CN105754114A - Method for separating and extracting straw lignin by using eutectic ionic liquid - Google Patents
Method for separating and extracting straw lignin by using eutectic ionic liquid Download PDFInfo
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Abstract
The invention relates to a process method for separating and extracting straw lignin by using eutectic ionic liquid. The method comprises the following steps of: adding a straw powder raw material and eutectic ionic liquid into a normal pressure reactor according to a certain mass ratio, performing mixing and stirring for reaction at 110-160 DEG C for a certain period of time, then regulating the pH value of the mixture to about 11 by using an alkali, performing high-speed centrifugation, and keeping an upper layer solution; and then regulating the pH value of the solution to be less than 3 by using an acid, performing centrifugation again, then washing and centrifuging a deposit by using distilled water until the supernatant is neutral, and performing freeze drying on the final deposit to obtain lignin. The method has the characteristics that the eutectic ionic liquid is prepared under a very mild condition by using low-price and nontoxic choline chloride and an H-bond donor as raw materials, and is used for separating and extracting lignin from rice straws, the raw materials are easy to obtain, the price is low, the process is simple, the condition is mild, the reaction is easy to control, and the energy consumption can be effectively reduced.
Description
Technical field
The invention belongs to chemical industry application field, the technique being specifically related to a kind of eutectic ionic liquid separation and Extraction straw lignin.
Background technology
In China, annual rice straw yield, up to 2.3 hundred million tons, is the renewable biomass resource of a kind of enormous amount, and natural reproducible resource is effectively utilized, have become as one of key of mankind nowadays sustainable development.And lignin is one of main composition in rice straw, its content is only second to cellulose, day by day in short supply along with petroleum resources, and lignin is originated as unique aromatic rings in Renewable resource, needs are more explored, and replace oil can synthesize more chemical industry and the articles for daily use with lignin.But due to wide variety, chemical constitution is complicated, do not have the reasons such as pure model thing, and the extracting and developing of lignin is still a great problem in this field with application.Log lignin is owing to relative molecular mass is big and lacks lyophily group, and the dissolubility in water and in usual solvents is poor, essentially insoluble solution.The traditional method extracting lignin from biological material is to react with concentrated sulphuric acid or dilute sulfuric acid, although efficiency is high, but environmental pollution is relatively big, is not suitable for large-scale promotion.Organic solvent lignin dissolves in dioxane, pyridine, methanol, ethanol, acetone and sig water, but must add little water in these solvents, otherwise almost insoluble.Therefore finding the separation method of a kind of new lignin is current study hotspot.The salt that ionic liquid is made up of organic cation and inorganic anion, is in a liquid state at normal temperatures.In recent years because it has stable performance, pollution-free, easily reclaim, and in improving reaction rate, selectivity and catalytic action etc., present clear superiority and receive much concern, enjoy the reputation of " green solvent ".Lignin dissolution and catalytic pyrolysis also have related application, particularly traditional imidazole-like ionic liquid such as chloro 1-butyl-3-Methylimidazole. ([Bmim] Cl) etc. are all stronger to lignin and cellulosic solvability, but owing to its biological degradability is poor, there is certain toxicity, and cost is 2～4 times even higher of usual vehicle, therefore, it is difficult to be used widely.Eutectic ionic liquid is a kind of eutectic mixture being made up of quaternary ammonium salt or slaine and hydrogen bond donor also known as eutectic solvent (DeepEutecticSolvents, DES).With conventional ion liquid phase ratio, its preparation technology is simple, raw material easily takes, cheap, without environment side effect, but it there is no application in the extraction to lignin from biomass.Disclosed by the invention is adopt one-step synthesis to prepare choline chloride system eutectic ionic liquid, and in order to separation and Extraction lignin from rice straw, the extraction for natural reproducible resource provides a kind of new method with utilizing, and has important economic implications and social meaning.
Summary of the invention
The purpose of the present invention: aim to provide a kind of raw material and be easy to get, the simple lignin extraction method of cheap, mild condition, process.Quaternary amine structure by choline chloride, when preparing eutectic ionic liquid, only the choline chloride of certain mol proportion and hydrogen bond donor need to be mixed and be incorporated under uniform temperature heated and stirred until forming homogeneous colourless liquid, and process rice straw powder as solvent, therefrom extract lignin.
