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WO2019068918A1 - Procédés de traitement de matériau lignocellulosique - Google Patents

Procédés de traitement de matériau lignocellulosique Download PDF

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Publication number
WO2019068918A1
WO2019068918A1 PCT/EP2018/077232 EP2018077232W WO2019068918A1 WO 2019068918 A1 WO2019068918 A1 WO 2019068918A1 EP 2018077232 W EP2018077232 W EP 2018077232W WO 2019068918 A1 WO2019068918 A1 WO 2019068918A1
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Prior art keywords
lignin
derived
process stream
optionally
cellulose
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Ceased
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PCT/EP2018/077232
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WO2019068918A8 (fr
Inventor
Peter Geigle
Jan HARTWIG
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CMBlu Projekt AG
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CMBlu Projekt AG
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Priority claimed from PCT/EP2017/075987 external-priority patent/WO2019072386A1/fr
Priority claimed from PCT/EP2017/075985 external-priority patent/WO2019072385A1/fr
Application filed by CMBlu Projekt AG filed Critical CMBlu Projekt AG
Priority to PCT/EP2019/053605 priority Critical patent/WO2019158616A1/fr
Publication of WO2019068918A1 publication Critical patent/WO2019068918A1/fr
Publication of WO2019068918A8 publication Critical patent/WO2019068918A8/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
    • H01M8/184—Regeneration by electrochemical means
    • H01M8/188—Regeneration by electrochemical means by recharging of redox couples containing fluids; Redox flow type batteries
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00—Preparation of cellulose ethers
    • C08B11/02—Alkyl or cycloalkyl ethers
    • C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
    • C08B11/08—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with hydroxylated hydrocarbon radicals; Esters, ethers, or acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00—Preparation of cellulose ethers
    • C08B11/02—Alkyl or cycloalkyl ethers
    • C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
    • C08B11/10—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals
    • C08B11/12—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals substituted with carboxylic radicals, e.g. carboxymethylcellulose [CMC]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00—Preparation of cellulose ethers
    • C08B11/193—Mixed ethers, i.e. ethers with two or more different etherifying groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B3/00—Preparation of cellulose esters of organic acids
    • C08B3/06—Cellulose acetate, e.g. mono-acetate, di-acetate or tri-acetate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B5/00—Preparation of cellulose esters of inorganic acids, e.g. phosphates
    • C08B5/02—Cellulose nitrate, i.e. nitrocellulose
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H8/00—Macromolecular compounds derived from lignocellulosic materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/10—Esters of organic acids, i.e. acylates
    • C08L1/12—Cellulose acetate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/16—Esters of inorganic acids
    • C08L1/18—Cellulose nitrate, i.e. nitrocellulose
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/26—Cellulose ethers
    • C08L1/28—Alkyl ethers
    • C08L1/284—Alkyl ethers with hydroxylated hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/26—Cellulose ethers
    • C08L1/28—Alkyl ethers
    • C08L1/286—Alkyl ethers substituted with acid radicals, e.g. carboxymethyl cellulose [CMC]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/005—Lignin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10B—DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS
    • C10B53/00—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form
    • C10B53/02—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form of cellulose-containing material
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • 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
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel
    • 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
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel
    • 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
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells

