Synthesis of R-glucosides, sugar alcohols, reduced sugar alcohols, and furan derivatives of reduced sugar alcohols
AssigneeArcher Daniels Midland Company
InventorsKenneth Stensrud, Chi-Cheng Ma, Kevin Martin
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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.
Claims7
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.
Dependencies are inferred from the claim text.