CN106702800B - A method of straw lignin and hemicellulose are removed with proton type ionic liquid - Google Patents
A method of straw lignin and hemicellulose are removed with proton type ionic liquid Download PDFInfo
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- CN106702800B CN106702800B CN201611261727.0A CN201611261727A CN106702800B CN 106702800 B CN106702800 B CN 106702800B CN 201611261727 A CN201611261727 A CN 201611261727A CN 106702800 B CN106702800 B CN 106702800B
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- ionic liquid
- hemicellulose
- lignin
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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
Abstract
The invention discloses a kind of methods of single ionic liquid one-step method removal straw lignin and hemicellulose, this method intermediate ion liquid is polyhydroxy proton type ammonium salt class ionic liquid, it is characterized by: at 80-160 DEG C of temperature, time 0.25-24h, three kinds of components in separated and dissolved ligno-cellulosic materials, can make wherein lignin and hemicellulose level simultaneously decline 50-95% under the conditions of ligno-cellulosic materials mass fraction 5%-10%.The ionic liquid is characterized in that synthesis material used is cheap, synthetic method is simple, with biodegradability, and ionic liquid one-step method dissolves the lignin and hemicellulose eliminated in biomass components simultaneously, the cellulose Ⅰ profile material that purity is higher than 70% has been obtained, the crystalline structure of cellulose in raw material biomass components is maintained.The problems such as that this method solve conventional ionic liquids is expensive, inferior separating effect provides possibility for the industrialization of ionic liquid pretreatment biomass, belongs to novel biomass pre-treatment solvents.
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 I profile material of high purity cellulose, belong to biomass field.
Background technique
With the increasingly failure of earth fossil resource, energy and environment problem, which has become in human industryization development, to be needed
Green renewable resource is developed and used to the important problem of solution, realizes that efficient utilize of resource is to solve current chemical industry
The effective way developed slowly.Biomass resource big, widespread green regenerative energy sources as reserves on the earth, in recent years
Research and probe in receive the extensive concern of people.Other than forest cover, agricultural crop straw and a variety of annual plants
Object stalk also plays an important role in the substance of nature and energy circulation.Main composition portion as biomass resource
Point, cellulose, hemicellulose and lignin can be extracted and are used by the technique of biorefinery.Cellulose
(35-55%) and hemicellulose (20-35%) can be decomposed into glucose and xylose, and be converted by the method for biological and chemical
The chemicals such as a variety of pharmaceutical intermediates and alcohol fuel, gasoline and glycol are 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.Corn stover, cotton stalk, reed rod and wood
Consider the agricultural wastes of these low costs to be worth doing, the lignocellulosic of itself is renewable resource valuable in nature.
By carrying out separated and dissolved pretreatment to lignocellulosic labyrinth, biomass components cellulose and half fiber are realized
Dimension element, lignin efficiently separate be biomass resource utilization committed step, wherein for the separation and Extraction and benefit of cellulose
With particularly important.Solvent used in conventional pretreatment technical process mostly acid, aqueous slkali or organic solvent, but these solvents
System is generally existing, and environmental pollution is serious, the problems such as cannot recycling, is stringent to equipment requirement and at high cost.
Ionic liquid receives the extensive concern of people as reaction medium and solvent in research in recent years.Ion
The advantages that liquid has thermal stability good, hardly possible volatilization, recyclable, has been widely used for organic synthesis, industry is urged
Change and the fields such as extraction and separation.Ionic liquid at room temperature can form stronger ionic liquid hydrogen bond action with biomass components, this
New approaches are provided for its component separated and dissolved for being applied to biomass.Conventional single ionic liquid separated and dissolved wood fibre
For plain component there are two types of thinking, a kind of thinking is with the fibre in the dissolution preferable ion liquid dissolving lignocellulosic of cellulose ability
Dimension element, then regeneration obtains the cellulose Ⅱ profile 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
Processing separation and the method using lignocellulosic.Another thinking is that use removes the preferable ionic liquid of lignin dissolution
Lignin in biomass components, obtains fiber-rich cellulosic material, and 103031762 A of patent CN has then used this method.
Ionic liquid mainly includes N- methylimidazole, ammonium salt class and microcosmic salt for the cation of biomass components dissolution
Class, anion are mainly X-(halogen), CH3COO-、CH3SO4 -、(CH3)2O2PO2 -And HCO2 -Deng, however most of single ionics
Liquid can not achieve efficiently separating for cellulose and hemicellulose in lignocellulosic component, and synthesis step is more, cost
Height can destroy the crystalline structure of cellulose in raw material by the cellulosic material for dissolving and regenerating, in subsequent application
In be restricted, meanwhile, in separated and dissolved use dimethyl sulfoxide organic solvent, environmental pollution is serious, does not meet sustainable development
The theory of exhibition and green processes engineering.
