CN106519260A - Method for separating lignin from agricultural waste by using composite ionic liquid - Google Patents
Method for separating lignin from agricultural waste by using composite ionic liquid Download PDFInfo
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- CN106519260A CN106519260A CN201611019798.XA CN201611019798A CN106519260A CN 106519260 A CN106519260 A CN 106519260A CN 201611019798 A CN201611019798 A CN 201611019798A CN 106519260 A CN106519260 A CN 106519260A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
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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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Abstract
The invention discloses a method for efficiently separating lignin from agricultural waste by using a composite ionic liquid system. The method comprises the following steps: (1) preparation of composite ionic liquid: subjecting composite ionic liquid with cooperative effect to mechanical mixing or double-anion ion exchange; (2) pretreatment of agricultural waste: fully drying the agricultural waste, then crushing the agricultural waste to a size of 20 to 60 meshes by using a mechanical crushing method, washing the soluble components of crushed agricultural waste with acetone and deionized water successively and thoroughly drying the agricultural waste for subsequent usage; and (3) and delignification of the agricultural waste: fully mixing 5 to 500 g of the composite ionic liquid with 1.5 to 60 g of the agricultural waste and carrying out a reaction in an inert atmosphere at a temperature of 120 to 260 DEG C under stirring so as to obtain high-purity lignin and biological micromolecular substances. According to the method, the content of the obtained lignin is high; the usage amount of the ionic liquid is low; and the composite ionic liquid is cyclically usable and does not need addition of deionized water.
Description
Technical field
The invention belongs to environmental protection technology, Comprehensive Utilization of Agricultural Wastes and new energy technology development and utilization neck
The method of the lignins of agricultural wastes such as domain, more particularly to a kind of utilization compound ion liquid system high efficiency separation bagasse.
Background technology
Lignin is the second largest natural polymerses for being only second to cellulose, and it is the important component of biomass,
There is very important application in chemical engineering industry.Biomass are directed to the photosynthesis of green plantss, therefore which is in nature
Widely distributed in boundary, rich content is a kind of great potential, cheap, reproducible low-carbon (LC) alternative energy source, current to alleviating
Increasingly serious energy crisis and due to have the problems such as environmental pollution caused by disposable fossil energy of burning in a large number lift foot
The meaning of weight.But the alternative energy sources such as current biodiesel and Ethanol are essentially from cereal crops such as saccharide, starch
Fermentation and hydrolyze, although therefore its part alleviate energy crisis, bring great pressure to grain security.Therefore develop non-
The efficient utilization new technique of cereal crops and agricultural wastes lignocellulose becomes the focus of current concern.Current biology
Matter processing mode such as gasification, pyrolysis, liquefaction etc. exist it is such or deficiency, be particularly due to biomass molecule and have
Higher degree of crystallinity and intermolecular and intramolecular hydrogen bond make which not dissolve in H2The organic solvent of O and routine, this greatly hinders
The development and utilization of biomass and biomass energy.
2002, Robin D.Rogers etc. had found that ionic liquid 1-butyl-3-methyl imidazolium villaumite (bmimCl) can have
Effect ground dissolving cellulose, at 100 DEG C, its dissolubility is up to 10wt%, subsequently, a series of functionalized ion liquids such as acetate
Ionic liquid, allyl functional ionic liquid etc. are also developed for the dissolving of the materials such as cellulose, hemicellulose successively.
However, due to its limited dissolubility in ionic liquid, the large usage quantity of above-mentioned system ionic liquid, and first must be molten by which
Homogeneous phase solution is formed in ionic liquid, then this homogeneous phase solution could be extracted and be converted, therefore intermediate steps are more, grasped
Make loaded down with trivial details.Significantly in current ionic liquid, lignocellulose treatment technology need to add certain water, and water is already
It is proved to be obstruction primary factor of the ionic liquid to the effective dissolving of biomass.
The content of the invention
In order to overcome the deficiencies in the prior art and shortcoming, the primary and foremost purpose of the present invention is to provide a kind of using multiple
The method for closing lignin in the agricultural wastes such as ion liquid system high efficiency separation bagasse.By efficient cryogenic catalyzed conversion fiber
Element, the mode of hemicellulose are realized the high efficiency separation of lignin and prepare the be directly used as industrial chemicals and chemical industry of high added value
The small molecule biochemicals of intermediate.