Definitions

  • substituted is contemplated to include substitution with all permissible substituents of organic compounds, and includes any of the substituents described herein that results in the formation of a stable compound.
  • Compounds described herein contemplates any and all such combinations in order to arrive at a stable compound.
  • Heteroatoms such as nitrogen may have hydrogen substituents and/or any suitable substituent as described herein which satisfy the valencies of the heteroatoms and results in the formation of a stable moiety.
  • Compounds described herein are not intended to be limited in any manner by the exemplary substituents described herein.
  • an aryl group has 10 ring carbon atoms ("do aryl”; e.g., naphthyl such as 1 - naphthyl and 2-naphthyl).
  • an aryl group has 14 ring carbon atoms ("CM aryl”; e.g., anthracyl).
  • CM aryl e.g., anthracyl
  • Aryl also includes ring systems wherein the aryl ring, as defined above, is fused with one or more carbocyclyl or heterocyclyl groups wherein the radical or point of attachment is on the aryl ring, and in such instances, the number of carbon atoms continue to designate the number of carbon atoms in the aryl ring system.
  • carbonyl refers to a group which contains a carbon atom connected with a double bond to an oxygen or a sulfur atom.
  • moieties which contain a carbonyl include aldehydes, ketones, carboxylic acids, amides, esters, anhydrides, etc.
  • esteer refers to groups or molecules which contain a carbon or a heteroatom bound to an oxygen atom which is bonded to the carbon of a carbonyl group.
  • ester includes alkoxycarboxy groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, etc.
  • halo or halogen refers to fluorine (fluoro, -F), chlorine (chloro, -CI), bromine (bromo, -Br), or iodine (iodo, -I) groups.
  • thiol or “sulfhydryl” refers to a -SH group.
  • C-C linkages may occur in natural lignin, such as context5-5", congestionbeta-5", congestionbeta-beta” and strictbeta- 1 ", amongst which the penal5-5" linkage is the most frequently seen C-C linkage, in particular in softwood, such as spruce.
  • Typical linkages as affirmbeta-0-4", disregard4-0-5" and formula5-5" are depicted in the following:
  • the term grasplignin-derived has the broadest meaning with regard to any lignin, which underwent one or more process steps, from process step (1 ) onwards, according to the present invention.
  • a wrinklederived material has to be understood as a chemical derivative.
  • a FAQlignin-derived” material may be of any molecular weight smaller than the natural lignin polymer, including a small molecule, i.e. a low molecular weight compound as used herein.
  • both strictlyified lignin-derived components” and among the present invention are lignin-derived material.
  • a Pope-derived modified lignin-derived component or a (target or precursor) compound as defined herein is a (macro-)molecule, which corresponds to or is derived from a (monomeric) building block of natural lignin or is a homo- or heterodimers of such (monomeric) building blocks.
  • Such compounds are derived from natural lignin via its modification in step (1 .2) onwards, which provides the fraction of modified lignin-derived components as intermediates of the inventive method.
  • FIG. 2 shows a preferred sequence of method steps according to the inventive method.
  • step 1 l ignocellulosic material is provided and optionally prepared as described herein.
  • step 2) the (prepared) lignocellulosic material is subjected to a pulping process and pulp separation step.
  • Step 2) is preferably used to separate the cel lulose fraction from the l ignin fraction in the mai n process stream A.
  • the pulping process preferably yields a cel lulose-derived process stream A (left) and a l ignin-derived process stream A (right).
  • the cellulose-derived process stream A orußpulp" essential ly comprises a mixture of
  • R 1 -R 18 are each independently selected from hydrogen; hydroxy!; carboxy; optionally substituted G- 6 alkyl optionally comprising at least one heteroatom selected from N, O and S, including -C n H 2 nOH, -C n H 2n NH 2 and -C n H 2n S03H ; wherein n is an integer selected from 1 , 2, 3, 4, 5, or 6; carboxylic acids; esters; halogen; optionally substituted G-6 alkoxy, including methoxy and ethoxy; optionally substituted amine, including primary, secondary, tertiary and quaternary amines, in particular -NH 2 /NH 3 + , -NHR/NH 2 R + , -NR 2 /NHR 2 + and -NR 3 + , where R is H or optionally substituted G- 6 alkyl optionally comprising at least one heteroatom selected from N, O and S, including -CnH 2n OH,
  • the inventive method may comprise an additional step of:
  • the lignocellulosic material provided in step 1 ) of the inventive method is preferably selected or derived from soft- or hardwoods. More preferably, said lignocellulosic material may be selected or derived from wood of low silica and resin content, even more preferably from northern woods, most preferably from beech, pine, birch, eucalyptus or spruce.
  • the preferred salt is calcium bisulphite, which may advantageously be employed, if the selected pH value for the sulphite process is 2.5 or less.
  • Higher pH sulphite pulping (at a pH above pH 2.5 or, more specifically, above pH 4) generally employs monovalent ions, such as sodium or ammonium, as counter cations. However, it is not excluded that sulphite pulping may be carried out over a wider pH range, including alkaline conditions of about pH 7 to12.
  • the Jiquor" used in sub-step (ii) of the sulphite process may be provided as follows: Sulphur may be oxidized (burnt) with the stochiometrically adequate amount of oxygen to yield sulphur dioxide. Sulphur dioxide is preferably added, e.g. as a gas, to water to give sulphurous acid, which may be further diluted for its use as contextpulping liquor".
  • Step (2) of the inventive method may alternatively include pulping by using the organosolv process.
  • the organosolv process typically involves treatment of wood or bagasse with various organic solvents.
