CN103409566A - Method for degrading lignocellulose to generate reducing sugar - Google Patents
Method for degrading lignocellulose to generate reducing sugar Download PDFInfo
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- CN103409566A CN103409566A CN2013103744606A CN201310374460A CN103409566A CN 103409566 A CN103409566 A CN 103409566A CN 2013103744606 A CN2013103744606 A CN 2013103744606A CN 201310374460 A CN201310374460 A CN 201310374460A CN 103409566 A CN103409566 A CN 103409566A
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Abstract
The invention discloses a method for degrading lignocellulose to generate reducing sugar, and in particular relates to the method for degrading lignocellulose to generate reducing sugar by using H2O2 as a catalyst and using metal ion as a catalyst promoter. The method comprises the following steps: adopting an ionic liquid as a solvent, commercially available hydrogen peroxide with the mass fraction of 30% as a catalyst and metal ion as a catalyst promoter; and dissolving and degrading lignocellulose materials to generate water-soluble reducing sugar, wherein the ionic liquid can be recycled. The method for degrading lignocellulose to generate reducing sugar has the characteristics of being simple and convenient to operate, gentle in condition, environment-friendly, low in cost, less in byproducts, high in reducing sugar yield and the like. The method for degrading lignocellulose to generate reducing sugar can be used for treating various lignocellulose materials; and when the lignocellulose materials are treated by adopting the method, the conversion rate of the lignocellulose materials is bigger than 80%, the reducing sugar yield is bigger than 65%, and the recovery rate of the ionic liquid is bigger than 95%.
Description
One, technical field
The invention belongs to ligocellulose degradation and utilize and the Industrial Catalysis field, be specifically related to a kind of method that lignocellulose degradation generates reducing sugar.
Two, background technology
Lignocellulose is renewable resources abundant, the most cheap on the earth.Have data to show, in the annual plant materials in the whole world, the growing amount of Mierocrystalline cellulose, hemicellulose is up to 8.5 * 10
10T.China is a large agricultural country, the lignocellulose resource is extremely abundant, development be take lignocellulose and is main biomass resource transformation technology, is conducive to improve that current resource is nervous, the situation of environmental degradation, and human society is realized to Sustainable development has important economy and social effect.Lignocellulosic material is comprised of Mierocrystalline cellulose, hemicellulose and xylogen three parts.Hemicellulose is combined between Mierocrystalline cellulose and xylogen as the molecule tamanori, and the reticulated structure that xylogen has, and surrounds and adds set Mierocrystalline cellulose and hemicellulose as support frame.Mierocrystalline cellulose is by β-1 by glucose unit; the high molecular polymer that the link of 4-glycosidic link forms; due to himself aggregated structure characteristic; particularly in natural biomass xylogen etc. to cellulosic provide protection; cause Mierocrystalline cellulose to be insoluble to general organic solvent and water; and enzyme is low to its accessibility, be difficult to it directly is degraded to reducing sugar, therefore be necessary to develop a kind of method of novel, easy and simple to handle, eco-friendly direct lignocellulose degradation.
Existing process the method that lignocellulosic material is converted into reducing sugar: as on December 31st, 2008 disclosed publication number be the method for effectively hydrolyzing lignocellulosic raw material " a kind of in ionic liquid " patent of CN101333777A, disclosed method is: the ionic liquid of take is solvent, the water of take is reactant, the acid of take is catalyzer, lignocellulose reacted 2 minutes～34 hours in 80 ℃～100 ℃ under normal pressure, after reaction finishes, with cold water cancellation reaction, with the alkali neutralization, obtain ligno-cellulose hydrolysate.The method be take acid and is catalyzer, having reacted rear neutralizes with alkali, its main drawback is: the acid that the method is used is the concentrated acids such as the vitriol oil, concentrated hydrochloric acid, concentrated nitric acid, strong phosphoric acid, and the usage quantity of concentrated acid is 2%～100% of lignocellulose raw material quality, the usage quantity of concentrated acid is large, need the sodium hydroxide neutralization with a large amount of 0.5mol/L, the erosion resistance requirement to equipment in suitability for industrialized production is high, easily causes environmental pollution.
