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Title: Method of carbon chain extension using novel aldol reaction

Patent ·
OSTI ID:1092974

Method of producing C.sub.8-C.sub.15 hydrocarbons comprising providing a ketone starting material; providing an aldol starting material comprising hydroxymethylfurfural; mixing the ketone starting material and the aldol starting material in a reaction in the presence of a proline-containing catalyst selected from the group consisting of Zn(Pro).sub.2, Yb(Pro).sub.2, and combinations thereof, or a catalyst having one of the structures (I), (II) or (III), and in the presence of a solvent, wherein the solvent comprises water and is substantially free of organic solvents, where (I), (II) and (III) respectively are: ##STR00001## where R.sub.1 is a C.sub.1-C.sub.6 alkyl moiety, X=(OH) and n=2. ##STR00002## In (III), X may be CH.sub.2, sulfur or selenium, M may be Zn, Mg, or a lanthanide, and R.sub.1 and R.sub.2 each independently may be a methyl, ethyl, phenyl moiety.

Research Organization:
Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
AC52-06NA25396
Assignee:
Los Alamos National Security, LLC (Los Alamos, NM)
Patent Number(s):
8,507,700
Application Number:
13/556,484
OSTI ID:
1092974
Country of Publication:
United States
Language:
English

References (10)

Production Of Liquid Alkanes In The Jet Fuel Range (C8-C15) From Biomass-Derived Carbohydrates patent-application May 2009
A Selective Direct Aldol Reaction in Aqueous Media Catalyzed byZinc-Proline journal December 2005
Direct, High-Yield Conversion of Cellulose into Biofuel journal September 2008
Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates journal June 2005
Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals journal February 2009
Aqueous Aldol Catalysis by a Nicotine Metabolite journal March 2002
Highly Efficient Small Organic Molecules for Enantioselective Direct Aldol Reaction in Organic and Aqueous Media journal May 2009
Carbon–carbon bond formation for biomass-derived furfurals and ketones by aldol condensation in a biphasic system journal December 2008
Zn-Proline catalyzed direct aldol reaction in aqueous mediaElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b301117h/ journal March 2003
Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water journal May 2005