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WO2024058256A1 - Procédé de production d'un monosaccharide ou d'un oligosaccharide à partir d'un polysaccharide, solution utilisée dans ledit procédé de production, et composition comprenant un monosaccharide ou un oligosaccharide - Google Patents

Procédé de production d'un monosaccharide ou d'un oligosaccharide à partir d'un polysaccharide, solution utilisée dans ledit procédé de production, et composition comprenant un monosaccharide ou un oligosaccharide Download PDF

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Publication number
WO2024058256A1
WO2024058256A1 PCT/JP2023/033628 JP2023033628W WO2024058256A1 WO 2024058256 A1 WO2024058256 A1 WO 2024058256A1 JP 2023033628 W JP2023033628 W JP 2023033628W WO 2024058256 A1 WO2024058256 A1 WO 2024058256A1
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mol
solution
concentration
polysaccharide
zinc chloride
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Japanese (ja)
Inventor
健文 千代
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Osaka Gas Chemicals Co Ltd
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Osaka Gas Chemicals Co Ltd
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Priority to JP2024547376A priority Critical patent/JPWO2024058256A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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 present invention relates to a method for producing a monosaccharide or oligosaccharide from a polysaccharide, a solution used in the production method, and a composition containing the monosaccharide or oligosaccharide.
  • biomass contains a group of substances called polysaccharides, such as chitin contained in the bodies of crustaceans as analogs of cellulose, and alginic acid contained in algae. , is essential to achieving carbon neutrality.
  • polysaccharides such as chitin contained in the bodies of crustaceans as analogs of cellulose, and alginic acid contained in algae.
  • cellulose derivatives such as regenerated cellulose and cellulose acetate are also thought to contribute to carbon neutrality if they can be efficiently recycled.
  • Cellulose consists of linear polymers in which glucose is linked by 1,4-glycosidic bonds, and has a strong crystal structure with multiple hydrogen bonds formed between the polymers, so it is insoluble in water and many solvents. It is also stable against many chemical reactions. Cellulose has a wide range of uses that take advantage of this property.
  • a technique for solubilizing insoluble cellulose as a polymer is also known, and a technique for processing or derivatizing cellulose after dissolution using this technique has been used for a long time.
  • a technique for processing or derivatizing cellulose after dissolution using this technique has been used for a long time.
  • Patent Document 1 it becomes alkali cellulose and dissolves in a strong alkaline aqueous solution such as sodium hydroxide.
  • cellulose derivatives such as cellulose acetate, methylcellulose, carboxymethylcellulose, and their salts have been synthesized by chemically modifying the hydroxyl groups.
  • Cellulose also dissolves in a mixed aqueous solution of alkali, ammonia, and copper salt, and this phenomenon is utilized to produce cuprammonium rayon.
  • Patent Document 2 ionic liquids as shown in Patent Document 2 have been developed in recent years as liquids that dissolve cellulose.
  • glucose which is a monomer
  • Glucose obtained from cellulose can be used, for example, as a raw material for bioethanol, as shown in Patent Document 3, and greatly contributes to the establishment of technology for effectively utilizing cellulose. Furthermore, glucose is an important substance as a raw material for synthetic chemicals such as surfactants, foods and food additives, and pharmaceuticals.
  • Patent Documents 4 and 5 Although it is possible to convert cellulose into glucose without dissolving it, as shown in Patent Documents 4 and 5, for example, it is not versatile because it requires an appropriate catalyst under high temperature and high pressure conditions.
  • glucose obtained by hydrolyzing cellulose is a useful substance, and dissolving cellulose is an important issue from the perspective of effective utilization of biomass.
  • glucose is usually produced by hydrolyzing edible starch, and is used as a raw material for bioethanol raw materials, synthetic chemicals such as surfactants, foods and food additives, pharmaceuticals, and other non-edible substances. If you try to use it as a food source, there is a problem that it will compete with food production.
  • the present invention aims to provide a method for dissolving polysaccharides such as cellulose under acidic and mild conditions, and a method for converting polysaccharides such as cellulose into monosaccharides or oligosaccharides under acidic and mild conditions. purpose.
  • the present inventor has conducted extensive research in view of the above problems. As a result, it was found that a solution containing predetermined amounts of hydrochloric acid and zinc chloride can dissolve polysaccharides including cellulose under mild conditions, and can also convert them into monosaccharides or oligosaccharides. It was also discovered that this solution can also dissolve poorly soluble polysaccharides other than cellulose and can similarly hydrolyze them to monosaccharides or oligosaccharides.
  • the present invention was completed through further research based on such knowledge.
  • the present invention includes the following configurations. Item 1.
  • the polysaccharide is cellulose, hemicellulose, cellulose acetate, chitin, chitosan, mucopolysaccharide, alginic acid, xanthan gum, gellan gum, pectin, carrageenan, gum arabic, succinoglycan, gardlan, locust bean gum, guar gum, tara gum, tamarind seed gum, 6.
  • the solution according to any one of items 1 to 5, which is at least one member selected from the group consisting of pullulan, soybean polysaccharide, gelatin, agar, carboxymethyl cellulose, and salts thereof. Section 7. Item 7.
  • Section 8 A method for producing a solution according to any one of items 1 to 7, comprising: (1) Hydrochloric acid with a concentration of 7 to 12 mol/L and the zinc chloride are combined so that the zinc chloride content is 2 to 10 mol/L, and the hydrogen chloride concentration in the hydrochloric acid and the zinc chloride content are A manufacturing method comprising the step of mixing so that the total amount of is 13 to 20 mol/L.
  • Item 9 The manufacturing method according to Item 8, comprising a step of mixing the mixture obtained in step (1) and a catalyst.
  • Item 11 A method for producing a monosaccharide or oligosaccharide, the method comprising: A manufacturing method comprising the step of mixing the solution according to any one of Items 1 to 7 and a polysaccharide.
  • a method for dissolving polysaccharide A method comprising the step of mixing the solution according to any one of Items 1 to 7 and a polysaccharide.
  • An apparatus for producing refined sugar products that carries out the method according to item 11 or 12, A solution supply means for supplying the solution; Polysaccharide supply means for supplying the polysaccharide; Mixing means for mixing the solution and the polysaccharide; Manufacturing equipment. Section 14. moreover, Item 14.
  • Item 17. The production apparatus according to any one of Items 13 to 16, wherein the refined sugar product is at least one selected from the group consisting of bioalcohol, bioalkane, synthetic chemicals, foods, food additives, and pharmaceuticals.
  • Section 18. A system for producing refined sugar products that carries out the method according to item 11 or 12, A solution supplying step of supplying the solution; a polysaccharide supplying step of supplying the polysaccharide; a mixing step of mixing the solution and the polysaccharide; A manufacturing system equipped with Item 19. moreover, Item 19.
  • the manufacturing system according to Item 18, comprising a catalyst supplying step of supplying a catalyst.
  • Section 20. moreover, a separation step of separating the monosaccharide or oligosaccharide obtained by the mixing step; a dissolving step of dissolving the monosaccharide or oligosaccharide separated in the separation step in water to obtain a sugar solution;
  • the manufacturing system according to item 18 or 19, comprising: Section 21. moreover, a conversion step of converting the sugar solution obtained in the dissolution step using yeast or a chemical reaction; a step of separating and purifying the product obtained by the conversion step; Item 21.
  • the production system according to any one of Items 18 to 21, wherein the refined sugar product is at least one selected from the group consisting of bioalcohols, bioalkanes, synthetic chemicals, foods, food additives, and pharmaceuticals.
  • Section 23. A waste reduction device that performs the method according to item 11 or 12, A solution supply means for supplying the solution; Polysaccharide supply means for supplying the polysaccharide; Mixing means for mixing the solution and the polysaccharide; A reduction device comprising: Section 24.
