Biorefining compounds and organocatalytic upgrading methods

Chen, Eugene Y.; Liu, Dajiang

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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:: Chen, Eugene Y.; Liu, Dajiang

Issue Date:: 2017-11-28

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

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C07D307/12 - Radicals substituted by oxygen atoms
C07D307/46 - Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
C07D407/06 - linked by a carbon chain containing only aliphatic carbon atoms

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10L - FUELS NOT OTHERWISE PROVIDED FOR
C10L1/026 - {for compression ignition}
C10L1/1855 - {Cyclic ethers, e.g. epoxides, lactides, lactones}

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02E - REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
Y02E50/10 - Biofuels

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02P - CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
Y02P30/20 - Bio-feedstock

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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.

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                    Chen, Eugene Y., & Liu, Dajiang. Biorefining compounds and organocatalytic upgrading methods.  United States.

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                    Chen, Eugene Y., and Liu, Dajiang. Tue .  
        "Biorefining compounds and organocatalytic upgrading methods".  United States.  https://www.osti.gov/servlets/purl/1410551.

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@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         = {2017},

  month        = {11}

}

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Works referenced in this record:

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

Dumesic, James A.; Rom{acute over (α)}n-Leshkov, Yuriy; Chheda, Juben Nemchand
US Patent Document 7,572,925
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7572925

2,2′-furoin derivatives and use thereof to light skin
patent, December 2014

Scheurich, Rene Peter
US Patent Document 8,906,351
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8906351