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WO2017110975A1 - Procédé de production de composition de xylooligosaccharide - Google Patents

Procédé de production de composition de xylooligosaccharide Download PDF

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Publication number
WO2017110975A1
WO2017110975A1 PCT/JP2016/088294 JP2016088294W WO2017110975A1 WO 2017110975 A1 WO2017110975 A1 WO 2017110975A1 JP 2016088294 W JP2016088294 W JP 2016088294W WO 2017110975 A1 WO2017110975 A1 WO 2017110975A1
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WIPO (PCT)
Prior art keywords
membrane
separation membrane
molecular weight
xylooligosaccharide
sugar solution
Prior art date
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Ceased
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PCT/JP2016/088294
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English (en)
Japanese (ja)
Inventor
千晶 山田
裕佳 旭
茂行 舩田
栗原　宏征
淳 南野
山田　勝成
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Toray Industries Inc
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Toray Industries Inc
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Priority to JP2017505264A priority Critical patent/JP6900902B2/ja
Publication of WO2017110975A1 publication Critical patent/WO2017110975A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/04—Disaccharides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • 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
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K13/00—Sugars not otherwise provided for in this class

Definitions

  • the present invention relates to a method for producing a xylooligosaccharide composition by selectively concentrating xylooligosaccharides using a separation membrane.
  • Oligosaccharides are saccharides in which several monosaccharides are linked by glycosidic bonds, and various saccharides such as galactooligosaccharides, fructooligosaccharides, xylooligosaccharides, isomaltoligosaccharides, and dairy oligosaccharides are known. Yes. These oligosaccharides have specific sweetness, low calorie, caries resistance, and other specific health foods that have a selective growth-promoting effect on enterobacteria and keep the stomach in good condition. Many are commercially available.
  • xylo-oligosaccharides are less susceptible to degradation by digestive enzymes such as acid and amylase, and when ingested by humans, they reach the large intestine without being decomposed or absorbed. Compared to other oligosaccharides The effect is demonstrated with a small amount.
  • xylobiose composed of two molecules of xylose is known to have high utilization efficiency of lactic acid bacteria.
  • Xylooligosaccharides are used not only for human food use but also as an additive for livestock feed.
  • Xylo-oligosaccharide is manufactured from xylan, which is one of the main components of plants.
  • a method for producing xylooligosaccharide a method of hydrolyzing and extracting xylan contained in hemicellulose in a raw material by circulating high-temperature and high-pressure water through crushed hardwood (Patent Document 1), corn cob, cottonseed husk, bagasse and Known is a method (Patent Document 2) in which a plant raw material selected from the group consisting of rice straw is subjected to an alkali treatment or a pressure heat treatment, followed by an enzyme treatment.
  • xylo-oligosaccharides obtained by such production methods almost always contain impurities such as monosaccharides that do not have physiological functions and aromatic compounds derived from plant raw materials, so that the functionality of xylo-oligosaccharides is enhanced. Requires a purification process of xylo-oligosaccharides.
  • oligosaccharides methods using ion exchange resins and activated carbon, and methods using separation membranes are known.
  • a hydrolyzate of a xylan-containing plant material is subjected to nanofiltration using a nanofiltration membrane having a cutoff size (synonymous with a fractional molecular weight) of 150 to 500 g / mol.
  • a method for recovering oligosaccharide and hexose such as glucose from the non-permeation side is disclosed.
  • Patent Document 4 an aqueous sugar solution obtained by hydrolyzing cellulose-containing biomass is filtered through a separation membrane having a fractional molecular weight of 600 to 2,000 to remove a fermentation inhibitor from the permeate side, A method of concentrating a sugar solution mainly composed of monosaccharides (glucose and xylose) on the non-permeate side is disclosed.
  • xylooligosaccharides are produced and purified according to the above-described method, if the xylooligosaccharides before purification contain monosaccharides such as glucose and xylose, the xylooligosaccharides and monosaccharides cannot be separated.
  • monosaccharides such as glucose and xylose
  • sugar and glucose are mixed, there is a problem in that the effects of calories and sweetness caused by glucose cannot be excluded, and the usage is limited.
  • an object of the present invention is to provide a method for producing a high-purity xylo-oligosaccharide composition by separating monosaccharides and xylo-oligosaccharides.
