Method for preparing curable bicyclic compound derived from biomass

Patent metadata

Field	Value
Publication number	US-9994583-B2
Application number	US-201615221798-A
Country	US
Kind code	B2
Filing date	Jul 28, 2016
Priority date	Sep 8, 2009
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

The present invention relates to a method for preparing a curable bicyclic compound derived from biomass. The method includes preparing starting materials furan and methyl acrylate by preparing furan from hemicellulose extracted from biomass, and methyl acrylate from glycerol generated from biomass, preparing an intermediate compound comprising a bicycle and an alcohol functional group by reacting the furan and the methyl acrylate through a Diels-Alder reaction and consecutive reduction, and preparing a curable bicyclic compound that includes the bicycle and an epoxide functional group by reacting the intermediate compound and epichlorohydrin.

First claim

What is claimed is:

1. A method for preparing a curable bicyclic compound derived from biomass, the method comprising:
a step of preparing furan from hemicellulose extracted from biomass, and methyl acrylate from glycerol generated from biomass;
a step of preparing an intermediate compound comprising a bicycle and an alcohol functional group by reacting the furan and the methyl acrylate through a Diels-Alder reaction and consecutive reduction; and
a step of preparing a curable bicyclic compound comprising the bicycle and an epoxide functional group by reacting the intermediate compound and epichlorohydrin.

2. The method according to claim 1 , wherein the reduction at the step of preparing the intermediate compound involves hydrogenation.

3. The method according to claim 1 ,
wherein the step of preparing a curable bicyclic compound involves reacting a mixture comprising the intermediate compound and the epichlorohydrin using PTC (Phase Transfer Catalyst) as a catalyst in a bi-phasic solvent system where a sodium hydroxide aqueous solution is added.

4. The method according to claim 1 , wherein the step of preparing the intermediate compound involves separating the compound formed after the Diels-Alder reaction into endo type and exo type compounds respectively, and then conducting reducing the separated compounds respectively.

5. The method according to claim 1 , wherein the curable bicyclic compound comprising bicycle and one epoxide functional group is represented by any one of the following chemical structures III to V:

Assignees

• Korea Inst Ind Tech

Inventors

• Cho Jin-Ku
• Kim Sang-Yong
• Lee Do-Hoon
• Kim Bo-Ra
• Kim Baek-Jin
• Jung Jae-Won
• Lee Sang-Hyeup
• Lee Jae-Soung

Classifications

• A61K31/06

  the aromatic ring being substituted by nitro groups · CPC title

• C08G59/04

  of polyhydroxy compounds with epihalohydrins or precursors thereof · CPC title

• C07D493/08 Primary

  Bridged systems · CPC title

• C08F2/48

  by ultraviolet or visible light · CPC title

• C07D407/14 Primary

  containing three or more hetero rings · CPC title