CN109796508B - Method for preparing high-purity xylo-oligosaccharide - Google Patents
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Abstract
The invention relates to a method for preparing high-purity xylo-oligosaccharide, which comprises the steps of firstly, using active carbon to carry out adsorption treatment on a solution obtained by removing lignin from black liquor or plant extract, and carrying out solid-liquid separation to obtain a purified liquor I; then, adsorbing monosaccharide in the purified liquid I by using strong acid cation exchange resin; and mixing the purified liquid II obtained after adsorption with an organic solvent, removing impurities through purification and extraction treatment, and concentrating and crystallizing the xylo-oligosaccharide solution obtained after impurity removal to obtain the high-purity xylo-oligosaccharide. The method takes the solution of the black liquor or the plant extract without the lignin as the raw material, and the high-purity xylo-oligosaccharide with the purity of more than 95 percent is prepared by the steps of activated carbon decoloration, adsorption, strong acid cation exchange resin adsorption, organic solvent purification extraction treatment and the like in sequence, thereby realizing the full utilization of resources and having good economic benefit and application prospect.
Description
Technical Field
The invention relates to the field of plant separation and recovery, and particularly relates to a method for preparing high-purity xylooligosaccharide.
Background
The xylo-oligosaccharide is also called xylo-oligosaccharide, and is a functional polysaccharide formed by combining 2-7 xylose molecules by beta-1, 4 glycosidic bonds. Compared with other oligosaccharides, xylo-oligosaccharide has good stability and is hardly decomposed by human digestive enzymes. Xylo-oligosaccharide can selectively promote the proliferation activity of intestinal bifidobacteria, the bifidus factor function of the xylo-oligosaccharide is 10-20 times of that of other polymeric saccharides, and the xylo-oligosaccharide has been widely noticed because of various effects of reducing the production of toxic fermentation products and harmful bacterial enzymes, inhibiting pathogenic bacteria and diarrhea, preventing constipation, protecting liver function, reducing serum cholesterol, reducing blood pressure, enhancing immunity of organism, resisting cancer and the like.
At present, the industrial production of xylo-oligosaccharide generally uses acid hydrolysis method, enzyme hydrolysis method, microwave degradation method, hot water extraction method and the like. The product is single and has low utilization rate of raw materials, wherein the acid hydrolysis method cannot be effectively popularized due to high requirements on equipment, harsh reaction conditions, easy generation of harmful substances in the production process and low product yield.
The existing xylo-oligosaccharide preparation generally takes lignocellulose rich in xylan as a raw material, mainly takes corn cobs, wheat bran, bagasse and other crops as main materials, has single raw material and limits the large-scale production of xylo-oligosaccharide.
In the traditional pulping industry, the raw fiber pulp and the cooking black liquor are obtained by separation after cooking, the black liquor is directly discharged into rivers to cause pollution, and the black liquor is generally directly used for combustion and heating to provide heat energy. At present, with the pressure on environmental protection and the requirement on full utilization of resources, more and more researches are made on the black liquor cooking. However, the research focuses only on recovering lignin in the cooking black liquor, and no effective recovery and purification method exists for hemicellulose separated from plant raw materials in the cooking black liquor.
In addition to the pulping industry, the same problem exists in the industries such as biorefinery, and if the plant raw materials are treated by different treatment methods and cellulose is extracted to obtain plant extract, the plant extract is not efficiently utilized, so that the resource waste is caused.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a method for preparing high-purity xylo-oligosaccharide, which takes the solution obtained by removing lignin from black liquor or plant extract as a raw material to prepare the high-purity xylo-oligosaccharide.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a method for preparing high-purity xylo-oligosaccharide, which comprises the following steps:
(1) adsorbing the solution of the black liquor or the plant extract after removing the lignin by using active carbon, and carrying out solid-liquid separation after the treatment is finished to obtain a purified liquor I;
(2) adsorbing and eluting the purified liquid I obtained in the step (1) by using strong acid cation exchange resin to obtain a purified liquid II;
(3) and (3) mixing the purified liquid II obtained in the step (2) with an organic solvent, carrying out purification and extraction treatment to obtain a xylo-oligosaccharide solution, and carrying out concentration and crystallization on the solution to obtain the high-purity xylo-oligosaccharide.
