CN113563604A - Method for regulating and controlling industrial alkali lignin molecules - Google Patents
Method for regulating and controlling industrial alkali lignin molecules Download PDFInfo
- Publication number
- CN113563604A CN113563604A CN202110820850.6A CN202110820850A CN113563604A CN 113563604 A CN113563604 A CN 113563604A CN 202110820850 A CN202110820850 A CN 202110820850A CN 113563604 A CN113563604 A CN 113563604A
- Authority
- CN
- China
- Prior art keywords
- alkali lignin
- dibromohexane
- lignin
- regulating
- precipitate
- 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.)
- Granted
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)
Abstract
The invention belongs to the field of alkali lignin utilization in pulping and papermaking industries, and relates to a method for regulating and controlling industrial alkali lignin molecules, which comprises the following steps: alkali lignin in pulping and papermaking industry is used as a raw material, and the alkali lignin is purified by an organic solvent and an acid precipitation method. The purified alkali lignin reacts in a 1, 6-dibromohexane/dimethylformamide/potassium carbonate system to obtain the alkali lignin regulated and controlled by molecules. The novel technology developed by the application improves the molecular weight of the alkali lignin, reduces the polydispersity of partial fractions, regulates the content of phenolic hydroxyl groups, changes the color depth of the alkali lignin and lays a foundation for subsequent modification and application of the alkali lignin. By controlling the adding amount, the reaction time and the temperature of the 1, 6-dibromohexane, the molecular weight of the alkali lignin can be improved by 353-1643 percent, the polydispersity of partial fractions is reduced, the content of the phenolic hydroxyl group is regulated and controlled to be reduced by 2-80 percent, and the color of the alkali lignin can be changed.
Description
Technical Field
The invention belongs to the field of alkali lignin utilization in the pulping and papermaking industry, and particularly relates to a method for regulating and controlling the molecular weight and main functional groups of alkali lignin.
Background
Lignin is a generic term for a class of substances with common properties found in woody, herbaceous and all vascular plants, the second largest biomass resource in the plant kingdom that reserves only second to cellulose. Meanwhile, the lignin is the only reproducible aromatic polymer compound, can be used for preparing resin materials and functional polymer materials, and plays an important role in the fields of oil exploitation, building concrete water reduction, printing and dyeing dye dispersion, pesticide slow-release dispersion, fertilizer slow release and the like. Currently only about 2% of lignin is used for the production of high value added products, most of which are used only as cheap fuels. The lignin is mainly from the pulping and papermaking industry, and as a pulping byproduct, the annual production amount of the lignin is about 5000 ten thousand tons, wherein about 1500 ten thousand tons in China are not separated or utilized, and 95 percent of the lignin is treated in a direct discharge or combustion mode, so that a serious environmental problem is caused. Today, most pulp and paper mills in the world use alkaline pulping, and the lignin produced is mainly alkali lignin. Therefore, the method for producing the alkali lignin-based product with high added value by fully utilizing the alkali lignin resource has more economic, social and ecological significance. The small molecular weight, high polydispersity, low reactivity, etc. of alkali lignin severely limit its applications.
Disclosure of Invention
In order to overcome the problems, the invention uses the alkali lignin in the pulping and papermaking industry as a raw material, adopts a novel alkylation system of 1, 6-dibromohexane/dimethylformamide/potassium carbonate, and has the advantages of efficiently improving the molecular weight of the alkali lignin, adjusting the polydispersity, and adjusting and controlling functional groups such as phenolic hydroxyl groups. By controlling the adding amount, the reaction time and the temperature of the 1, 6-dibromohexane, the molecular weight of the alkali lignin can be improved by 353-1643 percent, the polydispersity of partial fractions is reduced, the content of the phenolic hydroxyl group is regulated and controlled to be reduced by 2-80 percent, and the color of the alkali lignin can be changed.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
in a first aspect of the invention, a method for regulating an industrial alkali lignin molecule is provided, which comprises the following steps:
purifying the industrial alkali lignin to obtain purified alkali lignin;
and (3) carrying out alkylation reaction on the purified alkali lignin in a 1, 6-dibromohexane/dimethylformamide/potassium carbonate system to obtain the alkali lignin regulated and controlled by molecules.