  • a sugar solution containing at least xylobiose containing xylobiose and a monosaccharide containing glucose and xylose is filtered through a polyamide separation membrane having a molecular weight cut off of 300 to 1,000.
  • a polyamide separation membrane having a molecular weight cut off of 300 to 1,000.
  • the present invention has the following configurations (1) to (6).
  • a sugar solution containing at least a xylobiose containing xylobiose and a monosaccharide containing glucose and xylose is filtered through a polyamide separation membrane having a molecular weight cut off in the range of 300 to 1,000, and the xylooligosaccharide on the non-permeate side
  • a method for producing a xylooligosaccharide composition comprising a step of selectively concentrating sugars.
  • the step of filtering the sugar solution through a separation membrane having a molecular weight cut off of 2,000 to 100,000 as a pre-step of the filtration step using the polyamide separation membrane includes (1) to (5 ).
  • the manufacturing method of the xylooligosaccharide composition in any one of.
  • a monosaccharide and a xylo-oligosaccharide can be easily separated, and a high-quality xylo-oligosaccharide concentrate having a low monosaccharide content can be obtained.
  • Xylooligosaccharide is a general term for oligosaccharides in which several xyloses are linked. Specific examples include xylobiose, xylotriose, xylotetraose, xylopentaose, xylohexaose, and arabinose and uron in the side chain. The thing which the acid couple
  • a xylo-oligosaccharide containing at least xylobiose and a sugar solution containing glucose and xylose (hereinafter also simply referred to as a sugar solution) used in the present invention can be obtained, for example, by hydrolyzing biomass containing xylan and cellulose.
  • Sugar solutions prepared by mixing commercially available reagents, sugar solutions prepared by adding reagents to sugar solutions obtained by hydrolyzing biomass, and the like can be used.
  • Xylan is a constituent component of hemicellulose present in the cell wall of plant cells, and is a heterosaccharide having various side chains bonded to a ⁇ -1,4-bonded xylose main chain.
  • plant cells contain polysaccharides such as cellulose, which is a ⁇ -1,4-linked glucose polymer, and lignin, which is an aromatic polymer. It is entangled in a complicated way.
  • the sugar liquid obtained by hydrolyzing biomass containing xylan and cellulose contains glucose produced by hydrolysis of cellulose, xylooligosaccharide and xylose produced by hydrolysis of xylan.
  • an aromatic compound derived from lignin, acetic acid released from the xylan side chain, and the like may be contained in the sugar solution.
  • the biomass containing xylan and cellulose is not particularly limited as long as it is a plant-derived resource containing xylan and cellulose.
  • plants such as seed plants, fern plants, moss plants, algae, aquatic plants, etc., use of waste building materials, etc. Can do.
  • Seed plants are classified into gymnosperms and angiosperms, and both can be preferably used.
  • Angiosperms are further classified into monocotyledonous plants and dicotyledonous plants.
  • Specific examples of monocotyledonous plants include bagasse, switchgrass, napiergrass, eliansus, corn stover, corn cob, rice straw, and straw.
  • dicotyledonous plants beet pulp, eucalyptus, oak, birch and the like are preferably used.
  • Particularly preferred in the present invention is bagasse.
  • the method of hydrolyzing biomass containing xylan and cellulose is not particularly limited, but acid treatment with sulfuric acid, acetic acid, etc., alkali treatment with caustic soda, ammonia, etc., hydrothermal treatment, subcritical water treatment, steaming treatment, enzyme treatment, etc. Can be mentioned. These treatment methods may be carried out singly or a plurality of treatment methods may be combined. However, in order to increase the content of xylo-oligosaccharide in the sugar solution, it is preferable to carry out enzyme treatment, particularly xylanase treatment. More preferably, the biomass is hydrolyzed by one or more other methods before the xylanase treatment.
  • the xylanase is not particularly limited as long as it has an activity to hydrolyze xylan to produce xylo-oligosaccharides.
  • “Sumiteam” (registered trademark) X manufactured by Shin Nippon Chemical Industry Co., Ltd.
  • “Suclase” registered trademark)
  • X manufactured by Mitsubishi Chemical Foods Co., Ltd.
  • "Cellulosin” registered trademark
  • TP25 manufactured by HIBI Co., Ltd.
  • VERON 191 manufactured by AB Enzymes
  • Trichoderma Aspergillus genus (Aspergillus)
  • Thermomyces Aureobasidium, Streptomyces, Clostridium, Bacillus, Motoga genus (Thermotoga), Acremonium (Acremonium), Mucor (Mucor)
  • it can be used xylanase produced
  • filtration is performed using a polyamide separation membrane having a fractional molecular weight in the range of 300 to 1,000, preferably a polyamide separation membrane having a fractional molecular weight in the range of 300 to 500, so that it is contained in the sugar solution. It is characterized in that impurities other than the above xylooligosaccharide, particularly glucose and xylose are removed to the permeate side, and the xylooligosaccharide concentrate is recovered from the non-permeate side.
