skip to main content
DOE Patents title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Hydrogenation of biomass-derived substrates

Abstract

The .alpha.,.beta.-unsaturated ketone moiety of a substrate representative of non-food based biomass was hydrogenated to the corresponding saturated alcohol moiety using a composition including (1) a copper salt; (2) a phosphine; (3) a polar aprotic solvent such as acetonitrile, and (4) a compound suitable for providing hydrogen for the hydrogenation, such as a suitable silane material or a suitable siloxane material.

Inventors:
;
Issue Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1256045
Patent Number(s):
9,359,319
Application Number:
14/386,381
Assignee:
Los Alamos National Security, LLC (Los Alamos, NM)
DOE Contract Number:  
AC52-06NA25396
Resource Type:
Patent
Resource Relation:
Patent File Date: 2013 Mar 13
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Gordon, John C., and Waidmann, Christopher R. Hydrogenation of biomass-derived substrates. United States: N. p., 2016. Web.
Gordon, John C., & Waidmann, Christopher R. Hydrogenation of biomass-derived substrates. United States.
Gordon, John C., and Waidmann, Christopher R. Tue . "Hydrogenation of biomass-derived substrates". United States. https://www.osti.gov/servlets/purl/1256045.
@article{osti_1256045,
title = {Hydrogenation of biomass-derived substrates},
author = {Gordon, John C. and Waidmann, Christopher R.},
abstractNote = {The .alpha.,.beta.-unsaturated ketone moiety of a substrate representative of non-food based biomass was hydrogenated to the corresponding saturated alcohol moiety using a composition including (1) a copper salt; (2) a phosphine; (3) a polar aprotic solvent such as acetonitrile, and (4) a compound suitable for providing hydrogen for the hydrogenation, such as a suitable silane material or a suitable siloxane material.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2016},
month = {6}
}

Patent:

Save / Share:

Works referenced in this record:

Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation
journal, June 2011

  • Addis, Daniele; Das, Shoubhik; Junge, Kathrin
  • Angewandte Chemie International Edition, Vol. 50, Issue 27, p. 6004-6011
  • DOI: 10.1002/anie.201100145

(BDP)CuH:  A “Hot” Stryker's Reagent for Use in Achiral Conjugate Reductions
journal, January 2008

  • Baker, Benjamin A.; Bošković, Žarko V.; Lipshutz, Bruce H.
  • Organic Letters, Vol. 10, Issue 2
  • DOI: 10.1021/ol702689v

Highly Chemoselective Catalytic Hydrogenation of Unsaturated Ketones and Aldehydes to Unsaturated Alcohols Using Phosphine-Stabilized Copper(I) Hydride Complexes
journal, April 2000


Coordinating ability of anions and solvents towards transition metals and lanthanides
journal, January 2011

  • Díaz-Torres, Raúl; Alvarez, Santiago
  • Dalton Transactions, Vol. 40, Issue 40
  • DOI: 10.1039/C1DT11000D

The bite angle makes the difference: a practical ligand parameter for diphosphine ligands
journal, January 1999

  • Dierkes, Peter; van Leeuwen, Piet W. N. M.
  • Journal of the Chemical Society, Dalton Transactions, Issue 10
  • DOI: 10.1039/A807799A

Theoretical investigation on copper hydrides catalyzed hydrosilylation reaction of 3-methylcyclohex-2-enone: mechanism and ligands' effect
journal, January 2012

  • Dong, Liang; Qin, Song; Yang, Huaqing
  • Catal. Sci. Technol., Vol. 2, Issue 3
  • DOI: 10.1039/C1CY00320H

Catalytic Enantioselective Conjugate Reduction of Lactones and Lactams
journal, September 2003

  • Hughes, Gregory; Kimura, Masanari; Buchwald, Stephen L.
  • Journal of the American Chemical Society, Vol. 125, Issue 37
  • DOI: 10.1021/ja0351692

Mechanistic Studies on the Copper-Catalyzed Hydrosilylation of Ketones
journal, February 2010

  • Issenhuth, Jean-Thomas; Notter, François-Paul; Dagorne, Samuel
  • European Journal of Inorganic Chemistry, Vol. 2010, Issue 4
  • DOI: 10.1002/ejic.200900961

Mechanistic Aspects of Hydrosilylation Catalyzed by (ArN=)Mo(H)(Cl)(PMe 3 ) 3
journal, March 2012

  • Khalimon, Andrey Y.; Shirobokov, Oleg G.; Peterson, Erik
  • Inorganic Chemistry, Vol. 51, Issue 7
  • DOI: 10.1021/ic300010c

