CN114085252A - Comprehensive utilization method for separating wood fiber by organic acid catalysis two-phase system - Google Patents
Comprehensive utilization method for separating wood fiber by organic acid catalysis two-phase system Download PDFInfo
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- CN114085252A CN114085252A CN202111225513.9A CN202111225513A CN114085252A CN 114085252 A CN114085252 A CN 114085252A CN 202111225513 A CN202111225513 A CN 202111225513A CN 114085252 A CN114085252 A CN 114085252A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
- C07D307/50—Preparation from natural products
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C5/00—Other processes for obtaining cellulose, e.g. cooking cotton linters ; Processes characterised by the choice of cellulose-containing starting materials
Abstract
The invention provides a comprehensive utilization method for separating wood fiber by an organic acid catalysis two-phase system. And (3) ultrasonically standing the filtrate for layering, dissolving the saccharides in the NaCl salt solution at the lower layer, and dispersing the phenols in the polar aprotic solvent at the upper layer. Adding water into the upper organic phase, stirring, standing, centrifuging to obtain brown powder, cleaning, and freeze drying to obtain dissociated lignin. The centrifugate is subjected to reduced pressure fractional distillation to recover water and polar aprotic solvent. And directly heating the saccharides in the lower layer to convert the saccharides into furfural, carrying out reduced pressure distillation to obtain a furfural product, and recovering organic acid and water. The recovered water, organic acid and polar aprotic solvent can be recycled.
Description
Technical Field
The invention belongs to a pretreatment technology of a wood fiber biomass raw material, and mainly relates to a directional depolymerization of three major components of cellulose, hemicellulose and lignin in wood fiber biomass and a full-quality high-efficiency separation method of depolymerized components.
Background
Due to environmental problems caused by the shortage and excessive development of global fossil energy resources, people are getting more and more concerned about green renewable energy resources that can replace fossil energy. Lignocellulosic biomass is considered one of the most promising renewable carbon resources, and can be converted into liquid fuels and chemicals. Wherein the fast-growing wood remainder is such as paper mulberry powder, eucalyptus powder, fir powder, poplar powder, elm powder, fast-growing ash tree powder, birch powder and other biomass resources, and has the advantages of rich resource, low cost and easy acquisition. They can be mass-produced into liquid fuels such as bioethanol, butanol, etc. or used for preparing high value-added chemicals, degradable materials, etc. by a biorefinery process. The biological refining research of the wood fiber resource of the fast growing wood residue is developed, the processes of energy safety, energy conservation, emission reduction and environmental protection can be effectively promoted, and the method has important economic and social benefits.
Lignocellulosic biomass is composed of three major components, 35-53% cellulose, 20-37% hemicellulose and 15-30% lignin. Cellulose is the skeletal part of the biomass structure, surrounded by lignin and hemicellulose, in other words, lignin is a protective layer of hemicellulose and cellulose. They are interconnected by hydrogen bonds and anisole bonds, and prevent enzymes and chemicals from directly contacting cellulose by intermolecular forces such as van der waals forces, etc., to form a lignin-carbohydrate composite structure. In addition, due to the complex structure of lignocellulosic biomass, inhibition of lignocellulose hydrolysis by hemicellulose and lignin depolymerization products reduces biorefinery efficiency. Furthermore, studies have shown that the presence of lignin has a greater influence on the anti-biodegradation properties of the lignocellulosic cell wall. It has been reported that lignin produces nonproductive binding with cellulase enzymes, causing the enzymes to inefficiently adsorb cellulose through hydrophobic interactions, electrostatic interactions and hydrogen bonding interactions, inhibiting the bioconversion of lignocellulosic biomass. Therefore, the effective pretreatment process can selectively and efficiently remove hemicellulose and lignin, destroy the structure of lignocellulose, reduce the polymerization degree of cellulose, and increase the effective contact of the cellulose and chemical reagents on the cellulose, so that the biological oil refining process is more efficient and environment-friendly.