It as publication No., is the patent " a kind of ionic liquid pre-treatment Mierocrystalline cellulose makes it be converted into the processing method of water-soluble sugar fully " of CN102796143/A, disclosed method is: with N-Methylimidazole and phosphoric acid ester Reofos ionic liquid, and under 140～160 ℃, dissolve, transform Mierocrystalline cellulose, by cellulose conversion, be water-soluble sugar; And the water-soluble sugar that the method that adopts the anti-solvent of ethanol obtains experiment is realized the recycling of ionic liquid from ionic liquid, separating.The main drawback of the method is: service temperature is too high, and energy consumption is larger, and production cost is high, and side reaction at high temperature easily occurs Mierocrystalline cellulose, and by product is many, and simultaneously, water-soluble sugar is at high temperature degraded easily, and sugar yield is reduced.
And for example, publication No. is the patent " a kind of preprocessing lignocellulose feedstock conversion is the method for reducing sugar " of CN102758028A, disclosed method is: adopt liquid-solid ratio 5～50, lignocellulose was processed 1～10 hour in the mixing solutions of the hydrogen peroxide of massfraction 0～5% sodium hydroxide and massfraction 0～5%, after processing, the gained solid residue washes oven dry with water.Then in temperature, be 30～150 ℃, h 2 so 4 concentration 0～10%, the solid residue that under the condition of liquid-solid ratio 5～50, acidolysis is processed 10～120 minutes, regulate pH value to 7, then dries.Its main drawback is: the alkaline hydrogen peroxide of preprocessing lignocellulose raw material is not easy to be recycled, makes production cost too high, uses the dilute sulphuric acid catalyzing cellulose hydrolysis, and sour consumption is large, high to the erosion resistance requirement of equipment, easily causes environmental pollution.
Three, summary of the invention
Main purpose of the present invention is to process for pre existing the weak point that lignocellulosic material is converted into the reducing sugar technology, proposes a kind ofly to take ionic liquid and be solvent, with H
2O
2For catalyzer, the metal ion of take is promotor, and oxidative degradation Mierocrystalline cellulose and hemicellulose prepare the method for reducing sugar under mild conditions.Present method is easy and simple to handle, mild condition, environmental friendliness, cost is low, by product is few, reducing sugar yield is high.
For achieving the above object, the technical solution used in the present invention is:
(1) lignocellulosic material is crushed to 20～60 orders, dry 5～10h under 50～60 ℃;
(2) ionic liquid is joined in round-bottomed flask, the mass ratio of lignocellulosic material and ionic liquid is 1kg: 10～50kg, and oil bath is heated to ionic liquid and becomes clarified liq;
(3) to adding rapidly commercially available massfraction in step (2), be 30% hydrogen peroxide and a certain amount of metal ion promotor, wherein H
2O
2The mass ratio with lignocellulosic material be 1kg: 1～50kg, the add-on of metal ion is 0.1～10% of lignocellulosic material quality, oil bath is heated to mixing solutions and becomes homogeneous liquid;
(4) in the magnetic agitation process, join the dry lignocellulosic material of crossing of step (1) in the mixed solution of step (3), under normal pressure, to lignocellulosic material, fully dissolve, transform, stopped heating in 80～120 ℃ of magnetic agitation reaction 1～30h;
(5) in the flask that step (4) has been reacted, add dehydrated alcohol, Virahol etc. to dissolve each other with ionic liquid, but low boiling point organic solvent that can not dissolved water dissolubility reducing sugar is as anti-solvent, by the mixture centrifugal 5～10min under 8000～12000r/min obtained, dry, filtration, obtain the reducing sugar solid of unconverted lignocellulose and generation, and the mixed solution that contains ionic liquid;
(6) solid mixture deionized water dissolving step (5) obtained, obtain the reducing sugar aqueous solution and unconverted cellulose solids, calculates the productive rate of reducing sugar;
(7) ionic liquid mixing solutions step (5) obtained is removed anti-solvent with Rotary Evaporators under 80～100 ℃, obtain ionic liquid, is reused for dissolving and the degradation process of Mierocrystalline cellulose etc.
(8) unconverted lignocellulose step (6) obtained is dry 3～5h under 102～110 ℃, weighs, and calculates the transformation efficiency of lignocellulose.
Ionic liquid of the present invention is for Mierocrystalline cellulose and hemicellulose being had to the ionic liquid 1 of better dissolving power, 3-dialkylimidazolium or Fixanol, and its substituting group chain length is C
1-C
4Alkyl chain or allyl group chain, the negatively charged ion of salt is chlorine, bromine or tetrafluoroborate, is specially: 1-butyl-3-Methylimidazole chlorine, 1-butyl-3-Methylimidazole bromine, 1-butyl-3-methyl imidazolium tetrafluoroborate, 1-allyl group-3-Methylimidazole chlorine, 1-allyl group-3-Methylimidazole bromine, 1-allyl group-3-methyl a tetrafluoro borate.
