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Title: Decarbonylation and dehydrogenation of carbohydrates

Abstract

Carbohydrates, especially aldose or ketose sugars, including those whose carbonyl group is masked by hemi-acetal or hemi-ketal formation, are decarbonylated by heating the feed carbohydrate together with a transition metal complex in a suitable solvent. Also, primary alcohols, including sugar alditols are simultaneously dehydrogenated and decarbonylated by heating a mixture of rhodium and ruthenium complexes and the alcohol and optionally a hydrogen acceptor in an acceptable solvent. Such defarbonylation and/or dehydrogenation of sugars provides a convenient procedure for the synthesis of certain carbohydrates and may provide a means for the conversion of biomass into useful products.

Inventors:
;
Issue Date:
Research Org.:
Brookhaven National Laboratory (BNL), Upton, NY (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1176634
Patent Number(s):
H000918
Application Number:
07/253641
Assignee:
The United States of America as represented by the United States Department of Energy (Washington, DC)
DOE Contract Number:  
AC02-76CH00016
Resource Type:
Patent
Resource Relation:
Patent File Date: 1988 Oct 05
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS; statutory invention registration

Citation Formats

Andrews, Mark A., and Klaeren, Stephen A. Decarbonylation and dehydrogenation of carbohydrates. United States: N. p., 1991. Web.
Andrews, Mark A., & Klaeren, Stephen A. Decarbonylation and dehydrogenation of carbohydrates. United States.
Andrews, Mark A., and Klaeren, Stephen A. Tue . "Decarbonylation and dehydrogenation of carbohydrates". United States. https://www.osti.gov/servlets/purl/1176634.
@article{osti_1176634,
title = {Decarbonylation and dehydrogenation of carbohydrates},
author = {Andrews, Mark A. and Klaeren, Stephen A.},
abstractNote = {Carbohydrates, especially aldose or ketose sugars, including those whose carbonyl group is masked by hemi-acetal or hemi-ketal formation, are decarbonylated by heating the feed carbohydrate together with a transition metal complex in a suitable solvent. Also, primary alcohols, including sugar alditols are simultaneously dehydrogenated and decarbonylated by heating a mixture of rhodium and ruthenium complexes and the alcohol and optionally a hydrogen acceptor in an acceptable solvent. Such defarbonylation and/or dehydrogenation of sugars provides a convenient procedure for the synthesis of certain carbohydrates and may provide a means for the conversion of biomass into useful products.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1991},
month = {5}
}

Works referenced in this record:

The decarbonylation of aldehydes by tris(triphenylphosphine)chlororhodium(I)
journal, January 1968


Dichlorotris(triphenylphosphine)ruthenium(II) catalyzed dehydrogenation of some natural products using cyclohexanone as acceptor
journal, September 1982


Homogeneous catalytic hydrogenation of sugars
journal, July 1978


The Dehydration of D-Fructose to 5-Hydroxymethyl-2-furaldehyde
journal, December 1980


Deactivation of RuCl2(PPh3)3 during disproportionation of D-glucose in amide solvents
journal, December 1983


Catalytic decarbonylation of aldehydes
journal, October 1978


Photolysis of penta-O-acetyl-aldehydo-D-glucose
journal, August 1971


Catalytic decarbonylation of aldehydes using ruthenium(II) porphyrin systems
journal, January 1980


Decarbonylation of α-And β-Diketones Catalyzed by Rhodium Compounds
journal, March 1974


Photochemically induced ring contraction, a furanoid ring from a pyranosidulose
journal, January 1968


Detailed tautomeric equilibrium of aqueous D-glucose. Observation of six tautomers by ultrahigh resolution carbon-13 NMR
journal, May 1987