  • further lignin-derived process streams B, C, D... may be separated from the main process stream A.
  • These further process stream(s) may (in part) be subjected to the same method step(s), for instance the same chemical decomposition step(s) 5), as the main process stream A.
  • processing of the further lignin-derived process streams B, C, D... may typically diverge from the processing of the main process stream A at some point to obtain different valuable products therefrom.
  • Said reaction type is typically known as annulation, which serves in organic chemistry as a chemical reaction, which allows to anneal two aromatic (mono-, di- or n-aromatic) ring systems.
  • the two or more precursor molecules of the annulation reaction are both or all e.g. monomeric or dimeric target compounds.
  • each of R 2 -R 7 of Formula (c) is independently selected from H, optionally substituted G-6 alkyl, optionally substituted G-e alkenyl, halogen, optionally substituted G- 6 aIkoxy, amino, nitro, phosphoryl, phosphonyl, wherein at least one of R 2 , R 4 , R 5 , and R 7 is hydroxy or G- 3 alkoxy, and R 1 and/or R 8 of Formula (c) is/are selected from the group consisting of hydrogen, hydroxy, linear or branched G- 6 carboxyl, linear or branched G- 6 aldehyde, linear or branched G-6 ketone, and linear or branched G-6 alcohol,
  • Friedel-Crafts acylation reactions include the acylation of aromatic rings with an acyl chloride using a strong Lewis acid catalyst. Friedel-Crafts acylation is also possible with acid anhydrides. This reaction typically involves the acylation of an aromatic ring with an alkyl halide using a strong Lewis acid catalyst, e.g. an anhydrous ferric chloride as a catalyst.
  • a strong Lewis acid catalyst e.g. an anhydrous ferric chloride as a catalyst.
  • each of R ⁇ R is independently selected from optionally substituted G-6 alkyl, optionally substituted G- 6 alkenyl, halogen, optionally substituted G-6 alkoxy, amino, carboxyl, nitro, phosphoryl, and phosphonyi;
  • Combined cracking and oxidation may be achieved by electro-oxidation or catalyzed oxidation as described in the context of chemical decomposition in step 4) of the inventive method.
  • a solution comprising modified lignin-derived components (A) may be diluted to a concentration below 20% (w/w), preferably below 10% (w/w), more preferably below 5% (w/w), even more preferably below 2% (w/w) and be subjected to electro-oxidation, and the pH optionally be adjusted to acidic conditions, or alternatively to alkaline conditions (pH 1 1 -14, preferably at least pH 13).
  • step 7) of the inventive method may preferably yield a lignin-derived composition comprising at least one sulfonated low molecular weight aromatic lignin-derived quinone compound.
  • Lignocellulosic material is provided and optionally prepared as described in the context of step 1 ) above. Subsequently, said lignocellulosic material is subjected to pulping, preferably to Kraft or sulphite pulping, as described in the context of step 2) above.
  • process stream B may be separated from any other of the process streams described herein.
  • heterogenous catalysts comprising or consisting of metals or metal oxides, the metals preferably being selected from, without limitation, platinum (Pt), nickel (Ni), iron (Fe), rhenium (Re), titanium (Ti), manganese (Mn), or combinations thereof, such as Cu-Ni-Ce or Cu-Mn.
  • electrocatalysis may be applied, where lignin or its derivatives are oxidized at the surface of an electrocatalyst (e.g. a Pt, Au, Cu, or Ni electrode) in a suitable solvent such as methanol.
  • Vani llin can thus be considered as a difunctional compound, which is useful to prepare thermoplastic polymers. It is available on an industrial scale from well-described, ever improving processes. Thus, vanil lin has the potential to be a key renewable aromatic building block for the production of valuable chemical compounds and products, such as renewable polymers.
  • Syringaldehyde is a valuable starting material for the pharmaceutical industry, as it is a precursor for 3, 4,5-trimethoxybenzaldehyde.
  • Process stream D may be separated from the process stream A of the inventive method, typically prior to or after step 1 ) (provision and optionally preparation of lignocellulosic material), or alternatively after step 2) (pulping), after step 4) (isolation/purification of modified lignin- derived components) or after step 5) (chemical decomposition) or step 6) (isolation/purification of low molecular weight lignin-derived compounds).
  • process stream D may be separated from any other of the process streams described herein.
  • the catalytic cracking of lignin or its derivatives of process stream D may be accomplished using optimized zeolites in an acid-catalyzed reaction.
  • Hydrolysis of lignin or its derivatives may be accomplished by subjecting lignin or its derivatives of process stream D to alkaline hydrolysis in supercritical water, KOH in supercritical methanol or ethanol; or NaOH and Ca(OH) 2 .
  • Process stream G may be subjected to downstream processing to obtain porous carbon, as e.g. described by Zhang et al. ChemSusChem 2015, 8:428-432..
  • Vanillin of e.g. any of process streams A, B or C may be further chemically derivatized, e.g. oxidized, to yield a benzoquinone compound.
  • the oxidation reaction may e.g. be implemented as step 7) following step 6) of the inventive method.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Sustainable Development (AREA)
  • Sustainable Energy (AREA)
  • Electrochemistry (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Paper (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne de nouveaux procédés de traitement de matériau lignocellulosique. Plus spécifiquement, l'invention démontre une approche intégrée pour traiter la cellulose afin d'obtenir du papier et de la pâte et valoriser la lignine afin d'obtenir des produits chimiques et des produits à valeur ajoutée.
PCT/EP2018/077232 2017-10-05 2018-10-05 Procédés de traitement de matériau lignocellulosique Ceased WO2019068918A1 (fr)