  • Fractionated molecular weight refers to the Membrane Society of Japan, Membrane Experiment Series, Volume III, Artificial Membrane Editor / ist Kimura, Shinichi Nakao, Haruhiko Ohya, Tsutomu Nakagawa (1993, Kyoritsu Shuppan)
  • a plot of data with the rejection rate on the axis and the data plotted on the axis is called a fractionated molecular weight curve.
  • the molecular weight at which the blocking rate is 90% is called the fractional molecular weight of the membrane. ”Is well known to those skilled in the art as an index representing the membrane performance of the separation membrane.
  • the filtration method using a separation membrane in the present invention is not particularly limited, but cross flow filtration in which a flow in the horizontal direction with respect to the membrane surface is preferable.
  • the separation membrane made of polyamide with a molecular weight cut off in the range of 300 to 1,000 has a very small pore size, so if there is no flow in the horizontal direction with respect to the membrane surface, deposits will adhere to the membrane surface. This is because the film is clogged.
  • the horizontal flow that is, the value of the film surface linear velocity is preferably 5 cm / second or more and 50 cm / second or less, more preferably 10 cm / second or more and 30 cm / second or less.
  • the molecular weights of xylobiose, glucose, and xylose contained in the sugar solution used in the present invention are xylobiose: 282.24, glucose: 180.16, and xylose: 150.13, respectively.
  • xylobiose 282.24, glucose: 180.16, and xylose: 150.13, respectively.
  • the molecular weight of any sugar is less than the molecular weight cut-off of the separation membrane.
  • Xylose and glucose selectively permeate on the permeate side, and xylooligosaccharide is selectively concentrated on the non-permeate side, so that xylooligosaccharide and monosaccharide can be separated.
  • the amount of xylooligosaccharide permeated on the permeate side is larger than the amount permeated on the non-permeate side, whereas the monosaccharide containing xylose and glucose is larger than the amount blocked on the non-permeate side.
  • the amount of light transmitted to the transmission side is also large.
  • Such a difference in the transmittance of the substance by the separation membrane can be evaluated by calculating the value of the blocking rate of the target substance.
  • the blocking rate of each sugar is calculated by the formula (1). If the treatment area of the separation membrane is large and there is a difference in concentration before and after passing through the separation membrane on the non-permeate side in crossflow filtration, the ⁇ concentration of the target sugar on the non-permeate side '' is the separation membrane The average value of the concentration before and after passing through. Moreover, since the rejection is a comparison of the filtration concentration, it is different from the weight-based material balance supplied to the separation membrane.
  • Target sugar rejection (%) concentration of target sugar on membrane permeation side / concentration of target sugar on membrane non-permeation side ⁇ 100 (Equation 1).
  • a sugar solution containing at least a xylobiose containing xylobiose and a monosaccharide containing glucose and xylose is filtered through a polyamide separation membrane having a molecular weight cut off in the range of 300 to 1,000
  • the blocking rate of xylooligosaccharides such as triose is higher than the blocking rate of monosaccharides such as xylose and glucose.
  • the preferable blocking rate of the xylobiose of the present invention is 40% or more and 100% or less, and more preferably 60% or more and 100% or less. Furthermore, the glucose rejection is preferably 8.5% or more lower than the xylobiose rejection, and more preferably 10% or lower.
  • the polyamide separation membrane used in the present invention comprises a support layer for maintaining the strength of the membrane and a functional layer (also referred to as a skin layer or a dense layer) for removing impurities. Whether it is an asymmetric membrane using the same material for the support layer and the functional layer, or a composite membrane using different membrane materials for the support layer and the functional layer, if the functional layer is made of polyamide, it is made of the polyamide of the present invention. It can be used as a separation membrane.
  • Examples of preferable carboxylic acid components of monomers constituting the polyamide of the polyamide separation membrane used in the present invention include trimesic acid, benzophenone tetracarboxylic acid, trimellitic acid, pyrometic acid, isophthalic acid, terephthalic acid, and naphthalenedicarboxylic acid.
  • aromatic carboxylic acids such as diphenylcarboxylic acid and pyridinecarboxylic acid.
  • Preferred amine components of the monomers constituting the polyamide include m-phenylenediamine, benzidine, methylenebisaniline, 4,4′-diaminobiphenyl ether, dianisidine, 3,3 ′, 4-triaminobiphenyl ether, 3, 3 ′, 4,4′-tetraaminobiphenyl ether, 3,3′-dioxybenzidine, 1,8-naphthalenediamine, m (p) -monomethylphenylenediamine, 3,3′-monomethylamino-4,4 ′ Diaminobiphenyl ether, 4, N, N ′-(4-aminobenzoyl) -p (m) -phenylenediamine-2,2′-bis (4-aminophenylbenzimidazole), 2,2′-bis (4 -Aminophenylbenzoxazole), 2,2'-bis (4-aminophenylbenzothiazole), etc.