Technical scheme: powder of straw raw material is added in normal pressure reactor with eutectic ionic liquid by certain mass ratio, mix at 110 DEG C～160 DEG C, after stirring reaction a period of time, the pH value of this mixture is adjusted to about 11 by the sodium hydroxide solution being about 10% by concentration, high speed centrifugation, retains upper solution.The pH value of this solution is adjusted to less than 3 by the sulphuric acid being about 10% by concentration, is repeatedly washed by precipitate distilled water, is centrifuged to the aobvious neutrality of supernatant after recentrifuge, and last precipitate is freeze-dried obtains lignin.
(1) method described in, wherein, eutectic ionic liquid is choline chloride system eutectic ionic liquid, be with choline chloride respectively with carbamide, glycerol, citric acid etc. for raw material at the temperate condition of 70～100 DEG C down to the transparent obtained various ionic liquid of reactant liquor；
(2) method described in, wherein, rice straw powder is after size-reduced for dried rice straw, ball milling, screening, will to take the powder of 40 order～100 orders, be dried to over dry gained；
(3) method described in, wherein, the ratio of choline chloride and the amount of substance of carbamide is 1: 1～1: 3, the ratio of choline chloride and the amount of substance of glycerol is 1: 1～1: 2, the ratio of choline chloride and the amount of substance of citric acid is 1: 1～3: 1.
(4) method described in, wherein, the mass ratio of eutectic ionic liquid and over dry rice straw powder is 100: 5～20；
(5) method described in, wherein, the insulation reaction time is 1h～10h.
The present invention compared with prior art has the advantage that
(1) solvent used by the present invention is choline chloride system eutectic ionic liquid, being with the raw material that cheap and nontoxic choline chloride and hydrogen bond donor are preparation eutectic ionic liquid, preparation-obtained as mild as a dove when, its preparation process is easy, reaction temperature is low, and the time is short.
(2) present invention is by the multiple synergism such as the solvent of eutectic ionic liquid, catalysis, activation, the lignin in separation and Extraction rice straw, and treatment conditions are gentle, and extraction process is simple, reacts easily controllable, and significantly reduces energy resource consumption.
Accompanying drawing explanation
Fig. 1 is the ultraviolet spectrogram that four kinds of ionic liquid extract rice straw lignins, and the maximum absorption band of four curves of gained is both present in about 210～220nm, for the absorption band of conjugation ethylene linkage, illustrates that dissolving gained lignin has bigger unsaturation；Additionally, the absworption peak of a moderate strength is had near 280nm, come from π → π * electron transition of the phenol (phenyl ring) of non-condensation in lignin component, illustrate the lignin structure extracted exists and the phenolic hydroxyl group of α position carbonyl conjugation, carbon-carbon double bond and biphenyl structural.
Fig. 2 is the infrared spectrogram that four kinds of ionic liquid extract rice straw lignin, and in figure, the appearance profile line of four curves is close, all there are several characteristic absorption peaks of lignin: 3400cm-1～3450cm-1It is the stretching vibration absworption peak of-OH, 2920cm-1It is the absworption peak of methyl, methylene and methine, 1735cm-1、1655cm-1Being respectively and the non-conjugated of aromatic rings and conjugation stretching vibration characteristic peak, the characteristic absorption of phenyl ring is mainly reflected in 1600cm-1、1510cm-1And 1420cm-1It it is the most obvious absworption peak in infrared spectrum.Compared with extracting lignin curve with [Bmim] Cl ionic liquid of comparative example 1, three kinds of self-control choline chloride system eutectic ionic liquid extract lignin curve at the 1600cm characterizing phenyl ring skeleton stretching vibration-1And 1512cm-1Absworption peak all demonstrates higher absorption, illustrates that the framing structure of lignin obtains good protection after eutectic ionic liquid processes.