The purpose of the present invention is realized by following technical proposals：
A kind of method of lignin in utilization compound ion liquid system high efficiency separation agricultural wastes, including following operation step
Suddenly：
(1) preparation of compound ion liquid：Compound ion liquid with cooperative effect is drawn by mechanical mixture or dianion
Send out agent ion exchange to be obtained.
(2) pretreatment of agricultural wastes：Using the method for mechanical activation comminution by its powder after agricultural wastes are fully dried
It is broken to 20～60 mesh, and abundant drying for standby after successively washed its soluble component；
(3) delignification of agricultural wastes：5～500g compound ion liquids and 1.5～60g agricultural wastes are sufficiently mixed,
Inert atmosphere；Reaction temperature is 120～260 DEG C, reacts under agitation and obtains highly purified lignin and little point of biology
Sub- material.The biological micromolecule material is mainly ester, alcohol, aldehyde, ketone, furfural and its derivant, the furans of high added value and spreads out
The material that biological and long-chain hydro carbons etc. directly can be utilized.
Preferably, the inert atmosphere is N2, mixing speed is 100～1000r/min；Response time is 5～120min.
Preferably, the agricultural wastes are one or more in bagasse, straw, rice husk, straw and Caulis et Folium Oryzae.
Preferably, compound ion liquid prepares approach 1：By 5～500g lignocellulose is had solubility property from
Sub- liquid flux and 0.1～10mol acidic ionic liquid catalysts are in N2It is sufficiently mixed in ice-water bath under protection, is combined
Ionic liquid.
Preferably, compound ion liquid prepares approach 2：0.1～20mol chloride salt ions liquid precursors are dissolved in into 10～
In the absolute methanol of 1000mL, then the KHSO of 0.05～10mol is being added thereto to4, Jing after fully reacting, control Cl-With
HSO4 -Concentration ratio be (10～30): 1, remove solvent, obtain compound ion liquid.
Preferably, the cation of the ion liquid solvent is alkyl imidazole；Alkyl pyridine；Alkyl quaternary amine；Pi-allyl miaow
Azoles；Allyl pyridine；Pi-allyl quaternary amine；Anion is chloride ion, acetate, formate, Methylsulfate, ethyl-sulfate, phosphoric acid
Methyl ester, etherophosphoric acid.
The anion is Cl-, Br-Ion liquid solvent is combined to using quaternary amine；Other ion liquid solvents pass through villaumite
Presoma and corresponding potassium salt are obtained by ion exchange at room temperature；Bisulfate ion, biphosphate root type conventional acid from
Sub- liquid is obtained by above-mentioned similar ion exchange；Other functions ionic liquid adopts acid-base neutralization method and microwave-assisted
Means synthesize.
The anion is Cl-, Br-Ion liquid solvent is prepared according to the following steps：By 0.1～5mol N- methyl miaows
Azoles, pyridine or alkylamine and 0.12～6mol 1- chloralkanes or brominated alkanes are sufficiently mixed, under the conditions of 40 DEG C stirring 12～
After 24h, 70 DEG C are warming up to, continue 24～48h of stirring, obtain mixed solution；Mixed solution vacuum Jing after ethyl acetate washing is done
It is dry, obtain Cl-Salt or Br-Ionic liquid.
Described other anion liquid fluxs are prepared according to the following steps：(quality is by homologue to weigh 0.1～10mol
The molal weight of the material of matter determines) Cl-Ionic liquid presoma is simultaneously dissolved in the methanol of 10～2000mL；Then
The amount for weighing material is Cl-The potassium salt of the corresponding cation of 1～2 times of ionic liquid (rubbed by the material of respective substance by quality
You determine quality), it is dissolved in 30～300mL methanol；Merge and under above-mentioned solution, room temperature, stir 24h, filter, filtrate is using rotation
The mode of evaporation removes solvent, and 70 DEG C of 12～36h of drying in vacuum drying oven are placed in after washing 3 times with absolute ether, obtains
Ion liquid solvent.
