Monomers from biomass
Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.
1. A compound according to formula I:
where a is 1, 2 or 3; and b and c are independently 0, 1, 2, or 3;
B is A, —OH, or —OR where R is —CH 3 , —CH 2 CH 3 , CH 2 CH 2 CH 3 , CHCH 2 , CHCHCH 3 , or CH 2 CHCH 2 ;
D 1 and D 2 are independently H, —OH, or —OR where R is —CH 3 , —CH 2 CH 3 , CH 2 CH 2 CH 3 , CHCH 2 , CHCHCH 3 , or CH 2 CHCH 2 ; and
E is H or together with D 1 and the phenyl ring attached thereto forms a naphthalene ring,
with the provisos that if a is 1, b is 1, c is 0, D 2 is —OCH 3 , B is —OH, then D 1 is not H; and if a is 1, b is 1, c is 0, D 2 is —OCH 3 , B is —OCH 3 E is H, then D 1 is not H.
2. The compound according to claim 1 , wherein both A and B are
3. The compound according to claim 2 , wherein both A and B have the same structure.
4. The compound according to claim 1 , wherein D 1 is H.
5. The compound according to claim 1 , wherein D 1 together with E and the phenyl ring attached thereto forms a naphthalene ring.
6. The compound according to claim 5 , wherein both A and B are
7. The compound according to claim 1 , wherein the compound of formula I is selected from the group consisting of:
where R is as defined above and R 1 is —CH 3 , —CH 2 CH 3 CH 2 CH 2 CH 3 , CHCH 2 , CHCHCH 3 , or CH 2 CHCH 2 .
8. The compound according to claim 1 derived from lignins.
9. The compound according to claim 8 , wherein the lignins are depolymerized.
10. The compound according to claim 9 , wherein the depolymerized lignins include a phenolic hydroxyl group.
11. The compound according to claim 10 , wherein the phenolic hydroxyl group is converted to a leaving group.
12. The compound according to claim 9 , wherein at least one carbon chain in the depolymerized lignin is extended via a Kumada coupling.
13. The compound according to claim 1 , wherein the compound of formula I is derived from the group consisting of: eugenol, isoeugenol, guiacol, vanillin, isovanillin, chavicol, chavibetol, and combinations thereof.
14. The compound according to claim 1 , wherein the compound of formula I is polymerized to form a polymer.
15. The compound according to claim 14 , wherein the polymerization comprises free radical polymerization.
16. The compound according to claim 14 , wherein the polymer is selected from the group consisting of: a nylon, a polyester, a polyurethane, a polyamide, or a combination thereof.
17. The compound according to claim 14 , wherein the polymer is used as an adhesive, a plastic, a thermoplastic, a gel, a coating, a film, or any combination thereof.