WO2020192432A1 - Procédé de décomposition catalytique d'une matière brute lignocellulosique - Google Patents

Procédé de décomposition catalytique d'une matière brute lignocellulosique Download PDF

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Publication number
WO2020192432A1
WO2020192432A1 PCT/CN2020/078914 CN2020078914W WO2020192432A1 WO 2020192432 A1 WO2020192432 A1 WO 2020192432A1 CN 2020078914 W CN2020078914 W CN 2020078914W WO 2020192432 A1 WO2020192432 A1 WO 2020192432A1
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solid
optionally
acid catalyst
solid acid
raw material
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Chinese (zh)
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张睿哲
刘运思
闵渝
陈文健
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Guangzhou Yinnovator Biotech Co Ltd
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Guangzhou Yinnovator Biotech Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/14—Hemicellulose; Derivatives thereof
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21B—FIBROUS RAW MATERIALS OR THEIR MECHANICAL TREATMENT
    • D21B1/00—Fibrous raw materials or their mechanical treatment
    • D21B1/04—Fibrous raw materials or their mechanical treatment by dividing raw materials into small particles, e.g. fibres
    • D21B1/12—Fibrous raw materials or their mechanical treatment by dividing raw materials into small particles, e.g. fibres by wet methods, by the use of steam
    • D21B1/30—Defibrating by other means
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C3/00—Pulping cellulose-containing materials
    • D21C3/20—Pulping cellulose-containing materials with organic solvents or in solvent environment
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C5/00—Other processes for obtaining cellulose, e.g. cooking cotton linters ; Processes characterised by the choice of cellulose-containing starting materials