The bisulfate ion, biphosphate root type conventional ionic liquid are prepared according to the following steps：Weigh 0.1～
The Cl of 10mol (quality is determined by the molal weight of the material of respective substance)-Ionic liquid presoma it is dissolved in 10～
In the methanol of 2000mL；Then the amount for weighing material is Cl-The KHSO that 1～2 times of ionic liquid4Or KH2PO4(quality is by corresponding
The molal weight of the material of material determines), it is dissolved in 30～300mL methanol；Merge and under above-mentioned solution, room temperature, stir 24h, mistake
Filter, filtrate remove solvent using rotary evaporation by the way of, and be placed in after washing 3 times with absolute ether in vacuum drying oven 70 DEG C it is dry
Dry 12～36h, obtains acidic ion liquid.
The carboxylic acid and sulfonic acid funtionalized ionic liquid are prepared according to the following steps：By 0.1～10mol N- methyl miaows
Azoles, pyridine or alkylamine and wait the amount of material Isosorbide-5-Nitrae-alkyl sultone be sufficiently mixed and 30～50 DEG C stirring 10～24h, institute
Solid is washed and is gone in flask after being vacuum dried Jing ethyl acetate, and the acid of the amount of material such as add, continue 50～80
12～48h is stirred at DEG C, gained liquid Jing after absolute ether washing is vacuum dried 24～48h, obtains alkyl sulfonic acid ylmethyl miaow
Azoles bisulfate ion acidic ion liquid.
The carboxylic acid functional ionic liquid is prepared according to the following steps：By 0.1～10mol N- Methylimidazole .s, pyridine
Or alkylamine and etc. the chlorinated carboxylic acid of the amount of material be sufficiently mixed and be stirred at room temperature 10～24h, products therefrom Jing acetic acid second
After ester is washed and absolute ether is washed, 24～48h is vacuum dried, alkyl sulfonic acid ylmethyl imidazoles bisulfate ion acid ion is obtained
Liquid.
The present invention principle be：The present invention builds a series of to sugarcane with 1- butyl -3- methylimidazole villaumites (bmimCl) etc.
Cellulose, hemicellulose in the agricultural wastes such as slag, Caulis et Folium Oryzae, straw, straw, rice husk has the ionic liquid of excellent dissolution performance
Body is solvent, with 1- fourth sulfonic group -3- methylimidazolium hydrogen sulphate salt (C4H8SO3HmimHSO4) etc. have homogeneous and heterogeneous catalysiss concurrently
Compound ion liquid of the functionalized acidic ionic liquid of agent advantage for catalyst, the efficient catalytic conversion under certain process conditions
Cellulose, hemicellulose in the richness carbon agricultural wastes such as bagasse is prepared and can be directly used as the little of the raw material of industry and chemical intermediate
Molecular biochemistry product (biochemical), so as to successfully realize the high efficiency separation of lignin, breach biomass comprehensive utilization
In phase problem obstacle, in solving current techniques, biological matter reactor efficiency is low, the difficult problem such as catalyst is not easily recycled, and realizes
The efficient utilization of agricultural wastes is separated with the high selectivity of lignin.
The technology of the present invention is successfully realized wood in the agricultural wastes such as bagasse using one-step method under conditions of without water
High efficiency separation of the quality in ionic liquid.In the process, what ion liquid solvent dissolving lignocellulose was formed mixes
Liquid enables it to preferably contact with acidic ionic liquid catalysts, the conversion of the component such as more high activity ground catalytic cellulose, from
And make reaction condition gentleer；Acidic ion liquid is in situ to be turned the cellulose being dissolved in ion liquid solvent and hemicellulose
Change, so as to promote its dissolution equilibrium in ion liquid solvent, reduce the consumption of ionic liquid, improve its conversion
Rate；One-step method eliminates middle separation process, therefore its conversion process is simpler, and the separating effect of lignin is more preferable, more
Environmental friendliness.