The invention relates to a solution obtained by removing lignin from black liquor or plant extracting solution, wherein the black liquor refers to the cooking black liquor obtained by any cooking section in the pulping field, and the plant extracting solution refers to the plant extracting solution obtained by extracting cellulose components in the biorefinery field. In fact, in the field of plant component separation, the solution obtained by removing lignin from the treatment liquid (black liquid or plant extract) generated after removing the cellulose component is suitable for the present invention, and the present invention is not particularly limited to the obtained black liquid or plant extract and the method for removing lignin from the black liquid or plant extract.
For example, the solution of the plant extract after delignification can be obtained by the following method, but is not limited to the following method:
mixing a raw material containing wood fibers with organic acid such as formic acid or acetic acid, cooking, performing solid-liquid separation to obtain primary fiber pulp and a plant extracting solution, recovering the organic acid in the plant extracting solution in a concentration mode, adding water into the concentrated solution for precipitation, and removing lignin after the solid-liquid separation to obtain a solution of the plant extracting solution after the lignin is removed.
The high-purity xylo-oligosaccharide of the invention refers to xylo-oligosaccharide with the purity of more than or equal to 90 percent.
According to the invention, the mass of the activated carbon in the adsorption treatment in step (1) is 0.5-5% of the solution, which may be, for example, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, etc., and the invention is not exhaustive for reasons of brevity and simplicity.
According to the invention, after solid-liquid separation in the step (1), purified liquid I and adsorbed activated carbon are obtained, and the adsorbed activated carbon can be selectively heated for regeneration and then repeatedly utilized.
The kind of the strong acid cation exchange resin in step (2) is not particularly limited in the present invention, as long as the effect of adsorbing monosaccharides is achieved. The strong acid cation exchange resin may be, for example, 001x7, 201x7/205x7, 201x7, 001x4, 001x14, 005x7, D72, D61, D001-CC, D81, NKC-9 dry hydrogen resin, or the like, but is not limited thereto.
According to the invention, the specific operation of step (2) is: and (2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification liquid I obtained in the step (1), adsorbing monosaccharide in the purification liquid I, and then eluting.
For example, the above operations may be: the strong acid cation exchange resin is soaked by hydrochloric acid aqueous solution and washed to be neutral, then soaked by sodium hydroxide aqueous solution and washed to be neutral, and finally packed into a column.
In the elution process, the temperature of elution is 40-80 ℃, the eluent is distilled water, the elution flow rate is 1-6mL/min, and the eluent is collected.
According to the invention, the organic solvent in the step (3) is at least one of an alcohol solvent, an ether solvent or an ester solvent. Wherein, the alcohol solvent is preferably methanol or ethanol; the ether solvent is preferably diethyl ether; the ester solvent is preferably ethyl acetate or butyl acetate.
According to the invention, the mass ratio of the organic solvent to the purified liquid II in the extraction treatment in step (3) is (0.5-3):1, and may be, for example, 0.5:1, 1:1, 1.5:1, 2:1, 2.5:1 or 3:1, etc., and the invention is not exhaustive for reasons of space and simplicity.
According to the invention, the extraction treatment in the step (3) is preferably three-stage extraction, namely three times of extraction and purification are carried out according to the addition amount of the extracting agent.
According to the invention, the specific operations of the purification and extraction treatment for removing impurities in the step (3) are as follows: and (3) uniformly mixing the purified liquid II with an organic solvent, and extracting impurities by using the organic solvent at the temperature of 30-80 ℃ and the rotating speed of 10-200 r/min.
According to the invention, the organic phase containing impurities can be recycled after the solvent (organic phase) is recovered after vacuum evaporation.
According to the invention, the purity of the xylo-oligosaccharide obtained after the concentration and crystallization in the step (3) is more than 95 percent.
