Reduction of HMF ethers with metal catalyst

Patent metadata

Field	Value
Publication number	US-9783516-B2
Application number	US-201615188075-A
Country	US
Kind code	B2
Filing date	Jun 21, 2016
Priority date	Oct 30, 2008
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

Methods of making reduced derivatives of hydroxymethyl furfural using metal catalysts are described. The derivatives may have tetrahydrofuran or furan nucleus with alkoxymethyl ether or ester moieties on the 5′ carbon and methanol on the 2′ carbon. Suitable metal catalyst include Raney nickel, a nickel catalyst with a zirconium promoter, a chromite catalyst with a barium, a palladium catalyst, such as palladium on carbon, or a ruthenium catalyst. Also provided are a new class of compounds, which are n-alkoxy hexane diols (i.e., 1,2 or 1,5 hexane diol ethers) and methods of making the same by reduction of furan or tetrahydrofuran derivatives.

First claim

What is claimed is:

1. A substitute solvent for a petroleum based glycol ether solvent comprising a bio-based solvent comprising a compound having at least one structure selected from the group consisting of:

wherein R is an alkyl group of 1 to 5 carbons;
wherein said substitute solvent has a bio-based content of at least 37.5% according to ASTM International Radioisotope Standard Method D 6866.

2. The substitute solvent of claim 1 , wherein the petroleum based glycol ether solvent is a carbitol.

3. The substitute solvent of claim 2 , wherein the carbitol is butyl carbitol.

Assignees

• Archer Daniels Midland Co
• Archer Daniels Midland Co

Inventors

• Bloom Paul
• Sanborn Alexandra

Classifications

• C07C41/26

  by introduction of hydroxy or O-metal groups · CPC title

• C07C43/13

  containing hydroxy or O-metal groups (C07C43/11 takes precedence) · CPC title

• C07D307/12

  Radicals substituted by oxygen atoms · CPC title

• C08K5/06

  Ethers; Acetals; Ketals; Ortho-esters · CPC title

• C07D307/44

  Furfuryl alcohol · CPC title