s, 36; 6.1s I - I!;! : '. i 1 1 C2, '5 Z-5 NO! ! j! ii 1077 * Linoleic acid; 2 f; H 2 t 180; 24 d 2 5 1.5155! ' 73.26? 3.55, 5 j 9,? 0 6.33 j- 25 i ¯ .ws .. t ...



  ! 07B Linoleic acid f 160 12 j 72, C6! 73.06) 9.41, 68; 6.54 6, "H ..jt * i-178! Linoleic acid NH2CH \ (cide 1 ï2 2.5II1.!;? 2,;: t? 3.06 9.4? 'C, 68 6 , 54 6,.: 5.'i CH 1 02, boric: .. .i: e- X 2 to 5% fI. Ii 1 li .... t fi. F .., *) 79! ' Isosteal Acid - NH2IR-. 160 z, 72.18 1 1Sostea Acid! NR2CH-Q-NO2 260! 23.5 1.5158! 72.18 '72, 40 10.25 10 33 6..48! 6, 40 Sqe f quo Gg3 260 23.5 1.5158. 72.40 10.25 110.33 f!. 6.40!. & ..: f

  <Desc / Clms Page number 201>

 
 EMI201.1
 1080 Isostea-1 CH-o-NO2 acid; 145 39 24.51.5156 72.18 72.39! 1 10 25 10.46 6.48 6941 rique .S S'éa- Il !, 145)> 55 iS ..- 6) x; 9) 1, 46 '6.48 654> 108l! Oil acid from:

   NH2CR-f), 160 36 24 1.5137 -carthame '== <. safflower 1 or 2 yew! I! 1082! Oil acid jmsq / 180 1.512 1082,. Oil acid Nff2oe-o-lîo 180 26 26 1.5124.'1 soybean 'Î 2 2 180 28 26' ') 2 "5 1085 Oil acid -î # # - 180 24 d 1.51041. N ..: 1 sesane # -, NOo 3 V02! *. '"1 32! fi.



  1084I NH2CH Oil Oil 170 2595 li. 5119 Castor 1 --- f - 2 OE3 Castor Cob: 3 1 LOG5 Oil acid from j hHCH- NO 165 23.51.5114 III Mali; of oil! '- {y = 165 123.5 J., SU4I,

  <Desc / Clms Page number 202>

 
 EMI202.1
 ......... -¯.w -...,. & 1 "1i1 r! I 1086 acicle of NH2CH oil 160 i 34 j 1 24.5 1,512B CH3 f) j) ji 1! ' CB 1087 j ± âÇaÎive ht.i2e Nfl2CH-n NO 160 36? 3., 5 1 5129 Î / d o10ve x 1OG8 '1 lc0de of oil f XHCEq) "' /" 1 160 22.5 0.5120; I008 oil acid of t iH2- i60 22.5 1.5120! lin of oil C "3 1 -DNO 160 122.5 111512O! ! lin CH3 1 NO 1, 1 1089 Oil Lcidc i M ± EC Acid! 160 10! 1.5MO - 1.089:

   Lalde d 'lm2CH..ú "\ Acid 160 10 2 1.5140 rapeseed N0 boric l!' 1 calze j '3 N02 bor3.que to 5 If -' S1 'l09ô 1 oil from, -0- ., T {. 1 j 23 i 1090 ± Lcid of oil N02 160]., 5122; rice bran CE 3 - = j 160 1.5122 its rice z0 1 (1 '/ 1; 1 1' jjj ': lOg2 2.c0de of hu10c àe j CH-o-N02 160 32 23 1.5110 J CH3 wire! -----.-------------------- ---------------------------- ..4

  <Desc / Clms Page number 203>

 
 EMI203.1
 ¯ ¯¯¯ ..,. ¯.¯, .... ¯¯.¯ ... ¯ ...... ¯¯¯..f ..- ¯.i # t) "'!' 1092 Oil acid N02 1092 Oil acid of 160 32 21 1.5122 2 1 pleuronect 5 HHzHNOz '160, 0022 1093 Oil acid' c-? 2 160 1.5140 F 1033 Oil kide of 'NH2CH d2 160 1 32 22 1.5140 shark liver / CH t 3 Ji 1! Lit! 160 1.5131 1094 whale fi 't CH-Q- <v 2 160 1.5131) -) whale. 3 f * TT '# t! i -. 1095! NB oil acid # -).

   ! 160 j23.5 1.5130 1095 1) NH2-C oil acid) 160 32 ± 23.5 1.5130 '"# -, 2 1096 1 CH oil acid {i! 1 160 32 i 1 21.5 1.5222 sardine 3 0 1 t 1.5222! 1097 Oil acid of Gg -N / 0 2 145 37 Î j o8, o 1.5152 naquerel 'j 3 ¯¯¯¯¯' ¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯

  <Desc / Clms Page number 204>

 
 EMI204.1
 j "" "" 'j ""' '' "'"' "7! i 1104 Oil acid of Il Î" i - 2 160 31 19 1.5133 1 menuse menuse 1m3 Il! 1105 Oil acid #NO Acid 160 10 18.5 1.0042 residual boric 'boric' 1.5142 residual boric:

   M13 to io) / j¯¯¯¯¯L¯¯¯¯¯L.l¯.¯¯¯ '+' '

  <Desc / Clms Page number 205>

 Example 1106
For 30 hours, a mixture of 10 g of methyl linoleate and methyl linoleate was heated at 180 ° C. in an azoto atmosphere.
 EMI205.1
 10 g of O (-m6thyl-p-nitrobonzyleminal by removing the methanol.) The same treatments as those described in Example 857 were given to obtain 12.8 g of a desired product; nD28 1.5106.



  Elemental analysis:
 EMI205.2
 
 <tb> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 72.86 <SEP> 73.06
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 9.41 <SEP> 9.62
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 6.54 <SEP> 6.30
 <tb>
 Example 1107
For 3 hours, a mixture of 10 g of methyl isostarate, 10 g of [alpha] -methyl-p-nitro-benzylamine and 1 g of sodium methoxide was heated at 150 ° C., removing methanol. The reaction product was washed with acid, alkali and water, following the usual methods, and then dried, to obtain 12.3 g of a desired product;

   nD28 1.5063, Élémontairo analysis:
 EMI205.3
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> 0 <SEP> (%) <SEP>? 2.18 <SEP> 72.24
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 10.25 <SEP> 10.28
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 6.48 <SEP> 6.52
 <tb>
   Example 1108
To a mixture of 10 g of ethyl oleate and 9 of [alpha] -methyl-p-nitrobonzylamine was added a solution of 0.5 g of sodium in 8 ml of ethyl alcohol. The mixture was heated to 160 ° C. for about 2 hours while removing ethyl alcohol.



  Then, the same treatments were carried out as those described in Example 857, to obtain 12.8 g of a desired product; nD22 1,515 @,

  <Desc / Clms Page number 206>

 Elemental analysis)
 EMI206.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 72.52 <SEP> 72.77
 <tb>
 <tb> h <SEP> (%) <SEP> 9.83 <SEP> 9.99
 <tb>
 <tb> N <SEP> (%) <SEP> 6.51 <SEP> 6.30
 <tb>
   Example 1109
For 12 hours, it was heated at 200 ° C. in an autoclavo. a mixture of 10 g of safflower oil and 10 g of [alpha] -methyl-p-nitrobenzylamine and 13.0 g of a desired product was obtained; nD28 1.5140.



   Examples 1110 to 1164 are taken from the following table:

  <Desc / Clms Page number 207>

 
 EMI207.1
 : r '! Duration R RCOA (A) '.: Erasure of the oc'! r id J..m1ne "':' D'en't 1 of 19 .. é ti 121) Tea 0- Analy-! Tlléo- 1 Anal.y -! Théo- Anal7-1 ', -o.!: reaction! r ac. on 'n! D.

   Theo- "knaly- l Theo-; Analy- ÎÉê i, Ana1y-t (OC) (hours) ric tic ric tic i ric tic --- 1 -) j - (µ ------- 1) - 'f] Î --------- i / ------- i Î --- 1) - j ## j ## j ## t; 11101 Oleic acid f' f1LCH- '" flr40i 180 4 22 1.5122; 72.93! i 73.21 i; 9.97 10.05 6.30 j 1 f 6.11: '5 C- R ...' = (N02 - '"4: 1! 180! 1111' Acid" linole- .NSCH - NO.! 5 j .160: j. 37 1.5000 73.60 73.88 j 9.15 9,416.36! 1111; Linol acid- NH2CH N 02 160 22 1.5000 73.60 i! 73.88 9.15 9'ikl 6.36 i 6.24 j inique, 1 C¯H f ,: t 1 .. 1 (COE3) He !! 'Z-5 1') ')' He! N02 It! ! ! ! 1112J 'j Acid -. linoleic NHCH t 2 # 160 37 23,51,5157 73 * 26 'l}, 61! -. 9.55, 9.76 6.33 6.19 j i <o <3 bil5 {¯ 1113 'Linoleic acidNSCH- Acid 16O 12! 22 1.5114 '72, 86 73.04 9.41 19 6.54 6.4?.:' (OCR3) No2 boriqw (OCIL) 5% : -1.



  1 - 5 j))))) 1: '1114! Isosteal acid - NS - NO 160 .24 1.5149) 72.18 72.33 10.50! 6.4th! . 6.43: 11141 ..? Ide isostéa- i r 1402 160 40,: 24 1.5149? 2.18 72.33 10.25! 10t50 6248 6.43 creek "" "- 1!, (OCH :;) 1 1 CH :; i! - j 1 fi! I - '! 1 il!.! 1: ..! T 1 1 ft 1 i .

  <Desc / Clms Page number 208>

 
 EMI208.1
 nw. '1 STEAFA. : 1 'i' "'' (,.".) L 'j 1115Lcideis.stéa- tlCE - BO .. 160! '24 1.5156; 72.18 72.41. 10.25 j 10.54 6.48 6.41 l115! .R..cide: lSOs1; éa- <2, A = / 2 160:: 2fI. 175 156 172.18: j 6.41 i (o) t CfI3 He !! 01161! t (O #.) oil t 16 il 4 '24 IIi j 1 1 JI!' 111l6Í.l..oil acid NB2CI1..ff "\ 160 40 24 1.5135 1 safflower 1,. 3 no Il! J,: (O # I) f!! 1117 oil acid! NïL) CH - -N0 '180, 24 1.5132 soybean ii * h / lÔ-' z 1 j ')' '(oCH) 3 "25 if: l1l8i..cide J 1 1 1 (OCR}) oil ti ; NtLCR: t Î iI5 Î;

   / 1'70! ? 5 t24 l, 50961 Ii ...: 1; 'sesame j 1 ....



  (ocgb) 32 tif ..; J, 1 ....



  1 III! ï '' i i 1 'J1119 oil acid NH #' - NO 180 J24 1.5. ' castor oil! = '! ... i i 3 3 It! - j j j ..



  *! ll2oLcide of oil I # - NO., 180 35 25.5 1,5116 1120 billion of zich N02 oil 180 125.5 l, 5ll61 i held 3 "1 1 z (O) C3! ti fil ¯¯ ¯¯; ¯¯¯¯¯¯¯¯t¯¯¯¯¯¯¯¯J¯¯)

  <Desc / Clms Page number 209>

 
 EMI209.1
 j; 1! '1121 oil acid! ! NECS- - \ 180! 26: 1.5126, cotton l1J 'fi. cotton COCIL law) CF! 3. <jm; -J) Iii! . fi l122 Oil acid ± NH2G "H N02 1 180! 35 t f 26 1.5122)) = olive 1! ' (OCH3) CH3 /) l125 # ± de 3 of hujiu NH # I- / '3 16O j 24) 1,5120! C; ¯ldQ huf .ex IQ, -1 (lin NQ for. N CH- ¯ z -5 bzz i 1124 oil cide NfiC3 160 24 1.5134i 1124 rapeseed oil (# -f \ 1 160 1) .2 i 24 i '51341' co1za Cg5 fit <.m <tt 't! 1125 'Oil acid NECS- / r y-NO 160 1-5120! i 1125! useful Nl12CH-Q-NO2 160 124 1.15 120; its rice (pcg ..) (OCR}) 1125 Oil acid / 3 160 24.5 1.5116. hi. acid 1125! ido hui1e! C110-NO2 160 24.5 1,511.6;

   Chrysalis IIi (OCR) CR3; .3 <3! !

  <Desc / Clms Page number 210>

 
 EMI210.1
 r ¯¯ ¯ w¯ ¯ ¯ ..¯,; i! . 112'1 Oil acid of 1! . CHOli02 '! 160 44 22 1.5123! pleuronecte III! oCg3) 5 11 2 1128 Oil acid NH2CH- 1102 Il! ! t 23 bzz shark liver 1'010 shark (OOE3) M3 1129 Oil acid from 1 # 2: HCH --- N02 160 3? 23 whale bzz 1 / IT i! (OOE3) 3 3130 'Oil acid from NH2CE- 160 37 23 1.5129) seicho rTT 0 i3) 3 B02! 1131 NH2CH oil acid fi 160 damn? ! 23 1.52201 sardine 1 '== 0 t o 3) 3 (O) CI! fil: 1132 Oil acid of 1 HE2C1! O-W 2 160 '0 23.5 1.51441 mackerel -T - (OCH3) - Cg3

  <Desc / Clms Page number 211>

 
 EMI211.1
 ";. l135 Oil acid of (j m% CH ± t 160 40 zij 3.51 '0 Cg3 02 1134;

   , oil ciaine of NIi2CH- âi02 1 z z 223 1.5120 herring (OCR,) 3 1 1135 Oil acid of 10E2F-G Acid! 160, 12 J23 1,5là6 saurel boriq iie (OCE..3 3 02) d> 1136 Oil acid of NH2CH-- N02 1G0 z J23 1.51157 menhaden + * -21 / F -) bzz?) (OC31 3 3 l137) lcid'hnileàe "02 j22, o 1137 Oil acid of = NH2CH.

   N02 z 4ruz 22.5 li, 5141! liver of name t. "(OOE3) 15 ± 113F3 Oil acid of NH2CH. 160 40 23 1.5218- liver LL" "2 1: l'S (OCH3) CH3 (OCH3" 3

  <Desc / Clms Page number 212>

 
 EMI212.1
 ! ! ! '' ' < <** "bzz.¯¯ 1139! Oil acid of 1 I hHµlI & fW0z 160 z i24 1,5129 j uenuse 1) OE3c> ''" H'3 / # \ j 1140 j Oil acid N% CXNO 160 40 1 25 1.5133i residual 1. ! 5 1.5133 3 5 1141 Soybean oil NH2CH I A02 160 z i> 1 Soybean oil BEC'JNQg 5 160 '42 j j 23 1.5129' i 025! ± Oil in semester EO2 160 4Q j 23 1.5ZOg 1143 Castor oil; j Î M% OE ± $ N0g Cfj. 2 Acid 170 40; 24 1.5122 boric at / / / µ l144 Nais oil;

   NH2CH H02 bzz ') z' south 23 1, 5 1201

  <Desc / Clms Page number 213>

 
 EMI213.1
 --- "'J. 1> 6.Â..t; li 1145 d ...,' .. \ - f 1145 = 'Cottonseed oil N N02; ix7 40 j 24 1,5I2g Il! 1 / ï; 1146 Olive oil NFi2CH / \ 02 160; ap 3 1.5124 opening ti xiii C "3:! 16o j 1 1,512w / 1147 1 Eight ... lia /: r.H2CH -Q! 1 160 j 40 j '2? 1.5123, '/'! 1 j C'ri3 - t '11' ;-D Oil of (, \) Ia NH2'C.H N42 () 200; : 24 1.5122 / fI! 0:! 1149 IIU4-le of his -N0, J23 1133 j 1149 1 Oil his CH. 7 - N02 160 36 i 23 1, 5133 d do rice l <1l9 "2 If j 1 1 f 1150 1 i Oil of chry-!! F # -o-1f02 j 16 to 36 i! J 23 1.5120:..:

   J i salide,., ÉH 3 f. : -------------------------- ¯.- () In an autoclave

  <Desc / Clms Page number 214>

 
 EMI214.1
 1151! Crying oil - Ng2CH - H02 160; 40,123 l, S122; nect 1..52 3 Oil - f i I3OH No 2) 1 "! 16O 122 j 1.5139 shark <3 1153 Whale oil: Lfi2C-02 170 40 1 1, .5126! Eaile s; iche IUOE-4 '() 20G, 5133 1154 Fish oil I'H2Gfi- 4) 7 20 "; 3 1 23 =, 5' 33i TT, uo 2! Fi 1155 Sardine oil NH2i'h 170 40 23 "'¯N02 t 1156 Oil ma! mÕE ± -10 170 Î 2W 1.5139 1156; Oil mask- IZH2CH I402 1-70 îl39 reau ¯¯¯ (CI) In an autoclave

  <Desc / Clms Page number 215>

 
 EMI215.1
 1157 BuiledescoB.br- NBL, C3- 170! '24 i 5146 1157 Uune scombr6- 'OE2C, "-Q 17 3 1 soce i i 1' i157 11tir" "" "'1H5 izo.



  115S Herring oil NHpCB- .rV2 10 i '2! 15120 1158 Iluil herring IM2oe 52: 1 e balC C $., 1 ifie fi 's5! 1159 Sp-urel oil 2) È02 11.5145i i; gvi.e - "21S / z>, z ll'Ic Hz;?. a dc rr: do, n Na 170 ¯ 3? 25 1,5iri il ± C / j ÎiÔz 16o Î! i; 1161 Liver oil ; 1 # LCS '' 16 ° 40; 23 15 140 n6.1 tii CH, 33 = yl;

   ., zl! 1162! Liver oil = 0 160! 1 B fl '"' 2 i j j

  <Desc / Clms Page number 216>

 
 EMI216.1
 i! ..... 4.-4 "" '- .--------- -------. B .. b- ... - -v- 1 i! 1163 DemiSe Oil Ili! I:! Ca-Q- J i t 11 2 170 3 5 125 i .. 1.5127) 1 CH, Ii! j l 1164 Residual oil NH j G'H - Na 2 1. Í 1 170 35 24 151301 - \ = i i i J '

  <Desc / Clms Page number 217>

 Example 1163
While stirred at 0-5 C, to a mixture of 150 g of [alpha] -methyl-p-nitrobenzylamine, 100 ml of anhydrous ether and 8 g of trimethylamino, a solution of 30 g of linoleic acid chloride in 50 ml of anhydrous ether. The reaction mixture was boiled for 2 hours after the addition.

   Then, the ethereal solution of the reaction product was washed with an acid, alkali and water, to obtain 38.2 g of a product.
 EMI217.1
 dduired; P.E. 209-, aC / o, o5 mm Hg! n26 1.5120.



  Elemental analysis:
 EMI217.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 72.86 <SEP> 73.06
 <tb>
 <tb> H <SEP> (%) <SEP> 9.41 <SEP> 9.66
 <tb>
 <tb> N <SEP> (%) <SEP> 6.54 <SEP> 6.28
 <tb>
 Examples 1166 to 1196 are shown in the following table:

  <Desc / Clms Page number 218>

 
 EMI218.1
 : il: 0 eL H t: L: ROOA.

   (X)! 11¯ "- Solvent agent OC" Theol "" nalyl! hiolTa! '0!': Analy- Ne Acid ataine van 2'D; Theo-. -, 'rrn..é. ,, - DD F rique tick; u 0- tick; .r..u. 0- "tick! 166 Oleic acid (CI): rm2CII; carbonate water / z 23 1.5120!? 2.93.! '73.20 bzz ± 10.01. I 6.30 6, Ic3 ÇA! 2 3 jf acetone .167 Linoleic acid! N3CHy-NO.,! H - C2 J jyridine 1. 1 Tetra- t! 23 1.5005 73.6073.79- 73.79 9.15 9.40 6.36 6 , 23 (Cl)! Hydre- (Clji C2H5 1 furan f! 168 Linoleic acid NHCH- <Water Carbonate / '21.5 1.5155! wire 9.72 6.35! 6.19 168 ,; f k.cf. of linoleic lu CR-, Carbonate = Water / Pl 5 1.5155; f: 73.26 ¯ Î3.56 9.56 9.72: 6..33! 6.19 (01) 12% sodium 'tetralit; Ce5q 2 -hydro Iii i "".: Furan T ......,: r..i 169! Linoleic acid, CH ... r \! Hydroxide! Water / 2I 1.51161 72.86 72.94 9.41: 9.6 6bzz 6: il.



