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EP2294230A1 - Décomposition de matériaux contenant des hydrates de carbone avec des catalyseurs inorganiques - Google Patents

Décomposition de matériaux contenant des hydrates de carbone avec des catalyseurs inorganiques

Info

Publication number
EP2294230A1
EP2294230A1 EP09780013A EP09780013A EP2294230A1 EP 2294230 A1 EP2294230 A1 EP 2294230A1 EP 09780013 A EP09780013 A EP 09780013A EP 09780013 A EP09780013 A EP 09780013A EP 2294230 A1 EP2294230 A1 EP 2294230A1
Authority
EP
European Patent Office
Prior art keywords
carbohydrate
containing material
catalyst
inorganic
building blocks
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.)
Withdrawn
Application number
EP09780013A
Other languages
German (de)
English (en)
Inventor
Ulrich Kettling
Andre Koltermann
Michael Kraus
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.)
Sued Chemie IP GmbH and Co KG
Original Assignee
Sued Chemie AG
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
Application filed by Sued Chemie AG filed Critical Sued Chemie AG
Publication of EP2294230A1 publication Critical patent/EP2294230A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K1/00—Glucose; Glucose-containing syrups
    • C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
    • C13K1/04—Purifying
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K1/00—Glucose; Glucose-containing syrups
    • C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials

Definitions

  • the production of bio-based chemical components from renewable sources is becoming increasingly important due to the global limitation of fossil petrochemical raw materials.
  • the preferred starting materials for the production of chemical products on a biological basis are derived from renewable plant biomass.
  • cabohydrhydrate-containing materials are the most important representatives in the group of biological polymers, which are typically referred to as "biomass”.
  • biomass The world annual production through photosynthesis of plants is estimated at 1.3 x 10 9 tons.
  • LCB differs from first generation biological raw materials in its complex chemical and structural composition.
  • the main constituents of LC3 are high polymer materials such as celulose (about 35-50% by weight), hemicilulose (about 20-35% by weight) and lignins (about 10-25% by weight).
  • the celulose is a polysaccharide of ⁇ -1,4-glycosidically linked glucose monomers, which is predominantly present in the plant kingdom and usually occurs there with other builder substances.
  • Native Celiulose Native Celiulose
  • ' is from about 8,000 to 12,000 glucose units, corresponding to a molecular weight of 1.3 to 2.0 million.
  • Purified Celite is a colorless substance which is insoluble in water and most organic solvents. In nature, celulose never occurs as a single chain but always as a crystalline aggregate of many parallel oriented chain microfibrils.
  • depolymerization products can be used both as raw materials for the production of further products, eg. B. serve in chemical synthesis processes, as well in biotechnological. Transformations and in the chemical, cosmetic or pharmaceutical industry and the food industry use.
  • glucose derived from depolymerization of carbohydrate-containing materials is a versatile starting material for the production of high-quality chemical intermediates, such as sorbitol, lactate, and ethanol.
  • Pentose sugars derived from hemicellulose fractions, such as xylose and arabmose serve as starting material for high-quality sugar alcohols, such as xyI it and arabimt.
  • the natural structure of the cellulose causes a high resistance of the cellulose to a Depolyme ⁇ sation. This applies both to chemical and enzymatic as well as to microbial depolymerization.
  • US 5,221,357-A and US 5,536,325-A describe a two-stage process for the acid hydrolysis of lignocellulosic material to glucose using dilute acids at high temperatures.
  • hemicellulose is polymerized into xylose and other sugars
  • cellulose is converted into glucose.
  • the low acidity reduces the economic need for chemical recovery, but the maximum achievable glucose content is low.
  • cellulose conversion processes have been developed which involve mechanical and / or chemical pretreatment and enzymatic hydrolysis.
  • the purpose of the pretreatment is to destroy the fiber structures and to improve the accessibility of the starting material for the cellulase enzymes used in the hydrolysis step.
  • the mechanical pre-treatment typically involves the use of pressure, grinding, milling, stirring, shredding, compression / expansion or other types of mechanical action.
  • Chemical pretreatment typically involves the use of heat, often steam, acid, alkalis and solvents. This combination of pretreatment with enzymatic hydrolysis is associated with high costs and has not been economically competitive.
  • JP 2006-129735 glucose is converted with catalytic Depolyme ⁇ sationsverfah- ren cellulose-containing materials with the addition of a carbon catalyst at temperatures of cypischholder over 100 0 C and less than 300 0 C.
  • the technical problem is to provide a method of producing valuable LCB chemical building blocks which avoids the disadvantages and disadvantages of the prior art
  • the invention relates to a process for the preparation of basic chemicals or chemical building blocks from polymeric or oligomeric carbohydrate-containing materials such as LCB.
  • soluble monomeric or oligomeric building blocks are liberated from carbonate hydrate-containing material: by mixing the carbohydrate-containing material with an inorganic catalyst, preferably a Tectosili ⁇ at, phyllosilicate or hydrotalcite, in a solvent system m contact; is brought
  • the problems arising from the prior art are solved by contacting carbohydrate-containing materials with suitable inorganic catalysts and by suitable solvent systems and, under mild ambient conditions, reacting in shorter chains and mono- and oligomeric carbohydrates performed w._rd.
  • the present invention provides a process for the catalytic treatment of a carbohydrate-containing material comprising the following steps: (a) treating the carbohydrate-containing material with an inorganic catalyst, ( ⁇ ) releasing defined monomeric or oligomeric components from the polymeric carbohydrate-containing material Material through the Kaca- lysator, and (c) separating the m or monomeric or oligomeric building blocks produced in step (b) from the residue of the conventially hydrate-containing material
  • An advantage of the present invention is the fact that it can be dispensed with expensive enzymes for the depolymerization of carbohydrate nalt materials.
  • a carbonylate-containing material is treated with an inorganic catalyst in order to liberate defined monomeric or oligomeric building blocks from the carbohydrate-containing material
  • carbohydrate-containing material includes carbohydrate-containing pure substances, mixtures of various carbon hydrates, and complex mixtures of substrates containing carbohydrates. Carbohydrate-containing material further includes, but is not limited to, waste products from the forestry and agricultural and food processing industries as well as municipal waste.
  • the carbohydrate-containing materials include in particular "lignocellulosic biomass” or “LCBs”. This is to be understood as meaning carbohydrate-containing material containing cellulose, hemicellulose and lignite.
  • the insoluble fraction of LCB usually contains significant amounts of polymeric substrates, such as cellulose, xylan, mannan In addition, it contains polymeric substrates such as lignm, arabmoxylan, glucoronoxylan, glucomarman and xyloglucan
  • LCBs from agriculture include, but are not limited to, wheat straw, corn stron, ruminant manure from ruminants, sugar Rhausen press cake, sugar beet pulp and herbaceous materials such as European grass, Sencea Lespedeua Serala and Sudan grass.
