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
- Baird, M. C.; Nyman, C. J.; Wilkinson, G.
- Journal of the Chemical Society A: Inorganic, Physical, Theoretical
Dichlorotris(triphenylphosphine)ruthenium(II) catalyzed dehydrogenation of some natural products using cyclohexanone as acceptor
journal, September 1982
- Muthukumaru Pillai, S.; Vancheesan, S.; Rajaram, J.
- Journal of Molecular Catalysis, Vol. 16, Issue 3
Homogeneous catalytic hydrogenation of sugars
journal, July 1978
- Kruse, Walter M.; Wright, Leon W.
- Carbohydrate Research, Vol. 64
The Dehydration of D-Fructose to 5-Hydroxymethyl-2-furaldehyde
journal, December 1980
- Nakamura, Yoshio; Morikawa, Shunichi
- Bulletin of the Chemical Society of Japan, Vol. 53, Issue 12
Deactivation of RuCl2(PPh3)3 during disproportionation of D-glucose in amide solvents
journal, December 1983
- Rajagopal, S.; Vancheesan, S.; Rajaram, J.
- Journal of Molecular Catalysis, Vol. 22, Issue 2
Catalytic decarbonylation of aldehydes
journal, October 1978
- Doughty, D. H.; Pignolet, L. H.
- Journal of the American Chemical Society, Vol. 100, Issue 22
Syntheses of all four possible diastereomers of the acyclonucleoside 9-(1,3,4-trihydroxy-2-butoxymethyl)guanine from carbohydrate precursors
journal, January 1985
- MacCoss, Malcolm; Chen, Anna; Tolman, Richard L.
- Tetrahedron Letters, Vol. 26, Issue 36
Photolysis of penta-O-acetyl-aldehydo-D-glucose
journal, August 1971
- Whistler, Roy L.; Ong, Khong-Seng
- The Journal of Organic Chemistry, Vol. 36, Issue 17
Organic synthesis by means of noble metal compounds. XXXV. Novel decarbonylation reactions of aldehydes and acyl halides using rhodium complexes
journal, January 1968
- Ohno, Kiyotaka; Tsuji, Jiro
- Journal of the American Chemical Society, Vol. 90, Issue 1
Catalytic decarbonylation of aldehydes using ruthenium(II) porphyrin systems
journal, January 1980
- Domazetis, George; Tarpey, Blaithin; Dolphin, David
- Journal of the Chemical Society, Chemical Communications, Issue 20
Decarbonylation of α-And β-Diketones Catalyzed by Rhodium Compounds
journal, March 1974
- Kaneda, Kiyotomi; Azuma, Hiromichi; Wayaku, Masami
- Chemistry Letters, Vol. 3, Issue 3
Photochemically induced ring contraction, a furanoid ring from a pyranosidulose
journal, January 1968
- Collins, Peter M.
- Chemical Communications (London), Issue 7
Detailed tautomeric equilibrium of aqueous D-glucose. Observation of six tautomers by ultrahigh resolution carbon-13 NMR
journal, May 1987
- Maple, Steven R.; Allerhand, Adam
- Journal of the American Chemical Society, Vol. 109, Issue 10