  (Ci) ,, C "3 Ni 2 of sodiua; dioxa = O fil:.:" Fi! - '"1 IToLcideisostea-JEE6-NO Tyridine 1!. 1.5152 72.18! 72.32 10.25 10.51 6.46 lO. 1ide isostea-1 CH-o-NO 2 1 Pyridine Ether t 20 1.51521 72918 72932 1a, 25 1?, 51 i 6.48 6.46 xic (Cl) 1 S il! LIt ¯j¯¯¯¯¯¯! ¯¯¯¯¯¯J¯¯j¯¯ ¯, ¯¯¯!

  <Desc / Clms Page number 219>

 
 EMI219.1
 1? Z '. 1 "- isostéa- <> I CH - T02 1) i Bicolioe! Benzene at 1 2} 1.51601! '72.18 j 72.31! O, 25 l 1.0.49! t '6.48! ! '6.32 1 ri que (el) ca <"= * '' <C "3 lIt i of oil of 1 RHcH i 1,. T 1 1 1) 24 1.5137! F! 1 1!, T 1 A) 1 ± ¯ Î! 1721: Oil acid;

   CH Qi Trinétby1- Benzene 124 '1.5137 Icarthane (C1) amine carthane (Cl)' 3 t "= <NO "'2 1 oeane!." 1 dd -173] 1, ± oil cide NH # - NO., 1] µ l Tri ± thyl-' j to j Ether 1.5123 'ï 1 q 1 É, µ ..? 3r, 'c.ae & oja of -o-No2 oil! i hyl-Ether; f r F 20 1,, 5123! ; soy (Cl)! soy amine (C1) 'Cil \ == / j) snine f j: µ,' '/, j) 1 i 1 j) J 1 f. j; 1174 = Oil acid N, CE-Benzene; 1.5094 -. L! ' l174µ acid 'oil BpjCE ± / 1 i Dinétbyl- / 1 1 Benzene 509V)'. ± 1 .l174î Oil acid from t #L N0 i starvation Benzene 24 l5094r) j ::: 1 '* .lli * <3 2 J Water / J 1.51-211 '! bzz: .ot- #j ** te:! 1175 'Oil acid from t! CH02 j Hydroxide Water / i 23 1.51211? . :! castor (Cl) 1 -002 Ide potas- itétra- 1 l .... i = C93 isium liyd - = - il..f: furan 1..j. ... the r5.

   Oil acid CH 0 fit 22 1.5115 i - ± f Z 1 J75J NIL oil acid 2 = Bydroxide: Water / ele 1.51151: raais l '5b -' 2! sium de potas- f dioxane f i C3El i: sium! j.



  -------- ¯-.l¯-- ¯¯¯¯¯¯¯¯ ¯..¯..¯ .¯¯¯¯¯. ¯ ¯¯ ¯.r ...: .. ¯¯ ¯¯ ....

  <Desc / Clms Page number 220>

 
 EMI220.1
 



  ------- - ------ 1177 i 1 Acid.d: 8oil of i T3H2CH /; ; ! Carbona # dei J 1 Water / acéiione! 22 1.5130! , cotton (Cl) OE3 N02 sodium co1: on (O1)! CH3 l 2 sodium Oil acid NHCH $ h0) /, Al-Methyl-Cafbonate 1,512 1178 Oil acid! N1i2CH..Q \ .- N02 -Carbonate dei lIéthy1- i 23 1,, 53.23t of olive (01) 1 'i! sodiua i isobutyl-) 1 "5 ketone 1179 'Oil acid! #: .. r \! pyridine f Ether J 24 1.51191 11? 9 d iin (Ci CH Ether 24., 5119; lin (Cl) CH3 t 3 -f! ÎIICI) / Tnmethyl- j Ethen 1,5l34! 1180 Oil acid # - <; TrinéthyI- 'Ether 23 i 1.5134! 1180 LCR Ether Hu-tie Acid! 23 1.51341 of rapeseed (Cl); CH .. 1 0 2 d! amine! I! .

   OE3! . 1131! i. ..1 oil acid 1 NH2CH --- ifOZ f 1; 1m1; 1-hyl: Benzene f f i 2fI. 5119J, its rice! f CH 1 3 l 1 Îftrnine! l j /; 1182! Oil acid i CH 0 -N02 t; P.1r1dine i i Benzene i 22 1.511Bi of chrysalis {Cl '° .-' a3 jL.o chrysalis (CI, k - 3 '; .- .. # L- .. ¯' i that, J i ± ' <S Plu ..

  <Desc / Clms Page number 221>

 
 EMI221.1
 1183 to 3HCH ± NO pyridine Tetm-J 1183; Oil acid from lOE2OE4 N02 Pyridi Tétra- i 22 1.5120! pleuronect (Cl), 2 j \ == hydm- C5 furanno i. 37.f34: - NH CH \ J NOg Pieoline Benzene Oil Itride 20 1.5138; 'shark liver ÎCI)] /' Î 3 'OE3 i135? ic; dc d'irilo do Î 1> niLu. ± P N z at] 1 Ipiridi; e Toluère 1 j Ô> '1 whale (Cl); C "3 = 'y *! 11Q6;

   Oil acid - EBL #) ¯ f 3xtimetbfl- 1 1 -; 22 1.5130 1186 NH2CFL Etbf oil acid; -. R 2; 2 .5130! cuttlefish (Cl) cy 1 m 2 iaaine GTt32 lia7 â c3.de of oil! NHpCH- <r- \ 'Carbonate ilketone 23 1-5221 sardine (Cl), - p ede potas- sardine Bzz iTO sittn Patas.- t3 ("Î Ù 1188 i Oil acid of \ 1 0 2 idine Benzene! i24 1, 5 1416 mackerel t 3; CH ,.

   ('## L naquereau y 3

  <Desc / Clms Page number 222>

 
 EMI222.1
 13.89 Oil acid of IzH2CH Pyridine. Acetone i 22 1.5149 'l190 Oil acid of ketone pyricline f22 5llàÎ No2 1190 hi3.3e acid of i NH2CH N0 2 Carbonate! . ! Acetone 24. 1,5118j! . herring (Ci), M3 = -.potassiun haronc (ci) j 3 1 É ipotassiuu; idinc Be) J24! 1.5139 1191 Y tacitïl: 'oil C1c =. 1UÒE ± '& = iàino Benàénc é 24 1 5139' j saurel! es. -2 'CH- 2 [if 1192 Oil acid NHCH - NO Decetoeic acid} 1.5159! 1192 4cidc of oil do GH ..-- T02 Carb,) nate de = ac; o.e: s 2, 1.5159:

   j 1 nenhaden (a) i lpotas = i'un nenhaden (Cl),) 3 = potass-ii l193 oil lcido 'NO2 lTniuéthyi- 1 eoluéna 51391 1193 Oil acid de = NH2CH..N 1y N0 .i .'riutb3- ¯ oluèna 1.5 1.391 liver tiorue (Gl) lm: iine liver uorae (ci) µ 3 1 Î lanine 1194 NE2M oil acid ± Water hydroxide / 23 1 5220 liver (Ci) E; 02 i j of sodium 1 1; dioxanno '

  <Desc / Clms Page number 223>

 
 EMI223.1
 T 'j 1 j,.

   Z: 1195 -CH-o-lfO2 -Dimethyl-carbonate oilicide 1.5130 'in (Cl) i 14' potassium fisobutyl- 1 EC [1! ketone! 1196! Oil acid NBLCH- -N0-; Pyridine Ether i! ! 2- l, 5135i 1196! residual <gui> 1 CH-o-: N 2; Pyridine Ether 21J. 1.51351! residual (CI); OE3 \ == É ô (; j 1 j Î O

  <Desc / Clms Page number 224>

 Example 1196
34.4 g of isostearic acid and 9.9 g of cyclchoxylamino were individually dissolved in 30 ml of dioxane. All stirred. At room temperature, the solutions were added to a solution of 26.1 g of dicyclohexylcarbodjimide in 30 ml of dixoane and the mixed solution was allowed to stand at room temperature for 8 hours. In the solution. 5 ml of acetic acid were charged and again left to stand for a further 2 hours.

   Then, the dicyclohexylurea was separated by filtration and the filtrate was concentrated. The residue was dissolved in 100 ml of ether, and the ethereal solution washed with 5% HCl, 5% NaOH and water, then dried over anhydrous sodium sulfate and then it was concentrated and distilled, to obtain 36.2 g of a desired product of a PE of 200-207 C / 0.07 mm Hg.



  Elemental analysis:
 EMI224.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 78.84 <SEP> 79.04
 <tb>
 <tb> H <SEP> (%) <SEP> 12.96 <SEP> 12.63
 <tb>
 <tb> N <SEP> (%) <SEP> 3.83 <SEP> 3.79
 <tb>
 
Examples 1197 to 1237 are shown in the following table:

  <Desc / Clms Page number 225>

 
 EMI225.1
 r ###########! Agent of ; ¯ C J¯¯S ho 1 'l Amine condensation,' Solvant l / Îi1 Theo-: -pinaly-- Theo-t! ? BNCNB tick tick: tick tick: t z.c- t'4-quc 1197, ¯cH <3 Ether i 77.48 '(77.29 13.32 f F 13.09. -: 4 3a 4 335 C "3 jj, 1 jgj) j, j] j),; 1196' NS -O; # Ener 77 , 10 76.83; mf 4.48 1198. 3 Etner i:? 7 1C, 76.83 13927. (15, a8) i 4, SO.



  CX inL, CH # = # L, Ether 77.95 77.77 12.77 1 4.16 i19j mycxcHmoe # "Ether 77.95 77.77 12, ?? 12.57 4.33 4.16! 1200! AH ( CH #)., Tôtrahydro- 79.27 78.94 12.47 12, 09 3.85! 3.67 '' OE (CH2OE-OE2 2 '#' furan "7894! J, 12oi NH2 ± J j) j 1 (Dioxan>? as6 f? 8s31! 12.90 12, Ï6 3.98 j 1 3.79

  <Desc / Clms Page number 226>

 
 EMI226.1
 s, 100here., ... ,,. i., ... a, ...,.,. o .. ,, .. ". =., ai" .......... ,,., y., .- .. ¯¯ "" ,,. "., ..". ".,.



  1202. '2 / S. -Q Siarno t 79.09! , 73 d! 13.01 l2, C4 3.69 3.4! II '! j 1203 m) cs% 1 1? 9.4l i y't3 'j! 13.76; '3.69 3.8? '1203! : ae'no 79.09 79.41 1; .. 01! 12.16; 3169 3.87! J / *** 1204 - (J-OË: l. '"! Il, 1 .g4: 3967 if: Tolu 783! 3' 143! L, 1 123! 3.4 3.16 1205 aOQH: F \ jl '0 Tol6o 7ta ;, 7S, S3: 12 43 "1 12, gO, ,,, J, la" l! (J: f 1SO @ <JeasM ëg.! $ 98 0. 10.33! 3! 3.09 la) 1, ja / \ '1 AüUh 00 "" 80.17 111t /11.491' '.' 1 'l', 41! 'mf,. 1,., '1.-.-.- K <.M ..: x = asz = ¯¯.,. ¯ 'iL4.y.s.L --.... "," "- .: J, - <.....

  <Desc / Clms Page number 227>

 
 EMI227.1
 



  # ---; It -. ,. -. n -r ---! the f. ! i "1 i. ..." ..... l f W t '1. mgJ-1-ca ç, moxann / t j ao, o '1 j i i ni, 05 1 f - n.w ,,,? 1 '3, this 1208! 3 'ec 3 Dioxaimc / 80.9o! 81.05! 11.88 j 11.56! 3.37! 3.02 f 1 '' = '5 L #! , F3 t ryridine fi! here : ! 1 t i 1209! 1 1 xHz ± J- ce 1 fD f '1 Dioxane 80.15! i 79.78 ¯ '11.49 t 1 rI 1.22! , 3.9Q I! 3.77! ") .. rrrr j:.: 1: 'Ç j \ JJJ. fi.



  1210; rg%) "t 1 ± fi Tc.3'r 15.6..i?; Jo; 0; o,>; io, 08 j, 3.43 3,> fi>; 1210!: m: 2 -") T..ë- ± 7.'C "Ú- :;? 3,:! .. '1230: 10.30 OJ, 08. 3.43 3,'! F ' <- \ =. = <\ # 1; # 1 j j .. 1 ial i! t- "Àcé 'i! i! 1 1 ... 1 7l' if 1211 2 -, - ('Acetone t! 76.33 1 i 7659' lQ, 6x 1 10.23! J, 71 i 5, 69 j, j 1212J. '. En: èna. 65.75 65.49 9.13 9, C5 3.19 1 i' i 2 't <± Ô-Br iJ Be = èna 65? 5 5 9 9 3 '9' 't' '') He! ! 1 thread 21.3; C3 DI Tetra-: 70.25 '70, o6 9.6 9.08 1 1 3, ") t 1213 \ = <\ ¯ / hydro- 70.25 70.06 9.36 3.27! , 06 hydro-: furamia j j 'j,' 1 fUll j, <j '- j, 1' t

  <Desc / Clms Page number 228>

 
 EMI228.1
 + f - t 1 ..... r.,. ¯¯ ....,. ¯ ......, ...... w..x.¯ .......... ,, ........ ¯. , .. ¯ ... ¯¯ ....



  ! 1214 m - / - 0 t. Dioxane .. 1. fi 76.83 11.13 11.00 3.60 3.33: 1214 i 'W $ 00E Moxanno> W, 07 1 6.83 1 1i, 13 u, 00 5.60 j, fi , "i 1215. 1" RB20 OEt 1 "-0 1 1 Tol" "". f! f j 77,%) 1 77.14 1 11.24 J 10.98! 1 l 3.471 3.09 j 1216 aN 1: f EtM-! ; TB.a? '! 76.00; t! IS,?! 4.1 :. 1 i 1216 Í! IIlJ .., g - "Etb '"'] e.Z? : 73.00: 12.811-! 2.73 4.1 'i A'J? t fl ca,! , t 1217 M # -CM .tt 3 j Diûxaaae t i '? 6.56? 8! 1,901,71 3. * 3. ] * ""! -y CH) f 1 i il. ')) igla) 1- ± µ' ") '/ éj, ¯ µMy,? µ f p, pp' t read Iii Il! Ô1àùÎ] ik19 j) (, YN ± J) 'hmaene;

   '? 8.84 78.88 i 1S.96 13.15 3.83- 3, SÙ ccur, ss.ccaa.css, w.yaasa-.u --.... = sacawoaraacirs.wicr ¯ ... ¯. .-..... ¯ ..... ¯ ¯ yi .... ....-. '¯

  <Desc / Clms Page number 229>

 
 EMI229.1
 r- "-.¯- .... r," "" 'F 1220 d NHpCHy Diox & BM G0.37 80.03 11.60}' '- 3.75 3.36 1220 22' f ". o%, 3? I30, o5 j 11.44 3a? 5 3s36 1220 # t. Jssaf ji jr Dionnne j "? ) î; ! 3.75 j 3.36 f: r! 1221 m (C3-) - / "\ Chlcroo: I.'D (J! I 82, C8 fi '! 3,09 10,65 10,33i 3,02 3,20 izzi! F - C2croforo J sz, x8 j, xi, 09 f io, 65! i 5, zo! j!) 1222 HE 2 1 t '60.4 ?, 80.32 12, t3J *; 12.45 j, lj; 3 ,,, 1 1223 mOEg 1 ± J 'ioxam:'! C0.56) S0.19 11.70 11.46 3.61. 3.39 Iii fit 1223 mr2 J \.

   Dioxane 00.56 t 00.19111.70 11.46 3.61 3'391 Ii! f Î 1 J) 1224! NH2GH D Chloroforae Cl, 14 t "61.04 11.35 1 11.05 3.5l! 5.461: 1224 c S * # 'chlororoxne j 81.14 81.0%) 11.35.05 3.51 1 1 C. l,, i 1 1 1 1 Ii 1 1225 CJ! 2-o-OI [-Q Dioxin 1 7l.0? '16 .87 11 13 lui, 02 3 60 3.4 & ... ¯ ...... ...... ¯u .... ¯ .. ¯ .y .. ............ ¯w.¯¯.¯.¯ ......, .. ¯ ... ¯!. ¯w.¯ ... ¯ ....... ¯ ........ ¯ .......... ¯..¯ .... ....... ¯

  <Desc / Clms Page number 230>

 
 EMI230.1
 j: ..¯ ¯ ¯¯¯¯ ¯¯¯w ¯; 1226 '22- ² f Chloroform: ± 80.56 i 80.31 Î 11.70 11.44 3.61)' 3> 49 1227 j im-CH,: -)! ! Ether! ! SO, 96J: i 80.44! 'j j i 11.70 11.49 3.61 3.50! if! 1227 m2cJL -o- CH%; -0 i J Ether Ii 00.56 80.44 Il, 70. 11.49 3.61; Î (3,5 --- z; JI 1 .. 1 1228,! CyO # J i \ ... fj! Dic.io?.eft, 3; f;?,.;? 8! J 13,2v ; '1, 5 3.47! Ttj 1 -' =. R!:

   ! f, 1 I! j 1229! -0 '-0 6! I! 77, CX3 11.24 11.4! ! '! 3.47! l J. 1229: N.iLGH- "1-;:: T6c: ..-? '7?! / 7.00! Îl, î4 11, (14! 3! J +? X.59) -" "2 ... "" \ ..- :. 1 - 'h "" d ..- o-: ll, t4 .1 + 7 x, 9 cf) E ± 3ze ..' f 'CBLO "' furamy Il! i fi! : .2 1230 N3-Q 25 0! Tolè 75.22J 76.49 12.55 12.33 3.42! 3.62 1231 Benzene 80.11; 79.87 13.22 13.04 3.11 3.00 1231 mhci + z5 Bezé e '9.8? j i '> *) i "," J 1 1; 3, ii fi f 1231 f C1ii25 i: Benzene 80.11: 79.87 13.2211), 04 jf ", 11 3.00 '" T' '-----' ----'--- -'-'--------- "-------- '---- ..' i -" '- -.-- O-

  <Desc / Clms Page number 231>

 
 EMI231.1
 -----..--- .d-. 'here' '' 4 '"t -" 1232J OCR., Ether 75.89! 75.59 12.06 3.54, 3.62 1232 -Ó 'Ether'? 5, $ 9; 75.5 "112, 12906 3.54 3, 62 1.-a '. J' 'j Ô µ];' 1;;. Ether 70.25 69.93! 9.36! J i 8.99} 3.27! 3.49J 1233 -Q Ether, 69.93 9.36 8.99 3.2?; 3.491 i ¯ '.

   CF3! ! 1 1 t j '[1 1234 IDL-c :: I2-' i - <) ± 3 TclJèna 80.55 80.28 11.70 11.56 3.61 3.38 12, x4 -2 2 \ == /) '"' * '"; "'") # i! 1235 <NHaLf "HO \ #. Tetera- 77.07 76, G5 11913 10 t76 3.50 1-3.291 1235 t. NIL, -b '1 J \. Hydro 77.07 76.55 Il, 13 -;, 60 bydro furanne s tif 1236 h'H2 CI -0 Benzene! 73.61 73.49 10.30 10.06 3: -3 3.06J t! CH3 1! t tif j.

     l i j! 'J CR f! f wire !! oz i 1237 NB] 3. -C \ Dioxane 73.1SJ 72.94 10.16 10.00 3.55 3.50 3 123? 11-Qm # D.ozsnne (Î3.1 ¯ # i? 2.94 i 10.16 10.00 3.55 3, j¯¯¯¯¯¯j¯¯¯. ¯; ¯¯¯¯¯¯ ¯ ... L .-- .. #! ¯ -..- L ......-. <1> .......... ¯¯ ¯¯¯¯ ¯ ¯¯¯ ¯ '¯¯ [¯

  <Desc / Clms Page number 232>

 Example 1238
For 8 hours, using a water separator, a mixture of 10 g of isostearic acid, 5 g of cyclohexylamine, 0.2 g of p-toluenesulphonic acid and 100 ml was heated. toluene. The reaction product was worked up according to the usual methods, to obtain 12.3 g of a desired product with a MW of 200-204 C / 0.06 mm Hg.