  • Separation means for separating monosaccharides or oligosaccharides obtained by the mixing means from insoluble waste;
  • a dissolving means for dissolving the monosaccharide or oligosaccharide separated by the separating means in water to obtain a sugar solution;
  • purification means for separating and purifying monosaccharides or oligosaccharides from the sugar solution obtained by the dissolution means;
  • Item 24 The reduction device according to Item 23.
  • Section 25 A waste reduction system that performs the method according to item 11 or 12, A solution supplying step of supplying the solution; a polysaccharide supplying step of supplying the polysaccharide; a mixing step of mixing the solution and the polysaccharide; A reduction system equipped with. Section 26.
  • a method for dissolving polysaccharides such as cellulose under acidic and mild conditions and a method for converting polysaccharides such as cellulose into monosaccharides or oligosaccharides under acidic and mild conditions. be able to.
  • this embodiment a mode for carrying out the present invention (hereinafter sometimes simply referred to as "this embodiment") will be described in detail. Note that the present embodiment below is an illustration for explaining the present invention, and the present invention is not limited only to this embodiment.
  • the solution of the present invention contains hydrochloric acid and zinc chloride, the hydrogen chloride concentration in the hydrochloric acid is 7 to 12 mol/L, the zinc chloride content is 2 to 10 mol/L, and the hydrochloric acid The total amount of the hydrogen chloride concentration and the zinc chloride content is 13 to 20 mol/L.
  • Such a solution of the present invention includes a saccharification solution, a polysaccharide solution, and the like.
  • saccharification liquid means a liquid capable of producing monosaccharides or oligosaccharides by hydrolyzing polysaccharides.
  • polysaccharide solution means a solution that can dissolve polysaccharides.
  • the present invention includes a “saccharified solution” or a “polysaccharide solution,” but in this specification, these "saccharified solutions” and “polysaccharide solutions” are collectively referred to simply as “dissolved solution.” ” is sometimes called.
  • monosaccharides or oligosaccharides can be obtained almost quantitatively from polysaccharides including cellulose under mild conditions.
  • cellulose is used as the polysaccharide, it is possible to convert materials based on cellulose, such as cotton, pulp, rayon, etc., into glucose under mild conditions.
  • the dissolving solution of the present invention can dissolve polysaccharides and obtain sugars under mild conditions even if it contains other organic substances, such as lignin in waste wood, and can dissolve polysaccharides and obtain sugars even if they contain other organic substances, such as lignin in waste wood.
  • sugars from various materials such as thinned wood, dead grass after mowing, and leaves under mild conditions, and at the same time, by removing cellulose, it is possible to reduce the amount of waste.
  • glucosamine can be obtained almost quantitatively from, for example, chitosan.
  • the obtained sugars can be used in ethanol, methane, synthetic chemicals, foods and food additives, pharmaceuticals, etc. through further processing.
  • the polysaccharide to be dissolved in the solution is not particularly limited, and either naturally derived products or synthetic products (biomass and artificial polysaccharides) can be employed.
  • the solution of the present invention can dissolve even polysaccharides with low solubility, and from the viewpoint of being able to produce monosaccharides or oligosaccharides, polysaccharides that are insoluble or poorly soluble in water are preferred. .
  • the water-insoluble or sparingly soluble polysaccharide is preferably a polysaccharide whose solubility in water is usually 0 to 15% by mass, particularly 0 to 5% by mass, and more preferably 0 to 1% by mass.
  • polysaccharides other than polysaccharides that are insoluble or poorly soluble in water can also be used, and other polysaccharides include, for example, alginic acid, xanthan gum, gellan gum, pectin, carrageenan, gum arabic, succinoglycan, gardlan, Examples include naturally derived products such as locust bean gum, guar gum, tara gum, tamarind seed gum, pullulan, soybean polysaccharide, gelatin, and agar, and synthetic products such as carboxymethyl cellulose. These polysaccharides may be salts such as sodium, potassium, magnesium, and calcium salts.
  • the form of the polysaccharide to be dissolved in the solution of the present invention is not particularly limited.
  • polysaccharides can be used alone or in combination of two or more.
  • Animal-derived Those derived from terrestrial animals (animal hair, body hair, dead insects, skin and nail scum, etc.) and their fragments, scraps, waste, etc.; Marine animals (3) Synthetic products: Cellulose and products containing it (cellulose-reinforced plastics, etc.) and its fragments, scraps, waste, etc.; Cellulose acetate and products containing it (cigarette filters, etc.), its fragments, offcuts, waste, etc.; derivatives such as carboxymethylcellulose, and products containing it, its fragments, offcuts, waste, etc.
  • It may contain substances containing the above-mentioned polysaccharides, as well as waste materials and substances other than polysaccharides.
  • solubility of substances other than polysaccharides in the dissolving solution is not a concern, as it is sufficient to reduce insoluble matter from the perspective of waste reduction.
  • Components insoluble in the solution can be separated as solids by known solid-liquid separation techniques such as filtration and centrifugation, and then subjected to appropriate treatment such as reuse or incineration.
  • the solution of the present invention differs depending on the intended use and required properties, but from the viewpoint of preventing the viscosity from increasing excessively during mixing and making it easier to stir, the above-mentioned polysaccharide is prepared, for example, at room temperature (25°C). , in a concentration of 0.01 to 50% by weight, preferably 0.1 to 30% by weight, after which it is possible to produce monosaccharides or oligosaccharides.
  • hydrochloric acid is used to easily suppress the above-mentioned polysaccharide from remaining suspended without dissolving it, to easily dissolve it sufficiently, to easily suppress smoke generation, and to improve operability.
  • hydrochloric acid having a hydrogen chloride concentration of 7 to 12 mol/L, preferably 8 to 12 mol/L is used. If the hydrogen chloride concentration of hydrochloric acid is less than 7 mol/L, polysaccharides (especially polysaccharides that are insoluble or poorly soluble in water) cannot be dissolved, and monosaccharides or oligosaccharides cannot be produced.
  • hydrochloric acid whose hydrogen chloride concentration exceeds 12 mol/L.
  • hydrochloric acid by using hydrochloric acid at a sufficiently high concentration, polysaccharides with low solubility can be dissolved and hydrolysis can proceed sufficiently.
  • the hydrogen chloride concentration of hydrochloric acid tends to be lowered by dissolving the polysaccharide after the solution of the present invention is mixed with the polysaccharide. Therefore, the hydrogen chloride concentration of hydrochloric acid in the solution of the present invention means the concentration before mixing with the polysaccharide.
  • the hydrogen chloride content of the hydrochloric acid is preferably 15 to 30% by mass, more preferably 15 to 25% by mass, based on 100% by mass of the solution of the present invention.
  • Zinc chloride contained in the solution of the present invention can be anhydrous, hydrated, or an aqueous solution.
  • the content of zinc chloride is set to 1 mole of hydrogen chloride in the above-mentioned hydrochloric acid, from the viewpoint of easily suppressing the above-mentioned polysaccharide from remaining suspended without dissolving it, and making it easy to dissolve it sufficiently.
  • it is preferably 0.1 to 3.0 mol, more preferably 0.5 to 2.0 mol.
  • the content of zinc chloride in the dissolving solution of the present invention is not particularly limited, but from the viewpoint that it is easy to prevent the above-mentioned polysaccharide from remaining suspended without being dissolved, and it is easy to sufficiently dissolve the polysaccharide. , 2 to 10 mol/L is preferable, and 3 to 8 mol/L is more preferable.
  • the content of zinc chloride in the dissolving solution of the present invention is not particularly limited, but from the viewpoint that it is easy to prevent the above-mentioned polysaccharide from remaining suspended without being dissolved, and it is easy to sufficiently dissolve the polysaccharide. is preferably 20.0 to 61.5% by weight, more preferably 30.0 to 45.0% by weight, based on 100% by weight of the solution of the present invention.
  • the amount of zinc chloride used be larger within the above range, but if the concentration of hydrochloric acid used is high. It is also possible to reduce the concentration of zinc chloride.