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PCT/EP2019/053605 WO2019158616A1 (fr) 2018-02-13 2019-02-13 Nouveaux procédés de traitement de matériau lignocellulosique

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EP2017001177 2017-10-05
EPPCT/EP2017/001177 2017-10-05
PCT/EP2017/075987 WO2019072386A1 (fr) 2017-10-11 2017-10-11 Nouveaux procédés de traitement de matériau lignocellulosique
EPPCT/EP2017/075985 2017-10-11
PCT/EP2017/075985 WO2019072385A1 (fr) 2017-10-11 2017-10-11 Électrolytes de batterie redox
EPPCT/EP2017/075987 2017-10-11
EPPCT/EP2018/053601 2018-02-13
EP2018053600 2018-02-13
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US12479876B2 (en) 2019-12-20 2025-11-25 Andritz Oy Method of removing volatile compounds from a lignin-containing material, use of a distillation method, and a lignin-containing material

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CN111647090A (zh) * 2020-07-14 2020-09-11 北京理工大学 一种用废酸硝化竹纤维素的方法
CN118791380B (zh) * 2024-09-12 2024-11-22 浙江尔格能源有限公司 有机活性负极材料、有机负极电解液及有机液流电池

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US12479876B2 (en) 2019-12-20 2025-11-25 Andritz Oy Method of removing volatile compounds from a lignin-containing material, use of a distillation method, and a lignin-containing material
CN114773489A (zh) * 2022-05-19 2022-07-22 浙江三和食品科技有限公司 一种低粘度羧甲基纤维素钠的制备方法
CN114773489B (zh) * 2022-05-19 2023-02-24 浙江三和食品科技有限公司 一种低粘度羧甲基纤维素钠的制备方法

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