  Elemental analysis:
 EMI232.1
 
 <tb> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 78.84 <SEP> 79.06
 <tb>
 <tb> H <SEP> (%) <SEP> 12.96 <SEP> 12.83
 <tb>
 <tb> N <SEP> (%) <SEP> 3.83 <SEP> 3.78
 <tb>
 Example 1239
While stirring at a temperature of -10 to -5 C, 5.9 g of ethyl chloroformate was added to a solution of 14.2 g of isostdaric acid and 5.5 g of triethylamine in 100 cm3. of tetrahydrofuran. Stirring was continued at -5 ° C for a further 20 minutes. Then, while stirring at -5 ° C, 6.0 g of [alpha] -methyl-benzylamine was added dropwise.



  After the addition, the cooling bath was removed, the temperature gradually raised and stirring continued. Then, the temperature was gradually raised and the reaction mixture was stirred at 40 C for 20 minutes. After cooling, the tetrahydrofuran was removed by vacuum distillation and the residue was dissolved in ether. The ether solution was washed with cold dilute hydrochloric acid, cold aqueous sodium carbonate and water, then dried with anhydrous sodium carbonate. The ether was removed by distillation and the residue was distilled in vacuo, to afford 15.5 g of a desired product with a m.p. 200-207 C / 0.02 mm Hg.

  <Desc / Clms Page number 233>

 



  Elementary analysis!
 EMI233.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 00.56 <SEP> 80.71
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 11.70 <SEP> 11.70
 <tb>
 <tb>
 <tb> N <SEP> (He ') <SEP> 3.61 <SEP> 3.58
 <tb>
 Examples 1240 to 1307 are shown in the following table:

  <Desc / Clms Page number 234>

 
 EMI234.1
 y¯ # 1 C% Î H% 1 N%; 1 :: P.

   E. ; : ------------- f ----- - --f ¯¯.a. --i? 0 / Theo- i Analy-i Theo-: Analy-i rJn..é '1i ..... 1¯': No Amine fi C t1I1 Hg Th 0- Ana1y-: Theo-: naly -!. &. u o -: - t: rique; tick; tick tick; tick risk --- ¯.8> .4 "'- --------------- ti ------. i ------. ---- -; -----; --- 1 -120 1 "NH2CH <CH. 1g0-20Jrr0,03 - ## j # - # t I3,32 '13,' - # -; -s2 $! -1240! NHpCH 3 3 190-2O5 / O, 03 '77.4! i 77.57! 13.32 13.64 j j L, 0O j i 4.25 "5" 1 i 1241:

   NH.C, Semi-solid); 60.11 80.25! 13.22 13.42 3.11! 3.05 I! 1241 NIL, C1-tr25 Sernisolid GO, 11: 80.25; 13.22 13.42 3.11! 3.05 i 'I 1 (lj' '1 t' tz? "Lt 1242 NBCH-CH = CH 192-199 / 0.04 77.95 'j! 78.20! 12.77 12.89; 4, 33 4.07 1242 µ hHjCH-CH = CH 152-199 / 0.04? 7.95? 8.20 j 12.7 t 1 12.89; 4, µ3)] 4, O? J 1; j .! t, f ', ii:! 1 Ii;' 1 'i 1243 Nn <CEL 188-194 / 0.04 77.10 77.25 13.27 13.42! 4.50; '. 4.46! 1243 1: tm <-:> CH! 100-194 / 0.04 77.10 77.25 1 - 13.27; 13.42 14.50; 4.11-6 #! !! . j 1. ! <SL) -CH = CS: 12 ig2 -CSxCH 2 1S2-203 / 0.02 !!: j 12.54 1244 Cg2 CS = CFL2 192-203 / 0.02 75.27 79.44) 12.47 12 , 54 3.85) <3.63 thread 1 CH2-CH =; j (i l 1245 1 ' <J 20o-.2os / o, a6 78.58 f 78.63 112.90 13.00 3.98 3.89 i j 2O0-208 / 0.06 fi,! 1 ¯! ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯! ¯¯¯j¯¯¯j¯¯L.¯L - # i # - #

  <Desc / Clms Page number 235>

 
 EMI235.1
 1 i; 1 t:::! 1246.

   NSy \ 200-204 / 0.06: i 78.84 78.95! ; 12.96 5.83 fl 1246 D! 200-204 / 0.06 78.84; 78.95j = 12.96 '..: 13.04 i 5.83::;, 891 1247' NH / V '".-" - 202-207 / 0.05 f 79.20; 13.01: 13.43; 3.69 '3.52; 1:; 1211-7; 1III:! O 202-207 / 0.05 79.09: 79.20:! 1.01! 1.4 .6 "; .52!!,.



  "f # ±. r!; f 1 NH B 215-222 / 0.05 180.47 80.60; 12.93;., 1:; 1 3.09! '! j 1: ': damn 5 t' CE, Î t 1249! 1 'I # (** - 202-208 / 0y05 1 j 79.09 79.21: j 13.01, 13.01 O 3.69 3:59 j 1250;' fld 3 204-210 / 0.05 - '' = 79.09 '79.20! {13.01; 13, C5' 3.69 ii 1m2 \ ...) - ('204-210 / 0.05 9 "+,! L3 /> 1 ;: 3.59; t Nez -2IOrO, Or iir '?', G'j. # F ± ±;; 7i, 2J; svii 3.03.! I 3, Cç sr I ± s) t 1251! I NH2- --c 't 203-214 / O, û5: 79.09!); 79.13! 13.01 13.05 f 3.69 j 3.57 1252 NE * \ so 200-205 / 0.04 75 , 53! 75.60 12.41! 12.57! 3.67! 3.55! 1 "2 * h at 2 2 5% O4 / '75'53. 1 j? 5'6 j g 12'41 l2'57 [j 3 $ 67 j 355 1252 NH2 200-205 / 0.04 75.53! i ... 75.60 12.4J. 12.57! 3.67 3.55 i ## /, .. i

  <Desc / Clms Page number 236>

 
 EMI236.1
 "to H 5 5 '' '3'? 35; 1253 tti 201-206 / 0.04 .. 75.53; 75.55; 12.41! 12.42; 3.67 3.58 1253 - (¯ / '201-206 / 0.04 to 75.53,;

   75.55 12.41; 12.42; ! '* i! r! 1254 I --- OH 200-208 / 0.05 '7S, 53 75.54 12.41 12.56: 3.67: 365! 1 bzz ") 2- t - /> 5] ')? 5.53) O j 75.54)' 1 12> <1) 1 [12.56) 1 3.67 '/ 5; 65) j j 1255 0 -¯! i'm 202-210 / 0.0 ''! '75.89 {'. i 75.34 12.4C! 12.55 3.54! 1 d - -5 "/." ? 5> 59; '? ">?) [12>' 12> 55 '. 3,5v' i + j 'f 1' 'Î j' ['' to i 1 1256 1) 'Ô - :; 2:> 3- 21; YO, () 5 1 75.89 75.95 j 12.48 12.58! 3 ,; 3.45 Il!!!! J µ j Î] 'O () 1 1 j, 1 t. 1257: { ) -00H3 2:> 2-2:> 9/0, (\ 5 75.89. & 76.0L :.! 1 l2.40 l '! 12, (. 4 i. L 3.5' :. 3A91257;

   NIL, / -. -OCH 232-239 / 0.05 fit 12.64 3.54 3.49 1 1258 Nü2--17C 200-214 / 0.07 1: j 12.55! rice 3.42 3.40 oe z -; 1 j l 1 '., i 1 1 j i i 1259 NH2 204-210 / 0.06 80.3%> 42 11.60 f 11.58; 3s7.5 $ 1 ¯¯¯¯ 3 '.... ¯.,. ± ¯ ¯¯.¯¯..f 1 1

  <Desc / Clms Page number 237>

 
 EMI237.1
 ##;###########not a word-* ! 1260 ', x% ri oz-zwo, o 80.37: 80.53; 11.60 j 11.69) 3.75 3.73 --- \: J 2o2-2eJo, oS 3,? 3 'tif t 1261 iny \ -CH- 202-207 / 0.05 Eo, 37 = ± 0 = 38 11 , 60 11.78 3.75 3.55 [Î 1261 1 Î ùpzcy¯ 202-207 / 0, 5 N 8> 37 00.38 11.6 Il.78 3.75 3.55 --2 \ ==! 1262 '' 1 j 3 205-214 / 0.06 j 2 "> 11.58) '1 3.38 1262 - 205-214 / 0.06 80.90:

   81,16 11, ô8 11 Il, 98 5,?;? .7.53 it! ! 1263, HO fi '210-215 / o, 06 f J Go, 15 50> 29' 11.49 (3, JC a! 1263 1 1- 210-21.5101106 1! V01l15 00.29 ¯ li, 49! 17- sfi: 'i 5, '30 3.84 1264 NHy-OE 211-217 / 0.05 80.15 80.37! 11.49 11.58 3.50 5, GS ize *' m% g <u zu-z17 / O, 05 t g j 1 so, 15 8O,> 7 11.49 s, 58 3.55 5, GS 1. .

   J.264 1III;, - (} # 211-211 / 0,05., T OO, J.5! OO, 1].]., 49 i! U'58! 3,90::;, ôS 1265 l 1 mL el - 205-214 / 0.07 73.18! 73.44 10.16 ii 10.27! t55! 3.49 l 3) Î j 1 ti! J !! 1266! 1111;, - 6 cl 204-218 / 0.06 i 73.18 13, rYl 1 f .. É 10.16 10.32 \ f 3.55! 3,116 \

  <Desc / Clms Page number 238>

 
 EMI238.1
 1267! 'HHy-d f 10.54 3.55! 3.39 1267 1 yz j, ç 20-214% 0.06 f 73, -8> a 10.16 ± I0.54 e, 55 3,, 39 \ == Br 1268 Na \ Br 204-208 / 0 , 06 65.75 65.65 z-3 - 9.29 3.19. i>, 08 the i ' <'Ff 1' j 1 1269 1 0 mh- 199-204 / 0.04 76.39 76, U 1, 1, 61 '10, CK7 3.71 3 <52; \ == /> 1 j j 1270 i 1 t RH ± Ô 204-214 / 0.05 'I3.61. 73.30 1 10.30 Io 52 3, -3:

   3.36 cs "* 3 f 1271! ICL-y-CF- 202-20S / 0.04 70.25 '7C, 5 9.62 3.27' 3.13 - 1271 ci? 3 2 ?? - 2JS / 5.0W 70.25 7C, '> 5 d 9,% j 9, 6? 3> 2?], 3z13 12'72 NH- 208-214 / 0.03 70.25 70 # 40 9.36 19 e48 3.25 3, C5! 2 - '/> 3? 0.25 j? 9'! I, c5 * "? ! 1273 ci J! 206-214), 06 I 73, i t t 73.7 1.30 10.45 '3.43 j 3.38

  <Desc / Clms Page number 239>

 
 EMI239.1
 1274 BH <"3 200-213 / 0705 '79, 09 79. 13, 1 1 3 90'7 3 9; 3, 56 OE3!! 1275 NH 204-223 / 0.05 82.70 82.65; 10.41 ! 10.65 '! 3.22 3 a 7.8 1275 204-223 / 0.05 82.70 O 10.41 6.5 3.2? 1.18 1276' ¯ IBp-Q "203-203 / 0.0! '77, D7. : ', î4 11.13! 11.24! 3.50 3.53 j 1 0276, '\ = N' 2O3-2O81a,? J 77 der (,? 7, Â4 l '13 li 24 3, s5 j 1.55,; jjj ooe 3 1277: #Iy 201-209 / 0.0 :? 77.7, 77.18 '11.13 11.28 3.50 5.42 127? I 2 ¯' "''? '/ J"' 11.13 11.28 6,.



  == - 1278 iH2-F-j 2c0-.a.?f0,t'i,j '77, li,! 'L. s..i 'n 11.13 11.2i5 J,; x'. j 1278 j j 1 ± 200-2JL2 / 0.05 77.0 '/! 77.35: 11.13 11.25 j '3, D 5.49 1279 F: rr OC 1 5 204-214 / 0.04- 77.36 il 77.41 11.24 z, 65 1 t' 3 ,. 7> 1280 i ISH2 oc 5 200-220 / 0.08 j 77.48. =. 7.1.24 11.36 3.47 Î

  <Desc / Clms Page number 240>

 
 EMI240.1
 ; "7" ## T # '"" ## "### r 1281:; 1-i-, pC' 199-209 / 0.08 77.36; 77.45 11.24 11.2i3 f 3 , 4i 3.2+; / j 1282 HBT / j 203-208 / 0.04 78.27 78.50 1 12, - I I2,: 4.1.5 3.98 \ *** '!!! Ifii * 3 l'l'b 2 -2 8 /> 5? 8> 56?,? 4 '12, S 13, 8' 3, *)?> B9 i283:

   HD1 200-2O8 / OsO5> 6 i% as? 4 12.90 113.08 $ 3 98 3, b9 200-215 / 0.05 Jf3s $ 12 96 13.08 3sess3 3.45! "" 7,200-215 / 0.05 78.84 78.82 12.96 13.03! 3.45! Î j Î 1) 1 EN 0 2C) 6-214 / 0,, 06: l -, 'J3? -S52 12.26 12 57 3.95 3 1286 j / mha% / Ô 201-208 / 0.05 / 8> 37 '80.64 11 60] U 8 3.75 33.50! J 1287 NH (C82) 2218-225.06 J 82.88! 82.98 f 10.65 10.90 '3.02) 3.00 1287 NH (OE2n l-5 /> 82.88 /, 58) 1 55 10.50 3 2 3, C) 0

  <Desc / Clms Page number 241>

 
 EMI241.1
 i f laughed. j j i 1288 j it! NB2CHO 201-212 / 0.05 1 n / a, 56 f 0 "8O, 75, 1 11.7o ji 11.92! 3.61 j 3.38 1.209: fil i, mL CH3 '' j 203-208 / 0 , 05 it 1 'J i 81.24: j 11.35 j Il, 48; f! ---, r ""' ==! 203-208 / 0.0.5 81.14 tl, 2j + '11 , 75 l ', 3s58 C! 1290 O 2I4-219 / O.C4 77, C7! 77.26 11.13! 11.25 3.60 37 ii' {; 1290; eB2 a "'; 214-219 / 0, C4 '? 7 t:, 07: 77,26:

   He, 13; ! He, 25 3.60! ,; hl1 ,? t,.; . '' 'Î 2%' 'l2l% /> C4 * t,' .. 1 11.25 d, 60 d, 1 3,% 7 to 1 fi z293 'Î' 22flÔ 1 209-219 / 0.05 1 ',, 77'26 / lls13 t / 11.34 i 3.00! 3, -5 1291 ooe j. l 209-219 / 0.05 77.07 71.26: Il, 13 j 3, ex> 3.45 ocg thread] '' i) i "'h 205-217 / 0.05 77.36 77.49 II, 24.1126 34?! 3:33! F 1293 lm-CH2 rj 205-214 / 0.04 j 71.36 77.50 j 1 'II, 37 3.47 3: 3? 1294' 2 '" '/ 5 77.36'! 77.49! ! '11.24. 11.48 3.47 3.44 29 ', ----' ==. Iu 1 1 1 ??. 36 1? 7s9: lI, 4f3 3.47 j î

  <Desc / Clms Page number 242>

 
 EMI242.1
 ï ------; ---------------; ------------ ----; --- 1 ----; ---- 3.35! 3.27 i j f 1295 J f -Q-oC 208-218 / 0.05 '77, 64 i i ,! 'J: 77, fA. 11.34-! Il, 34 i 3.35 f 3'271! 1296 1 yew! f 200-215 / 0.05 S 80.56 80.74 t j 1 f 1 1! J i 3.61 - 3.66 j i a2g6 '/ 200-215 / 0.05; 80.56 80.74 11.70 1.90 F 3.6a, 66 = 3,: t C "3 i!! J 1297;

   1 NIL-Ó 200-208 / 0., 04 00,56 i 80 ,. 11970 11.86 3.61 3, .5 i! ! ) 1298, â N'iGi2 Ç 200-205 / 0.04 i! 00.56: F''o, 58 f 1 11.70 1 11.94 f 1 3, l 3'36! 1298 5, r 3 i 11.94 -! Y j, i 1299 CH3 200-218 / 0.05 so, 37 80.39 11960 1a, 63 '3:.' S 3.65 1299 CE- - 200-218 / 0.05 'ji 80.37: 00 '391' Il, 63 .3:; 15 3,6.5 -ri l 'i 1300 1 NH: =: 201-208 / 0.02 80.73 80.82 Il, 80 11.94 3.49 z C5 1301 NH2 3 G03-207 / 0.04 80, '3 80.7a 11, DO 12.05 3.49 F 3.38 <=: xc "¯¯.¯¯¯¯, r'r ......... ¯.¯ - ## -. ¯ ¯¯ ..., ..,. ¯¯¯¯ ¯¯..¯¯ .... w, ..,. ¯ ... ¯ ....... ¯ ... ¯¯ ... ¯ .... ¯¯ ....

  <Desc / Clms Page number 243>

 
 EMI243.1
 



  1302! / j 1 xHzfi% Il 200-218 / 0.05 73.61 1 j 73 88) 10.30 J 10.56 j 1 ¯ 3.43), 34 t 1 f i -, C -! 200-218 / 0.05 ¯ i '13, 61 il 1 f! t 10.56 3s # 3 - f 1303 200-216 / 0.05 73.61 73.74 '10.30 10.49 3.43! 3.36 1303 200-216 / 0.05 73.61; 73.74, 10,: 10 1qu 3.43 3.36, 3 f! 1 /> / 1)),! ! 1304 -f 200-214 / 0.05! J 76.39 '73.61' 3.0.61 10.88! 3.71 1304 "200-214 / 0.05 76.39: 73.61.! 10.61 l, 10.88 3.71 3.48 1 to J, 1305 NHV'-Br 200-215 / 0, 05 65.75 65.86 9.13 9.23 3.19 3.47 1; 1305 R% ± -Bn fil i "1 65.06 'i. 1 1 i! 1 3.19; 3 200-218 / 0.05 73.61 73.75 t 10.30 i 10.49 5.43 3.18 l 'f i5 6' == (. "Cl! Fi 2lB /> 5! F ': 1 3518 =. Î: 1 * 1307 t '#LlJ 215-223 / 0.06 60.51, 60.7C 12.31 12.40 3.35 3.06 I! 1 1301! - @ 215-223 / 0.06 80.51; 80.76:

   12.31, 12.40 Ii 3.35 3.06 i F, = Î t 1 :. t

  <Desc / Clms Page number 244>

 Example 1308
To a mixture of 5 g of cyclohexylamine, 2.5% of trimethylamine and 50 ml of anhydrous ether was added dropwise at 0-5 ° C. 10 g of isootearic acid chloride. The reaction mixture was stirred at room temperature for about 10 hours and boiled for 2 hours. Then, the ether layer was washed with acid, alkali and water, then dried, concentrated and distilled, to obtain 11.9 g of a desired product with a PE of 200. -203 C / 0.05 mm Hg.