  • the hydrolysis reaction proceeds even if stirring is continued at the same temperature after dissolving the polysaccharide, but when the amount of polysaccharide input is increased, the amount of water in the system increases as the reaction progresses. There may be fewer water molecules and the dissolution rate may gradually decrease. In such cases, a small amount of catalyst may be added to the solution of the present invention in order to promote the reaction.
  • catalysts that can be used include, for example, ⁇ -hydroxycarboxylic acid and/or or ⁇ -hydroxysulfonic acid is preferred.
  • Such catalysts include ⁇ -hydroxycarboxylic acids such as glycolic acid and lactic acid; ⁇ -hydroxysulfonic acids such as hydroxymethanesulfonic acid and 1-hydroxyethanesulfonic acid.
  • These catalysts can be used alone or in combination of two or more.
  • the content of the catalyst is not particularly limited, but from the viewpoint of preventing the dissolution rate from decreasing as the reaction progresses, the above-mentioned 1 mol of zinc chloride is used. On the other hand, it is preferably 0.0001 to 1 mol, more preferably 0.0005 to 0.1 mol.
  • the solution of the present invention has a hydrogen chloride concentration in hydrochloric acid of 7 to 12 mol/L and a zinc chloride content of 2 to 10 mol/L.
  • the total amount that is, the total amount of hydrogen chloride concentration and zinc chloride content in hydrochloric acid, is 13 to 20 mol/L, preferably 14 to 19 mol/L, and more preferably 15 to 18 mol/L. If the total amount of hydrogen chloride concentration and zinc chloride content in hydrochloric acid is less than 13 mol/L, polysaccharides (especially polysaccharides that are insoluble or poorly soluble in water) cannot be dissolved, and monosaccharides or oligosaccharides cannot be produced. Can not do it. Furthermore, it is difficult to produce a solution in which the total amount of hydrogen chloride concentration and zinc chloride content in hydrochloric acid exceeds 20 mol/L.
  • the dissolving solution of the present invention can dissolve polysaccharides and produce monosaccharides or oligosaccharides under mild conditions, but it is difficult to reduce the yield of saccharides (monosaccharides or oligosaccharides), and it is possible to produce monosaccharides or oligosaccharides under mild conditions.
  • the temperature is preferably 20 to 100°C, more preferably 30 to 80°C.
  • compositions of the invention contain hydrochloric acid, zinc chloride, and monosaccharides or oligosaccharides. Furthermore, the composition of the present invention can also contain a catalyst, if necessary.
  • polysaccharides can be dissolved under mild conditions and monosaccharides or oligosaccharides can be produced from polysaccharides.
  • a polysaccharide is added to the solution of the present invention, and according to the method (or production method) of the present invention described below, a solution in which a monosaccharide or an oligosaccharide is added to the solution of the present invention,
  • a composition containing hydrochloric acid, zinc chloride, a monosaccharide or oligosaccharide, and optionally a catalyst can be produced. That is, the composition of the present invention is prepared by mixing the solution of the present invention and a polysaccharide (more specifically, mixing hydrochloric acid with a concentration of 7 to 12 mol/L, zinc chloride, and a polysaccharide as necessary). and a catalyst such that the zinc chloride content is 2 to 10 mol/L, and the total amount of the hydrogen chloride concentration in hydrochloric acid and the zinc chloride content is 13 to 20 mol/L).
  • monosaccharides or oligosaccharides can be easily separated, for example, by crystallization using an organic solvent.
  • the hydrogen chloride concentration of hydrochloric acid in the solution before mixing with the polysaccharide is 7 to 12 mol/L
  • water may be added after mixing with the polysaccharide to cause hydrolysis. Therefore, the hydrogen chloride concentration in the final composition of the present invention can be lowered. Therefore, the hydrogen chloride concentration in the final composition of the present invention is preferably 0.5 to 10 mol/L, more preferably 1 to 8 mol/L.
  • the monosaccharide or oligosaccharide contained in the composition of the present invention corresponds to the polysaccharide contained in the solution of the present invention described above.
  • Such monosaccharides include sugars such as glucose, mannose, galactose, arabinose, and xylose, uronic acids such as glucuronic acid and mannuronic acid, and amino sugars such as glucosamine.
  • uronic acids such as glucuronic acid and mannuronic acid
  • amino sugars such as glucosamine.
  • disaccharides such as maltose, cellobiose, sucrose, and lactose, as well as trisaccharides and tetrasaccharides in which the above-mentioned monosaccharides are glycosidic bonded, are mentioned.
  • the polysaccharide even if the polysaccharide is insoluble or poorly soluble in water, it is possible to convert the polysaccharide into monosaccharide or oligosaccharide almost quantitatively, so that it can be added to the composition of the present invention.
  • the content of monosaccharides or oligosaccharides contained can be equivalent to the content of polysaccharides in the above-mentioned solution of the present invention.
  • Part 1 of the present invention is a method for producing a solution of the present invention, comprising: (1) Hydrochloric acid having a concentration of 7 to 12 mol/L and the zinc chloride, the zinc chloride content being 2 to 10 mol/L, and the total amount of the hydrogen chloride concentration and zinc chloride content in the hydrochloric acid.
  • the method includes a step of mixing so that the amount is 13 to 20 mol/L.
  • the method of mixing hydrochloric acid and zinc chloride is not particularly limited.
  • zinc chloride can be added to hydrochloric acid.
  • the mixing ratio of hydrochloric acid and zinc chloride can be adjusted so that the content of each component falls within the above range.
  • step (2) It may also include a step of mixing the mixture obtained in step (1) and a catalyst.
  • the method of mixing the mixture obtained in step (1) and the catalyst is not particularly limited.
  • a catalyst can be added to the mixture obtained in step (1).
  • the content of the catalyst can be adjusted to fall within the above range.
  • the production method (part 2) of the present invention is a method for producing monosaccharides or oligosaccharides, comprising: The method includes a step of mixing the above-described solution of the present invention and a polysaccharide.
  • the manufacturing method of the present invention (part 3) is a method of manufacturing the composition of the present invention, comprising: The method includes a step of mixing the above-described solution of the present invention and a polysaccharide.
  • the method of the present invention is a method for dissolving polysaccharide, comprising: The method includes a step of mixing the above-described solution of the present invention and a polysaccharide.
  • step of mixing the above-described solution of the present invention and the polysaccharide is included as an essential step.
  • the method of mixing the solution of the present invention and the polysaccharide is not particularly limited.
  • the polysaccharide can be added to the solution of the present invention while stirring.
  • the mixing ratio of the solution of the present invention and the polysaccharide can be adjusted so that the content of each component falls within the above-described range.
  • the above-mentioned catalyst can also be mixed separately. In this case, it is preferable to adjust the total amount of the catalyst that can be contained in the solution of the present invention and the catalyst that is separately mixed so that the content is as described above.
  • the particles when mixing the solution of the present invention and polysaccharide, the particles may swell at the initial stage of the reaction (in the early stage of mixing), and the viscosity of the liquid may increase due to the eluted polymer components, reducing the stirring efficiency. . Even in this case, if stirring is continued, the viscosity will decrease as the reaction progresses and the stirring efficiency will gradually improve.
  • the solution of the present invention and the polysaccharide It is also possible to add the polysaccharide little by little to the solution of the present invention instead of mixing them all at once. In this case, it is preferable to add the polysaccharide to the solution of the present invention over a period of 1 to 120 minutes, particularly 5 to 60 minutes.
  • the reaction temperature during mixing can be arbitrarily selected in consideration of the desired conversion rate of polysaccharide and the yield of saccharides (monosaccharides or oligosaccharides). Normally, it is easy for the hydrolysis of polysaccharides to proceed sufficiently, the caramelization of the produced sugars (monosaccharides or oligosaccharides) is difficult to proceed, the liquid is difficult to brown, and the yield of sugars (monosaccharides or oligosaccharides) is difficult to proceed.
