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CN111286039B - Method for separating and extracting high-activity lignin by taking needle-leaved wood as raw material - Google Patents

Method for separating and extracting high-activity lignin by taking needle-leaved wood as raw material Download PDF

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CN111286039B
CN111286039B CN202010223050.1A CN202010223050A CN111286039B CN 111286039 B CN111286039 B CN 111286039B CN 202010223050 A CN202010223050 A CN 202010223050A CN 111286039 B CN111286039 B CN 111286039B
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lignin
tsoh
softwood
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CN111286039A (en
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庞志强
黎鹏飞
吴丽冉
刘玉龙
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Qilu University of Technology
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08HDERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H6/00Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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Abstract

The invention belongs to the technical field of biomass refining and recycling, and relates to a method for separating and extracting high-activity lignin by taking needle-leaved wood as a raw material. Using (p-TsOH)/ClO2The system treats the raw materials. The invention is provided withp‑TsOH/ClO2The system separates and extracts high-yield high-activity softwood lignin,pTsOH and ClO2The synergistic effect can effectively promote the extraction of high-activity lignin of the softwood, and inhibit the repolymerization of lignin monomers and the generation of low-activity C-C connecting bonds. The lignin product obtained by the invention is easy to process and convert; the treatment condition is mild, the selectivity of the chlorine dioxide on lignin reaction is high, the degradation loss of polysaccharide is small, the method is easy to implement, the process is simple, and the efficiency is high. The fiber after lignin extraction has good quality and high yield of holocellulose, and can be used as an excellent biomass energy material.

