WO2021032195A1 - 一种从杂糖液中分离木糖与木质素的方法 - Google Patents
一种从杂糖液中分离木糖与木质素的方法 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/005—Lignin
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
- C13K13/002—Xylose
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
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- the invention belongs to the field of comprehensive utilization of biomass. Specifically, the present invention relates to a method for separating hemicellulose and lignin from a mixed sugar liquid, especially a method for separating xylose and lignin from a mixed sugar liquid.
- cellulose is mainly used.
- hemicellulose and lignin are usually sold as waste liquid or as low-value products or burned to produce heat, which cannot be used for high value.
- hemicellulose and lignin are usually sold as waste liquid or as low-value products or burned to produce heat, which cannot be used for high value.
- xylose production process only the hemicellulose is used to prepare pure xylose, and the lignin and cellulose are burned as waste residue.
- Chinese patent CN109234468A relates to a method for extracting xylose and lignin from the hydrolysate produced in the process of producing dissolving pulp.
- the patent mentions a method for extracting xylose and lignin from a mixed sugar liquid.
- the hydrolysis reaction of the mixed sugar liquid uses a single phase (water Phase) is hydrolyzed, and after the hydrolysis is completed, lignin is obtained in the form of concentration and filtration.
- the single-phase hydrolysis reaction is carried out in an acidic environment at 120-180°C, and the lignin is easily coked and carbonized, which affects normal production.
- the lignin obtained by concentration and filtration in the later stage not only changes its structure at high temperature, but also contains partially carbonized lignin with relatively low purity.
- Chinese patent CN108411044A relates to an ultrasonic-assisted purification method of xylose in eucalyptus hot water pre-hydrolyzed solution.
- the patent proposes an ultrasonic-assisted method for extracting xylose mainly relying on activated carbon to adsorb lignin in mixed sugar solution.
- the cost of adsorbing lignin by activated carbon is relatively high, and neither the analysis of lignin nor the regeneration of activated carbon after the adsorption is mentioned.
- the first technical problem to be solved by the present invention is to provide a method for extracting xylose and lignin to solve the problem of lignin scaling during the hydrolysis reaction of the mixed sugar liquid in the prior art.
- the second technical problem to be solved by the present invention is to provide a method for extracting xylose and lignin.
- the lignin obtained by the method has high purity, high reaction activity and excellent performance.
- the third technical problem to be solved by the present invention is to provide a method for extracting xylose and lignin, which has simple operation and low production cost, which is beneficial to actual production.
- the present invention provides a method for separating xylose and lignin from mixed sugar liquid, characterized in that the method includes the following steps:
- the separated aqueous phase undergoes the steps of chromatography, ion exchange and crystallization to obtain pure xylose;
- the separated solvent phase part continues to be recycled to the next batch of hydrolysis step.
- the solvent is recovered by vacuum evaporation equipment, and the recovered solvent is recycled back to the hydrolysis step. Used as a solvent, pure lignin is obtained after vacuum evaporation and solvent recovery.
- the miscellaneous sugar liquid contains 20-40% sugar components of the total miscellaneous sugar liquid, wherein monosaccharides in the sugar component account for 5-15% of the total sugar components, and polysaccharides account for 85 percent of the total sugar components. -95%;
- the miscellaneous sugar liquid also contains lignin and dissolved salts that account for 60-70% of the total miscellaneous sugar liquid.
- the solvent used in the hydrolysis step includes: MIBK (also known as “methyl isobutyl ketone”), n-butanol, toluene and isophorone (also known as “1,1,3-trimethyl ring One or a combination of two or more in “hexenone”).
- the mass ratio of the mixed sugar liquid to the solvent is 1:1-4:1.
- the acid catalyst comprises: one or a combination of two or more of sulfuric acid, hydrochloric acid, nitric acid and phosphoric acid.
- the content of the acid catalyst is 3-6 mass% of the mass of the miscellaneous sugar liquid.