  Elemental analysis:
 EMI244.1
 
 <tb> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 77.48 <SEP> 77.58
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 13.32 <SEP> 13.41
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 4.32 <SEP> 4.16
 <tb>
 
Examples 1309 to 1376 are listed in the following table in which: Condensing agent: a. NaOH b. KOH v. Na2CO3 d. K2CO3 e. Trimethylamine f. Pyridine g. Amine in excess h. "IRA-400" anion exchange resin
Solvent:
A. Acetone
B. Methyl-isobutyl-ketone C. Ether
D. Tetrahydrofuran

  <Desc / Clms Page number 245>

 E. Dioxane F. Benzene G. Toluene H.

   Water I. Pyridine

  <Desc / Clms Page number 246>

 
 EMI246.1
 -...... :: J .¯¯¯ --¯ --- ¯ -.- 7 ---- Rd 1 -r: rd pie ...,. de f Solvent Es i''LéoI "T & naIy-! 'rn6O- Analy-ti & naly-' Amine condensation- ¯ ... ¯¯ rique - tique-- risk -tique - ri-que- tique-f - ## j # - # - # J jjjj 1309 1 NH2CH <# '3 CH A 190-203 / 0.03! 77.48; 77.39 13932 s i 13 6 4.30; bzz 1> 9 j Î xHzoe ± 3 * Il 77, {fit 1 4, * 1310 i rr2 g ± a f se, az.-so.ae; 'ao, m; 80.35 1 1322 13.40 3, zi i! 1 3 J 1; 10 i t? Se -S> de, 11) 8.? 5) 1,522 13> 1311 '1 NH2CH2-CR = ClL g 1 B 1,191-19S / 0.04 1,77.95; 78.21 / Î 12.77) 12, G9) 4.33 j Î <, 019. f 1312 N (3 gt JCJ! ICS-192 / 0.04 77.10 77.23 13.27 j! 13.41; 4.0 ji! 1 's¯; 1312 3 3 3 loe-l92 / o 1.04 I! T: 1 1: 1 1; 77.10: 77.23 i 1 1. 13.27! I 13,! H 1 i 1: 4, -5 <). 4.4t! - i 1313 2. "g2) 1 9- / ') 79927 79.41 * # *' '" ") j;

   '39, o., 1314 mr - G,. ¯ / 0.06 78.56} '78.62 jf 12, T- j 13.02 3.98, 89 1314 ma ¯ ¯¯¯¯¯¯¯¯¯¯LI - / o, 06 iz, 9e) J ! 3, a9! ';.' j --- ..a. ------- 1> .... 1> .. "" ¯ .....---- f¯¯¯IoI.A> -. "" "- ..." ",. ..11 ..........- -¯..4 -, .....--

  <Desc / Clms Page number 247>

 
 EMI247.1
 ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ .... - #### ------ .. '00- o,' - --------- t µ To this.



  "#" "# r" ### '; 1315; , he! 0 '200-205 / 0.06 76.84. 12.96 '13.05';, 83: 3.79. . . i3I5: i F ±. ! f ¯ '± i 200-20.7Cs'. '. J, f34 '1! 1 g '! i i i.iJ fIl t! if !! 1316: t 13.01 13.42 3.69) 3.5z [),:.,. i. ..: the i '..!. . ! 1 -: 'i 1317 NH <'=' CH e i .: CO, 4'1 80.61: i 12.93. , 3.13! 3.09 CH3; ' 1 t. :: i h $ µ (i é ''] <j Î 1 1 [) 151G J '-1 z; 1 i 2J2-2C1 U s05; ! 79.09 j 1 79.31 1 15, oi! t 13.21 3 s6cJ 5.5o t 1319! $ 1 t m! ZD CH3 '! 'I "!:! I! 1,204--2301 / 0.05! - i' i: 1,79, O9 !? 9.2G 1 fi;

   1 1! i 13.01 1 1 J 1 j 1}, U} 1 3, 69 1}, 5a 1320 î NH2 r- \ r1U Il t 2 -21l /, 5) 79.09 i 79.23 15, oi 1 J .3.05 3.69 3.57 t II! 1 '1 1 75.62 j 1 12.59 3.67 3.45 i? 2 -2 6 /, Q +? 5.53) 75.62) 12.41 iz, 59) 5.6? ) ,, <5 Í. ! 1321! "" 2 '\ ¯ / IIi J 200-206 / 0.04- 75.53! 75.62 12.41. 12.59! 3.67, 45,, 'z¯¯' $ É j ('i 1 ['

  <Desc / Clms Page number 248>

 
 EMI248.1
 1322 1 EH f j / HD. f 2oi-2o7 / o, ov /] 75.53 75.65 (iz, 41 12:% 3 '5.67 (3.5W 1322;' -J 201-207 / 0, () 4.; 75.53: 75.65; 12.41; 12,. '. & - 3., 67:;, 54; il.

   HD 201-207 / 0.04 i! 75.53 75.65! 12.41: 12.43, 6? ' 5.54 .. 1 1 F. t 't 1323 fiflzmH / zoo-zoe / o, 05 1 "j 75.53' 75.57? .. <'162', 57 '3.67)' 3.6z! j 1325! N $ 2-! j B 200-208 / 0.05 j f 75.53! "t 'y.? 5s5? ¯ 1 .2.41 M.57' 3sC? 3s52 1 j! 1324 j ($ 3 O 201-210 / 0.04 j! 75.C9.! 75.94 'f 12 , 48 l 3.54!! 3.53 1324 ib 201-210 / 0, C4! 75, û9 75.94 12.48, '12.57; 3.54 3s53 l, 1325; 1 1 Xpg + of! I 203-. ? 11 / 0.05: 75, B9! Jj 75.96 12µ4B) jj (12.66 1 j 1 '3,>' 3.45 f 1 1325 f! -6 'OCIL - 2O} -2l / O , 05; 75.89! 75.96 124B 1 '. 12.68 3 ,! 3.45!' '' <) 1 j 'f i f - t j r 9 = 132G j.



  ! 1326 boEz- CH- 1 2? -29 / G5 75, C9 76.01 12 48 12.1 3.54! 3 4B.



  1 1 j 1 '1327 in-J-OC / -. 200-214 / 0.08 {i! 76.22 12.55 i 1J27! -O- 1,200-214 / 0.00 76.22: 76.24112.55 12.6'1- J, 42 3, J4 Il! CIL 1ft 11wfi0 .3., GÔ 1328 1 '') # / 'J') "'")'? Î>? .: ...-! ¯¯¯¯¯¯¯ ¯¯¯ - ± ------------ L-¯¯¯¯- f

  <Desc / Clms Page number 249>

 
 EMI249.1
 v .. C! T ¯, 0 1 1329 j i * ''? f F! ; 202-210 / 0.05} 00.37 UO.63: 11.60! : lz., 9 3, '75 5.63! \ =! = / j É: '' l! ! t 1330 NH - CB:! 202-211 / 0.05 S0.37 G0.33 11.60; 11.75 3.75 3.25 t '' '' '/'! j "2 \ == / es- i 1 i j .." 1: 13 'f'! ; 1331 HHz ± -CH 1 1 f C! 205-215 / 0.05! 80.50 Fi 1.26 11, B8 i 11.97: 3.3; 5.33 CH-1:; 1) j 1 1332 j Hp 210-216 / 0.06 80, .5! 80.39: '11.49 11.62 3.90 3, G1 1332 n 2: 1.0-216 / 0.06; 80.5! 80.39: 11., 49 11, G Il 3.90 3.61 l i] j i 'l i. Î i * '' '' ", 1!" ") '' J: 1333 J f -o- #: if Î D il! 211-219 / 0.05 80.15} 80.39: 11.49! 11.5:

   s 3s j I} 68 fit 113: 74 Î i 133 1 f C1. h h II F f 203-214 / 0.07 i. $ 73.18 '4j i 10.16 Î iQ j') '' '$ 55 j 3.40: J 1335! J N3 Cl j e 204-213 / 0.06! ) i +? 3.18 73.47! ) (1, 1 "), t 1 1, 31) i: 3.55 1335 NIIz.-Ó 204-213 / 0.06 73.18 7}, 47 10.16! 10.31 3.55! 3.40 \ = = / ī¯l¯¯¯¯¯¯L¯.¯¯¯¯-L - # - ¯-L ## L.-¯! ¯¯L.-¯; ¯j¯¯

  <Desc / Clms Page number 250>

 
 EMI250.1
   13 "BH-f-Cl h - j j j" 2-2l3 /, 6) 73.18 i i i '73,; 71! j 1 * i 10.64 3.55 tu; 3.38 \ # Iii 1337 f;! 1 b 204-218 / 0.06 / '65.96 bzz 9.29 3.19 J. f t. 3.091 f 1338 NB-Y'-F 199-204, / 0.04 76.39 i. 76.58 10.61 10.83 3.71 3254 13> ¯ ci j) C) 199-2O / O, O #) j "76.39 76,>) 10.61 1339 NH-! 204-211 / 0.05: 73.61 '73.82 10.30; 10.51 3.43 3.37 '1 hH µ j 1 e) C Î j <204-211 / O.05) j) 73, G2 j) 10.30 J / 10.51) 3.37 1340;

   NK./'y? h F 202-21 5 / 0.04 1 70 e-5 70.65 1 9.36 1 9C2 3.27 3.07! 1341 NBy 203-214 / 0.03 70.25 70.41 1 9.45 3.25 3.061 3) j) 1342 /% / 5 on 1? 205-214 / 0.06: 73.61 73.87 j 10.30 10.45, 3.3 j 3.39 1342 lM2e 205-214 / 0906 73961 73987 10.30 $ 10 45 3.43 .3.39

  <Desc / Clms Page number 251>

 
 EMI251.1
 ; '13a.3 jj Î 1 "g 200-223 / 0.05 79.09! 79.34 13.01; l3, og 3.69 3.46 if! 1344 ri B 201-223 / 0.05, 82 , Jo 82.43 10.41 10.68 3.22 3.09 r \ 7 ü-ro Cil 3 '"2 9 /?> 5 ??,? 77.24 11.13 '11.25 3.65 3.58 1345. i f) 2 'x 203-209 / 0.05; 77.07 77.24 11.13 11.25 z 3.58 OCE3 1346 inL, - b H f 201-209 / 0.05; 77.07 77, .g 11.13 11.2g. 3.0 3,. '1347 1 (' '2ô + Cfl3 oc + aD; -2W-210 / 0.0.5 77.07 77.33 11.13 lle2.5 3.60 1 3.40 1348.! SD 201-214 / 0 , 04 i 77.36! 77.51:! 11.24! 11.63 !!! 3.47 '!! 3.35') BD 201-214 / 0.04-% rJ, 36;

   77.51 ll, c "t4 il., 63 3s''cT 3.36 1349, a BB 20U-22o / 0.08. I 7? 7.36 w, <9) Il 24 d 11.35 3.4, 3.18

  <Desc / Clms Page number 252>

 
 EMI252.1
 1350 i -o- Ci15) 199-218 /, 8) 77.36 f 77.46 11.24 11.38 3.47, '' ', 2:} 1351 1 / j f 1 200-208 / 0.04! 78927 78.53 12.84 1 Î iz, / 1/1 -, i) bzz! 1352 END 2X-2O8 / 0 05) 1 78 56 j) 78 64/1 12 90/1 13, 7 d 3.98 3.88 1353! BN e 2O0-213 / 0.05? 8, û4 78.92 12.96 13.03 3.83 3.46 1354 EN j 74.73 '1 12.26 13.54 j 1 3.65 1354 j' '' 74.73 74.92 12.26 5; &; 96 3965 1355 N3- <f C 201-201) /090.5 80.37 80 961 11.60 11.87 3 * 75 3.52 1556) hH <aU ± 5> z BE? l'-223 / 0.06 82.88 82.90 10965 ing, 94 3sO2 3.00

  <Desc / Clms Page number 253>

 
 EMI253.1
  <'he:'. ' . - 1357 j '-0 201.212 / 0.05) 80.56 J 1 11.70! 11.92! 3.61! 1;

   1351 NB: 2CH "== l 2Cf1-212jo, 05 00.56 j 8O, 76! 11.70 11.92 3961 3s38 OE3 '! 1358' OE2l b RD! 203-209 / 0.05. 81.14 1 81.3 ' 1-! 11.35 11.48! 3.51 3.50 CtfI5 if:.: I! Ott: .D.! 1359 NCH OH 211-219 / 0.04:; 77.07 j 77.27 11.22 3.60 . 3.49 1359 NH2;! EG 211-21910 .; 77.07. I 77.27 3 11.13 11.22; 3.60! 3.49 f il '1360 NH 2 "" pg! J B 209-218 / 0.05! 77 , or ??. 30 m, Z, x. 1.32 3.60 3.25 fi! OCE- Iii.



  OCI13 1361 NR2OE2b 205-21 8 / 0.05 77.36 77.49 11.2. at -6 3.47 3.33 1361 1 b 205-218 / 0.05! 77.35 ??, 49 111.211-111.46, 11.46! 3.47 3.33 OCR 3 It! 1 ;; 62 lIH :! 205-215 / 0.04 ?? 36 ?? 52: 11.24 xl, 3a 3.47 3.29 1 - (j 205-215A), 04 77.36 77.52 11.24 n, 38 3.47 3.29 1363 NH2Cg2 -OCH3 G 203-218 / 0.05 7713E-> J 1? 7.54! 11.24! ! 11.49 d 3c.? 3.1 i ....... w.m..n -., .. r -. O .--- wr.r.ww-nw. . !

  <Desc / Clms Page number 254>

 
 EMI254.1
 T "if T" * '"" * OC-Re - "i jt i 77.64!!) I! 3.29 1364 ML, 0 HE! 208-219 / 0.05. '77, 64 read 3.35 3 , 29 f, 1 1365 22% -5) -9 / 5 Il! Fil i 80.56 30.84 11.70 11.91 III '?) 3'9 1), "5)' 1 j Î).

   C HE]> 2 -213 /, 5 '. j 8, 56, "jj /, 7 11.91 5.6l) 3 t67 that- i! 1 t! 1366 1 NH2CH2 ri e 2CO-205 / 0.04! 80.56 CO, 72 11.70 11.90 39Gl 3.48 2 \ = vjt Il! 1367] ICS-CSL 200-206 / 0.04 ('t 6C,; C 80.63 00.70)) 00, S%) 3.60 µ, 35). T 1 1367 NH2-o- 2OO-06/0 () 4. 80.63 3.61 3.35! J. 3 NE 200-214 / 0.05 1 30.49!>.) 11.8; 3 ?.) 3, 67.



  , - 'CH3)) ";)'" 5 /% 201-209 / 0.02 80.73 1 80.82 11.80 11.90 3.49 3.16! 1370 i 1m2) d-ca., F y 203-209 / 0.04. ] 8,? 3 80.91 119W 12.05 3.49 3,>

  <Desc / Clms Page number 255>

 
 EMI255.1
 , .. l! ) 1371! ! /% flô-s! i 200-214 / 0.05! ) 73.S8 J 10.30 1 3.43 3.31, J! l 'ii "J ..' 1 1372 NH-f 200-217 / 0.05 73.61; 73.79 10.49 3.43 3.30 13? 2; 1 2 ibf ¯ 200-217 / 0, 05 73.61, s '73,? 3 i; ln, 3o ji: 10.49 3.43 3.34 1312! 2] 200-217 / 005! 73.61: 73.79 1; 1049! 3, 43 ji: zo-, iwo, 05 to / 76.59 1? 6,) ')'?) '') '1373 NHy f xo.-2z..lo, 05 r î6.39 it F '76, s2 . z0.6i; J 10.87 3.71 3.49 1: ".



  .374), - i C 206-20µ /, 5 /) 5 'i / [/ 1') 1 .. 1374: Br j 'c 200-213 / 0.05 j 65., 75; j 9.13 9.43! 3:19, 48 IIi j, 'f! 1375 ¯ c5 r 200-2i5A), 05 73.61 j 73.76 10.30 ic, 56 3 <45 3.19 B75 1 l A-c2% 2 - / ') i.! 1 7}, 61: Iii 'l},' l6 10,} O 1 (), 66::} .45 l 1! 3.19. of! ! ! ! 1376 i - <0 1 lL1 2J.5-22} / O, 06 1 80,51 8O, 'l'l! 12,} 1 12.42}, 55 1; t t J i 1:

   t 1 i l! '1!

  <Desc / Clms Page number 256>

 Example 1377
For 39 hours, while stirring at 150 ° 0, a mixture of 10 g of isostearic acid and 5 g of cyclohoxylamine was reacted with the water removed during the reaction. The reaction mixture was immediately distilled to afford 11.5 g of a desired product with a m.p. of 200-206 C / 0.08 mm Hg.



  Elementary analysis!
 EMI256.1
 
 <tb> Theoretical <SEP> $ Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 78.84 <SEP> 79.06
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 12.96 <SEP> 12.83
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.83 <SEP> 3.78
 <tb>
 Examples 1378 to 1428 are shown in the following table:

  <Desc / Clms Page number 257>

 
 EMI257.1
 "" 'Duration Temp- 1 C H H? E% Exem- of the erasure; l huto- j P.E. ¯¯¯ ¯J ¯¯) ¯¯j Lmine. rus8 tion = c with clnm E bzz¯¯ --------- s N ¯ reaction. reaction-., clave; 9 - Théo- enaly-t ÎÉÀù] Éiɵà 1 ÈÎÉI 'tiquai - (hours); 0), risk, tick; rique. tick: tick tick '1378 i! BH - Ca C3 20 1CO rti.ii.se = 187-201 / 0.05 =; 77 * 4û 77.68 'i 1 13.32 1 1 13,? 4.30 4.18 1'379 BH <, 3 ¯g 50 2cl; 'Used; . 130-200 / 0.06 = (77, lu: t 7Îs 41; 13.27 i 13s 0''T;

   i 4 9.5C 4 9 22 1360 lOE2OE2CE M2 1 80 'iused! 197 -? 04 / 0.06. 7? 95 78 g6 1z)> 2 51! 4 33 j 4 io 1381 BR (CHpCH #H) p! 50 200 used i98-? 00 / 0.05 79 * T '79.41 1 12.47 12.22 3.F15 3.58 0382 BH / 1 28 185 j! Used P-uu-207 / 0.05 '78.56 1778,? S. I2 * o 12. ?? $ 3.9 3.6W 23a3 ¯ ilH2? ' 150 None 1200 -212 / 0.06: 99.09 79.15 13101 Z2.89 -3.691 31> 43 1383 BBL, - ( <7 D! 150! ! Nil 200-212 / 0.06i 79.09 79.15! 13.01 12.89 3.69 3.43 to 3G4 'b 1 NHb 27 160 - 205 -212 / 0.07i 77 * Og 79.23; ¯ 3 - 13 * Ol f fi 12 "F, SG 69 3,4-5 L.¯.¯¯ ... ¯¯. = ¯¯¯. .L- L - # L # ¯. ## ¯ # L # ¯L ## ¯L '' ¯j¯L

  <Desc / Clms Page number 258>

 
 EMI258.1
 ¯¯¯. ' ! ! j / µ 1385 j 1 (n ± dqi 25 1s0 I i '202-2o9 / o, t ??,'. f; 7t3s9 79.32 j 13.01. 7l.2.9x 1 3.69 3.42 j 3.386 j 10E2-0- OE 1 25 160 i - iz 200-210 / 0.05:! 79.09;

   1 '79.51 j 13.01 1! 12.37 j 3.69 1 f 3.531 1387 wHzJ "28 185 / J zoo-a5 / o, o6j '75, 89 i i 12 v48 fi 12,) f 1 - \ Î! 1 j l: 1.



  1387 j 2 26 185! -! l '205-213 / 0.06 75.89 t 76.02 12.48. 12.40 3.5; 1 J ', 26! He! : "I! J 3 OCH- 30 185) 3 /) 75.89? 6.04 x2 .r3 12.2G t 3.5+ 1 1389 'Nh - Pb 29' 185 -! 20C-21G / 0.05 ! i Iii. 75.89 76> 60 12.48 12.19) 3> '3.3.' 1389 -o- .1 1 l 29 185 j! 1,200-2113 / 0.05 75.09 12.413 / 12.191 1 (3.54. 3.31 1390 --oc5 29 185 - 03-.209 / 0.0. 76.22 j / 76.4o 12.55 i 12.28 '3.42 3, io HO If f '11391 29 185 JI200-21l / 0'O 75.53 75.75 12.41 1 12.06 3, s? 3137 If!:.! i # ¯¯ī¯¯¯¯¯¯¯.- J¯¯¯¯¯ī¯L -.- ¯¯ -.- J¯¯¯J.¯¯¯¯ #LJ.