Description

Method for separating and extracting high-activity lignin by taking needle-leaved wood as raw material
Technical Field
The invention belongs to the technical field of biomass refining and recycling, and relates to a method for separating and extracting high-activity lignin by taking needle-leaved wood as a raw material.
Background
The softwood fibers are longer, the length is generally between 2.56 and 4.08 mm, the width is between 40.9 and 54.9 mu m, and the aspect ratio is more below 70; the hardwood fibers are short, generally about 1 mm in length, and the aspect ratio is more than 60; the needle-leaved wood has a tight tissue structure and low content of impurity cells, and the impurity cells in the chemical pulp are mostly lost during washing, so that the pulp has good quality. The lignin content of the softwood is high and is between 25 and 35 percent, and the pentosan content is low and is between 9 and 12 percent.
The plant fiber raw material mainly comprises cellulose, hemicellulose and lignin. Lignin is a three-dimensional polymer compound formed by irregularly connecting phenylpropane structural units through carbon-carbon bonds and carbon-oxygen bonds, is widely present in most vascular plants, and plays a role in filling and bonding. The cellulose and the hemicellulose are bonded and reinforced by lignin, so that the plant is endowed with the performance of being stiff and stiff. The lignin content varies from plant species to plant species, and is about 25% to 35% in softwood. The lignin is the only reproducible aromatic compound in the nature, and if the lignin can be effectively utilized, the situation of resource and energy shortage in the world at present can be relieved, and the sustainable development of the energy can be promoted. Currently, there are three ways of utilizing lignin industrially, one is to degrade lignin into small aromatic molecular compounds that can be used as chemical raw materials; secondly, lignin is used as a natural unmodified component; thirdly, the lignin is used after being subjected to proper physical and chemical modification. The key of the processing and utilization of the lignin is whether the high-efficiency and high-activity lignin can be effectively separated.
A large number of active groups such as phenolic hydroxyl, alcoholic hydroxyl, methoxyl, carbonyl, carboxyl, ether bond and the like exist in the molecular structure of lignin, and the groups endow the lignin with stronger chemical reaction capability. The reaction types of lignin are roughly divided into two main groups, namely reactions on aromatic nuclei and reactions on side chains. The first kind of reaction is mainly nitration, halogenation, hydroxymethylation, phenolation, graft copolymerization and other reactions. The second category is mainly alkylation, isocyanation, esterification and phenolization, etc. The characteristic of lignin that is easily chemically modified provides the possibility for its wide industrial application. The preparation of high-efficiency active lignin can improve the utilization value of the lignin, and the development of the separation technology is particularly urgent. However, the softwood lignin is composed of guaiac units, has a large condensation degree and a large separation difficulty. Already existingp-The TsOH technology makes it difficult to achieve efficient separation of lignin.
Disclosure of Invention
The present invention is directed to the traditionp-The problem that the TsOH technology is difficult to realize the effective separation of lignin is providedThe method for separating and extracting high-activity lignin by using needle-leaved wood as a raw material.
In order to achieve the purpose, the invention is realized by adopting the following technical scheme:
a method for separating and extracting high-activity lignin from coniferous wood comprises adopting (p-TsOH)/ClO2The system treats the raw materials.
Preferably, the raw material is needle-leaved wood flour of 40-60 mesh.
Preferably, the method comprises the step of adding the coniferous wood to the aqueous solution of p-TsOH and ClO2After treatment in the treatment system, washing and filtering reaction products; centrifuging the filtrate, removing supernatant, and drying to obtain the product.
Preferably, the coniferous wood is treated under the conditions that the concentration of the p-TsOH aqueous solution is 70-80 wt%, and ClO is2The dosage of the raw materials of the needle leaved wood is 0.6 to 1.0 weight percent, the solid-liquid ratio is 1 (6 to 10), the temperature is 70 to 90 ℃, the time is 30 to 60 min, and the stirring speed is 400 plus 600 rpm.
Preferably, the filtration pore diameter is 30 to 50 μm, the washing solution is water, and the amount of water for washing is 2 to 6 times the volume of the reaction solution.
Preferably, the centrifugal treatment condition of the filtrate is centrifugal force of 400-800g, and the centrifugal time is 10-20 min.
Preferably, the drying condition is temperature of- (15-25) deg.C, vacuum degree of 5-10Pa, and time of 18-24 h.
Preferably, the product has a moisture content of less than 3.0 wt.%.
As a preference, the first and second liquid crystal compositions are,pdrying the TsOH treated waste liquid at the temperature of 105 ℃ and 110 ℃ until the water content is reduced<25% (mass fraction), cooling to-10 deg.C, recrystallizing to remove impurities, and regeneratingp-TsOH。
pTsOH is an aqueous cosolvent with hydrophilic sulfonic anions, whose molecular structure produces hydrophobic effects through interactive pi electron orbitals. Lignin passage in softwoodpThe hydrophobic aggregation effect of-TsOH can be dissolved out, but the traditional method is difficult to dissolve out lignin part which has high molecular weight, large condensation degree and is distributed in the raw material, the dissolving out capability is limited, the extraction rate of lignin is low, and potential active groups are not released. Unlike broad leavesThe lignin of wood and needle wood is mainly guaiacum base, the structure content of non-condensed lignin is high, and the proportion of chemical inert C-C bonds between lignin units is large, so that the restriction of said methodp-dissolution capacity of TsOH on coniferous wood. In the inventionpIn the TsOH system, ClO2Can effectively act on the structures of the phenolic hydroxyl, the aryl ether bond, the alkyl ether bond and the side chain double bond of the guaiacyl structure, improve the activity of the lignin units, release more hydroxyl and carboxyl groups and effectively reduce the connecting bonds among the lignin units. These changes can improve the mass transfer performance and accessibility of lignin and facilitate lignin inpDissolution under the action of TsOH. Due to the fact thatpThe affinity effect of-TsOH on pi electron orbitals of aromatic rings of lignin can effectively reduce ClO2The ring-opening degradation reaction of the lignin effectively retains the aromatic ring structure of the lignin.
