US009988412B2 (12 ) United States Patent ( 10 ) Patent No .: U 8 , 412 B2 Jansen et al. ( 45 ) Date of Patent : Jun . 5 , 2018 (54 ) METHODS FOR PREPARING THERMALLY 58 ) Field of Classification Search STABLE LIGNIN FRACTIONS CPC combination set ( s ) only. See application file for complete search history . Applicant : Virdia , Inc ., Raceland , LA (US ) ( 71) ( 56 ) References Cited ( 72 ) Inventors : Robert Jansen , Collinsville , IL (US ) ; James Alan Lawson , Ellsworth , ME U . S . PATENT DOCUMENTS (US ) ; Noa Lapidot , Mevaseret Zion 2 , 380 , 448 A 7 / 1945 Katzen ( IL ) ; Bassem Hallac, Jerusalem ( IL ) ; 2 , 772 , 965 A 12 / 1956 Gray et al. Perry Rotem , Bazra ( IL ) 3 , 808 , 192 A 4 / 1974 Dimitri M 4 , 111 , 928 A 9 / 1978 Holsopple et al. 4 ,237 , 110 A 12 / 1980 Forster et al. ( 73 ) Assignee : VIRDIA , INC ., Raceland, LA (US ) 4 ,277 ,626 A 7 / 1981 Forss et al . 4 ,470 ,851 A 9 / 1984 Paszner et al. ( * ) Notice : Subject to any disclaimer , the term of this 4 ,520 , 105 A 5 / 1985 Sinner et al. patent is extended or adjusted under 35 4 ,740 , 591 A 4 / 1988 Dilling et al . U . S . C . 154 ( b ) by 0 days. days . 4 ,797 ,457 A 1 / 1989 Guiver et al . 4 , 946 , 946 A 8 / 1990 Fields et al . (21 ) Appl. No. : 15 /593 , 752 ( Continued ) ( 22 ) Filed : May 12 , 2017 FOREIGN PATENT DOCUMENTS 2812685 A1 3 /2012 (65 ) Prior Publication Data 101143881 A 3 / 2008 US 2018 /0079766 A1 Mar . 22 , 2018 ( Continued ) Related U . S . Application Data OTHER PUBLICATIONS (63 ) Continuation of application No . 14 /787 ,756 , filed as Abacherli, et al. Lignin Analytical Cluster , “ Towards Standardisa application No . PCT /US2014 / 036704 on May 2 , tion of Methods ” . Rome, Forum 8 , May 10 - 12 , 2007 . 2014 , now Pat . No . 9 ,683 , 005 . (Continued ) ( 60 ) Provisional application No . 61/ 819 , 485 , filed on May Primary Examiner — Ellen McAvoy 3 , 2013 , provisional application No . 61/ 953 , 572 , filed Assistant Examiner — Chantel Graham on Mar. 14 , 2014 . ( 74 ) Attorney, Agent, or Firm — Wilson Sonsini Goodrich ( 51 ) Int . Ci. & Rosati C07G 1 /00 ( 2011. 01 ) D21C 11 / 00 ( 2006 .01 ) ( 57 ) ABSTRACT D21C 3 / 20 ( 2006 .01 ) The present invention relates to fractions of high purity (52 ) U . S . CI. lignin which are thermally stable , and to methods of pro ??? . .. .. .. C07G 1 / 00 ( 2013 .01 ) ; D21C 3 /20 ducing said fractions from lignocellulosic material. (2013 . 01 ) ; D21C 11 /0007 ( 2013 .01 ) 20 Claims, 12 Drawing Sheets Hemicelulose sugar extraction Acidic hemicellulose sugar stream 1700 - A Lignocellulosic Bioenergy pellets Hemicellulose sugar 1700 -P2 purifications remainder -. - » Bioenero -Pellets 1740 1700 - P1 Acid Solvent lignin Hemicellulose extraction from Sugar mixture lignocellulosic 1710- P1 remainder 1760 -- Xylose removed Xylose Hemicellulose High purity Cellulose - 1710 - P2 sugar mixture Lignin 1760 -P2 1710 -P3 Bio - oil 1760 - P1 1780 -P1 US 9 ,988 ,412 B2 Page 2 (56 ) References Cited WO WO - 2009104995 A1 8 / 2009 WO WO - 2010043424 A1 4 / 2010 U . S . PATENT DOCUMENTS WO WO - 2010045576 A2 4 / 2010 wo WO - 2010060183 A1 6 / 2010 4 , 966 ,650 A 10 / 1990 Delong et al. WO WO - 2010045576 A3 7 / 2010 5 , 730 , 837 A 3 / 1998 Black et al . WO WO - 2010081231 A1 7 / 2010 5 , 865 , 948 A 2 / 1999 Lora et al. 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