Synthesis of R-glucosides, sugar alcohols, reduced sugar alcohols, and furan derivatives of reduced sugar alcohols

Patent metadata

Field	Value
Publication number	US-10519124-B2
Application number	US-201815962044-A
Country	US
Kind code	B2
Filing date	Apr 25, 2018
Priority date	Apr 10, 2014
Publication date	Dec 31, 2019
Grant date	Dec 31, 2019

Abstract

Disclosed herein are methods for synthesizing 1,2,5,6-hexanetetrol (HTO), 1,6 hexanediol (HDO) and other reduced polyols from C5 and C6 sugar alcohols or R glycosides. The methods include contacting the sugar alcohol or R-glycoside with a copper catalyst, most desirably a Raney copper catalyst with hydrogen for a time, temperature and pressure sufficient to form reduced polyols having 2 to 3 fewer hydoxy groups than the starting material. When the starting compound is a C6 sugar alcohol such as sorbitol or R-glycoside of a C6 sugar such as methyl glucoside, the predominant product is HTO. The same catalyst can be used to further reduce the HTO to HDO.

First claim

What is claimed is:

1. A method of making 2,5-bis(hydroxymethyl)tetrahydrofuran, comprising: contacting a mixture comprising 1,2,5,6-hexanetetrol with an acid catalyst selected from the group consisting of carbonic acid and a water tolerant non-Bronsted Lewis acid in the form of a triflate compound for a time and at a temperature and a pressure sufficient to convert the 1,2,5,6-hexanetetrol to 2,5 bis(hydroxymethyl)tetrahydrofuran.

2. The method of claim 1 , wherein the non-Bronsted Lewis acid is selected from the group consisting of bismuth triflate and scandium triflate.

3. The method of claim 1 , wherein the reaction mixture is heated to a temperature between 110° C. and 150° C.

4. The method of claim 1 , wherein the mixture is contacted with the catalyst under vacuum pressure of between 0.021 MPa and 0.041 MPa (3 and 6 psi).

5. The method of claim 1 , wherein the mixture is contacted with the catalyst under vacuum pressure of less than 0.0023 MPa (0.4 psi).

6. The method of claim 1 , wherein the acid catalyst is present in an amount between 0.5 mol % and 5 mol % based on the amount of the 1,2,5,6-hexanetetrol.

7. The method of claim 1 , further comprising separating the 2,5-bis(hydroxymethyl) tetrahydrofuran from the mixture and contacting the separated 2,5-bis(hydroxymethyl)tetrahydrofuran with a rhenium oxide catalyst further comprising silicon oxide for a time and a temperature sufficient to convert the 2,5-bis(hydroxymethyl)tetrahydrofuran to 1,6 hexanediol.

Assignees

• Archer Daniels Midland Co

Inventors

• Stensrud Kenneth
• Ma chi-cheng
• Martin Kevin

Classifications

• B01J27/20

  Carbon compounds · CPC title

• B01J23/462

  Ruthenium · CPC title

• C07C31/22

  Trihydroxylic alcohols, e.g. glycerol · CPC title

• B01J23/72

  Copper · CPC title

• C07C29/132

  by reduction of an oxygen containing functional group · CPC title