The novel technology developed by the application improves the molecular weight of the alkali lignin, reduces the polydispersity of partial fractions, regulates the content of phenolic hydroxyl groups, changes the color depth of the alkali lignin and lays a foundation for subsequent modification and application of the alkali lignin.
In a second aspect of the invention, there is provided a molecularly imprinted alkali lignin prepared by any of the above methods.
The third aspect of the invention provides the application of the alkali lignin subjected to molecular regulation and control in the fields of preparation of resin materials, functional polymer materials, oil exploitation, water reduction of building concrete, dye dispersion for printing and dyeing, slow-release dispersion of pesticides and slow release of fertilizers.
The invention has the beneficial effects that:
(1) in the whole alkali lignin molecule regulation and control process, the alkali lignin and a novel 1, 6-dibromohexane/dimethylformamide/potassium carbonate alkylation system are purified by adopting an organic solvent and an acid precipitation method, the molecular weight of the alkali lignin can be regulated and controlled according to different application requirements of different alkali lignin, the polydispersity of partial fractions is reduced, the content of phenolic hydroxyl groups is regulated and controlled, the color depth of the alkali lignin is changed, and the alkali lignin molecule regulation and control method has important significance for subsequent modification and application of the alkali lignin.
(2) The operation method is simple, low in cost, high in efficiency, universal and easy for large-scale production.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 shows the color change of alkali lignin before and after the control in example 1 of the present invention.
FIG. 2 shows the color change of alkali lignin before and after the control in example 2 of the present invention.
FIG. 3 shows the color change of alkali lignin before and after the control in example 3 of the present invention.
FIG. 4 shows the color change of alkali lignin before and after the control in example 4 of the present invention.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
A method for regulating and controlling industrial alkali lignin molecules, which takes the pulping and papermaking industrial alkali lignin as a raw material, comprises the following steps:
the dry crude alkali lignin was added to an aqueous acidic dioxane solution (dioxane/water 9: 1, v: v, pH 2). The mixture is stirred for 2-2.5 hours at 87-90 ℃ and then centrifuged to remove the precipitate. Adding the supernatant of the sodium bicarbonate, and keeping stirring for 3-4 hours to neutralize the acid in the solution. After centrifugation again to remove the precipitate, the supernatant was subjected to vacuum rotary evaporation at 55 ℃ to remove and recover dioxane. The supernatant after rotary evaporation in vacuo was added to a hydrochloric acid solution at pH 2, followed by centrifugation to obtain a precipitate. Freeze drying the precipitate to obtain solid powdered Purified Alkali Lignin (PAL). Dissolving PAL in dimethylformamide at a ratio of 1: 20-25. Adding K which is 0.6-08 times of the mass of the purified alkali lignin into the mixed solution2CO3As an acid binder to absorb the acid generated in the reaction, and a trace amount of KI was added as an activator of 1, 6-dibromohexane. Under the protection of nitrogen, heating the mixture to a specified temperature (60-90 ℃), adding 1, 6-dibromohexane, keeping the temperature for reaction for 1-4 hours, and then adding 2mol/L hydrochloric acid aqueous solution to finish the reaction. The reacted alkali lignin was precipitated with aqueous hydrochloric acid (pH 2). Centrifuging to obtain precipitate, washing with hydrochloric acid water solution (pH 2), and freeze drying to obtain solid powder substance, i.e. alkali lignin (CAL) regulated by molecule.
In some embodiments, the alkali lignin is crude alkali lignin, in powder or cake form, isolated from alkaline pulping black liquor.
The chemical reagent grades used in the patent of the invention are all chemically pure.
