CN108641095B - Application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution - Google Patents
Application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution Download PDFInfo
- Publication number
- CN108641095B CN108641095B CN201810436661.7A CN201810436661A CN108641095B CN 108641095 B CN108641095 B CN 108641095B CN 201810436661 A CN201810436661 A CN 201810436661A CN 108641095 B CN108641095 B CN 108641095B
- Authority
- CN
- China
- Prior art keywords
- lignin
- carboxylate
- tetrabutylammonium
- tetrabutylphosphonium
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compounds Of Unknown Constitution (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention relates to the technical field of lignin dissolution, and particularly relates to application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution. The tetrabutyl quaternary phosphonium carboxylate is at least one of tetrabutyl ammonium carboxylate and tetrabutyl phosphonium carboxylate; wherein the structural formula of the tetrabutylammonium carboxylate is shown as a formula I, and the structural formula of the tetrabutylphosphonium carboxylate is shown as a formula II; the invention also provides a lignin solvent containing the tetrabutyl quaternary phosphonium carboxylate, which has low cost, environmental protection and no corrosiveness, can efficiently dissolve lignin at normal temperature, is easy to recover and recycle, has no pollutant discharge, does not need corrosion-resistant equipment, does not need a heating device or high-pressure-resistant equipment, saves raw materials and energy, has low investment cost and strong practicability, and is easy to realize industrial popularization.
Description
Technical Field
The invention relates to the technical field of lignin dissolution, and particularly relates to application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution.
Background
The lignin is one of main components forming a plant skeleton, is regenerated by an ecological cycle chain of plants by about 500 hundred million tons every year all over the world, is the second most renewable and biodegradable resource which is second to the lignin in the nature, and is the only environment-friendly aromatic natural high molecular compound in the nature. Lignin can be used as an important chemical raw material.
However, lignin is far from being fully utilized in the chemical industry, mainly because the existing processes such as lignin separation and extraction are complicated, high in cost or serious in pollution. At present, lignin, which is generally a byproduct of the wood hydrolysis industry and the paper industry, becomes an environmental pollutant because of insufficient utilization. Methods for separating and extracting lignin have been reported as an alkaline method, a sulfite method, an organic solvent method, a thermomechanical method, and the like (chem. rev.2010,110, 3552). Among them, the organosolv method is considered as the best technique for separating lignin. However, the lignin isolated by this method has a low molecular weight, high and unstable activity, and is often operated at high temperature and high pressure, and therefore, high temperature and high pressure resistant equipment is required.
In recent years, ionic liquids have achieved important research results in the research of separation and extraction of lignin (j.wood chem.technol.2007, 27: 23; Green chem.2009,11,339; biotechnol.bioengineerer.2009, 102,1368; j.agric.food chem.2010,58,2915; Green chem.2011,13,3255; Green chem.2011,13,3124; j.chem.technol.biotechnol.2013, 88,1248; aust.j.chem.2012,65,1465). However, ionic liquids have the disadvantages of high price, high viscosity and high temperature for separating lignin, thereby causing the mechanical strength and cost of a mechanical stirring device to be increased.
Disclosure of Invention
In order to overcome the defects and shortcomings of the prior art, the invention provides an application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution, wherein the tetrabutyl quaternary phosphonium carboxylate can be used for dissolving lignin, is green and environment-friendly, has no corrosivity, can be biologically degraded, and does not pollute the environment.
The lignin solvent is low in cost, green, environment-friendly and non-corrosive, lignin can be efficiently dissolved at normal temperature, the solvent is easy to recover and recycle, no pollutant is discharged, corrosion-resistant equipment is not needed, a heating device or high-pressure-resistant equipment is not needed, raw materials and energy are saved, the investment cost is low, the practicability is high, and industrial popularization is easy to realize.