Definitions

  • This application relates to the field of decomposition and recovery of biological raw materials, for example, to a method for catalytically decomposing wood fiber raw materials.
  • Lignocellulosic raw materials mainly contain cellulose, hemicellulose, and lignin. In the separation of traditional lignocellulosic raw materials, the product is single, and the product is usually cellulose. Other components of lignocellulosic raw materials are often regarded as by-products, and due to Difficulty in recycling leads to low economic benefits.
  • the separation liquid In traditional industrial separation of lignocellulosic raw materials, most of the inorganic acids, such as hydrochloric acid and sulfuric acid, are used as catalysts, so the separation liquid often contains strong liquid acids. Since the separation liquid contains strong liquid acid, it is easy to corrode the cooking equipment, which improves the anti-corrosion requirements of the cooking equipment, and further increases the separation cost of the wood fiber raw materials.
  • the solid acid catalyst is a new type of catalyst that is easy to handle and store, non-corrosive to equipment, stable in nature, renewable and reusable, and environmentally friendly.
  • CN103657653A discloses a method for catalyzing the hydrolysis of cellulose by a solid acid catalyst.
  • a solid acid is used to replace traditional inorganic liquid strong acids to catalyze the hydrolysis of cellulose.
  • CN102504028A discloses a method for preparing cellulose organic acid esters by solid acid catalysts, using three solid acids of SO 4 2- /M x O y type solid acid, biomass carbon-based solid acid, and phospho-aluminum molecular sieve solid acid as catalysts and organic acids It is a solvent and an organic acid anhydride is an esterification agent to prepare cellulose organic acid ester.
  • CN104017916A discloses a method for using biomass residue-based magnetic nano solid acid catalyst to catalyze cellulose hydrolysis. Cellulose, distilled water and biomass residue-based magnetic nano solid acid catalyst are mixed and heated to separate and obtain a cellulose hydrolysate. The above methods mainly use solid acid catalysts to decompose cellulose, although good results have been achieved, but their applicability is not wide.
  • the traditional method uses water to cook the lignocellulosic raw material, and the product obtained is generally cellulose, which has the disadvantages of single product structure, difficult by-product processing, and large environmental pollution.
  • the product obtained is generally cellulose, which has the disadvantages of single product structure, difficult by-product processing, and large environmental pollution.
  • the purpose of this application is to provide a method for catalytically decomposing lignocellulosic raw materials to obtain three products of sugar solution, lignin and cellulose, and at the same time to achieve efficient extraction of valuable components in lignocellulosic raw materials and recovery of valuable components
  • the rate can reach above 92wt%.
  • This application provides a method for catalytically decomposing lignocellulosic raw materials, the method comprising the following steps:
  • step (2) Sieving the solid phase mixture obtained in step (1) to obtain cellulose and solid acid catalyst; concentrating the cooking liquor obtained in step (1) to recover the organic solvent to obtain a mixture of sugar and lignin .
  • the organic solvent in step (1) is at least one of organic acids, organic alcohols, or esters.
  • the organic solvents may be ethanol, propanol, butanol, formic acid, acetic acid, and propylene. At least one of acid, ethyl acetate, or butyl acetate, but not limited thereto.
  • the mass ratio of the organic solvent and the wood fiber raw material in step (1) is (3-30):1, for example, it can be 3:1, 5:1, 10:1, 15:1, 20:1 , 25:1 or 30:1, etc.
  • the lignocellulosic raw material in step (1) is woody biomass and/or grassy biomass, and optionally woody biomass.
  • the woody biomass may be at least one of hardwood, softwood, or shrubs
  • the grassy biomass may be at least one of bagasse, bamboo, rice straw, wheat straw, corn stalk, or reed.
  • Species, but not limited to this, other woody biomass and/or grassy biomass plant raw materials are also applicable to this application.
  • the pretreatment temperature in step (1) is 25-200°C, for example, it can be 25°C, 50°C, 75°C, 100°C, 125°C, 150°C, 175°C, or 200°C.
  • the pretreatment time of step (1) is 0.5-5h, for example, it can be 0.5h, 1h, 1.5h, 2h, 2.5h, 3h, 3.5h, 4h, 4.5h or 5h.
  • the solid acid catalyst in step (1) is at least one of a solid-supported catalyst, a zeolite molecular sieve, an oxide, a sulfide, a super acid, or an ion exchange resin.
  • the solid-supported catalyst may be at least one of SO 4 2- /M X O Y type, BF 3 /M X O Y type or H 3 PO 4 /M X O Y type.
  • M x O y is at least one of Fe 2 O 3 , Fe 3 O 4 , Al 2 O 3 , TiO 2 or SiO 2 ; but it is not limited to this, and other suitable solid-supported catalysts are also suitable for this application.
  • the zeolite molecular sieve may be at least one of ZSM-5 zeolite molecular sieve, X-type zeolite molecular sieve, or Y-type zeolite molecular sieve;
  • the oxide may be Al 2 O 3 , SiO 2 , B 2 O 3 , Nb At least one of 2 O 3 , Al 2 O 3 /B 2 O 3 or Al 2 O 3 /SiO 2 ;
  • the sulfide may be CdS and/or ZnS;
  • the super acid may be B 2 O 3 / At least one of ZrO 2 , WO 3 /ZrO 2 , MoO 3 /ZrO 2 or B 2 O 3 /ZrO 2 ;
  • the ion exchange resin can be Amberlyst-15, Nafion-NR50 or TiCl4/A-15 At least one.
  • the foregoing is only a list of different types of solid acid catalysts, and is not limited to this.
  • the solid acid catalyst has a granular or spherical shape.
  • the solid acid catalyst in step (1) is added in an amount of 0.1% to 5% by weight of the lignocellulosic raw material, for example, it can be 0.1% by weight, 0.5% by weight, 1% by weight, 1.5% by weight, 2% by weight, and 2.5% by weight. wt%, 3wt%, 3.5wt%, 4wt%, 4.5wt% or 5wt%, etc.
  • the cooking temperature in step (1) is 90-200°C, for example, it can be 90°C, 100°C, 125°C, 150°C, 175°C, 200°C, and the like.
  • the cooking time of step (1) is 0.5-10h, for example, it can be 0.5h, 1h, 2h, 3h, 4h, 5h, 6h, 7h, 8h, 9h or 10h.
  • step (2) before the sieving, the solid phase mixture is washed.