- the hydrolysis reaction is a hydrolysis reaction at 90-120°C for 1-5 h.
- the separated solvent phase part can be recycled back to the hydrolysis step for several times up to 8 times.
- the solvent is recovered and the lignin separated by vacuum evaporation equipment.
- the solvent recovery rate reaches 99.5% or more.
- the lignin is well protected in organic solvents, and the lignin obtained in the later stage has high reactivity and excellent performance.
- the lignin yield is higher than 90%, and the purity is high, and the economic value is high.
- Figure 1 is a process flow diagram of the present invention.
- the miscellaneous sugar liquid contains 0.1-99% by weight of the sugar component of the total miscellaneous sugar liquid. In one embodiment, the miscellaneous sugar liquid contains 1-50% by weight of the sugar component of the total miscellaneous sugar liquid. In one embodiment, the mixed sugar liquid contains 5-50% by weight of the sugar component of the total mixed sugar liquid. In one embodiment, the miscellaneous sugar liquid contains 10-40% by weight of sugar components of the total miscellaneous sugar liquid. In one embodiment, the mixed sugar liquid contains 20-40% by weight of the sugar component of the total mixed sugar liquid. In one embodiment, monosaccharides in the sugar component account for 1-30% by weight of the total sugar component.
- monosaccharides in the sugar component account for 5-15% by weight of the total sugar component.
- polysaccharides comprise 70-99% by weight of the total sugar component.
- polysaccharides comprise 85-95% by weight of the total sugar component.
- miscellaneous sugar liquid means that biomass raw materials (including but not limited to wood chips, reeds, rice straw, straw, etc.) are hydrolyzed by hot water or thermal acid, and hemicellulose, part of lignin and a small amount of cellulose are dissolved Into the aqueous solution to obtain a mixed sugar solution.
- biomass raw materials including but not limited to wood chips, reeds, rice straw, straw, etc.
- the miscellaneous sugar liquid in addition to the monosaccharides and polysaccharides, also contains 50-80% by weight of the total miscellaneous sugar liquid and dissolved salt components. In one embodiment, in addition to the monosaccharides and polysaccharides, the miscellaneous sugar liquid also contains 60-70% by weight of lignin and dissolved salt components of the total miscellaneous sugar liquid.
- the pH of the mixed sugar liquid is 1-5. In one embodiment, the pH of the mixed sugar solution is 2-4. In one embodiment, the pH of the mixed sugar liquid is 2.5-3.5.
- the solvent used in the hydrolysis step contains one or a combination of two or more of MIBK, n-butanol, toluene, and isophorone. In one embodiment, the solvent used in the hydrolysis step is any one of MIBK, n-butanol, toluene and isophorone. In one embodiment, the solvent used in the hydrolysis step is MIBK. In one embodiment, the solvent used in the hydrolysis step is n-butanol. In one embodiment, the solvent used in the hydrolysis step is toluene. In one embodiment, the solvent used in the hydrolysis step is isophorone.
- the hydrolysis reaction is carried out at 90-120°C. In one embodiment, the hydrolysis reaction is carried out at 90-110°C.
- the hydrolysis reaction is carried out in an acidic environment of 120-180°C.
- the inventor found that using such a high temperature has certain advantages, such as a small amount of acid, but the disadvantages are even more obvious.
- the lignin has been carbonized and coked, which causes the lignin to be easily coked and carbonized, which affects the normal production.
- the lignin obtained by concentration and filtration in the later stage not only changes in structure at high temperature, but also contains partially carbonized lignin with relatively low purity.
- most of the solutions to the lignin coking fouling during the hydrolysis process are to sulfonate lignin into water-soluble lignosulfonate for separation, but the process is complicated and the cost is high.
- the inventors tried to appropriately lower the temperature, such as carrying out the hydrolysis reaction at 90-120°C, preferably 90-110°C, and adding a certain solvent to solve the problem of lignin carbonization and scaling, and the method is simple and the cost is low.
