CN106702800A - Method for removing straw lignin and hemicellulose by using protic ionic liquid - Google Patents
Method for removing straw lignin and hemicellulose by using protic ionic liquid Download PDFInfo
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- CN106702800A CN106702800A CN201611261727.0A CN201611261727A CN106702800A CN 106702800 A CN106702800 A CN 106702800A CN 201611261727 A CN201611261727 A CN 201611261727A CN 106702800 A CN106702800 A CN 106702800A
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C3/00—Pulping cellulose-containing materials
- D21C3/003—Pulping cellulose-containing materials with organic compounds
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Abstract
The invention discloses a method for removing straw lignin and hemicellulose by using single ionic liquid and by a one-step method. The ionic liquid in the method is polyhydroxyl protic ammonium salt ionic liquid. The method is characterized in that three components of a lignocellulose material are dissolved and separated under the conditions that the temperature is 80 to 160 DEG C, the time is 0.25 to 24 hours and the mass percentage of the lignocellulose material is 5 to 10 percent, so that the lignin content and the hemicellulose content can be reduced by 50 to 95 percent simultaneously. The ionic liquid is characterized in that the used synthetic raw materials are cheap and simple in synthesis method, and have biodegradability; the lignin and the hemicellulose are dissolved and removed from the biomass component simultaneously by the ionic liquid one-step method, a cellulose I type material with the purity higher than 70 percent is obtained, and the crystal structure of the cellulose in the raw material biomass component is maintained. By the method, the problems that the conventional ionic liquid is expensive and has poor separation effect are solved, possibility is provided for industrialization of pretreating biomass by the ionic liquid, and the ionic liquid belongs to a novel biomass pretreatment solvent.
Description
Technical field
The present invention relates in a kind of polyhydroxy proton type ammonium salt class ion liquid dissolving separation lignocellulosic stalk
Cellulose and lignin, hemicellulose, obtain the section bar material of high purity cellulose I, belong to biomass field.
Background technology
With the increasingly exhaustion of earth fossil resource, energy and environment problem is needed badly in having become human industryization development
The important problem of solution, develops and using green renewable resource, the efficient utilization for realizing resource is to solve current chemical industry
The effective way of slower development.Biomass resource as reserves on the earth are big, widespread green regenerative energy sources, in recent years
Research and probe in receive the extensive concern of people.In addition to forest cover, agricultural crop straw and various annual plants
Thing stalk is also played an important role in the material of nature with energy circulation.As the main composition portion of biomass resource
Point, cellulose, hemicellulose and lignin can be extracted and be used by the technique of biorefinery.Cellulose
(35-55%) and hemicellulose (20-35%) can be decomposed into glucose and xylose, and the method conversion for passing through biological and chemical
The chemicals such as multi-medicament intermediate and alcohol fuel, gasoline and glycol is produced, and lignin (15-30%) can also lead to
Cross the aromatic compound that distinct methods are catalytically conveted to gasoline and other high added values.Maize straw, cotton stalk, reed rod and wood
Consider these inexpensive agricultural wastes to be worth doing, the lignocellulosic of itself is the renewable resource of preciousness in nature.
Separated and dissolved pretreatment is carried out by lignocellulosic labyrinth, biomass components cellulose and half fibre is realized
Dimension element, lignin efficiently separate be biomass resource utilization committed step, wherein, for the separation and Extraction and profit of cellulose
With particularly important.Solvent used by conventional pretreatment technical process is generally acid, aqueous slkali or organic solvent, but these solvents
The environmental pollution of system generally existing is serious, can not recycle, strict to equipment requirement with high cost the problems such as.
Ionic liquid receives the extensive concern of people as reaction medium and solvent in research in recent years.Ion
Liquid has heat endurance good, hardly possible volatilization, the advantages of recyclable, has been widely used for organic synthesis, and industry is urged
The field such as change and extract and separate.Ionic liquid at room temperature can form stronger ionic liquid hydrogen bond action with biomass components, this
For its component separated and dissolved for being applied to biomass provides new approaches.Conventional single ionic liquid separated and dissolved wood fibre
Plain component has two kinds of thinkings, and a kind of thinking is with the fibre in the dissolving preferable ion liquid dissolving lignocellulosic of cellulose ability
Dimension element, then regeneration obtains the cellulose Ⅱ section bar material of amorphous state, to promote the further Transformation Application of cellulose, patent
US2010/0163018 A1, WO2016/116126 A2, US2016/0002358 A1 disclose pre- with different ionic liquid
Treatment is separated and using the method for lignocellulosic.Another thinking is to be removed using to the preferable ionic liquid of lignin dissolution
Lignin in biomass components, obtains fiber-rich cellulosic material, and the A of patent CN 103031762 have then used this method.