  • the reaction temperature is preferably 20 to 100°C, more preferably 30 to 80°C, from the viewpoints that it is easy to improve the viscosity, and the conversion rate of the polysaccharide is less likely to decrease because the viscosity is less likely to become excessively high and the reaction efficiency is less likely to decrease.
  • the reaction time can be arbitrarily selected in consideration of the desired conversion rate of polysaccharide and the yield of saccharide (monosaccharide or oligosaccharide). Normally, it is easy for the hydrolysis of polysaccharides to proceed sufficiently, the caramelization of the produced sugars (monosaccharides or oligosaccharides) is difficult to proceed, the liquid is difficult to brown, and the yield of sugars (monosaccharides or oligosaccharides) is difficult to proceed. From the viewpoint that it is easy to improve the conversion rate and that the conversion rate of polysaccharide is not easily decreased, the total reaction time is preferably 1 to 24 hours, and more preferably 2 to 12 hours. Note that when polysaccharide is dissolved using the dissolving solution of the present invention, a mixing time of 1 to 120 minutes, particularly 5 to 60 minutes is sufficient.
  • the hydrolysis reaction proceeds even if stirring is continued at the same temperature, so that monosaccharides or oligosaccharides cannot be obtained. is possible.
  • the reaction may be allowed to proceed for a certain period of time at the same temperature with stirring if necessary, but in order to accelerate the reaction, the reaction may be further increased. You can also proceed.
  • the temperature in this case is also preferably 20 to 100°C, more preferably 30 to 80°C, because it is difficult to reduce the yield of saccharides (monosaccharides or oligosaccharides) and it is easy to improve the conversion rate of polysaccharides. However, it is preferable to set the temperature higher than the reaction temperature before adding water.
  • the subsequent reaction time is such that hydrolysis of the polysaccharide is easily progressed, caramelization of the produced saccharides (monosaccharides or oligosaccharides) is difficult to proceed, and the liquid is
  • the reaction time is preferably 0.5 to 12 hours in total, and 1 to 6 Time is more preferred.
  • the polysaccharide even if the polysaccharide is insoluble or poorly soluble in water, it can be almost quantitatively hydrolyzed to monosaccharides or oligosaccharides (preferably monosaccharides). It is possible.
  • compositions of the invention can be obtained containing oligosaccharides and optionally catalysts.
  • composition of the present invention thus obtained can be used as it is, but the saccharide (monosaccharide or oligosaccharide) can be separated from hydrochloric acid, zinc chloride, and if necessary the catalyst using a known technique. You can also take it out. Furthermore, saccharides (monosaccharides or oligosaccharides) may be neutralized before being separated, or may be directly subjected to the separation step without being neutralized.
  • a base with an equimolar amount to the hydrochloric acid used and an amount corresponding to the valence of the zinc chloride used in the case of zinc chloride, 2
  • An aqueous base solution containing enough bases to provide hydroxide ions (2 times the mole) is added to precipitate zinc chloride as sparingly soluble zinc hydroxide, which is removed by filtration.
  • the remaining salts are removed using an ion exchange resin or ion exchange membrane to form an aqueous solution containing only saccharides (monosaccharides or oligosaccharides), and this is concentrated or crystallized using a poor solvent to form saccharides (monosaccharides or oligosaccharides) as solids. oligosaccharides) can be obtained.
  • Bases that can be used to neutralize saccharides (monosaccharides or oligosaccharides) before separation are not particularly limited, and include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; calcium hydroxide; Alkaline earth metal hydroxides such as barium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate Hydrogen carbonates; alkaline earth metal hydrogen carbonates such as calcium hydrogen carbonate and barium hydrogen carbonate; alkali metal acetates such as sodium acetate and potassium acetate; alkaline earth metal acetates such as calcium acetate and barium acetate; Bases commonly used in summation reactions can be used.
  • ammonia, organic amines, etc. can be used, but from the viewpoint of easily suppressing the formation of complexes with zinc ions in zinc chloride and easily precipitating as sparingly soluble zinc hydroxide, , the above-mentioned alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates, alkaline earth metal carbonates, alkali metal hydrogen carbonates, alkaline earth metal hydrogen carbonates, alkali metal acetates, alkaline earth It is preferable to use similar metal acetates and the like.
  • the aqueous solution is filtered, and then the salts remaining in the aqueous solution are removed using an ion exchange resin or ion exchange membrane to form an aqueous solution containing only sugars (monosaccharides or oligosaccharides), which can be concentrated or depleted.
  • saccharides can be obtained as solids.
  • the saccharide can be obtained as a solid by directly introducing an aqueous solution containing only saccharide (monosaccharide or oligosaccharide) into an organic solvent such as acetone.
  • saccharides (monosaccharides or oligosaccharides) can be separated by any known method, such as separation by chromatography or separation via derivatives.
  • Saccharides can be obtained as solids by preparing an aqueous solution containing only monosaccharides (oligosaccharides) and crystallizing this by concentrating or using a poor solvent.
  • the saccharide (monosaccharide or oligosaccharide) can be obtained as a solid by directly introducing an aqueous solution containing only saccharide (monosaccharide or oligosaccharide) into an organic solvent such as acetone.
  • saccharides can be separated by any known method, such as separation by chromatography or separation via derivatives.
  • the obtained saccharide (monosaccharide or oligosaccharide) can be used as it is, or may be subjected to a known purification process such as recrystallization in order to obtain the desired purity or structural isomer.
  • biofuel can also be produced using known methods.
  • the method for producing biofuel is not particularly limited, and any conventional method can be used.
  • the obtained saccharide (monosaccharide or oligosaccharide) can be fermented with a desired microorganism, for example, WO 2020/162502, JP 2011-254727, JP 2010-187656, Biofuel can be produced by the method described in International Publication No. 2008/105618 and the like.
  • the polysaccharide even if the polysaccharide is not hydrolyzed to monosaccharides, it can also be used as a technique for simply reducing the molecular weight of the polysaccharide to make it solubilized in water.
  • the dilution temperature and the amount of dilution water after the polysaccharide is dissolved can be adjusted within a range in which a product with a lower molecular weight does not precipitate.
  • recovery of sugars and removal of zinc chloride from the diluted aqueous solution can be performed according to the above-mentioned method.
  • a solution supply means for supplying the solution for supplying the solution; Polysaccharide supply means for supplying the polysaccharide; Mixing means for mixing the solution and the polysaccharide; can be provided.
  • the manufacturing device further includes: A catalyst supply means for supplying a catalyst may also be provided.
  • the manufacturing device further includes: Separation means for separating the monosaccharides or oligosaccharides obtained by the mixing means; A dissolving means for dissolving the monosaccharide or oligosaccharide separated by the separating means in water to obtain a sugar solution; It is also possible to have
  • the manufacturing device further includes: A conversion means for converting the sugar solution obtained by the dissolution means using yeast or a chemical reaction; means for separating and purifying the product obtained by the conversion means; It is also possible to have
  • the sugar refined product manufacturing system for carrying out the method of the present invention is not particularly limited, but may include: A solution supplying step of supplying the solution; a polysaccharide supplying step of supplying the polysaccharide; a mixing step of mixing the solution and the polysaccharide; can be provided.
  • the manufacturing system further includes: A catalyst supply step for supplying a catalyst may also be included.
  • the manufacturing system further includes: a separation step of separating the monosaccharides or oligosaccharides obtained by the mixing means; a dissolving step of dissolving the monosaccharide or oligosaccharide separated by the separation means in water to obtain a sugar solution; can also be provided.
  • the manufacturing system further includes: a conversion step of converting the sugar solution obtained by the dissolving means using yeast or a chemical reaction; a step of separating and purifying the product obtained by the conversion means; It is also possible to have
  • a solution supply means for supplying the solution Polysaccharide supply means for supplying the polysaccharide; Mixing means for mixing the solution and the polysaccharide; can be provided.