The invention takes alkali lignin in pulping and papermaking industry as raw material, purifies the alkali lignin by using organic solvent and acid precipitation method, adopts novel alkylation system 1, 6-dibromohexane/dimethylformamide/potassium carbonate to regulate and control alkali lignin molecules, and comprises the following detailed steps:
(1) organic solvent purification of crude alkali lignin: the dry crude alkali lignin was added to an aqueous acidic dioxane solution (dioxane/water 9: 1, v: v, pH 2). The mixture is stirred for 2-2.5 hours at 87-90 ℃ and then centrifuged to remove the precipitate. Adding the supernatant of the sodium bicarbonate, and keeping stirring for 3-4 hours to neutralize the acid in the solution. After centrifugation again to remove the precipitate, the supernatant was subjected to vacuum rotary evaporation at 55 ℃ to remove and recover dioxane.
(2) Acid precipitation, separation and purification of alkali lignin: the supernatant after rotary evaporation in vacuo was added to a hydrochloric acid solution at pH 2, followed by centrifugation to obtain a precipitate. Freeze drying the precipitate to obtain solid powder of Purified Alkali Lignin (PAL).
(3) Alkylation of PAL: dissolving PAL in dimethylformamide at a ratio of 1: 20-25. Adding K which is 0.6-08 times of the mass of the purified alkali lignin into the mixed solution2CO3As an acid binder to absorb the acid generated in the reaction, and a trace amount of KI was added as an activator of 1, 6-dibromohexane. Under the protection of nitrogen, heating the mixture to a specified temperature (60-90 ℃), adding 1, 6-dibromohexane, keeping the temperature for reaction for 1-4 hours, and then adding 2mol/L hydrochloric acid aqueous solution to finish the reaction.
(4) Acid precipitation of CAL: the reacted alkali lignin was precipitated with aqueous hydrochloric acid (pH 2). Centrifuging to obtain precipitate, washing with hydrochloric acid water solution (pH 2), and freeze drying to obtain solid powder substance, i.e. alkali lignin (CAL) regulated by molecule.
The method specifically comprises the following steps:
(1) the dry crude alkali lignin was added to an aqueous acidic dioxane solution (dioxane/water 9: 1, v: v, pH 2). The mixture is stirred for 2-2.5 hours at 87-90 ℃ and then centrifuged to remove the precipitate. Adding the supernatant of the sodium bicarbonate, and keeping stirring for 3-4 hours to neutralize the acid in the solution. After centrifugation again to remove the precipitate, the supernatant was subjected to vacuum rotary evaporation at 55 ℃ to remove and recover dioxane.
(2) Adding the supernatant obtained in the step (1) after vacuum rotary evaporation into a hydrochloric acid solution with the pH value of 2, and then centrifuging to obtain a precipitate. Freeze drying the precipitate to obtain solid powder of Purified Alkali Lignin (PAL).
(3) The PAL in step (2) was dissolved in dimethylformamide in a ratio of 1: 20. Adding K which is 0.6-08 times of the mass of the purified alkali lignin into the mixed solution2CO3As an acid binder to absorb the acid generated in the reaction, and a trace amount of KI was added as an activator of 1, 6-dibromohexane. Under the protection of nitrogen, heating the mixture to a specified temperature (60-90 ℃), adding 1, 6-dibromohexane, keeping the temperature for reaction for 1-4 hours, and then adding 2mol/L hydrochloric acid aqueous solution to finish the reaction.
(4) And (3) precipitating the reacted alkali lignin from the mixture in the step (3) by using hydrochloric acid aqueous solution (pH 2). Centrifuging to obtain precipitate, washing with hydrochloric acid water solution (pH 2), and freeze drying to obtain solid powder substance, i.e. alkali lignin (CAL) regulated by molecule.
The present invention is described in further detail below with reference to specific examples, which are intended to be illustrative of the invention and not limiting.
Example 1: the alkali lignin molecule regulation and control in the pulping and papermaking industry is prepared by the following steps.