As a preferred technical scheme, the method for preparing the high-purity xylo-oligosaccharide comprises the following steps:
(1) adsorbing the solution of the black liquor or the plant extract without the lignin by using active carbon, controlling the mass of the active carbon to be 0.5-5% of the solution, performing solid-liquid separation after the treatment is finished to obtain the active carbon and a purification solution I, heating the obtained active carbon for regeneration, and then recycling;
(2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification solution I obtained in the step (1), adsorbing monosaccharide in the purification solution I, and then eluting the purification solution I at the temperature of 40-80 ℃ and the flow rate of 1-6mL/min to obtain a purification solution II;
(3) mixing the purified liquid II obtained after monosaccharide adsorption in the step (2) with an organic solvent, extracting impurities by using the organic solvent at the temperature of 30-80 ℃ and the rotating speed of 10-200r/min, adopting three-stage extraction, controlling the mass ratio of the organic solvent to the purified liquid II to be (0.5-3) to 1 in the extraction treatment process, and repeatedly using the organic phase obtained by extracting the impurities after vacuum evaporation and solvent recovery; and concentrating and crystallizing the xylo-oligosaccharide solution obtained after impurity removal to obtain the xylo-oligosaccharide with the purity of more than 95 percent.
Compared with the prior art, the invention has at least the following beneficial effects:
the method takes the solution of the black liquor or the plant extract after the lignin is removed as the raw material, firstly, the solution is decolorized by active carbon, and meanwhile, heavy metal ions and part of macromolecular organic matters in the solution are adsorbed, so that the influence of subsequent purification and separation is reduced; then, the separation and purification are carried out by utilizing the factors that the sugar with different properties and different molecular weights and metal cations form coordination complexes and the properties of xylo-oligosaccharide and other monosaccharides are different; and then the phenol-containing substances and the extract in the sugar solution are extracted by utilizing the principle that the organic solvent is similar to and compatible with each other, so that the xylo-oligosaccharide is further subjected to impurity removal. The high-purity xylo-oligosaccharide is finally prepared, the purity of the obtained xylo-oligosaccharide is more than 95 percent and can reach more than 96.5 percent at most, the full utilization of resources is realized, and the method has good economic benefit and application prospect.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the following examples are set forth herein. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The raw materials treated in the embodiments 1-3 of the invention are solutions obtained by removing lignin from the obtained plant extract after treating plant fiber raw materials by an acetic acid method; the raw material treated in example 4 is a solution obtained by delignifying the obtained cooking black liquor after treating the plant fiber raw material in the sulfite pulping process. The raw material treated in example 5 was a solution obtained by recovering lignin from a plant extract obtained by subjecting a plant fiber raw material to alkali treatment and oxidation treatment.
Typical but non-limiting examples of the invention are as follows:
example 1
(1) Performing adsorption treatment on the solution obtained after the plant extracting solution is subjected to lignin removal by using activated carbon, controlling the mass of the activated carbon to be 3% of that of the solution, and filtering after the treatment is finished to obtain activated carbon and a purification solution I, wherein the activated carbon can be regenerated by heating and then recycled;
(2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification solution I obtained in the step (1), adsorbing monosaccharide in the purification solution I, and then eluting the purification solution I at the temperature of 80 ℃ and the flow rate of 2.5mL/min to obtain a purification solution II;
(3) uniformly mixing the purified liquid II obtained after monosaccharide adsorption in the step (2) with diethyl ether, extracting impurities in the purified liquid II by using the diethyl ether at the temperature of 50 ℃ and the rotating speed of 100r/min, adopting three-stage extraction, controlling the mass ratio of an organic solvent to the purified liquid II to be 1:1, and recycling the solvent after an extraction phase is subjected to vacuum evaporation; and concentrating and crystallizing the raffinate phase, and removing residual water to obtain the high-purity xylooligosaccharide.
The purity of the xylo-oligosaccharide prepared by the embodiment is 96.7 percent through detection.
Example 2
(1) Performing adsorption treatment on the solution obtained after the plant extracting solution is subjected to lignin removal by using activated carbon, controlling the mass of the activated carbon to be 0.5% of the solution, and filtering after the treatment is finished to obtain activated carbon and a purification solution I, wherein the activated carbon can be regenerated by heating and then recycled;
(2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification solution I obtained in the step (1), adsorbing monosaccharide in the purification solution I, and then eluting the purification solution I at the temperature of 60 ℃ and the flow rate of 5mL/min to obtain a purification solution II;
(3) uniformly mixing the purified liquid II obtained after monosaccharide adsorption in the step (2) with ethanol, extracting impurities in the purified liquid II by using the ethanol at 40 ℃ and the rotating speed of 120r/min, adopting three-stage extraction, controlling the mass ratio of an organic solvent to the purified liquid II to be 2:1, and recycling the solvent from an extraction phase through vacuum evaporation; and concentrating and crystallizing the raffinate phase, and removing residual water to obtain the high-purity xylooligosaccharide.
