WO2009021733A3 - One-step conversion of solid lignin to liquid products - Google Patents

One-step conversion of solid lignin to liquid products Download PDF

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Publication number
WO2009021733A3
WO2009021733A3 PCT/EP2008/006672 EP2008006672W WO2009021733A3 WO 2009021733 A3 WO2009021733 A3 WO 2009021733A3 EP 2008006672 W EP2008006672 W EP 2008006672W WO 2009021733 A3 WO2009021733 A3 WO 2009021733A3
Authority
WO
WIPO (PCT)
Prior art keywords
liquid products
step conversion
solid lignin
liquid product
lignin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2008/006672
Other languages
French (fr)
Other versions
WO2009021733A2 (en
Inventor
Mike Kleinert
Tatjana Tanja Barth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Vestlandets Innovasjonsselskap AS
Original Assignee
Bergen Teknologioverforing AS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38969398&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2009021733(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to RU2010109383/04A priority Critical patent/RU2476581C2/en
Priority to DK08801573.0T priority patent/DK2190949T3/en
Priority to CA2696268A priority patent/CA2696268C/en
Priority to EP08801573A priority patent/EP2190949B1/en
Priority to AT08801573T priority patent/ATE554153T1/en
Application filed by Bergen Teknologioverforing AS filed Critical Bergen Teknologioverforing AS
Priority to BRPI0815466-0A priority patent/BRPI0815466A2/en
Priority to PL08801573T priority patent/PL2190949T3/en
Priority to CN200880106910.0A priority patent/CN101932670B/en
Priority to US12/673,242 priority patent/US8673027B2/en
Publication of WO2009021733A2 publication Critical patent/WO2009021733A2/en
Publication of WO2009021733A3 publication Critical patent/WO2009021733A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C07C37/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes
    • C07C37/54—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes by hydrolysis of lignin or sulfite waste liquor
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/06—Alkylated phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1011—Biomass
    • C10G2300/1014—Biomass of vegetal origin
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4006—Temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4012—Pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4025—Yield
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Botany (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Catalysts (AREA)

Abstract

The present invention refers to a method of converting a lignin material into a liquid product by treatment in a reaction medium comprising at least one C1-C2 carboxylic acid under devated temperature and pressure and the liquid product obtainable by the method.
PCT/EP2008/006672 2007-08-14 2008-08-13 One-step conversion of solid lignin to liquid products Ceased WO2009021733A2 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US12/673,242 US8673027B2 (en) 2007-08-14 2008-08-13 One-step conversion of solid lignin to liquid products
PL08801573T PL2190949T3 (en) 2007-08-14 2008-08-13 One-step conversion of solid lignin to liquid products
CA2696268A CA2696268C (en) 2007-08-14 2008-08-13 One-step conversion of solid lignin to liquid products
EP08801573A EP2190949B1 (en) 2007-08-14 2008-08-13 One-step conversion of solid lignin to liquid products
AT08801573T ATE554153T1 (en) 2007-08-14 2008-08-13 ONE-STEP CONVERSION OF SOLID LIGNIN INTO LIQUID PRODUCTS
RU2010109383/04A RU2476581C2 (en) 2007-08-14 2008-08-13 Single-step conversion of solid lignin to liquid products
BRPI0815466-0A BRPI0815466A2 (en) 2007-08-14 2008-08-13 Converting a solid lignin step to liquid products
DK08801573.0T DK2190949T3 (en) 2007-08-14 2008-08-13 One-step conversion of solid lignin to liquid products
CN200880106910.0A CN101932670B (en) 2007-08-14 2008-08-13 One-step conversion of solid lignin to liquid products

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07015978A EP2025735A1 (en) 2007-08-14 2007-08-14 One-step conversion of solid lignin to liquid products
EP07015978.5 2007-08-14

Publications (2)

Publication Number Publication Date
WO2009021733A2 WO2009021733A2 (en) 2009-02-19
WO2009021733A3 true WO2009021733A3 (en) 2009-06-25

Family

ID=38969398

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/006672 Ceased WO2009021733A2 (en) 2007-08-14 2008-08-13 One-step conversion of solid lignin to liquid products

Country Status (10)

