Aromatic polyesters from biosuccinic acid
Biosuccinic acid, obtained via sugar fermentation, is cyclodimerized and oxidized to yield building blocks for aromatic polyesters with high glass transition temperatures.
1. A polymer comprising a plurality of monomers having the structure:
wherein n may be from 1 to 20, and wherein R 1 and R 2 may be independently selected from hydrogen or a C 1 -C 6 hydrocarbon subtituent.
2. The polymer according to claim 1 , wherein the polymer is a copolymer, possessing additional repeat units.
3. The polymer according to claim 1 , wherein the polymer is a polyalkylene dihydroxyterephthalate, having the structure:
4. The polymer according to claim 3 , wherein the polymer has a number average molecular weight in a range of from about 5,000 to about 500,000.
5. The polymer according to claim 3 , wherein the polymer has a weight average molecular weight in a range of from about 10,000 to about 1,000,000.
6. The polymer according to claim 3 , wherein the polymer has a dispersity in a range of from about 1.1 to about 10.
7. The polymer according to claim 3 , wherein the polymer has a glass transition temperature in a range of from about 30 to about 180° C.
8. The polymer according to claim 1 , wherein the polymer is a polyalkylene dimethoxyterephthalate, having the structure:
9. The polymer according to claim 8 , wherein the polymer has a number average molecular weight in a range of from about 5,000 to about 500,000.
10. The polymer according to claim 8 , wherein the polymer has a weight average molecular weight in a range of from about 10,000 to about 1,000,000.
11. The polymer according to claim 8 , wherein the polymer has a dispersity in a range of from about 1.1 to about 10.
12. The polymer according to claim 8 , wherein the polymer has a glass transition temperature in a range of from about 5 to about 80° C.
13. A method for producing a polymer, comprising:
esterifying succinic acid to form dimethyl succinate;
dimerizing the dimethyl succinate to obtain dimethyl succinyl succinate;
aromatizing the dimethyl succinyl succinate via at least one selected from N-chlorosuccinimide oxidation, sulfuric acid oxidation, dimethylsulfoxide oxidation, hydrogen peroxide oxidation, and transfer dehydrogenation to produce dimethyl 2,5-dihydroxyterephthalate;
hydrolysing and optionally methylating the dimethyl 2,5-dihydroxyterephthalate to produce a monomer; and
polymerizing the monomer with a comonomer comprising at least 2 hydroxyl groups to produce the polymer.
14. The method according to claim 13 , wherein the comonomer is a linear diol having the structure:
HO(CH 2 ) n OH,
wherein n is from 1 to 20.