The purpose of the invention is realized by the following technical scheme:
the application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution, wherein the tetrabutyl quaternary phosphonium carboxylate is at least one of tetrabutyl ammonium carboxylate and tetrabutyl phosphonium carboxylate; wherein the structural formula of the tetrabutylammonium carboxylate is shown as a formula I, and the structural formula of the tetrabutylphosphonium carboxylate is shown as a formula II;
wherein R is1Is formate, acetate, butyrate, hexanoate, R2Is acetate, propionate, butyrate or hexanoate;
the preparation method of the tetrabutyl quaternary phosphonium carboxylate comprises the following steps:
adding carboxylic acid into tetrabutyl quaternary phosphonium hydroxide aqueous solution, and stirring for reaction; then removing impurities to obtain tetrabutyl quaternary phosphonium carboxylate;
the carboxylic acid is preferably at least one of formic acid, acetic acid, propionic acid, butyric acid and caproic acid;
the molar ratio of carboxylic acid to tetrabutylphosphonium hydroxide is preferably 1: 1;
the mass fraction of the tetrabutylphosphonium hydroxide aqueous solution is preferably 40%;
the adding mode is preferably dropwise adding;
the stirring reaction condition is preferably 20-30 ℃ and stirring for 8-10 h;
the mode of removing impurities is preferably as follows:
removing most of water by rotary evaporation at the temperature of 60-70 ℃, and finally drying in a vacuum drying oven for 8-48 h;
the mode of removing impurities is further preferably:
removing most of water by rotary evaporation at 60 ℃, and then drying for 24 hours at 60 ℃;
a lignin solvent comprising the tetrabutyl quaternary phosphonium carboxylate described above;
the lignin solvent further comprises water; wherein, when the lignin solvent comprises water and tetrabutylammonium carboxylate, the molar ratio of tetrabutylammonium carboxylate to water is preferably 1: (3-25); when the lignin solvent comprises water and tetrabutyl phosphonium carboxylate, the mass percentage of the water is 30-60%;
the preparation method of the lignin solvent comprises the following steps:
mixing tetrabutyl quaternary phosphonium carboxylate with water, and uniformly stirring to obtain a lignin solvent;
the concrete operation mode of the mixing is preferably as follows:
adding water into tetrabutyl quaternary phosphonium carboxylate, and uniformly stirring to obtain a lignin solvent;
the application of the lignin solvent in the field of lignin dissolution;
the application of the lignin solvent in the field of lignin dissolution comprises the following steps:
mixing lignin and a lignin solvent at the temperature of 20-40 ℃, and uniformly stirring to obtain a lignin solution;
the mixing temperature is preferably 25 ℃;
the solubility of the lignin solution is preferably not less than 3;
the solubility of the lignin solution is further preferably > 65;
the lignin is preferably at least one of Kraft lignin, enzymatic lignin, organic lignin and alkali lignin;
compared with the prior art, the invention has the following advantages and effects:
(1) the invention provides an application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution, and the compound can be used for dissolving lignin, is green and environment-friendly, has no corrosivity, and can be efficiently recovered and recycled.
(2) The lignin solvent provided by the invention has mild preparation conditions and stable solvent performance, and does not need special safety technical investment, so that the requirements on operation equipment can be greatly reduced, high-pressure resistant equipment is not needed, the production investment is less, and the cost is low.
(3) The lignin solvent provided by the invention can be used for preparing the lignin solution at room temperature, and does not need to be frozen or heated, so that heating equipment, freezing equipment or high-pressure-resistant equipment is not needed, the energy is saved, and the equipment investment is reduced.
(4) The lignin solvent provided by the invention has high solubility of lignin at room temperature, for example, at 25 ℃, the molar ratio of water to tetrabutylammonium carboxylate is 4: 1, and a lignin solution having a solubility of more than 60 in a lignin solvent having a water content of 30% (tetrabutyl phosphonium carboxylate). Furthermore, the lignin solvent of the present invention has no dissolution side reaction when dissolving lignin.
(5) The lignin solvent provided by the invention has stable performance and no corrosiveness, can be recycled (for example, ethanol is added into tetrabutyl quaternary phosphonium carboxylate/water/lignin solution, lignin is precipitated and separated out, water and ethanol in the tetrabutyl quaternary phosphonium carboxylate/water/ethanol solution are removed by rotary evaporation, and the tetrabutyl quaternary phosphonium carboxylate can be recycled), has no pollutant discharge, does not need corrosion-resistant equipment, can save raw materials, has low investment cost and strong practicability, and is easy to realize industrial popularization.
Drawings
FIG. 1 is a NMR spectrum of tetrabutylammonium acetate.
FIG. 2 is a NMR spectrum of tetrabutylammonium butyrate.
FIG. 3 is a NMR spectrum of tetrabutylammonium hexanoate.
FIG. 4 is a NMR spectrum of tetrabutylphosphonium acetate.
