CN113307983A - Method for separating lignin by green solvent quickly and in high yield - Google Patents
Method for separating lignin by green solvent quickly and in high yield Download PDFInfo
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Abstract
The invention provides a method for quickly separating lignin from a green solvent at a high yield, which comprises the following steps: (1) mixing and heating the first hydrogen bond donor, the second hydrogen bond donor and the hydrogen bond acceptor to obtain a homogeneous transparent ternary eutectic solvent; (2) adding a lignocellulose raw material into the ternary eutectic solvent in the step (1) for heating treatment to obtain slurry; (3) adding an acetone aqueous solution into the slurry obtained in the step (2), stirring, filtering to obtain a filtrate, washing filter residues with the acetone aqueous solution until a washing solution is colorless, and combining the filtrate and the washing solution; (4) evaporating and concentrating, extracting, and adding saturated salt solution for regeneration to obtain lignin. The method has the advantages of simple and convenient process operation, low cost and environmental friendliness.
Description
Technical Field
The invention belongs to the technical field of utilization of lignocellulose, and particularly relates to a method for separating lignin from lignocellulose.
Background
Lignocellulose is a renewable resource with extremely abundant reserves on the earth, and lignin is one of the main components of the lignocellulose and mainly comprises syringyl propane (S unit), guaiacyl propane (G unit) and p-hydroxyphenyl propane (H unit). Lignin is the only renewable aromatic polymer on earth, and has the potential to partially replace petrochemical resources. The lignin adhesive contains active groups such as phenolic hydroxyl, alcoholic hydroxyl, carbonyl and the like, and can be used for producing materials such as lignin adhesive, polyurethane and the like; lignin also contains different numbers of ether bonds, and phenolic monomers can be produced through hydrogenation catalysis. However, lignocellulose has a complex structure, and lignin, hemicellulose and cellulose have interaction forces such as hydrogen bonds, which brings great challenges to the rapid and controllable separation of lignin and high yield.
The main lignin separation methods at present include chemical methods (acid method, alkaline method, organic solvent method, ionic liquid method and eutectic solvent method), physical methods (ball milling method, high-pressure homogenization method and the like), biological methods (enzyme method) and other auxiliary methods (ultrasonic assistance, ball milling assistance, microwave assistance and the like), and the like, and the combination of the methods. The Chinese invention patent CN110172160A discloses a method for separating high-purity lignin from agricultural and forestry waste by using a green solvent, which comprises the following steps: the agricultural and forestry waste is treated by using a eutectic solvent at 140 ℃ for 2 hours, the reaction liquid is rapidly cooled and centrifugally separated after the reaction is finished, and lignin is precipitated by adding deionized water into the supernatant, wherein the yield is 70%. The Chinese patent CN110527111A adopts a lactic acid/zinc chloride solvent system to treat lignocellulose for 3 hours, the treatment temperature is 110 ℃, ethanol is added into the system after the reaction is finished to dilute the reaction solution, the ethanol is removed from the liquid obtained by solid-liquid separation, and then the liquid is dripped into deionized water to regenerate lignin, wherein the yield is 73.3%.
However, the prior art has at least the following disadvantages: the separation time is long, the yield of the lignin is generally lower than 80%, the molecular weight of the obtained lignin is large, the obtained lignin cannot be dissolved in a large amount of common organic solvents, the solvent recovery for lignin treatment consumes more energy, and the improvement of the economic benefit and the environmental benefit of the process is not facilitated.
Disclosure of Invention
In view of the technical problems existing in the current lignin separation and extraction process, namely the defects of long time consumption, low extraction rate and the like existing in the existing binary acid eutectic solvent extraction method, the main reasons for the phenomenon are as follows: the extraction process is long and the lignin is excessively degraded during the treatment process, resulting in incomplete recovery. The invention adopts a novel ternary eutectic solvent, wherein the first hydrogen bond donor such as formic acid, glyoxylic acid and pyruvic acid can generate an acetal structure with lignin under the catalysis of the second hydrogen bond donor such as p-toluenesulfonic acid to inhibit the over-degradation of the lignin, and the second hydrogen bond donor has a benzene ring structure similar to the lignin and can promote the dissolution of the lignin. Based on the above, the first hydrogen bond donor, the second hydrogen bond donor and the hydrogen bond acceptor are selected to synthesize the ternary eutectic solvent, so that the lignin can be quickly separated with high yield.
