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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:
1329321
Patent Number(s):
9469626
Application Number:
13/934,074
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: 2013 Jul 02
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS

Citation Formats

Chen, Eugene Y., and Liu, Dajiang. Biorefining compounds and organocatalytic upgrading methods. United States: N. p., 2016. 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/1329321.
@article{osti_1329321,
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 Oct 18 00:00:00 EDT 2016},
month = {Tue Oct 18 00:00:00 EDT 2016}
}

Works referenced in this record:

Catalytic process for producing furan derivatives in a biphasic reactor
patent, August 2009


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


Method Of Pretreating Lignocellulose-Based Biomass
patent-application, November 2010


Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates
journal, June 2005


Polymeric ionic liquid (PIL)-supported recyclable catalysts for biomass conversion into HMF
journal, January 2013


The hydrodeoxygenation of bioderived furans into alkanes
journal, April 2013


Ionic Liquid−Water Mixtures: Enhanced Kw for Efficient Cellulosic Biomass Conversion
journal, April 2010