Method to produce biomass-derived compounds using a co-solvent system containing gamma-valerolactone

Title: Method to produce biomass-derived compounds using a co-solvent system containing gamma-valerolactone

A method to produce an aqueous solution of carbohydrates containing C5- and/or C6-sugar-containing oligomers and/or C5- and/or C6-sugar monomers in which biomass or a biomass-derived reactant is reacted with a solvent system having an organic solvent, and organic co-solvent, and water, in the presence of an acid. The method produces the desired product, while a substantial portion of any lignin present in the reactant appears as a precipitate in the product mixture.

Inventors:: Dumesic, James A.; Motagamwala, Ali Hussain

Issue Date:: 2017-06-27

OSTI Identifier:: 1366756

Assignee:: Wisconsin Alumni Research Foundation CHO

Patent Number(s):: 9,688,845

Application Number:: 14/686,086

Contract Number:: FC02-07ER64494

Resource Relation:: Patent File Date: 2015 Apr 14

Research Org:: Wisconsin Alumni Research Foundation, Madison, WI (United States)

Sponsoring Org:: USDOE

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

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Other works cited in this record:

Method to produce water-soluble sugars from biomass using solvents containing lactones
patent, June 2015

Dumesic, James; Luterbacher, Jeremy
US Patent Document 9,045,804
URL: http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=%2Fnetahtml%2FPTO%2Fsearch-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN%2F9045804

Method For Producing Water-Insoluble Liquefied Fuel Oil From Biomass
patent-application, December 2010

Tsurutani, Kazushi; Sakai, Tsutomu; Kondo, Mitsuru
US Patent Application 12/794386; 20100312027
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220100312027%22.PGNR.&OS=DN/20100312027&RS=DN/20100312027

IONIC LIQUID SYSTEMS FOR THE PROCESSING OF BIOMASS, THEIR COMPONENTS AND/OR DERIVATIVES, AND MIXTURES THEREOF
patent-application, December 2010

RAHMAN, Mustafizur
US Patent Application 12/735827; 20100319862
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220100319862%22.PGNR.&OS=DN/20100319862&RS=DN/20100319862

Integrated Biorefineries For Production Of Sugars, Fermentation Products, And Coproducts
patent-application, December 2014

Retsina, Theodora; Pylkkanen, Vesa; O'Connor, Ryan
US Patent Application 14/286075; 20140356915
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220140356915%22.PGNR.&OS=DN/20140356915&RS=DN/20140356915

Acidity of Keggin-Type Heteropolycompounds Evaluated by Catalytic Probe Reactions, Sorption Microcalorimetry, and Density Functional Quantum Chemical Calculations
journal, December 1998

Bardin, Billy B.; Bordawekar, Shailendra V.; Neurock, Matthew
The Journal of Physical Chemistry B, Vol. 102, Issue 52, p. 10817-10825
DOI: 10.1021/jp982345y

Fermentable sugars by chemical hydrolysis of biomass
journal, March 2010

Binder, J. B.; Raines, R. T.
Proceedings of the National Academy of Sciences, Vol. 107, Issue 10, p. 4516-4521
DOI: 10.1073/pnas.0912073107

Conversion of Hemicellulose into Furfural Using Solid Acid Catalysts in γ-Valerolactone
journal, December 2012

Gürbüz, Elif I.; Gallo, Jean Marcel R.; Alonso, David Martin
Angewandte Chemie International Edition, Vol. 52, Issue 4, p. 1270-1274
DOI: 10.1002/anie.201207334

The Effect of Flow Rate of Very Dilute Sulfuric Acid on Xylan, Lignin, and Total Mass Removal from Corn Stover
journal, May 2004

Liu, Chaogang; Wyman, Charles E.
Industrial & Engineering Chemistry Research, Vol. 43, Issue 11, p. 2781-2788
DOI: 10.1021/ie030754x

Ionic liquid pretreatment of cellulosic biomass: Enzymatic hydrolysis and ionic liquid recycle
journal, December 2010

Shill, Kierston; Padmanabhan, Sasisanker; Xin, Qin
Biotechnology and Bioengineering, Vol. 108, Issue 3, p. 511-520
DOI: 10.1002/bit.23014

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