The invention provides a method for quickly separating lignin from a green solvent at a high yield, which comprises the following steps:
(1) mixing and heating a lignocellulose raw material and a ternary eutectic solvent to obtain slurry;
the preparation method of the ternary eutectic solvent comprises the following steps: mixing the first hydrogen bond donor, the second hydrogen bond donor and the hydrogen bond acceptor, heating for 1-3 hours at 50-70 ℃, and stirring at the frequency of 300-800 r/m to obtain a homogeneous transparent ternary eutectic solvent; preferably, the mixture is heated for 1.5 to 2.5 hours at the temperature of between 55 and 65 ℃, and the stirring frequency is 400 to 600 revolutions per minute;
(2) adding an acetone aqueous solution into the slurry obtained in the step (1), stirring, filtering to obtain a filtrate, washing residues with the acetone aqueous solution, and combining the filtrate and a washing solution to obtain a primary extraction mixed solution;
(3) evaporating and concentrating the primary extraction mixed solution, and extracting the primary extraction mixed solution, preferably repeating the extraction for two to four times;
(4) concentrating the extract obtained in the step (3), dropwise adding the concentrate into vigorously stirred saturated salt solution for regeneration, and then filtering to obtain solid residues; further, freeze-drying the solid obtained by filtering. Preferably, the solid is precipitated by adding saturated saline and stirring overnight.
Still further comprising freeze-drying the solid residue.
Preferably, the molar ratio of the first hydrogen bond donor, the second hydrogen bond donor and the hydrogen bond acceptor in the step (1) is 0.01-0.10: 2-10: 1. Preferably, the molar ratio is in the range of 0.01 to 0.10:2 to 10:1, and more preferably in the range of 0.01 to 0.05:2: 1.
Preferably, the hydrogen bond acceptor in step (1) may be selected from one or more of choline oxide, choline chloride, betaine or a salt compound having a positive charge and capable of forming a coordination bond with a negatively charged hydroxyl group, preferably one of choline oxide, choline chloride and betaine.
Preferably, the first hydrogen bond donor in step (1) is carboxylic acid species such as formic acid, acetic acid, oxalic acid, malonic acid, glyoxylic acid, pyruvic acid, and the second hydrogen bond donor is strong acid species containing a benzene ring such as p-hydroxybenzenesulfonic acid, p-toluenesulfonic acid.
Preferably, the lignocellulose in the step (1) is selected from needle-leaved wood, broad-leaved wood, bamboo or grass raw materials, crushed particles with the size of 10-60 meshes, wood chips or bamboo chips with the length of 1-4 cm and the width of 0.5-2 cm, grass raw materials with the length of 1-5 cm and the like.
Preferably, the solid-to-liquid ratio of the lignocellulose raw material to the ternary eutectic solvent in the step (1) is 1: 5-20, and preferably 1: 10-15.
Preferably, the lignocellulose raw material and the ternary eutectic solvent are mixed and heated according to the step (1) at the heating temperature of 100-140 ℃ for 5-120 minutes; the heating temperature is preferably 110-130 ℃, and the reaction time is 10-90 minutes.
Preferably, the acetone aqueous solution in the step (2) is 40-60% of acetone aqueous solution, and the adding amount is 1-5 times of the volume of the low ternary eutectic solvent, preferably 2-4 times.
Preferably, in the step (3), the primary extraction mixed solution is evaporated and concentrated until the water content is 30-50%, preferably 35-45%.
Preferably, the extraction in the step (3) is carried out by using an organic solvent, specifically, the added organic solvent is one of 2-methyltetrahydrofuran, tetrahydrofuran and 1, 4-dioxane, and the added amount is 30-300% (V/V), preferably 100-200% (V/V) of the low ternary eutectic solvent.
Preferably, the extract in the step (4) is concentrated to 10-50% of the volume of the total organic solvent added.
The technical scheme of the invention has the following beneficial effects: the invention provides a method for quickly separating lignin with a green solvent at high yield, which has the advantages of low cost, high efficiency, greenness and low energy consumption, and can efficiently separate most of lignin in biomass. The obtained lignin can be dissolved in a large amount of common organic solvents, and is very favorable for subsequent utilization. The method has the advantages of simple and convenient process operation, low cost and environmental friendliness. The whole operation process does not use toxic, harmful or difficultly recycled reagents. The low ternary eutectic solvent has less added water, and is easy to recover and separate, and the novel separation process has environment and economic feasibility. Experiments show that the yield of the lignin in the method is more than 77 percent, even more than 87 percent.
