Low-color ester compositions and methods of making and using the same
View Patent ↗Low-color ester compositions and methods of making low-color ester compositions are generally disclosed. In certain embodiments, methods of making low-color ester compositions from a biorefinery bottoms stream are disclosed. In some other embodiments, methods for recovering esters of 1,18-octadecanedioic acid are disclosed.
1. A method of removing colored impurities from a fatty acid ester composition, the method comprising:
providing a fatty acid ester composition, the composition comprising (a) one or more esters of monobasic fatty acids, (b) one or more esters of dibasic fatty acids, and (c) one or more chromophoric impurities; and
chemically treating the fatty acid ester composition to reduce the concentration of at least one of the one or more chromophoric impurities.
2. The method of claim 1 , wherein the monobasic fatty acids are C 12-24 monobasic fatty acids.
3. The method of claim 1 , wherein the monobasic fatty acids are palmitic acid, stearic acid, or mixtures thereof.
4. The method of claim 1 , wherein the one or more esters of monobasic fatty acids are glyceryl esters of monobasic fatty acids.
5. The method of claim 1 , wherein the one or more esters of monobasic fatty acids are C 1-12 alkyl esters of monobasic fatty acids.
6. The method of claim 5 , wherein the C 1-12 alkyl esters of monobasic fatty acids are methyl esters of monobasic fatty acids.
7. The method of claim 1 , wherein the dibasic fatty acids are C 12-24 dibasic fatty acids.
8. The method of claim 7 , wherein the dibasic fatty acids are octadecanedioic acid, heneicosanedioic acid, or mixtures thereof.
9. The method of claim 8 , wherein the one or more esters of dibasic fatty acids are glyceryl esters of dibasic fatty acids.
10. The method of claim 8 , wherein the one or more esters of dibasic fatty acids are C 1-12 alkyl esters of dibasic fatty acids.
11. The method of claim 10 , wherein the C 1-12 alkyl diesters of dibasic fatty acids are methyl diesters of dibasic fatty acids, ethyl diesters of dibasic fatty acids, isopropyl diesters of dibasic fatty acids, or mixtures thereof.
12. The method of claim 11 , wherein the C 1-12 alkyl diesters of dibasic fatty acids are methyl diesters of dibasic fatty acids.
13. The method of claim 1 , wherein the chromophoric impurity is a tetraterpenoid.
14. The method of claim 13 , wherein the chromophoric impurity is a xanthophyll, a carotene, or a mixture thereof.
15. The method of claim 1 , wherein the chemically treating comprises contacting the fatty acid ester composition with a decolorizing composition.
16. The method of claim 15 , wherein the decolorizing composition is an aqueous composition, which comprises one or more anionic oxidizing agents.
17. The method of claim 16 , wherein the one or more anionic oxidizing agents comprise chlorite anions (ClO 2 − ), persulfate anions (S 2 O 8 2− , or a combination thereof.
18. The method of claim 15 , wherein the chemically treating comprises contacting the fatty acid ester composition with a first decolorizing composition and a second decolorizing composition, the first and second decolorizing compositions being aqueous compositions that comprise one or more anionic oxidizing agents.
19. The method of claim 18 , wherein the first decolorizing composition comprises chlorite anions (ClO 2 − ).
20. The method of claim 18 , wherein the second decolorizing composition comprises persulfate anions (S 2 O 8 2− ).