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Title: Method of carbon chain extension using novel aldol reaction

Abstract

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.

Inventors:
; ; ;
Publication Date:
Research Org.:
Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1092974
Patent Number(s):
8,507,700
Application Number:
13/556,484
Assignee:
Los Alamos National Security, LLC (Los Alamos, NM)
DOE Contract Number:  
AC52-06NA25396
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Silks, Louis A, Gordon, John C, Wu, Ruilan, and Hangson, Susan Kloek. Method of carbon chain extension using novel aldol reaction. United States: N. p., 2013. Web.
Silks, Louis A, Gordon, John C, Wu, Ruilan, & Hangson, Susan Kloek. Method of carbon chain extension using novel aldol reaction. United States.
Silks, Louis A, Gordon, John C, Wu, Ruilan, and Hangson, Susan Kloek. 2013. "Method of carbon chain extension using novel aldol reaction". United States. https://www.osti.gov/servlets/purl/1092974.
@article{osti_1092974,
title = {Method of carbon chain extension using novel aldol reaction},
author = {Silks, Louis A and Gordon, John C and Wu, Ruilan and Hangson, Susan Kloek},
abstractNote = {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.},
doi = {},
url = {https://www.osti.gov/biblio/1092974}, journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Aug 13 00:00:00 EDT 2013},
month = {Tue Aug 13 00:00:00 EDT 2013}
}

Works referenced in this record:

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