Biorefining compounds and organocatalytic upgrading methods

Chen, Eugene Y.; Liu, Dajiang

Biorefining compounds and organocatalytic upgrading methods

Patent · Tue Oct 18 04:00:00 EDT 2016

OSTI ID:1329321

Chen, Eugene Y.; Liu, Dajiang

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.

Research Organization:: Colorado State University Research Foundation, Fort Collins, CO (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: SC0005413

Assignee:: Colorado State University Research Foundation (Fort Collins, CO)

Patent Number(s):: 9,469,626

Application Number:: 13/934,074

OSTI ID:: 1329321

Country of Publication:: United States

Language:: English

References (6)

Polymeric ionic liquid (PIL)-supported recyclable catalysts for biomass conversion into HMF Liu, Dajiang (D. J.); Chen, Eugene Y.-X. Biomass and Bioenergy, Vol. 48, p. 181-190 https://doi.org/10.1016/j.biombioe.2012.11.020	journal	January 2013
Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates Huber, George W.; Chheda, Juben N.; Barrett, Christopher J. Science, Vol. 308, Issue 5727, p. 1446-1450 https://doi.org/10.1126/science.1111166	journal	June 2005
Production of high quality fuels from lignocellulose-derived chemicals: a convenient C–C bond formation of furfural, 5-methylfurfural and aromatic aldehyde Huang, Yao-Bing; Yang, Zhen; Dai, Jian-Jun RSC Advances, Vol. 2, Issue 30, p. 11211-11214 https://doi.org/10.1039/C2RA22008C	journal	January 2012
The hydrodeoxygenation of bioderived furans into alkanes Sutton, Andrew D.; Waldie, Fraser D.; Wu, Ruilian Nature Chemistry, Vol. 5, Issue 5, p. 428-432 https://doi.org/10.1038/nchem.1609	journal	April 2013
Ionic Liquid−Water Mixtures: Enhanced K_w for Efficient Cellulosic Biomass Conversion Zhang, Yuetao; Du, Hongbo; Qian, Xianghong Energy & Fuels, Vol. 24, Issue 4, p. 2410-2417 https://doi.org/10.1021/ef1000198	journal	April 2010
Organocatalytic upgrading of the key biorefining building block by a catalytic ionic liquid and N-heterocyclic carbenes Liu, Dajiang (D. J.); Zhang, Yuetao; Chen, Eugene Y.-X. Green Chemistry, Vol. 14, Issue 10, p. 2738-2746 https://doi.org/10.1039/C2GC36265A	journal	January 2012

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