  <Desc / Clms Page number 259>

 
 EMI259.1
 



  ...,,.



  : 1352! i BH - (- QH 29 j .a5;, - 2002og / o, os: I5.53:? S, $ o 12.41! 12.58 ii 3! 6? ± 3s 1 1, 1 j 1 tl ' j; 1 i 133 ': N- 3 32 180! l99-208 / 0.06! j 1 0% -208 / 0, C6 "F so, 3?! 80.46 il, so, az, -a: 3,? 5 3.52! 1 1393Ï 100) t 199-208 / 0.061 'z: 11.60 1 11.41. 3.75; 1: 1394 2 i 32 180' = s 200-211 / 0.05 = Bo, 3? 80,54) zl, 6o:,. 3 f 3? S,. 3,5 'i !! 1355 * h4Ô-h /' '52' 8)] È '3? "' 6) f 3 '±' 9 1395 --- 3 180 - 1 80.37 80.63 tif 3.79! fi! 1396 OH 185 210-231 / 0.04! 80.15; 80.43 11.49! f 11.25 i 3.90 3.47 l96 lHgb '085) 80> 05 80> 43) 01.49 ll, 25) 3.9) 3> 47 1 t 1 i 1: 597 MIz-Q- # 30 185 - i; , 1 1 200-222 / 0.041 f- 1 f 80.15 1 f f, OO33! 1149 "., T 11.31 j 3.90 3.95 If l ')"' / f 'j He! 1398! F ± 2 ¯ 30 1f 185 '1 - 1! ;

   i 2oō2oa / o, o5 '7'7.0'7 t! 77.59! 11.13 .z, 5o i 3 '60 bzz

  <Desc / Clms Page number 260>

 
 EMI260.1
 1399! / Î N ± J'3 29 185! - i) 201-2 9 / O, 06j Ù 77.07; 77.25. ll.u! 11.00! :;, 60 3.43 1400 if "\ OC1L 33 185 i VC.C6 '! 77.07: 77.28 11.13! 1 10, D7 1 3.60 Il!' = T ??? 77) 3 ) '?) 3.60 3, .59 .4Oi un¯ 2 33 185 J - f 201-2O9 / 0.05 t. 77, .76: 77.60 11.24 10.94 3.47 3.04 1402 1 BE2 3O 185 O.-21 i 20X-2lù / G; Q6 77.36 77.54; 10.24 11.02 3.47 1 d! 3 30! ,, 1 d! 1403 NE2 185? 7955 11.24 11, 02 3.47 3.29 1403 "lJ- '5 He! . 1B5 3-210.07! '77.36 77.55) 11.24! 1 3.47! 3 29 1404- < <-? 32 185 - 193-2LO / 0.05>) 1? 10.61 $ 10 41 3171 3956! 1 1 1405 j> j W ± -Cl 1 Î 31 185! i /? 3, 10 1 l 73, .70 1/10, 16/00, OV 3, 55:;,:; 0

  <Desc / Clms Page number 261>

 
 EMI261.1
 1.! '' ***, k i t z.¯. ! ! } ¯.¯.



  ! ! 1406 4g3 t 30 i 185 1 - f Z9s - 2o710,45 70,25 70,52! 9,% 8.98! 3.27 3.04 1 j "1, jfi NH / '1S5! 201-211 / 0.07! # 3.27 3.03; 14o7, m% i Z. Zci-a1 / o, 07; 1:' g, 36 1 '= 5.1 ± j 3.27 - --- z - j, 1 i /. É ji /, "!!! j; . t! 1408 'r <tt cF. 42! 1S5 2C7-? Ll.C, C5) 73.51 73.S9! 10.30 10.03; "3.15 j 10 08 1 I32 ':! T î ±, 3' - 1 Lc7-31" t, # 5. to: s J- î 73, & 9 j ¯ l i ''! 4 bzz 5,% 5 3.15 ...

   C j 1 i 'j' 'ji 1409 t Im2 CJ..1 38 185 éCV- "YI-O.04' 3.; 1 73.80; 10.30 j ..C, 17! 3.43 3, 11 link -; -., P - t "1 zco-J> n; o.ov ''>" 5.si ''? 3, ao; iG, 3o; (; c, 17 j 13 180 'riz8 1410 . 1 1 C 40 180 - 203-2.13 / 0O4 bO90 8J.15 11, S8:! L: 59 :), 37 3, J.6 gas Î) µ Î [) 1) 1411 N3 - / "- CH 185 : 210-223 / 0.03 80.15% 0.46: 11.49 11.10; 3.90 3.65] / Ul 1 1IB2D- OB:! f Í 39 j "1 185: - i tif 210-223 / 0.031 so> 15 '80.46 ii -, 49' 1.10 j, 90 3, 65" 'no 1 j 1412 1 .Q 40! 185 - J "207-217 / 0.061 80t15 80.35 11.49 11.31. 3.90 3.741 f b t +!,, J)., J i t go

  <Desc / Clms Page number 262>

 
 EMI262.1
 i 1413 B / -i 185; '- 200-210 / 0.05: 73.27 i t 76.44 12.84:) i 12.63'! '4.15; j, 4.07 = 1413 .JI 60 185 f 200-210 / 0.05: 78.21 78.44! 12.84! 12.63 4.115 1 4.01 * #! , i i 1414 Btt) It! 60 l, 200 II t i 200-213 / 0.05; l, i:

   78.56 i i - i 78.72 12.90 12.74 3'5311 l, 3.82 Iii i! 1415)), j 200 -: 199-209 / 0.051? 8, U4 79.05 12.56 12.81 z, 65! 3.71 # é [1416 BN / # 200! '203-215 / 0.05! {! 74.73 74.93 12.26 1 3.C5 1416 BNJ 60 200 'i 2O215 / 0.05 74.73 74.93 12926 12.05! 396 C5 NEz% - ixs, 2m-a4 / 0.05; He! 5.65 1417 NR2 30 185: - 1200-214 / 0.05 60.37 B0.67 Il, 60 11.40 3.75 3t63 1418 XHOE / 32 185 80.56 j 80.74) 1 11.70 11.57 )) 3.61 3.61 1418 HEa [32 185 1201-207 / 0.04 80.95 80.74 Il, 70 11.57 3.61 3.61 C "3 Il! J 1419% EC 33 2O0 203 -211 / 0.05 81914 81.48 11935 11.25 3.51 3.53 1419 CH {) 1200: - t 01.48 Il, 35 11.25 3.51: 3.56 ce5 m.-. , -, -

  <Desc / Clms Page number 263>

 
 EMI263.1
 ± '. i: i C "3 1 µ µ; i 1) 1: 142U NH2CH2- ('30 185 -200-215 / 0.08i 80.56 i = F0.99' 11.70;

   11.53 '- 3.61 s = 3.49 1421 IQ 200, 20-7-22310.1 80.56 30.81 11.70 11.4G 3.61 3.4-4 1421! NH2 EC 25 200! 207-223 / 0.1 - 80.56! 80.81: / 11.1? O 11.46; 3.61; 3.44 j 1422! NH2CH2 --- OH 25 z - .205-213 / 0.08! '7'7.07 7-7.24 11.13! 11.02; t 3.60; 3.43 1422) HO \ =. / 185 / 2O> 2l3 /, 0àÎ 7?, 07 ??, 24 il, 13 11.02 3.60 3.43 1423! NHp # p-i no 185 J206-223 / 0.07 '77.07 7727! 11.13 10.96 3.60, 3.25! i 142j "2% 25 185 205-l23 / tJ, O? '- i 77 ,? ¯ ??>?) i 11.13 1 10.96 3.610 3.25 <\ == a / 'CH t 1424 f 1H2CH2. 'GH30 28,190 {203-222 / 0.05' i ± '7? S3 i 77.52 11.24f; 11., 01 3, '% i 3.3'J 1 <z5 NEz0E5 28 J 1190 1! 207-219 / 0.07 'f; ?, 36 F? J, 's 11sc4 11.04. t;

   3, i''J '?> 28 1426 j j "zCizFz5 / 1 3" /? 1? ]. / (1, il) 80.41 13.22 13.10 3.11 3.06

  <Desc / Clms Page number 264>

 
 EMI264.1
 - ------ - -..-, - ------------------ ------------------ -------------- ------------ 1! 1427 J MLJ: A 30 185 1 j - = 2zs-22a / o, os t; . ' 00.51 80.78: 12.3i: 12> a0 'i 3.35, 1 - \ 5J, j j I! Î '/ 1 Ii 1 !! 1 i f J. 428 1.

   EH 60! 200 1 -; 210.¯ 220,, 04! 1 no, "7! OJ, 6:;:] 2,:; 1 J.:;, 18:;, J.:;:;, 02;! I 80.63 12,, 83 x 3902 ----. -..... --- ...-. ¯ ..-. ¯ --... ¯ .--. ¯¯.¯ --- .. ¯.¯.¯ ---- .. ..¯¯ ... ¯ ..---. ¯ - .. w --.-. ,, .¯. ¯ ----

  <Desc / Clms Page number 265>

   Example 1429
For 30 hours, 114000, a mixture of 10 g were stirred
 EMI265.1
 methanol eootearate and 5 g cyolohexylaminet by removing methanol from the reaction system. 10 reaction mixture was distilled to give 12.1 g of a desired product.
 EMI265.2
 a z'vEe of 200.20; 0/0, 'mm of Hg.



  Elementary analysis!
 EMI265.3
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 78.84 <SEP> 79.12
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 12.9G <SEP> 12.61
 <tb>
 <tb>
 <tb> N <SEP> CI.) <SEP> 3.83 <SEP> 3.70
 <tb>
 Example 1430
To a mixture of 10 g of methyl isostearate and 2 g of isopropylamine was added a solution of 0.5 g of sodium in 5 ml of anhydrous methanol and the mixture was reacted in an autoclave at 140 0 for 2 hours. Into the reaction mixture, 100 ml of ether was charged and the mixture washed with water, 5% aqueous hydrochloric acid and water, followed by the mixture. dried, concentrated and distilled, to obtain
9.9 g of a desired product with a P.E. of 185-199 C / 0.02 mm Hg.



   Elemental analysis:
 EMI265.4
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 77.48 <SEP> 77.64
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 13.32. <SEP> 13, lO
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 4.30 <SEP> 4.19
 <tb>
 Example 1431
For 3 hours, a mixture of 10 g of methyl isostearate, 2 g of allylamine and 0.5 g of powdered sodium methylate was stirred in an autoclave at 150 ° 0.

   The mixture was treated in the same manner as in Example 1430, to obtain 9.3 g.

  <Desc / Clms Page number 266>

 
 EMI266.1
 of a desire product 'of a 3? .E. from 191-19? / GO mm of ES, Elemental analysis:
 EMI266.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> o <SEP> (%) <SEP> 7795 <SEP> 77.69
 <tb> H <SEP> (%) <SEP> 12.77 <SEP> 12.49
 <tb>
 <tb> N <SEP> (%) <SEP> 4.33 <SEP> 4.41
 <tb>
 Example 1432
While stirring;, for 5 hours, it was heated to 180 C,
 EMI266.3
 a mixture of 10 g of ethyl estoBearato, 6 g of 0-methylbenzylamino and 1 g of potassium t.butyrate. Immediately after heating, the mixture was distilled to obtain 11.8 g of a desired product with a MW of 205-208 C / 0.1 mm Hg.



  * Elemental analysis:
 EMI266.4
  <! o'i 9.'l1 Anal.yt, -ue
 EMI266.5
 
 <tb> C <SEP> (%) <SEP> 80.56 <SEP> 80.81
 <tb>
 <tb> H <SEP> (%) <SEP> 11 <SEP>, <SEP>? C <SEP> 11.38
 <tb>
 <tb> N <SEP> (7) <SEP> 3.61 <SEP> 3.31
 <tb>
   Example 1435
While stirring in an autoclave for 8 hours, a mixture of 10 g of methyl isostearate was heated to 220 ° C. and
 EMI266.6
 of 5 g of p-mdthoy-oyc: lohexylamlno, to obtain 10.4 g of a desired product of a P.E. of 204-211 C / 0.05 mm of Hg.



  Elemental analysis:
 EMI266.7
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 75.09 <SEP> 76.10
 <tb>
 <tb> H <SEP> (%) <SEP> 12.48 <SEP> 12.27
 <tb>
 <tb> N <SEP> (%) <SEP> 3.54 <SEP> 3.29
 <tb>
 Example 1434
While stirring, for 48 hours, heated) at 150 C, a mixture of 10 g of methyl isostearate, 6 g of cyclohep-

  <Desc / Clms Page number 267>

 
 EMI267.1
 tylamine and 0.5 g of eodiun methYlata, removing the methanol. Then, we carried out the menas treatments as those described at 1 xemvla 1430, for> oban3. a desired product of 9.Z, do 206-210DO / 0.09 ml Hg.



  Elemental analysis:
 EMI267.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 79.09 <SEP> 79.33
 <tb> H <SEP> (%) <SEP> 13.01 <SEP> 12.84
 <tb>
 <tb> N <SEP> (%) <SEP> 3.69 <SEP> 3.35
 <tb>
   Example, .lE-.3.2
 EMI267.3
 At a m3: ur.c <19 J 0 g of i6:) a; Ó ± 11 "'at (-J of raethy7.o and 5 g of o-tolu1è1.: 1.nG, an aulubioa of 16 sodium was added in 10 ni of uethaiiol, 1.: Iiwàno and .Un a uS;:!. T; é 1o mixed at 150 C for 6 r3urfm, ea n.itxlncr.t lo mstimroi. The same treatments were carried out as those described Example 1430, to obtain a desired product of P, E, do 24-: 12 / 0.07 µm Hg.



  Elemental analysis:
 EMI267.4
 rlt9. ±. 4.;., .. 't1. gu
 EMI267.5
 
 <tb> C <SEP> (%) <SEP> 80.37 <SEP> 80.57
 <tb>
 <tb> H <SEP> (%) <SEP> 11.60 <SEP> 11.29
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.75 <SEP> 3.50
 <tb>
   Example 1436 Has a mixture of 10 g of methyl isostearate and
 EMI267.6
 5 g of 2-ahloro G-et, yl-anilina was added a suspension of 1 g of sodium methoxide in 5 ml of benzene and the mixture was stirred at 85 C for 10 hours. The same treatments as those described were carried out! Example 1430, to obtain 12.1 g of a desired product with a m.p. of 209-215 C / 0.06 mm Hg.

  <Desc / Clms Page number 268>

 



  Elemental analysis:
 EMI268.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 73.61 <SEP> 73.88
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 10.30 <SEP> 10.14
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.43 <SEP> 3.16
 <tb>
 Example 1437
For 26 hours, a mixture of 10 g was stirred at 180 ° C.
 EMI268.2
 methyl isostexate and 10 g of dodOoyl.m: 1ne. The reaction product was treated in the same manner as in Example 1430, to obtain a desired product. , Elemental analysis-.
 EMI268.3
 
 <tb>



  Theorize <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 80.11 <SEP> 80.41
 <tb>
 <tb> H <SEP> (%) <SEP> ' <SEP> 13.22 <SEP> 12.89
 <tb>
 <tb> N <SEP> (%) <SEP> 3.11 <SEP> 3.01
 <tb>
 
Examples 1438 to 1476 are shown in the following table

  <Desc / Clms Page number 269>

 
 EMI269.1
 Mcemlei .4nt 'Tenp- D = ée! People, of 'erature Duration,: P.E. C% H $ 6 N% Exem! Anine of erasure! of the! Sol- Auto- P.B. ¯¯¯¯¯ ple Imine: r reactiou vant: key 'C / un z ¯ z¯..¯ o f éf6-! µ-u? i! clave 1 IC / rm Hg Theo-! ï7-: - Theo: ..-: -. ly ': Th¯a; yreniez tison (OC)! (hours) !! ; tick tick; fricic tick risk! !: i j. l''U "'143ED; Z7' 3 = 1433 1 200 18 '- s used 185-15.IOsC4-; 77.10 ?? e4'I 13.27 1.3.00, 4 w! 4, y 143ûl, .

   CH 3 189-1S4 / 0.04! 77.10 77.41 13.27 .13.00: & 4.50 4.31 t ± 'OE (OE2C "= C" 2) 2 1433 200 la Used l-5-20110.06' 7c ,,, 12.47 12.00, 3.55 1435 m: I (CH =) 2: 1433: -, 200; Uti1i:; é: lS5-201 / 0.06 79.27 79.59! !! 12.47 12.09 3, C5 3.55 i 1433! -! 200! i - '. 'Utili'ic: .5-201 / 0.06; : 79.27 73.59! 12.09 3, S5 3.55 1/2 1433 -; 200; i - ixJti.Ls ± '¯ LüC-20-JO, O? ? 8.56 78.78 f 12.62 3.98 3.78 1440 1433 200 User: lsed: 200-2 </ 0.07J! '78, 56 78178 12.90,. 12.62 3.98 3178 thread; - '# - f: 144-LiZH2 ± 143.434 a NaOCH3 s 150 F; - ¯; 202-208 / 0.05! 79.09? 93a 13, Ol 12.8? 3.69 i 3¯; s. fil fI: Lez -1: fIl il ..: L442ïnXS '1434 Na0CH3Î 150 6 f 200-211 / 0.0 75.89 75.99 12.48 12.29 3.54 :) i,! ..



  1443 1! He! z ', 0 1 3.42 3.19 L443! J "' \ 1'ICzR.5 1434 iNaOCH3t ¯ 6 1 1 - 203-213 / 0.05j 76.22 76.56 12.55 12.31 3, 42 f

  <Desc / Clms Page number 270>

 
 EMI270.1
 $ OE, 5. 1 1 j r # -T-- Jm - LcE-! 1433 zoo 10 Used; 205-215 / 0.05 0 i 'l ""; i sO, its 81.20; ii, s6 11.65; )] / s, 57 3.17 3 i, 1 i t 1 xH ± ± -oH 1429! - 160 30 - - 205-214 / 0, O4Î i:! ÓO, 15! 80.42 J 11.45 11.19 1 1 3, SQ 1 3.65 f 1 N% -c5- j. 1 1429 160 30 '204; -214/01 It! 1 1 CH3 i 1429) - t 160! -! 214/0 s 73.61. ! 7..90 10.30 10.05 j 3.333 iCI 1 j 1 bzz9 i 1 '' Î 1 'é j Î'];

     '' '1 /' == / "'': j, '47NH .-- F' 429 Î / 140 60 - - '1: 8-206 / 0.04;? S, 39; 76.66 10, 61 j ¯ / 5 3, li 3'7 (àÔ µ 47 i 1 1 1 1 0 "i J .. :::; j 'i, t OOOO, -0- 1429 - 140 58 - i - iac.2 -216 / c, 1 70.50 j 9.36; 9.18 3> 2? Ji '\ == / il il O O't'O * OCR Il !!% O * O / -9 JllB2Ô 04> NaOMe 150 - 1 -: 2OB-2J.lJ- / 0. 04; 77,07 77 .19 11,13 11,05 z. 631 2 \ c = /> OJ11B2 -0- l '1lez 11'! Arolle. 1 1.50 200- 206 / 0.041 1 "1 77.07! 77.2! 11, U! N'541 .60 3.21 '3 1434 NaOMe 150 Î" 200-206 '77 23 11.13! "' ') 32 60 bzz 2 \ = s / 1434 INaoUe 150 IWI.JI! 200-206 / 0.041 77 * 07 11.13 1

  <Desc / Clms Page number 271>

 
 EMI271.1
 51. 't7C 1 1432,' '1 1 1 8; - t - f200-209 / 004f 77.36: 71.59 11.24 IL, 04 ¯. i 3.47;

   } 3.34 \ a,} Ii,! tif. 10 -! 'Used 2C4-209 / 0.04J' '77,%! ! i 77.58 '! '11.24 11.60! ! 3.47 <! ! 3.21 52i 5Hz 0Cj '1431 i 1 Na0Me 20O lO) -. 1/1 1 1 / used 2oeuf-209/0 '/ tu 56 58 52i IUL OC \: 1431! 1! . NaOYe! 200 J.O l !; Used; 204-209 / 0.04Í? 736 77.5 ± 3! He, 24! He, 60! 3.47 ';, 21 i' 1] j '1' f i j 1 1, 0, ¯; j '' i 1 j '1! ; 1 'i! 53,. rot CJ 1431 NaOEt 200 10 - 'i Used::.? Gê07 / 0.06; ;: 78.27:? 8.59 12.34 j 12.53! i 4.15 j i 4.00! \ ¯t 31: NaOEt 200: Used '? CO-207 / 0.06! 78.27 78.59 12.84 12.53 4.15 4.00 d [; j 1 'j>' 54 HN 1 i 1431 jNa0Et 1. 200: f 10 1 f z t # UtiJis4µ2oo-X6 / O, 061; ! 200-206 / 0.061 t 78.56 73.39 12.90 13.06; 1 3.9s! 4.05 If. ! 1 1 d ....