(1) Organic solvent purification of crude alkali lignin: to the dried crude alkali lignin was added an aqueous acidic dioxane solution at a ratio of 1:10(w: v) (dioxane/water 9: 1, v: v, pH 2). The mixture was stirred at 87 ℃ for 2 hours and then centrifuged to remove the precipitate. The supernatant solution of sodium bicarbonate was added and kept stirring for 3 hours to neutralize the acid in the solution. After centrifugation again to remove the precipitate, the supernatant was subjected to vacuum rotary evaporation at 55 ℃ to remove and recover dioxane.
(2) Acid precipitation, separation and purification of alkali lignin: the supernatant after rotary evaporation in vacuo was added to 2000mL of hydrochloric acid solution (pH 2), and then centrifuged to obtain a precipitate. Freeze drying the precipitate to obtain solid powder of Purified Alkali Lignin (PAL).
(3) Alkylation of PAL: PAL was dissolved in dimethylformamide in a ratio of 1: 20. Adding K with the mass 0.6 times of that of the purified alkali lignin into the mixed solution2CO3As an acid binder to absorb the acid generated in the reaction, and a trace amount of KI was added as an activator of 1, 6-dibromohexane. Heating the mixture to 70 deg.C under nitrogen protection, and mixing at a ratio of 0.05g/gLignin1, 6-dibromohexane was added, the temperature was maintained, and the reaction was terminated by adding 2mol/L aqueous hydrochloric acid.
(4) Acid precipitation of CAL: the reacted alkali lignin was precipitated with aqueous hydrochloric acid (pH 2). Centrifuging to obtain precipitate, washing with hydrochloric acid water solution (pH 2), and freeze drying to obtain solid powder substance, i.e. molecular Controlled Alkali Lignin (CAL). The resulting CAL molecular weight and phenolic hydroxyl content were varied as shown in Table 1, and the color was varied as shown in FIG. 1.
TABLE 1 variation of alkali lignin molecular weight and phenolic hydroxyl group content before and after control
Example 2: the alkali lignin molecule regulation and control in the pulping and papermaking industry is prepared by the following steps.
(1) Organic solvent purification of crude alkali lignin: to the dried crude alkali lignin was added an aqueous acidic dioxane solution at a ratio of 1:10(w: v) (dioxane/water 9: 1, v: v, pH 2). The mixture was stirred at 87 ℃ for 2 hours and then centrifuged to remove the precipitate. The supernatant solution of sodium bicarbonate was added and kept stirring for 3 hours to neutralize the acid in the solution. After centrifugation again to remove the precipitate, the supernatant was subjected to vacuum rotary evaporation at 55 ℃ to remove and recover dioxane.
(2) Acid precipitation, separation and purification of alkali lignin: the supernatant after rotary evaporation in vacuo was added to 2000mL of hydrochloric acid solution (pH 2), and then centrifuged to obtain a precipitate. Freeze drying the precipitate to obtain solid powder of Purified Alkali Lignin (PAL).
(3)PAAlkylation of L: PAL was dissolved in dimethylformamide in a ratio of 1: 20. Adding K with the mass 0.6 times of that of the purified alkali lignin into the mixed solution2CO3As an acid binder to absorb the acid generated in the reaction, and a trace amount of KI was added as an activator of 1, 6-dibromohexane. Heating the mixture to 70 deg.C under nitrogen protection, and mixing at a ratio of 0.60g/gLignin1, 6-dibromohexane was added, the temperature was maintained, and the reaction was terminated by adding 2mol/L aqueous hydrochloric acid.
(4) Acid precipitation of CAL: the reacted alkali lignin was precipitated with aqueous hydrochloric acid (pH 2). Centrifuging to obtain precipitate, washing with hydrochloric acid water solution (pH 2), and freeze drying to obtain solid powder substance, i.e. molecular Controlled Alkali Lignin (CAL). The resulting CAL molecular weight and phenolic hydroxyl content were varied as shown in Table 2, and the color change was shown in FIG. 2.
TABLE 2 variation of alkali lignin molecular weight and phenolic hydroxyl group content before and after control
Example 3: the alkali lignin molecule regulation and control in the pulping and papermaking industry is prepared by the following steps.
