Preparation of poly alpha-1,3-glucan esters and films therefrom
View Patent ↗Poly alpha-1,3-glucan ester compounds are disclosed herein with a degree of substitution of about 0.05 to about 3.0. Also disclosed are methods of producing poly alpha-1,3-glucan ester compounds and films made therefrom.
1. A composition comprising a poly alpha-1,3-glucan ester compound represented by the structure:
wherein
(i) n is at least 6,
(ii) each R is independently an H or acyl group, and
(iii) the compound has a degree of substitution by the acyl group of less than 2.75.
2. The composition of claim 1 , wherein at least one acyl group is selected from the group consisting of acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, and octanoyl.
3. The composition of claim 1 , wherein the compound contains one type of acyl group.
4. The composition of claim 1 , wherein the compound contains two or more types of acyl group.
5. The composition of claim 4 , wherein the two or more types of acyl group are:
(i) acetyl and propionyl, or
(ii) acetyl and butyryl.
6. The composition of claim 1 , wherein the compound has a degree of substitution by the acyl group of about 0.05 to about 2.70.
7. The composition of claim 6 , wherein at least one acyl group is selected from the group consisting acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, and octanoyl.
8. The composition of claim 6 , wherein the compound contains one type of acyl group.
9. The composition of claim 8 , wherein the acyl group is an acetyl group.
10. The composition of claim 9 , wherein the compound has a degree of substitution by the acetyl group of about 0.05 to about 2.60.
11. The composition of claim 6 , wherein the compound contains two or more types of acyl group.
12. The composition of claim 11 , wherein the two or more types of acyl group are:
(i) acetyl and propionyl, or
(ii) acetyl and butyryl.
13. A method of producing a poly alpha-1,3-glucan ester compound, the method comprising:
(a) contacting poly alpha-1,3-glucan in a reaction that is substantially anhydrous with at least one acid catalyst, at least one acid anhydride, and at least one organic acid, wherein at least one acyl group is esterified to the poly alpha-1,3-glucan thereby producing a poly alpha-1,3-glucan ester compound represented by the structure:
wherein
(i) n is at least 6,
(ii) each R is independently an H or acyl group, and
(iii) the compound has a degree of substitution by the acyl group of less than 2.75; and
(b) optionally, isolating the poly alpha-1,3-glucan ester compound produced in step (a).
14. The method of claim 13 , wherein the compound has a degree of substitution by the acyl group of about 0.05 to about 2.70.
15. The method of claim 13 , wherein the acid catalyst comprises sulfuric acid.
16. The method of claim 13 , wherein:
the acid anhydride is one or more of acetic anhydride, propionic anhydride, or butyric anhydride; and
the organic acid is one or more of acetic acid, propionic acid, or butyric acid.
17. The method of claim 13 , wherein the poly alpha-1,3-glucan is further contacted with an organic solvent in step (a).
18. The method of claim 13 , wherein the compound contains one type of acyl group.
19. The method of claim 18 , wherein the acyl group is an acetyl group.
20. The method of claim 13 , wherein the percentage of glycosidic linkages of the poly alpha-1,3-glucan ester compound that are alpha-1,3 is at least 90%.
21. The method of claim 20 , wherein the percentage of glycosidic linkages of the poly alpha-1,3-glucan ester compound that are alpha-1,3 is 100%.
22. The composition of claim 1 , wherein the percentage of glycosidic linkages of the poly alpha-1,3-glucan ester compound that are alpha-1,3 is at least 90%.
23. The composition of claim 22 , wherein the percentage of glycosidic linkages of the poly alpha-1,3-glucan ester compound that are alpha-1,3 is 100%.
24. The composition of claim 3 , wherein the acyl group is an acetyl group.