FIG. 5 is a NMR spectrum of tetrabutylphosphonium propionate.
FIG. 6 is a NMR spectrum of tetrabutylphosphonium butyrate.
FIG. 7 is a NMR chart of tetrabutylphosphonium hexanoate.
FIG. 8 is an infrared spectrum of regenerated lignin and enzymatic hydrolyzed lignin as a raw material in example 4.
FIG. 9 is an infrared spectrum of the regenerated lignin and the enzymatically hydrolyzed lignin of the feedstock in example 8.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
In the examples, the raw materials are all purchased from the market;
example 1
(1) Dropwise adding acetic acid into a tetrabutylammonium hydroxide aqueous solution with the mass fraction of 40%, wherein the molar ratio of the acetic acid to the tetrabutylammonium hydroxide is 1: 1; after the dropwise addition of the acetic acid is finished, stirring and reacting for 10 hours at 20 ℃; then, performing rotary evaporation at 60 ℃ to remove most of water, and finally putting the solution into a vacuum drying oven to be dried for 24 hours at 60 ℃ to obtain tetrabutylammonium acetate; wherein, FIG. 1 is the hydrogen nuclear magnetic diagram of tetrabutylammonium acetate.
(2) Adding water into tetrabutyl ammonium acetate according to the molar ratio of 25 to the tetrabutyl ammonium acetate, and uniformly stirring to obtain a lignin solvent;
(3) at 30 ℃, 49g of Kraft lignin is taken and put into a container, then 100g of lignin solvent is added, and stirring is carried out, thus obtaining a Kraft lignin solution with the solubility of 49.
Example 2
(1) Dropwise adding butyric acid into a tetrabutylammonium hydroxide aqueous solution with the mass fraction of 40%, wherein the molar ratio of the butyric acid to the tetrabutylammonium hydroxide is 1: 1; after the dropwise addition of the butyric acid is finished, stirring and reacting for 8 hours at 30 ℃; then, performing rotary evaporation at 70 ℃ to remove most of water, and finally putting the product into a vacuum drying oven to dry for 8 hours at 70 ℃ to obtain tetrabutyl ammonium butyrate; wherein FIG. 2 is a hydrogen nuclear magnetic map of tetrabutylammonium butyrate.
(2) Adding water into tetrabutyl ammonium butyrate according to the molar ratio of 4 to the tetrabutyl ammonium butyrate, and uniformly stirring to obtain a lignin solvent;
(3) at 25 ℃, 60g of alkali lignin is taken and placed in a container, then 100g of lignin solvent is added, and after stirring, alkali lignin solution with the solubility of 60 is obtained.
Example 3
(1) Adding hexanoic acid dropwise into a tetrabutylammonium hydroxide aqueous solution with the mass fraction of 40%, wherein the molar ratio of the hexanoic acid to the tetrabutylammonium hydroxide is 1: 1; after the addition of the caproic acid is finished, stirring and reacting for 9.5 hours at 25 ℃; then, performing rotary evaporation at 65 ℃ to remove most of water, and finally putting the solution into a vacuum drying oven to be dried for 48 hours at 65 ℃ to obtain tetrabutylammonium caproate; wherein, FIG. 3 is the hydrogen nuclear magnetic spectrum of tetrabutyl ammonium caproate.
(2) Adding water into tetrabutyl ammonium caproate according to the mol ratio of 3 to the tetrabutyl ammonium caproate, and uniformly stirring to obtain a lignin solvent;
(3) at the temperature of 20 ℃, 60g of enzymatic hydrolysis lignin is put into a container, then 100g of lignin solvent is added, and after stirring, an enzymatic hydrolysis lignin solution with the solubility of 60 is obtained.
Example 4
(1) Dropwise adding butyric acid into a tetrabutylammonium hydroxide aqueous solution with the mass fraction of 40%, wherein the molar ratio of the butyric acid to the tetrabutylammonium hydroxide is 1: 1; after the dropwise addition of the butyric acid is finished, stirring and reacting for 10 hours at 25 ℃; then, performing rotary evaporation at 60 ℃ to remove most of water, and finally putting the product into a vacuum drying oven to dry for 24 hours at 60 ℃ to obtain tetrabutylammonium butyrate;
(2) adding water into tetrabutyl ammonium butyrate according to the molar ratio of the water to the tetrabutyl ammonium butyrate of 6, and uniformly stirring to obtain a lignin solvent;
(3) placing 20g of enzymatic hydrolysis lignin in a container at 40 ℃, then adding 40g of lignin solvent, and stirring to obtain an enzymatic hydrolysis lignin solution;
(4) adding ethanol into the enzymatic hydrolysis lignin solution prepared in the step (3), stirring, precipitating lignin, and filtering to obtain lignin; the lignin obtained by filtering is washed by ethanol for 3 times and then dried in the air to obtain the regenerated lignin.