The cation that ionic liquid is used for biomass components dissolving mainly includes N- methylimidazoles, ammonium salt class and microcosmic salt
Class, anion is mainly X-(halogen), CH3COO-、CH3SO4 -、(CH3)2O2PO2 -And HCO2 -Deng, but most of single ionics
Liquid can not realize efficiently separating for cellulose and hemicellulose in lignocellulosic component, and synthesis step is more, cost
Height, by dissolving and regenerates the cellulosic material for obtaining and can destroy the crystalline structure of cellulose in raw material, in follow-up application
In be restricted, meanwhile, dimethyl sulfoxide (DMSO) organic solvent is used in separated and dissolved, environmental pollution is serious, does not meet sustainable development
Exhibition and the theory of green processes engineering.
The content of the invention
The invention provides a kind of polyhydroxy proton type ammonium salt class ionic liquid as separated and dissolved lignocellulosic component
Solvent, one-step method can be such that lignin and hemicellulose in biomass material removes simultaneously, obtain I fiber type of higher degree
Cellulosic material.Ionic liquid general structure is as follows：
Method for synthesizing ionic liquid used by the present invention is as follows：
Under 273.15K temperature conditionss, appropriate Loprazolam is titrated into the methyl alcohol that funnel is slowly dropped into hydramine by constant pressure
In solution, after completion of dropping, room temperature reaction 48h is warming up to, stops reaction, rotary evaporation removes methanol solvate, ether is used respectively
Washed three times with ethyl acetate, the ionic liquid vacuum drying that will finally synthesize.
Separated and dissolved experimental procedure to lignocellulosic is as follows：
Biomass starting material stalk is first washed with neutral detergent, be dry, pulverize and sieved, filter out certain particle size
The lignocellulosic material of (≤0.125mm).
The lignocellulosic material and ionic liquid of mass fraction 5%-10% are added heating stirring in flask simultaneously.
Experimental temperature is 80-160 DEG C, and the reaction time is 0.25-24h, wooden in polarized light microscopy Microscopic observation every 0.5h
Cellulosic component dissolves situation.After reaction terminates, to the dilution centrifugation of 10mL deionized waters is added in system, by consolidating that centrifugation is obtained
Body is washed 3-6 times, is dried to obtain high purity cellulose material.
Advantage of the present invention
The ionic liquid synthesis of 1 invention is simple, low in raw material price, and it is expensive to overcome conventional ionic liquid, synthesis
Method is cumbersome, the shortcomings of high cost.
The ionic liquid of 2 inventions shows excellent separated and dissolved ability to lignocellulosic, can simultaneously dissolve wooden
Lignin and hemicellulose in cellulosic component, obtain the cellulose Ⅰ section bar material that purity is 70-95%, maintain stalk former
The crystalline structure of cellulose in material.
The 3 pairs of hydroxy kind ion liquid dissolving separating effects preferably, meanwhile, cellulose is not dissolved in experiment, and product is easy to point
From energy consumption is low, for the industrialization of ionic liquid separating biomass components provides possibility.
Ionic liquid and water have only been used in separated and dissolved experiment in 4 inventions, eliminate conventional ionic liquid separated and dissolved stalk
The dimethyl sulfoxide (DMSO) diluent that different component is used, more environmental protection meets the theory of green processes engineering.
Brief description of the drawings
Accompanying drawing is specific embodiment 1, embodiment 2, embodiment 3, embodiment 4, embodiment 5, embodiment 6, the fibre of embodiment 7
The XRD comparison diagrams of dimension cellulosic material and stalk and cotton haulm raw material.
Fig. 1 specific embodiments 1, embodiment 2, embodiment 3, embodiment 4, embodiment 5, embodiment 6, embodiment 8, embodiment
9, embodiment 10, the cellulosic material and corn stalk raw material XRD comparison diagrams of embodiment 11.
The cellulosic material and cotton stalk raw material XRD comparison diagrams of Fig. 2 specific embodiments 7.
Specific embodiment
The present invention is further illustrated with reference to embodiment, but, it is right that specific implementation example is not constituted in any way
The limitation of the scope of the invention.
Embodiment 1
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) maize straw powder, 120 DEG C of bars
Magnetic agitation 24h under part, divides to the dilution of 10mL deionized waters, centrifugation is added in reacted ionic liquid and stalk mixture
From.The undissolved product of gained is cleaned using clear water, dried, weighed, calculate the solubility of the ionic liquid, and product is carried out
Lignocellulosic component analysis.Composition analysis result shows that content of lignin drops to from the 15.28% of raw material in product
1.99%, hemicellulose level drops to 4.04% from 31.21%, and content of cellulose brings up to 91.81% from 50.53%.