  • polyamide separation membrane used in the present invention examples include NF270 manufactured by Filmtech, NFW, NFG manufactured by Synder, and DESAL G series GE (G-5) type manufactured by GE W & PT.
  • the xylooligosaccharide concentrate obtained in the present invention is diluted with water, filtered again through a polyamide separation membrane having a molecular weight cut off of 300 to 1,000, and recovered from the non-permeating side, thereby including xylobiose.
  • the purity of xylo-oligosaccharide can be further increased.
  • the separation membrane used for the first time and the second time may be the same, or different separation molecular weights may be used.
  • a polyamide separation membrane having a molecular weight cut off of 300 to 1,000 to a temperature of 50 ° C. or lower.
  • the temperature exceeds 50 ° C., decomposition of xylo-oligosaccharide proceeds by the action of xylanase remaining in the sugar solution, and the concentration of xylose may increase.
  • filtration may be conducted through a separation membrane having a fractional molecular weight of 2,000 to 100,000.
  • the separation membrane with a molecular weight cut off of 2,000 to 100,000 used in the previous step is larger than the molecular weight cut off of the polyamide separation membrane to be used later, and also permeates xylobiose and other xylooligosaccharides to give xylanase and coloring
  • the molecular weight is not particularly limited as long as it does not permeate a polymer component such as a component, but the molecular weight cut off is more preferably in the range of 5,000 to 50,000, and still more preferably in the range of 10,000 to 30,000.
  • Separation membranes with a molecular weight cut off of 2,000 to 100,000 include polyethersulfone (PES), polysulfone (PS), polyacrylonitrile (PAN), polyvinylidene fluoride (PVDF), regenerated cellulose, cellulose, cellulose ester Sulfonated polysulfone, sulfonated polyethersulfone, polyolefin, polyvinyl alcohol, polymethyl methacrylate, polytetrafluoroethylene and the like can be used.
  • the enzyme agent may contain an enzyme group involved in cellulose degradation, and regenerated cellulose, cellulose, and cellulose ester undergo degradation, so PES, PVDF, etc. It is preferable to use a separation membrane made of the above synthetic polymer.
  • the separation membrane having a molecular weight cutoff of 2,000 to 100,000 used in the present invention include GE W & PT's DESAL brand M series, P series, G series GH (G-10) type, GK (G -20) Type, GM (G-50) type, "DURATHERM” (registered trademark) series HWS UF type, STD UF type, Synder VT, MT, ST, SM, MK, MW, LY, BN , BY, “Microza” (registered trademark) UF series manufactured by Asahi Kasei Corporation, NTR-7410, NTR-7450 manufactured by Nitto Denko Corporation, and the like.
  • the sugar solution may be filtered through a microfiltration membrane to remove fine particles.
  • a separation membrane having an average pore size of about 0.01 to 10 ⁇ m is preferably used.
  • the xylo-oligosaccharide concentrate recovered as a non-permeate by filtration through the polyamide separation membrane removes impurities such as coloring components using activated carbon or ion exchange resin as necessary, and further, vacuum concentration or evaporation concentration, Or you may perform processes, such as pulverization.
  • RO water and dilute hydrochloric acid were added to 1 kg of bagasse hydrolyzate per dry weight to adjust the pH to 5.0 to prepare a slurry of 5% by weight of bagasse hydrolyzate (dry weight).
  • 4 g of xylanase powder [“Cellulosin” (registered trademark) TP25, manufactured by HBI Co., Ltd.] was dissolved therein and reacted at 40 ° C. for 12 hours. After completion of the reaction, the xylanase inactivated by heating at 70 ° C. for 1 hour was subjected to solid-liquid separation, and the supernatant was recovered. The supernatant was filtered under the conditions of an operating temperature of 25 ° C.
  • Example 1 Membrane separation of sugar solution using polyamide separation membrane
  • separation membrane A DESAL G series GE (G-5) type "(membrane material: polyamide composite membrane, molecular weight cut off 1,000)
  • the saccharide solution 2L prepared by the method described in Reference Example 2 was filtered using a “SEPA” (registered trademark) CF-II (manufactured by GE W & PT, Effective membrane area 140 cm 2 ), operating temperature 25 ° C., membrane surface linear velocity 20 cm / sec, filtration under non-permeate side liquid volume 0.5 L under conditions of filtration pressure 0.5 MPa
  • Table 2 shows the results of collecting the non-permeate and analyzing various sugar concentrations.
  • Separation membrane B SPE1 (membrane material: polyethersulfone, molecular weight cut off 1,000, manufactured by Synder) as a separation membrane
  • separation membrane C ETNA01PP (membrane material: composite fluororesin, fractional molecular weight 1,000, manufactured by Alfaval) was used for filtration under the same conditions and operations as in Example 1.