Detailed description of the invention
Embodiment 1
Weighing choline chloride 35g, carbamide 30g, be separately added in the reaction vessel of sealing, stir 40min at 80 DEG C, reactant liquor is transparent, obtains Ch-U eutectic ionic liquid.It is slowly added to rice straw powder 3.25g, when being warming up to about 150 DEG C, after insulation reaction 5h, obtains modified lignin resin and DES mixture.The pH value of this mixture is adjusted to about 11 by the sodium hydroxide solution being about 10% by concentration, high speed centrifugation, retains upper solution.The pH value of this solution is adjusted to less than 3 by the sulphuric acid being about 10% by concentration, is repeatedly washed by precipitate distilled water, is centrifuged to the aobvious neutrality of supernatant after recentrifuge, and last precipitate is freeze-dried obtains lignin 0.195g.
Embodiment 2
Weighing choline chloride 35g, glycerol 46g, be separately added in the reaction vessel of sealing, stir 40min at 80 DEG C, reactant liquor is transparent, obtains Ch-G eutectic ionic liquid.It is slowly added to rice straw powder 4.05g, when being warming up to about 150 DEG C, after insulation reaction 5h, obtains modified lignin resin and DES mixture.The pH value of this mixture is adjusted to about 11 by the sodium hydroxide solution being about 10% by concentration, high speed centrifugation, retains upper solution.The pH value of this solution is adjusted to less than 3 by the sulphuric acid being about 10% by concentration, is repeatedly washed by precipitate distilled water, is centrifuged to the aobvious neutrality of supernatant after recentrifuge, and last precipitate is freeze-dried obtains lignin 0.505g.
Embodiment 3
Weighing choline chloride 35g, citric acid 48g, be separately added in the reaction vessel of sealing, stir 80min at 80 DEG C, reactant liquor is transparent, obtains Ch-C eutectic ionic liquid.It is slowly added to rice straw powder 4.15g, when being warming up to about 150 DEG C, after insulation reaction 5h, obtains modified lignin resin and DES mixture.With the sodium hydroxide solution being about 10% by concentration, the pH value of this mixture is adjusted to about 11, high speed centrifugation, retain upper solution.The pH value of this solution is adjusted to less than 3 by the sulphuric acid being about 10% by concentration, is repeatedly washed by precipitate distilled water, is centrifuged to the aobvious neutrality of supernatant after recentrifuge, and last precipitate is freeze-dried obtains lignin 0.65g.
Embodiment 4
Weighing choline chloride 35g, citric acid 48g, be separately added in the reaction vessel of sealing, stir 80min at 80 DEG C, reactant liquor is transparent, obtains Ch-C eutectic ionic liquid.It is slowly added to rice straw powder 4.15g, when being warming up to about 150 DEG C, after insulation reaction 2h, obtains modified lignin resin and DES mixture.The pH value of this mixture is adjusted to about 11 by the sodium hydroxide solution being about 10% by concentration, high speed centrifugation, retains upper solution.The pH value of this solution is adjusted to less than 3 by the sulphuric acid being about 10% by concentration, is repeatedly washed by precipitate distilled water, is centrifuged to the aobvious neutrality of supernatant after recentrifuge, and last precipitate is freeze-dried obtains lignin 0.61g.
Embodiment 5
Weighing choline chloride 35g, citric acid 48g, be separately added in the reaction vessel of sealing, stir 80min at 80 DEG C, reactant liquor is transparent, obtains Ch-C eutectic ionic liquid.It is slowly added to rice straw powder 4.15g, when being warming up to about 120 DEG C, after insulation reaction 5h, obtains modified lignin resin and DES mixture.The pH value of this mixture is adjusted to about 11 by the sodium hydroxide solution being about 10% by concentration, high speed centrifugation, retains upper solution.The pH value of this solution is adjusted to less than 3 by the sulphuric acid being about 10% by concentration, is repeatedly washed by precipitate distilled water, is centrifuged to the aobvious neutrality of supernatant after recentrifuge, and last precipitate is freeze-dried obtains lignin 0.505g.
Comparison example 1
By [Bmim] Cl ionic liquid 83g, when being warming up to about 150 DEG C, being slowly added to rice straw powder 4.15g, insulation magnetic agitation reaction 5h, the pH value of this mixture is adjusted to about 11 by the sodium hydroxide solution being about 10% by concentration, high speed centrifugation, retains upper solution.The pH value of this solution is adjusted to less than 3 by the sulphuric acid being about 10% by concentration, is repeatedly washed by precipitate distilled water, is centrifuged to the aobvious neutrality of supernatant after recentrifuge, and last precipitate is freeze-dried obtains lignin 0.505g.