Hinge structure of the present invention has the following advantages and effect：
(1) the compound ion liquid catalyst system and catalyzing that the present invention is provided realizes the high selectivity separation of lignin, wood in solidss
The content of quality is up to 65.5%；
(2) the inventive method can efficiently realize cellulose, the homogeneousization conversion of hemicellulose in the agricultural wastes such as bagasse；
Under conditions of gentle, cellulose, the conversion ratio of hemicellulose are close to 100%；
(3) the compound ion liquid catalyst system and catalyzing that the present invention is provided can utilize ionic liquid to the dissolving of lignocellulose simultaneously
Ira situ degradation, while lignin high efficiency separation is realized and cellulose, hemicellulose high activity are converted, also greatly reduces
The consumption of ionic liquid, and improve the efficiency of reactor；
(4) present invention provide one-step method degrade agricultural wastes method process is simple, cost and operating cost it is low, save
Separate intermediate stages of the prior art；
(5) catalyst system and catalyzing that the present invention is provided possesses good recycling performance.
Specific embodiment
Further detailed description, but embodiments of the present invention not limited to this are done to the present invention with reference to embodiment.
Embodiment 1
A kind of method of the lignin of utilization compound ion liquid system high efficiency separation agricultural wastes, operating procedure are as follows：
(1) preparation of compound ion liquid：By 5g ion liquid solvents 1- butyl -3- methylimidazole villaumites (bmimCl) and
0.1mol acidic ionic liquid catalysts 1- fourth sulfonic group -3- methylimidazolium hydrogen sulphate salt (C4H8SO3HmimHSO4) in N2Protection
Under ice-water bath in be sufficiently mixed, obtain compound ion liquid；
(2) pretreatment of agricultural wastes：Method after bagasse is fully dried using mechanical activation comminution is crushed to 20～60
Mesh.And successively dissolved in Organic substance and water with acetone and deionized water component wash after abundant drying for standby；
(3) delignification of agricultural wastes：Gained compound ion liquid 20g and 1.5g bagasse in step (1) is fully mixed
Close, reaction system Jing N2After displacement 3 times, 220 DEG C are heated to, 15min are reacted under stirring condition (speed 300r/min), react
Reactor is cooled to into room temperature after end, material in kettle is poured out, and is fully diluted with 200mL water, filtered, be dried.Gained solid
In thing, the content of lignin is up to 65.5%.Cellulose and hemicellulose almost 100% be converted into aldehyde, ketone, butyl ester, methyl ester,
The small molecule biochemicals such as Furan and its derivatives.
Embodiment 2
The present embodiment with the difference of embodiment 1 is：
(1) preparation of compound ion liquid：By 50g ion liquid solvents 1- butyl -3- Methylimidazole. acetate (bmimAc) and
1mol acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphate salt (bmimHSO4) in N2In ice-water bath under protection
It is sufficiently mixed, obtains compound ion liquid；
(3) delignification of agricultural wastes：100g above-mentioned compound ion liquid and 20g rice husks are sufficiently mixed, reaction system
Jing N2After displacement 3 times, 200 DEG C are heated to, 30min is reacted under stirring condition (speed 500r/min), reaction will be anti-after terminating
Answer kettle to be cooled to room temperature, pour out material in kettle, and fully diluted with 400mL water, filter, experiment gained solid is detected after drying
Show that the content of lignin in solidss is up to 61.4%.The conversion ratio of cellulose and hemicellulose is 94.2%.
Embodiment 3
The present embodiment with the difference of embodiment 1 is：
(1) preparation of compound ion liquid：By 200g to ion liquid solvent 1- ethyl-3-methylimidazole Methylsulfates
(emimMeSO4) and 5mol acidic ionic liquid catalysts 1- fourth sulfonic acid yl pyridines disulfate (C4H8SO3HPyHSO4) in N2Protect
It is sufficiently mixed in ice-water bath under shield, obtains compound ion liquid；
(3) delignification of agricultural wastes：500g above-mentioned compound ion liquid and 60g straws are sufficiently mixed, reaction system
Jing N2After displacement 3 times, 240 DEG C are heated to, 5min is reacted under stirring condition (speed 1000r/min), reaction will be anti-after terminating
Answer kettle to be cooled to room temperature, pour out material in kettle, and fully diluted with 500mL water, filter, lignin in experiment gained solidss
Content is up to 65.2%；Cellulose and hemicellulose almost 100% are converted into aldehyde, ketone, butyl ester, methyl ester, furan and its derivative
The small molecule biochemicals such as thing.