  • Table 2 shows various sugar concentrations of the xylooligosaccharide concentrate recovered as a non-permeate.
  • Example 1 When comparing the results of Example 1 and Comparative Example 1, the average molecular weights of the separation membranes A, B, and C are all equal to 1,000, but the separation membrane that is the polyamide separation membrane of Example 1 Only when A was used, the result was that xylooligosaccharides were selectively concentrated on the non-permeation side, and glucose and xylose were selectively permeated to the permeation side. On the other hand, when the separation membranes B and C that are not the polyamide separation membranes of Comparative Example 1 were used, xylose, glucose, and xylobiose all permeated to the permeation side, so that xylooligosaccharides could be selectively concentrated. There wasn't.
  • Example 2 Membrane separation of sugar solution using polyamide separation membranes having various fractional molecular weights
  • Separation membrane D NFG (membrane material: polyamide composite membrane, fractional molecular weight 600-800, manufactured by Synder)
  • Separation membrane E NFW (membrane material: polyamide composite membrane, fractional molecular weight 300 to 500, manufactured by Synder) was used for filtration under the same conditions and operation as in Example 1.
  • Table 3 shows the results of collecting the non-permeate and analyzing various sugar concentrations.
  • Example 2 From the results of Example 1 and Example 2, when a polyamide separation membrane having a molecular weight cut off in the range of 300 to 1,000 is used, the xylooligosaccharide is selectively concentrated on the non-permeating side, and is a xylooligosaccharide and a monosaccharide. It was found that glucose and xylose can be separated.
  • Example 3 Improvement of Xylobiose content rate by hydrofiltration 1.5 L of RO water was added to 0.5 L of xylo-oligosaccharide concentrate 0.5 L obtained by filtration using separation membrane E in Example 2 to make the total amount 2 L, Filtration was performed again using the separation membrane E under the same conditions and operations as in Example 2. This operation was repeated twice, and the results of measuring the various sugar concentrations of the xylooligosaccharide concentrate at each time according to Reference Example 1 are shown in Table 4. By repeating the hydrofiltration, the concentration of xylose and glucose decreased, and the purity of the xylooligosaccharide was further improved.
  • Example 4 Inhibition rate in membrane separation of biomass-derived sugar liquid using polyamide separation membrane
  • the bagasse hydrolyzate prepared by the method of Reference Example 2 was washed with 10 times the amount of RO water. Solid-liquid separation.
  • the bagasse hydrolyzate after washing is reacted with xylanase in the same manner as in Reference Example 2, and solid-liquid separation, microfiltration, and ultrafiltration are performed in the same manner as in Reference Example 2 to obtain a biomass-derived sugar solution. Obtained.
  • the sugar concentration of this sugar solution was measured by the method of Reference Example 1. The results are shown in Table 5.
  • Separation membrane A DESAL G series GE (G-5) type "(membrane material: polyamide composite membrane, molecular weight cut off 1,000, manufactured by GE W & PT), separation membrane D: NFG (membrane material: polyamide composite) Biomass-derived sugar solution was filtered using each of a membrane, a molecular weight cutoff of 600 to 800, manufactured by Synder), and a separation membrane E: NFW (membrane material: polyamide composite membrane, molecular weight cutoff of 300 to 500, manufactured by Synder).
  • the membrane separator uses “SEPA” (registered trademark) CF-II (manufactured by GE W & PT, effective membrane area 140 cm 2 ), operating temperature is 25 ° C., membrane surface linear velocity is 20 cm / sec, and filtrate is used. Total circulation filtration was performed to return to the supply tank, and filtration was performed while adjusting the pressure so that each membrane had the same filtration rate.
  • the filtrate and the feed solution were sampled, and the sugar concentration was measured by the method of Reference Example 1. From the measured sugar concentration, the inhibition rate of each sugar was determined by equation (1).
  • Example 5 Blocking rate in membrane separation of model sugar solution using polyamide membrane Xylose 0.65 g / L, glucose 0.95 g / L, xylobiose 2.1 g / L dissolved in RO water, Example A model sugar solution (see Reference Example 3) containing approximately the same amount of sugar as the sugar solution prepared in 4 was prepared.
  • the model sugar solution was filtered using the same membrane and filtration conditions as in Example 4. Filtration was performed by adjusting the pressure so that the filtration rate was the same as in Example 4. The filtrate and the feed solution were sampled in the same manner as in the examples, and the inhibition rate of each sugar was determined.
  • the xylooligosaccharide composition obtained in the present invention can be added to processed foods, beverages, health foods, supplements, foods for specified health use, cosmetics, pet foods, livestock feeds, and the like.

