WO2011162249A1 - Procédé de fabrication d'un monosaccharide, d'un disaccharide, et/ou d'un oligosaccharide - Google Patents

Procédé de fabrication d'un monosaccharide, d'un disaccharide, et/ou d'un oligosaccharide Download PDF

Info

Publication number
WO2011162249A1
WO2011162249A1 PCT/JP2011/064151 JP2011064151W WO2011162249A1 WO 2011162249 A1 WO2011162249 A1 WO 2011162249A1 JP 2011064151 W JP2011064151 W JP 2011064151W WO 2011162249 A1 WO2011162249 A1 WO 2011162249A1
Authority
WO
WIPO (PCT)
Prior art keywords
disaccharides
heat treatment
minutes
polysaccharide
producing monosaccharides
Prior art date
Application number
PCT/JP2011/064151
Other languages
English (en)
Japanese (ja)
Inventor
泰司 山田
恵悟 花木
真人 西田
Original Assignee
花王株式会社
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 花王株式会社 filed Critical 花王株式会社
Publication of WO2011162249A1 publication Critical patent/WO2011162249A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/12—Disaccharides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P2201/00—Pretreatment of cellulosic or lignocellulosic material for subsequent enzymatic treatment or hydrolysis

Definitions

  • the present invention relates to a method for producing polysaccharides, particularly monosaccharides, disaccharides, and / or oligosaccharides (hereinafter collectively referred to as “decomposed sugars”) from biomass.
  • a method of pretreating biomass in advance prior to the saccharification step has been studied.
  • the pretreatment method for example, a sulfuric acid method, an organic solvent method, a hydrothermal treatment method, mechanical crushing, and the like are known. Also, a method for efficiently producing an ethanol raw material by combining these methods has been studied.
  • a coarse pulverization step for coarsely pulverizing a raw material containing lignocellulose a fine pulverization step for finely pulverizing a coarsely pulverized product
  • fine pulverization A method (Patent Document 1) including a hydrothermal treatment step of hydrothermally treating an object and a dehydration step of dehydrating the hydrothermal treatment product has been reported.
  • the present invention relates to the following 1) to 12). 1) Next steps (1) to (3): (1) A step of applying a compressive shear stress to a polysaccharide to pulverize the polysaccharide to obtain a pulverized polysaccharide; (2) a step of heat-treating the pulverized polysaccharide at 185 to 230 ° C. in the presence of water; (3) A step of obtaining a solid part by solid-liquid separation from the reaction product after the heat treatment, and allowing a hydrolase to act on the solid part, A process for producing monosaccharides, disaccharides and / or oligosaccharides.
  • Patent Document 1 describes that when the finely pulverized product obtained in the pulverization step is hydrothermally treated, about 0.98 MPa (about 180 ° C. or less as saturated steam) is preferable in order to suppress excessive decomposition of sugar. is there.
  • the Patent Document 1 does not disclose the implementation of hydrothermal treatment, and the present inventor performed the pulverization step of cellulose-based biomass and the hydrothermal treatment step according to the method described in Patent Literature 1, and then the actual enzymatic saccharification step.
  • the yield of cellulose after the hydrothermal treatment step is high, it has been found that the reaction is difficult to proceed in the enzymatic saccharification step, and the amount of decomposition sugar produced as a whole may be reduced.
  • the present invention relates to providing a method capable of improving the saccharification rate and efficiently producing a decomposed sugar from a polysaccharide.
  • the inventors of the present invention have intensively studied in view of the above problems.
  • the temperature can be reduced as in Patent Document 1.
  • the yield of cellulose after heat treatment is lower than when heat-treated, the subsequent enzymatic saccharification step unexpectedly improves the saccharification rate significantly and ultimately increases the yield of decomposed sugar. I found it.
  • the saccharification rate can be improved, and the decomposing sugar can be produced efficiently.
  • the method of the present invention can also be applied to cellulosic biomass, and can be expected as a technique for improving the production efficiency of useful substances such as ethanol from biomass.
  • Step (1) is a step of obtaining a pulverized polysaccharide by pulverizing the polysaccharide by applying compressive shear stress.
  • the polysaccharide used in the present invention include cellulose, hemicellulose, xyloglucan, pectin, starch, mannan, glucomannan, galactomannan, chitin, chitosan, inulin, alginic acid, agar, fucoidan, laminarin, ⁇ -glucan, pullulan. Natural polysaccharides such as these or derivatives thereof.
