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PROCESSING LIGNIN DURING HYDROTHERMAL DIGESTION ( processing-lignin-during-hydrothermal-digestion )

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(12)United States Patent POWell et al. (54) METHODS AND SYSTEMS FOR PROCESSING LIGNIN DURING HYDROTHERMAL DIGESTION OF CELLULOSC BOMASS SOLIDS (71) Applicant: SHELLOIL COMPANY, Houston, TX (US) (72) Inventors:JosephBrounPowell,Houston,TX (US);KimberlyAnnJohnson, Richmond,TX (US);GlennCharles Komplin, Katy,TX (US); Edward James Denton, Richmond,TX (US) (73) Assignee: SHELLOILCOMPANY,Houston, TX (US) (*) Notice: Subjecttoanydisclaimer,thetermofthis patentisextendedoradjustedunder35 U.S.C.154(b)by0days. ThispatentisSubjecttoaterminaldis claimer. (21) Appl.No.:14/067,330 (22)Filed: Oct.30,2013 (10) Patent No.: US 9,562,160 B2 (45)DateofPatent: *Feb.7,2017 (65) (60) (51) (52) (58) (56) Prior Publication Data US2014/O117277A1 May1,2014 RelatedU.S.ApplicationData ProvisionalaplicationNo.61/720,747,filedonOct. 31,2012. CN EP (Continued) FOREIGN PATENT DOCUMENTS 102676198 3,2015 2182047 5,2010 (Continued) OTHER PUBLICATIONS Int.Cl. D2C3/00 D2C3/20 COSL 97/00 C8H 7/00 C8H8/00 CIOG I/06 CIOG 3/00 COSL 97/02 U.S.Cl. CPC.C08L97/005(2013.01);C08H6/00 (2013.01);C08H8/00(2013.01);C08L97/02 (2013.01):CI0G I/065(2013.01):CI0G3/42 (2013.01);C10G3/50(2013.01);D2IC3/20 (2013.01);C08L2203/40(2013.01);CIOG 2300/1014(2013.01);CI0G2400/02 (2013.01);C10G2400/04(2013.01);CIOG 2400/06(2013.01);C10G2400/20(2013.01); CI0G2400/22(2013.01);Y02P30/20 (2015.11) FieldofClasificationSearch CPC .C08G2300/1014:D21C3/20:D21C3/006 Seeaplicationfileforcompletesearchhistory. References Cited U.S. PATENT DOCUMENTS 3,882,015A* 5/1975Carson.208/169 4,017,642A * 4,1977 Orthetal. .426,69 Luo,Chenetal;"CelluloseConversionintoPolyolsCatalyzedby ReversiblyFormedAcidsandSupportedRutheniumClustersinHot Water”;Angew.Chem.Int.Ed.;vol.46;pp.7636-7639;2007. WrittenOpinionforPCT/US2013/066638datedDec.13,2013,4 pg.S. WrittenOpinionforPCT/US2013/066642datedDec.12,2013,5 pg.S. Luo,Chenetal.,Luo,Chenetal.,CelluloseConversionintoPolyols Catalyzed by Reversibly Formed Acids, Angew CHem. Int. Ed. 2007,46,7636-7639. InternationalSearchReportdatedOct.3,2014forApplicationNo. PCT/US2013,066660. InternationalSearchReportdatedOct.2,2014forApplicationNo. PCT/US2013,066666. (Continued) PrimaryExaminer—LiamJHeincer (57) ABSTRACT DigestionofcelulosicbiomassSolidsmaybecomplicated byreleaseoflignintherefrom.Methodsfordigestingcel lulosicbiomassSolidsmay comprise:providingcelulosic biomass solids in a digestion solvent; at least partialy convertingthecelulosicbiomassSolidsintoaphenolics liquidphasecomprisinglignin,anaqueousphasecompris ing an alcoholic component derived from the celulosic biomassSolids,andanoptionallightorganicsphase;and separating the phenolics liquid phase from the aqueous phase. 37Claims,1DrawingSheet (2006.01) (2006.01) (2006.01) (2011.01) (2010.01) (2006.01) (2006.01) (2006.01) 2011/0245444 A1* 10,2011 Milleretal..526,346 USOO95621.60B2 4,105,467 A * 4.259,294 A * 4,536,584.A * 4,968,409 A * 5,916,529A* 6,030,915 A 6,086,749 A * 6,127,229 A 8,262,905 B2 8,263,792B2* 9,222,028 B2 2008/0025903 A1* 2008/0058563 A1 2008/0216391A1 9/2008Cortrightetal. 2008/0312479A1* 12/2008 McCalletal..585,240 2009/0326286A1* 12/2009 Yieetal..585,240 2010.0137663A1* 6,2010Chen.C10G1,002 585,252 2010.0236988 A1 9/2010 Gabrielovetal. 2011/OO94149A1* 4/2011 Weissetal..44,308 2011/O154722A1* 6,2011Chhedaetal..44,307 2011/0167713A1* 7/2011Quignardetal..44,307 8/1978 Buckletal. .127/37 3/1981 VanZijlLanghout etal. .422,608 8/1985 Eskamanietal. .549,429 11/1990 Smith . .208/157 6/1999Scheuerman.422,141 2/2000 DeBoer 7/2000 Krameretal. .208,213 10/2000 Chu etal. 9/2012 Gabrielovetal. 9/2012 Robinson.549,483 12/2015 Powelletal. 1/2008 Cortright .423(437.1 3/2008 Dumesicetal..585,240 12/2011Zhangetal. 12/2011 Kalnesetal. .568,852 12/2011 Kalnesetal. . .568.913 2011/0312050Al 2011/0313208 A1* 2011/0313212 A1* 2012/0151827A1* 6,2012Powelletal..44,307 2012/015283.6A1* 6,2012Powelletal..210,620


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