  • LCBs in the form of forestry waste products include, but are not limited to, tree bark, hacking cuttings and wood waste.
  • LCMs in the form of raw substrates from the food industry but are not limited to fruit pulps, agave backpresses, coffee residues and mill residues, such as rapeseed presscake and mill wastewater.
  • LCBs in the form of raw substrates from the pulp and paper industry include, but are not limited to pulp and paper mill effluents.
  • LCBs in the form of raw substrates from municipal waste include, but are not limited to, paper waste, vegetable residues and fruit residues.
  • the carbohydrate-containing material is cellulose- and / or hemicellulose-containing material, in particular one or more LCBs.
  • the carbohydrate-containing material Before the treatment according to the invention with the catalyst, the carbohydrate-containing material can be ground.
  • the inorganic catalyst is preferably a silicate or clay material which is preferably doped with foreign ions.
  • tectosilicate as used in the present invention includes any tectosilicate known to those skilled in the art, and especially any zeolites. Possible structures and examples of numerous tectosilicates and, in particular, zeolites are described, for example, in "Holleman-Wiberg, Textbook of Inorganic Chemistry” by N. Wiberg, 91.-100. Ed., Walter de Gruyter & Co., 1985, ISBN 3-11-007511-3, pp. 776-778. Zeolites and itire representation are also in the "R ⁇ mpp Lexikon chemistry", eds.: J. Falbe, M. Regitz, 10 ed. 1999, Georg Thieme publishing house, ISBN 3-13-107830-8, P.
  • the term "tectosilicate” includes all compounds in which xv of the spatial network structure of the silicon dioxide silicon atoms are replaced by other atoms, in particular Aluirir.iurr. Preferably, at least 1%, preferably at least 5%, more preferably at least 8%, more preferably at least 12%, of the silicon atoms of the tectosilicate may be replaced by alumium atoms.
  • a tectosilicate, in particular a zeolite, cavities and / or channels may be used The cavities may, for example, have a diameter of 350 to 1300 pm and the channels may have a diameter of 180 to 800 pm.
  • the one or more tectosilicates may be one or more zeolites Mixtures of zeolite (s) with other Tectosilicaten act
  • the inorganic catalyst may comprise or consist of one or more zeolites, for example besides optional other tectosilicates.
  • the inorganic catalyst comprises one or more zeolites selected from the group consisting of fiber zeolites, leaves Zeolites, zeolites of the MFI structure type, zeolites A, zeolite X, zeolite Y and mixtures thereof are selected.
  • zeolites and others Natrolicn, laumontite, mordenite, thomsonite, to Elatter zeolites and others, heulandite, stilbite, as well as to zeolite zeolites and the like. Faujasite, chabazite and gmelimt
  • phyllosilicate as used in the present invention includes, for example, the phyllosilicate known to those skilled in the art, and more particularly 3eglbc smectitic silicate - S - to "Rompp-Lexikon Chemie", eds.: J. Falbe, M. Regitz, 10th ed. 199S / 199S, Georg Thieme Verlag, ISBN 3-13-107830-8, p 3328/3329 and S 4128.
  • Particularly preferred phyllosilicates are bentontites, the major mineral of which is montmorillonite, and other montmorillonite-containing phyllosilicates, as well as other smectite clay minerals, such as silicate, saponite, glauconite, nontronite, and hectorite.
  • the phyllosilicates or bentonites used according to the invention preferably contain from 70 to 80% by weight of montmorillonite.
  • Especially preferred bentonites are acid activated bentonites.
  • Also particularly preferred bentonites are alkaline activated bentonites.
  • Bentonites show surprisingly better properties with respect to the concentration and temperature ranges necessary for a catalytic depolymerization compared with the known carbon catalysts. Also, the amounts of catalyst necessary for a depolymerization in the inventive method are significantly lower than for the known carbon catalysts.
  • hydrotalcites is familiar to the person skilled in the art and refers to synthetically produced aluminum-magnesium hydroxycarbonates.
  • inorganic catalysts contain, in addition to Al, further elements of main group 3 such as Ga, B or In.
  • Suitable counterions for the produced by the trivalent framework cations excess negative charge can be H +, Ka +, Li +, K +, Rb +, Cs +, NH 4 +, Mg 2+, Ca 2+, Sr 2+ and Ba + in Catalyst be included.
  • the catalysts can furthermore contain, in addition to Si, further elements of the 4th main group or side group such as Ti, Ge or Sn.
  • the inorganic catalysts are doped with foreign ions or impurities prior to use by methods known to those skilled in the art.
  • the Foreign ions or foreign atoms can be applied wet-chemically in the form of aqueous, organic or orgasmic aqueous solutions of their salts by impregnating the catalysts with the salt solution.
  • the wet chemical treatments close to Typically, the drying under vacuum at about 100 "C and out the Calci ⁇ ie- tion at about 400 to 800, but preferably below 600 0 C to, for example, 0.1 to 24 Scunden.
  • the foreign ions may furthermore can also be applied dry-chemically to the catalysts, for example by precipitating a gaseous compound which is gaseous at relatively high temperatures onto the catalyst, preferably nickel, CoDaIt, platinum, palladium, gallium or indium are used as foreign ions, platinum hac being especially suitable for zeolite
  • the doping with foreign ions is preferably carried out in an amount of from 0.1 to 10% by weight, more preferably from 0.2 to 5% by weight, based on the weight of the silicate. or Tontnaterials.
  • activated carbon is not considered to be an inorganic catalyst.
  • inorganic catalysts further exclude catalysts having at least one C-H bond.
  • the catalyst is preferably present in a particulate form, more preferably in a particle size of from 1 to 100 ⁇ tn.
  • the catalyst is preferably used in the process according to the invention in an amount of from 1 to 20% by weight, preferably 2 to 15% by weight, more preferably 6 to 12% by weight, based on the material containing carbohydrate ,
  • the depolymerization is carried out at low temperatures and pressures.
  • the temperatures are preferably between 20 0 C and 400 0 C, more preferably between 2O 0 C and 15O 0 C, particularly preferred between 100 0 C and 140 0 C.
  • the pressure is preferably between 20 0 C and 400 0 C, more preferably between 2O 0 C and 15O 0 C, particularly preferred between 100 0 C and 140 0 C.