The invention adoptsp-TsOH/ClO2The system can effectively activate the lignin of the softwood, improve the separation capability and realize the separation and extraction of the lignin of the high-efficiency and high-activity softwood.
Compared with the prior art, the invention has the advantages and positive effects that:
1. the invention is provided withp-TsOH/ClO2The system separates and extracts high-yield high-activity softwood lignin, pTsOH and ClO2The synergistic effect can effectively promote the extraction of high-activity lignin of the softwood, and inhibit the repolymerization of lignin monomers and the generation of low-activity C-C connecting bonds.
2. The lignin product obtained by the invention is easy to process and convert; the method has the advantages of mild treatment conditions, high selectivity of the chlorine dioxide to lignin reaction, low degradation loss of polysaccharide, easy implementation, simple process and high efficiency.
3. The adopted solvent and chemicals are green reagents, and the solvent can be recycled through evaporation and recrystallization, so that the generation of toxic pollutants can be avoided.
4. The fiber after lignin extraction has good quality and high yield of holocellulose, and can be used as an excellent biomass energy material.
Detailed Description
In order that the above objects, features and advantages of the present invention may be more clearly understood, the present invention will be further described with reference to specific embodiments. It should be noted that the embodiments and features of the embodiments of the present application may be combined with each other without conflict.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, however, the present invention may be practiced in other ways than those specifically described herein, and thus the present invention is not limited to the specific embodiments of the present disclosure.
In the following examples, the comparative examples in examples 1-3 were conventional kraft cooking to extract alkali lignin, where kraft cooking is the current technology of industrial application and the chemicals used are NaOH and Na2S, other conditions are kept consistent with the corresponding embodiments. Comparative example in example 4 was conducted using onlypTsOH treatment extracts lignin, other conditions remaining consistent.
Example 1
Adding 40-60 mesh powder of spruce into needle-leaved woodp-aqueous TsOH solution and ClO2The formed treatment system. The treatment conditions were:pconcentration of aqueous TsOH 70 wt%, ClO2The using amount is 0.7 wt% (relative to the raw material of the needle-leaved wood), the solid-liquid ratio is 1:9, the temperature is 90 ℃, the time is 40 min, the stirring speed is 500 rpm, the water amount which is 2 times of the volume of the reaction liquid is added after the reaction is finished to wash and filter the product, the aperture of the filter paper used for filtering is 30-50 mu m, the extracted lignin is coagulated and precipitated, the filtrate is centrifugally treated for 18 min under the condition of 600 g, the supernatant is removed, the precipitate is washed and is frozen and dried for 22 h under the temperature of-20 ℃ and the vacuum degree of 8 Pa to obtain the high-efficiency active lignin.
The extraction rate of the prepared high-efficiency active lignin is 45.2 percent, the alcoholic hydroxyl content is 7.6 mmol/g, the phenolic hydroxyl content is 6.5 mmol/g, the carboxyl content is 2.13 mmol/g, the aryl ether bond content is 65.2 percent, and the yield of the holocellulose is 78.6 percent.
Comparative example 1
The extraction rate of active lignin prepared from the spruce alkali lignin separated by the traditional sulfate cooking method is 41.6 percent, the alcoholic hydroxyl group content is 4.3 mmol/g, the phenolic hydroxyl group content is 3.6 mmol/g, the carboxyl group content is 1.05 mmol/g, the aryl ether linkage content is 38.2 percent, and the yield of the holocellulose is 48.3 percent.
Example 2
Adding 40-60 mesh wood powder of pinus massoniana into the mixturep-aqueous TsOH solution and ClO2The formed treatment system. The treatment conditions were:pconcentration of aqueous TsOH 75 wt%, ClO2The using amount is 0.8 wt% (relative to the raw material of the needle-leaved wood), the solid-liquid ratio is 1:6, the temperature is 85 ℃, the time is 30 min, the stirring speed is 400 rpm, the water amount which is 5 times of the volume of the reaction liquid is added after the reaction is finished to wash and filter the product, the aperture of the filter paper used for filtering is 30-50 mu m, the extracted lignin is coagulated and precipitated, the filtrate is centrifugally treated for 20min under the condition of 400 g, the supernatant is removed, the precipitate is washed and is frozen and dried for 18 h under the temperature of minus 25 ℃ and the vacuum degree of 10Pa to obtain the high-efficiency active lignin.
The extraction rate of the prepared high-efficiency active lignin is 46.3 percent, the alcoholic hydroxyl content is 7.9 mmol/g, the phenolic hydroxyl content is 6.6 mmol/g, the carboxyl content is 2.23 mmol/g, the aryl ether bond content is 64.5 percent, and the yield of the holocellulose is 76.7 percent.
Comparative example 2
The extraction rate of active lignin prepared from the masson pine lignin separated by the traditional sulfate cooking method is 37.5 percent, the alcoholic hydroxyl content is 3.5 mmol/g, the phenolic hydroxyl content is 2.7 mmol/g, the carboxyl content is 0.97 mmol/g, the aryl ether linkage content is 37.6 percent, and the yield of holocellulose is 47.2 percent.