At present, common lignocellulose biomass solvent pretreatment methods include an organic solvent pretreatment method such as alcohol, ketone, phenol and the like, an Ionic Liquid (ILs) pretreatment method and a eutectic solvent (DESS) pretreatment method, and common polar aprotic solvents such as 1, 4-dioxane, methyl isobutyl ketone (MIBK), dimethyl sulfoxide (DMSO) and the like.
Pretreatment method
Due to the outstanding effect of the organic solvent on the breakage of hydrogen bonds, ether bonds and glucoside, the organic solvent pretreatment can remove a large amount of lignin and almost all hemicellulose, thereby improving the enzymolysis efficiency. In addition, the addition of a catalyst can further improve the pretreatment effect. Organic solvents commonly used in the pretreatment process are ethanol, acetone, phenol, and the like. In recent years, ethanol has received the favor of extensive researchers due to its low cost, low toxicity, easy recovery and high biomass production. It is reported that liriodendron tulipifera removes about 80% of the lignin under optimal pretreatment conditions in an ethanol/dilute sulfuric acid solvent system. Although the pretreatment efficiency of the organic solvent is high, the problems of volatility, flammability, environmental pollution, energy consumption and the like of the organic solvent still exist.
Ionic liquids, which are a new type of solvent, are generally composed of organic cations (imidazole, piperidine, ammonium, etc.) and organic or inorganic anions and exist in the liquid phase at room temperature. ILs are widely used for the separation of the main components of lignocellulosic biomass due to their properties of selective dissolution of lignin and cellulose, renewability and biodegradability. Compared with common solvents, the ionic liquid has the characteristics of small volatility, low vapor pressure, and high electrochemical stability and thermal stability. Despite the above outstanding advantages, ILs still have the disadvantages of high cost, difficult recovery process, incompatibility with enzymes and microorganisms, etc., which significantly affects their large-scale industrial application in the pretreatment of lignocellulosic biomass.
The eutectic solvent is a novel environment-friendly solvent with the characteristics of organic solvents and ionic liquids, generally comprises Hydrogen Bond Acceptors (HBAs) such as quaternary ammonium salt and betaine and Hydrogen Bond Donors (HBDs) such as urea and carboxylic acid in a certain proportion, and has the characteristics of low toxicity, low cost, non-volatility, high thermal stability, good solubility, environmental friendliness and the like. DESs can effectively remove lignin, dissolve most hemicellulose, and largely retain cellulose, which facilitates the selective separation of the three major components of lignocellulosic biomass. Although DESs has great potential in separating lignocellulosic components, its high viscosity is a significant disadvantage and the product is difficult to separate.
Although the common pretreatment method of the organic solvent of alcohol, ketone and phenol can separate three components, the method has the problems of low boiling point of the organic solvent, harsh reaction conditions and the like. Although ionic liquid and eutectic solvent can separate three major elements, the products are difficult to separate, and the solvent is difficult to recover, so that large-scale industrial application cannot be carried out at present. Although the pretreatment effect of a common polar aprotic/water composite solvent system is good, the solvent is high in toxicity, and a target product is difficult to separate, so that the three major elements cannot be utilized in a high-value mode.
Although there are many methods for separating the three components, the currently mature techniques still have problems that have not been solved or aspects that need improvement:
(1) the separation of products and the recovery of the solvent are difficult in the pretreatment of the ionic liquid and the eutectic solvent.
(2) The reaction mechanism of the eutectic solvent is not sufficiently researched, the cost is high, and the product recovery and the solvent recovery are difficult.
(3) The common organic solvent of alcohol and ketone has low boiling point and harsh reaction conditions.
(4) In the existing common polar aprotic/water composite solvent system, target products are difficult to separate and are easy to generate polymerization and other reactions.
(5) The existing pretreatment method hydrolyzes hemicellulose into micromolecular substances such as furfural, acetic acid and the like while separating cellulose, discharges the micromolecular substances together with lignin along with waste liquid, has low additional value, and is difficult to realize high-additional-value full utilization of wood fiber biomass.