  / ## \ .i '' swH- l'55! m (); 1431 lKOtB-. 1,200 00 / '- used ± 20-213lO; O5 74.73 f 74.9! 'le, 26 1 12.01! z f 33 & "gp 7 i 431)> K0tBU l 20 1 i i i - 1 1 i) j Î t 78> S + 7S, 08 j 1 12.96 12> 70 '1 ... ..



  .56j 7.) 1431 jKOtBn. 200 used J206-211 / 0.07 7S, C4 79.08 12.96! 12.70 3.83 3 "56 ml 7 1431 KOtBu 200 ïused! 206-21l / 0.071? 13, C4! 79.08 12.96: 1270 3., 83 7, -e!;.



  * t j 1] j 1; ) 57.! '! NH # - / - \ 1435 '! Na0And 180! 8 MeOH} i t - 2Ol-205 / 0.05 '' C0.37 80.66! 11.60! ! 11.27 3.75 3.65 J Y <1 "é j 1 '1 O 1 1' 1 '1' j

  <Desc / Clms Page number 272>

 
 EMI272.1
 1458NH-CH - / * 1429 1 180 32 201-205 / 0.04i 80.56 11.70 11-53! 3.47 1% 58 / Àflz-lô M29 - 180 32 201-205 / 0.04 / 60.56 j 80.9C! / 11,? 0 / 11.53 3.61! 3.47 iCO5 It! 14591! 1432 1 K01: Bu 180 - 2030.05 IIi 81.14 ai, 51 / n, 55! 10, o, 51 3.31 IIi 1 1 J 1211-21B / O, 04) '77.07 77.16 11.13 11.02 3.60 3.48 HO' #ak 1429 77.07 77.16 Il, 13 11.02! 3.60 3.48 14611 NR2 14.29 180 1461! -O 1 IIi, HO 180: t J 20! -,. j j - 217 / 0.04;

   77.07 d 77.26 Il'13111'02! 1 11.02! 3.60! 3 50: / 11 "iil /) thread! J! Iiiii 'xiii> iii / J 1 xiii' iii ooe 62: MLXL '142i 1 Iii 77.3ex 77.67 11.09 3.47 142: -. 1180 77.67 Il, 24 Il, 09 3.47 W * W <ij 463, 'NH2OE2- (1429 180 205-213 / 0 C) 41 77.36 771.74 11.24 11 $ 08 463 # 2J \\ nCH! 1429 180 20 i - 1'205-213 / 0.041 77.36! 77,74, Il'2411 "') 347" -T "' .." oca3 He! ! f64; #; o 1430 j - 1 j 200 1 1 20 1 1 - 1 User1Sel204-209 / 0, 04,! 7M6 77.62 11.24 11.12! / 3 '47, 19, ¯¯¯! ! t

  <Desc / Clms Page number 273>

 
 EMI273.1
 1465'NCB! z! 1434 180/1: 809.56 C0.78 11.70 11.54 Î 3 61 3958 l.NB # y t! '- ** .3} 1434 NaOMe! 180; 5 <) - '203-217 / 0.1 G0.56! {CO.Sl! 11.70; 11.54 3.61 3.51 lLk661 NI'2% 1434 180 Iii 1 -21? / Ots 80.56 '' "d (" 2 "2 l 1 <; 'zoo-? 0W' '/' ''! 1467 iodine2 144 NaOMe '100 1205-212 / 0.0 5 80 56 00.60;

   11.70 03. 3.61 3v6O L467CIL, -yCH, i! --z - z! 1434 1M NaOHe) 205-212 / 0.05. 80.80 d s! 11.70: 11.61 3.61 3.60 'xz> -0E5 1431 l' 200 1 Used J201-206 / 0.06 <'75, C9J 76.06 12. 12.09 3.54 3.41 L468 WE2 1431 200 i 201-206 / 0, p: '76, 06! i l 1 z5) W, 82! . *): "-" i 'L469- 1429 1SO 70.82 3.27 3 & 0 L469! i -Q CF 1429 180 1 1207-220 / 0.07j j 70 70.82! 9.36 9.04! 1 3.7: 1 3rA! 1429 3.5 i t i. > .6) 9185 3.55 37. * î A70I # LHfS-cl 1429 180 201-207 / 0.06: '73 .18 73.89 10.16 9, C5 3.55 lj, i, 3 '47liNBL, y-Cl 1429 - 100 I 35 - 200-203 / 0.06 73.91 10.30 9.94 3.43 3.18 1429 100 00-20c, '/ 0.061 73.61! !

  <Desc / Clms Page number 274>

 
 EMI274.1
 110 t. the! NHCH wire 200 Used 209-215 / 0.06! 77.07 i 77.21 J 11.13 10.57! 3.60 j 3930 f72CH2 ,, 1433 200; Used209-215 / 0.06i 77.071 71.21 11.13 10.9713.601 ', 30: zC <zb, / '..33 j 1 / - 2 t 1;

   l 'j ..> .. 3'6 1? 3 Nog2 - og 1433 - zozo; 33 -; Used 205-210 / 0.07J 77.07 77.25! 11.13 ZO, Ei9 bzz 3.41 2/4741 1 1 NH¯l! 1! 1i.29 f - l 18ri bzz i I! I! 1 - 1 1202-20ô / O, C6i z? 5s53 1 i 75.69 "1 f 12.41! 12.19! - Î., 6?; ', 33 475' 1 i - @ 1y.29 - 200 40 -! - 1 - i 21û-225 / 0.07: G0.51 1 Î eo, es)!! 12.31 12.06 3.35 3, L6 i 1 oµ2g '2oo UtjLI: Lséi 210-221 / 0. àtio GO, 50 1 µ E0.28 / 02.30 02.06 3.35 1 / "\ ssYY 476 <8 1431 KOtBu! 1 used 210-221i0> t76 a0> 4? , f f30.61 12, f33 12.66 3s13 ..... un .1 4761 mI 1431 1 KOtBu 220 used! 210-221 / 0.0611 00.47 f 00.61 l 12.83 12.66, 3.13 f t 1 1 1 t .... j "Yi

  <Desc / Clms Page number 275>

 Example 1477
16 g of linoleic acid were dissolved individually, 16 g
 EMI275.1
 do dioyo1ohexyl.-onr'bodiimido and, 5 g of dia-yolchoxylamine in 20 ml of benzene.

   The three solutions thus prepared were mixed together at one time and the mixed solution stirred for about 3 minutes. The mixed solution was allowed to stand at room temperature for about 10 hours, and 3 ml of acetic acid was added to the solution, then the mixture was allowed to stand at room temperature for an additional 2 hours. The precipitated dicyclohexyl urea was separated by filtration and the filtrate was washed with HCl, 5% aqueous 1, 5% aqueous NaOH and water, then dried, concentrated ot distilled, to obtain 19.2 g of a desired product of a P.

   E. of 200-209 C / 0.05 mm Hg. ND26 1.4880, Elemental analysis:
 EMI275.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.20 <SEP> 79.94
 <tb>
 <tb> H <SEP> (%) <SEP> 12.04 <SEP> 12.00
 <tb>
 <tb> N <SEP> (%) <SEP> 3.16 <SEP> 3.24
 <tb>
 
Examples 1478 to 1504 are shown in the following table:

  <Desc / Clms Page number 276>

 
 EMI276.1
 Pla- Acid P.E. Agent! #### - L #### ¯¯¯ Ù? Acid condensation Solvent C.

   Hg, Theo-. * m0y- TEeo- 1 kmoy-) TJ.éo,.: 1 ī¯¯ --- ¯ -------------------'------ ----------- ¯¯ ------- li ------------- == ¯ !! f; - = iqf 1478 Linoleic acid 0! Dioxane "---- j 1 --- 1 Olt0c. j ------) '--- 1 3 * 21 1478 Linoleic acid ± Oxane 203-210 / 0.07 81.20 / 81.09, 12 , 04 !, il, 99 3.16 3.21 1479 '0' ¯¯ 1 Pyridine! 200-208 / 0.06- 81.20 81911 12.04 i ii, So 3.16 3.19 1 1400 "-! : Chloro- ÎZ02-209 / O * O6i 81,2O 81,07 02, OW j 12 * or 3.16 14 forrie 1480 fgo- 2O3-209 / O, 06µ 80oo z16 3> 20 1481 1 loro- 203-209 / 0 , 06! ;

   B1.20 81.0.5 12.0f4. 12.31 3.16 3.20 -fo wire r * \ tif 1482 "Toluene -" 201-209 / 0 * O6i 31.20! '1 Sl, 00) j 12, OW n, D9 3,16 3,23 Í 1483 -1-Bzo i i Dioxane! i 201-209 / 0.05 81.20 f '31.14 oz, 04 1 il, 95 3.16 3 * is 1484. -i-Pro 1 Ether 201-208 / 0.07 81.20 81.30 12.04 12.00 3.16 bzz 5 -1-BrO Boezènie 204-211 / 0.08 81.20 f 00.99 12 , 04 12.03 3016 3.19 1486 0inoléniqe ± Di "" "" "" 204-208 / 0.06 81'57181 '11.64 11.88 bzz bzz

  <Desc / Clms Page number 277>

 
 EMI277.1
 t i i 143: Linoleic acid 0 'T ± -traby- I200-212 / 0.07! 81.57 i 81.41 i 11.4 i 11.53; 3.17 1 3.06 \ # i. i 5 drot "urannei j -z-Pzo Py, rf.d3ne i c'31.5i;; iii 1438 /" -I-PZO 1! Pyr1dine t i 209-215 / 0.1; 81.57 81.4.5 11.64 n, 51 Summer 3.07 3.14 i 1489 i Oleiouo acid 0: Benzene 195-20S / 0.05 30.83 EO, L31 12.44 12.29 3.14 3.06 d 1489 "Oleitao Benzene Acid 195-20010.05. 8J, 83;

   OO, ro. ! 144 12.29 3.14 3906 0489 Ole0qyuo acid Benzene 095-200 / O, 5 '80, sol fi "3.06 1490 j Oil fatty acid; - - \ - /' Benzene Ben? An3 195-213 / 0.0? ! .9-.2'¯3! C7, G '? - - - - - 1490 aci of oil fat r- \. Bemzèn-3 19% zzµ, / y, o? 1;'. ¯ of carth .an.e J: i; j J 1491 Using oil sras ./# <. ). Toluene ':. 200-214 / 0.05 1491: cotton oil 0 Tùl1.o.ene 200-214 / (i, O; -.! -. 'T cotton Il.



  1492 to c0àe oil fat "1 Ether '330-c.lO, CS - j - - 1 - - i; of cuttlefish of oil µ i j! J j j, ...



  11493; Oil fatty acid! - 'JTêtrahy- ti 201-2i? Lü 05 - ¯: - :: 14'93'. Fatty acid from irétraby- oil: 201-217 / 0.061 ± from mackerel drofimamy t ..: 1 i ** J.94 ! Acidegrasd today! -1'1 Ether f200-209 / 0.05t - i - il - t - -; ' .



  ; of pleuronecte fi! ! .. *,; f - fil l '.... t.



  1495; oil fatty acid Ether wD 192 21% O, 06 - - - 1495 j ÉàiÉoÀlÉx / 9 (1) Ether:! ; 1, ", 14.96! Oil fatty acid i Tetrah- 199-213 / 0.06 1 f 1496 'Oil fatty acid! - Tetraby- j.' 199-213 / 0.06! - - of herring 1 dro: rurannet "a. -.-..... ---... r -. o ..r. .-r. ........ t

  <Desc / Clms Page number 278>

 
 EMI278.1
 ij '1497' "Acid 'oil glas -'; 'JToluene! 187-208 / 0.04 1497 Oil fatty acid i Toluene - 187-208 / 0.04 from liver denorue il! 1498 Fatty acid from Dioxane oil 187-209 / 0.051! of sardine 11 f!; '"fI t 3 + 99:

   Oil fatty acid - i Ether 187-211 / 0.07!
 EMI278.2
 
 <tb> 'from <SEP> liver <SEP> of <SEP> shark
 <tb> 1500'Acid <SEP> bold <SEP> of oil <SEP> Dioxane <SEP> 200-214 / 0.06
 <tb> from <SEP> liver <SEP>
 <tb> 1501.Acid <SEP> bold <SEP> of oil <SEP> Toluene <SEP> 205-216 / 0.0 @ <SEP> - <SEP> residual
 <tb>
 
 EMI278.3
 1502 Imile fatty acid - - ± Ether 200-209 / 0.07 - - j - - - 1
 EMI278.4
 
 <tb> @ <SEP>! <SEP>! <SEP> of <SEP> whale <SEP> @
 <tb> 1503 <SEP>;

  Acid <SEP> bold <SEP> of oil <SEP> Chloro- <SEP> 185-211 / 0.06 <SEP> - <SEP> - <SEP> -
 <tb> 1 <SEP> 1 <SEP> 1 <SEP> of <SEP> will know! <SEP> shape <SEP> @ <SEP> @
 <tb> 1504 <SEP> Acid <SEP> bold <SEP> of oil <SEP> - " <SEP> Ether <SEP> 195-209 / 0.07 <SEP> - <SEP> - <SEP> - <SEP> - <SEP> - <SEP> -
 <tb>
 
 EMI278.5
 d $ .âs8 fI- 3 ¯¯j¯¯¯¯¯¯'¯¯¯¯¯¯¯¯! ¯¯¯! ¯¯¯¯i '' '

  <Desc / Clms Page number 279>

 Example 1505
For 8 hours, using a water separator, a solution of 16 g of linoleic acid, 9.5 g of
 EMI279.1
 dicyclohexylamine and 013 g of p-toluene-eultonic acid in 100 ml of toluene.

   The reaction product was washed with 5% aqueous NaOH, 5% aqueous HCl and water, then dried and concentrated, and the residue was distilled, to give 18.6 g. of a desired product of PE 205-208 C / 0.06 mm Hg. nD25 1.4882.



  Elemental analysis:
 EMI279.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%), <SEP> IF, 20 <SEP> 79.99
 <tb>
 <tb> H <SEP> (%) <SEP> 12.04 <SEP> 11.95
 <tb>
 <tb> N <SEP> (%) <SEP> 3.16 <SEP> 3.31
 <tb>
 
Examples 1506 to 1530 are listed in the following table in which: Catalyst!
A. p-Toluenesulfonic acid
B. p-Toluenesulfonic acid chloride
C. Sulfuric acid
D. Phenol-sulfonic acid
E. "IRA-400",
F. "Amberlite-15" Solvent: a. Toluene b. Pyridine c. Bonzèno d. Chloroform e. Xylene f.

   Carbon tetrachloride

  <Desc / Clms Page number 280>

 
 EMI280.1
 ; Ebcec # 'Duration':. "** # ..., ##" #: ########### ple Catacid acid of PB - ###### 'Ca "ta-!"' of C $ liiHg iÉé '' 1 .1cide lyseur Solvan1 ;, rl! actionl Theo- Theo- '(hours)'; tick "tick! tick! tick; tick tick"; ri9uej tick! : 1.506 Acid 016iqoe / to to a to 8 204-210 / 0.06: 00.83 00.71 12e44 12.39! 3.14; 3.09 1507! c 8 2O6-210 / 0.06 SO, C3 80.69 f 12, "" - / 13.33 3; 14) 3.08 1508 200-2C9 / 0.06 / 50.85) Il! ! 1508 i. 'j --2C9 / 0, C6 vo, n 00.45 12.44 12.31! 3,14, 15 1509 idelinolêiqae 'A' n! onr, - r.



  He! ! 1509 f1.cid c.nolic ja fi 203 -207 / 0.05 n 1'w Gl, 56 12 04/12 Ol z 16 3.3: 1510 j 1. B b 20 202-207 / 0.05 & 1, zo 1 si, 45 j 12, <: 4 g 11, e7 j 3.16) 3.45 1513 (1 * C ia 8 "Ô 2j5-20? / Il 06 81.20. Gl 09 j 12 &% 11.95 3.16 3.09 1512 'Dia!' "10," 1. 2Oit - 209 / 0.06jlJl, 2O; ci 04 12.04 i 11.98 3.16 1 3.00 J 1 1513 z 204-209 / 0.06 81 , 20 81.29 12.04 11 4.16 3.4 1514 10 1 i 200-210 / 0.06 81, 2D 81.09 1 - 3 11514 1 "A) 10 200-210 / 0.06 81, 20 81.09 12.04! n, 69 3.16 3 19 '115151' L1nolenic acid 8 206-2, Dg / 0 $ 06 81.571 ei.69} 11.64 U.45 3717 3.. * 1 1 1516 1 1 m 204-210 / 0.07! 1 Bls57 81,5o 17 3909! 1516 1. A! j 8. ) 204-2MA..07 [81 57 '81.50 11.64 11.39 3.17 3, oo 1517 b Î 20 203-207 / 0 01.57 61.47 11.64 11.58 3.17 3.15 1 1517 1 "203-20'110.06 81.5'1 81.47 11.64-! 1: L, 53 3.1'7 3 15 '

  <Desc / Clms Page number 281>

 
 EMI281.1
 - ..

   F * '' '#! ###: ##' ** 7 * ##: ###: ###### ¯ safflower 1519; :, Zcide oil 198-2IOj0 06 -. ¯ safflower j 198-210 / 0.06 j - -)! ¯ 1520 -Oil acid of f 15. 196-209 / 0 06 '- J - i f 1520 sesame oil 196-209 / 0.06: - j - i - i; ! . Sesane;!:!; !! 1: 1: T '- 1521 Oil acid of B c l3 191-211 / 0.05 -! - - "- 1522 C F F a # 12 oil cide 155-214 / 0.06 - -1 -, - 'ihe": T! '! 192-213 / 0.05! i f 1523 Oil acid from e 12 192-213 / 0105 -! -: - 'mackerel 1524 .1 .. oil acid of E i e 10 195-209 / 0.06 - - - J t .; .



  4pleuronecte t 1 1525 'with oil acid .ti 1'90-214 / 0.06 f scozibrésoce 1 -'.



  1526::. Oil quantity of: 192-215 / 0.06 - J ¯ t 1527 - ro ie de morne b i i j ID 188-216 / 0.05 - f - f t - f i 1 - - j - f.



  ± 01st Darne fI ".



  1528 oil cide ae 189-209 / 0.04. ). sardine 18 189-209 / 0.04 - f - i r. :: sardine b 15 18'7-216 / 0 $ 06 r- :.



  {shark liver 15 .LU7- <-16 / 0.06 -! - f - J - f - ò1e da shark if! 1530 Dllnil acid from 11 to 20 169-217 / 0.061 - i - whale iag-2zfo, bone. - 1 ::. :: - ###### L ''; f i i ..

  <Desc / Clms Page number 282>

 



  Example 1531
 EMI282.1
 For 20 hewrox, we ch1fé. At 10 0, a mixture of 16 g of lnolic acid and 9.5% of di.cya3 rhelamine. The product of In: actiol1 was immediately distilled. to obtain 18.0 g of a desired product having an M.F. of: b211 C / 0.04 nun of; nD28 1.4880.



