Process for the preparation of esters

• US 4,956,286 A
• Filed: 12/21/1987
• Issued: 09/11/1990
• Est. Priority Date: 12/19/1986
• Status: Expired due to Fees

• Current Assignee: Unilever Patent Holdings BV (Unilever PLC)
• Original Assignee: Unilever Patent Holdings BV (Unilever PLC)
• Inventors: Macrae, Alasdair R.
• Primary Examiner(s): Griffin, Ronald W.
• Assistant Examiner(s): Webber, Pamela S.
• Application Number:
  US07/135,355
• Time in Patent Office: 995 Days
• Field of Search: 435/134, 435/198, 435/271
• US Class Current: 435/134
• CPC Class Codes: C11C 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: C11C 3/04 by esterification of fats or fatty oils
• CPC Class Codes: C12P 7/62 Carboxylic acid esters
• CPC Class Codes: C12P 7/6436 Fatty acid esters
• CPC Class Codes: C12P 7/6454 by esterification

Abstract

The invention provides a process for preparing an ester from an alcohol and fatty acid (glyceride) by enzyme-catalyzed conversion, in which a fatty acid (glyceride) and alcohol are contacted with lipase and the alcohol is added at such a rate that the alcohol concentration in the reaction mixture is kept below a molar ratio of 0.5 moles of alcohol per mole of fatty acid/acyl group, preferably below 0.25. The alcohol is a C₁ -C₈ alcohol, preferably a monohydric alcohol. The fatty acid is a C₂ -C₂₄ fatty acid, preferably a C₁₀ -C₂₄ fatty acid. Preferably, water of reaction is removed while esterification progresses.

Claims

1. In a process for preparing an ester from an alcohol and fatty acid or glyceride thereof by enzyme-catalyzed conversion, the improvement which comprises mixing the fatty acid or glyceride thereof with a lipase catalyst and adding the alcohol to said mixture at such a rate that the alcohol concentration in the reaction mixture is kept below a molar ratio of 0.5 moles of alcohol per mole of fatty acid/acyl group whereby the rate of ester formation is increased.

2. A process according to claim 1, wherein the alcohol is added at such a rate that the molar ratio of alcohol to fatty acid/acyl group is below 0.25.

3. A process according to claim 1, wherein the alcohol is a C₁ -C₈ alcohol.

4. A process according to claim 3, wherein the alcohol is a monohydric alcohol.

5. A process according to claim 1, wherein the fatty acid is a C₂ -C₂₄ fatty acid.

6. A process according to claim 1, wherein the fatty acid glyceride is a triglyceride derived from C₁₀ -C₂₄ fatty acids.

7. A process according to claim 5, wherein water of reaction is removed while esterification progresses.

8. A process according to claim 7, wherein said water is removed by dipping a cold surface in the gaseous phase of the reaction vessel.

9. A process according to claim 1, wherein the ester is prepared in the presence of water.

10. A process according to claim 7, wherein said water is removed by distillation.

11. A process according to claim 1 wherein the acid or glyceride thereof is oleic acid, butter oil or coconut oil and the alcohol is ethanol or propanol.