Summary of the invention
The present invention provides a kind of polyhydroxy proton type ammonium salt class ionic liquids as separated and dissolved lignocellulosic component
Solvent, one-step method can make lignin in biomass material and hemicellulose while remove, and obtain I fiber type of higher degree
Cellulosic material.Ionic liquid general structure is as follows:
Method for synthesizing ionic liquid used in the present invention is as follows:
Under the conditions of 273.15K temperature, appropriate Loprazolam is titrated into the methanol that funnel is slowly dropped into hydramine by constant pressure
In solution, after being added dropwise, it is warming up to room temperature reaction 48h, stops reaction, rotary evaporation removes methanol solvate, uses ether respectively
Three times with ethyl acetate washing, finally the ionic liquid of synthesis is dried in vacuo.
It is as follows to the separated and dissolved experimental procedure of lignocellulosic:
Biomass starting material stalk is first washed with neutral detergent, dry, pulverize and be sieved, filters out certain particle size
(≤0.125mm) lignocellulosic material.
Heating stirring in flask is added in the lignocellulosic material of mass fraction 5%-10% and ionic liquid simultaneously.
Experimental temperature is 80-160 DEG C, reaction time 0.25-24h, wooden under the microscope in polarized light microscopy every 0.5h
Cellulosic component dissolves situation.After reaction, the dilution centrifugation of 10mL deionized water is added into system, consolidates what centrifugation obtained
Body is washed 3-6 times, and high purity cellulose material is dried to obtain.
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
The disadvantages of method is cumbersome, at high cost.
The ionic liquid of 2 inventions shows excellent separated and dissolved ability to lignocellulosic, can dissolve simultaneously wooden
Lignin and hemicellulose in cellulosic component obtain the cellulose Ⅰ profile material that purity is 70-95%, maintain stalk original
The crystalline structure of cellulose in material.
3 pairs of hydroxy kind ion liquid dissolving separating effects are best, meanwhile, cellulose is insoluble in experiment, and product is easy to point
From low energy consumption, provides possibility for the industrialization of ionic liquid separating biomass components.
Ionic liquid and water have only been used in separated and dissolved experiment in 4 inventions, eliminate conventional ionic liquid separated and dissolved stalk
Dimethyl sulfoxide diluent used in different component, it is more environmentally protective, meet the theory of green processes engineering.
Detailed description of the invention
Attached drawing is specific embodiment 1, embodiment 2, embodiment 3, embodiment 4, embodiment 5, embodiment 6, the fibre of embodiment 7
Tie up the XRD comparison diagram of cellulosic material and stalk and cotton haulm raw material.
Fig. 1 specific embodiment 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 diagram of embodiment 11.
The cellulosic material and cotton stalk raw material XRD comparison diagram of Fig. 2 specific embodiment 7.
Specific embodiment
The present invention is further illustrated below with reference to embodiment, and still, specific embodiment is not constituted pair in any way
The limitation of the scope of the invention.
Embodiment 1
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) maize straw powder, 120 DEG C of items
Magnetic agitation for 24 hours, the dilution of 10mL deionized water, centrifugation point is added into the ionic liquid and stalk mixture after reaction under part
From.By the undissolved product of gained using clear water cleaning, dry, weighing, the solubility of the ionic liquid is calculated, 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 is increased to 91.81% from 50.53%.
Embodiment 2
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) maize straw powder, 120 DEG C of items
The dilution of 10mL deionized water, centrifugation point are added into the ionic liquid and stalk mixture after reaction by magnetic agitation 0.25h under part
From.By the undissolved product of gained using clear water cleaning, dry, weighing, the solubility of the ionic liquid is calculated, 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 is increased to 76.53% from 50.53%.
Embodiment 3
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) maize straw powder, 80 DEG C of items
The dilution of 10mL deionized water, centrifuge separation are added into the ionic liquid and stalk mixture after reaction by magnetic agitation 6h under part.
By the undissolved product of gained using clear water cleaning, dry, weighing, the solubility of the ionic liquid is calculated, and product is subjected to wood
The analysis of matter cellulosic component.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 is increased to 70.00% from 50.53%.
Embodiment 4
To by dry 10g proton type ionic liquid solvent triethanolamine methane sulfonates ([(HOCH2CH2)3NH]+
CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) maize straw powder, magnetic force under the conditions of 160 DEG C
6h is stirred, the dilution of 10mL deionized water, centrifuge separation are added into the ionic liquid and stalk mixture after reaction.Not by gained
Dissolved product calculates the solubility of the ionic liquid, and product is carried out lignocellulosic using clear water cleaning, dry, weighing
Component analysis.Composition analysis result shows that content of lignin drops to 5.45% from the 15.28% of raw material in product, hemicellulose
Cellulose content drops to 5.44% from 31.21%, and content of cellulose is increased to 82.44% from 50.53%.
Embodiment 5
To by dry 10g proton type ionic liquid solvent N, N- dimethylethanolamine methane sulfonates
([(HOCH2CH2)NH(CH3)2]+CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) corn stover
It is dilute that 10mL deionized water is added into the ionic liquid and stalk mixture after reaction by powder, magnetic agitation 6h under the conditions of 140 DEG C
It releases, be centrifugated.By the undissolved product of gained using clear water cleaning, dry, weighing, the solubility of the ionic liquid is calculated, and
Product is subjected to 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 is increased to from 50.53%
78.01%.