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Abstract

L'invention concerne un procédé de production d'une composition de xylooligosaccharide, consistant à filtrer un sucre liquide contenant du xylose, du glucose, et un xylooligosaccharide contenant au moins du xylobiose à travers une membrane de séparation faite d'un polyamide ayant un poids moléculaire dans la plage de 300 à 1000, et ainsi concentrer sélectivement le xylooligosaccharide sur le côté de non-perméation.
PCT/JP2016/088294 2015-12-25 2016-12-22 Procédé de production de composition de xylooligosaccharide Ceased WO2017110975A1 (fr)

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
CN110551774A (zh) * 2019-09-24 2019-12-10 华侨大学 一种从海葡萄中酶法制备活性β-1,3-木寡糖的方法
CN112359080A (zh) * 2020-11-03 2021-02-12 江苏康维生物有限公司 一种木二糖和木三糖含量高的低聚木糖制备方法

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WO2010067785A1 (fr) * 2008-12-09 2010-06-17 東レ株式会社 Procédé pour la fabrication de liquide à base de sucre
WO2013018694A1 (fr) * 2011-07-29 2013-02-07 東レ株式会社 Procédé de préparation d'une solution de sucre
WO2013187385A1 (fr) * 2012-06-12 2013-12-19 東レ株式会社 Procédé de production d'une solution sucrée
WO2014065364A1 (fr) * 2012-10-25 2014-05-01 東レ株式会社 Procédé de fabrication d'acide organique ou de sel de celui-ci

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004517118A (ja) * 2000-12-28 2004-06-10 ダニスコ スイートナーズ オイ キシロースの回収
WO2010067785A1 (fr) * 2008-12-09 2010-06-17 東レ株式会社 Procédé pour la fabrication de liquide à base de sucre
WO2013018694A1 (fr) * 2011-07-29 2013-02-07 東レ株式会社 Procédé de préparation d'une solution de sucre
WO2013187385A1 (fr) * 2012-06-12 2013-12-19 東レ株式会社 Procédé de production d'une solution sucrée
WO2014065364A1 (fr) * 2012-10-25 2014-05-01 東レ株式会社 Procédé de fabrication d'acide organique ou de sel de celui-ci

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* Cited by examiner, † Cited by third party
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CN110551774A (zh) * 2019-09-24 2019-12-10 华侨大学 一种从海葡萄中酶法制备活性β-1,3-木寡糖的方法
CN112359080A (zh) * 2020-11-03 2021-02-12 江苏康维生物有限公司 一种木二糖和木三糖含量高的低聚木糖制备方法

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