Process for producing lower alcohol esters of fatty acids

• US 4,164,506 A
• Filed: 03/09/1978
• Issued: 08/14/1979
• Est. Priority Date: 03/17/1977
• Status: Expired due to Term

• Current Assignee: Kao Soap Co., Ltd. (KAO Corporation)
• Original Assignee: Kao Soap Co., Ltd. (KAO Corporation)
• Inventors: Kawahara, Yoshiharu, Ono, Toshio
• Primary Examiner(s): Niebling, John F.
• Application Number:
  US05/884,835
• Time in Patent Office: 523 Days
• Field of Search: 260/410, 260/410.9 R, 260/410.9 E, 260/421
• US Class Current: 554/167
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 67/08 by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• CPC Class Codes: C07C 69/52 Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
• CPC Class Codes: C10G 2300/1003 Waste materials
• CPC Class Codes: C10G 2300/1011 Biomass
• CPC Class Codes: C10G 2400/04 Diesel oil
• CPC Class Codes: C11B 3/02 by chemical reaction C11B3/003 takes precedence
• 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: Y02P 30/20 using bio-feedstock

Abstract

Lower alcohol esters of fatty acids are produced by esterifying free fatty acids of unrefined fats with a lower alcohol in an amount larger than its solubility in the fats in the presence an acid catalyst; separating the product mixture into the fat layer and the lower alcohol layer, so that the latter may be removed out; and then effecting the interesterification reaction between the resulting, refined fats and a lower alcohol with an alkali catalyst.

Claims

1. A process for producing lower alcohol esters of fatty acids from an unrefined fat containing impurities including free fatty acids, polypeptides and phospholipids, which comprises the steps of:

(1) reacting the free fatty acids of said unrefined fat with a lower alcohol, in the presence of an acid catalyst, to esterify said free fatty acids, the amount of said lower alcohol present in the reaction mixture at the end of the esterification reaction being an amount greater than the amount of said lower alcohol that can be dissolved in said fat whereby, at the end of the esterification reaction, the reaction mixture contains a fat phase and a lower alcohol phase, said lower alcohol phase containing impurities dissolved therein;

(2) then separating said reaction mixture into a fat layer and a lower alcohol layer, removing said lower alcohol layer and thereby obtaining refined fat;

(3) then adding a lower alcohol and an alkali catalyst to said refined fat and effecting an interesterification reaction to form lower alcohol esters of the fatty acids in said refined fat, and then recovering said lower alcohol esters.

2. A process as claimed in claim 1, in which in step (1), the esterification of the free fatty acids is effected at 60°

to 120°

C.

3. A process as claimed in claim 1, in which said lower alcohol has from one to three carbon atoms.

4. A process as claimed in claim 1, in which said lower alcohol is methyl alcohol.

5. A process as claimed in claim 1, in which in step (1), the esterification of the free fatty acids is effected at 65°

to 70°

C.

6. A process as claimed in claim 1, in which in step (1) the amount of said lower alcohol present during the esterification reaction is greater than the amount of said lower alcohol that can be dissolved in said unrefined fat.

7. A process as claimed in claim 1, in which the step (1), after completion of the esterification reaction, an additional quantity of said lower alcohol is added to the reaction mixture so that the amount of said lower alcohol present in the reaction mixture is greater than the amount of said lower alcohol that can be dissolved in said unrefined fat.

8. A process as claimed in claim 1, in which after step (2) and prior to step (3), an additional quantity of said lower alcohol is admixed with said fat wherein said quantity is an amount greater than the amount of said lower alcohol that can be dissolved in said fat, then allowing the mixture thereby formed to stand to separate same into a fat layer and a lower alcohol layer, then removing said lower alcohol layer and using said fat layer in step (3).

9. A process as claimed in claim 8, in which said steps of admixing said additional quantity of said lower alcohol, allowing the mixture thereby formed to separate and then removing said lower alcohol layer, are repeated at least once, and the fat layer finally obtained is then used in step (3).

10. A process as claimed in claim 8, in which said lower alcohol has one to three carbon atoms.

11. A process as claimed in claim 8, in which said lower alcohol is methyl alcohol.

12. A process as claimed in claim 4, in which the amount of methanol used in step (1) is from 20 to 30% by weight, based on the weight of the fat.

13. A process as claimed in claim 1, in which in step (1) the amount of said lower alcohol present at the start of the esterification reaction is greater than the amount of said lower alcohol that can be dissolved in said unrefined fat, during the esterification reaction distilling out water and said lower alcohol and simultaneously blowing in an additional quantity of said lower alcohol at the same rate at which said lower alcohol is being distilled out of the reaction mixture.