Therefore, a two-phase pretreatment system of polar aprotic solvent/NaCl salt solution with excellent selectivity for separating three major components from the wood fiber biomass is selected to gradually and efficiently separate cellulose, hemicellulose and lignin in the wood fiber raw material, and finally obtain cellulose, furfural, dissociated lignin, polar aprotic solvent and organic acid with high added values, which is the key for enabling the wood fiber biorefinery process to be more efficient and environment-friendly.
Disclosure of Invention
The purpose of the invention is as follows: the method aims to solve the bottleneck problems that complete separation and utilization of lignocellulose, hemicellulose and lignin components of the lignocellulose biomass are difficult to realize, the reaction is complex in the production process, products are complex and diverse and are difficult to separate, and a solvent is not recyclable in the prior art. The invention aims to provide a comprehensive utilization method for separating wood fibers by an organic acid catalysis biphasic system, three high-added-value products with high purity are obtained, and high-value utilization of the wood fibers is realized.
The technical scheme of the invention is as follows: a comprehensive utilization method for separating wood fiber by an organic acid catalysis biphasic system comprises the following steps:
the first step is as follows: crushing and sieving the fast growing wood residues, and adding the crushed and sieved fast growing wood residues, a polar aprotic solvent, a NaCl salt solution and an organic acid into a pressurized reaction kettle according to a certain mass ratio;
the second step is that: raising the temperature of the reaction kettle for pretreatment, then cooling to room temperature, standing, filtering, washing solid residues with deionized water, and then drying the solid residues to obtain high-purity cellulose;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze drying to obtain dissociated lignin;
the fifth step: the saccharides in the salt solution with the lower layer rich in organic acid can be directly heated and converted into furfural, and the furfural is obtained after reduced pressure distillation.
The polar aprotic solvent is any one of sulfolane, dihydrolevoglucosenone, DMSO, gamma-valerolactone, Diformylxylose, DMI and THF.
The organic acid is any one of malonic acid, succinic acid, tartaric acid, p-toluenesulfonic acid, glycolic acid and sorbic acid.
The raw material is any one of paper mulberry, eucalyptus, fir, poplar, elm, fast-growing white wax and birch remainder.
The system is a polar aprotic solvent/NaCl salt solution two-phase system.
The mass ratio of the fast growing wood residues to the polar aprotic solvent/NaCl salt solution is 1/5-1/21.2; the mass ratio of the fast growing wood residue to the organic acid is 1/0.05-1/0.5; the mass ratio of the polar aprotic solvent to the deionized water in the polar aprotic solvent/NaCl salt solution double-phase system is 9/1-1/9; the mass ratio of NaCl to water in the polar aprotic solvent/NaCl salt solution two-phase system is 0.2/1-0.4/1.
The second step of pretreatment is carried out at the temperature of 80-150 ℃ for 20-80 min.
The drying temperature of the second step is 105-120 ℃.
Water, organic acid and the polar aprotic solvent in the polar aprotic solvent/NaCl salt solution biphase system can be recovered by reduced pressure distillation for recycling.
Has the advantages that:
1. the method takes fast growing wood residues as raw materials, and then adds wood fiber biomass powder, a polar aprotic solvent, a NaCl salt solution and organic acid into a pressurized reaction kettle according to a certain mass ratio for pretreatment; and after the pretreatment is finished, cooling to room temperature, standing, filtering to obtain solid residue and filtrate, washing the solid residue with deionized water, drying and weighing to obtain the high-purity cellulose obtained by separation. And (3) performing ultrasonic treatment on the filtrate, pouring the filtrate into a separating funnel, standing and layering, dissolving hemicellulose-degraded saccharides in a NaCl salt solution at the lower layer, and dispersing phenols obtained by lignin depolymerization in a polar aprotic solvent at the upper layer. Adding a certain amount of deionized water into the upper organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain the separated dissociated lignin. The centrifugate is subjected to reduced pressure fractional distillation to recover water and polar aprotic solvent. The saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
2. The method of the invention has no special requirement on the water content of the remainder raw material of the fast growing wood, and can be suitable for fiber biomass from various raw material sources, such as: corncob, eucalyptus, fast-growing ash, poplar, willow, mao bamboo, birch, pine, paper mulberry, corn straw, wheat straw, cotton stalk, rice straw and the like. The raw materials are low in price and wide in source, and the cost in the separation operation process is greatly reduced.