Lignocellulosic material of the present invention is Microcrystalline Cellulose, maize straw, rice straw, pine, bamboo pole etc. or their mixture.
Metal ion promotor of the present invention is commercially available metal halogen, is specially: FeCl
2, FeCl
3, CuCl
2, MgCl
2, ZnCl
2, CrCl
3, CaCl
2, NiCl
2Deng.
The present invention produces following technique effect:
1. can process multiple lignocellulosic material, the cellulose conversion rate is greater than 80%;
2. can obtain the reducing sugar of high density, reducing sugar yield is greater than 65%;
3. the ionic liquid rate of recovery is greater than 95%.
The present invention has the following advantages:
1. with traditional enzymatic hydrolysis process, compare, the present invention is without preprocessing process, and the catalyzer cost is low, and speed of reaction is fast;
2. with traditional acid and alkali hydrolysis technique, compare, operational condition gentleness of the present invention, technique is simple, to the erosion resistance of reactor require low, cost is low, environmental friendliness, the easy follow-up control of extent of reaction, by product are few;
3. with the cellulosic method of acid as catalyst catalytic hydrolysis in ionic liquid, compare, the present invention is without using acid, and less to equipment corrosion, subsequent disposal is simpler.
In a word, compared with prior art, the present invention has plurality of advantages: simple without pre-treatment, technique, be swift in response, to the erosion resistance of reactor require low, hydrolytic activity is high, extent of reaction is easily followed the tracks of and controls, for taking full advantage of of lignocellulose opened up new way, aspect obtaining bioenergy and bio-based chemical, raw material has huge application prospect take the lignocellulose reducing sugar.
Four, embodiment
The present invention is described in further detail by following examples, but the described technology contents of the present embodiment is illustrative, rather than determinate, should not limit to according to this protection scope of the present invention.
Embodiment 1:
5g1-butyl-3-methyl the ionic liquid of take is solvent, and the 120 μ L hydrogen peroxide of take are catalyzer, with Mg
2+For promotor, H wherein
2O
2With the mass ratio of Microcrystalline Cellulose be 1g: 10g, Mg
2+With the mass ratio of Microcrystalline Cellulose be 1g: 200g, by the 0.4g Microcrystalline Cellulose under normal pressure in 100 ℃ of magnetic agitation reaction 17 hours.Reaction is used water quench after finishing.By 3 times of reaction product of the absolute ethanol washing to the reaction product volume, the mixture after washing is centrifugal 5min under 10000r/min, filter, dry, weigh, the cellulose conversion rate is 100%, the productive rate of reducing sugar is 71.6%.The ionic liquid ethanolic soln that obtains is gone out to ethanol with Rotary Evaporators, obtain ionic liquid, the rate of recovery of ionic liquid is 96.5%.
Embodiment 2:
5g1-butyl-3-methyl the ionic liquid of take is solvent, and the 120 μ L hydrogen peroxide of take are catalyzer, with Mg
2+For promotor, H wherein
2O
2With the mass ratio of bamboo pole powder be 1g: 10g, Mg
2+With the mass ratio of bamboo pole powder be 1g: 50g, by 0.4g be crushed to 40 purpose bamboo pole powder under normal pressure in 100 ℃ of magnetic agitation reaction 22 hours.Reaction is used water quench after finishing.By 3 times of reaction product of the absolute ethanol washing to the reaction product volume, the mixture after washing is centrifugal 5min under 10000r/min, filter, dry, weigh, the cellulose conversion rate is 83.2%, the productive rate of reducing sugar is 67.4%.The ionic liquid ethanolic soln that obtains is gone out to ethanol with Rotary Evaporators, obtain ionic liquid, the rate of recovery of ionic liquid is 95.1%.
Embodiment 3:
5g1-butyl-3-methyl the ionic liquid of take is solvent, and the 120 μ L hydrogen peroxide of take are catalyzer, with Mg
2+For promotor, H wherein
2O
2With the mass ratio of maize straw be 1g: 10g, Mg
2+With the mass ratio of maize straw be 1g: 50g, by 0.4g be crushed to 40 purpose maize straws under normal pressure in 100 ℃ of magnetic agitation reaction 20 hours.Reaction is used water quench after finishing.By 3 times of reaction product of the absolute ethanol washing to the reaction product volume, the mixture after washing is centrifugal 5min under 10000r/min, filter, dry, weigh, the cellulose conversion rate is 81.5%, the productive rate of reducing sugar is 66.3%.The ionic liquid ethanolic soln that obtains is gone out to ethanol with Rotary Evaporators, obtain ionic liquid, the rate of recovery of ionic liquid is 95.4%.