  • the washing operation is: alternately washing the solid phase mixture with an organic solvent and water for 2-10 times, and then sieving Or, first treat the solid phase mixture with 100-200°C steam for 10min-2h to remove the solvent contained in the fiber, then wash 2-10 times with water, and then sieving.
  • step (2) the cooking liquor can be evaporated and concentrated.
  • the temperature of evaporation and concentration in step (2) is 70-150° C., and it is carried out under negative pressure, and the concentration is 3-15 times.
  • the organic solvent is recovered during the concentration process, and the obtained concentrate contains sugar and lignin.
  • the solid acid catalyst recovered in step (2) can be regenerated after being reused 2-100 times.
  • the operation of the regeneration is: mixing the solid-supported catalyst with the corresponding acid solution or salt solution, and treating at 25-150°C. 24h, control the mass ratio of catalyst to acid solution or salt solution to be lower than 1:20, clean after treatment, dry at 50-150°C, and then treat at 300-700°C for 2-10h before reuse.
  • the above-mentioned acid solution or salt solution corresponds to the type of solid-supported catalyst.
  • the solution can be sulfuric acid or sulfate.
  • the corresponding acid solution can be phosphoric acid
  • the BF 3 /M X O Y type solid acid catalyst is regenerated, the corresponding acid solution can be fluoroboric acid.
  • the operation of the regeneration is: the recovered The solid acid catalyst is cleaned, dried at 50-150°C, and then treated at 300-700°C for 2-10h before reuse.
  • zeolite molecular sieve, oxide, sulfide, super acid or ion exchange resin zeolite molecular sieve, oxide, sulfide, super acid or ion exchange resin
  • This application can choose to further separate the mixture of sugar and lignin obtained in step (2).
  • the specific operation is: dissolving the mixture in water and separating the solid-liquid to obtain sugar liquid (liquid phase) and lignin (solid phase).
  • the method for catalytically decomposing lignocellulosic raw materials described in this application includes the following steps:
  • the organic solvent is organic acid, organic alcohol or ester At least one;
  • the lignocellulosic raw material is woody biomass and/or grassy biomass;
  • the solid acid catalyst is a solid-supported catalyst, zeolite molecular sieve, oxide, sulfide, super acid or ion exchange resin At least one of
  • step (2) Use an organic solvent and water to alternately wash the solid phase mixture obtained in step (1) for 2-10 times, or first steam the solid phase mixture at 100-200°C for 10min-2h to remove the solvent contained in the fiber, Then wash 2-10 times with water; screen the cleaned mixture, select a combination of screens with various apertures for screening, so that the solid acid catalyst is trapped on the screen with the aperture of 3-8mm to achieve cellulose and solid acid catalyst
  • step (1) Evaporate and concentrate the cooking liquor separated in step (1).
  • the concentration temperature is 70-150°C, under negative pressure, and the concentration is 3-15 times.
  • the organic solvent is recovered during the concentration process.
  • the concentrated liquid contains sugar and lignin; the concentrated liquid is dissolved in water, and the liquid and solid are separated to obtain sugar liquid and lignin.
  • the extraction rate of valuable substances (weight of sugar+weight of lignin+weight of cellulose)/weight of wood fiber raw material ⁇ 100%.
  • This application uses organic solvents as a solution for separating lignocellulosic raw materials, combined with solid acid catalysts for catalytic reactions, and the two play a synergistic effect. Through further control of process conditions, it can effectively destroy cellulose, lignin and hemicellulose The physical and chemical combination between the three products, sugar, lignin and cellulose, simultaneously improves the extraction rate of valuable substances, and the extraction rate is >92wt%.
  • This application uses solid acid catalysts instead of traditional strong inorganic acids (such as hydrochloric acid, sulfuric acid) as catalysts, which reduces the requirements for corrosion resistance of separation equipment, thereby reducing separation costs, and solid acid catalysts can be recycled after use, with good stability , Efficient and environmentally friendly.
  • traditional strong inorganic acids such as hydrochloric acid, sulfuric acid
  • This application uses organic solvent as the solution for separating lignocellulosic raw materials. After the separation, the organic solvent can be recovered by concentration, which reduces production costs and reduces environmental pollution, and is a green and environmentally friendly cooking method.
  • the lignocellulosic raw materials used in the specific embodiments of the present application can be selected from woody biomass such as hardwood, softwood or shrubs, as well as grassy biomass such as bagasse, bamboo, rice straw, wheat straw, corn stalk, or reed.
  • the weight of the extracted cellulose, lignin, and sugar is calculated from the weight of the product obtained after processing.
  • the lignin product can be directly weighed, and the sugar is calculated by analyzing the sugar content in the sugar solution obtained by analyzing the cellulose product.
  • the processed fiber raw material is measured to calculate its cellulose content.
  • step (2) Wash the solid phase mixture obtained in step (1) alternately with acetic acid and water for 6 times, sieving the cleaned mixture, and selecting a combination of screens with various apertures for sieving, so that the solid acid catalyst is trapped in The screen with an aperture of 3mm realizes the separation of cellulose and solid acid catalyst; the separated solid acid catalyst is washed with distilled water, dried and recycled at 100°C, and reused;
  • step (1) Evaporate and concentrate the cooking liquor separated in step (1).
  • the concentration temperature is 90°C, under negative pressure, and the concentration factor is 8 times.
  • the organic solvent is recovered during the concentration process, and the concentrated solution obtained after the end contains Sugar and lignin; dissolve the concentrated liquid in water, and obtain sugar liquid and lignin after solid-liquid separation.
  • the extraction rate of valuable substances was 92.8 wt%.
