Reduced color epoxidized esters from epoxidized natural fats and oils

Patent metadata

Field	Value
Publication number	US-9708571-B2
Application number	US-201214125602-A
Country	US
Kind code	B2
Filing date	May 21, 2012
Priority date	Jun 27, 2011
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

Reduced color epoxidized fatty acid esters are provided which may be used as primary plasticizers for PVC, in replacement of phthalate plasticizers. The reduced color epoxidized fatty acid esters are prepared from natural fats or oils by transesterification and interesterification processes, whereby through the use of borohydride, materials having Pt—Co colors according to ASTM D1209 on the order of 50 and lower are possible.

First claim

What is claimed is:

1. A process of making a reduced color epoxidized fatty acid ester from an epoxidized natural fat or oil, comprising the steps of combining an alcohol, an epoxidized natural fat or oil and borohydride with a transesterification catalyst, under conditions which are effective for reacting the alcohol and epoxidized natural fat or oil to form an epoxidized fatty acid ester exhibiting a reduced Pt—Co color, as compared to the epoxidized fatty acid ester that would result from reacting the alcohol and epoxidized natural fat or oil in the presence of the catalyst and under the same conditions but without the use of borohydride.

2. A process according to claim 1 , wherein the borohydride has been pretreated by combination with diglyme before being brought into intimate contact with the catalyst.

3. A process according to claim 1 , wherein the borohydride is present in the reaction mixture at between 0.0001 and 1.0 percent by weight of the total.

4. A process according to claim 3 , wherein the borohydride is between 0.001 percent and 0.1 weight percent of the total.

5. A process according to claim 1 , wherein the borohydride is included in the reaction mixture with the epoxidized natural fat or oil prior to introduction of the catalyst.

6. A process according to claim 1 , wherein the borohydride is included in the reaction mixture concurrently or substantially concurrently with the catalyst.

7. A process according to claim 1 , wherein the Pt—Co color of the reduced color epoxidized fatty acid ester is no more than 80 percent of the Pt—Co color of the ester material that would be produced under the same conditions and using the same catalyst but without using the borohydride.

8. A process according to claim 7 , wherein the Pt—Co color of the product with borohydride is no more than 65 percent of the Pt—Co color that would be produced absent use of borohydride.

9. A process according to claim 7 , wherein the Pt—Co color of the product with borohydride is no more than 50 percent of the Pt—Co color that would be produced absent use of borohydride.

10. A process according to claim 1 , wherein the epoxidized fatty acid ester has a Pt—Co Hazen color of 90 or less as determined by ASTM D1209.

11. A process according to claim 10 , wherein the epoxidized fatty acid ester has a Pt—Co Hazen color of 50 or less as determined by ASTM D1209.

12. A process of making a reduced color epoxidized fatty acid ester or mixture of esters from an epoxidized natural fat or oil, comprising the steps of combining an epoxidized natural fat or oil, a second ester and borohydride with an interesterification catalyst, under conditions which are effective for reacting the second ester and epoxidized natural fat or oil to form an epoxidized fatty acid ester or mixture of esters exhibiting a reduced Pt—Co color, as compared to the epoxidized fatty acid ester or mixture of esters that would result from reacting the second ester and epoxidized natural fat or oil in the presence of the catalyst and under the same conditions but without the use of borohydride.

13. A process according to claim 12 , wherein the borohydride has been pretreated by combination with diglyme before being brought into intimate contact with the catalyst, or wherein the reaction mixture includes a non-nucleophilic alcohol, or wherein both conditions are met.

14. A process according to claim 12 , wherein the borohydride is present in the reaction mixture at between 0.0001 and 1.0 percent by weight of the total.

15. A process according to claim 14 , wherein the borohydride is between 0.001 percent and 0.1 weight percent of the total.

16. A process according to claim 12 , wherein the borohydride is included in the reaction mixture with the epoxidized natural fat or oil prior to introduction of the catalyst.

17. A process according to claim 12 , wherein the borohydride is included in the reaction mixture concurrently or substantially concurrently with the catalyst.

18. A process according to claim 12 , wherein the Pt—Co color of the reduced color epoxidized fatty acid ester or mixture of esters is no more than 80 percent of the Pt—Co color of the ester material that would be produced under the same conditions and using the same catalyst but without using the borohydride.

19. A process according to claim 12 , wherein the Pt—Co color of the product with borohydride is no more than 65 percent of the Pt—Co color that would be produced absent use of borohydride.

20. A process according to claim 12 , wherein the Pt—Co color of the product with borohydride is no more than 50 percent of the Pt—Co color that would be produced absent use of borohydride.

21. A process according to claim 12 , wherein the epoxidized fatty acid ester has a Pt—Co Hazen color of 90 or less as determined by ASTM D1209.

22. A process according to claim 21 , wherein the epoxidized fatty acid ester has a Pt—Co Hazen color of 50 or less as determined by ASTM D1209.

Assignees

• Howard Stephen
• Hagberg Erik
• Poppe George
• Archer Daniels Midland Co

Inventors

• Howard Stephen
• Hagberg Erik
• Poppe George

Classifications

• C07D303/42 Primary

  Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats · CPC title

• C11C3/10 Primary

  Ester interchange · CPC title

• C08K5/10

  Esters; Ether-esters · CPC title

• C11C1/08

  Refining · CPC title

• C11B3/02

  by chemical reaction {(C11B3/003 takes precedence)} · CPC title