- Solvents used in the present invention such as MIBK (also known as “methyl isobutyl ketone”), n-butanol, toluene and isophorone (also known as “1,1,3-trimethylcyclohexenone”)
- MIBK also known as "methyl isobutyl ketone”
- n-butanol toluene
- isophorone also known as “1,1,3-trimethylcyclohexenone
- the hydrolysis reaction is carried out for 1-5 h. In one embodiment, in one embodiment, the hydrolysis reaction is carried out for 1-4 h. In one embodiment, in one embodiment, the hydrolysis reaction is carried out for 2-4 h. In one embodiment, in one embodiment, the hydrolysis reaction proceeds for 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, or 5 hours.
- the acid catalyst in the hydrolysis step, includes sulfuric acid, hydrochloric acid, nitric acid, and phosphoric acid. In one embodiment, in the hydrolysis step, the acid catalyst is sulfuric acid. In one embodiment, in the hydrolysis step, the acid catalyst is hydrochloric acid. In one embodiment, in the hydrolysis step, the acid catalyst is nitric acid. In one embodiment, in the hydrolysis step, the acid catalyst is phosphoric acid. In one embodiment, in the hydrolysis step, it is also feasible to use other commonly used acid catalysts, such as sulfur dioxide.
- the separated solvent phase portion is passed through a vacuum evaporation device to recover the solvent, and the recovered solvent is recycled back to the hydrolysis step for use as a solvent several times up to 8 times. This also reflects the high solubility of the solvent to lignin and the economic feasibility of the solution.
- the solvent in the separation step, after the solid content (ie, the solid content) in the separated solvent phase portion reaches 50% or more, the solvent is recovered by a vacuum evaporation device.
- the solid content in the organic phase gradually increases during the solvent recycling process, and when the solid content reaches more than 50%, the solvent and lignin are recovered by a vacuum evaporation concentration device.
- solid content in this application refers to the percentage of the solid content in the solvent phase to the weight of the solvent phase.
- the solvent recovery rate reaches 99.5% or more.
- the solvent recovery rate refers to the pure solvent that can be recovered.
- the solvent recovery rate refers to the percentage of the recovered solvent to the total amount of the initially added solvent. It can be seen that the method of the present invention is as high as 99.5% The initial solvent can be recycled and reused.
- the method of the present invention can efficiently recover xylose and lignin at the same time, wherein the extraction rate of xylose can reach more than 85%, and the recovery rate of lignin can reach more than 90%.
- the xylose extraction rate is calculated based on the distilled aldehyde content of the miscellaneous sugar solution to calculate the original xylose content, and then the xylose extraction is obtained by dividing the total amount of xylose after hydrolysis by the total amount of xylose in the miscellaneous sugar solution before hydrolysis.
- the recovery rate of lignin is obtained by dividing the total amount of lignin powder obtained after rotary evaporation and drying by the total amount of lignin in the stock solution. It can be seen that the method of the present invention can achieve simultaneous extraction of wood with high extraction rate. Sugar, while recovering lignin with a high lignin recovery rate.
- the mass fraction of "distilled aldehyde” in this application refers to weighing a certain mass of mixed sugar liquid, azeotrope with 12% hydrochloric acid, the polypentose in the mixed sugar liquid is hydrolyzed to produce pentose, and the pentose is further dehydrated into furfural , The distilled furfural is condensed and collected in the receiving bottle.
- Use volumetric method or colorimetric method to quantitatively determine the percentage of distilled furfural The specific measurement method is detailed in the national standard GB/T2677.9-1994.
- the pH of the mixed sugar liquid is 3.10, the solid content is 8.90%, and the distilled aldehyde is 1.81%;
- the main components of the mixed sugar liquid are: xylose 1.30%, glucose 0.30%, galactose 0.13%, arabinose 0.30%, xylan 1.08%, and lignin 5.16%.
- the content of each component in the miscellaneous sugar liquid of each example and comparative example was determined by conventional methods in the art.
