USRE19194E - Production of organic products - Google Patents
Production of organic products Download PDFInfo
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- USRE19194E USRE19194E US19194DE USRE19194E US RE19194 E USRE19194 E US RE19194E US 19194D E US19194D E US 19194DE US RE19194 E USRE19194 E US RE19194E
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- 238000004519 manufacturing process Methods 0.000 title description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 9
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 235000011149 sulphuric acid Nutrition 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000011007 phosphoric acid Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- -1 trlchlorethylene Chemical compound 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N Oleyl alcohol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- 230000001603 reducing Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 102100000129 CHURC1 Human genes 0.000 description 1
- 101710014631 CHURC1 Proteins 0.000 description 1
- 102100004002 CORIN Human genes 0.000 description 1
- 101700055510 CORIN Proteins 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N Ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- WBHHMMIMDMUBKC-GKUQOKNUSA-N Ricinoleic acid Natural products CCCCCC[C@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-GKUQOKNUSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- JBUKJLNBQDQXLI-UHFFFAOYSA-N Sodium perborate Chemical compound [Na+].[Na+].O[B-]1(O)OO[B-](O)(O)OO1 JBUKJLNBQDQXLI-UHFFFAOYSA-N 0.000 description 1
- 229940091252 Sodium supplements Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZZRCKSSPGJOTEE-UHFFFAOYSA-L disodium;carbamoyl phosphate Chemical class [Na+].[Na+].NC(=O)OP([O-])([O-])=O ZZRCKSSPGJOTEE-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001804 emulsifying Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N triclene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
Definitions
- the present invention relates to the production of new organic products.
- the conversion of 7.18-stearic glycol into an unsaturated alcohol may be effected by heating for some hours to temperatures of from about 50 to about 200" C. with an addition of strong nonoxidizing acids.
- Organic sulphonic acids such as naphthalene sulphonic acids, and also highly concentrated aqueous solutions of strong inorganic polybasic acids, as for example about 90 .per cent aqueous phosphoric or sulphuric acids, are particularly suitable for the said purpose but also chloracetic acid may be employed.
- the said The advantage of the process according to the higher quantities such as from 1.2 to 10 molecular proportions.
- the splitting off of water proceeds especially smoothly when first of all the monochloracetate is formed by heating the 7.18-stearic glycol with an equimolecular proportion of monochloracetic acid to from 180 to 200 C. If a little more than 1 molecular proportion of monochloracetic acid be used for each molecular proportion of stearic glycol for the esterification, or if a further amount of monochloracetic acid be added after the esterification has been carried out with 1 molecular proportion of monochloracetic acid, and the whole be heated for some hours at about 200 C., the said splitting off of water takes place smoothly and the chloracetate of an unsaturated alcohol is obtained from which the alcohol itself may be obtained by saponiflcation, I
- the alcohol may be treated for about 1 hour at a temperature of from about 0 to 50 C. with its own weight of sulphuric acid oi 96 per cent strength, or the alcohol may also be dissolved in an inert solvent, such as etfwl ether or carbon tetrachloride, and treated at about 20 C.
- esters obtainable in this manner correspond presumably to the formula Y being hydrogen or an alkali radicle or, in the case of a diester, for example to the formula CH.1(CH:)eR(CH:)o-CH:OSO3Y in which R denotes I [CHZ-CHZ-CHZ] in which one of the 2's denotes OS:Y,.
- Zs denote hydrogen and Y denotes hydrogen or an alkali metal radicle which latter can be obtained by the employment of a mixture of chlorsulphonic and sulphuric acids, or as a mixture containing preponderating quantitles of such di-ester.
- the unsaturated alcohol may also be dissolved in about its own weight of acetic anhydrlde and at least one equimolecular proportion of sulphuric acid of 100 percent strength may be added, the mixture being kept at a temperature of from about 10' to 20 C.
- a sulphonic acid may be formed which presumably corresponds to the formula CHs-(CEzh-[CHZ-CHZ-CHZl- (cum-onion inwhichvicinalZ'sdenoteSOaHand-OH andtheremainingzdenoteshydrogenl
- Thecompoundsobtainedinthesaidmanner may be employed either as such or in the form' oftheiralkalisaltasuchassodium,potassium orammoniumsaluforagreatvarietyofpurposesindomesticandindustrialusebyreason of their excellent wetting, cleansing and emulsifylngpower.