Drawings
FIG. 1 is a graph comparing cellulose enzymatic hydrolysis of lignin with lignin obtained by the method of example 2 of the present invention.
Detailed Description
The present invention is described in detail below by way of specific examples. Before the description is made, it should be understood that the terms used in the present specification and the appended claims should not be construed as limited to general and dictionary meanings, but interpreted based on the meanings and concepts corresponding to technical aspects of the present invention on the basis of the principle that the inventor is allowed to define terms appropriately for the best explanation. Accordingly, the description proposed herein is just a preferable example for the purpose of illustrations only, not intended to limit the scope of the invention, so it should be understood that other equivalents and modifications could be made thereto without departing from the spirit and scope of the invention.
The eutectic solvent selectively cleaves ether bonds, has good solubility for lignin in the lignocellulosic components, and relatively limited solubility for cellulose. In the step (4) of the preparation method, the temperature range of the eutectic solvent is 100-140 ℃ when the lignin is extracted. When the extraction temperature is lower than 100 ℃, the dissolved lignin is limited, and the effective separation of the lignin is difficult to realize; when the extraction temperature is higher than 140 ℃, the concentration of dissolved lignin is seriously condensed, and the loss of cellulose is too high, so that the subsequent utilization is not facilitated.
The following examples are given by way of illustration of embodiments of the invention and are not to be construed as limiting the invention, and it will be understood by those skilled in the art that modifications may be made without departing from the spirit and scope of the invention. Unless otherwise specified, reagents and equipment used in the following examples are commercially available products.
Example 1
Mixing the raw materials in a ratio of 1: 2: choline chloride, glyoxylic acid and p-toluenesulfonic acid are weighed in a molar ratio of 0.05 and put in a three-neck flask, the three-neck flask is heated and stirred at the temperature of 60 ℃ to obtain a homogeneous transparent liquid, namely a eutectic solvent (DES), and the liquid is cooled to room temperature and then stored in a dryer. Weighing 2.00 g of Danhong poplar wood powder (40-60 meshes) and 20 ml of DES, adding into a three-neck flask, reacting at 120 ℃ for 20 minutes, pouring the slurry into 60 ml of 50% acetone aqueous solution after the reaction is finished, stirring at normal temperature for 3 hours, and centrifuging to obtain residue I and supernatant I. Washing the residue I until the washing liquid is colorless, combining the supernatant I and the washing liquid, and concentrating to 30 ml. 15 ml of tetrahydrofuran was added to the concentrated solution, and extraction was repeated three times. Then combining the extract liquid, concentrating to 15 ml, adding 150 ml of saturated saline solution, stirring overnight to separate out solid, and freeze-drying the solid obtained by filtering to obtain lignin, wherein the recovery mass of the lignin is 0.3240 g. And performing infrared spectrum analysis on the obtained product, and comparing the infrared spectrum of the obtained product with the cellulose enzymatic lignin with a natural structure to determine that the obtained product is the lignin.
The poplar components comprise 55.3% of cellulose, 16.8% of hemicellulose and 20.2% of lignin. The lignin yield calculation formula is as follows: lignin yield (%) — isolated lignin mass (g)/(wood flour feedstock mass (g) × lignin content (%) × 100. From this, the yield of lignin was 80.2%.
Example 2
Mixing the raw materials in a ratio of 1: 2: choline chloride, glyoxylic acid and p-toluenesulfonic acid are weighed in a molar ratio of 0.03 and put into a three-neck flask, the three-neck flask is heated and stirred at the temperature of 60 ℃ to obtain a homogeneous transparent liquid, namely a eutectic solvent (DES), and the liquid is cooled to room temperature and then stored in a dryer. Weighing 2.00 g of Danhong poplar wood powder (40-60 meshes) and 20 ml of DES, adding into a three-neck flask, reacting at 120 ℃ for 120 minutes, pouring the slurry into 60 ml of 50% acetone aqueous solution after the reaction is finished, stirring at normal temperature for 3 hours, and centrifuging to obtain residue I and supernatant I. Washing the residue I until the washing liquid is colorless, combining the supernatant I and the washing liquid, and concentrating to 30 ml. 15 ml of tetrahydrofuran was added to the concentrated solution, and extraction was repeated three times. Then combining the extract liquid, concentrating to 15 ml, adding 150 ml of saturated salt solution, stirring overnight to separate out solid, carrying out freeze drying on the solid obtained by filtering to obtain lignin, weighing the lignin with the recovery mass of 0.3333g, and calculating to obtain the lignin yield of 82.5%.