The infrared spectrogram of the regenerated lignin and the raw material enzymatic hydrolysis lignin is shown in figure 8. The infrared spectra of the regenerated lignin and the raw material enzymatic hydrolysis lignin are almost the same, which shows that no chemical reaction occurs between the lignin solvent and the lignin in the lignin dissolving process, and the structure of the regenerated lignin is almost not damaged.
Example 5
(1) Dropwise adding acetic acid into a tetrabutyl phosphonium hydroxide aqueous solution with the mass fraction of 40%, wherein the molar ratio of the acetic acid to the tetrabutyl phosphonium hydroxide is 1: 1; after the dropwise addition of the acetic acid is finished, stirring and reacting for 10 hours at 20 ℃; then, performing rotary evaporation at 60 ℃ to remove most of water, and finally putting the product into a vacuum drying oven to be dried for 24 hours at 60 ℃ to obtain tetrabutyl phosphonium acetate; wherein FIG. 4 is a NMR spectrum of tetrabutylphosphonium acetate.
(2) Adding water into the tetrabutyl phosphonium acetate prepared in the step (1), and uniformly stirring to obtain a lignin solvent, wherein the mass percentage of water in the lignin solvent is 60%;
(3) and (3) at the temperature of 28 ℃, putting 49g of Kraft lignin into a container, adding 100g of the lignin solvent prepared in the step (2), and stirring to obtain a Kraft lignin solution with the solubility of 49.
Example 6
(1) Dropwise adding propionic acid into a tetrabutyl phosphonium hydroxide aqueous solution with the mass fraction of 40%, wherein the molar ratio of the propionic acid to the tetrabutyl phosphonium hydroxide is 1: 1; after the propionic acid is dripped, stirring and reacting for 8 hours at the temperature of 30 ℃; then, performing rotary evaporation at 70 ℃ to remove most of water, and finally putting the product into a vacuum drying oven to be dried for 8 hours at 70 ℃ to obtain tetrabutyl phosphonium propionate; wherein FIG. 5 is a NMR spectrum of tetrabutylphosphonium propionate.
(2) Adding water into the tetrabutyl phosphonium propionate prepared in the step (1), and uniformly stirring to obtain a lignin solvent, wherein the mass percentage of the water in the lignin solvent is 30%;
(3) and (3) placing 65g of alkali lignin solvent into a container at 25 ℃, then adding 100g of the lignin solvent prepared in the step (2), and stirring to obtain an alkali lignin solution with the solubility of more than 65.
Example 7
(1) Dropwise adding butyric acid into a tetrabutyl phosphonium hydroxide aqueous solution with the mass fraction of 40%, wherein the molar ratio of the butyric acid to the tetrabutyl phosphonium hydroxide is 1: 1; after the dropwise addition of the butyric acid is finished, stirring and reacting for 9 hours at 25 ℃; then, performing rotary evaporation at 65 ℃ to remove most of water, and finally putting the product into a vacuum drying oven to be dried for 48 hours at 65 ℃ to obtain tetrabutyl phosphonium butyrate; wherein FIG. 6 is a NMR spectrum of tetrabutylphosphonium butyrate.
(2) Adding water into the tetrabutyl phosphonium butyrate prepared in the step (1), and uniformly stirring to obtain a lignin solvent, wherein the mass percent of water in the lignin solvent is 35%;
(3) and (3) placing 70g of enzymatic hydrolysis lignin into a container at 25 ℃, then adding 100g of lignin solvent prepared in the step (2), and stirring to obtain an enzymatic hydrolysis lignin solution with the solubility of more than 70.