  • 0 bar and 200 bar more preferably between 0 bar and 5 bar.
  • the carbohydrate-containing material is present in a solvent system.
  • the solvent system is preferably one or more organic or inorganic solvents. Particularly preferred are water or alcohols having 2 to 6 carbon atoms.
  • the solvent system is an aqueous system which preferably contains solubilizers, such as detergents.
  • the solvent system further contains at least one acid, in particular a strong inorganic acid, more preferably acid (HCl) or sulfuric acid.
  • the amount of acid in the solvent system is between about 0.1 and 5 weight percent, more preferably between about 0.5 and 2 weight percent based on the total amount of solvent system.
  • the solvent is in an amount of 1 to 10 liters, preferably 2 to 5 liters, added per 1 kg of carbohydrate-containing material.
  • detergent includes all detergents that increase the solubility behavior of cellulosic materials in liquid solvent systems.
  • this includes nonionic, anionic, cationic and amphoteric detergents.
  • Particularly suitable anionic detergents include alkyl (ether) sulfates such as lauryl sulfate or lauryl ether sulfate.
  • Non-ionic detergents include in particular polyethylene ethers or polypropylene ethers such as Tween 20 or Triton-X 100, but also triethanolamine. The detergents are preferably used in an amount of from 0.1 to 0.5% by weight, based on the solvent.
  • monomeric or oligomeric building blocks are liberated from the material which contains carbonyl hydrydrate.
  • the term “monomeric or oligomeric building blocks” refers to monomeric or oligomeric products that are released from the carbohydrate-containing material using an inorganic catalyst.
  • oligomer includes compounds having at least two and / or up to 20 monomeric units.
  • release or “depolymerize” means the conversion of a polymeric substrate into soluble monomeric or oligomeric building blocks by a physical, chemical or catalytic process, such as hydrolysis, oxidative or reductive depolymerization, and other methods known to those skilled in the art.
  • the defined monomer (s) or oligomeric component (s) released from the carbohydrate-containing crude substrate in step (b) is glucose, xylose, arabinose and / or oligomers , which are composed of monomeric glucose building blocks.
  • the monomeric and / or oligomeric building blocks are separated from the remainder of the carbohydrate-containing material.
  • these building blocks are soluble in the solvent, so that the separation by liquid / solid separation of the soluble building blocks in the aqueous medium from the insoluble carbohydrate-containing crude substrate can be performed.
  • the physico-chemical treatment step comprises a treatment with aqueous solvents, organic solvents, or any combination or mixture thereof, preferably with ethanol or glycerol.
  • Another aspect of the present invention relates to the use of an inorganic catalyst, in particular selected from the group consisting of the Tectosilicaten, the Phyliosilicaten, the hydrotalcites and their mixtures for the treatment, in particular for the depolymerization of a carbohydrate-containing material.
  • an inorganic catalyst in particular selected from the group consisting of the Tectosilicaten, the Phyliosilicaten, the hydrotalcites and their mixtures for the treatment, in particular for the depolymerization of a carbohydrate-containing material.
  • Example 1 Ig cellulose (Avicel PH-101, Pluka, Buchs) is distilled with 100 mg of the zeolite Wàith DAY P (Degussa / Evonic, Essen) as an inorganic catalyst and 2 ml H 2 O dest. with or without addition of 1% HCl in a pressure vessel (5 ml) and stirred for 1 min at 20 ° C. This mixture is then heated to 12O 0 C for 20 min. After cooling the mixture to room temperature, the solid and liquid phases are separated by centrifugation. The content of Ceiluiose in the solid phase is determined by gravimetric drying and the content of glucose in the liquid phase by HPLC (Aminex HPX-87C, Bio-Rad, Kunststoff). The yield of glucose is increased by up to 35% compared to a batch without addition of the catalyst on a molar basis.
  • Example 4 Ig of an acid-dealuminated bentonite 'Tonsil Supreme HOF, Sud-Chemie, Kunststoff) is sprayed with 20 ⁇ l of a 25% gallium sulfate solution. The impregnated bentomet is dried for 24 hours at 120 ° C. Ig cellulose (Avicel PH-101, Fluka, Bucns ) is reacted with 100 mg of the above-described Ga-exchanged bentonite and 2 ml of H 2 O. least. with or without the addition of 1% HCl in a pressure vessel (5 ml) and stirred for 1 min at 2O 0 C stirred. This mixture is then heated to 11O 0 C for 20 min.
  • the solid and liquid phases are separated by centrifugation.
  • the content of cellulose in the solid phase is determined gravimetrically after drying and the content of glucose is determined by HPLC (Aminex HPX-87C, Bio-Rad, Kunststoff).
  • the yield of glucose in the liquid phase is increased by up to 75% compared to a batch without addition of the catalyst on a molar basis.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de dépolymérisation de matériaux contenant des hydrates de carbone, qui comprend les étapes suivantes: (a) traitement d'un matériau contenant des hydrates de carbone avec un catalyseur inorganique pour libérer des unités monomères ou oligomères définies du matériau contenant des hydrates de carbone; (b) séparation des unités monomères ou oligomères définies produites à l'étape (a) du reste du matériau contenant des hydrates de carbone. Le catalyseur inorganique utilisé à l'étape (a) comprend de préférence des tectosilicates, des phyllosilicates ou des hydrotalcites, mieux encore des zéolithes ou des bentonites. En outre, le matériau contenant des hydrates de carbone comprend de préférence du LCB et les unités monomères ou oligomères définies, de préférence du glucose, du xylose, de l'arabinose et leurs oligomères. D'autres aspects de l'invention concernent l'utilisation d'agents de solubilisation conjointement avec le catalyseur inorganique.
EP09780013A 2008-06-30 2009-06-30 Décomposition de matériaux contenant des hydrates de carbone avec des catalyseurs inorganiques Withdrawn EP2294230A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008030892A DE102008030892A1 (de) 2008-06-30 2008-06-30 Abbau von kohlehydrathaltigen Materialien mit anorganischen Katalysatoren
PCT/EP2009/058144 WO2010009958A1 (fr) 2008-06-30 2009-06-30 Décomposition de matériaux contenant des hydrates de carbone avec des catalyseurs inorganiques

