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 Laboratory (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1256045
Patent Number(s):
9359319
Application Number:
14/386,381
Assignee:
Los Alamos National Security, LLC (Los Alamos, NM)
Patent Classifications (CPCs):
B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
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 = {Tue Jun 07 00:00:00 EDT 2016},
month = {Tue Jun 07 00:00:00 EDT 2016}
}

Works referenced in this record:

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


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


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


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


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


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


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


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


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


Tweaking Copper Hydride (CuH) for Synthetic Gain. A Practical, One-Pot Conversion of Dialkyl Ketones to Reduced Trialkylsilyl Ether Derivatives
journal, August 2003


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


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


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


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


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


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


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
  • https://doi.org/10.1021/jo301595b

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


Nonhydride Mechanism of Metal-Catalyzed Hydrosilylation
journal, May 2011


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


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


Production Of Liquid Alkanes In The Jet Fuel Range (C8-C15) From Biomass-Derived Carbohydrates
patent-application, May 2009