- the tetrasaccharide content in the water phase is 0.29% glucose, 2.77% xylose, 0.13% galactose, and 0.31% arabinose.
- the extraction rate of xylose reached 88.14%.
- the water phase is processed into pure xylose through the existing xylose production technology;
- the solid content of the organic phase is 6.89%, which is directly reused in the next hydrolysis process of the miscellaneous sugar liquid.
- the solid content of the organic phase reaches 50%, the lignin solid is obtained by vacuum concentration and drying, and the lignin recovery rate can reach 90% the above.
- the pH of the mixed sugar liquid is 3.10, the solid content is 8.90%, and the distilled aldehyde is 1.81%;
- the main components of the mixed sugar liquid are: xylose 1.30%, glucose 0.30%, galactose 0.13%, arabinose 0.30%, xylan 1.08%, and lignin 5.16%.
- the content of tetrasaccharides in the water phase is 0.16% glucose, 2.89% xylose, 0.13% galactose, and 0.29% arabinose.
- the extraction rate of xylose reaches 91.57%; the water phase is processed into pure xylose through the existing xylose technology;
- the solid content of the organic phase is 11.67%, which is directly reused in the next hydrolysis process of the miscellaneous sugar liquid.
- the solid content of the organic phase reaches 50%, the lignin solid is obtained by vacuum concentration and drying, and the lignin recovery rate can reach 90% the above.
- the pH of the mixed sugar liquid is 3.31, the solid content is 10.19%, and the distilled aldehyde is 2.11%;
- miscellaneous sugar liquid The main components of the miscellaneous sugar liquid are: 1.80% xylose, 0.30% glucose, 0.13% galactose, 0.29% arabinose, 1.01% xylan, and 5.98% lignin.
- the content of tetrasaccharides in the water phase is 0.36% glucose, 3.38% xylose, 0.12% galactose, and 0.33% arabinose.
- the extraction rate of xylose reached 90.58%.
- the water phase is processed into pure xylose through the existing xylose production technology;
- the solid content of the organic phase is 7.55%, which is directly reused in the next hydrolysis process of the miscellaneous sugar liquid.
- the solid content of the organic phase reaches 50%, the lignin solid is obtained by vacuum concentration and drying, and the lignin recovery rate can reach 90% the above.
- the pH of the mixed sugar liquid is 3.31, the solid content is 10.19%, and the distilled aldehyde is 2.11%;
- the main components of the mixed sugar liquid are: 1.80% xylose, 0.26% glucose, 0.13% galactose, 0.49% arabinose, 1.01% xylan, and 5.98% lignin.
- the content of tetrasaccharides in the water phase is 0.26% glucose, 3.17% xylose, 0.13% galactose, and 0.48% arabinose.
- the extraction rate of xylose reached 90.17%.
- the water phase is processed into pure xylose through the existing xylose production technology;
- the solid content of the organic phase is 7.06%, which can be directly reused in the next hydrolysis process of the miscellaneous sugar liquid.
- the solid content of the organic phase reaches 50%, the lignin solid is obtained by vacuum concentration and drying, and the lignin recovery rate can reach 90% the above.
- the pH of the mixed sugar liquid is 3.10, the solid content is 8.90%, and the distilled aldehyde is 1.81%;
- miscellaneous sugar liquid The main components of the miscellaneous sugar liquid are: 1.20% xylose, 0.30% glucose, 0.13% galactose, 0.35% arabinose, 1.08% xylan, and 5.16% lignin.
- the tetrasaccharide content in the water phase is 0.31% glucose, 2.65% xylose, 0.14% galactose, and 0.39% arabinose.
- the extraction rate of xylose reaches 87.84%; the aqueous phase is processed into pure xylose through the existing xylose technology;
- the solid content of the organic phase is 10.71%, which can be reused directly in the next hydrolysis process of the miscellaneous sugar liquid.