Example 3
Mixing the raw materials in a ratio of 1: 2: choline chloride, glyoxylic acid and p-toluenesulfonic acid are weighed in a molar ratio of 0.05 and put in a three-neck flask, the three-neck flask is heated and stirred at the temperature of 60 ℃ to obtain a homogeneous transparent liquid, namely a eutectic solvent (DES), and the liquid is cooled to room temperature and then stored in a dryer. Weighing 2.00 g of Danhong poplar wood powder (40-60 meshes) and 20 ml of DES, adding into a three-neck flask, reacting at 100 ℃ for 120 minutes, pouring the slurry into 60 ml of 50% acetone aqueous solution after the reaction is finished, stirring at normal temperature for 3 hours, and centrifuging to obtain residue I and supernatant I. Washing the residue I until the washing liquid is colorless, combining the supernatant I and the washing liquid, and concentrating to 50 ml. 20 ml of tetrahydrofuran was added to the concentrated solution, and extraction was repeated three times. Then combining the extract liquid and concentrating to 30 ml, adding 300 ml of saturated salt solution, stirring overnight to separate out solid, freezing and drying the obtained solid by filtration to obtain lignin, weighing the lignin with the recovery mass of 0.3171g, and calculating to obtain the yield of the lignin of 78.5%.
Example 4
Mixing the raw materials in a ratio of 1: 2: weighing choline chloride, pyruvic acid and p-toluenesulfonic acid in a molar ratio of 0.10, placing in a three-neck flask, heating and stirring at 60 ℃ to obtain a homogeneous transparent liquid, namely a eutectic solvent (DES), cooling to room temperature, and storing in a dryer. Weighing 2.00 g of Danhong poplar wood powder (40-60 meshes) and 20 ml of DES, adding into a three-neck flask, reacting at 100 ℃ for 60 minutes, pouring the slurry into 60 ml of 50% acetone aqueous solution after the reaction is finished, stirring at normal temperature for 3 hours, and centrifuging to obtain residue I and supernatant I. Washing the residue I until the washing liquid is colorless, combining the supernatant I and the washing liquid, and concentrating to 30 ml. 20 ml of tetrahydrofuran was added to the concentrated solution, and extraction was repeated three times. And then combining the extract liquid, concentrating to 30 ml, adding the extract liquid into 300 ml of saturated saline salt water, stirring overnight to separate out solid, and freeze-drying the solid obtained by filtering to obtain lignin, wherein the recovery mass of the lignin is 0.3458g, and the yield of the lignin is 85.6 percent by calculation.
Example 5
Mixing the raw materials in a ratio of 1: 2: weighing choline chloride, pyruvic acid and p-toluenesulfonic acid according to the molar ratio of 0.08, placing the choline chloride, the pyruvic acid and the p-toluenesulfonic acid in a three-neck flask, heating and stirring the three-neck flask at the temperature of 60 ℃ to obtain a homogeneous transparent liquid, namely a eutectic solvent (DES), cooling the liquid to room temperature, and storing the liquid in a dryer. Weighing 2.00 g of Danhong poplar wood powder (40-60 meshes) and 20 ml of DES, adding into a three-neck flask, reacting at 100 ℃ for 60 minutes, pouring the slurry into 60 ml of 50% acetone aqueous solution after the reaction is finished, stirring at normal temperature for 3 hours, and centrifuging to obtain residue I and supernatant I. Washing the residue I until the washing liquid is colorless, combining the supernatant I and the washing liquid, and concentrating to 30 ml. 20 ml of 2-methyltetrahydrofuran was added to the concentrated solution, and extraction was repeated three times. Then combining the extract liquid, concentrating to 30 ml, adding 300 ml of saturated saline solution, stirring overnight to separate out solid, carrying out freeze drying on the solid obtained by filtering to obtain lignin, weighing the lignin with the recovery mass of 0.3135g, and calculating to obtain the yield of the lignin of 77.6%.