3. The method has simple process and strong operability, the used polar aprotic solvent has excellent thermal stability and chemical stability, the saturated vapor pressure is low, and the three major elements can be efficiently separated.
4. The polar aprotic solvent used in the method can be efficiently recovered and reused, and is green and environment-friendly.
5. The organic acid used in the method can be repeatedly used, and the utilization rate is high.
6. The method of the invention carries out solvent pretreatment on the fast growing wood remainder raw material, and has mild reaction conditions, simple operation and high efficiency.
7. The method takes fast growing wood residues as raw materials, can realize the high-efficiency separation of three major substances through simple polar aprotic solvent-NaCl salt solution two-phase system pretreatment, obtains pentose, lignin and polar aprotic solvent which are obtained by degrading cellulose and hemicellulose with high added values, and realizes the low-cost high-valued full utilization of the forest grass wood fiber raw materials.
Drawings
FIG. 1 is an XRD pattern of filter residue after pretreatment of poplar powder;
FIG. 2 is an infrared image of lignin after pretreatment of cedar flour;
FIG. 3 is a flow chart of the method for preparing high-purity cellulose, furfural, dissociated lignin, polar aprotic solvent and organic acid from fast growing wood residues.
Detailed Description
The present invention is described in further detail below with reference to the attached drawing figures.
Taking fast growing wood residues as a raw material, firstly obtaining wood fiber biomass powder by a ball milling method, and then adding the powder, a polar aprotic solvent, a NaCl salt solution and an organic acid into a pressurized reaction kettle according to a certain mass ratio for pretreatment; and after the pretreatment is finished, cooling to room temperature, standing, filtering to obtain solid residue and filtrate, washing the solid residue with deionized water, drying and weighing to obtain the high-purity cellulose obtained by separation. And (3) performing ultrasonic treatment on the filtrate, pouring the filtrate into a separating funnel, standing and layering, dissolving hemicellulose-degraded saccharides in a NaCl salt solution at the lower layer, and dispersing phenols obtained by lignin depolymerization in a polar aprotic solvent at the upper layer. Adding a certain amount of deionized water into the upper organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain the separated dissociated lignin. The centrifugate is subjected to reduced pressure fractional distillation to recover water and polar aprotic solvent. The saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
The comprehensive utilization method for separating wood fibers by using the organic acid catalysis biphasic system comprises the following steps:
the first step is as follows: crushing and sieving fast growing wood residues by a ball mill, and adding the crushed and sieved fast growing wood residues, a polar aprotic solvent, a NaCl salt solution and an organic acid into a pressurized reaction kettle according to a certain mass ratio;
the second step is that: raising the temperature of the reaction kettle to 80-150 ℃, carrying out pretreatment for 20-80 min, cooling to room temperature, standing, filtering, washing solid residues with deionized water, drying the solid residues at 105-120 ℃, and weighing to obtain high-purity cellulose after separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
The comprehensive utilization method for separating the wood fibers by the organic acid catalysis biphasic system is characterized in that the polar aprotic solvent is any one of sulfolane, dihydrolevoglucosenone, DMSO, gamma-valerolactone, Diformylxylose, DMI, THF and the like.
The comprehensive utilization method for separating the wood fiber by the organic acid catalytic dual-phase system is characterized in that the organic acid is any one of malonic acid, succinic acid, tartaric acid, p-toluenesulfonic acid, glycolic acid, sorbic acid and the like.
The comprehensive utilization method for separating wood fiber by the organic acid catalysis two-phase system comprises the step of taking the raw materials of any one of paper mulberry, eucalyptus, fir, poplar, elm, fast-growing white wax and birch remainder as the raw materials.
The comprehensive utilization method for separating the wood fiber by the organic acid catalysis biphasic system is characterized in that the system is a polar aprotic solvent/NaCl salt solution biphasic system.