(1) Organic solvent purification of crude alkali lignin: to the dried crude alkali lignin was added an aqueous acidic dioxane solution at a ratio of 1:10(w: v) (dioxane/water 9: 1, v: v, pH 2). The mixture was stirred at 87 ℃ for 2 hours and then centrifuged to remove the precipitate. The supernatant solution of sodium bicarbonate was added and kept stirring for 3 hours to neutralize the acid in the solution. After centrifugation again to remove the precipitate, the supernatant was subjected to vacuum rotary evaporation at 55 ℃ to remove and recover dioxane.
(2) Acid precipitation, separation and purification of alkali lignin: the supernatant after rotary evaporation in vacuo was added to 2000mL of hydrochloric acid solution (pH 2), and then centrifuged to obtain a precipitate. Freeze drying the precipitate to obtain solid powder of Purified Alkali Lignin (PAL).
(3) Alkylation of PAL: PAL was dissolved in dimethylformamide in a ratio of 1: 20. Adding K with the mass 0.6 times of that of the purified alkali lignin into the mixed solution2CO3As an acid binder to absorb the acid generated in the reaction, and a trace amount of KI was added as an activator of 1, 6-dibromohexane. Heating the mixture to 70 deg.C under nitrogen protection, and mixing at a ratio of 0.60g/gLignin1, 6-dibromohexane was added, the temperature was maintained, and the reaction was terminated by adding 2mol/L aqueous hydrochloric acid.
(4) Acid precipitation of CAL: the reacted alkali lignin was precipitated with aqueous hydrochloric acid (pH 2). Centrifuging to obtain precipitate, washing with hydrochloric acid water solution (pH 2), and freeze drying to obtain solid powder substance, i.e. molecular Controlled Alkali Lignin (CAL). The resulting CAL molecular weight and phenolic hydroxyl content were varied as shown in Table 3, and the color was varied as shown in FIG. 3.
TABLE 3 variation of alkali lignin molecular weight and phenolic hydroxyl group content before and after control
Example 4: the alkali lignin molecule regulation and control in the pulping and papermaking industry is prepared by the following steps.
(1) Organic solvent purification of crude alkali lignin: to the dried crude alkali lignin was added an aqueous acidic dioxane solution at a ratio of 1:10(w: v) (dioxane/water 9: 1, v: v, pH 2). The mixture was stirred at 87 ℃ for 2 hours and then centrifuged to remove the precipitate. The supernatant solution of sodium bicarbonate was added and kept stirring for 3 hours to neutralize the acid in the solution. After centrifugation again to remove the precipitate, the supernatant was subjected to vacuum rotary evaporation at 55 ℃ to remove and recover dioxane.
(2) Acid precipitation, separation and purification of alkali lignin: the supernatant after rotary evaporation in vacuo was added to 2000mL of hydrochloric acid solution (pH 2), and then centrifuged to obtain a precipitate. Freeze drying the precipitate to obtain solid powder of Purified Alkali Lignin (PAL).
(3) Alkylation of PAL: PAL was dissolved in dimethylformamide in a ratio of 1: 20. Adding K with the mass 0.6 times of that of the purified alkali lignin into the mixed solution2CO3As an acid binder to absorb the acid generated in the reaction, and a trace amount of KI was added as an activator of 1, 6-dibromohexane. Heating the mixture to 90 deg.C under nitrogen protection, and mixing at a ratio of 0.30g/gLignin1, 6-dibromohexane was added, the temperature was maintained, and the reaction was terminated by adding 2mol/L aqueous hydrochloric acid.
(4) Acid precipitation of CAL: the reacted alkali lignin was precipitated with aqueous hydrochloric acid (pH 2). Centrifuging to obtain precipitate, washing with hydrochloric acid water solution (pH 2), and freeze drying to obtain solid powder substance, i.e. molecular Controlled Alkali Lignin (CAL). The resulting CAL molecular weight and phenolic hydroxyl content were varied as shown in Table 4, and the color change was shown in FIG. 4.