Claims (6)
1. a lignocellulose degradation generates the method for reducing sugar, it is characterized in that concrete steps are as follows:
(1) lignocellulosic material is crushed to 20～60 orders, dry 5～10h under 50～60 ℃;
(2) ionic liquid is joined in round-bottomed flask, the mass ratio of lignocellulosic material and ionic liquid is 1kg: 10～50kg, and oil bath is heated to ionic liquid and becomes clarified liq;
(3) in step (2), add hydrogen peroxide and a certain amount of metal ion promotor, oil bath is heated to mixing solutions and becomes homogeneous liquid;
(4) the dry lignocellulosic material of crossing of step (1) is joined in the mixed solution of step (3) in the magnetic agitation process, in 80～120 ℃ of magnetic agitation, react 1～30h under normal pressure;
(5) in the flask that step (4) has been reacted, add anti-solvent, by the mixture centrifugal 5～10min under 8000～12000r/min obtained, dry, filter, obtain the reducing sugar solid of unconverted lignocellulose and generation, and the mixed solution that contains ionic liquid;
(6) solid mixture deionized water dissolving step (5) obtained, obtain the reducing sugar aqueous solution and unconverted cellulose solids, calculates the productive rate of reducing sugar;
(7) ionic liquid mixing solutions step (5) obtained is removed anti-solvent with Rotary Evaporators under 80～100 ℃, obtain ionic liquid.
(8) unconverted lignocellulose step (6) obtained is dry 3～5h under 102～110 ℃, weighs, and calculates the transformation efficiency of lignocellulose.
2. processing method according to claim 1, is characterized in that, described lignocellulosic material is Microcrystalline Cellulose, maize straw, rice straw, pine, bamboo pole and their mixture.
3. processing method according to claim 1, is characterized in that, described ionic liquid is for Mierocrystalline cellulose and hemicellulose being had to the ionic liquid 1 of better dissolving power, 3-dialkylimidazolium or Fixanol, and its substituting group chain length is C
1-C
4Alkyl chain or allyl group chain, the negatively charged ion of salt is chlorine, bromine or tetrafluoroborate, is specially: 1-butyl-3-Methylimidazole chlorine, 1-butyl-3-Methylimidazole bromine, 1-butyl-3-methyl imidazolium tetrafluoroborate, 1-allyl group-3-Methylimidazole chlorine, 1-allyl group-3-Methylimidazole bromine, 1-allyl group-3-methyl a tetrafluoro borate.
4. processing method according to claim 1, is characterized in that, the hydrogen peroxide added is that commercially available massfraction is 30% hydrogen peroxide, wherein H
2O
2The mass ratio with lignocellulosic material be 1kg: 1～50kg.
5. processing method according to claim 1, is characterized in that, the metal ion promotor is commercially available metal halogen, is specially: FeCl
2, FeCl
3, CuCl
2, MgCl
2, ZnCl
2, CrCl
3, CaCl
2, NiCl
2Deng, the add-on of metal ion is 0.1～10% of lignocellulosic material quality.