- Inparticulartheyarecapableof wide employment in the textile industries as for exampleaswetting. washing,levelling and like agentsorforsofteningartiilcialsllk. Theymay be employedalone or together with a great variety of additions, such as salts, as for example common salt, Glaubers salt or sodium perborate, acids,"such as aqueous dilute solutions of organic or mineral acids, alkalles, glue, water-soluble or water-insoluble solvents, oils of mineral, vegetableoranimalorigimsoapsandlikeagentsused in the textile and related industries.
- salts as for example common salt, Glaubers salt or sodium perborate
- acids such as aqueous dilute solutions of organic or mineral acids, alkalles, glue, water-soluble or water-insoluble solvents, oils of mineral, vegetableoranimalorigimsoapsandlikeagentsused in the textile and related industries.
- Emmple 1 '288 parts of 'Lls-stearic glycol (obtainable by the catalytic reduction of castor oil according to the British Patent No. 356,731) are heated; while leading in a currentof nitrogen into the mixture. with 125 parts of chloracetic acid for 5 hours at from 180' to 200' 0., whereby about38 parts of water are split oil.
- the chloracetate obtained is saponifled by boiling for several hours with 1500 parts of an aqueous caustic soda solution 0110 per cent strength.
- it may be distilled at from 150' to 210 C. at a pressure of 2 millimeters mercury gauge.
- Example 2 '14 parts of 7.18-stearic glycol (ll-acetate are heated together with parts of chloracetic acid for 2 hours at 200" C. while passing through'a current of nitrogen, whereupon the whole is heated to 250 C. for 2 hours and then to boiling for the same length of time with 500 parts of a 10 per cent ethyl-alcoholic caustic potash solution the alcohol being then distilled off. By adding water, the unsaturated alcohol formed is-precipitated. If desired, the latter may be purified by distillation at a pressure below atmospheric pressure.
- Example 3 2'! parts of the alcohol obtained by acting with chloracetic acid on 7.18-stearic glycol and subsequent saponiflcation as described in Example 1 aredissolvedin 200partsofethyl etherandthen intimately stirred with parts of phosphoric pentoxide for 24 hours.
- the reaction product is poured onto iceand the resulting solution is neutralized with aqueous caustic soda solution.
- the supernatant ethereal layer is separated from the aqueous layer and washed with water.
- the aqueous solutions are then inspissated whereby a product having a good emulsifying power "is obtained.
- the ph phoric ester responds to the formula and may be employed in the form of its monoor di-sodium salts.
- concentrated sulphuric acid are added while cooling to a mixture of parts of trichlorethylene and parts of'an lmsaturated-alcohol obtained, according to Example 1 by the action of chloracetic acid'on 'LIB-stearic glycol. After stirring for 2' hours the reaction mixture is poured onto ice, rendered neutral with the aid of aqueous caustic soda solution and then evaporated to dryness.
- a product which, besides sodium-chloride and sodium sulphate, consists of a mixture of sulphuric acid salts of the said alcohol, a preponderating quantity 'of which salts corresponds to the formula premmably corin which one of the Zs denotes (OSOaNa) and the remaining .two Zs denote hydrogen.
- X denotes hydrogen, -O SOaY or OPO(OY) 2, Y being hydrogen or an alkali metal radicle.
- Y denotes hydrogen or an alkali metal radicle.
- R denotes [CHZCHZCHZ] in which one of the Zs denotes O-SO:Y, the no remaining Zs denote hydrogen and Y denotes hydrogen or an alkali metal-radicle.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Description
Reissued June 5, 1934 PRODUCTION OF ORGANIC PRODUCTS FRQM 'LIS-STEARIC GLYCOL Fritz Guentherand Karl Sai'tien, Ludwigshafenon-the-Rhine, Germany, assignors to I. G. Farbenindustrie Aktiengesellschai't, Frankforton-the-Main, Germany No Drawing. Original No. 1,942,812, dated January 9, 1934, Serial No. 604,863, April 12, 1932. Application for reissue April 12, 1934, Serial No. 720,494. In Germany April 29, 1931 9 Claims.