According to the comprehensive utilization method for separating the wood fibers by the organic acid catalysis two-phase system, the mass ratio of the fast growing wood residues to the polar aprotic solvent/NaCl salt solution is 1/5-1/21.2.
The comprehensive utilization method for separating the wood fiber by the organic acid catalysis dual-phase system is characterized in that the mass ratio of the fast growing wood residues to the organic acid is 1/0.05-1/0.5.
The comprehensive utilization method for separating the wood fibers by the organic acid catalysis biphasic system is characterized in that the mass ratio of the polar aprotic solvent to the deionized water in the polar aprotic solvent/NaCl salt solution biphasic system is 9/1-1/9.
The comprehensive utilization method for separating wood fibers by using the organic acid catalysis two-phase system is characterized in that the mass ratio of NaCl to water in the polar aprotic solvent/NaCl salt solution two-phase system is 0.2/1-0.4/1.
The comprehensive utilization method for separating wood fibers by the organic acid catalysis two-phase system is characterized in that saccharides in a salt solution with organic acid in the lower layer in the polar aprotic solvent/NaCl salt solution two-phase system can be directly heated and converted into furfural, and a furfural product is obtained after reduced pressure distillation.
The comprehensive utilization method for separating the wood fiber by the organic acid catalysis biphasic system can efficiently separate cellulose, hemicellulose and lignin in the polar aprotic solvent/NaCl salt solution biphasic system.
According to the comprehensive utilization method for separating the wood fibers by the organic acid catalysis biphasic system, water, the organic acid and the polar aprotic solvent recovered from the polar aprotic solvent/NaCl salt solution biphasic system can be recycled.
The reaction process is described below by way of example.
Example 1:
the first step is as follows: crushing 10g of moso bamboo felling processing residues (the cellulose content is 4.03g, the hemicellulose content is 2.61g, and the lignin content is 2.92g) by a ball mill, sieving (120 meshes), mixing the obtained moso bamboo powder with 106g of gamma-valerolactone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/10.6, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 1.5g of p-toluenesulfonic acid (the mass ratio of the raw material to the acid is 1/0.15), and adding into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 130 ℃, reacting for 20min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
TABLE 1
Table 1 shows the mass fractions of cellulose, hemicellulose and lignin, the retention rate of cellulose, the removal rate of hemicellulose and lignin, and the mass fractions of the residue after the raw material and the residue are reacted at 130 ℃ for different reaction times (20min, 40min, 60min and 80 min).
Example 2:
the first step is as follows: crushing 10g of moso bamboo felling processing residues (the cellulose content is 4.03g, the hemicellulose content is 2.61g, and the lignin content is 2.92g) by a ball mill, sieving (120 meshes), mixing the obtained moso bamboo powder with 106g of gamma-valerolactone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/10.6, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 1.5g of p-toluenesulfonic acid (the mass ratio of the raw material to the acid is 1/0.15), and adding into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 130 ℃, reacting for 40min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 3:
the first step is as follows: crushing 10g of moso bamboo felling processing residues (the cellulose content is 4.03g, the hemicellulose content is 2.61g, and the lignin content is 2.92g) by a ball mill, sieving (120 meshes), mixing the obtained moso bamboo powder with 106g of gamma-valerolactone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/10.6, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 1.5g of p-toluenesulfonic acid (the mass ratio of the raw material to the acid is 1/0.15), and adding into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 130 ℃, reacting for 60min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 4:
the first step is as follows: crushing 10g of moso bamboo felling processing residues (the cellulose content is 4.03g, the hemicellulose content is 2.61g, and the lignin content is 2.92g) by a ball mill, sieving (120 meshes), mixing the obtained moso bamboo powder with 106g of gamma-valerolactone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/10.6, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 1.5g of p-toluenesulfonic acid (the mass ratio of the raw material to the acid is 1/0.15), and adding into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 130 ℃, reacting for 80min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 5:
the first step is as follows: 10 poplar wood chips (cellulose content 4.05g, hemicellulose content 3.23g and lignin content 1.77g) are crushed by a ball mill and sieved (120 meshes), and the obtained poplar powder is mixed with 106g of sulfolane-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/10.6, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1) and 1.5g of malonic acid (the mass ratio of the raw material to the acid is 1/0.15) and then added into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 130 ℃, reacting for 60min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 6:
the first step is as follows: 10g of fir (cellulose content 4.39g, hemicellulose content 0.6g, lignin content 2.97g) was pulverized by a ball mill and sieved (120 mesh), and the obtained fir powder was mixed with 106g of THF-NaCl salt solution (raw material to biphasic system mass ratio 1/10.6, solvent to water mass ratio 4/1, NaCl to water mass ratio 0.3/1) and 1.5g of tartaric acid (raw material to acid mass ratio 1/0.15) and then added to a pressurized reaction vessel.