Example 3
Adding 40-60 mesh wood powder of needle leaf aucklandia root resin fir to the powderp-aqueous TsOH solution and ClO2The formed treatment system. The treatment conditions were:paqueous TsOH solution concentration 80 wt%, ClO2The using amount is 0.6 wt% (relative to the raw material of the needle-leaved wood), the solid-liquid ratio is 1:10, the temperature is 70 ℃, the time is 60 min, the stirring speed is 600 rpm, the water amount which is 6 times of the volume of the reaction liquid is added after the reaction is finished to wash and filter the product, the aperture of the filter paper used for filtering is 30-50 mu m, the extracted lignin is coagulated and precipitated, the filtrate is centrifugally treated for 15 min under the condition of 500 g, the precipitate is taken to be washed, and the precipitate is frozen and dried for 20 h under the temperature of-15 ℃ and the vacuum degree of 5 Pa to obtain the high-efficiency active lignin.
The extraction rate of the prepared high-efficiency active lignin is 47.5 percent, the alcoholic hydroxyl group content is 8.1 mmol/g, the phenolic hydroxyl group content is 6.9 mmol/g, the carboxyl group content is 2.18 mmol/g, the aryl ether linkage content is 62.6 percent, and the yield of the holocellulose is 78.1 percent.
Comparative example 3
The extraction rate of active lignin prepared from balsam abietic lignin separated by cooking by a traditional sulfate method is 39.8 percent, the alcoholic hydroxyl group content is 4.1 mmol/g, the phenolic hydroxyl group content is 3.1 mmol/g, the carboxyl group content is 0.94 mmol/g, the aryl ether linkage content is 36.8 percent, and the yield of holocellulose is 46.5 percent.
Example 4
Adding 40-60 mesh wood powder of Larix gmelinii intop-aqueous TsOH solution and ClO2The formed treatment system. The treatment conditions were:pthe concentration of the aqueous TsOH solution used was 75% by weightpTsOH is recovered from the filtrate, ClO2The using amount is 1.0 wt% (relative to the raw material of the needle-leaved wood), the solid-liquid ratio is 1:10, the temperature is 80 ℃, the time is 50 min, the stirring speed is 500 rpm, the water amount which is 4 times of the volume of the reaction liquid is added after the reaction is finished to wash and filter the product, the aperture of the filter paper used for filtering is 30-50 mu m, the extracted lignin is coagulated and precipitated, the filtrate is centrifugally treated for 10 min under the condition of 800g, the supernatant is removed, the precipitate is washed and is frozen and dried for 24h under the temperature of-18 ℃ and the vacuum degree of 8 Pa to obtain the high-efficiency active lignin.
The extraction rate of the prepared high-efficiency active lignin is 43.4 percent, the alcoholic hydroxyl group content is 7.5 mmol/g, the phenolic hydroxyl group content is 6.7 mmol/g, the carboxyl group content is 1.97 mmol/g, the aryl ether bond content is 61.4 percent, and the yield of the holocellulose is 76.4 percent.
Comparative example 4
All adopt of larchpThe extraction rate of active lignin extracted by TsOH is 40.2%, the alcoholic hydroxyl group content is 5.8 mmol/g, the phenolic hydroxyl group content is 4.2 mmol/g, the carboxyl group content is 1.47 mmol/g, the aryl ether linkage content is 51.7%, and the yield of holocellulose is 67.2%.
Example 5
The waste liquid generated in example 3 was dried at a temperature of 105 ℃ and 110 ℃ to a moisture mass fraction<25%, cooling to-10 deg.C, recrystallizing to remove impurities, and recoveringp-TsOH. By recyclingp-TsOH construction separation treatmentProvided is a system. Other conditions are treated as above, i.e.pAqueous TsOH solution concentration 80 wt%, ClO2The using amount is 0.6 wt% (relative to the raw material of the needle-leaved wood), the solid-liquid ratio is 1:10, the temperature is 70 ℃, the time is 60 min, the stirring speed is 600 rpm, the water amount which is 6 times of the volume of the reaction liquid is added after the reaction is finished to wash and filter the product, the aperture of the filter paper used for filtering is 30-50 mu m, the extracted lignin is coagulated and precipitated, the filtrate is centrifugally treated for 15 min under the condition of 500 g, the precipitate is taken to be washed, and the precipitate is frozen and dried for 20 h under the temperature of-15 ℃ and the vacuum degree of 5 Pa to obtain the high-efficiency active lignin.
The extraction rate of the prepared high-efficiency active lignin is 47.1 percent, the alcoholic hydroxyl content is 7.8 mmol/g, the phenolic hydroxyl content is 6.5 mmol/g, the carboxyl content is 2.11 mmol/g, the aryl ether bond content is 60.2 percent, and the yield of the holocellulose is 78.4 percent. Recycled and regeneratedpThe loss of the-TsOH separation capacity is small.
Example 6
This example used the waste liquid produced in example 5, which was recovered 8 timespTsOH, recovered by drying at a temperature of 105 ℃ and 110 ℃ to a mass fraction of water<25%, cooling to-10 deg.C, recrystallizing to remove impurities, and recoveringp-TsOH. By recyclingpTsOH constitutes a separation treatment system. Other processing conditions remained consistent with example 3.
The extraction rate of the prepared high-efficiency active lignin is 47.0 percent, the alcoholic hydroxyl group content is 7.6 mmol/g, the phenolic hydroxyl group content is 6.1 mmol/g, the carboxyl group content is 2.03 mmol/g, the aryl ether bond content is 60.1 percent, and the yield of the holocellulose is 76.9 percent. Recycled and regeneratedpThe loss of the-TsOH separation capacity is small.
The above description is only a preferred embodiment of the present invention, and not intended to limit the present invention in other forms, and any person skilled in the art may apply the above modifications or changes to the equivalent embodiments with equivalent changes, without departing from the technical spirit of the present invention, and any simple modification, equivalent change and change made to the above embodiments according to the technical spirit of the present invention still belong to the protection scope of the technical spirit of the present invention.