Embodiment 2
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) maize straw powder, 120 DEG C of bars
Magnetic agitation 0.25h under part, divides to the dilution of 10mL deionized waters, centrifugation is added in reacted ionic liquid and stalk mixture
From.The undissolved product of gained is cleaned using clear water, dried, weighed, calculate the solubility of the ionic liquid, and product is carried out
Lignocellulosic component analysis.Composition analysis result shows that content of lignin drops to from the 15.28% of raw material in product
5.30%, hemicellulose level drops to 10.08% from 31.21%, and content of cellulose brings up to 76.53% from 50.53%.
Embodiment 3
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) maize straw powder, 80 DEG C of bars
Magnetic agitation 6h under part, to the dilution of addition 10mL deionized waters, centrifugation in reacted ionic liquid and stalk mixture.
The undissolved product of gained is cleaned using clear water, dried, weighed, calculate the solubility of the ionic liquid, and product is carried out into wood
Matter cellulosic component is analyzed.Composition analysis result shows that content of lignin drops to from the 15.28% of raw material in product
8.14%, hemicellulose level drops to 12.60% from 31.21%, and content of cellulose brings up to 70.00% from 50.53%.
Embodiment 4
To by dry 10g proton type ionic liquids solvent triethanolamine methane sulfonates ([(HOCH2CH2)3NH]+
CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) maize straw powder, magnetic force under the conditions of 160 DEG C
Stirring 6h, to the dilution of addition 10mL deionized waters, centrifugation in reacted ionic liquid and stalk mixture.By gained not
Dissolved product is cleaned using clear water, dries, weighs, and calculates the solubility of the ionic liquid, and product is carried out into lignocellulosic
Component analysis.Composition analysis result shows that content of lignin drops to 5.45%, half fiber from the 15.28% of raw material in product
Cellulose content drops to 5.44% from 31.21%, and content of cellulose brings up to 82.44% from 50.53%.
Embodiment 5
To by dry 10g proton type ionic liquids solvent N, N- dimethylethanolamine methane sulfonates
([(HOCH2CH2)NH(CH3)2]+CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) maize straw
Powder, magnetic agitation 6h under the conditions of 140 DEG C, to being added in reacted ionic liquid and stalk mixture, 10mL deionized waters are dilute
Release, centrifugation.The undissolved product of gained is cleaned using clear water, dried, weighed, calculate the solubility of the ionic liquid, and
Product is carried out into lignocellulosic component analysis.Composition analysis result shows, in product content of lignin from raw material 15.28%
Drop to 12.51%, hemicellulose level drops to 9.56% from 31.21%, and content of cellulose brings up to from 50.53%
78.01%.
Embodiment 6
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in add 1.0g by washing, dry, sieving (≤0.125mm) maize straw powder, 130 DEG C of bars
Magnetic agitation 6h under part, to the dilution of addition 10mL deionized waters, centrifugation in reacted ionic liquid and stalk mixture.
The undissolved product of gained is cleaned using clear water, dried, weighed, calculate the solubility of the ionic liquid, and product is carried out into wood
Matter cellulosic component is analyzed.Composition analysis result shows that content of lignin drops to from the 15.28% of raw material in product
8.60%, hemicellulose level drops to 8.05% from 31.21%, and content of cellulose brings up to 76.10% from 50.53%.
Embodiment 7
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) cotton stalk powder end, under the conditions of 130 DEG C
Magnetic agitation 6h, to the dilution of addition 10mL deionized waters, centrifugation in reacted ionic liquid and stalk mixture.By institute
Obtain undissolved product to be cleaned using clear water, dry, weigh, calculate the solubility of the ionic liquid, and product is carried out into wooden fibre
The plain component analysis of dimension.Composition analysis result shows that content of lignin drops to 16.60% from the 23.59% of raw material in product, half
Content of cellulose drops to 2.05% from 18.45%, and content of cellulose brings up to 75.10% from 43.98%.
Embodiment 8
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)3NH]+CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) maize straw powder, under the conditions of 150 DEG C
Magnetic agitation 6h, to the dilution of addition 10mL deionized waters, centrifugation in reacted ionic liquid and stalk mixture.By institute
Obtain undissolved product to be cleaned using clear water, dry, weigh, calculate the solubility of the ionic liquid, and product is carried out into wooden fibre
The plain component analysis of dimension.Composition analysis result shows that content of lignin drops to 7.22% from the 15.28% of raw material in product, half
Content of cellulose drops to 9.10% from 31.21%, and content of cellulose brings up to 83.32% from 50.53%.
Embodiment 9
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) maize straw powder, 120 DEG C of bars
Magnetic agitation 0.75h under part, divides to the dilution of 10mL deionized waters, centrifugation is added in reacted ionic liquid and stalk mixture
From.The undissolved product of gained is cleaned using clear water, dried, weighed, calculate the solubility of the ionic liquid, and product is carried out
Lignocellulosic component analysis.Composition analysis result shows that content of lignin drops to from the 15.28% of raw material in product
4.16%, hemicellulose level drops to 8.62% from 31.21%, and content of cellulose brings up to 82.05% from 50.53%.