  • the reduction device further includes: Separation means for separating monosaccharides or oligosaccharides obtained by the mixing means from insoluble waste; A dissolving means for dissolving the monosaccharide or oligosaccharide separated by the separating means in water to obtain a sugar solution; purification means for separating and purifying monosaccharides or oligosaccharides from the sugar solution obtained by the dissolution means; It is also possible to have
  • a solution supplying step of supplying the solution; a polysaccharide supplying step of supplying the polysaccharide; a mixing step of mixing the solution and the polysaccharide; can be provided.
  • the reduction system further includes: a separation step of separating monosaccharides or oligosaccharides obtained by the mixing means from insoluble waste; a dissolving step of dissolving the monosaccharide or oligosaccharide separated by the separation means in water to obtain a sugar solution; purification means for separating and purifying monosaccharides or oligosaccharides from the sugar solution obtained by the dissolution means; It is also possible to have
  • Mixing means/mixing step A means or step capable of mixing the solution of the present invention, a polysaccharide, and, if necessary, a catalyst, that is, a means or step capable of performing the method of the present invention If so, it can be adopted without any particular restrictions.
  • Catalyst Supply Means/Catalyst Supply Step There is no particular restriction as long as it is a means or process that can supply a catalyst, and any known method can be employed.
  • Separation means/separation step Any method can be used without any particular limitation as long as it can separate saccharides (monosaccharides or polysaccharides) from the composition of the present invention. Specifically, means or steps that can perform the separation method described in the method of the present invention described above can be employed.
  • the solution of the present invention contains insoluble solids, for example, insoluble waste such as lignin in wood, saccharides (monosaccharides or polysaccharides) are separated from the composition of the present invention. It is preferable to perform a removal means or a removal step to remove the insoluble solid content beforehand, and known techniques such as filtration and centrifugation can be used.
  • Dissolution means/dissolution step Any method can be used without any particular restriction as long as the obtained saccharide (monosaccharide or polysaccharide) can be dissolved in water.
  • Conversion means/conversion step Any method can be used without particular limitation as long as the obtained saccharide (monosaccharide or polysaccharide) can be converted by yeast or chemical reaction.
  • yeast having ethanol fermentation ability or methane fermentation ability can be used to convert sugars into ethanol or methane.
  • the yeast to be used can be any yeast conventionally used for fermentation of sugars without any particular restrictions.
  • yeasts that have been genetically modified and given high functionality for various uses it is preferable to select and use yeasts that enhance the effects of this invention.
  • Ethanol and methane obtained by fermentation can be separated and purified using known techniques such as distillation and liquefaction.
  • the obtained saccharide (monosaccharide or polysaccharide) can be dissolved in an appropriate solvent and converted into the target substance by a chemical reaction with a reaction reagent.
  • the reaction container can be appropriately selected from known containers such as stainless steel and glass.
  • a known stirrer such as a stirring blade or a magnetic stirrer can be used.
  • Purification means/purification step Any method can be used without any particular limitation as long as it can separate and purify a product obtained by converting saccharides (monosaccharides or polysaccharides) by yeast or chemical reaction.
  • Identification was performed by mass spectrometry, and quantification was performed using a calibration curve prepared in advance using solutions in which commercially available glucose (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was dissolved in distilled water at concentrations of 10 ppm, 100 ppm, and 1000 ppm. .
  • the solids obtained were glucose with a purity of 98% or more.
  • the obtained oil was diluted to 1800 mL in a measuring cylinder and then further diluted 10 times (equivalent to 100 ppm if all the cellulose used was converted to glucose). ), the yield was calculated by quantifying using the above calibration curve.
  • Example 3 Identification and purity calculation of N-acetylglucosamine
  • LC-MS liquid chromatography mass spectrometer
  • Identification was performed by mass spectrometry, and quantification was performed using a calibration curve prepared in advance using solutions in which commercially available N-acetylglucosamine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was dissolved in distilled water at concentrations of 10 ppm, 100 ppm, and 1000 ppm. According to The obtained solid was N-acetylglucosamine with a purity of 98% or more.
  • Example 1 A solution was prepared by dissolving 15 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 25 g of 12N (12 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.), heated to 40°C, and carried out. A solution of Example 1 was obtained. The volume of the obtained solution was 25.0 mL, the hydrogen chloride concentration was 12 mol/L (21.9 mass %), the zinc chloride concentration was 4 mol/L (37.5 mass %), and the zinc chloride concentration was 4 mol/L (37.5 mass %). The concentration was 0.33 mol per mol of hydrogen chloride.
  • Example 2 A solution was prepared by dissolving 4 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 11 N (11 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd. prepared from 12 N hydrochloric acid) and heated to 40°C. The solution of Example 2 was obtained by heating. The volume of the obtained solution was 5.0 mL, the hydrogen chloride concentration was 11 mol/L (19.1 mass %), the zinc chloride concentration was 6 mol/L (44.4 mass %), and the zinc chloride concentration was 6 mol/L (44.4 mass %). The concentration was 0.55 mol per mol of hydrogen chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure. A viscous oil was obtained by distilling off. This oil was diluted to 1800 mL in a graduated cylinder, diluted 10 times, and analyzed using LC-MS, and it was confirmed that glucose was produced at a yield of 70%.
  • Example 3 A solution was prepared by dissolving 3.3 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 10 N (10 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd. prepared from 12 N hydrochloric acid) and heated at 40°C. The solution of Example 3 was obtained. The volume of the obtained solution was 5.0 mL, the hydrogen chloride concentration was 10 mol/L (19.0 mass %), the zinc chloride concentration was 5 mol/L (36.7 mass %), and the zinc chloride concentration was 5 mol/L (36.7 mass %). The concentration was 0.5 mol per mol of hydrogen chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure. A viscous oil was obtained by distilling off. This oil was diluted to 1800 mL in a graduated cylinder, diluted 10 times, and analyzed using LC-MS, and it was confirmed that glucose was produced at a yield of 33%.
  • Example 4 A solution was prepared by dissolving 4 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 10 N (10 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd.) prepared from 12 N hydrochloric acid, and heated to 40°C. did.
  • the volume of the obtained solution was 5.0 mL
  • the concentration of hydrogen chloride was 10 mol/L (17.5% by mass)
  • the concentration of zinc chloride was 6 mol/L (44.4% by mass)
  • the concentration of hydrogen chloride was 6 mol/L (44.4% by mass).
  • the concentration was 0.6 mol per mol of hydrogen chloride.
  • 0.023 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain the solution of Example 4.
  • Example 4 1.6 g of powdered cellulose (Fujifilm Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes with stirring to dissolve the powdered cellulose. The resulting viscous liquid was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 4.
  • the concentration of hydrogen chloride was 10 mol/L (14.9% by mass)
  • the concentration of zinc chloride was 6 mol/L (37.7% by mass)
  • the concentration of glycolic acid was 0.006 mol/L.
  • the concentration of zinc chloride was 0.6 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.001 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure.
  • a cation exchange resin Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated
  • an anion exchange resin After removing sodium ions and chloride
  • Example 5 A solution was prepared by dissolving 4 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 11 N (11 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd. prepared from 12 N hydrochloric acid) and heated to 40°C.
  • the solution of Example 2 was obtained by heating.
  • the volume of the obtained solution was 5.0 mL
  • the hydrogen chloride concentration was 11 mol/L (19.1 mass %)
  • the zinc chloride concentration was 6 mol/L (44.4 mass %)
  • the zinc chloride concentration was 6 mol/L (44.4 mass %).
  • the concentration was 0.55 mol per mol of hydrogen chloride.
  • 0.017 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain the solution of Example 5.
  • Example 5 1.6 g of powdered cellulose (Fujifilm Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes with stirring to dissolve the powdered cellulose. The resulting viscous liquid was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 5.
