Monomers from biomass

Patent metadata

Field	Value
Publication number	US-10513482-B2
Application number	US-201515502653-A
Country	US
Kind code	B2
Filing date	Aug 7, 2015
Priority date	Aug 8, 2014
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

Abstract

Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.

First claim

What is claimed is:

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.

Assignees

• Sibi Mukund P
• Sermadurai Selvakumar
• Zimmermann Nicolas
• Serum Eric
• Ma Gaoyuan
• Moorthy Ramkumar
• Kalliokoski Krystal
• Ndsu Res Foundation

Inventors

• Sibi Mukund P
• Sermadurai Selvakumar
• Zimmermann Nicolas
• Serum Eric
• Ma Gaoyuan
• Moorthy Ramkumar
• Kalliokoski Krystal

Classifications

• C07C59/84

  containing six membered aromatic rings · CPC title

• C08G63/181

  Acids containing aromatic rings · CPC title

• C08G63/065

  the hydroxy and carboxylic ester groups being bound to aromatic rings · CPC title

• C07C57/34 Primary

  containing more than one carboxyl group · CPC title

• C07C57/40

  containing condensed ring systems · CPC title