' The present invention relates to the production of new organic products.
We have found that a new organic material which can be converted-into valuable assistants for the textile and allied industries, in particular wetting, cleansing, dispersing and like agents, can be obtained by splitting off one molecular proportion of water from the 7.18-stearic glycol -obtainable by the reduction of ricinoleic acid or its 10 esters, the resulting unsaturated alcohol being then converted into water soluble products by treatment with a strong polybasic mineral acid substance selected from the group consisting of sulphonating agents and phosphoric acid or its derivatives.
The splitting oil of water very probably takes place at the secondary hydroxyl group and a product isomeric with natural oleyl alcohol cH3- (cm) -l cn=cn cm women:
9.10-octo-decene-18-ol) is obtained which differs from the latter in the position 01' the double linkage.
present invention contrasted with that described in the British Patents Nos. 308,824 and 317,039 consists in the fact that the oleyl alcohol used as initial material in the said specifications only occurs in nature in limited quantities or can only be obtained in a troublesome manner by reducing alkyl esters of oleic acid with the aid of sodium, whereas the conversion of 7.18-stearic glycol into an unsaturated alcohol may be efiected very readily and-furthermore the preparation of 85' 7.18-stearic glycol by the catalytic hydrogenation 01' castor oil (which is available in unlimited amounts) oil'ers no dimculty, such process being described for example in the British Patent No. 356,731.
The conversion of 7.18-stearic glycol into an unsaturated alcohol may be effected by heating for some hours to temperatures of from about 50 to about 200" C. with an addition of strong nonoxidizing acids. Organic sulphonic acids, such as naphthalene sulphonic acids, and also highly concentrated aqueous solutions of strong inorganic polybasic acids, as for example about 90 .per cent aqueous phosphoric or sulphuric acids, are particularly suitable for the said purpose but also chloracetic acid may be employed. The said The advantage of the process according to the higher quantities such as from 1.2 to 10 molecular proportions.
The splitting off of water proceeds especially smoothly when first of all the monochloracetate is formed by heating the 7.18-stearic glycol with an equimolecular proportion of monochloracetic acid to from 180 to 200 C. If a little more than 1 molecular proportion of monochloracetic acid be used for each molecular proportion of stearic glycol for the esterification, or if a further amount of monochloracetic acid be added after the esterification has been carried out with 1 molecular proportion of monochloracetic acid, and the whole be heated for some hours at about 200 C., the said splitting off of water takes place smoothly and the chloracetate of an unsaturated alcohol is obtained from which the alcohol itself may be obtained by saponiflcation, I
In order to convert the resulting unsaturated alcohol, which is apparently an octodecene-lB-ol in which the double linkage is connected to the seventh carbon atom of the chain, into watersoluble products it is treated with an at least equimolecular proportion of a strong polybasic mineral acid substance selected from the group consisting of sulphonating agents and phosphoric acid or its derivatives such as sulphuric acid, oleum, amidosulphonic acid (NHz-SO3H), sulphur trioxide or chlorsulphonic acid, or with phosphoric acid or its acid reacting derivatives such as phosphorus pentoxide and phosphorus oxychloride, if desired with an addition of agents capable of combining with water such as acetic anhydride. When oleum, sulphur trioxide or chlorsulphonic acid are employed it is preferable to work in the presence of inert, organic liquid diluents, such as carbon tetrachloride, trlchlorethylene, ethyl ether, glacial acetic acid or like inert organic solvents, since otherwise dark colored products may be readily formed. Thus, for example, the alcohol may be treated for about 1 hour at a temperature of from about 0 to 50 C. with its own weight of sulphuric acid oi 96 per cent strength, or the alcohol may also be dissolved in an inert solvent, such as etfwl ether or carbon tetrachloride, and treated at about 20 C. for about 80 to 60 minutes with an..equimolecular proportion of chlorosulphonic acid. The esters obtainable in this manner correspond presumably to the formula Y being hydrogen or an alkali radicle or, in the case of a diester, for example to the formula CH.1(CH:)eR(CH:)o-CH:OSO3Y in which R denotes I [CHZ-CHZ-CHZ] in which one of the 2's denotes OS:Y,.
