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Title: Biorefining compounds and organocatalytic upgrading methods

Abstract

The invention provides new methods for the direct umpolung self-condensation of 5-hydroxymethylfurfural (HMF) by organocatalysis, thereby upgrading the readily available substrate into 5,5'-di(hydroxymethyl) furoin (DHMF). While many efficient catalyst systems have been developed for conversion of plant biomass resources into HMF, the invention now provides methods to convert such nonfood biomass directly into DHMF by a simple process as described herein. The invention also provides highly effective new methods for upgrading other biomass furaldehydes and related compound to liquid fuels. The methods include the organocatalytic self-condensation (umpolung) of biomass furaldehydes into (C.sub.8-C.sub.12)furoin intermediates, followed by hydrogenation, etherification or esterification into oxygenated biodiesel, or hydrodeoxygenation by metal-acid tandem catalysis into premium hydrocarbon fuels.

Inventors:
;
Issue Date:
Research Org.:
Colorado State University Research Foundation, Fort Collins, CO (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1410551
Patent Number(s):
9828354
Application Number:
15/272,324
Assignee:
Colorado State University Research Foundation (Fort Collins, CO)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10L - FUELS NOT OTHERWISE PROVIDED FOR
DOE Contract Number:  
FG02-10ER16193
Resource Type:
Patent
Resource Relation:
Patent File Date: 2016 Sep 21
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Chen, Eugene Y., and Liu, Dajiang. Biorefining compounds and organocatalytic upgrading methods. United States: N. p., 2017. Web.
Chen, Eugene Y., & Liu, Dajiang. Biorefining compounds and organocatalytic upgrading methods. United States.
Chen, Eugene Y., and Liu, Dajiang. Tue . "Biorefining compounds and organocatalytic upgrading methods". United States. https://www.osti.gov/servlets/purl/1410551.
@article{osti_1410551,
title = {Biorefining compounds and organocatalytic upgrading methods},
author = {Chen, Eugene Y. and Liu, Dajiang},
abstractNote = {The invention provides new methods for the direct umpolung self-condensation of 5-hydroxymethylfurfural (HMF) by organocatalysis, thereby upgrading the readily available substrate into 5,5'-di(hydroxymethyl) furoin (DHMF). While many efficient catalyst systems have been developed for conversion of plant biomass resources into HMF, the invention now provides methods to convert such nonfood biomass directly into DHMF by a simple process as described herein. The invention also provides highly effective new methods for upgrading other biomass furaldehydes and related compound to liquid fuels. The methods include the organocatalytic self-condensation (umpolung) of biomass furaldehydes into (C.sub.8-C.sub.12)furoin intermediates, followed by hydrogenation, etherification or esterification into oxygenated biodiesel, or hydrodeoxygenation by metal-acid tandem catalysis into premium hydrocarbon fuels.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Nov 28 00:00:00 EST 2017},
month = {Tue Nov 28 00:00:00 EST 2017}
}

Works referenced in this record:

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Production Of Liquid Alkanes In The Jet Fuel Range (C8-C15) From Biomass-Derived Carbohydrates
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Method Of Pretreating Lignocellulose-Based Biomass
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Organocatalytic upgrading of the key biorefining building block by a catalytic ionic liquid and N-heterocyclic carbenes
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Polymeric ionic liquid (PIL)-supported recyclable catalysts for biomass conversion into HMF
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Thiazolium Salt Immobilized on Ionic Liquid: An Efficient Catalyst and Solvent for Preparation of α-Hydroxyketones
journal, August 2007


Efficient and mild benzoin condensation reaction catalyzed by simple 1-N-alkyl-3-methylimidazolium salts
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Ionic Liquid−Water Mixtures: Enhanced Kw for Efficient Cellulosic Biomass Conversion
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The hydrodeoxygenation of bioderived furans into alkanes
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