  • step (2) Treat the solid phase mixture obtained in step (1) with steam at 120°C for 20 minutes, and then wash it with water 8 times.
  • the cleaned mixture is sieved, and a combination of screens with multiple apertures is selected for sieving to make the solid
  • the acid catalyst is trapped on a screen with an aperture of 5mm to realize the separation of cellulose and solid acid catalyst; the separated solid acid catalyst is washed with distilled water, dried and recycled at 80°C, and reused;
  • step (1) Evaporate and concentrate the cooking liquor separated in step (1).
  • the concentration temperature is 100°C under negative pressure, and the concentration is 10 times.
  • Ethanol is recovered during the concentration process, and the concentrated solution obtained after the end contains sugar.
  • lignin dissolve the concentrated liquid in water, and obtain sugar liquid and lignin after solid-liquid separation.
  • the extraction rate of valuable substances was 93.6 wt%.
  • step (2) Wash the solid phase mixture obtained in step (1) alternately with ethyl acetate and water for 10 times, sieving the cleaned mixture, and select a combination of screens with various apertures for sieving to make the solid acid catalyst It is trapped on a screen with an aperture of 8mm to realize the separation of cellulose and solid acid catalyst; the separated solid acid catalyst is washed with distilled water, dried and recycled at 120°C, and reused;
  • step (1) Evaporate and concentrate the cooking liquor separated in step (1).
  • the concentration temperature is 120°C under negative pressure, and the concentration is 10 times.
  • the organic solvent is recovered during the concentration process, and the concentrated solution obtained after the end contains Sugar and lignin; dissolve the concentrated liquid in water, and obtain sugar liquid and lignin after solid-liquid separation.
  • the extraction rate of valuable substances is 93.1 wt%.
  • step (2) Treat the solid phase mixture obtained in step (1) with steam at 180°C for 15 minutes, and then wash it with water 5 times to sieve the cleaned mixture, and select a combination of screens with multiple apertures for sieving.
  • the solid acid catalyst is trapped on a screen with a diameter of 7mm to realize the separation of cellulose and solid acid catalyst; the separated solid acid catalyst is washed with distilled water, dried and recycled at 150°C, and reused;
  • step (1) Evaporate and concentrate the cooking liquor separated in step (1).
  • the concentration temperature is 120°C, under negative pressure, and the concentration factor is 6 times.
  • the organic solvent is recovered during the concentration process, and the concentrated solution obtained after the end contains Sugar and lignin; dissolve the concentrated liquid in water, and obtain sugar liquid and lignin after solid-liquid separation.
  • the extraction rate of valuable substances is 92.2 wt%.
  • step (2) Use acetic acid and water to alternately wash the solid phase mixture obtained in step (1) for 3 times.
  • the washed mixture is sieved, and a combination of screens with various apertures is selected for sieving, so that the solid acid catalyst is trapped in The screen with an aperture of 5mm realizes the separation of cellulose and solid acid catalyst; the separated solid acid catalyst is washed with distilled water, dried and recycled at 80°C, and reused;
  • step (1) Evaporate and concentrate the cooking liquor separated in step (1).
  • the concentration temperature is 150°C, and the concentration is 3 times.
  • the organic solvent is recovered during the concentration process, and the concentrated solution obtained after the end contains Sugar and lignin; dissolve the concentrated liquid in water, and obtain sugar liquid and lignin after solid-liquid separation.
  • the extraction rate of valuable substances was 92.7 wt%.
  • step (2) of Example 1 The solid acid catalyst separated in step (2) of Example 1 was mixed with sulfuric acid, treated at 70°C for 6 hours, and the mass ratio of solid acid catalyst to sulfuric acid was controlled to 1:20. After the treatment, it was rinsed with distilled water to neutrality. , Dried at 150°C, treated at 600°C for 4h, then returned to Example 1 for continued use.
  • Example 1 Compared with Example 1, except for replacing the organic solvent (acetic acid) in step (1) with water of equal mass, the other steps and conditions are exactly the same as those of Example 1.
  • the products obtained in this comparative example are sugar liquid and cellulose, and the extraction rate of valuable substances is 63 wt%.
  • Example 1 Compared with Example 1, except for replacing the organic solvent (acetic acid) in step (1) with a mixed solution of water and acetic acid (keeping the weight of the mixed solution of water and acetic acid equal to the weight of the acetic acid in Example 1), The other steps and conditions are exactly the same as in Example 1. Among them, the molar ratio of water and acetic acid in the mixed solution is 1:1, and the mass ratio of the lignocellulosic raw material to the mixed solution is still 20:1.
  • the products obtained in this comparative example are sugar liquid, lignin and cellulose, and the extraction rate of valuable substances is 75 wt%.
  • Example 1 Compared with Example 1, except that the SO 4 2- /Fe 2 O 3 solid acid catalyst in step (1) is replaced with the same content of sulfuric acid, the other steps and conditions are exactly the same as those of Example 1.
  • the products obtained in this comparative example are sugar liquid, lignin and cellulose, and the extraction rate of valuable substances is 83.6 wt%.
  • Examples 1-6 the method for catalytically decomposing lignocellulosic raw materials provided in the present application can obtain three products of sugar liquor, lignin and cellulose, and the extraction rate of valuable substances is >92wt%.
  • Comparative Example 1 when the traditional water cooking lignocellulosic raw material is used, on the one hand, only sugar liquid and cellulose can be obtained, and the product is single; on the other hand, the extraction rate of valuable substances is greatly reduced, which is only 63% by weight. 1 Reduced by about 30wt%.
  • Comparative Example 2 when the pretreatment is a mixture of water and organic solvent, the extraction rate of valuable substances is not high, only 75 wt%, which is nearly 20 wt% lower than that of Example 1.