the remaining Zs denote hydrogen and Y denotes hydrogen or an alkali metal radicle which latter can be obtained by the employment of a mixture of chlorsulphonic and sulphuric acids, or as a mixture containing preponderating quantitles of such di-ester. The unsaturated alcohol may also be dissolved in about its own weight of acetic anhydrlde and at least one equimolecular proportion of sulphuric acid of 100 percent strength may be added, the mixture being kept at a temperature of from about 10' to 20 C. for about 8 hours; in this case, after saponiflcation of acetyl groups, a sulphonic acid may be formed which presumably corresponds to the formula CHs-(CEzh-[CHZ-CHZ-CHZl- (cum-onion inwhichvicinalZ'sdenoteSOaHand-OH andtheremainingzdenoteshydrogenl Thecompoundsobtainedinthesaidmanner may be employed either as such or in the form' oftheiralkalisaltasuchassodium,potassium orammoniumsaluforagreatvarietyofpurposesindomesticandindustrialusebyreason of their excellent wetting, cleansing and emulsifylngpower. Inparticulartheyarecapableof wide employment in the textile industries, as for exampleaswetting. washing,levelling and like agentsorforsofteningartiilcialsllk. Theymay be employedalone or together with a great variety of additions, such as salts, as for example common salt, Glaubers salt or sodium perborate, acids,"such as aqueous dilute solutions of organic or mineral acids, alkalles, glue, water-soluble or water-insoluble solvents, oils of mineral, vegetableoranimalorigimsoapsandlikeagentsused in the textile and related industries.
The following examples will further illustrate the nature of this invention but the invention is not restricted to these examples. The parts are by weight.
Emmple 1 '288 parts of 'Lls-stearic glycol (obtainable by the catalytic reduction of castor oil according to the British Patent No. 356,731) are heated; while leading in a currentof nitrogen into the mixture. with 125 parts of chloracetic acid for 5 hours at from 180' to 200' 0., whereby about38 parts of water are split oil. The chloracetate obtained is saponifled by boiling for several hours with 1500 parts of an aqueous caustic soda solution 0110 per cent strength. In order to purify the product which separates out as an oily layer on the top of the aqueous liquid, it may be distilled at from 150' to 210 C. at a pressure of 2 millimeters mercury gauge.
50 parts of the unsaturated alcohol (octodecenol, in which the double linkage is presumably on either side of the seventh carbon atom) thus obtained are dissolved in 150 parts of ethyl ether and a mixture of 23 parts of chlorsulphonic acid and 50 parts of ethyl ether is added while cooling to about 15 C. After stirring for one hour the reaction product is poured onto ice, neutralized with an aqueous caustic soda solution and the ethyl ether is evaporated. In this manner 'a product having excellent washing and wetting power is obtained,'which, besides some common salt contains the sulphuric ester sodium salt corresponding presumably to the formula (CH2) s-CHz-OSOsNa.
Example 2 '14 parts of 7.18-stearic glycol (ll-acetate are heated together with parts of chloracetic acid for 2 hours at 200" C. while passing through'a current of nitrogen, whereupon the whole is heated to 250 C. for 2 hours and then to boiling for the same length of time with 500 parts of a 10 per cent ethyl-alcoholic caustic potash solution the alcohol being then distilled off. By adding water, the unsaturated alcohol formed is-precipitated. If desired, the latter may be purified by distillation at a pressure below atmospheric pressure.
The conversion of the unsaturated alcohol into a water-soluble product is carried out with chlorsulphonic acid and ethyl ether as described in Example 1.
Example 3 2'! parts of the alcohol obtained by acting with chloracetic acid on 7.18-stearic glycol and subsequent saponiflcation as described in Example 1 aredissolvedin 200partsofethyl etherandthen intimately stirred with parts of phosphoric pentoxide for 24 hours. The reaction product is poured onto iceand the resulting solution is neutralized with aqueous caustic soda solution. The supernatant ethereal layer is separated from the aqueous layer and washed with water. The aqueous solutions are then inspissated whereby a product having a good emulsifying power "is obtained. The ph phoric ester responds to the formula and may be employed in the form of its monoor di-sodium salts.
