US1799536A - Twvpom - Google Patents
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- US1799536A US1799536A US1799536DA US1799536A US 1799536 A US1799536 A US 1799536A US 1799536D A US1799536D A US 1799536DA US 1799536 A US1799536 A US 1799536A
- Authority
- US
- United States
- Prior art keywords
- lactone
- oxy
- lactones
- degrees centigrade
- carboxylic acid
- Prior art date
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- 150000002596 lactones Chemical class 0.000 description 68
- 239000002253 acid Substances 0.000 description 20
- 150000002576 ketones Chemical class 0.000 description 20
- 239000000203 mixture Substances 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- OSOIQJGOYGSIMF-UHFFFAOYSA-N Cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- 230000001264 neutralization Effects 0.000 description 12
- DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 10
- -1 carboXyl group Chemical group 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 4
- FUGDHQXYVPQGLJ-UHFFFAOYSA-N Cyclotetradecanone Chemical compound O=C1CCCCCCCCCCCCC1 FUGDHQXYVPQGLJ-UHFFFAOYSA-N 0.000 description 4
- ALHUZKCOMYUFRB-OAHLLOKOSA-N Muscone Chemical compound C[C@@H]1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-OAHLLOKOSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atoms Chemical group C* 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- KBQDZEMXPBDNGH-UHFFFAOYSA-N cycloheptadecanone Chemical compound O=C1CCCCCCCCCCCCCCCC1 KBQDZEMXPBDNGH-UHFFFAOYSA-N 0.000 description 4
- LXJDKGYSHYYKFJ-UHFFFAOYSA-N cyclohexadecanone Chemical compound O=C1CCCCCCCCCCCCCCC1 LXJDKGYSHYYKFJ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 125000004430 oxygen atoms Chemical group O* 0.000 description 4
- 239000002304 perfume Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- XJDBBMWXVYBUTB-UHFFFAOYSA-N 2-methylcyclopentadecan-1-one Chemical compound CC1CCCCCCCCCCCCCC1=O XJDBBMWXVYBUTB-UHFFFAOYSA-N 0.000 description 2
- XEFOHUNTIRSZAC-UHFFFAOYSA-N 2-methylpentadecanoic acid Chemical compound CCCCCCCCCCCCCC(C)C(O)=O XEFOHUNTIRSZAC-UHFFFAOYSA-N 0.000 description 2
- ALHUZKCOMYUFRB-UHFFFAOYSA-N 3-methylcyclopentadecan-1-one Chemical compound CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 2
- UEVXKGPJXXDGCX-UHFFFAOYSA-N Cyclotridecane Chemical compound C1CCCCCCCCCCCC1 UEVXKGPJXXDGCX-UHFFFAOYSA-N 0.000 description 2
- 241000282375 Herpestidae Species 0.000 description 2
- 229920002892 amber Polymers 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000003301 hydrolyzing Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OTCVAHKKMMUFAY-UHFFFAOYSA-N oxosilver Chemical compound [Ag]=O OTCVAHKKMMUFAY-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
Definitions
- 1,7 02,842 to 1,702,852 inclusively for instance. from 2-methyl-cyclopenta-decane-lone (lqnethyhexaltone) a mixture of lactones of the 14-oXy-14-methyl-tetradecane-1 carboxylic acid and the 14-oxy-1-methyl-tetradecane-l-carboxylic acid and from 3- methyl cyclopentadecan-e-1-one (muscone) a mixture of lactones of the 14-oXy-13-methyltetrade'cane-1-carboxylic acidand 14-oxy-2- methyl-tetradecane-l-carboxylic acid.
- the constitution of the prepared unmethylated lactones was proved by splitting the same by means of boiling potash lye to the corresponding oxyacids which when oxidized'with chromic acid are'transformed into dicarboxylic acids having the same number of carbon atoms.
- lactones have an odorresembling that of musln civet or that of amber and may be employed in place of such perfumes or as raw materials for the preparation of similar products.
- lactones having 14 to 18 ring members represent in itself an important technical progress, as it is very important for the use of a substance as a perfume to remove from the same any impurities which may influence the odor thereof.
- Example 1 27 grams cyclo-pentadecanone (exaltone) are dissolved in gr. petroleum benzine and added with a filtered solution of 160 gr. persulphate of potassium in 400 gr. concentrated sulphuric acid and 74: gr. water, this addition being made so rapidly that the temperature of the mixture remains about degrees centigrade. A too great riseof temperature may be avoided by an exterior cooling with ice. After standing'during several hours the mixture is poured on ice and the layer oi benzine is separated. By shaking the mixture with a solution of soda, acid products are extracted. By treating the neutral portion with a 0 solution of semicarbazide the remaining small quantities of unchanged cyclo-pentadecanone which are contained therein are transformed into the semicarbazone.
- the easily soluble lactone of the l l-oxy-tetradecane-l-carboxylic acid may then be extracted by means of petroleum spirit This lactone boils at 176 degrees centigrade under 15 mm. pressure, solidifies quickly into needles melting at 31 to 32 degrees centigrade and presents the following characteristics:
- D means the density measured at a temperature of 83 degrees Centigrade and relates to water of 4 degrees centigrade;
- Example 3 Cyclo-tetradecanone is treated in the manner described in Example 1. ,After the treatment of the neutral product of reaction with a solution of semicarbazide the lactone of l3-oxy-tridecane-l-carboxylic acid is extracted by means of petroleum spirit. It boils at 165 degrees Centigrade under 15 mm. pressure, melts at 29 to 30 degrees centigrade and presents the following characteristics:
- Example 7 3 methyl-cyclopentadecane-1-on (muscone) is treated in the manner described in Example 1.
- the mixture of the lactencs of the 14-oXy-13-methyl-tetradecane-l-carboxylic acid and 14-oxy-2 methyl-tetradecane-l-carboxylic acid is extracted by means of petroleum spirit.
- the mixture of lactones boils at 180 degrees centigrade at 15 mm. pressure and presents the following characteristics v WVith respect to the number of ring members mentioned in the claims 1 and 2 the following explanation is given:
- the lactone obtained from a ketone possesses one ring member more than the ketone, this ring member being an oxygen atom according to the following formula:
- a process for the preparation of the monocyclic lactones having 14 to 18 ring members consisting in heating monocyclic ketones having 13 to 17 ring members with persulphuri'c acid at a temperature of about 30 to 60 degrees Centigrade.
- a process for the preparationof the lactone from 14-oxy-tetradecane-1-carboxylic acid consisting in dissolving. cyclo-pentadecanone in petroleum benzine. adding a solution of persulphate of. potassium' in sul phuric acid and water, maintaining the temperature atabout 50 degrees centigrade, after several hours standing, pouring the mixture on ice, separatingthe layer of ben zine eX- tracting the acid products by means of a solution of soda, treating the neutral reaction product with a solution of semicarbazide, extracting the lactone of 14-oXy-tetradecane-1- carboxylic acid by means of petroleum spirit. 5.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
cation H. 105,677, Class 12 o,
Patented Apr. 7, .1931
UNITED! STATES PATENT LEoPoLn RUzIcKA, OF DE BILT,
' ANONYME M. NAEF & co., or
LAND
NEAR'UTREGHZIQ, NETHERLANDS, ass anon 'ro SOCIETE GENEVM-SWITZERLAND, A CORPORATION or swrrznn- PROCESS r03 THEPBEPAR-ATION or THE. MONOGYCLIC' nacronns HAVING FOURTEEN i T0. EIGHTEENYRIIIG MEMBERS no Drawing, Application filed. July 16,1928,
Closed; chain lactones: having, more than seven ring members have. not hitherto been obtainable in the pure state: M. Kerschbaum has however stated in the Berichte der deut- 4 5 schen Chemischen Gesellschaft, 1927, volume 60, pages 902 and tollowing,that in native substances a lactone is present having;16' and 17 'ringmembers. It is also stated in the'speciiication of German patent appl published the 25th-May 1927, that synthetic lactones are produced having 16 and 17 ring members, -which are formed by heating with silver oXid of brominated'fatty acids in which the atom of bromine and the carboXyl group are at the opposite, ends of the chain. 'All these lactones-are described as beingliquids whlch do: not possess clearly defined boiling points the yields of these products ln' the syntheti- 20'c'al process are sosmall, that a preparation of the products in the pure state has apparently that now not been possible.-
I have however found that it is possible to obtain such lactones-in the chemically pure stateandin a considerable. yield byheating carbocyclic ketones having a large/number of ring members suchas those descrlbed in the United States Patent 1,673,093 and the United States patent applications Serial No.
.149534- to No, 149,544 now Patents Nos.
1,702,842 to 1,702,852 respectively, issued February 19, 1929, with monopersulphuric acid ata temperature of about 30 to I60 degrees-centigrade.
' 5 l I thus did obtain from cyclotridecan'one the Y 12.-oXy-dodecane-l-carboxylic lactone oi acidjfrom cyclotetradecanone thelactone' of 13-oxy-tridecane 1-carboxylic acid; from ,cyclo-pentadecanone (exaltone) the lactone of 14-oXy-tetradecane-l-carboxylic acid (exaltolid) from cyclo-hexadecanone the lactone of 15-0Xy-pentadecane-l-carboxylic acid and iroin cyclo-heptadecanone (dihydrozibetone) the lactone of 16-oXy-heXadecan-1- 5 carboxylic acid. Allthese lactones are solid at a temperature above 25 degrees centigrade and possess clearly defined boiling ,points, 1
In a similar manner the corresponding lactones can be obtained from alkylated ketones 1 described in: the
U. .S'. Patents 1,673,093,
page. 862.
Serial No. 293,310, and in switzerland'luly 27, 1927.
1,7 02,842 to 1,702,852 inclusively; for instance. from 2-methyl-cyclopenta-decane-lone (lqnethyhexaltone) a mixture of lactones of the 14-oXy-14-methyl-tetradecane-1 carboxylic acid and the 14-oxy-1-methyl-tetradecane-l-carboxylic acid and from 3- methyl cyclopentadecan-e-1-one (muscone) a mixture of lactones of the 14-oXy-13-methyltetrade'cane-1-carboxylic acidand 14-oxy-2- methyl-tetradecane-l-carboxylic acid.
It was however already known to be possible to obtain. lactones having'respectively7 or 8 rmgmembers by treating ketones having 6 or Tringmembers with monopersulphuric' acid, as per Baeyer & Villiger, Berichte der deutschen Chemis-chen Gesellschaft, 1899, volume 32, page 3625 and 1900, volume 33, There appeared however that only such ketones give a good yield of lactones, which possess beside the ketone group substituents such as the isopropyl group and themethyl group. However, ketones which ,besides the keto-group do not possess any substituent did give either no lactone at all oronly a small amount thereof. But then one has to work below 20 degrees centigrade,
as at a higher temperatureonly the splitting product of the lactone, the oXy-acid, is formed. It could therefore not be expected thatketones having a larger number of ring members might give at a higher temperature a yield of more than 50 per cent of pure lactone, even if theypossess lateral chains approaching the keto-group. The stability of 'these' lactones against: warm monopersulphuric acid is so much more remarkable as a smallstability of the'same against hydrolizing agents would rather be expected from the known facility to. form lactones 1 having more than "sevenjring members.
When onthe contrary, the inonopersulphuric acid is allowed to act upon the higher membered ketones under the conditions indicated by v. Baeyer&'Villiger, there is obtained onlyia small quantity of the lactone, and in v its place the peroxide ofthe ketone is formed.
When my working conditions are ,maintained the production of these peroxides is avoided.
The constitution of the prepared unmethylated lactones was proved by splitting the same by means of boiling potash lye to the corresponding oxyacids which when oxidized'with chromic acid are'transformed into dicarboxylic acids having the same number of carbon atoms.
f The herein described lactones have an odorresembling that of musln civet or that of amber and may be employed in place of such perfumes or as raw materials for the preparation of similar products.
The preparation of lactones having 14 to 18 ring members represents in itself an important technical progress, as it is very important for the use of a substance as a perfume to remove from the same any impurities which may influence the odor thereof.
Example 1 27 grams cyclo-pentadecanone (exaltone) are dissolved in gr. petroleum benzine and added with a filtered solution of 160 gr. persulphate of potassium in 400 gr. concentrated sulphuric acid and 74: gr. water, this addition being made so rapidly that the temperature of the mixture remains about degrees centigrade. A too great riseof temperature may be avoided by an exterior cooling with ice. After standing'during several hours the mixture is poured on ice and the layer oi benzine is separated. By shaking the mixture with a solution of soda, acid products are extracted. By treating the neutral portion with a 0 solution of semicarbazide the remaining small quantities of unchanged cyclo-pentadecanone which are contained therein are transformed into the semicarbazone. The easily soluble lactone of the l l-oxy-tetradecane-l-carboxylic acid may then be extracted by means of petroleum spirit This lactone boils at 176 degrees centigrade under 15 mm. pressure, solidifies quickly into needles melting at 31 to 32 degrees centigrade and presents the following characteristics:
D *=0.944l7, n lailof).
D means the density measured at a temperature of 83 degrees Centigrade and relates to water of 4 degrees centigrade;
02 or N means refractive index of the D-line of the spectrum determined at a temperature of 33' degrees centigrade.
Example 2 grees centigrade and presents the following characteristics =O.959O n,', =1.4649.
Example 3 Cyclo-tetradecanone is treated in the manner described in Example 1. ,After the treatment of the neutral product of reaction with a solution of semicarbazide the lactone of l3-oxy-tridecane-l-carboxylic acid is extracted by means of petroleum spirit. It boils at 165 degrees Centigrade under 15 mm. pressure, melts at 29 to 30 degrees centigrade and presents the following characteristics:
D =0.9528; "n =1/l662. Example 4 Cyclo-hexadecanone is treated in the manner described in Example 1. After the treatment of the neutral product of reaction witha solution of semicarbazid the lactone of 15-oxy-pentadecane-l-carboxylic acid is extracted by means of petroleum spirit. It boils at 188 degrees centigrade under 15 mm. pressure, melts at 35 to 36 degrees centigrade and presents the following characteristics:
Example 5 Cyclo-heptadecanone (dihydro-zibetone) is treated in the manner described in EX- ample 1. After the treatment ofthe neutral reaction product with a solution of semicarbazide the lactone of 16-oXy-hexadecane-1- carboxylic acid is extracted by means of petroleum spirit; it boils at 19% degrees centigrade under 15 mm. pressure, melts at 11 to 42 degrees centigrade and presents the following characteristics Dfi =O.9326; 111, 1.4669. Example 6 D =0.93O1; n =1.4611.
Example 7 3 methyl-cyclopentadecane-1-on (muscone) is treated in the manner described in Example 1. After the treatment of the neutral reaction product with a solution of semicarbazide the mixture of the lactencs of the 14-oXy-13-methyl-tetradecane-l-carboxylic acid and 14-oxy-2 methyl-tetradecane-l-carboxylic acid is extracted by means of petroleum spirit. The mixture of lactones boils at 180 degrees centigrade at 15 mm. pressure and presents the following characteristics v WVith respect to the number of ring members mentioned in the claims 1 and 2 the following explanation is given:
By 14 to 18 ring members applicant means that besides the 13 to 17 carbon atoms there is furthermore one oxygen atom which by the conversion of the ketones into the lactones is inserted as ring member. That means in a general manner: 4
The lactone obtained from a ketone possesses one ring member more than the ketone, this ring member being an oxygen atom according to the following formula:
1. A process for the preparation of the monocyclic lactones having 14 to 18 ring members, consisting in heating monocyolic ketones having 13 to 17 ring members with persulphuric acid. 7 i
2. A process for the preparation of the monocyclic lactones having 14 to 18 ring members, consisting in heating monocyclic ketones having 13 to 17 ring members with persulphuri'c acid at a temperature of about 30 to 60 degrees Centigrade.
3. A process for thepreparation of the lactone from 14-oxy-tetradecane-l-carboxylic acid, consisting in heating cyclo-pentadecanone with persulphuric acid.
4. A process for the preparationof the lactone from 14-oxy-tetradecane-1-carboxylic acid, consisting in dissolving. cyclo-pentadecanone in petroleum benzine. adding a solution of persulphate of. potassium' in sul phuric acid and water, maintaining the temperature atabout 50 degrees centigrade, after several hours standing, pouring the mixture on ice, separatingthe layer of ben zine eX- tracting the acid products by means of a solution of soda, treating the neutral reaction product with a solution of semicarbazide, extracting the lactone of 14-oXy-tetradecane-1- carboxylic acid by means of petroleum spirit. 5. The lactone from 14-oxy-tetradecane-1- carboxylic acid boiling at 176 degrees centigrade under 15 mm. pressure, solidifying into needles melting at 31-32 degrees centigrade and presenting the following characteristics: D 0.9447; m 1.4669.
whereof I affix my signature.
' In testimony LEOPOLD RUZICKA.
Publications (1)
Publication Number | Publication Date |
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US1799536A true US1799536A (en) | 1931-04-07 |
Family
ID=3421493
Family Applications (1)
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US1799536D Expired - Lifetime US1799536A (en) | Twvpom |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2844627A (en) * | 1953-03-16 | 1958-07-22 | Celanese Corp | Production of haloacids |
US2903364A (en) * | 1954-12-02 | 1959-09-08 | Margarinbolaget Aktiebolag | Process for improving the taste and flavor of margarine and other foods and edible substances |
US2993056A (en) * | 1956-08-31 | 1961-07-18 | Istituto Sieroterapico Italian | Production of the 1-6-lactone of 6-hydroxy-8-acetoxy-octanoic acid |
-
0
- US US1799536D patent/US1799536A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2844627A (en) * | 1953-03-16 | 1958-07-22 | Celanese Corp | Production of haloacids |
US2903364A (en) * | 1954-12-02 | 1959-09-08 | Margarinbolaget Aktiebolag | Process for improving the taste and flavor of margarine and other foods and edible substances |
US2993056A (en) * | 1956-08-31 | 1961-07-18 | Istituto Sieroterapico Italian | Production of the 1-6-lactone of 6-hydroxy-8-acetoxy-octanoic acid |
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