  • Examples of the derivative include esters in which at least a part of the hydroxyl group is esterified, ethers in which at least a part of the hydroxyl group is etherified, and the like. These can be used alone or in combination of two or more. Of these, cellulose, hemicellulose, chitin, and chitosan are preferable, and cellulose and hemicellulose are more preferable because they are inexpensive and can be converted into useful substances by fermentation production after decomposition.
  • the molecular weight of the polysaccharide used in the present invention is not particularly limited, but generally it is preferably 1,000 or more and 5,000,000 or less.
  • the raw material containing the said polysaccharide for example, biomass
  • Biomass is an organic resource derived from living organisms, excluding fossil resources.
  • the biomass include cellulose-based, starch-based, and saccharide-based biomass, and these can be used alone or in combination of two or more.
  • Cellulose biomass is mainly composed of cellulose, hemicellulose, and lignin.
  • cellulose hemicellulose
  • lignin For example, cotton, wood pulp, kenaf, hemp, small-diameter wood, thinned wood, sawdust, wood waste, waste paper, newspaper, wrapping paper, tissue paper Woody materials such as toilet paper and cardboard; plant biomass such as bagasse, switchgrass, elephant grass, rice straw and wheat straw.
  • starch-based biomass include rice, wheat, corn, and potato
  • examples of the saccharide-based biomass include sugar-based biomass such as sugar cane, sugar beet, seaweed, shrimp shell, and crab shell.
  • a compression shearing pulverizer In order to pulverize the polysaccharide by applying a compression shear stress, a compression shearing pulverizer can be used.
  • the compression shearing type pulverizer is a machine that can apply both compressive stress and shear stress, and examples thereof include a vibrating rod mill and a vibrating ball mill. Among these, a vibrating rod mill is preferable from the viewpoint of saccharification rate and production efficiency.
  • the rod is not particularly limited, but preferably has an outer diameter of 0.1 to 100 mm, more preferably 0.5 to 50 mm. Further, the filling rate of the rod (apparent volume of the agitating part of the vibration mill) varies depending on the model, but is preferably 10 to 97%, more preferably 15 to 95%.
  • the pulverization conditions such as the pulverization time and the rotational speed of the pulverizer may be set as appropriate in order to form a desired pulverized product.
  • the average particle size of the pulverized product is 0.002 to 0.3 mm, further 0.005 to 0.2 mm, further 0.01 to 0.05 mm, and further 0.01 to 0.04 mm. It is preferable from the viewpoint of efficiency.
  • an average particle diameter means the average value calculated
  • the polysaccharide may be coarsely pulverized in advance before being pulverized by applying compressive shear stress.
  • the method for coarse pulverization is not particularly limited, and for example, as a pulverizer, a cutter pulverizer such as a grinder or roll cutter, an impact pulverizer such as a hammer mill, a grinding pulverizer such as a colloid mill, or the like may be used. it can.
  • the coarse pulverization is preferably performed so that the average particle size of the polysaccharide is 1 to 15 cm, and more preferably 3 to 5 cm.
  • Step (2) is a step in which the pulverized product obtained in step (1) is heated at 185 to 230 ° C. in the presence of water. It does not restrict
  • the pulverized product is preferably used in the form of a slurry, and the content of polysaccharide in the slurry is 1 to 400 g / L, more preferably 5 to 300 g / L, and more preferably 8 to 200 g / L from the viewpoint of fluidity. Is preferred. Examples of the slurry include water and various buffer solutions.
  • the temperature of the heat treatment is in the range of 185 to 230 ° C., but 185 to 220 ° C., further 190 to 210 ° C., and further 185 to 200 ° C. is preferable from the viewpoint of saccharification rate and production efficiency.
  • the heating means include water vapor and electricity.
  • the heat treatment time in the range of 185 ° C. to 230 ° C. varies depending on the reaction method and the type of polysaccharide, but is preferably 10 minutes to 90 minutes, more preferably 15 minutes to 85 minutes, and further from the viewpoint of the decomposition rate and production efficiency. It is preferably 20 minutes to 80 minutes, more preferably 30 minutes to 65 minutes.