  Elemental analysis:
 EMI282.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> IF, 20 <SEP> 80.99
 <tb> H <SEP> (%) <SEP> 12.04 <SEP> 11.98
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.16 <SEP> 3.14
 <tb>
 Example 1532
For 100 hours, a mixture was reacted at 200 ° C.
 EMI282.3
 of 16 g of linolbata do a6ti4y] e n4.0 @ 4a 13 g of dioyclohexylamine then the aGtrnc1 of the 3rd of the reaction was removed by distillation.

   The reaction product was dislocated to yield 12.0 g of a desired product with a PE of 205-213 0 / 0.05 mm Hg; nD28 1.4875, Elemental analysis:
 EMI282.4
 
 <tb> Theorise <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.20 <SEP> 80.97
 <tb>
 <tb> he <SEP> (1.0 ' <SEP> 12.04. <SEP> 12.00
 <tb>
 <tb> N <SEP> (%) <SEP> 3.16 <SEP> 3.08
 <tb>
   Example 1533
To a solution of 14 g of linoleic acid and 5.5 g of triethylamine in 100 cm3 of t6trahydrofuran was added dropwise 5.9 g of echyl chloroformate, while stirring at a temperature between -10 and -5 ° C. Stirring was continued at -5 ° C. for a further 20 minutes and then, while stirring at -5 ° C., 9.5 g of dicyclohexylamine was added dropwise.

   The processing was carried out in the same way

  <Desc / Clms Page number 283>

 than in example 397. Well! 16.2 g. M.p. 204-213 C / 0.02 mm Hg; nD23 1.4888.



  Elemental analysis,
 EMI283.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.20 <SEP> 80.98
 <tb>
 <tb> H <SEP> (%) <SEP> 12.04 <SEP> 11.98
 <tb>
 <tb> N <SEP> (%) <SEP> 3.16 <SEP> 3.18
 <tb>
 
Examples 1534 to 1548 were carried out in accordance with Examples 1531, 1532 and 1533; they are listed in the following table:

  <Desc / Clms Page number 284>

 
 EMI284.1
 'Exē Acid 1' c ¯jnr "NO C / CI: 1 Hg Theo-, 1 alY-1 Theo-. L.naly-1 Theo-; Ana1y-! ##### ¯¯¯ #### ####### ¯¯¯¯¯ tick tick tick tick tick 1534 Oleic acid 200-209 / 0.06 J 80.83 80.75 '12' 44 f 1.2.34! 3.14 3 l8! ¯ 1535: 1ino1enic acid f! 206-209 / 0.06 Í i 81.57: & 81 '6?] I 11' E4 ll '4S' 3.17 3 '' j O "1536" i Oil acid of carthane. lS5-206 / O '' C6 Î 1.



  1537. Cottonseed oil acid! 198-218 / 0.06 - - 1530 sesame oil acid Î 196-207 / O, Q6 - µ - - - 1539 (acida d'i; castor oil mill 191-2141e, 05 1 - 1 - 1540 1-Oil of cuttlefish f. 191-214 / 0.05! -: ¯ ¯; 1540 Acid of cuttlefish oil 192-215 / 005 -! -! - 1541 of oil -; - of mackerel 1541 1 naquereau oil acid) 192 215'O 'G5 1542 i Pleuronect oil acid 195-208 / 0.06 tif 1542 j {Pleuronect oil acid) 196-214 / 0.06 1543 sconbrésoce oil filcid f, 1.96-214 / 0.06 154}! Acid from sconbrésoce oil (196-214 / O, 06 f - '¯ 1544 lAeïde herring oil 1192 218 / 0.06 il;!;

   , 1 1545! Herring oil acid 188-215 / 0.05 /! j 1546 i Liver oil acid 189-203 / 0.04 1546 s Liver oil acid 189 208 / 0.04 1547 1 Liver oil acid 189-2OIV0.0 '> -. -! - - 154? i Liver oil acid lB? -2l5 / O C6 154 ± 3 the ide of whale oil '/ 189-2l9 / O, 06 -

  <Desc / Clms Page number 285>

 Example 1549
While stirring at 0 - 5 ° C, to a mixture of 9.3 g of dicyclohexylamine, 100 ml of anhydrous ether and 4 g of trimethylanino, a solution of 16 g of chlorura was added. linoleic acid in 20 ml of anhydrous ether. The reaction mixture was stirred at room temperature for 2 hours and allowed to stand overnight, then boiled for 2 hours.

   Then, the ether solution was washed with 5% aqueous HCl, 5% aqueous NaOH and water, then dried over anhydrous sodium sulfate, concentrated and distilled. , to obtain 17 g of a desired product of a PE of
 EMI285.1
 202-20700 / 0.06 min Ig; n5 l, 4070.



  Elementary analysis!
 EMI285.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.20 <SEP> 79.99
 <tb>
 <tb> H <SEP> (%) <SEP> 12.04 <SEP> 12.02
 <tb>
 <tb> N <SEP> (%) <SEP> 3.16 <SEP> 3.12
 <tb>
 
Examples 1550 to 1568 are shown in the following table

  <Desc / Clms Page number 286>

 
 EMI286.1
 ¯! C H% fi% Acid Chloride Igent Solvent C $ ÎÎ Eg 'Thé lùÀy-1 Iho-' Alyll Theo- 'u aems o-LvanT condensation? cC / ml Hs ni) Theo- .hr1a1y-: Theo-;

   Theo- Analy-! j rique; tick tick tick brick tick! 155O,! limluque Na cide; 1% 0-Dioxnnej 203-20r, / 0.07 i 1.4878 / 81.20 1 81 toq 12.04 12.00! 3,1.6 [3,21 'jl 1 1)' [1551 K ± C0 20> 2ÙS, '0; S71 É 1 1,4873+ 1 1 Sl, 20 t 1 1 81,14 j 1 f 12, OW 1 t 1 12.01 3.24 1.551 K2CO3: Methyl-; , 203-203 / 0.07'1.4373 01.20: 81.14 12.04 j 12.01 3.16 3.24 iisobutyl-! ! acetone; ) 1 d 1 1 ..



  1552 Excess of; Benzene! i; 2CO-é: CYJ / O, 06,! 1,4û75) 81.20 81.13! 12 c4 j µ 12.00 '3.16 3.28 fNH,. <8%; t. ". 1553 Na 2 CO 3 Acetone: 205-210 / 0.08: 1.4877 81.20, 81.10 j 12.04 12.0 .: 3.16 3 lit: -: 1553 Na03 Acetone; ' l., 4S7? j 81,2o j Ol, 10] 12, ù4 j 12.05 3.16 3 - 1554 KOH Toluéne t 1 j 81, Q9 12.0W 01 16 554 EQE Toluene 204-201 -) / 0107 '1,4-8-7iB' 81.20 81.09 12.04 12.01 3.16 3.171: r. 555 i 1: oil cide of f! 1 NaOH IO-Dioxane. 1 1 198-210 / 0,06i 1 It4û65ft - j - if "arthat1e i)

  <Desc / Clms Page number 287>

 
 EMI287.1
 3556 .: fde i lino3aic naos;> O-1; etraby-i = 204-20 <3 / Os05 1.4881 81.57 a, j ai, 39 11, & 1- i ll58: i 3.11! 3s drofurajcne dl'Oturamle fI; "1557! - 1 C03. Acetone. I -: 206-2101005 1.4383; Cl, 57 i ¯ 1.45; j 11.64!. 1.59; j 3.17. - a 3.15 1 He ".



  'i. . & '1 "' 1" .e.Cs.3e ..i zi! CR3: Benzene 1558! Oleic acid, NCH, VtT; Benzene ': 200-20C / ù, C6: 1.4874 i CO, C3 [, O, SO; 12.44: 12.38! 3.14; 3.09 j ¯ É i3 'µ 1 "" j' / 'µ j l i, 1 i j j f J f) j é j He! He! Í I "! F f 1 * 1.559 Cuttlefish oil NaOH H¯O-Dioxane '200-21" / 0.06! i 1, 4D90: - - j -! He! . ! 1 1 fi 'i i5' Oil * m * h aU a "2 1-2'6 /,") 1 tif, 0j0 $ .le IaOH He !! f j:. "- 1: 1560: Daquereau oil NaOS HpO-Dioxannei 201-216 / 0,06,1,4895 - i - -; - 1 -: - Ii f; Ir ....



  ! 1, If 1 - - ./8 .-. ! -1: Ii: -1: i. f 1561! Pleuronec'te hu11e! 1 d NaOH H2O-D.oxane 200-20 / 0.03 = 1.4fi6 - j -, - - ri {*! '{**! ! 1 j i 1 Y 1 1562tBonedescoEtb! Resoce! NaQH; : H2O-Dioxane 192-210 / 0.06'1.4893 -! - i -! 1562 i Î Blle scombrésoce j 1 NaCH j - 192-210 / 0, 6 'ï j 1.4B93 j µ. , ¯ - h Î 1 '-; i '., 1;

  <Desc / Clms Page number 288>

 
 EMI288.1
 1563 Herring oil K2CO3 Methyl- 194-211 / 0 d 1563 d Bareng oil OO: 7 Methyl1-! 194-21l / 0.01f 1. '' '000:

   -! - -! - ketone 1564 Liver oil 1 i 1 Ether t! 1 cod. Liver of \ 1 Ether) 19C-214 / 0.06! L, 4S72. ) 1 / '/' 1555 sardine eggs DD) s Toluene 200-216 / 0.05d le40831! sardiDe 1 1 Toluene j j 200-216 / 0.05j 1, = 1 - J) - j - 1 1566 liver n-N <Cil 3, 1 'ii 1 1 566 1 Hùil e of faith e àe 0'! /o.o. - - 1 - - - - 1567 shark liver 'CH3 j tformamide -.' * 1567 Liver oil NaOH d2éetr 194-220 / 0.07) 1.4869 a 1 156S Residual oil Xa0E% 0-Dioxnnei 48e9j 156G Residual oil NaOH 0-Dioxaimel93--264 / 0.071.4CS9; : I:

   *! ) '

  <Desc / Clms Page number 289>

 
 EMI289.1
 -.% = the 1569
Laying overnight. a nelango of 12 g of linoleic acid, 10 g of dicy- nelango was left to stand at room temperature.
 EMI289.2
 olohoxyl-oarbodiimido and 6 g of adamantylaNine in 40 ml of benzene, 3 ml of acetic acid was added to the mixture which was then filtered.

   The filtrate was washed with 5% aqueous hydrochloric acid, 5% aqueous sodium carbonate, and water, then dried over anhydrous sodium sulfate, then allowed to dry. concentrated and distilled, to obtain 15.3 g of a desired product with a PE of 188-190 C / 0.03 mm Hg; nD30 1.4000 (yield! 86.9%).



  Elementary analysis
 EMI289.3
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.29 <SEP> 81.56
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 11.45 <SEP> 11.90
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.39 <SEP> 3.72
 <tb>
 Example 1570
In the same manner as in Example 1569, a mixture of 12 g of stearic aoid, 10 g of diisopropylcarbodii- was treated.
 EMI289.4
 medium and 6 g of adamantylamino in 20 ml of t6trahydrofurano, to obtain 13.9 g of a desired product with a P.E. of 14F3-194 a / 0.1 mm of Ig, (Randeri6nts 79.0 5).



  Elementary analysis!
 EMI289.5
 
 <tb> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 80.51 <SEP> 80.88
 <tb>
 <tb> H <SEP> (%) <SEP> 12.31 <SEP> 11.95
 <tb>
 <tb> N <SEP> (%) <SEP> 3.35 <SEP> 3.48
 <tb>
   Example 1571
In the same manner as in Example 1569, a mixture of 12 g of oleic acid, 10 g of diphenyl-carbodiimide and 6 g of adamantylamine in 20 ml of methyl acetate was treated. for

  <Desc / Clms Page number 290>

 
 EMI290.1
 Obtain 15.1 g of a desired product of a P.E. of 1 E19 C / 303 ml Hg (Roundness: 85.8%).



  Elemental analysis,
 EMI290.2
 ± 1r.lE..q l..z: 4ktiq1, t!
 EMI290.3
 
 <tb> C <SEP> (%) <SEP> 80.91 <SEP> 80.52
 <tb>
 <tb> H <SEP> (%) <SEP> 12.31 <SEP> 12.66
 <tb>
 <tb> N <SEP> (%) <SEP> 3.35 <SEP> 3.70
 <tb>
 Example 1572
 EMI290.4
 In example, in Example 15691 a mixture of 12 g of linoleic acid, 10 g of dbenzylarbod11m1de and 6 g of adamantylanino in 40 .1 of ohlcoeofonme was treated. , to obtain 14.3 g of a desired product with a PE of 188-191 C / 0.03 ml Hg.



  Elemental analysis:
 EMI290.5
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.69 <SEP> 81.99
 <tb>
 <tb> h <SEP> (%) <SEP> He, 02 <SEP> 10.94
 <tb>
 <tb> N <SEP> (%) <SEP> 3.40 <SEP> 3.65
 <tb>
 Example 1573
In the same manner as in Example 1569, a mixture of 12 g of a mixed fatty acid obtained by hydrolysis of oil was treated.
 EMI290.6
 but, a solution of 10 g of dicyc3ohox3r..ca, rbodümide in 20 ml of benzene and a solution of 6 g of adamantylamine in 10 ml of benzene, to obtain 10.0 g of a desired product of a PE do 180-196 C / 0.03 mm Hg.



    Example 1574
In the same manner as in Example 1569, a mixture of 12 g of a mixed fatty acid obtained by hydrolysis of liver oil of moruo, a solution of 10 g of dicyclohexyl-carbodiimido in 20 ml of tetrahydrofuran in a solution of 6 g

  <Desc / Clms Page number 291>

   adamantylanino in 10 ml of tetrahydrofuran, to obtain 11.2 g of a desired product with a MW of 176-199 C / 0.03 mm Hg.



  Example 1575
Using a water separator and stirring for about 0 hours, a mixture of 10 g of acid was boiled.
 EMI291.1
 linoleic, 6 g of adanantylanino, 2 g of "IRA-400" and 50 ml of toluene. Then the avocado mixture was washed with HCl aquew. at 5%, 5% aqueous Na2CO3 and water, to obtain 4.8 g
 EMI291.2
 of a desired product of a P.E. do. E3-190 C / 0.04 mm Hg; n4 1.4092.



  Elementary analysis
 EMI291.3
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 81.29 <SEP> 81.35
 <tb>
 <tb> H <SEP> (%) <SEP> 11.45 <SEP> 11.58
 <tb>
 <tb> N <SEP> (%) <SEP> 5.39 <SEP> 3.61
 <tb>
 Example 1576 Melting for 4 hours, a mixture of 10 g of oleic acid, 6 g of adamantylamine and 3 g of p-toluenesulfonic acid chloride in 20 ml of pyridino was boiled. After removing the solvent, the mixture was washed with acid, alkali and water, then distilled, to obtain 8.0 g of a desired product with a PE of 188. -192 C / 0.03 mm Hg.



  Elemental analysis:
 EMI291.4
 
 <tb> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 00.91 <SEP> 81.21
 <tb>
 <tb> H <SEP> (%) <SEP> 12.31 <SEP> 12.09
 <tb> N <SEP> (%) <SEP> 3.35 <SEP> 3.52
 <tb>
 Example 1577
Using a water separator, a mixture of 5 g of oleic acid, 3 g of ada was boiled for 8 hours.

  <Desc / Clms Page number 292>

 
 EMI292.1
 It is mixed with a small amount of p-'tolube-w.lto1üic acid in 20 ml of toluene. The reaction product was washed with acid, alkali and water, then distilled to obtain.
 EMI292.2
 nir 4.7 g of a desired product with a MW of 100-1910010.0 mm Hg.



  Elementary analysis!
 EMI292.3
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 00.91 <SEP> 81.23
 <tb>
 <tb> E <SEP> (%) <SEP> 12.31 <SEP> 12.09
 <tb>
 <tb> N <SEP> (%) <SEP> 3.35 <SEP> 3.62
 <tb>
   Example 1578
Standing for about 1 hour, a mixture of 10 g of adamantylamine and linoleic acid was heated at 200 ° C. in a distillation flask, then distilled to obtain 6 g of a desired product of a PE of 188-192 C / 0.04 mm Hg; nD24 1.4092.



  Elementary analysis
 EMI292.4
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 01.29 <SEP> 81.31
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 11.45 <SEP> 11.67
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.39 <SEP> 3.29
 <tb>
 Example 1579
For 40 hours, while stirring, a mixture of 8 g of soybean oil and 3 g of adamantylamine was heated at 150 ° C. in a nitrogen atmosphere, then distilled to obtain 10 g of a desired product with a PE of 178-192 C / 0.03 mm Hg.



  Example 1580
 EMI292.5
 For 2 hours, a mixture of a s of 3 S oarthan oil and adamantylomine and 0.6 g of sodium methoxide was heated to 100 ° 0. The reaction mixture was dissolved in

  <Desc / Clms Page number 293>

 ether and the solution was washed with 5% aqueous HCl, 5% Na2CO3 and water, then dried and concentrated to obtain 10 g of a desired product of a PE of 180-193 C / 0.04 mm Hg.



  Example 1581
For 2 hours a solution of 8 g of cuttlefish oil, 3 g of adamantylamine and 0.8 g of potassium t-bu-toxide in 50 ml of benzene was boiled. The reaction mixture was washed with 5% aqueous HCl,%% Na2CO3 and water, then dried, concentrated and distilled to obtain 8.3 g of a desired product of a PE of 172-202 C / 0.04 mm Hg.



  Example 1582
A mixture of 10 g of linoleic anhydride, 5 g of adamantylamine and 20 ml of tetrahydrofurnano was left to stand overnight. Then, the mixture was washed with acid, alkali and water, then distilled to obtain 4.2 g of a desired product of 188-190 C PE / 0.03 mm. Hg; nD24 1.4891.



   Elemental analysis:
 EMI293.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 01.29 <SEP> 01.40
 <tb>
 <tb>
 <tb> he <SEP> (/. <SEP>;) <SEP> 11.45 <SEP> 11.59
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.39 <SEP> 3.38
 <tb>
 Example 1583
To a mixture of 6 g of adamantylamine, 6 g of potassium carbonate and 50 ml of methyl-i-butyl-ketone was added 11 g of linoleic acid chloride. The mixture was allowed to stand overnight at room temperature, then warmed with stirring at 50 ° C for 2 hours.

   Then, the reaction mixture was washed with hydrochloric acid.

  <Desc / Clms Page number 294>

 5% aqueous, 5% aqueous sodium bicarbonate and water,
 EMI294.1
 then it was dried and f'onaant.X'é qu distilled to obtain 1311 g of a product of an M. do 11X; 191 / 0.14 min of Hg; nD24 1.4892.



    . 'elemental analysis:
 EMI294.2
 .21 ': 1':! -. Q / ± µ ùfj gg ±
 EMI294.3
 
 <tb> C <SEP> (%) <SEP> 81.29 <SEP> 81.31
 <tb>
 <tb> H <SEP> (%) <SEP> 11.45 <SEP> 11.67
 <tb>
 <tb> N <SEP> (%) <SEP> 3.39 <SEP> 3.29
 <tb>
 Example 1584
At a temperature of 2-5 ° C, palmitic acid chloride (10 g) was added dropwise to a solution of 5 g of adamantylamine and 3.1 g of pyridine in 50 ml. of benzene * Then
 EMI294.4
 to 'we dealt with the u6lsngld of the 1i'. 11th way that in example: 1569, to obtain .0.5 g of a pJ'Cdui1i d.6sil'é with a P.E. of 183-186 C / 0.02 mm do Hg, Elemental analysis:

   
 EMI294.5
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 00.14 <SEP> 60.40
 <tb>
 <tb> H <SEP> (%) <SEP> 12.16 <SEP> 12.09
 <tb>
 <tb> N <SEP> (%) <SEP> 3.60 <SEP> 3.47
 <tb>
 Example 1585
Linoleic acid chloride (10 g) was added dropwise to a solution of 6 g of adamantylamine and 2 g of caustic soda in a mixture of water and dioxane. Then we have
 EMI294.6
 offact the other treatments described in Example 1369} to obtain 11.2 g of a desired product from a P.E. of 188-192 C /
0.03 mm Hg.