- the solid content of the organic phase reaches 50%, the lignin solid is obtained by vacuum concentration and drying, and the lignin recovery rate can reach 90%. the above.
- the pH of the mixed sugar liquid is 3.10, the solid content is 8.90%, and the distilled aldehyde is 1.81%;
- the main components of the mixed sugar liquid are: xylose 1.30%, glucose 0.25%, galactose 0.13%, arabinose 0.29%, xylan 1.08%, and lignin 5.16%.
- the tetrasaccharide content in the water phase is 0.23% glucose, 2.87% xylose, 0.11% galactose, and 0.29% arabinose.
- the extraction rate of xylose reached 90.60%.
- the water phase is processed into pure xylose through the existing xylose production technology;
- the solid content of the organic phase is 7.23%, which is directly reused in the next hydrolysis process of the miscellaneous sugar liquid.
- the solid content of the organic phase reaches 50%, the lignin solid is obtained by vacuum concentration and drying.
- the pH of the mixed sugar liquid is 3.10, the solid content is 8.90%, and the distilled aldehyde is 1.81%;
- miscellaneous sugar liquid The main components of the miscellaneous sugar liquid are: xylose 1.30%, glucose 0.30%, galactose 0.15%, arabinose 0.30%, xylan 1.08%, and lignin 5.16%.
- the tetrasaccharide content in the water phase is 0.29% glucose, 1.07% xylose, 0.16% galactose, and 0.31% arabinose.
- the extraction rate of xylose was 39.57%.
- the solid content of the organic phase is 7.24%, which can be reused directly in the next hydrolysis process of the miscellaneous sugar liquid.
- the solid content of the organic phase reaches 50%, the lignin solid is obtained by vacuum concentration and drying, and the lignin recovery rate can reach 90% the above.
- the pH of the mixed sugar liquid is 3.10, the solid content is 8.90%, and the distilled aldehyde is 1.81%;
- miscellaneous sugar liquid The main components of the miscellaneous sugar liquid are: xylose 1.30%, glucose 0.19%, galactose 0.13%, arabinose 0.45%; xylan 1.08%; lignin 5.16%.
- the tetrasaccharide content in the water phase is 0.21% glucose, 1.75% xylose, 0.13% galactose, and 0.49% arabinose.
- the extraction rate of xylose reached 64.22%.
- the solid content of the organic phase is 0.99%, and the amount of lignin dissolved in the organic solvent is very small, accounting for about 14%. More than 80% of the amount is scaled on the wall of the four-neck bottle, and the container scales seriously. There is also a small amount of lignin that is miscible in the water phase, which not only affects the extraction rate of xylose, but also scales during the subsequent processing and production of xylose.
- the pH of the mixed sugar liquid is 3.10, the solid content is 8.90%, and the distilled aldehyde is 1.81%;
- the main components of the mixed sugar liquid are: xylose 1.30%, glucose 0.30%, galactose 0.13%, arabinose 0.30%, xylan 1.08%, and lignin 5.16%.
- the tetrasaccharide content in the water phase is 0.33% glucose, 1.97% xylose, 0.15% galactose, and 0.30% arabinose.
- the extraction rate of xylose reached 65.08%.
- the solid content of the organic phase is 1.18%, and the amount of lignin dissolved in the organic solvent is very small, accounting for about 15%. 80% of the amount is scaled on the wall of the four-neck bottle, and the container scales seriously. There is also a small amount of lignin that is miscible in the water phase, which not only affects the extraction rate of xylose, but also scales during subsequent processing and production of xylose.
- test results such as the yield of lignin separated in Examples 1-5 and Comparative Examples 1-4 are as follows.
- the extraction rate of xylose in Examples 1-5 can reach about 90%, and the yield of lignin is above 90%, both of which are significantly higher than the comparative example and also significantly higher than the prior art, such as CN103061179B , CN103074790B, CN103898785B, CN103898786B.
- the ash content is less than 2%, the purity is high, the preparation method is simple, and there is no need for multiple separations.