  • the heat treatment time means the total time in a state included in the specified temperature range, and the temperature may change as long as the temperature is included in the range. Therefore, the temperature raising and lowering times are included in the heat treatment time as long as they are included in the temperature range. If the temperature is intermittently included in the temperature range as a result of the temperature change, the total time included in the temperature range is set as the time.
  • the pressure during the heat treatment is preferably set to the saturated vapor pressure of water or higher, and further 1.1 to 10.0 MPa, further 1.2 to 8.0 MPa, and further 1.3 to 6.0 MPa. Further, 1.6 to 2.6 MPa is preferable.
  • a gas may be used, and examples of the gas used include inert gas, water vapor, nitrogen gas, and helium gas.
  • the pressure may be set by restricting the outlet channel with a valve or the like.
  • Step (3) is a step of obtaining a solid part by solid-liquid separation from the reaction product after the heat treatment, and allowing a hydrolase to act on the solid part.
  • the method for obtaining the solid part from the reaction product after the heat treatment by solid-liquid separation is not particularly limited, and can be performed by filtration, centrifugation, and sedimentation while cooling as necessary.
  • the cooling temperature is 100 ° C. or lower, preferably 80 ° C. or lower.
  • the hydrolase used in the present invention is not particularly limited as long as it has an activity of hydrolyzing polysaccharides.
  • amylase, glucoamylase, cellulase, dextranase, glucanase, glucosidase, galactosidase, Mannosidase, agarase, lactose, mutanase, chitinase, chitosanase and the like can be mentioned.
  • the origin of the hydrolase is not limited, and it may be an artificial enzyme by gene recombination technique, partial hydrolysis or the like.
  • the form of the hydrolase is not particularly limited, and dried enzyme protein, particles containing enzyme protein, liquid containing enzyme protein, and the like can be used.
  • the amount of hydrolase used varies depending on the conditions of the hydrolysis reaction, the type of polysaccharide, etc. For example, in the case of cellulase, 1 to 200 FPU per gram of the solid part is preferable, and 5 to 50 FPU is more preferable.
  • the FPU activity is measured by the IUPAC method shown below. First, 50 mg of filter paper (Whatman No. 1) is used as a substrate, 0.5 mL of enzyme solution and 1.0 mL of 0.05 M citrate buffer (pH 4.8) are added thereto, and the enzyme reaction is carried out at 50 ° C. for 1.0 hour. Then, 3.0 mL of dinitrosalicylic acid reagent is added, and the mixture is heated at 100 ° C.
  • the temperature and pH can be selected according to the characteristics of the enzyme to be used.
  • the pH should be 3 to 8, more preferably 4 to 7.
  • the temperature is preferably 10 to 80 ° C., more preferably 20 to 60 ° C.
  • the reaction time varies depending on the type of polysaccharide and the like, but is preferably 1 to 240 hours, more preferably 2 to 200 hours, and further preferably 3 to 140 hours from the viewpoint of saccharification rate and production efficiency.
  • examples of the monosaccharide obtained by the hydrolysis reaction include glucose, fructose, mannose, galactose, xylose, arabinose and the like.
  • examples of the disaccharide include cellobiose, maltose, di-N-acetylchitobiose, and the like.
  • Oligosaccharides include those having 3 to 10 monosaccharide units.
  • a decomposed sugar can be produced from a polysaccharide at a saccharification rate of 60 to 100%, further 70 to 100%, and further 80 to 100%.
  • the saccharification rate was obtained by dividing the total mass of water-soluble sugars (monosaccharides and disaccharides typified by glucose) produced by the hydrolysis reaction by the mass of polysaccharides contained in the raw material subjected to the hydrolysis reaction. Say the value.
  • the yield (yield) of the decomposition sugar through all the processes is 60% or more, Furthermore, 65% or more, Furthermore, 70% or more.
  • polysaccharides include many examples including cellulose, and cellulose includes ⁇ -cellulose having high crystallinity, modified ⁇ -cellulose and ⁇ -classified as hemicellulose. There is also cellulose.
  • the yield of polysaccharides, the saccharification rate, and the yield of decomposing sugars are based on ⁇ -cellulose, which is generally used as the cellulose purity in biomass. The method for measuring the amount of ⁇ -cellulose is described in the Examples.
  • the obtained decomposed sugar can be used to produce useful substances such as ethanol, polylactic acid, amino acids, xylitol, and erythritol by performing microbial fermentation or chemical conversion using these decomposed sugars as a sugar source.