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Abstract

L'invention concerne un procédé de décomposition catalytique d'une matière première lignocellulosique, comprenant : l'utilisation d'un solvant organique pour prétraiter la matière première lignocellulosique, l'ajout d'un catalyseur acide solide pour effectuer une ébullition après le prétraitement, et la réalisation d'une séparation solide-liquide après l'ébullition ; le lavage et le tamisage du mélange de phase solide séparé pour obtenir de la cellulose et un catalyseur acide solide ; et la concentration du liquide d'ébullition séparé, et la récupération du solvant organique, de façon à obtenir un mélange de saccharides et de lignine. La présente invention utilise un solvant organique en tant que solution pour séparer une matière première lignocellulosique, et utilise un catalyseur acide solide en combinaison pour effectuer une réaction catalytique. En régulant les conditions de traitement, trois produits, plus précisément un liquide de saccharide, de la lignine et de la cellulose sont obtenus, l'extraction efficace de composants de valeur dans la matière première lignocellulosique est réalisée, et le taux de récupération des composants de valeur peut être de 92 % en poids ou plus. En même temps, l'exigence de résistance à la corrosion d'un dispositif de séparation est réduite, et le catalyseur acide solide et le solvant organique peuvent être réutilisés, réduisant ainsi les coûts de production et la pollution environnementale, et ayant de bonnes perspectives d'application.
PCT/CN2020/078914 2019-03-27 2020-03-12 Procédé de décomposition catalytique d'une matière brute lignocellulosique Ceased WO2020192432A1 (fr)

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CN109942835A (zh) * 2019-03-27 2019-06-28 广州楹鼎生物科技有限公司 一种催化分解木质纤维原料的方法

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MA69153A1 (fr) * 2020-01-08 2025-07-31 Telios Pharma, Inc. Méthodes de traitement d'une splénomégalie

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