With comparison example 1 used by [Bmim] Cl ionic liquid phase ratio of outsourcing, the method for the present invention adopts homemade eutectic ionic liquid, and its cost of material is cheap, and preparation technology is simple, and the treatment conditions for the extraction process of rice straw powder lignin are gentle.If embodiments of the invention 2 are compared with comparison example 1, treatment conditions are identical, and the extraction ratio of its lignin is higher.Embodiments of the invention 5 are compared with comparison example 1, and when the extraction ratio of lignin is identical, Extracting temperature can reduce by 30 DEG C, significantly reduces energy resource consumption.
Claims (6)
1. the method for an eutectic ionic liquid separation and Extraction straw lignin, it is characterized in that, powder of straw raw material is added in normal pressure reactor with eutectic ionic liquid by certain mass ratio, mix at 110 DEG C～160 DEG C, after stirring reaction a period of time, the pH value of this mixture is adjusted to about 11 by the sodium hydroxide solution being about 10% by concentration, high speed centrifugation, retains upper solution.The pH value of this solution is adjusted to less than 3 by the sulphuric acid being about 10% by concentration, is repeatedly washed by precipitate distilled water, is centrifuged to the aobvious neutrality of supernatant after recentrifuge, and last precipitate is freeze-dried obtains lignin.
2. the method for eutectic ionic liquid separation and Extraction straw lignin according to claim 1, it is characterised in that rice straw powder is after size-reduced for dried rice straw, ball milling, screening, will to take the powder of 40 order～100 orders, be dried to over dry.
3. the method for eutectic ionic liquid separation and Extraction straw lignin according to claim 1, it is characterized in that eutectic ionic liquid is choline chloride system eutectic ionic liquid, be with choline chloride respectively with carbamide, glycerol, citric acid etc. for raw material at the temperate condition of 70～100 DEG C down to the transparent obtained ionic liquid of reactant liquor.
4. the method for eutectic ionic liquid separation and Extraction straw lignin according to claim 2, it is characterised in that the ratio of choline chloride and the amount of substance of carbamide is 1: 1～1: 3, the ratio of choline chloride and the amount of substance of glycerol is 1: 1～1: 2, the ratio of choline chloride and the amount of substance of citric acid is 1: 1～3: 1.
5. the method for eutectic ionic liquid separation and Extraction straw lignin according to claim 1, it is characterised in that the mass ratio of eutectic ionic liquid and over dry rice straw powder is 100: 5～20.
6. the method for eutectic ionic liquid separation and Extraction straw lignin according to claim 1, it is characterised in that the response time is 1h～10h.
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107474261A (en) * | 2017-09-25 | 2017-12-15 | 南京工业大学 | A kind of method that biomass lignin is extracted using quaternary ammonium base |
| CN107904266A (en) * | 2017-12-18 | 2018-04-13 | 湘潭大学 | A kind of efficient green improves preprocess method and the application of lignocellulosic enzymolysis saccharification efficiency |
| CN108299517A (en) * | 2018-03-07 | 2018-07-20 | 齐鲁工业大学 | A method of extracting low-molecular weight lignin from biomass |
| CN108441530A (en) * | 2018-03-13 | 2018-08-24 | 北京化工大学 | A method of utilizing alkaline eutectic solvent preprocessing lignocellulose |
| CN108554450A (en) * | 2018-06-13 | 2018-09-21 | 青岛科技大学 | The catalyst and method of alcoholysis makrolon |
| CN109485041A (en) * | 2018-11-27 | 2019-03-19 | 南京林业大学 | A kind of method that eutectic ionic liquid prepares porous carbon as pore creating material |
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| CN110218335A (en) * | 2019-05-22 | 2019-09-10 | 广东工业大学 | A method of utilizing ternary depth congruent melting solvent extraction lignin |
| CN110804893A (en) * | 2019-11-15 | 2020-02-18 | 齐鲁工业大学 | Method for separating holocellulose in wood fibers by using choline eutectic solvent |
| CN111302910A (en) * | 2020-03-13 | 2020-06-19 | 中国科学院广州能源研究所 | Method for producing acetophenone and acetic acid by biomass directional catalysis |