TABLE 4 variation of alkali lignin molecular weight and phenolic hydroxyl content before and after control
It should be noted that the above-mentioned embodiments are only preferred embodiments of the present invention, and the present invention is not limited thereto, and although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications and equivalents can be made in the technical solutions described in the foregoing embodiments, or equivalents thereof. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A method for regulating and controlling industrial alkali lignin molecules is characterized by comprising the following steps:
purifying the industrial alkali lignin to obtain purified alkali lignin;
and (3) carrying out alkylation reaction on the purified alkali lignin in a 1, 6-dibromohexane/dimethylformamide/potassium carbonate system to obtain the alkali lignin regulated and controlled by molecules.
2. The method of claim 1, wherein the purifying comprises: organic solvent purification and acid precipitation purification.
3. The method for regulating and controlling the industrial alkali lignin molecule according to claim 2, wherein the organic solvent purification comprises the following specific steps: the organic solvent purification treatment comprises the following specific steps: adding dried alkali lignin into an acidic dioxane aqueous solution, stirring the mixture at 87-90 ℃ for 2-2.5 hours, and centrifuging to remove precipitates; adding the supernatant of sodium bicarbonate, and keeping stirring for 3-4 hours to neutralize the acid in the solution; after centrifugation again to remove the precipitate, the supernatant was vacuum rotary evaporated to remove and recover dioxane.
4. The method for regulating the industrial alkali lignin molecule according to claim 2, wherein the acid precipitation comprises the following steps: adding the supernatant obtained after purifying the organic solvent into hydrochloric acid solution with the pH value of 2, and then centrifuging to obtain precipitate; freeze drying the precipitate to obtain solid powder of purified alkali lignin.
5. The method for regulating and controlling the industrial alkali lignin molecule according to claim 1, wherein the volume ratio of the purified alkali lignin to the dimethylformamide is 1: 20-25.
6. The method of claim 1, wherein the purification of alkali lignin and K is performed by2CO3The mass ratio of (1): 0.6 to 0.8.
7. The method for regulating the molecular weight of industrial alkali lignin according to claim 1, wherein KI is further added as an activator of 1, 6-dibromohexane in the 1, 6-dibromohexane/dimethylformamide/potassium carbonate system.
8. The method for regulating and controlling the industrial alkali lignin molecule according to claim 1, wherein the alkylation reaction comprises the following specific steps: dissolving the purified alkali lignin in dimethylformamide to obtain a mixed solution; adding K to the mixed solution2CO3As an acid binding agent, adding KI as an activating agent of the 1, 6-dibromohexane; under the protection of nitrogen, heating the mixture to 60-90 ℃, adding 1, 6-dibromohexane, keeping the temperature for reaction for 1-4 hours, and then adding a hydrochloric acid aqueous solution to finish the reaction; precipitating by using a hydrochloric acid aqueous solution; washing the precipitate with hydrochloric acid water solution, and freeze drying to obtain solid powdery substance, i.e. alkali lignin regulated by molecules.