Country Link
US (1) US8673027B2 (en)
EP (2) EP2025735A1 (en)
CN (1) CN101932670B (en)
AT (1) ATE554153T1 (en)
BR (1) BRPI0815466A2 (en)
CA (1) CA2696268C (en)
DK (1) DK2190949T3 (en)
PL (1) PL2190949T3 (en)
RU (1) RU2476581C2 (en)
WO (1) WO2009021733A2 (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9410216B2 (en) 2010-06-26 2016-08-09 Virdia, Inc. Sugar mixtures and methods for production and use thereof
US9512495B2 (en) 2011-04-07 2016-12-06 Virdia, Inc. Lignocellulose conversion processes and products
US9657146B2 (en) 2013-03-14 2017-05-23 Virdia, Inc. Methods for treating lignocellulosic materials
US9683005B2 (en) 2013-05-03 2017-06-20 Virdia, Inc. Methods for preparing thermally stable lignin fractions
US9783861B2 (en) 2012-05-03 2017-10-10 Virdia, Inc. Methods for treating lignocellulosic materials
US10138332B2 (en) 2013-05-03 2018-11-27 Virdia, Inc. Methods for treating lignocellulosic materials
US10767308B2 (en) 2014-07-09 2020-09-08 Virdia, Inc. Methods for separating and refining lignin from black liquor and compositions thereof
US11242650B2 (en) 2010-08-01 2022-02-08 Virdia, Llc Methods and systems for solvent purification

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MY159547A (en) * 2008-10-01 2017-01-13 Licella Pty Ltd Bio-oil production method
CN102459426B (en) 2009-05-28 2016-10-05 丽格诺创新有限公司 Derivatives of native lignin
US9051244B2 (en) 2010-01-27 2015-06-09 Council Of Scientific And Industrial Research Depolymerization of lignin using solid acid catalysts
WO2011097719A1 (en) 2010-02-15 2011-08-18 Lignol Innovations Ltd. Binder compositions comprising lignin derivatives
CA2798268C (en) 2010-02-15 2019-02-12 Suzano Canada Inc. Carbon fibre compositions comprising lignin derivatives
IL206678A0 (en) 2010-06-28 2010-12-30 Hcl Cleantech Ltd A method for the production of fermentable sugars
ES2738905T5 (en) 2011-01-05 2022-11-22 Licella Pty Ltd Organic matter processing
ES2795047T3 (en) 2011-02-01 2020-11-20 Univ Maine System Procedure to improve the energy density of raw materials using formate salts
WO2012126099A1 (en) 2011-03-24 2012-09-27 Lignol Innovations Ltd. Compositions comprising lignocellulosic biomass and organic solvent
EP3848437A1 (en) * 2011-06-10 2021-07-14 Steeper Energy ApS Process and apparatus for producing liquid hydrocarbons
US9080109B2 (en) * 2011-12-14 2015-07-14 Uop Llc Methods for deoxygenating biomass-derived pyrolysis oil
IN2014MN01731A (en) * 2012-02-24 2015-07-03 Biochemtex Spa
CN103304821B (en) * 2012-03-09 2016-01-20 东北林业大学 A kind of process for purification of xylogen
UA116535C2 (en) * 2012-03-30 2018-04-10 Рдінновейшн Апс Benzene polycarboxylic acid compounds and their use as drug
RU2488445C1 (en) * 2012-04-26 2013-07-27 Общество с ограниченной ответственностью "Целлокорм" Synthesis of multifunctional catalyst for oxidative cracking of organic material and method for liquid-phase low-temperature oxidative cracking of organic material (versions)
CN103073395B (en) * 2012-12-11 2015-04-08 浙江大学 Technology for preparing micro-molecular phenolic compound through microwave reinforced continuous degradation of lignin in hydrogen donor
US9920201B2 (en) 2013-01-25 2018-03-20 Ren Fuel K2B Ab Compositions of biomass materials for refining
CN103274904B (en) * 2013-06-08 2015-11-18 中国科学院过程工程研究所 A kind of microwave-assisted xylogen orientation transforms the method for phenol
CN103508871B (en) * 2013-10-25 2015-06-17 东南大学 Method for preparing 4-hydroxy-3-methoxy acetophenone through liquid phase degradation of black liquor lignin
PT3083652T (en) * 2013-12-16 2021-10-13 Ren Fuel K2B Ab Composition comprising esters of lignin and oil or fatty acids
WO2015168571A1 (en) 2014-05-01 2015-11-05 Renmatix, Inc. Upgrading lignin from lignin-containing residues through reactive extraction
EP2982733A1 (en) * 2014-08-05 2016-02-10 Linde Aktiengesellschaft Method of recovering oleagineous compounds from hydrothermally biomass
WO2016114668A1 (en) 2015-01-16 2016-07-21 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Method to prepare phenolics from biomass
FI127675B (en) 2015-02-06 2018-11-30 Upm Kymmene Corp A method and an apparatus for increasing concentration of soluble carbohyrate containing fraction, a soluble carbohyrate containing fraction, a solid fraction and their use
CN106350090B (en) * 2015-07-21 2019-03-08 中国石油化工股份有限公司 A kind of processing method of biomass co-refining product
CN106367095B (en) * 2015-07-21 2019-03-08 中国石油化工股份有限公司 A kind of processing method of biomass co-refining product
SE543595C2 (en) * 2015-12-01 2021-04-06 Ren Fuel K2B Ab Depolymerized lignin in hydrocarbon oil
FR3061492B1 (en) * 2017-01-03 2019-05-24 D.M.S PROCESS FOR PRODUCTION OF FUEL BY CATALYTIC CRACKING OF A SOLID HYDROCARBON MATERIAL AND DEVICE FOR IMPLEMENTING SAID METHOD
DK201870095A1 (en) * 2018-02-16 2019-09-24 Københavns Universitet A biofuel composition comprising lignin
FI130333B (en) 2021-12-23 2023-06-26 Upm Kymmene Corp Solvolysis method for combined feed
KR20260006557A (en) * 2023-04-18 2026-01-13 디아이씨 가부시끼가이샤 Kraft lignin and its production method