  • the concentration of hydrogen chloride was 11 mol/L (16.2% by mass)
  • the concentration of zinc chloride was 6 mol/L (37.7% by mass)
  • the concentration of glycolic acid was 0.004 mol/L.
  • the concentration of zinc chloride was 0.55 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.0067 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure.
  • a cation exchange resin Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated
  • an anion exchange resin After removing sodium ions and chloride
  • Example 6 A solution was prepared by dissolving 3.3 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 10 N (10 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd. prepared from 12 N hydrochloric acid) and heated at 40°C. The solution of Example 3 was obtained. The volume of the obtained solution was 5.0 mL, the hydrogen chloride concentration was 10 mol/L (19.0 mass %), the zinc chloride concentration was 5 mol/L (36.7 mass %), and the zinc chloride concentration was 5 mol/L (36.7 mass %). The concentration was 0.5 mol per mol of hydrogen chloride. Furthermore, 0.17 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain the solution of Example 6.
  • Example 6 1.6 g of powdered cellulose (Fujifilm Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes with stirring to dissolve the powdered cellulose. The resulting viscous liquid was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 6.
  • the concentration of hydrogen chloride was 10 mol/L (16.1% by mass)
  • the concentration of zinc chloride was 5 mol/L (31.1% by mass)
  • the concentration of glycolic acid was 0.04 mol/L.
  • the concentration of zinc chloride was 0.5 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.008 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure.
  • a cation exchange resin Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated
  • an anion exchange resin After removing sodium ions and chloride
  • Example 7 A solution was prepared by dissolving 4 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 10 N (10 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd.) prepared from 12 N hydrochloric acid, and heated to 40°C. did.
  • the volume of the obtained solution was 5.0 mL
  • the concentration of hydrogen chloride was 10 mol/L (17.5% by mass)
  • the concentration of zinc chloride was 6 mol/L (44.4% by mass)
  • the concentration of hydrogen chloride was 6 mol/L (44.4% by mass).
  • the concentration was 0.6 mol per mol of hydrogen chloride.
  • 1.7 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain the solution of Example 7.
  • Example 7 1.6 g of powdered cellulose (Fujifilm Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes with stirring to dissolve the powdered cellulose. The resulting viscous liquid was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 7.
  • the concentration of hydrogen chloride was 10 mol/L (14.9% by mass)
  • the concentration of zinc chloride was 6 mol/L (37.7% by mass)
  • the concentration of glycolic acid was 0.4 mol/L.
  • the concentration of zinc chloride was 0.6 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.067 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure. A viscous oil was obtained by distilling off. This oil was diluted to 1800 mL in a graduated cylinder, diluted 10 times, and analyzed using LC-MS, and it was confirmed that glucose was produced at a yield of 71%.
  • Example 8 A solution was prepared by dissolving 30 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 25 g of 8N (8 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) prepared from 12N hydrochloric acid, and heated to 40°C. did.
  • the volume of the obtained solution was 25.5 mL
  • the hydrogen chloride concentration was 8 mol/L (9.9 mass %)
  • the zinc chloride concentration was 8 mol/L (61.5 mass %)
  • the zinc chloride concentration was 8 mol/L (61.5 mass %).
  • the concentration was 1.00 mol per mol of hydrogen chloride.
  • 0.082 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain the solution of Example 8.
  • Example 8 8.2 g of powdered cellulose (Fuji Film Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes with stirring to dissolve the powdered cellulose. The resulting viscous liquid was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 8.
  • the hydrogen chloride concentration was 8 mol/L (8.4% by mass)
  • the zinc chloride concentration was 8 mol/L (52.5% by mass)
  • the glycolic acid concentration was 0.08 mol/L.
  • the zinc chloride concentration was 1.00 mol per mol of hydrogen chloride
  • the glycolic acid concentration was 0.01 mol per mol of zinc chloride.
  • composition was diluted with 400 mL of acetone (Fujifilm Wako Pure Chemical Industries, Ltd.).
  • the precipitated solid was collected by filtration, dissolved in 100 mL of water, filtered through a 0.45 ⁇ m membrane filter, and the water was evaporated to obtain 8.7 g (89% yield) of the product glucose as a solid. .
  • Example 9 A solution was prepared by dissolving 2.7 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 12N (8 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) and heated to 40°C. The volume of the obtained solution was 5.0 mL, the concentration of hydrogen chloride was 12 mol/L (23.4% by mass), the concentration of zinc chloride was 4 mol/L (35.1% by mass), and the concentration of hydrogen chloride was 4 mol/L (35.1% by mass). The concentration was 0.33 mol per mol of hydrogen chloride. Furthermore, 0.017 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain the solution of Example 9.
  • Example 9 1.6 g of powdered cellulose (Fujifilm Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes with stirring to dissolve the powdered cellulose. The resulting viscous liquid was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 9.
  • the hydrogen chloride concentration was 12 mol/L (19.9 mass%)
  • the zinc chloride concentration was 4 mol/L (29.8 mass%)
  • the glycolic acid concentration was 0.004 mol/L.
  • the concentration of zinc chloride was 0.33 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.001 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure.
  • a cation exchange resin Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated
  • an anion exchange resin After removing sodium ions and chloride
  • Example 10 A solution was prepared by dissolving 4 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 10 N (10 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd.) prepared from 12 N hydrochloric acid, and heated to 40°C. did.
  • the volume of the obtained solution was 5.0 mL
  • the concentration of hydrogen chloride was 10 mol/L (17.5% by mass)
  • the concentration of zinc chloride was 6 mol/L (44.4% by mass)
  • the concentration of hydrogen chloride was 6 mol/L (44.4% by mass).
  • the concentration was 0.6 mol per mol of hydrogen chloride.
  • 0.023 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain the solution of Example 10.
  • Example 10 1.6 g of crushed pieces of Kimwipe (manufactured by Nippon Paper Crecia Co., Ltd.), a pulp product, cut into approximately 1 cm squares with scissors were added to the resulting solution over 10 minutes with stirring, and the Kimwipe pieces were dissolved. Ta. The resulting viscous liquid was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 10.
  • the concentration of hydrogen chloride was 10 mol/L (17.5% by mass)
  • the concentration of zinc chloride was 6 mol/L (44.4% by mass)
  • the concentration of glycolic acid was 0.006 mol/L.
  • the concentration of zinc chloride was 0.6 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.001 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin.
  • a cation exchange resin Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated
  • Example 11 A solution was prepared by dissolving 4 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 10 N (10 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd.) prepared from 12 N hydrochloric acid, and heated to 40°C. did.
  • the volume of the obtained solution was 5.0 mL
  • the concentration of hydrogen chloride was 10 mol/L (17.5% by mass)
  • the concentration of zinc chloride was 6 mol/L (44.4% by mass)
  • the concentration of hydrogen chloride was 6 mol/L (44.4% by mass).
  • the concentration was 0.6 mol per mol of hydrogen chloride.
  • 0.023 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain a solution of Example 11.
  • Example 11 1.6 g of dry wood flour (manufactured by Minabe Kako Co., Ltd.), which is lignocellulose, was added to the obtained solution over 10 minutes with stirring to disperse the dry wood flour. The resulting dark brown, cloudy, viscous mixture was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 11.
  • the concentration of hydrogen chloride was 10 mol/L (14.9% by mass)
  • the concentration of zinc chloride was 6 mol/L (37.7% by mass)
  • the concentration of glycolic acid was 0.006 mol/L.
  • the concentration of zinc chloride was 0.6 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.001 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained solution (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated dark brown powder containing a mixture of zinc hydroxide and lignin was filtered, and the filtrate was filtered using a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid).
  • a cation exchange resin Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid.
  • Example 12 A solution was prepared by dissolving 20 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 25 g of 10 N (10 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd.) prepared from 12 N hydrochloric acid, and heated to 40°C. did.