The second step is that: raising the temperature of the reaction kettle to 130 ℃, reacting for 60min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 7:
the first step is as follows: crushing 10g of paper mulberry felling processing residues (the cellulose content is 3.36g, the hemicellulose content is 4.1g, and the lignin content is 1.73g) by a ball mill, sieving the crushed materials (120 meshes), mixing the obtained paper mulberry powder with 159g of gamma-valerolactone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/15.9, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 2.0g of succinic acid (the mass ratio of the raw material to the acid is 1/0.2), and adding the mixed materials into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 140 ℃, reacting for 20min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 8:
the first step is as follows: crushing 10g of birch felling processing residues (the cellulose content is 4.61g, the hemicellulose content is 2.57g, and the lignin content is 1.6g) by a ball mill, sieving (120 meshes), mixing the obtained birch powder with 159g of dihydrolevoglucosone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/15.9, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 1.5g of sorbic acid (the mass ratio of the raw material to the acid is 1/0.15), and adding into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 100 ℃, reacting for 80min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 9:
solvents used in this example: gamma valerolactone, succinic acid and water were all the solvents recovered in example 7.
The first step is as follows: crushing 10g of paper mulberry felling processing residues (the cellulose content is 3.36g, the hemicellulose content is 4.1g, and the lignin content is 1.73g) by a ball mill, sieving the crushed materials (120 meshes), mixing the obtained paper mulberry powder with 159g of gamma-valerolactone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/15.9, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 2.0g of succinic acid (the mass ratio of the raw material to the acid is 1/0.2), and adding the mixed materials into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 140 ℃, reacting for 20min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 10:
solvents used in this example: gamma valerolactone, succinic acid and water were all the solvents recovered in example 9.
The first step is as follows: crushing 10g of paper mulberry felling processing residues (the cellulose content is 3.36g, the hemicellulose content is 4.1g, and the lignin content is 1.73g) by a ball mill, sieving the crushed materials (120 meshes), mixing the obtained paper mulberry powder with 159g of gamma-valerolactone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/15.9, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 2.0g of succinic acid (the mass ratio of the raw material to the acid is 1/0.2), and adding the mixed materials into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 140 ℃, reacting for 20min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Example 11:
solvents used in this example: gamma valerolactone, succinic acid and water were all the solvents recovered in example 10.
The first step is as follows: crushing 10g of paper mulberry felling processing residues (the cellulose content is 3.36g, the hemicellulose content is 4.1g, and the lignin content is 1.73g) by a ball mill, sieving the crushed materials (120 meshes), mixing the obtained paper mulberry powder with 159g of gamma-valerolactone-NaCl salt solution (the mass ratio of the raw material to the biphasic system is 1/15.9, the mass ratio of the solvent to the water is 4/1, the mass ratio of the NaCl to the water is 0.3/1), and 2.0g of succinic acid (the mass ratio of the raw material to the acid is 1/0.2), and adding the mixed materials into a pressurized reaction kettle.
