Hydrolysis of methyl esters in dimethylsulfoxide for production of fatty acids
| Title: | Hydrolysis of methyl esters in dimethylsulfoxide for production of fatty acids |
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| Patent Number: | 5,440,061 |
| Publication Date: | August 08, 1995 |
| Appl. No: | 08/219,066 |
| Application Filed: | March 29, 1994 |
| Abstract: | The present invention relates to an improved process for preparing fatty acids from alkyl, preferably methyl esters comprising mixing the fatty acid ester with water, acid catalyst, and DMSO in order to form a single phase reaction mixture. The single phase reaction mixture is then heated to a temperature of from about 70.degree. C. to about 130.degree. C. to hydrolyze the fatty acid ester into the corresponding acid and volatile alcohol and removing the volatile alcohol. The acid catalyst is heat and water stable and the reaction mixture is essentially free of C.sub.2 -C.sub.5 carboxylic acids. The initial stoichiometric ratio of the water to the ester is at least about 1:1. |
| Inventors: | Gibson, Michael S. (Loveland, OH) |
| Assignees: | The Procter & Gamble Company (Cincinnati, OH) |
| Claim: | What is claimed is |
| Claim: | 1. A process for the production of fatty acids comprising the following steps |
| Claim: | (a) mixing fatty acid ester of a volatile alcohol with water, acid catalyst, and DMSO to form a single phase reaction mixture; and |
| Claim: | (b) heating the single phase reaction mixture to a temperature of from about 70.degree. C. to about 130.degree. C. to hydrolyze said fatty acid ester into the corresponding acid and volatile alcohol and removing said volatile alcohol; |
| Claim: | wherein the acid catalyst is heat and water stable; wherein the reaction mixture is essentially free of C.sub.2 -C.sub.5 carboxylic acids; and wherein the initial stoichiometric ratio of water to ester is at least about 1:1 on a molar basis. |
| Claim: | 2. The process of claim 1 wherein the temperature in step (b) is from about 95.degree. C. to about 130.degree. C. |
| Claim: | 3. The process of claim 1 wherein the single phase reaction mixture is agitated. |
| Claim: | 4. The process of claim 1 wherein the acid catalyst is benzene sulfonic acid or linear alkyl benzene sulfonic acid of the formula: ##STR6## wherein R.sup.3 is an alkyl chain having from 1 to about 20 carbon atoms, and mixtures thereof. |
| Claim: | 5. The process of claim 1 wherein the temperature in step (b) is from about 95.degree. C. to about 130.degree. C. |
| Claim: | 6. The process of claim 1 wherein the amount of fatty acid ester present in the reaction is from about 15% to about 40% by weight of the reaction mixture, the amount of acid catalyst present in the reaction is from about 0.1% to about 40% by weight of the reaction mixture, the amount of DMSO present in the reaction is from about 40% to about 80% by weight of the reaction mixture, and the amount of water present in the reaction is from about 10% to about 25% by weight of the reaction mixture. |
| Claim: | 7. The process of claim 6 wherein the single phase reaction mixture is agitated. |
| Claim: | 8. The process of claim 6 wherein the acid catalyst is benzene sulfonic acid or linear alkyl benzene sulfonic acid of the formula: ##STR7## wherein R.sup.3 is an alkyl chain having from 1 to about 20 carbon atoms, and mixtures thereof. |
| Claim: | 9. The process of claim 5 wherein the amount of fatty acid present in the reaction is from about 8% to about 38% by weight of the reaction mixture, the amount of acid catalyst present in the reaction is from about 0.3% to about 20% by weight of the reaction mixture, the amount of DMSO present in the reaction is from about 40% to about 75% by weight of the reaction mixture, and the amount of water present in the reaction is from about 11% to about 20% by weight of the reaction mixture. |