The purity of the xylo-oligosaccharide prepared by the embodiment is 95.3 percent through detection.
Example 3
(1) Performing adsorption treatment on the solution obtained after the plant extracting solution is subjected to lignin removal by using activated carbon, controlling the mass of the activated carbon to be 5% of that of the solution, and filtering after the treatment is finished to obtain activated carbon and a purification solution I, wherein the activated carbon can be regenerated by heating and then recycled;
(2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification solution I obtained in the step (1), adsorbing monosaccharide in the purification solution I, and then eluting the purification solution I at the temperature of 50 ℃ and the flow rate of 4mL/min to obtain a purification solution II;
(3) uniformly mixing the purified liquid II obtained after monosaccharide adsorption in the step (2) with ethanol, extracting impurities in the purified liquid II by using the ethanol at 40 ℃ and the rotating speed of 150r/min, adopting three-stage extraction, controlling the mass ratio of an organic solvent to the purified liquid II to be 3:1, and recycling the solvent from an extraction phase through vacuum evaporation; and concentrating and crystallizing the raffinate phase, and removing residual water to obtain the high-purity xylooligosaccharide.
The purity of the xylo-oligosaccharide prepared by the embodiment is 96.2 percent through detection.
Example 4
(1) Performing adsorption treatment on the solution of the black liquor after removing the lignin by using activated carbon, controlling the mass of the activated carbon to be 3% of the solution, and filtering after the treatment to obtain activated carbon and purified liquor I, wherein the activated carbon can be regenerated by heating and then recycled;
(2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification solution I obtained in the step (1), adsorbing monosaccharide in the purification solution I, and then eluting the purification solution I at the temperature of 80 ℃ and the flow rate of 6mL/min to obtain a purification solution II;
(3) uniformly mixing the purified liquid II obtained after monosaccharide adsorption in the step (2) with ethyl acetate, extracting impurities in the purified liquid II by using ethyl acetate at the temperature of 80 ℃ and the rotating speed of 200r/min, adopting three-stage extraction, controlling the mass ratio of an organic solvent to the purified liquid II to be 1.5:1, and recycling the solvent from an extraction phase through vacuum evaporation; and concentrating and crystallizing the raffinate phase, and removing residual water to obtain the high-purity xylooligosaccharide.
The purity of the xylo-oligosaccharide prepared by the embodiment is 95.7 percent through detection.
Example 5
(1) Performing adsorption treatment on the solution obtained after the plant extracting solution is subjected to lignin removal by using activated carbon, controlling the mass of the activated carbon to be 5% of that of the solution, and filtering after the treatment is finished to obtain activated carbon and a purification solution I, wherein the activated carbon can be regenerated by heating and then recycled;
(2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification solution I obtained in the step (1), adsorbing monosaccharide in the purification solution I, and then eluting the purification solution I at the temperature of 40 ℃ and the flow rate of 1mL/min to obtain a purification solution II;
(3) uniformly mixing the purified liquid II obtained after monosaccharide adsorption in the step (2) with ethyl acetate, extracting impurities in the purified liquid II by using ethyl acetate at the temperature of 30 ℃ and the rotating speed of 200r/min, adopting three-stage extraction, controlling the mass ratio of an organic solvent to the purified liquid II to be 2:1, and recycling the solvent after an extraction phase is subjected to vacuum evaporation; and concentrating and crystallizing the raffinate phase, and removing residual water to obtain the high-purity xylooligosaccharide.
The purity of the xylo-oligosaccharide prepared by the embodiment is 96.5 percent through detection.