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US3186923A (en) * 1961-06-12 1965-06-01 Buckeye Cellulose Corp Process for improving the low molecular weight yield in bark pyrolysis
AU518450B2 (en) * 1979-08-10 1981-10-01 Robert Jeno Hamor Improvements in or relating to the hydrolysis of cellulose
FR2770543A1 (en) * 1997-10-30 1999-05-07 Michel Delmas Preparation of paper pulp from lignocellulose material
WO2000044699A1 (en) * 1999-01-29 2000-08-03 Ecovac Pyrocycling Technologies Inc. Process for the production of phenolic-rich pyrolysis oils for use in making phenol-formaldehyde resol resins

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US3976437A (en) * 1972-06-23 1976-08-24 Sun Ventures, Inc. Composition comprising a methyl phenol and an ether for gasoline fuels
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SI2007945T1 (en) * 2006-03-29 2011-05-31 Virginia Tech Intell Prop Cellulose-solvent-based lignocellulose fractionation with modest reaction conditions and reagent cycling

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US3186923A (en) * 1961-06-12 1965-06-01 Buckeye Cellulose Corp Process for improving the low molecular weight yield in bark pyrolysis
AU518450B2 (en) * 1979-08-10 1981-10-01 Robert Jeno Hamor Improvements in or relating to the hydrolysis of cellulose
FR2770543A1 (en) * 1997-10-30 1999-05-07 Michel Delmas Preparation of paper pulp from lignocellulose material
WO2000044699A1 (en) * 1999-01-29 2000-08-03 Ecovac Pyrocycling Technologies Inc. Process for the production of phenolic-rich pyrolysis oils for use in making phenol-formaldehyde resol resins

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9963673B2 (en) 2010-06-26 2018-05-08 Virdia, Inc. Sugar mixtures and methods for production and use thereof
US9410216B2 (en) 2010-06-26 2016-08-09 Virdia, Inc. Sugar mixtures and methods for production and use thereof
US10752878B2 (en) 2010-06-26 2020-08-25 Virdia, Inc. Sugar mixtures and methods for production and use thereof
US11242650B2 (en) 2010-08-01 2022-02-08 Virdia, Llc Methods and systems for solvent purification
US10876178B2 (en) 2011-04-07 2020-12-29 Virdia, Inc. Lignocellulosic conversion processes and products
US9512495B2 (en) 2011-04-07 2016-12-06 Virdia, Inc. Lignocellulose conversion processes and products
US11667981B2 (en) 2011-04-07 2023-06-06 Virdia, Llc Lignocellulosic conversion processes and products
US9783861B2 (en) 2012-05-03 2017-10-10 Virdia, Inc. Methods for treating lignocellulosic materials
US11053558B2 (en) 2012-05-03 2021-07-06 Virdia, Llc Methods for treating lignocellulosic materials
US9657146B2 (en) 2013-03-14 2017-05-23 Virdia, Inc. Methods for treating lignocellulosic materials
US9988412B2 (en) 2013-05-03 2018-06-05 Virdia, Inc. Methods for preparing thermally stable lignin fractions
US10138332B2 (en) 2013-05-03 2018-11-27 Virdia, Inc. Methods for treating lignocellulosic materials
US9683005B2 (en) 2013-05-03 2017-06-20 Virdia, Inc. Methods for preparing thermally stable lignin fractions
US10767308B2 (en) 2014-07-09 2020-09-08 Virdia, Inc. Methods for separating and refining lignin from black liquor and compositions thereof

Also Published As

Publication number Publication date
US20110173875A1 (en) 2011-07-21
CN101932670A (en) 2010-12-29
DK2190949T3 (en) 2012-05-21
RU2476581C2 (en) 2013-02-27
EP2025735A1 (en) 2009-02-18
RU2010109383A (en) 2011-09-20
PL2190949T3 (en) 2012-11-30
US8673027B2 (en) 2014-03-18
CA2696268C (en) 2015-11-24
CA2696268A1 (en) 2009-02-19
CN101932670B (en) 2014-04-02
EP2190949B1 (en) 2012-04-18
EP2190949A2 (en) 2010-06-02
WO2009021733A2 (en) 2009-02-19
BRPI0815466A2 (en) 2015-08-25
ATE554153T1 (en) 2012-05-15

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