The second step is that: raising the temperature of the reaction kettle to 140 ℃, reacting for 20min, cooling to room temperature, standing, filtering, washing the solid residue with deionized water, drying the solid residue at 105 ℃, weighing, and taking the dried solid residue as the high-purity cellulose obtained by separation;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding a certain amount of deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze-drying to obtain separated dissociated lignin; recovering water and polar aprotic solvent from the obtained centrifugate by reduced pressure fractional distillation;
the fifth step: the saccharides in the salt solution with the lower layer rich in the organic acid can be directly heated and converted into furfural, a furfural product is obtained after reduced pressure distillation, and the organic acid and water are recovered. The recovered water, organic acid and polar aprotic solvent can be recycled.
Claims (9)
1. A comprehensive utilization method for separating wood fiber by an organic acid catalysis biphasic system is characterized by comprising the following steps:
the first step is as follows: crushing and sieving the fast growing wood residues, and adding the crushed and sieved fast growing wood residues, a polar aprotic solvent, a NaCl salt solution and an organic acid into a pressurized reaction kettle according to a certain mass ratio;
the second step is that: raising the temperature of the reaction kettle for pretreatment, then cooling to room temperature, standing, filtering, washing solid residues with deionized water, and then drying the solid residues to obtain high-purity cellulose;
the third step: the obtained filtrate is subjected to ultrasonic treatment and then poured into a separating funnel for standing and layering, hemicellulose degraded saccharides are dissolved in a NaCl salt solution at the lower layer, and phenols obtained by lignin depolymerization are dispersed in a polar aprotic solvent at the upper layer;
the fourth step: adding deionized water into the obtained upper layer organic phase, stirring, standing and centrifuging to obtain brown powder, washing with deionized water, and freeze drying to obtain dissociated lignin;
the fifth step: the saccharides in the salt solution with the lower layer rich in organic acid can be directly heated and converted into furfural, and the furfural is obtained after reduced pressure distillation.
2. The method for comprehensively utilizing the wood fiber separated by the organic acid catalysis biphasic system according to claim 1, wherein the method comprises the following steps: the polar aprotic solvent is any one of sulfolane, dihydrolevoglucosenone, DMSO, gamma-valerolactone, Diformylxylose, DMI and THF.
3. The method for comprehensively utilizing the wood fiber separated by the organic acid catalysis biphasic system according to claim 1, wherein the method comprises the following steps: the organic acid is any one of malonic acid, succinic acid, tartaric acid, p-toluenesulfonic acid, glycolic acid and sorbic acid.
4. The method for comprehensively utilizing the wood fiber separated by the organic acid catalysis biphasic system according to claim 1, wherein the method comprises the following steps: the raw material is any one of paper mulberry, eucalyptus, fir, poplar, elm, fast-growing white wax and birch remainder.
5. The method for comprehensively utilizing the wood fiber separated by the organic acid catalysis biphasic system according to claim 1, wherein the method comprises the following steps: the system is a polar aprotic solvent/NaCl salt solution two-phase system.
6. The method for comprehensively utilizing the wood fiber separated by the organic acid catalysis biphasic system according to claim 1, wherein the method comprises the following steps: the mass ratio of the fast growing wood residues to the polar aprotic solvent/NaCl salt solution is 1/5-1/21.2; the mass ratio of the fast growing wood residue to the organic acid is 1/0.05-1/0.5; the mass ratio of the polar aprotic solvent to the deionized water in the polar aprotic solvent/NaCl salt solution double-phase system is 9/1-1/9; the mass ratio of NaCl to water in the polar aprotic solvent/NaCl salt solution two-phase system is 0.2/1-0.4/1.
7. The method for comprehensively utilizing the wood fiber separated by the organic acid catalysis biphasic system according to claim 1, wherein the method comprises the following steps: the second step of pretreatment is carried out at the temperature of 80-150 ℃ for 20-80 min.
8. The method for comprehensively utilizing the wood fiber separated by the organic acid catalysis biphasic system according to claim 1, wherein the method comprises the following steps: the drying temperature of the second step is 105-120 ℃.
9. The method for comprehensively utilizing the wood fiber separated by the organic acid catalysis biphasic system according to claim 1, wherein the method comprises the following steps: water, organic acid and the polar aprotic solvent in the polar aprotic solvent/NaCl salt solution biphase system can be recovered by reduced pressure distillation for recycling.
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