  • ⁇ Measurement of ⁇ -cellulose amount> Distilled water (150 mL), sodium chlorite (1.0 g) and acetic acid (0.2 mL) are added to about 2.5 g of the degreased product obtained by Sosley extraction, and heated on a hot water bath at 80 ° C. Addition of sodium chlorite and acetic acid and heating for 1 hour after the addition were further performed twice. The contents were filtered, and the filtration residue was washed with water and acetone and then dried. 1 g of the obtained dried product was added to 25 mL of 17.5% aqueous sodium hydroxide solution and left for 30 minutes. After 30 minutes, 25 mL of water was added, stirred for 1 minute, and allowed to stand for 5 minutes. The contents were filtered, and the filter residue was washed with 10% aqueous acetic acid and boiling water and then dried. The weight of the obtained dry residue was defined as the amount of ⁇ -cellulose.
  • ⁇ -cellulose yield (%) ⁇ mass of ⁇ -cellulose contained in the solid part obtained by solid-liquid separation of the heat-treated reaction product obtained in step (2) ⁇ / ⁇ in step (2) Mass of ⁇ -cellulose contained in pulverized raw material polysaccharide ⁇ ⁇ 100 (i)
  • Saccharification rate (%) ⁇ (water-soluble sugar mass after reaction) ⁇ (water-soluble sugar mass before reaction) ⁇ / mass of ⁇ -cellulose ⁇ 100 (ii)
  • Example 1 100 g of dried rice straw was pre-ground with a grinder so that the volume-based average particle size was 3 to 5 cm.
  • a vibrating rod mill (MB-1 manufactured by Chuo Kako Co., Ltd., total volume 3.5L) was filled with 13 rods with an outer diameter of 30 mm (filling rate 74%), and 100 g of pre-ground rice straw was charged, 1,200c By shaking for 10 minutes at / min, ground rice straw was obtained.
  • the volume standard average particle size was 0.04 mm.
  • a slurry obtained by mixing 10 g of this ground rice straw ( ⁇ -cellulose content 32% by mass) and 90 g of water is placed in a batch hydrothermal apparatus (Start 200 New Quick, volume 180 mL, manufactured by Nitto Koatsu Co., Ltd.).
  • the temperature rising rate was 3.4 ° C./min, and after reaching 200 ° C., it was immediately cooled. The time at 185 ° C. to 230 ° C. was 30 minutes.
  • a solid part solid residue was obtained by filtration.
  • the residue was fractionated so that the dry mass was 5% by mass, and 0.1 M citrate buffer solution having a pH of 5.0 was added to make a total of 10 g. 62.5 ⁇ L of cellulase (Novozymes Cell Crust 1.5 L) was added thereto for saccharification (addition of residue per 1 g of dry weight was 8.75 FPU).
  • the saccharification reaction was carried out in a thermostatic bath at 50 ° C. for 48 hours while shaking at 110 r / min. After completion of the reaction, the liquid part was filtered with a 0.2 ⁇ m filter, and the water-soluble sugar concentration was measured. Cellobiose and glucose were measured as water-soluble sugars.
  • Example 2 A water-soluble sugar was obtained in the same manner as in Example 1 except that after reaching 200 ° C. in hydrothermal treatment, the mixture was cooled at 200 ° C. for 30 minutes and then cooled. The time spent at 185 ° C. to 230 ° C. was 65 minutes.
  • Example 3 A water-soluble sugar was obtained in the same manner as in Example 1 except that the batch hydrothermal apparatus was previously pressurized to 1 MPa with nitrogen gas.
  • Comparative Example 1 In the hydrothermal treatment, a water-soluble sugar was obtained in the same manner as in Example 1 except that it was immediately cooled after reaching 180 ° C.
  • Example 2 The ground rice straw obtained in Example 1 was enzymatically saccharified without hydrothermal treatment.
  • Comparative Example 3 A crushed rice straw was obtained by charging 40 g of dried rice straw into a grinder manufactured by Iwatani Corporation (Lab Miller 800DG, volume 260 mL) and stirring at 20,000 r / min for 10 minutes. The volume standard average particle diameter was 0.27 mm. 10 g of this ground rice straw ( ⁇ -cellulose content 32 mass%) and 90 g of water were mixed, and then heat treatment and enzymatic saccharification treatment were carried out in the same manner as in Example 2 to obtain a water-soluble sugar.
  • Comparative Example 4 A ground rice straw was obtained in the same manner as in Comparative Example 3 except that stirring was performed at 20,000 r / min for 120 minutes. The volume standard average particle diameter was 0.05 mm. 10 g of this ground rice straw ( ⁇ -cellulose content 32 mass%) and 90 g of water were mixed, and then heat treatment and enzymatic saccharification treatment were carried out in the same manner as in Example 2 to obtain a water-soluble sugar. Table 1 shows the conditions and results of each Example and Comparative Example.

