Monomers from biomass

Patent metadata

Field	Value
Publication number	US-11220475-B2
Application number	US-201916722710-A
Country	US
Kind code	B2
Filing date	Dec 20, 2019
Priority date	Aug 8, 2014
Publication date	Jan 11, 2022
Grant date	Jan 11, 2022

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 II:

wherein both G′ and CT′ are independently

and where a is 1, 2 or 3; and b and c are independently 0, 1, 2, or 3.

2. The compound according to claim 1 , wherein at least one of b and c in both G 1 and G 2 are 0.

3. The compound according to claim 1 , wherein only one of b and c in both G 1 and G 2 are 0.

4. The compound according to claim 1 , wherein the structure of G 1 and G 2 are the same.

5. The compound according to claim 1 , wherein the compound of formula II is selected from:

6. A compound according to formula II:

wherein one of G 1 and G 2 is —(CH 2 ) d OH, wherein d is 1, 2, 3, 4 or 5, and the other of G 1 and G 2 is

where a is 1, 2 or 3; and b and c are independently 0, 1, 2, or 3,
—(CH 2 ) d OH where d is 1, 2, 3, 4 or 5, or
—(CH 2 ) e COOH where e is 0, 1, 2, 3, 4 or 5.

7. The compound according to claim 6 , wherein one of G 1 and G 2 is —(CH 2 ) d OH, wherein d is 1, 2, 3, 4 or 5, and the other of G 1 and G 2 is

8. The compound according to claim 6 , wherein the compound of formula II is:

9. A compound according to formula II:

wherein both G 1 and G 2 are independently —(CH 2 ) e COOH where e is 0, 1, 2, 3, 4 or 5,
with the caveat that if both G 1 and G 2 are —(CH 2 ) e COOH and one of e is 2 then the other e is not 0 or 2 and with the caveat that the compound according to formula II is asymmetric.

10. The compound according to claim 9 , wherein the compound of formula II is selected from:

11. The compound according to claim 1 derived from cellulose, hemicellulose or a combination thereof.

12. The compound according to claim 1 derived from fructose, cellulose, hemicellulose or a combination thereof.

13. The compound according to claim 12 , wherein the fructose is dehydrated to form 5-hydroxymethylfurfural (HMF).

14. The compound according to claim 1 , wherein the compound of formula II is polymerized.

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 a nylon, a polyester, a polyurethane, a polyamide, or a combination thereof.

17. The compound according to claim 14 , wherein the polymer can be used as an adhesive, a plastic, a thermoplastic, a gel, a coating, a film, or any combination thereof.

18. The compound according to claim 6 , derived from cellulose, hemicellulose or a combination thereof.

19. The compound according to claim 6 derived from fructose, cellulose, hemicellulose or a combination thereof.

20. The compound according to claim 19 , wherein the fructose is dehydrated to form 5-hydroxymethylfurfural (HMF).

21. The compound according to claim 6 , wherein the compound of formula II is polymerized.

22. The compound according to claim 21 , wherein the polymerization comprises free radical polymerization.

23. The compound according to claim 21 , wherein the polymer is a nylon, a polyester, a polyurethane, a polyamide, or a combination thereof.

24. The compound according to claim 21 , wherein the polymer can be used as an adhesive, a plastic, a thermoplastic, a gel, a coating, a film, or any combination thereof.

25. The compound according to claim 9 , derived from cellulose, hemicellulose or a combination thereof.

26. The compound according to claim 9 derived from fructose, cellulose, hemicellulose or a combination thereof.

27. The compound according to claim 26 , wherein the fructose is dehydrated to form 5-hydroxymethylfurfural (HMF).

28. The compound according to claim 9 , wherein the compound of formula II is polymerized.

29. The compound according to claim 28 , wherein the polymerization comprises free radical polymerization.

30. The compound according to claim 28 , wherein the polymer is a nylon, a polyester, a polyurethane, a polyamide, or a combination thereof.

31. The compound according to claim 28 , wherein the polymer can be 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

• C08G63/065

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

• C08G63/181

  Acids containing aromatic rings · CPC title

• C07C57/34 Primary

  containing more than one carboxyl group · CPC title

• C07D307/54

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07C57/40

  containing condensed ring systems · CPC title