Example 8
(1) Adding hexanoic acid dropwise into a tetrabutyl phosphonium hydroxide aqueous solution with the mass fraction of 40%, wherein the molar ratio of the hexanoic acid to the tetrabutyl phosphonium hydroxide is 1: 1; after the addition of the caproic acid is finished, stirring and reacting for 9 hours at 25 ℃; then, performing rotary evaporation at 65 ℃ to remove most of water, and finally putting the solution into a vacuum drying oven to be dried for 48 hours at 65 ℃ to obtain tetrabutyl phosphonium caproate; wherein, FIG. 7 is the NMR spectrum of tetrabutyl phosphonium caproate.
(2) Adding water into the tetrabutyl phosphonium caproate prepared in the step (1), and uniformly stirring to obtain a lignin solvent, wherein the mass percent of water in the lignin solvent is 45%;
(3) putting 5g of wood Kraft lignin into a container, adding 10g of the lignin solvent prepared in the step (2), and stirring to obtain a Kraft lignin solution;
(4) adding ethanol into the Kraft lignin solution prepared in the step (3) at 25 ℃, stirring, precipitating and separating out lignin, and filtering to obtain lignin; washing lignin with ethanol for 3 times, and drying in air to obtain regenerated lignin;
the infrared images of the regenerated lignin and the raw material lignin are shown in figure 9. The infrared spectra of the regenerated lignin and the raw material lignin are almost the same, which shows that the water/tetrabutyl phosphonium acetate solvent and the lignin do not have chemical reaction in the lignin dissolving process, and the structure of the regenerated lignin is hardly damaged.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (9)
1. Use of tetrabutylammonium carboxylate or/and tetrabutylphosphonium carboxylate in lignin dissolution, characterized in that: the structural formula of the tetrabutylammonium carboxylate is shown as a formula I, and the structural formula of the tetrabutylphosphonium carboxylate is shown as a formula II;
wherein R is1Is formate, butyrate or hexanoate, R2Is acetate, propionate, butyrate or hexanoate;
the application comprises the following steps:
(1) mixing tetrabutylammonium carboxylate or/and tetrabutylphosphonium carboxylate with water, and uniformly stirring to obtain a lignin solvent; wherein, when the lignin solvent comprises water and tetrabutylammonium carboxylate, the molar ratio of tetrabutylammonium carboxylate to water is 1: (3-25); when the lignin solvent comprises water and tetrabutyl phosphonium carboxylate, the mass percentage of the water is 30-60%;
(2) and (3) mixing the lignin and the lignin solvent at the temperature of 20-40 ℃, and uniformly stirring to obtain a lignin solution.
2. Use of tetrabutylammonium carboxylate or/and tetrabutylphosphonium carboxylate according to claim 1 in the dissolution of lignin, characterized in that:
the preparation method of the tetrabutylammonium carboxylate or/and the tetrabutylphosphonium carboxylate comprises the following steps:
adding carboxylic acid into tetrabutylammonium hydroxide aqueous solution or tetrabutylphosphonium hydroxide aqueous solution, and stirring for reaction; then removing impurities to obtain tetrabutylammonium carboxylate or tetrabutylphosphonium carboxylate.
3. Use of tetrabutylammonium carboxylate or/and tetrabutylphosphonium carboxylate according to claim 2 in the dissolution of lignin, characterized in that:
the molar ratio of the carboxylic acid to the tetrabutylammonium hydroxide or the tetrabutylphosphonium hydroxide is 1: 1.
4. use of tetrabutylammonium carboxylate or/and tetrabutylphosphonium carboxylate according to claim 2 in the dissolution of lignin, characterized in that:
the mass fraction of the tetrabutylammonium hydroxide aqueous solution or the tetrabutylphosphonium hydroxide aqueous solution is 40%.
5. Use of tetrabutylammonium carboxylate or/and tetrabutylphosphonium carboxylate according to claim 2 in the dissolution of lignin, characterized in that:
the stirring reaction condition is that the mixture is stirred for 8-10 hours at the temperature of 20-30 ℃.
6. A lignin solvent characterized by comprising tetrabutylammonium carboxylate or/and tetrabutylphosphonium carboxylate as described in claim 1 and water; wherein, when the lignin solvent comprises water and tetrabutylammonium carboxylate, the molar ratio of tetrabutylammonium carboxylate to water is 1: (3-25); when the lignin solvent comprises water and tetrabutyl phosphonium carboxylate, the mass percentage of the water is 30-60%.
7. The method for producing a lignin solvent according to claim 6, characterized by comprising the steps of:
and (3) mixing tetrabutylammonium carboxylate or/and tetrabutylphosphonium carboxylate with water, and uniformly stirring to obtain the lignin solvent.