Embodiment 6
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in 1.0g is added by washing, dry, sieving (≤0.125mm) maize straw powder, 130 DEG C of items
The dilution of 10mL deionized water, centrifuge separation are added into the ionic liquid and stalk mixture after reaction by magnetic agitation 6h under part.
By the undissolved product of gained using clear water cleaning, dry, weighing, the solubility of the ionic liquid is calculated, and product is subjected to wood
The analysis of matter cellulosic component.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 is increased to 76.10% from 50.53%.
Embodiment 7
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) cotton stalk powder end, under the conditions of 130 DEG C
The dilution of 10mL deionized water, centrifuge separation are added into the ionic liquid and stalk mixture after reaction by magnetic agitation 6h.By institute
Undissolved product is obtained using clear water cleaning, dry, weighing, calculates the solubility of the ionic liquid, and product is subjected to wooden fibre
Tie up plain component analysis.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 is increased to 75.10% from 43.98%.
Embodiment 8
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)3NH]+CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) maize straw powder, under the conditions of 150 DEG C
The dilution of 10mL deionized water, centrifuge separation are added into the ionic liquid and stalk mixture after reaction by magnetic agitation 6h.By institute
Undissolved product is obtained using clear water cleaning, dry, weighing, calculates the solubility of the ionic liquid, and product is subjected to wooden fibre
Tie up plain component analysis.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 is increased to 83.32% from 50.53%.
Embodiment 9
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) maize straw powder, 120 DEG C of items
The dilution of 10mL deionized water, centrifugation point are added into the ionic liquid and stalk mixture after reaction by magnetic agitation 0.75h under part
From.By the undissolved product of gained using clear water cleaning, dry, weighing, the solubility of the ionic liquid is calculated, 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 is increased to 82.05% from 50.53%.
Embodiment 10
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in 0.5g is added by washing, dry, sieving (≤0.125mm) maize straw powder, 120 DEG C of items
The dilution of 10mL deionized water, centrifuge separation are added into the ionic liquid and stalk mixture after reaction by magnetic agitation 1h under part.
By the undissolved product of gained using clear water cleaning, dry, weighing, the solubility of the ionic liquid is calculated, and product is subjected to wood
The analysis of matter cellulosic component.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 is increased to 82.25% from 50.53%.
Embodiment 11
To by dry 10g proton type ionic liquid Solvents N-methyl diethanol amine methane sulfonates ([(HOCH2CH2)2NH(CH3)]+CH3SO4 -) in 0.8g is added by washing, dry, sieving (≤0.125mm) maize straw powder, 130 DEG C of items
The dilution of 10mL deionized water, centrifuge separation are added into the ionic liquid and stalk mixture after reaction by magnetic agitation 6h under part.
By the undissolved product of gained using clear water cleaning, dry, weighing, the solubility of the ionic liquid is calculated, and product is subjected to wood
The analysis of matter cellulosic component.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 is increased to 75.10% from 50.53%.
Claims (2)
1. a kind of method with proton type ammonium salt class ionic liquid pretreatment separation lignocellulosic component, it is characterised in that with matter
Subtype ammonium salt class ionic liquid is solvent, under the conditions of 120-160 DEG C of temperature and 6-24h, the wood for being 5%-10% by mass fraction
Heating stirring in reaction flask is added in matter cellulosic material together with ionic liquid, after reaction, deionization is added into system
Water dilution cooling, is centrifugated the not molten object of solid, and solid is washed, the crystal form for the cellulose in raw material of being maintained after dry
Structure, content reach the I fiber type cellulosic material of 70-95%;Lignin dissolution removal rate and hemicellulose dissolution removal rate are
40-95%;
The structure of the proton type ammonium salt class ionic liquid is as follows:
R1=CH2CH2OH, CH2CH2CH2OH, CH2CH2CH2CH2OH;
X-=CH3SO3 -, CH3COO-, CF3SO3 -,,。
2. the method according to claim 1, wherein the lignocellulosic material is corn stover, cotton stalk, dog
Tail grass, reed rod, agropyron or sawdust.
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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 |
CN109704902B (en) * | 2018-12-28 | 2021-02-19 | 中国科学院过程工程研究所 | Ionic liquid catalytic deoxidation method in lignin derivative hydrodeoxygenation process |
FI20196131A1 (en) * | 2019-12-23 | 2021-06-24 | Metsae Fibre Oy | Dispersion of cellulose fibers and method of producing the same |
CN111154817B (en) * | 2020-02-19 | 2022-04-08 | 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 |
CN113882179B (en) * | 2021-09-29 | 2022-10-11 | 江南大学 | Method for removing lignin in straw by using nitric acid 1-hydroxy-3-mercaptopropane-2-amine |
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