Asymmetric Hydrosilylation of Aryl Ketones Catalyzed by Copper Hydride Complexed by Nonracemic Biphenyl Bis - phosphine Ligands
journal, July 2003

  • Lipshutz, Bruce H.; Noson, Kevin; Chrisman, Will
  • Journal of the American Chemical Society, Vol. 125, Issue 29
  • DOI: 10.1021/ja021391f

Asymmetric 1,4-Reductions of Hindered β-Substituted Cycloalkenones Using Catalytic SEGPHOS−Ligated CuH
journal, April 2004

  • Lipshutz, Bruce H.; Servesko, Jeff M.; Petersen, Tue B.
  • Organic Letters, Vol. 6, Issue 8
  • DOI: 10.1021/ol0400185

Selective hydride-mediated conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds using [(Ph3P)CuH]6
journal, January 1988

  • Mahoney, Wayne S.; Brestensky, Donna M.; Stryker, Jeffrey M.
  • Journal of the American Chemical Society, Vol. 110, Issue 1
  • DOI: 10.1021/ja00209a048

Synthesis, Structure, and Alkyne Reactivity of a Dimeric (Carbene)copper(I) Hydride
journal, July 2004

  • Mankad, Neal P.; Laitar, David S.; Sadighi, Joseph P.
  • Organometallics, Vol. 23, Issue 14, p. 3369-3371
  • DOI: 10.1021/om0496380

A review of catalytic upgrading of bio-oil to engine fuels
journal, November 2011

  • Mortensen, P. M.; Grunwaldt, J.-D.; Jensen, P. A.
  • Applied Catalysis A: General, Vol. 407, Issue 1-2, p. 1-19
  • DOI: 10.1016/j.apcata.2011.08.046

A review of catalytic upgrading of bio-oil to engine fuels
journal, November 2011

  • Mortensen, P. M.; Grunwaldt, J.-D.; Jensen, P. A.
  • Applied Catalysis A: General, Vol. 407, Issue 1-2, p. 1-19
  • DOI: 10.1016/j.apcata.2011.08.046

CuH-Catalyzed Enantioselective 1,2-Reductions of α,β-Unsaturated Ketones
journal, June 2010

  • Moser, Ralph; Bošković, Žarko V.; Crowe, Christopher S.
  • Journal of the American Chemical Society, Vol. 132, Issue 23
  • DOI: 10.1021/ja102689e

Analysis of an Unprecedented Mechanism for the Catalytic Hydrosilylation of Carbonyl Compounds
journal, November 2007

  • Nolin, Kristine A.; Krumper, Jennifer R.; Pluth, Michael D.
  • Journal of the American Chemical Society, Vol. 129, Issue 47
  • DOI: 10.1021/ja074477n

Solvent Effect in Reactions Using Stryker’s Reagent
journal, September 2012

  • Sass, Daiane Cristina; Heleno, Vladimir Constantino Gomes; Cavalcante, Simone
  • The Journal of Organic Chemistry, Vol. 77, Issue 20
  • DOI: 10.1021/jo301595b

Catalytic routes for the conversion of biomass into liquid hydrocarbon transportation fuels
journal, January 2011

  • Serrano-Ruiz, Juan Carlos; Dumesic, James A.
  • Energy Environ. Sci., Vol. 4, Issue 1
  • DOI: 10.1039/C0EE00436G

Nonhydride Mechanism of Metal-Catalyzed Hydrosilylation
journal, May 2011

  • Shirobokov, Oleg G.; Kuzmina, Lyudmila G.; Nikonov, Georgii I.
  • Journal of the American Chemical Society, Vol. 133, Issue 17
  • DOI: 10.1021/ja111748u

Quantifying the Electronic Effect of Substituted Phosphine Ligands via Molecular Electrostatic Potential
journal, March 2002

  • Suresh, C. H.; Koga, Nobuaki
  • Inorganic Chemistry, Vol. 41, Issue 6
  • DOI: 10.1021/ic0109400

Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis
journal, June 1977


A remarkably effective copper(II)-dipyridylphosphine catalyst system for the asymmetric hydrosilylation of ketones in air
journal, February 2005

  • Wu, J.; Ji, J.-X.; Chan, A. S. C.
  • Proceedings of the National Academy of Sciences, Vol. 102, Issue 10, p. 3570-3575
  • DOI: 10.1073/pnas.0409043102

Application of Copper(II)-Dipyridylphosphine Catalyst in the Asymmetric Hydrosilylation of Simple Ketones in Air
journal, June 2009

  • Zhang, Xi-Chang; Wu, Yan; Yu, Feng
  • Chemistry - A European Journal, Vol. 15, Issue 24
  • DOI: 10.1002/chem.200900499