Embodiment 4
A kind of method of the lignin of utilization compound ion liquid system high efficiency separation agricultural wastes, including following operation step
Suddenly：
(1) preparation of compound ion liquid is (with the chloro- bisulfate ion ((bmim) of 1- butyl -3- Methylimidazole .s2ClHSO4) be
Example)：1mol N- methylimidazole villaumites are dissolved in the absolute methanol of 100mL, are then being added thereto to 0.05mol's
KHSO4, Jing after fully reacting, by its anion concentration of ion chromatography, make Cl-And HSO4 -Concentration ratio be 20: 1, remove
After going solvent, gained liquid to be washed with ether, 24h is vacuum dried.
(2) pretreatment of agricultural wastes：Method after Caulis et Folium Oryzae is fully dried using mechanical activation comminution is crushed to 20
～60 mesh.And successively dissolved in Organic substance and water with acetone and deionized water component wash after abundant drying for standby；
(3) delignification of agricultural wastes：10g above-mentioned compound ion liquid and 1.5g Caulis et Folium Oryzaes are sufficiently mixed, reaction system
Jing N2After displacement 3 times, 200 DEG C are heated to, 15min is reacted under stirring condition (speed 400r/min), reaction will be anti-after terminating
Answer kettle to be cooled to room temperature, pour out material in kettle, and fully diluted with 100mL water, filter, lignin in experiment gained solidss
Content is up to 61.3%；Cellulose and hemicellulose almost 100% are converted into aldehyde, ketone, butyl ester, methyl ester, furan and its derivative
The small molecule biochemicals such as thing.
Embodiment 5
The present embodiment with the difference of embodiment 4 is：
(1) preparation of compound ion liquid is (with the chloro- bisulfate ion of 1- butyl-pyridiniums ((bPy)2ClHSO4) as a example by)：By 1mol
1- butyl-pyridinium villaumites are dissolved in the absolute methanol of 100mL, are then being added thereto to the KHSO of 0.05mol4, Jing fully reacts
Afterwards, by its anion concentration of ion chromatography, make Cl-And HSO4 -Concentration ratio be 15: 1, remove solvent, gained liquid use
After ether washing, 24h is vacuum dried.
(3) delignification of agricultural wastes：Compound ion liquid obtained by 500g and 60g rice husks are sufficiently mixed, are reacted
System Jing N2After displacement 3 times, 200 DEG C are heated to, 30min are reacted under stirring condition (speed 200r/min), after reaction terminates
Reactor is cooled to into room temperature, material in kettle is poured out, and is fully diluted with 1000mL water, filtered, wood in experiment gained solidss
The content of quality is up to 61.5%；95.2% cellulose and hemicellulose are converted into aldehyde, ketone, butyl ester, methyl ester, furan and its spread out
The small molecule biochemicals such as biology.
Embodiment 6
The present embodiment with the difference of embodiment 4 is：
(1) with the chloro- bisulfate ion of 4-butyl amine ((bPy)2ClHSO4) compound ion liquid preparation：By 5mol tetrabutyl pyrroles
Pyridine villaumite is dissolved in the absolute methanol of 500mL, is then being added thereto to the KHSO of 0.25mol4, Jing after fully reacting, pass through
Ion chromatography its anion concentration, makes Cl-And HSO4 -Concentration ratio be 30: 1, remove solvent, gained liquid washed with ether
After washing, 24h is vacuum dried.
(3) delignification of agricultural wastes：Compound ion liquid obtained by 100g and 30g straws are sufficiently mixed, are reacted
System Jing N2After displacement 3 times, 260 DEG C are heated to, 45min are reacted under stirring condition (speed 300r/min), after reaction terminates
Reactor is cooled to into room temperature, material in kettle is poured out, and is fully diluted with 600mL water, filtered, it is wooden in experiment gained solidss
The content of element is up to 63.2%；Cellulose and hemicellulose almost 100% be converted into aldehyde, ketone, butyl ester, methyl ester, furan and its
The small molecule biochemicals such as derivant.
