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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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Dec . 2015 ; 8 ( 23 ) :3941 - 58 . doi : 10 . 1002 / cssc . 201500692 . Epub Nov. 16 , 2015 . FOREIGN PATENT DOCUMENTS Compere , et al. Evaluation of Lignin from Alkaline -Pulped Hard wood Black Liquor. Oak Ridge National Laboratory , US Depart CN 102027021 A 4 / 2011 CN 102361914 A 2 / 2012 ment of Energy, under contract DE - AC05 - 000822725, ORNLITM EP | 0224721 B1 6 / 1991 2005 /88 . May 2005 . EP 04465560 B1 8 / 1995 Compere , et al. Improving the fundamental properties of lignin EP 1272433 B1 1 / 2004 based carbon fiber for transportation application . Oak Ridge GB 1525508 A 9 / 1978 National Lab . 2009 . JP 2011256380 A 12 / 2011 Compere , et al . Low cost carbon fiber from renewable resources. WO WO - 9641052 A1 12 / 1996 Carbon . 1998 ; 36 ( 7 - 8 ): 1119 - 1124 . WO WO -0132715 A1 5 / 2001 Constantinescu , et al . Lignin hydrophobization by different WO WO -0202826 A1 1 / 2002 esterification reactions . ILI— Forum 8 , May 10 - 12 , 2007 . 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OTHER PUBLICATIONS International search report and written opinion dated Sep . 5 , 2014 for PCT/ US2014 /036704 . Finney, et al. Fuel Pelletization with a Binder : Part I — Identification Kadla , et al. Lignin - based carbon fibers for composite fiber appli of a Suitable Binder for Spent Mushroom Compost - Coal Tailing cations . Carbon . 2002 ; 40 :2913 - 2920 . Pellets . Energy & Fuels , 2009 , 23 ( 6 ) , pp . 3195 - 3202 . Khunsupat , et al . Molecular Weight Distribution of Lignin . Presen Gabilondo , et al. Lignin low molar mass fractions involvement in tation ; Georgia Institute of Technology .
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    Extraction, Modification and Characterization of Lignin from Oil Palm Fronds As Corrosion Inhibitors for Mild Steel in Acidic Solution Mohd Hazwan Bin Hussin

    Extraction, modification and characterization of lignin from oil palm fronds as corrosion inhibitors for mild steel in acidic solution Mohd Hazwan Bin Hussin To cite this version: Mohd Hazwan Bin Hussin. Extraction, modification and characterization of lignin from oil palm fronds as corrosion inhibitors for mild steel in acidic solution. Food and Nutrition. Université de Lorraine, 2014. English. NNT : 2014LORR0135. tel-01750984 HAL Id: tel-01750984 https://hal.univ-lorraine.fr/tel-01750984 Submitted on 29 Mar 2018 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. AVERTISSEMENT Ce document est le fruit d'un long travail approuvé par le jury de soutenance et mis à disposition de l'ensemble de la communauté universitaire élargie. Il est soumis à la propriété intellectuelle de l'auteur. Ceci implique une obligation de citation et de référencement lors de l’utilisation de ce document. D'autre part, toute contrefaçon, plagiat, reproduction illicite encourt une poursuite pénale. Contact : [email protected] LIENS Code de la Propriété Intellectuelle. articles L 122. 4 Code de la Propriété Intellectuelle. articles L 335.2- L 335.10 http://www.cfcopies.com/V2/leg/leg_droi.php http://www.culture.gouv.fr/culture/infos-pratiques/droits/protection.htm Faculté des Sciences et Technique U.F.R.
  • Plant Genetic Engineering for Biofuel Production: Towards Affordable Cellulosic Ethanol

    Plant Genetic Engineering for Biofuel Production: Towards Affordable Cellulosic Ethanol

    FOCUS ON GLOBAL CHALLREVIEWSENGes RETRACTED Plant genetic engineering for biofuel production: towards affordable cellulosic ethanol Mariam B. Sticklen Abstract | Biofuels provide a potential route to avoiding the global political instability and environmental issues that arise from reliance on petroleum. Currently, most biofuel is in the form of ethanol generated from starch or sugar, but this can meet only a limited fraction of global fuel requirements. Conversion of cellulosic biomass, which is both abundant and renewable, is a promising alternative. However, the cellulases and pretreatment processes involved are very expensive. Genetically engineering plants to produce cellulases and hemicellulases, and to reduce the need for pretreatment processes through lignin modification, are promising paths to solving this problem, together with other strategies, such as increasing plant polysaccharide content and overall biomass. Finite petroleum reserves and the increasing demands Starch- and sugar-derived ethanol already make a for energy in industrial countries have created inter- relatively small but significant contribution to global national unease. For example, the dependence of the energy supplies. In particular, Brazil produces relatively United States on foreign petroleum both undermines its cheap ethanol from the fermentation of sugarcane sugar economic strength and threatens its national security1. to supply one quarter of its ground transportation fuel. In As highly populated countries such as China and India addition, the United States produces ethanol from corn become more industrialized, they too might face similar grain. However, even if all the corn grain produced in problems. It is also clear that no country in the world the United States were converted into ethanol, this could is untouched by the negative environmental effects of only supply about 15% of that country’s transportation petroleum extraction, refining, transportation and use.