Example 4 parts of chlorsulphonic acid and 20 parts of,
concentrated sulphuric acid are added while cooling to a mixture of parts of trichlorethylene and parts of'an lmsaturated-alcohol obtained, according to Example 1 by the action of chloracetic acid'on 'LIB-stearic glycol. After stirring for 2' hours the reaction mixture is poured onto ice, rendered neutral with the aid of aqueous caustic soda solution and then evaporated to dryness. A product is obtained which, besides sodium-chloride and sodium sulphate, consists of a mixture of sulphuric acid salts of the said alcohol, a preponderating quantity 'of which salts corresponds to the formula premmably corin which one of the Zs denotes (OSOaNa) and the remaining .two Zs denote hydrogen.
What we claim is:
l. The process for the production or organic ular proportion of water from 7.18-stearic glycol by heating the latter to from about 100 C. to about 200" C. in the presence of a strong nonoxidizing acid selected from the group consisting of phosphoric acid, sulphuric acid. organic sulphonic acids and halogen acetic acids.
2. The process for the production 01 organic products which comprises splitting oi! one molecular proportion of water from 7.18-stearic glycol by heating the monochloracetate of 7.18- stearic glycol to about 200 C. in the presence of a strong non-oxidizing acid selected from the 1 group consisting of phosphoric acid,sulphuric acid, organic sulphonic acids and halogen acetic acids and saponii'ying the resulting unsaturated ester. 1
3. The process for the production oi. organic products which comprises splitting 01! one molecular proportion oi water from 7,18-stearlc glycol and reacting the resulting unsaturated primary alcohol with an at least equimolecular proportion of a strong polybasic mineral acid substance selected from the group consisting of suiphonating agents and phosphoric acid, its an hydrides and oxyhalides.
4. The process for the production of organic products which comprises splitting oil one molecular proportion of water from 7.18-stea'ric glycol and reacting the resulting unsaturated primary alcohol with an at least equimolecular proportion of chlorsulphonic acid in the presence of an inert, organic liquid solvent.
5. The process for the production of organic products which comprises splitting oil? one molecular proportion of water from 7.18-stearic glycol and reacting the resulting unsaturated primary alcohol with an about equimolecular quantity of chlorsuiphonic acid in the presence or ;,etliyl ether at about 15 0. products which comprises splitting oil! one M1001,
X denotes hydrogen, -O SOaY or OPO(OY) 2, Y being hydrogen or an alkali metal radicle.
8. An acid sulphuric ester substance corresponding to the formula CH:(CH2) 4 R(CH2) t-cmosonr,
in which R denotes [--CH=CHCH:]
and Y denotes hydrogen or an alkali metal radicle.
9. An acid sulphuric ester substance corresponding to the ionnula CHz-(CHz) t-R-(CHz) r-CHzOSOJY.
in which R denotes [CHZCHZCHZ] in which one of the Zs denotes O-SO:Y, the no remaining Zs denote hydrogen and Y denotes hydrogen or an alkali metal-radicle.
mrrz curm'mm. KARL sar'rmn.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE19194E true USRE19194E (en) | 1934-06-05 |
Family
ID=2083122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US19194D Expired USRE19194E (en) | Production of organic products |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE19194E (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2454936A (en) * | 1944-01-22 | 1948-11-30 | Commercial Solvents Corp | Process for preparing unsaturated alcohols |
| EP0015318A1 (en) * | 1979-02-07 | 1980-09-17 | Chemische Werke Hüls Ag | Method of producing pure alpha,omega-C6 to C20 alkenols |
-
0
- US US19194D patent/USRE19194E/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2454936A (en) * | 1944-01-22 | 1948-11-30 | Commercial Solvents Corp | Process for preparing unsaturated alcohols |
| EP0015318A1 (en) * | 1979-02-07 | 1980-09-17 | Chemische Werke Hüls Ag | Method of producing pure alpha,omega-C6 to C20 alkenols |
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