Embodiment 7
The reusability of compound ion liquid in embodiment 1：
By the compound ion liquid Jing CH in above-described embodiment 12Cl2After extraction and desolvation, repeat the operation of embodiment 1,
The catalyst system and catalyzing that the visible present invention of experimental results is provided possesses good recycling performance.
It is the present invention preferably embodiment in above-described embodiment, but embodiments of the present invention does not receive above-described embodiment
Restriction, other any spirit without departing from the present invention and the change, modification, replacement made under principle, combine, it is simple
Change, should be equivalent substitute mode, be included within protection scope of the present invention.
Claims (3)
1. in a kind of utilization compound ion liquid separating agricultural garbage lignin method, it is characterised in that including following step
Suddenly：
（1）The preparation of compound ion liquid：Compound ion liquid with cooperative effect is drawn by mechanical mixture or dianion
Send out agent ion exchange to be obtained；Concrete grammar is：
Ion liquid solvent and 0.1～10mol acidic ion liquids that 5～500g has solubility property to lignocellulose are urged
Agent is in N2It is sufficiently mixed in ice-water bath under protection, obtains compound ion liquid；
Or, 0.1～20mol chloride salt ions liquid precursors are dissolved in the absolute methanol of 10～1000mL, then to which
The KHSO of 0.05～10mol of middle addition4, Jing after fully reacting, control Cl-And HSO4 -Concentration ratio be（10～30）:1, remove
Solvent, obtains compound ion liquid；
（2）The pretreatment of agricultural wastes：Method after agricultural wastes are fully dried using mechanical activation comminution is crushed to
20～60 mesh, and abundant drying for standby after successively washed its soluble component；
（3）The delignification of agricultural wastes：5～500g compound ion liquids and 1.5～60g agricultural wastes are sufficiently mixed,
Inert atmosphere；Reaction temperature is 120～260 DEG C, reacts under agitation and obtains highly purified lignin and little point of biology
Sub- material.
2. method according to claim 1, it is characterised in that：The cation of the ion liquid solvent be alkyl imidazole,
Alkyl pyridine, alkyl quaternary amine, allyl imidazole, allyl pyridine or pi-allyl quaternary amine；Anion is chloride ion, acetate, first
Acid group, Methylsulfate, ethyl-sulfate, methyl orthophosphoric acid or etherophosphoric acid.
3. the method stated according to claim 2, it is characterised in that：Step（3）The agricultural wastes be bagasse, straw, rice husk,
One or more in straw and Caulis et Folium Oryzae.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108166293A (en) * | 2017-12-04 | 2018-06-15 | 湖南省农业科学院 | The method and its system of a kind of irradiation-plant fibrous agricultural wastes of chemical method Combined Treatment |
| CN110240921A (en) * | 2019-06-19 | 2019-09-17 | 广东石油化工学院 | A kind of method of lychee dregs catalytic liquefaction |
| CN111138683A (en) * | 2020-01-19 | 2020-05-12 | 茂名市红福化学有限公司 | Sodium lignosulfonate water reducing agent and preparation method thereof |
| CN111744326A (en) * | 2019-03-26 | 2020-10-09 | 天津大学 | Novel eutectic solvent and method for absorbing sulfur dioxide by using same |
-
2016
- 2016-11-21 CN CN201611019798.XA patent/CN106519260A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108166293A (en) * | 2017-12-04 | 2018-06-15 | 湖南省农业科学院 | The method and its system of a kind of irradiation-plant fibrous agricultural wastes of chemical method Combined Treatment |
| CN111744326A (en) * | 2019-03-26 | 2020-10-09 | 天津大学 | Novel eutectic solvent and method for absorbing sulfur dioxide by using same |
| CN110240921A (en) * | 2019-06-19 | 2019-09-17 | 广东石油化工学院 | A kind of method of lychee dregs catalytic liquefaction |
| CN111138683A (en) * | 2020-01-19 | 2020-05-12 | 茂名市红福化学有限公司 | Sodium lignosulfonate water reducing agent and preparation method thereof |
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