  <Desc / Clms Page number 295>

 



  Elemental analysis:
 EMI295.1
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 01.69 <SEP> silo?
 <tb>
 <tb> H <SEP> (%) <SEP> 11.02 <SEP> 10.81
 <tb>
 <tb> N <SEP> (%) <SEP> 3.40 <SEP> 3.51
 <tb>
 Example 1586
Oleic acid chloride (10 g) was added dropwise to a solution of 5 g of adamantylamine in 30 ml of trimethylamine.

   Then the same treatments were carried out as those described in Example 1569, to obtain 10.1 g of a product.
 EMI295.2
 d6811'6 of a P.E. do 15 13F3 C / 0.02 an do Eg * Elemental analysis:
 EMI295.3
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 80.91 <SEP> 01.05
 <tb>
 <tb> H <SEP> (%) <SEP> 12.31 <SEP> 12.19
 <tb>
 <tb> N <SEP> (%) <SEP> 3135 <SEP> 3.41
 <tb>
 Example 1587
In the same manner as in Example 1569, to 10 g of safflower oil fatty acid chloride was added 5 g of adamantylamine, to obtain 9.8 g of a desired product of 'a PE of 180-194 C / 0.04 mm Hg.



  Example 1588
In the same manner as in Example 1569, 10 g of sardine oil fatty acid chloride was added to 5 g of adamantylamine to obtain 9.3 g of a desired product of. a PE of 164-208 C / 0.05 mm do Hg.



  Example 1589
For 40 hours, a mixture of 10 g of t-butylo linoleate and 10 g was stirred in a nitrogen atmosphere at 150 ° C.
 EMI295.4
 dtu: 1an1i11amno, then the mixture was distilled to obtain

  <Desc / Clms Page number 296>

 
 EMI296.1
 13.0 g of a desired product of a P.E. of 1t35-lt3G G% OG2 or Xg; nfiO 1,4GG9 (rondonont: s t3 ti $).



  Elemental analysis:
 EMI296.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 01.29 <SEP> 01.55
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 11.45 <SEP> 11.71
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.39 <SEP> 3.69
 <tb>
 Example 1590
With stirring, for 1 hour, a mixture of 10 g of methyl linoleum of 5.5 g of adamantylamine and 2 g of sodium methylato was heated to 100 ° C., then the mixture was removed.
 EMI296.3
 thanol of the ayoteme of the reaction by dietl11ntion.

   The reaction product was dissolved in ether and the ether layer was washed with water, then dried, concontréo and distilled, to give 13.0. g of a desired product with a PE of
 EMI296.4
 1CO-1Q9 C / 0.03 cm H; Il 32 1 4884. (Yield: C, F3), Anc.l80 élôm (; lp / .; c.il "d:
 EMI296.5
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> C <SEP> (%) <SEP> 01.29 <SEP> 01.09
 <tb>
 <tb> H <SEP> (%) <SEP> 11.45 <SEP> 11.59
 <tb>
 <tb> N <SEP> (%) <SEP> 3.39 <SEP> 3.48
 <tb>
 Example 1591
While stirring, for about 50 hours, a mixture of 10 g of methyl oleate and 6 g of adamantylamine was heated to 140 ° C., then the mixture was distilled to obtain a product. desired PE of 188-192 C / 0.03 nm of Hg.



  Elemental analysis:
 EMI296.6
 
 <tb> Theoretical <SEP> Analytics <SEP>
 <tb>
 <tb> C <SEP> (%) <SEP> 80.91 <SEP> 81.09
 <tb>
 <tb>
 <tb> H <SEP> (%) <SEP> 12.31 <SEP> 12.18
 <tb>
 <tb>
 <tb> N <SEP> (%) <SEP> 3.35 <SEP> 3.51
 <tb>
 

  <Desc / Clms Page number 297>

 Example 1592
Laying for 2 hours, a mixture of 10 g was brought to reflux.
 EMI297.1
 of methyl palnitate, of 611 adamantylamine, of 50 ml of bonzéno and of 2 g of sodium ethoxide, to obtain a desired product of a P.E. of 1ì2-a.O6t'rp'3 mm of Hg.



  Elemental analysis:
 EMI297.2
 
 <tb> Theoretical <SEP> Analytics
 <tb>
 <tb> 0 <SEP> (%) <SEP> 80.14 <SEP> 00.31
 <tb> H <SEP> (%) <SEP> 12.16 <SEP> 12.05
 <tb>
 <tb> N <SEP> (%) <SEP> 3.60 <SEP> 3.51
 <tb>
 Example 1593
For 50 hours, a mixture of 10 g was heated at 150 ° C.
 EMI297.3
 d. est01 'methyl of carthamo oil and 6 g of adamantylanine, then it was distilled to obtain 11.2 g of a desired product of a
 EMI297.4
 P.E. of? 7-'99 c / o, o Dm of Hg.



  Example 1594
At 40 hours, a helangal (10 g of cod liver oil ethyl ester and 6 g of adamantylamine was heated to 150 ° C. to obtain 9.2 g of a desired product. of a PE of 160-213 C / 0.03 mm Hg.

  <Desc / Clms Page number 298>

 



    The following acids are also synthesized according to the methods mentioned above.
 EMI298.1
 L - JLi-JI.JL ¯w¯¯¯¯ $ ', w¯¯¯¯¯¯¯¯¯¯..¯.w¯ ¯L Il% i --¯¯ ------- ---.---- ¯¯ .¯¯¯¯.¯¯¯, ¯.,. ¯¯¯¯¯¯.,. ¯¯ --------------- ----- 'ID Theoretical Analytical Theoretical' analytical Theoretical; Analytical \ ll, #####.



  Z? H33CONHCiJJI / - N02 23 1 512) i2, E36 72.90 il 9t2? i 6.54 6.44 7H31COr: H'G'Hr.NO2 Ce) 22 1, 511E '1 72.86 i;' ?, 95 9.41 9.22 6.54 6.43 (d), rv -NOg jp33C NEE ± $ <d>, 5123) 72? 95 'J3 Lê 9,9? 1 '? 6.3 "6.19 CONH # - No2 iz 72.93 73.12 9.97 10 0? E ,,: 6.19 't. 7g33 - N02 z 33 1.5122 72.93 73, io 9, 9710.05 6.30 z.5 O2H5 (d), P29CONHOE4 '- \ - NO2 32 1.5012 73.60? 3.3032 9 1 5 9.2C 6, 36 6' C2H5 ....-. .-.... # ..-...... ¯¯ ..-. I ... '. ¯¯ ------- .... ¯ ... ¯ i ... . '.....

  <Desc / Clms Page number 299>

 
 EMI299.1
 iµ2g '/ ± / 2 1.5020 ??, 60 73.76 9.15 9.22 9.35 6.22 Clr29CONHCHvN02 1 1.5020, 60 73.76 9.15 9.22 9.35 6.22 CzR 1 lij! ! ISO-clrH35coNHCHm2 C tU), 27 1.5163! ? 2.1B 72.00 10.25 10.09 6.48 6.52 Iso-CipcoxFÉP'0z 1 5163) 72.18? 2> 1 .25 1 9) 6 'bzzµ ......



  1 i Oil of (f!. 'O 24 1.5140 carthane-COmICjJ .. N02:: c3 1 Oil of () 20 1.5142 7 c.rthane-COICH --- b0.! Oil (d), r <\ = / 1.5222 i 1 1 Hui17 of (d) - (} - N 1.5222 fi.



  CH3; f "1 /) ± '" "' / ± P 2 3 Ç '1 23 1.5220 J sardine- # iÇH -') - NO sardine-CONHÇH, 02 l CR \ ==) '.! 1 ¯ ... ¯ .¯r.¯ --...- ¯-¯! ..%:

  <Desc / Clms Page number 300>

 
 EMI300.1
 PE c% -. ". ¯¯ ....,. ¯ .. 11% - r., .. ¯ 1 N .... - ###### - #### - ### ¯ ¯¯¯ ## JL-L ¯¯¯. ######## j # ¯¯¯ji; if Tea; iq., - ;; 1 ;; - ;;;;:. ::: u ;; -; "- ;;; 1; ts .- ;;; c.ocO- 3 0aff 3 2ï4-223 / 0.04 78.40 "-13.49 lo, 4F3 10.66; 3.9 ¯¯¯¯¯¯¯¯ 3 33 CFI 3 fi.!!: conO J22VO, '! 78 ,,' t! ',! 10. if, <JI) C "3 214-224 / 0, QlI. 7, S94o 'l8.53 10.48 10, & 3 3.39 3320 CS 3 < <) 7x33corrR. 3 i t! 210-221 / 0.05 '. 'Iu, 02 73.2'-' 10,) 1;

   ! ! td) (d) 1? H33CONECH - CC 3 213-223 / p, 03?, 02 7! 3.21 1 () $ 9i ..16 3.37 3.22 OE3 213-223 / 0.03 '78, 02 'i' !!, 21: 1. (\, 9: 1. 11; 16 1 3.37 3.922 CH3 t (f>? T33corrHCC ... oc3 3 1 213-225 / 0.03 IZBI02 78.19 10.91 lz, og 3.3'7 3.3D

  <Desc / Clms Page number 301>

 
 EMI301.1
 Iso - C i7g35 CONHOB '' 'o 2Z .-. 22 / 0.04 77.64 77.77 3131- i 11.50 3.35 3.50 Tso-G17H351HCH - OCH3 216-22F / 0.03 fi 77 , 64 77.80 11.34 11 48 3.35; 3.52 ol7gcocâ f oog -cI? -225 / 0.05 79.61 73.42 10.18 10.12. 3.29 340 'Cle2, c, CONERIT 217-227 / 0.0-5 79.61 79.53 10 10.20 3.29 3.35 iiuiie of E / 8-2- 7 / +) = ce-rHCg. -o3; 3 208-227 / 0, M Iluile de ( <c) .c- &. '210-227 / 0.03 sardine-COI G'H 3 OCH3 i ¯ bzz¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯ ± ¯¯¯! .¯.¯¯ ... ¯¯ ... ¯¯¯ ¯: bzz.

  <Desc / Clms Page number 302>

 
 EMI302.1
 j 1 CoL i H% N% i Theoretical, µ Analytical ¯ = -Theoretical! = kna3ytic:

   Theoretical = Analytical j <d) .-. ¯.w¯¯¯¯¯¯¯ ¯¯¯¯w..¯ .. -j! - ¯¯¯¯¯¯¯¯¯¯ o ¯¯..¯¯ Cl7133CONHCHO (d) 1. Sem-solid! 83.24. 83.33 i 10.26 101145 3.03 t 3.31 Iii! 1 '/) fi! , i t '"3.?H33COItHC 83.24 g 83.40 i 10.26 10.39 3.03 2.94 2 fI' C112 j 1 l 'il! j! (d) (# i # CH - 83.97 84.01 9.47 9.67 3.06 3.00? 9 "'εlj (d) bzz? Bzz?) Bzz? . <1.COCI! -O 1: 83, '17 84.01 9.67 3.06 3.00 lit 1 ....... --........! ..... ..

   Ir --- -------..... the III RIIVl ------ '1 "" --- 1 .... - T - .---- ¯.a. ..d - - b ....... - h ....., AJ <! -

  <Desc / Clms Page number 303>

 
 EMI303.1
 fl 1 () Seni-aolide- '03.97 9 d, a3 i * î 9.4? i 9.53! : 3,: r 2.99 ¯) 17't29 ('cqz ElY j 1' 1 i '1 i 1 ji! I!,' 1 'i jj Ù [' j> 'jj. To 1' '(d ) If cw, zz .. 9? 3 '".?'; G 129 coPtHCH- 1 83.97 .22 9.47 9.57) 3.06 3.21 cipzcoxHpÔ c% 1 j 1, j> [i 't J' "j 1 Î. Î Î '' 6: - '"" "2 7 CIL fi Ii j 0 1');! LtGLU.i VV11B411 CEg t = j Ph j 1 j Î 1 1 j 1) r, II Oil of <1> 0 r sa.rd3.ae-CICgCH- t i CEL, i r !! ¯¯ ¯ j¯¯¯¯¯j¯¯¯, ¯L # -.- #! - ### i - # - i

  <Desc / Clms Page number 304>

 
 EMI304.1
 1 p.B, C% H% 'fi7 1 CC / mm Theoretical Anaiiq-; i éori ;; -: Ïa; y1; i-; -Théo; i; -f1i '; ef. ¯¯¯¯¯¯¯¯¯¯Lf fll.:l! Theoretical Analytics.

   Analytical ClrH33CONHCH-Q-Br (d) 222-236 / 0.06 t 67.24. 1 1 67.40! 9.05 c, 97 3.01 2 76! Cle33CONHM-0-B '222-236 / 0, cob 67.24 67.40 9.05 8997 3, C- 2.78 OE3 1 222-236 / O, OS) 67.2W i' 9.05 3, yes 2.78 CCONH # - Br 3 219-223 / 0.03 67.24! J 67.30; J 9.05 9.15 3.01 2.84 C11I33CONHFOBr CH3 i 219-223 / 0.03: 67.24 67.33: 9> 5 9PI5 3.01 2.84 1; f ISO-rr35CON1Ir-Q- <. "" l (i). '215--230 / 0.05 ft' Î 'l4.02 -74 ego ID. "3 10.65 3.32 JI., ;;, 19 CH 3 215-230 / 0.05 il!! 74.20 f 10.43 10.65 332! J 3 '19 (d) Iso- 214-232 / 0.05 74902 î4 21 10.43 10.67 3.32 3.30 CH3! CCONH # 20r, -217 / 0, 05 75.09 75 24 9914- 5.33 3t36 3.29 ClrH29CONHyn- (Y (1) CH, 205-217 / 0.05 / 75.09 75.2lui- 9.14 j 1; .. 33 3.36 3.29 ..------------------------------ - - "5), j ------ ¯,; j, /, / 't <

  <Desc / Clms Page number 305>

 
 EMI305.1
 (d) .- d;

   -0 t 1 * -a9 / O, 04) 75.09 t 75,>) 9,>) r 9.30 3.36 ± 3.2 j. 1 cn) 'Î j Î b' l / 1 1 Oil of (d) / safflower-CONHCHO 1 Br! 215-224 / 0.03 1 C2HS '== 25? 1] 1 if 'Oil aCUI (H) Îiikài-C0llÀhn 213-22510.03 lI5. ! i! , Oil () Cl j Oil of ({.) (J el pleuronecte-CONHCH- 190-232 / 0.04 Pleuronecte-CONHCH-o- 1 190-2.32 / 0.04 5 1% -232 / O, OV) tif Oil (cL) / r- 'ff Oil of (d) Cl t J f! pleuronecte-CONHCH '= J 192-228 / 0.03 i Il! i. he! VS!

  <Desc / Clms Page number 306>

 
 EMI306.1
 j Trr f - ¯ ¯ ¯: Analytical Theoretical; Theoretical ..ualtique: Theoretical Analytical (d) -.- .; ¯¯¯¯¯¯¯.i ¯¯¯¯¯¯¯¯¯; ¯.¯¯¯¯¯¯¯¯¯¯; i ...... ¯ .... t µ (d> ¯ j 1 ------------, --------- to 81.43 11.45 11 , 55 ----------- 1 3.22 C2 "5 200-218 / 0.05 811.29 81.43 11.45 11.55 3.39 3.22 ¯.



  C3.3''JCOIn3CH - 5 CH 3 i 200-21 $ / 0.05 81.29 81.50 1¯., 45 11.52 3.39 21 ff * ISO-ClII35CC'NHGH. 1 -CH.3.9--23.5 / 0.06 80.73 f3Cs, 93. 11, G3 12.02 3 e49 z.2 i cH3 '80.73 80.9i 11> G3 12.02 3, <9 3> 4a Iso-CCONH # - # () 195-214 / 0.06 80.73 CO.CG 11, G3 12.07 5.49 3.39 rso 7H35 cosc - cg zgs..214 / 0 06 80.73 80.86 ilV, '-, 12.073, 49 3.39 3 19S-2 /, ") 8,? 3S ?,"). ', Ô3 z / 12.? ) '1?, * 9 3.39 - \ c,%. f1ccs 210-221 / 0.04 el, 97 82.14 10.45 10962 3.54 3.47 '' M3 1,, ¯-¯-¯¯¯¯¯ - ¯ -------- 1 ------------- W ------- '------- l ------- --------- W-- ----- ¯¯ - 1¯¯¯ ¯¯¯¯

  <Desc / Clms Page number 307>

 
 EMI307.1
 C "3 209-218 / 0404 8199? 62913 10945 0.5, 3.54- 3939 C" 3: 8l, ?? ) '")'" Oil (d) / r 'Oil (d) crthane-CONHGl.'H.-t; t 200.212 / 0.03! G'H3 \ = ay Oil of (;

   a4 / 0, 3) 1 d µ char +, 200-214 / 0.03 lanthanum "" n3 fTT Oil of (d) ... arel-COüiC3 I 194-22 / o, ot 'Oil 3 = Oil of <é> Cb g¯ / o, ow herring-00 190-226 / 0.04; hmMC # MK # Hj 3 190-226 / 0.04 '"" t $ "3 o--" "' '"' "'' '

 

Claims (1)

CLAIMS 1. Compound of formula EMI308.1 in which R represents a synthetic or natural aliphatic chain, saturated or not, branched or straight, C13-C25, oompaining an OH group or not, R 'represents a d- or l- [alpha] - group EMI308.2 alkyl-inhibitor.-bonzy3o a lower alkyl-bonzyl racemic, [alpha] - or 1- -substituted group having substituents on the benzene ring, for example a lower alkyl group, a halogen atom, a lower alkoxy group or a nitro group one EMI308.3 group d- or .- 0 benzyl-bonzyla raconiquo or an adamantyl group, R "represents an atom of hydrogen or R 'and R" both represent a cyclohexyl group and, when RCO represents an isostearoyl group, R' represents, in addition to the above groups, a EMI308.4 alkyl group, acenylo, cycloclicoyl, alkyl-cycloalkyl, hy- droxy-cycloalkyl, alkoxv-cycloalkoyio, alkyl-aryl, hydroxy-arylo, alkoxv-aryl, halo-arylo, halo16no-alooyo-l6-anylo -aryl, alkoxy-halo-aryl and aralkyl, alkyl-aralkyl, hydroxy-aralkyl, alkoxy-analkyl or a rllc-o (-lower alkyl-aralkyl group and R "represents a hydrogen atom, one or l 'other of the groups represented by R' or a heterocyclic group (of 7 carbon atoms or less) consisting of NR'R "containing an oxygen atom or not. 2. A pharmaceutical composition comprising, as an essential active component, a compound according to claim 1. 3. Process for the preparation of a compound of formula EMI308.5 in which R, R 'and R "have the same meanings as those indicated in claim 1, characterized in that it comprises <Desc / Clms Page number 309> the 'tapas which consisting of; (1) reacting a fatty acid of formula EMOU with an amine of EMI309.1 rnul lm IlleR fomulo RN (RI is the presence or absence of an agent of R "dehydration or (2) reacting a fatty acid halide -the formula RCOX, in which X represents a halogen atom, with a healthy of EMI309.2 formula HI, there is present a basic condensing agent R "or (3) reacting an inner alkyl ester or a glyceride of a fatty acid of formula RCOOH, with an amine of the formula EMI309.3 R 'presonco absence of a solvent of an EN <,, in presonco or abaenoo of a solvent and a condensation agent or (4) reacting a nixto acid anhydride of a fatty acid do EMI309.4 torI! lulo RCOOHt ce "li an'l: 1ydrl de 1'Ó: laying down: rorm \ 'e RCO> 0 R"' CO in which R '"represents an alkyl or halo-alkyl group of 1 to 4 atons of carbon, with an amine of the formula EMI309.5 R 'IL, "IlR 1b is assumed to be a basic condensation catalyst,' '' Ru R ot R 'having, in steps (1) to (4) above, the same meanings as indicated in the rovendication 1.