  • the volume of the obtained solution was 5.0 mL
  • the concentration of hydrogen chloride was 10 mol/L (17.5% by mass)
  • the concentration of zinc chloride was 6 mol/L (44.4% by mass)
  • the concentration of hydrogen chloride was 6 mol/L (44.4% by mass).
  • the concentration was 0.6 mol per mol of hydrogen chloride.
  • 0.023 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain a solution of Example 12.
  • Example 12 To the obtained solution, 10.0 g of chitin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added over 10 minutes with stirring to dissolve the chitin. The resulting viscous liquid was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 12.
  • the concentration of hydrogen chloride was 10 mol/L (14.3% by mass)
  • the concentration of zinc chloride was 6 mol/L (36.3% by mass)
  • the concentration of glycolic acid was 0.006 mol/L.
  • the concentration of zinc chloride was 0.6 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.001 mol per mol of zinc chloride.
  • composition was diluted with 400 mL of acetone (Fujifilm Wako Pure Chemical Industries, Ltd.).
  • the precipitated solid was collected by filtration, dissolved in 100 mL of water, filtered through a 0.45 ⁇ m membrane filter, and the water was evaporated to obtain 10.8 g (yield 95%) of the product glucose as a solid. .
  • Example 13 A solution was prepared by dissolving 3.3 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 9N (9 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) prepared from 12N hydrochloric acid, and heated to 40°C. Warmed. The volume of the obtained solution was 5.0 mL, the hydrogen chloride concentration was 9 mol/L (16.1 mass %), the zinc chloride concentration was 5 mol/L (39.8 mass %), and the zinc chloride concentration was 5 mol/L (39.8 mass %). The concentration was 0.55 mol per mol of hydrogen chloride. Furthermore, 0.19 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain a solution of Example 13.
  • Example 13 1.6 g of powdered cellulose (Fuji Film Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes while stirring. The resulting viscous mixture was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 13.
  • the concentration of hydrogen chloride was 9 mol/L (13.5% by mass)
  • the concentration of zinc chloride was 5 mol/L (33.4% by mass)
  • the concentration of glycolic acid was 0.05 mol/L.
  • the zinc chloride concentration was 0.55 mol per mol of hydrogen chloride
  • the glycolic acid concentration was 0.01 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained mixture (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure. A viscous oil was obtained by distilling off. This oil was diluted to 1800 mL in a graduated cylinder, diluted 10 times, and analyzed using LC-MS, and it was confirmed that glucose was produced at a yield of 10%.
  • Example 14 A solution was prepared by dissolving 4.6 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 7N (7 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) prepared from 12N hydrochloric acid, and heated to 40°C. Warmed. The volume of the obtained solution was 5.1 mL, the hydrogen chloride concentration was 7 mol/L (11.9 mass %), the zinc chloride concentration was 7 mol/L (47.9 mass %), and the zinc chloride concentration was 7 mol/L (47.9 mass %). The concentration was 1.00 mol per mol of hydrogen chloride. Furthermore, 0.27 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain a solution of Example 14.
  • Example 14 1.6 g of powdered cellulose (Fuji Film Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes while stirring. The resulting viscous mixture was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 14.
  • the concentration of hydrogen chloride was 9 mol/L (10.2% by mass)
  • the concentration of zinc chloride was 5 mol/L (41.1% by mass)
  • the concentration of glycolic acid was 0.05 mol/L.
  • the concentration of zinc chloride was 0.55 mol per mol of hydrogen chloride
  • the concentration of glycolic acid was 0.01 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained mixture (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin. After removing sodium ions and chloride ions by contacting the resin (Amberlite RIRA-900 manufactured by Organo Co., Ltd. by immersing it in 1N sodium hydroxide to activate it and separating it), water was added under reduced pressure. A viscous oil was obtained by distilling off. This oil was diluted to 1800 mL in a graduated cylinder, diluted 10 times, and analyzed using LC-MS, and it was confirmed that glucose was produced at a yield of 8%.
  • Example 15 A solution was prepared by dissolving 2.0 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 5 g of 11N (11 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) prepared from 12N hydrochloric acid, and heated to 40°C. Warmed. The volume of the obtained solution was 5.0 mL, the hydrogen chloride concentration was 11 mol/L (24.6 mass %), the zinc chloride concentration was 3 mol/L (28.5 mass %), and the zinc chloride concentration was 3 mol/L (28.5 mass %). The concentration was 0.27 mol per mol of hydrogen chloride. Furthermore, 0.12 g of glycolic acid (Fuji Film Wako Pure Chemical Industries, Ltd.) as a catalyst was added to obtain a solution of Example 15.
  • Example 15 1.6 g of powdered cellulose (Fuji Film Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes while stirring. The resulting viscous mixture was subsequently stirred at 40° C. for 2 hours to obtain the composition of Example 15.
  • the hydrogen chloride concentration was 11 mol/L (20.0 mass%)
  • the zinc chloride concentration was 3 mol/L (23.2 mass%)
  • the glycolic acid concentration was 0.03 mol/L.
  • the concentration of zinc chloride was 0.27 mol per mol of hydrogen chloride, and the concentration of glycolic acid was 0.01 mol per mol of zinc chloride.
  • a 1 mol/L aqueous sodium hydroxide solution was added to the obtained mixture (composition). At this time, the solution was carefully added while stirring until the pH of the solution was determined to be pH 10 using pH test paper. Thereafter, the precipitated white solid of zinc hydroxide was filtered out, and the filtrate was treated with a cation exchange resin (Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated), and an anion exchange resin.
  • a cation exchange resin Amberlyst R15 manufactured by Organo Co., Ltd., which was activated by immersing it in 1N hydrochloric acid and then separated
  • Example 16 A solution was prepared by dissolving 30 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 25 g of 8N (8 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) prepared from 12N hydrochloric acid, and heated to 40°C. A solution of Example 16 was obtained. The volume of the obtained solution was 5.0 mL, the hydrogen chloride concentration was 8 mol/L, the zinc chloride concentration was 8 mol/L, and the zinc chloride concentration was 1.00 mol per 1 mol of hydrogen chloride. Met.
  • Example 16 8.2 g of wood flour (Minabe Kako Co., Ltd.; water-soluble component 10%) was added to the resulting solution over 10 minutes with stirring to dissolve cellulose, hemicellulose, etc. among the components of the wood flour. .
  • the resulting viscous liquid was continuously stirred at 40°C for 2 hours, then 31.5g of water was added, the temperature was raised to 60°C, and the mixture was stirred for an additional 2 hours, and the solution was filtered to remove insoluble matter. was removed to obtain the composition of Example 16.
  • the hydrogen chloride concentration was 4 mol/L
  • the zinc chloride concentration was 4 mol/L
  • the saccharide concentration was 6.6% by mass
  • the zinc chloride concentration was 1% by mass per mol of hydrogen chloride. It was .00 mol.
  • the remaining oily substance was diluted with 400 mL of acetone (Fujifilm Wako Pure Chemical Industries, Ltd.).
  • the precipitated solid was collected by filtration, dissolved in 100 mL of water, filtered through a 0.45 ⁇ m membrane filter, and the water was evaporated to obtain the product sugar (glucose, mannose, arabinose, xylose mixture) as a solid. .7 g and 2.4 g of insoluble solids were obtained.
  • Example 17 A solution was prepared by dissolving 30 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 25 g of 8N (8 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) prepared from 12N hydrochloric acid, and heated to 40°C. A solution of Example 17 was obtained. The volume of the obtained solution was 5.0 mL, the hydrogen chloride concentration was 8 mol/L, the zinc chloride concentration was 8 mol/L, and the zinc chloride concentration was 1.00 mol per 1 mol of hydrogen chloride. Met.
  • the hydrogen chloride concentration was 8 mol/L
  • the zinc chloride concentration was 8 mol/L
  • the glycolic acid concentration was 0.04 mol/L
  • the N-acetylglucosamine concentration was 16.6% by mass.