Claims (6)

1. A method for separating and extracting high-activity lignin from softwood is characterized in that (p-TsOH)/ClO is adopted2Treating raw materials of the system;
comprises the steps of adding coniferous wood intopAqueous TsOH solution with ClO2After treatment in the treatment system, washing and filtering reaction products; centrifuging the filtrate, removing supernatant, and drying to obtain a product;
the conditions for the treatment of the needle-leaved wood are as follows,pthe concentration of the aqueous solution of TsOH is 70-80 wt%, ClO2The dosage of the raw materials of the needle leaved wood is 0.6 to 1.0 weight percent, the solid-liquid ratio is 1 (6 to 10), the temperature is 70 to 90 ℃, the time is 30 to 60 min, and the stirring speed is 400 plus 600 rpm;
the filtering pore diameter is 30-50 μm, the washing liquid is water, and the washing water consumption is 2-6 times of the volume of the reaction liquid.
2. The method for separating and extracting high-activity lignin by using softwood as a raw material according to claim 1, wherein the raw material is 40-60-mesh softwood flour.
3. The method for separating and extracting high-activity lignin from softwood as recited in claim 2, wherein the centrifugal treatment conditions of the filtrate are 400-800g of centrifugal force, and the centrifugal time is 10-20 min.
4. The method for separating and extracting high-activity lignin from softwood as claimed in claim 2, wherein the drying conditions are temperature- (15-25) deg.C, vacuum degree 5-10Pa, and time 18-24 h.
5. The method for separating and extracting high-activity lignin from softwood as claimed in claim 3, wherein the product moisture is less than 3.0 wt%.
6. The method as claimed in claim 1, wherein the p-TsOH is recovered after the reaction, and the recovery is carried out by drying at 105 ℃ and 110 ℃ until the water content is less than 25%, and then cooling to-10 ℃ for recrystallization.
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Country or region after: China

Address before: 250000 science and Technology Park, Xincheng University, Jinan, Shandong Province

Patentee before: Qilu University of Technology

Country or region before: China

CP03 Change of name, title or address