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Abstract
Description
Claims (9)
- 一种从杂糖液中分离木糖与木质素的方法,其特征在于,所述方法包括以下步骤:水解步骤:将杂糖液与溶剂投入反应釜中,加入酸催化剂,进行水解反应;分离步骤:水解反应结束后,对溶剂相和水相进行分离,经分离的水相经过色谱、离子交换及结晶的步骤从而获得木糖纯品;经分离的溶剂相部分继续循环回用至下一批次的水解步骤,当溶剂内固形物含量达到50%以上后,再通过真空蒸发设备以回收溶剂,经回收的溶剂循环回所述水解步骤作为溶剂使用,经真空蒸发并回收溶剂后获得木质素纯品。
- 根据权利要求1所述的方法,其特征在于,所述杂糖液包含占全部杂糖液20-40%的糖组分,其中,糖组分中单糖占全部糖组分的5-15%,多糖占全部糖组分的85-95%;除所述单糖和多糖之外,杂糖液还包含占全部杂糖液60-70%的木质素及溶解盐类组分。
- 根据权利要求1-2中任一项所述的方法,其特征在于,在水解步骤中使用的溶剂包含:MIBK、正丁醇、甲苯及异佛尔酮中的一种或两种以上的组合。
- 根据权利要求1-3中任一项所述的方法,其特征在于,在水解步骤中,所述杂糖液与所述溶剂的质量比为1:1-4:1。
- 根据权利要求1-4中任一项所述的方法,其特征在于,在水解步骤中,所述酸催化剂包含硫酸、盐酸、硝酸及磷酸的一种或两种以上的组合。
- 根据权利要求1-5中任一项所述的方法,其特征在于,在水解步骤中,相对于杂糖液的总质量,所述酸催化剂的含量为杂糖液质量的3-6质量%。
- 根据权利要求1-6中任一项所述的方法,其特征在于,在水解步骤中,水解反应为在90-120℃水解反应1-5h。
- 根据权利要求1-7中任一项所述的方法,其特征在于,在分离步骤 中,经分离的溶剂相部分循环回用至下一批次的水解步骤,溶剂循环使用的数次高达8次;当溶剂内固形物含量达到50%以上,再通过真空蒸发设备以回收溶剂及分离木质素。
- 根据权利要求1-8中任一项所述的方法,其特征在于,在分离步骤中,溶剂回收率达99.5%以上。
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BR112022003322A BR112022003322A2 (pt) | 2019-08-22 | 2020-08-21 | Método para separar xilose e lignina de líquido de açúcar variado |
AU2020334939A AU2020334939B2 (en) | 2019-08-22 | 2020-08-21 | Method for separating xylose and lignin from mixed sugar solution |
US17/637,084 US20220290264A1 (en) | 2019-08-22 | 2020-08-21 | Method for separating xylose and lignin from miscellaneous sugar liquid |
EP20854786.9A EP4019649A4 (en) | 2019-08-22 | 2020-08-21 | PROCESS FOR SEPARATING XYLOSE AND LIGNIN FROM A MIXED SUGAR SOLUTION |
CA3151877A CA3151877A1 (en) | 2019-08-22 | 2020-08-21 | Method for separating xylose and lignin from miscellaneous sugar liquid |
IL290775A IL290775A (en) | 2019-08-22 | 2022-02-21 | A process for separating xylose and lignin from a mixture of sugars |
ZA2022/03343A ZA202203343B (en) | 2019-08-22 | 2022-03-22 | Method for separating xylose and lignin from mixed sugar solution |
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IL290775A (en) | 2022-04-01 |
CN112410475A (zh) | 2021-02-26 |
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ZA202203343B (en) | 2022-09-28 |
EP4019649A4 (en) | 2022-10-12 |
EP4019649A1 (en) | 2022-06-29 |
AU2020334939A1 (en) | 2022-03-24 |
BR112022003322A2 (pt) | 2022-05-24 |
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