Process for the production of ethyl esters

• US 6,013,817 A
• Filed: 05/07/1997
• Issued: 01/11/2000
• Est. Priority Date: 05/07/1996
• Status: Expired due to Term

• Current Assignee: Institut Francais Du Petrole
• Original Assignee: Institut Francais Du Petrole
• Inventors: Stern, Robert, Eisa, Mohammed Neguib, Hillion, Gerard
• Primary Examiner(s): Killos, Paul J.
• Assistant Examiner(s): PARSA, JAFAR F
• Application Number:
  US08/852,737
• Time in Patent Office: 979 Days
• Field of Search: 554/167
• US Class Current: 554/167
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• 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: 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: C11C 3/10 Ester interchange

Abstract

For the production of ethyl esters of fatty acids from fatty acid glycerides such as vegetable or animal oil or fat or other mixtures of glycerides, the process comprises the following stages: (a) transesterifying fatty acid glycerides with hydrated ethyl alcohol using an alkaline catalyst to form a medium comprising ethyl esters and excess ethyl alcohol; (b) adding a glycerine phase to said medium, and evaporating the excess ethyl alcohol to produce two immiscible phases, an ester phase and a glycerine phase A, and recycling said excess ethyl alcohol to stage (a); (c) separating said glycerine phase A and said ester phase to obtain the desired ethyl esters; (d) neutralizing said glycerine phase A with acid, and separating resultant "fatty acids+esters" phase and a glycerine phase B, and drying the latter phase; (e) subjecting the "fatty acids+esters" phase to glycerolysis with at least a fraction of the dried glycerine phase B in the presence of an alkaline catalyst to form a mixture of glycerides and esters, and passing said mixture into transesterification stage (a).

Claims

1. A process for the production of ethyl esters of fatty acids from a fatty acid glycerides starting substance selected from the group consisting of vegetable oil, animal oil, fat and or mixtures of glycerides, the process comprising the following stages:

(a) transesterifying the fatty acid glyceride starting substance with hydrated ethyl alcohol at a temperature of 5 to 50°

C. using an alkaline catalyst to form a medium comprising ethyl esters and excess ethyl alcohol said hydrated ethyl alcohol having an ethyl alcohol content of 92 to 99% by weight and being in a proportion of 30-100% by weight with respect to the starting substance;

(b) adding a glycerine phase to said medium, and evaporating the excess ethyl alcohol to produce two immiscible phases, an ester phase and a glycerine phase A, and recycling said excess ethyl alcohol to stage (a), said excess ethyl alcohol having an ethyl alcohol content at least equal to the alcohol content of the hydrated ethyl alcohol used in step (a);

(c) separating said glycerine phase A and said ester phase to obtain the desired ethyl esters;

(d) neutralizing said glycerine phase A with acid, and separating resultant "fatty acids+esters" phase and a glycerine phase B, and drying the latter phase; and

(e) subjecting the "fatty acids+esters" phase to glycerolysis with at least a fraction of the dried glycerine phase B in the presence of an alkaline catalyst to form a mixture of glycerides and esters, and passing said mixture into transesterification stage (a).

2. A process according to claim 1, wherein, computed relative to the starting substance the alkaline catalyst corresponds to 1 to 2% by weight of soda to the fatty acid glyceride starting substance, and a proportion of 30 to 100% by weight of hydrated ethyl alcohol and a proportion of 30 to 100% by weight of hydrated ethyl alcohol.

3. A process according to claim 1, wherein the hydrated ethyl alcohol that is used exhibits an alcohol content of 94 to 97% by weight and is used at a proportion of 40 to 60% by weight relative to the starting oil.

4. A process according to claim 1, wherein the glycerine phase that is used in stage (b) is a fraction of glycerine phase B that is obtained in stage (d), dried to a temperature of about 150°

C.

5. A process according to claim 4, wherein said glycerine phase contains 1 to 20% water and is used at a proportion of 20 to 40% relative to the starting oil.

6. A process according to claim 1, wherein the glycerolysis reaction of stage (e) is carried out at a temperature of 170 to 220°

C., catalyzed with a fraction of basic glycerine phase A that is separated in stage (c) and is continued until a product is obtained whose acid number is less than 2.

7. A process according to claim 1, wherein the product that is obtained at the end of stage (e) is, after filtration, recycled to the oil, the fat, or the starting mixture of glycerides or to stage (a).

8. A process according to claim 5, wherein the glycerolysis reaction of stage (e) is carried out at a temperature of 170 to 220°

C., catalyzed with a fraction of basic glycerine phase A that is separated in stage (c) and is continued until a product is obtained whose acid number is less than 2.

9. A process according to claim 8, wherein the product that is obtained at the end of stage (e) is, after filtration, recycled to the oil, the fat, or the starting mixture of glycerides or to stage (a).

10. A process according to claim 1, wherein said fatty acid glyceride starting substances are not subjected to any acidic transesterification step prior to step(a).

17. A process according to claim 1, wherein said alkaline catalyst is an alkaline alcoholate.

11. In a process for the production of ethyl esters of fatty acids from a starting substance selected from the group consisting of vegetable or animal oil fat, and mixtures of glycerides, the improvement comprising transesterifying the starting substance with a hydrated ethyl alcohol having a content of 92 to 99% by weight of ethyl alcohol, said hydrated ethyl alcohol being in a proportion of 30 to 100% by weight of ethyl alcohol with respect to the starting substance, said transesterifying being conducted in the presence of an alkaline catalyst and at a temperature of 5 to 50°

C., evaporating the excess ethyl alcohol and separating the resultant glycerine and ethyl esters.

12. A process according to claim 11, wherein said fatty acid glyceride starting substances are not subjected to any acidic transesterification step prior to step(a).

13. A process according to claim 11, wherein, computed relative to the starting substance the alkaline catalyst corresponds to 1 to 2% by weight of soda to the fatty acid glyceride starting substance.

14. A process according to claim 11, wherein the hydrated ethyl alcohol that is used exhibits an alcohol content of 94 to 97% by weight and is used at a proportion of 40 to 60% by weight relative to the starting substance oil.

15. A process according to claim 11, wherein said transesterifying stage (a) is conducted at between 20°

and 50°

C.

16. A process according to claim 11, wherein said process consists essentially of said stages.

18. A process according to claim 11, wherein said alkaline catalyst is an alkaline alcoholate.