Abstract

Le procédé de fabrication d'un monosaccharide, d'un disaccharide, et/ou d'un oligosaccharide ci-décrit comprend : une étape (1) consistant à réduire un polysaccharide en poudre fine par application d'une contrainte de cisaillement par compression, pour obtenir un polysaccharide réduit en poudre fine ; une étape (2) consistant à chauffer le polysaccharide réduit en poudre fine à 185-230°C en présence d'eau ; et une étape (3) consistant à récupérer la fraction solide du réactif chauffé par séparation solide-liquide et soumission à l'action d'une hydrolase.
PCT/JP2011/064151 2010-06-22 2011-06-21 Procédé de fabrication d'un monosaccharide, d'un disaccharide, et/ou d'un oligosaccharide WO2011162249A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010141534A JP2012005359A (ja) 2010-06-22 2010-06-22 単糖類、二糖類、及び／又はオリゴ糖の製造方法
JP2010-141534 2010-06-22

Publications (1)

Publication Number Publication Date
WO2011162249A1 true WO2011162249A1 (fr) 2011-12-29

Family

ID=45371432

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/064151 WO2011162249A1 (fr) 2010-06-22 2011-06-21 Procédé de fabrication d'un monosaccharide, d'un disaccharide, et/ou d'un oligosaccharide

Country Status (2)