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| CN113755542A (en) * | 2021-10-25 | 2021-12-07 | 中南林业科技大学 | Method for pretreating biomass by using eutectic solvent and dioxane |
| CN114377717A (en) * | 2022-01-26 | 2022-04-22 | 福建农林大学 | Lignin-based carbon composite graphite phase carbon nitride/Mxene heterojunction photocatalyst and preparation method and application thereof |
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| CN115232176A (en) * | 2022-07-14 | 2022-10-25 | 华南理工大学 | Method for extracting lignin by using ternary eutectic solvent |
| CN116144039A (en) * | 2022-11-30 | 2023-05-23 | 东北林业大学 | Method for separating natural lignin |
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Cited By (22)
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| CN107474261A (en) * | 2017-09-25 | 2017-12-15 | 南京工业大学 | A kind of method that biomass lignin is extracted using quaternary ammonium base |
| CN107904266A (en) * | 2017-12-18 | 2018-04-13 | 湘潭大学 | A kind of efficient green improves preprocess method and the application of lignocellulosic enzymolysis saccharification efficiency |
| CN108299517A (en) * | 2018-03-07 | 2018-07-20 | 齐鲁工业大学 | A method of extracting low-molecular weight lignin from biomass |
| CN108441530A (en) * | 2018-03-13 | 2018-08-24 | 北京化工大学 | A method of utilizing alkaline eutectic solvent preprocessing lignocellulose |
| CN108554450B (en) * | 2018-06-13 | 2020-03-31 | 青岛科技大学 | Catalyst and process for alcoholysis of polycarbonate |
| CN108554450A (en) * | 2018-06-13 | 2018-09-21 | 青岛科技大学 | The catalyst and method of alcoholysis makrolon |
| CN109485041A (en) * | 2018-11-27 | 2019-03-19 | 南京林业大学 | A kind of method that eutectic ionic liquid prepares porous carbon as pore creating material |
| CN109485041B (en) * | 2018-11-27 | 2022-05-27 | 南京林业大学 | Method for preparing porous carbon by taking eutectic ionic liquid as pore-forming agent |
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| CN109944108B (en) * | 2019-04-08 | 2022-01-28 | 台州浩展婴儿用品股份有限公司 | High-value utilization method for waste cotton fabric |
| CN110218335A (en) * | 2019-05-22 | 2019-09-10 | 广东工业大学 | A method of utilizing ternary depth congruent melting solvent extraction lignin |
| CN110804893A (en) * | 2019-11-15 | 2020-02-18 | 齐鲁工业大学 | Method for separating holocellulose in wood fibers by using choline eutectic solvent |
| CN110804893B (en) * | 2019-11-15 | 2021-11-30 | 齐鲁工业大学 | Method for separating holocellulose in wood fibers by using choline eutectic solvent |
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| CN113603899A (en) * | 2021-07-12 | 2021-11-05 | 华南理工大学 | Method for pretreating lignocellulose by using Lewis base to assist neutral eutectic solvent |
| CN113755542A (en) * | 2021-10-25 | 2021-12-07 | 中南林业科技大学 | Method for pretreating biomass by using eutectic solvent and dioxane |
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| CN114377717B (en) * | 2022-01-26 | 2023-12-22 | 福建农林大学 | Lignin-based carbon composite graphite phase carbon nitride/Mxene heterojunction photocatalyst and preparation method and application thereof |
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| CN115232176A (en) * | 2022-07-14 | 2022-10-25 | 华南理工大学 | Method for extracting lignin by using ternary eutectic solvent |
| CN116144039A (en) * | 2022-11-30 | 2023-05-23 | 东北林业大学 | Method for separating natural lignin |
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Application publication date: 20160713 Assignee: Nanjing Cheng Shan Technology Co., Ltd. Assignor: Nanjing Forestry University Contract record no.: X2019320000341 Denomination of invention: Method for separating and extracting straw lignin by using eutectic ionic liquid Granted publication date: 20180928 License type: Common License Record date: 20191211 Application publication date: 20160713 Assignee: Nanjing Mai Wen environmental protection equipment Engineering Co., Ltd. Assignor: Nanjing Forestry University Contract record no.: X2019320000342 Denomination of invention: Method for separating and extracting straw lignin by using eutectic ionic liquid Granted publication date: 20180928 License type: Common License Record date: 20191211 |
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