8. Use of the lignin solvent according to claim 6 in the field of lignin dissolution.
9. Use of the lignin solvent according to claim 8 in the field of lignin dissolution, characterized by comprising the steps of:
and (3) mixing the lignin and the lignin solvent at the temperature of 20-40 ℃, and uniformly stirring to obtain a lignin solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810436661.7A CN108641095B (en) | 2018-05-09 | 2018-05-09 | Application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810436661.7A CN108641095B (en) | 2018-05-09 | 2018-05-09 | Application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108641095A CN108641095A (en) | 2018-10-12 |
| CN108641095B true CN108641095B (en) | 2021-04-13 |
Family
ID=63753948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810436661.7A Active CN108641095B (en) | 2018-05-09 | 2018-05-09 | Application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108641095B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103773054A (en) * | 2013-12-26 | 2014-05-07 | 南京林业大学 | Preparation method of wood fiber bio-based plastic |
-
2018
- 2018-05-09 CN CN201810436661.7A patent/CN108641095B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103773054A (en) * | 2013-12-26 | 2014-05-07 | 南京林业大学 | Preparation method of wood fiber bio-based plastic |
Non-Patent Citations (4)
| Title |
|---|
| Jiaojiao Miao等.Partial delignification of wood and membrane preparation using a quaternary ammonium ionic liquid.《SCIENTIFIC REPORTS》.2017,第7卷 * |
| Jiaojiao Miao等.Partial delignification of wood and membrane preparation using a quaternary ammonium ionic liquid.《SCIENTIFIC REPORTS》.2017,第7卷第1-12页. * |
| 李文婷.木质素在离子液体中溶解及改性的研究进展.《广州化工》.2015,第43卷(第10期), * |
| 闫冰.咪唑类离子液体水体系处理木质素的研究.《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》.2017,第7页和18页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108641095A (en) | 2018-10-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110804893B (en) | Method for separating holocellulose in wood fibers by using choline eutectic solvent | |
| CN110540508B (en) | Eutectic solvent and application thereof in extracting lignin | |
| TWI610935B (en) | Method for producing lignin decomposition product | |
| US8900369B2 (en) | Method and apparatus for lignocellulose pretreatment using a super-cellulose-solvent and highly volatile solvents | |
| CN102864672B (en) | Method for extracting lignin | |
| UA105365C2 (en) | Process for the production of sugars from biomass | |
| CN109180838B (en) | Method for fractionating lignocellulose biomass components by two-phase molten salt system | |
| CN101429100B (en) | Chemical recovery method for waste polycarbonate material in ionic liquid surrounding | |
| CN103748231A (en) | Method for producing ethanol using cellulosic biomass as starting material | |
| CN114085876A (en) | Method for comprehensively utilizing lignocellulose by using polyol-based acidic eutectic solvent | |
| US9969760B2 (en) | Method for lignin recovery | |
| CN109797592B (en) | Method for separating wheat straw components by catalyzing thermal decomposition of ethanol solvent | |
| CA2717995C (en) | A method of producing bioethanol from lignocellulose biomass | |
| CN108641095B (en) | Application of tetrabutyl quaternary phosphonium carboxylate in lignin dissolution | |
| CN112029115B (en) | Method for separating and extracting lignin by in-situ synthesis of deep eutectic solvent | |
| CN109182308B (en) | Method for recovering cellulase by using pH response type lignin-based polyether | |
| CN218596229U (en) | Device for extracting butyl glycolate from organic wastewater | |
| JP6274478B2 (en) | Method for producing lignin degradation product | |
| CN114105739B (en) | Green alkali lignin micromolecule separation method and product | |
| CN102796048A (en) | Preparation method of ionic liquid for efficiently extracting cellulose and application thereof | |
| CN108383792B (en) | Diallyl imidazole methoxyacetate, lignin solvent, preparation and application | |
| CN108892784B (en) | Green and environment-friendly method for purifying enzymatic hydrolysis lignin | |
| CN113186747A (en) | Method for producing bamboo dissolving pulp and high-purity xylan by using bamboo pulp as raw material | |
| CN115819380B (en) | Neutral gas explosion-SO3Method for preparing furfural by catalyzing corn cob through ultrasonic coupling pretreatment | |
| CN109336774B (en) | Synthesis method and application of functionalized bio-based ionic liquid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |