Method for purifying alcohol esters

• US 5,424,467 A
• Filed: 07/14/1993
• Issued: 06/13/1995
• Est. Priority Date: 07/14/1993
• Status: Expired due to Term

• Current Assignee: Idaho Research Foundation, Inc.
• Original Assignee: Idaho Research Foundation, Inc.
• Inventors: Bam, Narendra, Korus, Roger, Drown, David C., Hoffman, Dwight S., Washam, Jacqueline M., Johnson, Timothy G.
• Primary Examiner(s): Dees, Jose G.
• Assistant Examiner(s): Carr, Deborah D.
• Application Number:
  US08/092,198
• Time in Patent Office: 699 Days
• Field of Search: 554/206, 554/169, 554/216
• US Class Current: 554/216
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 69/24 esterified with monohydroxylic 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: C10L 1/026 for compression ignition
• CPC Class Codes: C11C 3/04 by esterification of fats or fatty oils
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel

Abstract

Triglycerides, such as vegetable oils and animal fats, are esterified with alcohols to produce alcohol esters which can be used as alternative fuel sources. By-products of the transesterification reaction are stripped from the effluent of the transesterification reactor using a recovery alcohol that can be an isolated by-product of the transesterification reaction.

Claims

1. A method for purification of an alcohol ester of a triglyceride produced by a transesterification reaction between an alcohol and the triglyceride, the transesterification reaction occurring in the presence of a catalyst, the method comprising the steps:

separating a first phase including the alcohol ester, unreacted alcohol, and catalyst from a second phase including a by-product alcohol, unreacted alcohol and catalyst;

treating the second phase to separate the by-product alcohol from the unreacted alcohol and catalyst;

treating the first phase with the separated by-product alcohol to separate the catalyst from the alcohol ester.

2. The method of claim 1, wherein treating the first phase also separates unreacted alcohol from the alcohol ester.

3. The method of claim 1, wherein treating the first phase further provides a collected mixture of unreacted alcohol and catalyst from the first phase and by-product alcohol.

4. The method of claim 3, further comprising the step of combining the second phase with the collected mixture from the step of treating the first phase,. and then treating the combination of the second phase and collected mixture to separate by-product alcohol from the untreated alcohol and catalyst.

5. The method of claim 3, wherein the collected mixture is treated to separate by-product alcohol from the unreacted alcohol, the method further comprising the step of recycling the unreacted alcohol separated from the by-product alcohol to the transesterification reaction.

6. The method of claim 5, wherein the unreacted alcohol is separated from the by-product alcohol by distillation.

7. The method of claim 5, wherein the by-product alcohol separated from the unreacted alcohol includes organic residue and catalyst, the method further comprising the step of separating the organic residue and the catalyst from the by-product alcohol after the by-product alcohol has been separated from the unreacted alcohol.

8. The method of claim 7, further comprising the step of oxidizing the organic residue and the catalyst separated from the by-product alcohol.

9. The method of claim 1, wherein treating the second phase comprises distilling the second phase.

10. The method of claim 1, further comprising the step of recycling by-product alcohol containing unspent catalyst to a vessel wherein the transesterification reaction is carried out.

11. The method of claim 1, wherein the by-product alcohol is glycerin.

12. The method of claim 1, further comprising the step of contacting the second phase with additional unreacted alcohol to produce additional alcohol ester and by-product alcohol.

13. The method of claim 1, further comprising the step wherein the second phase is heated to produce additional alcohol ester and by-product alcohol.

19. The method of claim 1, wherein the unreacted alcohol separated from the by-product alcohol during treating of the second phase is recycled to the transesterification reaction.

20. The method of claim 19, wherein the by-product alcohol separated from the unreacted alcohol includes organic residue and catalyst, the method further comprising the step of separating the organic residue and the catalyst from the by-product alcohol after the by-product alcohol has been separated from the unreacted alcohol.

21. The method of claim 20, further comprising the step of oxidizing the organic residue and the catalyst separated from the by-product alcohol.

24. The method of claim 1, wherein the second phase further comprises water, the method further comprising the step of separating the water from the by-product alcohol of the second phase.

14. A method for the recovery of by-products from a transesterification reaction between an alcohol and a triglyceride in the presence of a catalyst, the method comprising the steps:

separating a first phase including an alcohol ester of the triglyceride, first phase unreacted alcohol, and first phase catalyst from a second phase including a by-product alcohol, second phase unreacted alcohol and second phase catalyst;

separating the second phase unreacted alcohol from the by-product alcohol and the second phase catalyst;

separating the by-product alcohol from the second phase catalyst;

treating the first phase with the by-product alcohol separated from the second phase catalyst to separate the first phase unreacted alcohol and the first phase catalyst from the alcohol ester and provide a mixture of the by-product alcohol, first phase unreacted alcohol, and the first phase catalyst;

combining the mixture of the by-product alcohol, first phase unreacted alcohol and first phase catalyst with the second phase after it is separated from the first phase; and

separating the combined mixture into streams of by-product alcohol, first and second phase unreacted alcohol, and first and second phase catalyst.

25. The method of claim 14, wherein the second phase further comprises water, the method further comprising the step of separating the water from the by-product alcohol of the second phase.

15. A method for purification of an alcohol ester of a triglyceride produced by a transesterification reaction between an alcohol and the triglyceride, the transesterification reaction occurring in the presence of a catalyst, the method comprising the steps:

separating a first phase including the alcohol ester, unreacted alcohol, and catalyst from a second phase including a by-product alcohol, unreacted alcohol, and catalyst;

treating the first phase with a recovery alcohol to separate the catalyst from the alcohol ester.

16. The method of claim 15, wherein the recovery alcohol is glycerin.

17. A method for the recovery of by-products from a transesterification reaction between an alcohol and a triglyceride in the presence of a catalyst, the method comprising the steps:

separating a first phase including an alcohol ester of the triglyceride, first phase unreacted alcohol, and first phase catalyst from a second phase including a by-product alcohol, second phase unreacted alcohol and second phase catalyst;

treating the first phase with a recovery alcohol to separate the first phase unreacted alcohol and the first phase catalyst from the alcohol ester and provide a mixture of the recovery alcohol, first phase unreacted alcohol, and the first phase catalyst; and

separating at least one component from the mixture of the recovery alcohol, first phase unreacted alcohol, and the first phase catalyst.

18. The method of claim 17, wherein the recovery alcohol is glycerin.

26. The method of claim 17, wherein the second phase further comprises water, the method further comprising the step of separating the water from the by-product alcohol of the second phase.

22. A method for the recovery of by-products from a transesterification reaction between an alcohol and a triglyceride in the presence of a catalyst, the method comprising the steps:

separating a first phase including an alcohol ester of the triglyceride, first phase unreacted alcohol, and first phase catalyst from a second phase including a by-product alcohol, second phase unreacted alcohol and second phase catalyst.

treating the first phase with a recovery alcohol to separate the first phase unreacted alcohol and the first phase catalyst from the alcohol ester and provide a mixture of the recovery alcohol, first phase unreacted alcohol, and the first phase catalyst; and

separating at least one component from the by-product alcohol, second phase unreacted alcohol and second phase catalyst that form the second phase.

23. The method of claim 22, wherein the recovery alcohol is glycerin.

27. The method of claim 22, wherein the second phase further comprises water, the method further comprising the step of separating the water from the by-product alcohol of the second phase.

28. A method for purification of an alcohol ester comprising the step:

treating the alcohol ester with a recovery alcohol to extract impurities from the alcohol ester into the recovery alcohol.

29. The method of claim 28, wherein the recovery alcohol is glycerin.