The applicant states that the present invention is illustrated by the above examples to show the detailed process equipment and process flow of the present invention, but the present invention is not limited to the above detailed process equipment and process flow, i.e. it does not mean that the present invention must rely on the above detailed process equipment and process flow to be implemented. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (5)
1. A method for preparing high-purity xylo-oligosaccharide is characterized by comprising the following steps:
(1) adsorbing the solution of the black liquor or the plant extract after removing the lignin by using active carbon, controlling the mass of the active carbon to be 0.5-5% of the solution, and performing solid-liquid separation after the treatment to obtain a purified solution I; heating the adsorbed activated carbon for regeneration, and then recycling;
(2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification solution I obtained in the step (1), adsorbing monosaccharide in the purification solution I, and then eluting the purification solution I at the temperature of 40-80 ℃ and the flow rate of 1-6mL/min to obtain a purification solution II;
(3) mixing the purified liquid II obtained in the step (2) with an organic solvent, performing purification extraction treatment to obtain a xylo-oligosaccharide solution, and performing concentration crystallization on the solution to obtain high-purity xylo-oligosaccharide; the purification extraction treatment is three-stage extraction, the organic solvent is at least one of an alcohol solvent, an ether solvent or an ester solvent, and the mass ratio of the organic solvent to the purification liquid II is (0.5-3): 1.
2. The method according to claim 1, wherein the purification and extraction treatment of step (3) is carried out by the following specific operations: and (3) uniformly mixing the purified liquid II with an organic solvent, and extracting impurities by using the organic solvent at the temperature of 30-80 ℃ and the rotating speed of 10-200 r/min.
3. The method of claim 2, wherein the organic phase from the extraction of impurities is recycled after solvent recovery by vacuum evaporation.
4. The method of claim 1, wherein the purity of the xylo-oligosaccharide obtained after the concentration and crystallization in the step (3) is more than 95%.
5. The method according to any one of claims 1 to 4, characterized in that it comprises the steps of:
(1) adsorbing the solution of the black liquor or the plant extract after removing the lignin by using active carbon, controlling the mass of the active carbon to be 0.5-5% of the solution, carrying out solid-liquid separation after the treatment is finished to obtain the active carbon and a purified solution I, heating the obtained active carbon for regeneration, and then recycling the active carbon;
(2) washing the strong acid cation exchange resin to be neutral, then loading the column, introducing the purification solution I obtained in the step (1), adsorbing monosaccharide in the purification solution I, and then eluting the purification solution I at the temperature of 40-80 ℃ and the flow rate of 1-6mL/min to obtain a purification solution II;
(3) mixing the purified liquid II obtained after monosaccharide adsorption in the step (2) with an organic solvent, extracting impurities by using the organic solvent at the temperature of 30-80 ℃ and the rotating speed of 10-200r/min, adopting three-stage extraction, controlling the mass ratio of the organic solvent to the purified liquid II to be (0.5-3) to 1 in the extraction treatment process, and repeatedly using the organic phase obtained by extracting the impurities after vacuum evaporation and solvent recovery; and concentrating and crystallizing the xylo-oligosaccharide solution obtained after impurity removal to obtain the xylo-oligosaccharide with the purity of more than 95 percent.
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| CN110295510B (en) * | 2019-06-27 | 2021-10-01 | 大连工业大学 | Method for preparing lignin crude product and sugar solution by using pulping and papermaking waste liquor |
| CN112608352B (en) * | 2020-11-30 | 2022-05-03 | 济南茂腾生物科技有限公司 | Method for preparing high-purity xylo-oligosaccharide |
| CN114163486A (en) * | 2021-12-22 | 2022-03-11 | 云南三七科技有限公司 | Method for preparing oligosaccharide from pseudo-ginseng |
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| CN104313081A (en) * | 2014-10-23 | 2015-01-28 | 中国制浆造纸研究院 | Method for preparing xylooligosaccharide by utilizing viscose fiber to squeeze waste alkaline liquor |
| CN106188345B (en) * | 2016-08-16 | 2018-05-11 | 南京林业大学 | A kind of method that xylo-oligosaccharide and lignosulfonates are synchronously extracted in the preprocessing plant fibre waste liquid from neutral sulfite |
| CN107502632A (en) * | 2017-08-28 | 2017-12-22 | 无锡群硕谷唐生物科技有限公司 | A kind of method that xylo-oligosaccharide is prepared using bagasse pulp black liquid extraction |
| CN107587373B (en) * | 2017-11-01 | 2019-02-01 | 广西大学 | A kind of method of grading extraction black liquor and wood oligose |
| CN109439695B (en) * | 2018-08-31 | 2021-08-17 | 山东龙力生物科技股份有限公司 | Method for co-producing xylooligosaccharide, xylose and xylitol by industrial waste |
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