  • the concentration of zinc chloride was 1.00 mol per mol of hydrogen chloride
  • the concentration of glycolic acid was 0.005 mol per mol of zinc chloride.
  • composition was diluted with 400 mL of acetone (Wako Pure Chemical Industries, Ltd.).
  • acetone Waako Pure Chemical Industries, Ltd.
  • the precipitated solid was collected by filtration, dissolved in 100 mL of water, filtered through a 0.45 ⁇ m membrane filter, and the water was evaporated to obtain 9.8 g of the product N-acetylglucosamine as a solid.
  • Example 18 A solution was prepared by dissolving 22.5 g of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) in 25 g of 10 N (10 mol/L) hydrochloric acid aqueous solution (Fuji Film Wako Pure Chemical Industries, Ltd.) prepared from 12 N hydrochloric acid, and heated to 60°C. The solution of Example 15 was obtained by heating. The volume of the obtained solution was 5.0 mL, the hydrogen chloride concentration was 10 mol/L, the zinc chloride concentration was 6 mol/L, and the zinc chloride concentration was 0.60 mol per 1 mol of hydrogen chloride. Met.
  • Example 15 8.2 g of powdered cellulose (Fujifilm Wako Pure Chemical Industries, Ltd.; water solubility less than 0.001 g/100 mL) was added to the obtained solution over 10 minutes with stirring to dissolve the powdered cellulose. The resulting viscous liquid was subsequently stirred at 60° C. for 8 hours to obtain the composition of Example 15.
  • the hydrogen chloride concentration was 10 mol/L
  • the zinc chloride concentration was 6 mol/L
  • the zinc chloride concentration was 0.60 mol per 1 mol of hydrogen chloride.
  • composition was diluted with 400 mL of acetone (Fujifilm Wako Pure Chemical Industries, Ltd.).
  • the precipitated solid was collected by filtration, dissolved in 100 mL of water, filtered through a 0.45 ⁇ m membrane filter, and the water was evaporated to obtain the product glucose as a solid.
  • Comparative example 1 55 g of a 12N (12 mol/L) aqueous hydrochloric acid solution (Fuji Film Wako Pure Chemical Industries, Ltd.) was heated to 40° C. to obtain a solution of Comparative Example 1.
  • the concentration of hydrogen chloride was 12 mol/L (37.0% by mass)
  • the concentration of zinc chloride was 0 mol/L
  • the concentration of zinc chloride was 0 mol per mol of hydrogen chloride.
  • the obtained slurry (composition) was filtered, and the solid material was washed three times with water, further washed with ethanol three times, and dried at 115° C. for 3 hours.
  • the solid obtained was 8.2 g of cellulose.
  • Comparative example 2 55 g of a 75% by mass aqueous zinc chloride solution (prepared from zinc chloride manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was heated to 40° C. to obtain a solution of Comparative Example 2. In the obtained solution, the hydrogen chloride concentration was 0 mol/L, and the zinc chloride concentration was 8 mol/L (75% by mass).
  • the obtained slurry (composition) was filtered, and the solid material was washed three times with water, further washed with ethanol three times, and dried at 115° C. for 3 hours.
  • the solid obtained was 8.2 g of cellulose.
  • the resulting mixture was diluted with 100 mL of water, filtered, and the residue was washed with a small amount of acetone and air-dried. As a result, 1.6 g of cellulose was recovered.
  • the resulting mixture was diluted with 100 mL of water, filtered, and the residue was washed with a small amount of acetone and air-dried. As a result, 1.6 g of cellulose was recovered.
  • the resulting mixture was diluted with 100 mL of water, filtered, and the residue was washed with a small amount of acetone and air-dried. As a result, 1.6 g of cellulose was recovered.
  • the obtained slurry (composition) was filtered, and the solid material was washed three times with water, further washed with ethanol three times, and dried at 115° C. for 3 hours.
  • the solid obtained was 8.2 g of cellulose.
  • the obtained slurry (composition) was filtered, and the solid material was washed three times with water, further washed with ethanol three times, and dried at 115° C. for 3 hours.
  • the solid obtained was 8.2 g of cellulose.
  • Comparative example 8 A solution was prepared by dissolving 21.8 g of zinc hydroxide (Fujifilm Wako Pure Chemical Industries, Ltd.) in 25 g of 8N (8 mol/L) hydrochloric acid aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) prepared from 12N hydrochloric acid, and heated to 40°C. The solution of Comparative Example 8 was obtained. In the obtained solution, the hydrogen chloride concentration was 0 mol/L, the zinc hydroxide was partially neutralized to zinc chloride by hydrochloric acid, and the total zinc concentration of zinc hydroxide and zinc chloride was 8 mol/L. Met.
  • the obtained slurry (composition) was filtered, and the solid material was washed three times with water, further washed with ethanol three times, and dried at 115° C. for 3 hours.
  • the solid obtained was 8.2 g of cellulose.

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Abstract

L'invention concerne un procédé de dissolution d'un polysaccharide tel que la cellulose dans des conditions acides et modérées à l'aide d'une solution contenant de l'acide chlorhydrique et du chlorure de zinc, la concentration en chlorure d'hydrogène dans l'acide chlorhydrique étant de 7 à 12 mol/L, la teneur en chlorure de zinc étant de 2 à 10 mol/L, et la quantité totale de la concentration en chlorure d'hydrogène dans l'acide chlorhydrique et la teneur en chlorure de zinc étant de 13 à 20 mol/L. L'invention concerne également un procédé de conversion d'un polysaccharide tel que la cellulose en un monosaccharide ou un oligosaccharide dans des conditions acides et modérées.
PCT/JP2023/033628 2022-09-14 2023-09-14 Procédé de production d'un monosaccharide ou d'un oligosaccharide à partir d'un polysaccharide, solution utilisée dans ledit procédé de production, et composition comprenant un monosaccharide ou un oligosaccharide Ceased WO2024058256A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4452640A (en) * 1982-05-11 1984-06-05 Purdue Research Foundation Quantitative hydrolysis of cellulose to glucose using zinc chloride
JP2011517552A (ja) * 2008-03-13 2011-06-16 バイオイーコン インターナショナル ホールディング エヌ．ブイ． 無機溶融塩水和物中で多糖類を転化する方法
US20120108827A1 (en) * 2009-03-17 2012-05-03 Bioecon International Holding N.V. Process for converting polysaccharides in an inorganic molten salt hydrate
WO2013110814A1 (fr) * 2012-01-27 2013-08-01 Bioecon International Holding N.V. Procédé destiné à la récupération de saccharides à partir d'un mélange réactionnel d'hydrolyse de cellulose
US20170226144A1 (en) * 2016-02-04 2017-08-10 Industrial Technology Research Institute Method for separating hydrolyzed product of biomass

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4452640A (en) * 1982-05-11 1984-06-05 Purdue Research Foundation Quantitative hydrolysis of cellulose to glucose using zinc chloride
JP2011517552A (ja) * 2008-03-13 2011-06-16 バイオイーコン インターナショナル ホールディング エヌ．ブイ． 無機溶融塩水和物中で多糖類を転化する方法
US20120108827A1 (en) * 2009-03-17 2012-05-03 Bioecon International Holding N.V. Process for converting polysaccharides in an inorganic molten salt hydrate
WO2013110814A1 (fr) * 2012-01-27 2013-08-01 Bioecon International Holding N.V. Procédé destiné à la récupération de saccharides à partir d'un mélange réactionnel d'hydrolyse de cellulose
US20170226144A1 (en) * 2016-02-04 2017-08-10 Industrial Technology Research Institute Method for separating hydrolyzed product of biomass

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"The 16th Series of Experimental Chemistry, Analysis of Organic Compounds.", 1 January 1958, MARUZEN CO., LTD, JP, article "Passage; The 16th Series of Experimental Chemistry, Analysis of Organic Compounds.", pages: 279 - 282, XP009555127 *

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