Publications (1)

Publication Number Publication Date
EP2294230A1 true EP2294230A1 (fr) 2011-03-16

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EP09780013A Withdrawn EP2294230A1 (fr) 2008-06-30 2009-06-30 Décomposition de matériaux contenant des hydrates de carbone avec des catalyseurs inorganiques

Country Status (5)

Country Link
US (1) US20110152514A1 (fr)
EP (1) EP2294230A1 (fr)
JP (1) JP2011526484A (fr)
DE (1) DE102008030892A1 (fr)
WO (1) WO2010009958A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT2643485E (pt) * 2010-11-25 2014-11-13 Studiengesellschaft Kohle Mbh Método para a despolimerização catalisada com ácido de celulose
WO2014007295A1 (fr) * 2012-07-03 2014-01-09 昭和電工株式会社 Procédé de décomposition de biomasse végétale, et procédé de fabrication de glucose
US9790249B2 (en) 2012-10-05 2017-10-17 Alliance For Sustainable Energy, Llc Hydroxide catalysts for lignin depolymerization
US9631146B2 (en) * 2012-10-05 2017-04-25 Alliance For Sustainable Energy, Llc Hydroxide catalysts for lignin depolymerization
MX391237B (es) 2016-02-19 2025-03-21 Intercontinental Great Brands Llc Procesos para crear multiples flujos de valores a partir de fuentes de biomasa

Citations (2)

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WO2007100052A1 (fr) * 2006-03-01 2007-09-07 National University Corporation Hokkaido University Catalyseur d'hydrolyse de cellulose et/ou de reduction du produit d'hydrolyse et procede de production d'un alcool sucre a partir de la cellulose

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EP0329923A1 (fr) * 1988-02-22 1989-08-30 Fina Research S.A. Procédé catalytique en une étape de conversion directe de polysaccharides en alcools polyhydroxylés
WO2007100052A1 (fr) * 2006-03-01 2007-09-07 National University Corporation Hokkaido University Catalyseur d'hydrolyse de cellulose et/ou de reduction du produit d'hydrolyse et procede de production d'un alcool sucre a partir de la cellulose
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Also Published As

Publication number Publication date
WO2010009958A1 (fr) 2010-01-28
US20110152514A1 (en) 2011-06-23
JP2011526484A (ja) 2011-10-13
DE102008030892A1 (de) 2009-12-31

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