Embodiment 10
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in add 0.5g by washing, dry, sieving (≤0.125mm) maize straw powder, 120 DEG C of bars
Magnetic agitation 1h under part, to the dilution of addition 10mL deionized waters, centrifugation in reacted ionic liquid and stalk mixture.
The undissolved product of gained is cleaned using clear water, dried, weighed, calculate the solubility of the ionic liquid, and product is carried out into wood
Matter cellulosic component is analyzed.Composition analysis result shows that content of lignin drops to from the 15.28% of raw material in product
4.03%, hemicellulose level drops to 8.51% from 31.21%, and content of cellulose brings up to 82.25% from 50.53%.
Embodiment 11
To by dry 10g proton type ionic liquids Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in add 0.8g by washing, dry, sieving (≤0.125mm) maize straw powder, 130 DEG C of bars
Magnetic agitation 6h under part, to the dilution of addition 10mL deionized waters, centrifugation in reacted ionic liquid and stalk mixture.
The undissolved product of gained is cleaned using clear water, dried, weighed, calculate the solubility of the ionic liquid, and product is carried out into wood
Matter cellulosic component is analyzed.Composition analysis result shows that content of lignin drops to from the 15.28% of raw material in product
7.31%, hemicellulose level drops to 7.66% from 31.21%, and content of cellulose brings up to 75.10% from 50.53%.
Claims (7)
1. a kind of method that lignocellulosic component is separated with polyhydroxy proton type ammonium salt class ionic liquid pretreatment, its feature exists
In with polyhydroxy proton type ammonium salt class ionic liquid as solvent, under uniform temperature and time conditions, by certain mass fraction
Lignocellulosic material adds heating stirring in reaction bulb together with ionic liquid, after reaction terminates, to added in system go from
Sub- water dilution cooling, the not molten thing of centrifugation solid, and solid is washed, obtain purity I fiber type material higher after drying
Material.
2. method according to claim 1, the structure of polyhydroxy proton type ammonium salt class ionic liquid is as follows：
R1=CH2CH2OH, CH2CH2CH2OH, CH2CH2CH2CH2OH
X-=CH3SO3-, CH3COO-, CF3SO3-,。
3. method according to claim 1, it is characterised in that it is corn stalk that pretreatment separates lignocellulosic material used
Stalk, cotton stalk, green bristlegrass, reed rod, agropyron, wood chip.
4. method according to claim 1, dissolution experiment temperature is 80-160 DEG C.
5. method according to claim 1, the separated and dissolved experiment reaction time is 0.25-24h.
6. method according to claim 1, lignocellulosic material quality point in separated and dissolved experiment ion liquid solvent
Number is 5%-10%.
7. method according to claim 1, the product of dissolution experiment is high-purity I-type cellulosic material, maintains raw material
The crystalline structure of middle cellulose, wherein, content of cellulose reaches 70-95%, and lignin dissolution clearance and hemicellulose dissolve
Clearance is 40-95%.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107960679A (en) * | 2017-12-18 | 2018-04-27 | 河南卷烟工业烟草薄片有限公司 | A kind of papermaking-method reconstituted tobaccos wood-fibred treatment process |
| CN109704902A (en) * | 2018-12-28 | 2019-05-03 | 中国科学院过程工程研究所 | Ionic liquid-catalyzed method of deoxidation during a kind of lignin derivative hydrogenation deoxidation |
| CN111154817A (en) * | 2020-02-19 | 2020-05-15 | 中国科学院过程工程研究所 | Method for efficiently separating lignocellulose and carrying out enzymolysis by using ionic liquid-high-boiling-point alcohol composite system |
| CN113774701A (en) * | 2021-09-16 | 2021-12-10 | 江南大学 | Method for removing lignin in straw by using glycine and acetic acid |
| CN113882179A (en) * | 2021-09-29 | 2022-01-04 | 江南大学 | Method for removing lignin in straw by using nitric acid 1-hydroxy-3-mercaptopropane-2-amine |
| CN114846204A (en) * | 2019-12-23 | 2022-08-02 | 芬宝公司 | Dispersion of cellulose fibres and method for producing same |
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| CN113774701A (en) * | 2021-09-16 | 2021-12-10 | 江南大学 | Method for removing lignin in straw by using glycine and acetic acid |
| CN113882179A (en) * | 2021-09-29 | 2022-01-04 | 江南大学 | Method for removing lignin in straw by using nitric acid 1-hydroxy-3-mercaptopropane-2-amine |
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