9. A molecularly-modified alkali lignin prepared by the method of any one of claims 1 to 8.
10. The use of the molecularly imprinted alkali lignin of claim 9 in the fields of resin material preparation, functional polymer material preparation, oil exploitation, water reduction of building concrete, dye dispersion in printing and dyeing, slow release dispersion of pesticides, and slow release of fertilizers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110820850.6A CN113563604B (en) | 2021-07-20 | 2021-07-20 | Method for regulating and controlling industrial alkali lignin molecules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110820850.6A CN113563604B (en) | 2021-07-20 | 2021-07-20 | Method for regulating and controlling industrial alkali lignin molecules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113563604A true CN113563604A (en) | 2021-10-29 |
| CN113563604B CN113563604B (en) | 2023-04-18 |
Family
ID=78165796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110820850.6A Active CN113563604B (en) | 2021-07-20 | 2021-07-20 | Method for regulating and controlling industrial alkali lignin molecules |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113563604B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114854040A (en) * | 2022-06-07 | 2022-08-05 | 西南交通大学 | Light-color lignin and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104004200A (en) * | 2014-05-26 | 2014-08-27 | 华南理工大学 | Alkane-bridged lignin-based polymer as well as preparation method and application of lignin-based polymer |
| CN104542583A (en) * | 2015-01-04 | 2015-04-29 | 华南理工大学 | High-effective lignosulfonate pesticide suspension dispersing agent and preparation and applications thereof |
| CN111116936A (en) * | 2020-01-07 | 2020-05-08 | 河南农业大学 | Lignin separation and extraction method based on FeOCl Fenton reaction |
-
2021
- 2021-07-20 CN CN202110820850.6A patent/CN113563604B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104004200A (en) * | 2014-05-26 | 2014-08-27 | 华南理工大学 | Alkane-bridged lignin-based polymer as well as preparation method and application of lignin-based polymer |
| CN104542583A (en) * | 2015-01-04 | 2015-04-29 | 华南理工大学 | High-effective lignosulfonate pesticide suspension dispersing agent and preparation and applications thereof |
| CN111116936A (en) * | 2020-01-07 | 2020-05-08 | 河南农业大学 | Lignin separation and extraction method based on FeOCl Fenton reaction |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114854040A (en) * | 2022-06-07 | 2022-08-05 | 西南交通大学 | Light-color lignin and preparation method and application thereof |
| CN114854040B (en) * | 2022-06-07 | 2023-08-22 | 西南交通大学 | Light-colored lignin and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113563604B (en) | 2023-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Lora | Industrial commercial lignins: sources, properties and applications | |
| CN110734582B (en) | Method and apparatus for producing nanocellulose, and compositions and products produced therefrom | |
| EP2683759B1 (en) | Separation of lignin from plant material | |
| Gao et al. | Sulfonation of hydroxymethylated lignin and its application | |
| CN103131020A (en) | Carboxylic sulfonic-acid-group lignin dye dispersing agent and preparation method thereof | |
| CN110624514B (en) | Method for improving adsorption capacity of humic acid on metal ions | |
| CN113563604B (en) | Method for regulating and controlling industrial alkali lignin molecules | |
| CN101709113B (en) | Preparation of macromolecular compatible additive, namely urea-formaldehyde modified lignin and application of macromolecular compatible additive | |
| CN109650535B (en) | Application of lignin and derived carbon thereof in anaerobic digestion | |
| Abdulkhani et al. | Valorization of bagasse alkali lignin to water-soluble derivatives through chemical modification | |
| CN112030591A (en) | Novel method for recycling alkali from straw pulp black liquor by acid-alkali circulation | |
| CN104785162B (en) | A kind of amine-methylated lignin-base dispersant and preparation technology and application | |
| CN106906685B (en) | A method of high added value phenol products are prepared by black liquor of pulp making | |
| CN104743954A (en) | Method for preparing water reducer from oxyanthraquinone byproduct | |
| CN114364841A (en) | Process for extracting lignin from black liquor | |
| CN105452345B (en) | Compositions comprising lignin material | |
| CN104672404A (en) | Condition study on copolymerization and grafting of acrylamide and lignosulfonate | |
| CN112980536A (en) | Method for preparing biomass by using pulping black liquor | |
| CN113652099B (en) | Preparation method of alkali lignin-based dye dispersant | |
| Antaresti et al. | The effect of chemical and biopulping process on bagasse pulp | |
| CN111535068A (en) | Method for extracting bagasse fibers | |
| CN118063790B (en) | Demethoxy lignin and preparation method and application thereof | |
| Xu et al. | An integrated green process for beneficial utilization of pulping black liquor | |
| CN108951251B (en) | Method for extracting and separating lignin from dissolving pulp precooking liquid | |
| CN116535587B (en) | Natural plant polyphenol modified phenolic resin filtrate reducer for drilling fluid |
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 |