| Claim: | 10. The process of claim 9 wherein the temperature in step (b) is from about 95.degree. C. to about 130.degree. C. |
| Claim: | 11. The process of claim 9 wherein the single phase reaction mixture is agitated. |
| Claim: | 12. The process of claim 9 wherein the acid catalyst is benzene sulfonic acid or linear alkyl benzene sulfonic acid of the formula: ##STR8## wherein R.sup.3 is an alkyl chain having from 1 to about 20 carbon atoms, and mixtures thereof. |
| Claim: | 13. The process of claim 9 wherein the amount of fatty acid present in the reaction is from about 10% to about 37% by weight of the reaction mixture, the amount of acid catalyst present in the reaction is from about 0.5% to about 15% by weight of the reaction mixture, the amount of DMSO present in the reaction is from about 44% to about 70% by weight of the reaction mixture, and the amount of water present in the reaction is from about 11% to about 17% by weight of the reaction mixture. |
| Claim: | 14. The process of claim 13 wherein the temperature in step (b) is from about 95.degree. C. to about 130.degree. C. |
| Claim: | 15. The process of claim 13 wherein the single phase reaction mixture is agitated. |
| Claim: | 16. The process of claim 14 wherein the acid catalyst is benzene sulfonic acid or linear alkyl benzene sulfonic acid of the formula: ##STR9## wherein R.sup.3 is an alkyl chain having from 1 to about 20 carbon atoms, and mixtures thereof. |
| Claim: | 17. The process of claim 16 wherein R.sup.3 is an alkyl group with from about 6 to about 14 carbon atoms, and mixtures thereof. |
| Claim: | 18. The process of claim 17 wherein R.sup.3 is an alkyl group having from about 11 to about 13 carbon atoms, and mixtures thereof. |
| Claim: | 19. The process of claim 18 wherein the R.sup.3 group is attached to the benzene ring at the middle one-half of the alkyl chain. |
| Claim: | 20. The process of claim 1 wherein the acid catalyst is sulfuric acid. |
| Claim: | 21. The process of claim 1 wherein said fatty acid ester has the formula: ##STR10## wherein R is a saturated or unsaturated aliphatic chain having from about 4 to about 19 carbon atoms, and R.sup.2 is a saturated or unsaturated aliphatic chain having from about 1 to about 4 carbon atoms. |
| Claim: | 22. The process of claim 21 wherein R is from about 4 to about 13 carbon atoms, and R.sup.2 is from about 1 to about 2 carbon atoms. |
| Claim: | 23. The process of claim 22 wherein R is from about 5 to about 11 carbon atoms, and R.sup.2 is a methyl group. |
| Claim: | 24. The process of claim 1 wherein the acid catalyst is recovered from the reaction mixture by the following steps |
| Claim: | (a) distilling the unreacted water, alcohol, DMSO and unreacted ester under vacuum; and |
| Claim: | (b) distilling the fatty acid product away from the product of (a) under vacuum. |
| Claim: | 25. The process of claim 24 wherein the temperature does not exceed about 163.degree. C. for reaction mixtures containing esters of C.sub.8 -C.sub.12 fatty acids. |
| Claim: | 26. The process of claim 25 wherein the temperature does not exceed about 150.degree. C. |
| Current U.S. Class: | 554/160; 554/161; 554/163; 554/154 |
| Current International Class: | C07C 51377 |
| Patent References Cited: | 4073799 February 1978 Kondo et al. 4185027 January 1980 Logan 4335263 June 1982 Minai 4406833 September 1983 Boehme et al. 4981966 January 1991 Hermecz et al. 4996098 February 1991 Perusich et al. 5091530 February 1992 Hermecz et al. 5128070 July 1992 Sedelies et al. |
| Primary Examiner: | Dees, Jose G. |
| Assistant Examiner: | Carr, Deborah D. |
| Attorney, Agent or Firm: | Lewis, Beth Goldstein |
| Accession Number: | edspgr.05440061 |
| Database: | USPTO Patent Grants |
| Language: | English |
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