Country Link
JP (1) JP2012005359A (fr)
WO (1) WO2011162249A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10327900A (ja) * 1997-06-02 1998-12-15 Agency Of Ind Science & Technol 水溶性オリゴ糖類及び単糖類の製造方法
JP2004089016A (ja) * 2002-08-29 2004-03-25 Tsukishima Kikai Co Ltd 廃建材の処理方法
JP2006136263A (ja) * 2004-11-12 2006-06-01 National Institute Of Advanced Industrial & Technology リグノセルロース系バイオマス処理方法
JP2008271962A (ja) * 2007-04-04 2008-11-13 National Institute Of Advanced Industrial & Technology 糖の製造方法
JP2009124973A (ja) * 2007-11-21 2009-06-11 National Institute Of Advanced Industrial & Technology リグノセルロース系バイオマスからエタノール原料およびエタノールを製造する方法
JP2009171951A (ja) * 2007-12-27 2009-08-06 Kao Corp 糖の製造方法
JP2009284867A (ja) * 2008-05-30 2009-12-10 Toshiba Corp セルロース糖化システム、エタノール製造システム及びその方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10327900A (ja) * 1997-06-02 1998-12-15 Agency Of Ind Science & Technol 水溶性オリゴ糖類及び単糖類の製造方法
JP2004089016A (ja) * 2002-08-29 2004-03-25 Tsukishima Kikai Co Ltd 廃建材の処理方法
JP2006136263A (ja) * 2004-11-12 2006-06-01 National Institute Of Advanced Industrial & Technology リグノセルロース系バイオマス処理方法
JP2008271962A (ja) * 2007-04-04 2008-11-13 National Institute Of Advanced Industrial & Technology 糖の製造方法
JP2009124973A (ja) * 2007-11-21 2009-06-11 National Institute Of Advanced Industrial & Technology リグノセルロース系バイオマスからエタノール原料およびエタノールを製造する方法
JP2009171951A (ja) * 2007-12-27 2009-08-06 Kao Corp 糖の製造方法
JP2009284867A (ja) * 2008-05-30 2009-12-10 Toshiba Corp セルロース糖化システム、エタノール製造システム及びその方法

Also Published As

Publication number Publication date
JP2012005359A (ja) 2012-01-12

Similar Documents

Publication Publication Date Title
JP5126728B2 (ja) リグノセルロース系バイオマス処理方法
EP2225387B1 (fr) Procédé de production de saccharide
JP2014506451A (ja) リグニン及び他の生物学的生成物を草本植物から酵素によって単離するプロセス及びシステム
JP4619917B2 (ja) リグノセルロースの前処理方法
Valladares-Diestra et al. Citric acid assisted hydrothermal pretreatment for the extraction of pectin and xylooligosaccharides production from cocoa pod husks
Sun et al. Integrated treatment of perennial ryegrass: Structural characterization of hemicelluloses and improvement of enzymatic hydrolysis of cellulose
WO2013143503A1 (fr) Procédé de préparation de sucre par hydrolyse enzymatique de résidu de patate douce
JP6063661B2 (ja) 粉砕物の製造方法
Meng et al. Fractional pretreatment of hybrid poplar for accelerated enzymatic hydrolysis: Characterization of cellulose-enriched fraction
JP2008271962A (ja) 糖の製造方法
US20150037848A1 (en) Method for producing saccharide
US9284614B2 (en) Pre-treatment method for plant biomass hydrolysis reaction raw materials and plant biomass saccharification method
JP5019421B2 (ja) 糖の製造方法
JP6182369B2 (ja) リグニン分解物の製造方法
JP5693286B2 (ja) 木質系バイオマスの糖化方法
JP5385563B2 (ja) 糖の製造方法
JP5385561B2 (ja) 糖の製造方法
EP3178939A1 (fr) Composition d'enzyme de saccharification, solution de réaction de saccharification, et procédé de production de sucre
JP5093472B2 (ja) オリゴ糖の製造方法
WO2011162249A1 (fr) Procédé de fabrication d'un monosaccharide, d'un disaccharide, et/ou d'un oligosaccharide
JP2013085523A (ja) キシロース、キシロビオース及び／又はキシロオリゴ糖の製造方法
WO2011059082A1 (fr) Procédé de production d'un monosaccharide, d'un disaccharide et/ou d'un oligosaccharide
JP2014117207A (ja) 糖の製造方法
WO2011021399A1 (fr) Procédé de préparation d’un monosaccharide, d’un disaccharide, et/ou d’un oligosaccharide
JP2011010617A (ja) セルロース含有製糖原料

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11798133

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11798133

Country of ref document: EP

Kind code of ref document: A1