6. processing method according to claim 1, is characterized in that, described anti-solvent is dehydrated alcohol, Virahol etc., and the volume ratio of reaction product and anti-solvent is 1L: 1～5L.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740867A (en) * | 2014-01-02 | 2014-04-23 | 上海大学 | Method for preparing glucose by hydrolyzing straw celluloses |
| CN104450983A (en) * | 2014-12-24 | 2015-03-25 | 江南大学 | Method for producing reducing sugar by cellulose |
| CN104651542A (en) * | 2015-01-30 | 2015-05-27 | 华南理工大学 | Method for preparing reducing sugars by catalytic hydrolysis of duckweeds with heteropolyacid type ionic liquid |
| CN104862345A (en) * | 2015-06-18 | 2015-08-26 | 南京林业大学 | Detoxification method for wood fiber raw material pre-hydrolysis sugar liquid |
| CN104894298A (en) * | 2015-05-06 | 2015-09-09 | 重庆大学 | Method used for degrading lignocellulose with solid acid catalyst |
| CN104923295A (en) * | 2015-05-06 | 2015-09-23 | 重庆大学 | Preparation method for chitosan-based solid acid catalyst for biomass hydrolysis |
| CN105385722A (en) * | 2014-09-09 | 2016-03-09 | 中国科学院大连化学物理研究所 | Method for pre-processing lignocellulose biomass to increase sugar field of lignocellulose biomass |
| CN106084072A (en) * | 2016-06-27 | 2016-11-09 | 南京信息工程大学 | A kind of H2o2the method of degraded paper cellulose |
| CN106235385A (en) * | 2016-09-12 | 2016-12-21 | 甘肃烟草工业有限责任公司 | Tobacco stalk fibre microwave degradation prepares cigarette feed liquid method and application |
| CN109608657A (en) * | 2018-12-06 | 2019-04-12 | 齐鲁工业大学 | A kind of method of novel ion liquid lignin degrading |
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| WO2024113929A1 (en) * | 2022-11-30 | 2024-06-06 | 新乡化纤股份有限公司 | Ionic liquid method-based juncao regenerated cellulose fiber and preparation method therefor |
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| CN102071266A (en) * | 2010-12-03 | 2011-05-25 | 江南大学 | Application of ionic liquid to preparation of reducing sugar by cellulose hydrolysis |
| CN102796143A (en) * | 2011-05-26 | 2012-11-28 | 北京化工大学 | Process method for pretreating cellulose by using ionic liquid to completely convert cellulose into water-soluble sugar |
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| CN101597654A (en) * | 2009-06-23 | 2009-12-09 | 云天化集团有限责任公司 | A kind of method of utilizing protoplasm material to prepare reducing sugar |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740867A (en) * | 2014-01-02 | 2014-04-23 | 上海大学 | Method for preparing glucose by hydrolyzing straw celluloses |
| CN105385722A (en) * | 2014-09-09 | 2016-03-09 | 中国科学院大连化学物理研究所 | Method for pre-processing lignocellulose biomass to increase sugar field of lignocellulose biomass |
| CN105385722B (en) * | 2014-09-09 | 2019-07-12 | 中国科学院大连化学物理研究所 | A method of pretreatment wood fiber biomass improves its sugar yield |
| CN104450983A (en) * | 2014-12-24 | 2015-03-25 | 江南大学 | Method for producing reducing sugar by cellulose |
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| CN104651542A (en) * | 2015-01-30 | 2015-05-27 | 华南理工大学 | Method for preparing reducing sugars by catalytic hydrolysis of duckweeds with heteropolyacid type ionic liquid |
| CN104894298A (en) * | 2015-05-06 | 2015-09-09 | 重庆大学 | Method used for degrading lignocellulose with solid acid catalyst |
| CN104923295A (en) * | 2015-05-06 | 2015-09-23 | 重庆大学 | Preparation method for chitosan-based solid acid catalyst for biomass hydrolysis |
| CN104862345A (en) * | 2015-06-18 | 2015-08-26 | 南京林业大学 | Detoxification method for wood fiber raw material pre-hydrolysis sugar liquid |
| CN104862345B (en) * | 2015-06-18 | 2018-10-19 | 南京林业大学 | A kind of poison-removing method of lignocellulose raw material prehydrolysis liquid glucose |
| CN106084072A (en) * | 2016-06-27 | 2016-11-09 | 南京信息工程大学 | A kind of H2o2the method of degraded paper cellulose |
| CN106235385A (en) * | 2016-09-12 | 2016-12-21 | 甘肃烟草工业有限责任公司 | Tobacco stalk fibre microwave degradation prepares cigarette feed liquid method and application |
| CN106235385B (en) * | 2016-09-12 | 2017-09-29 | 甘肃烟草工业有限责任公司 | Tobacco stalk fibre microwave degradation prepares cigarette feed liquid method and application |
| TWI714817B (en) * | 2016-12-27 | 2021-01-01 | 中央研究院 | Method for producing glucose and small molecule polysaccharide |
| CN109608657A (en) * | 2018-12-06 | 2019-04-12 | 齐鲁工业大学 | A kind of method of novel ion liquid lignin degrading |
| WO2024113929A1 (en) * | 2022-11-30 | 2024-06-06 | 新乡化纤股份有限公司 | Ionic liquid method-based juncao regenerated cellulose fiber and preparation method therefor |
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Application publication date: 20131127 |