Example 6
Mixing the raw materials in a ratio of 1: 5: choline chloride, glyoxylic acid and p-toluenesulfonic acid are weighed in a molar ratio of 0.05 and put in a three-neck flask, the three-neck flask is heated and stirred at the temperature of 60 ℃ to obtain a homogeneous transparent liquid, namely a eutectic solvent (DES), and the liquid is cooled to room temperature and then stored in a dryer. Weighing 2.00 g of Danhong poplar wood powder (40-60 meshes) and 20 ml of DES, adding into a three-neck flask, reacting at 110 ℃ for 30 minutes, pouring the slurry into 60 ml of 50% acetone aqueous solution after the reaction is finished, stirring at normal temperature for 3 hours, and centrifuging to obtain residue I and supernatant I. Washing the residue I until the washing liquid is colorless, combining the supernatant I and the washing liquid, and concentrating to 30 ml. 20 ml of 1, 4-dioxane was added to the concentrated solution, and extraction was repeated three times. And then combining the extract liquid, concentrating to 30 ml, adding the extract liquid into 300 ml of saturated saline salt water, stirring overnight to separate out solid, and freeze-drying the solid obtained by filtering to obtain lignin, wherein the recovery mass of the lignin is 0.3523g, and the yield of the lignin is 87.2% by calculation.
Comparative example
To study the advantages of the present invention, the enzymatic lignin prior art method was compared to the present method.
The method in the prior art is used for hydrolyzing lignin by using cellulose, and comprises the following specific steps: and ball-milling the poplar powder for 8 hours by using a planetary ball mill. Ball milling conditions: 10g of the raw material was placed in a 500mL zirconia pot and the ball milling frequency was 450 rpm. Placing ball-milled wood powder into a plurality of 250mL conical flasks according to 1g/50mL acetate buffer solution with the pH value of 4.8, and then carrying out enzymolysis for 72h in a constant-temperature air shaking table at the set rotating speed of 150rpm and the temperature of 48 ℃, wherein the dosage of the commercial cellulase is 50FPU/g substrate, and the dosage of the hemicellulase is 50IU/g substrate. Under the condition of normal temperature, the obtained enzymolysis residues are stirred (500rpm) and extracted for 3 days by 96 percent dioxane (solid-liquid ratio is 1: 20, g/mL), the solvent is changed every 24 hours, and the supernatant fluid 1 and the residue 1 are respectively obtained by centrifugation. The resulting supernatant 1 was rotary evaporated to 30 ml and the concentrate was slowly added to 300 ml of deionized water and stirred at 500rpm overnight. After centrifugal separation, the solid residue obtained is dried to obtain Cellulolytic Enzyme Lignin (CEL), the extraction rate of lignin is about 30%.
Comparative is inventive example 2.
The results of comparison of the two methods described above by infrared spectroscopy are shown in FIG. 1. As can be seen from FIG. 1, the characteristic peaks 1600, 1504 and 1460cm of the isolated product-1The lignin is basically consistent with the characteristic peak of the enzymatic hydrolysis lignin, and the product separated by the method is the lignin.
Claims (10)
1. A method for separating lignin from green solvent rapidly at high yield comprises the following steps:
(1) mixing and heating a lignocellulose raw material and a ternary eutectic solvent to obtain slurry;
the preparation method of the ternary eutectic solvent comprises the following steps: mixing the first hydrogen bond donor, the second hydrogen bond donor and the hydrogen bond acceptor, heating for 1-3 hours at 50-70 ℃, and stirring at the frequency of 300-; preferably, the mixture is heated for 1.5 to 2.5 hours at the temperature of between 55 and 65 ℃, and the stirring frequency is 400 to 600 revolutions per minute;
the hydrogen bond receptor can be one or more of choline oxide, choline chloride, betaine or salt compounds which have positive charges and can be combined with negatively charged hydroxyl groups to form coordinate bonds;
the first hydrogen bond donor is a carboxylic acid substance, and the second hydrogen bond donor is a strong acid substance containing a benzene ring;
(2) adding an acetone aqueous solution into the slurry obtained in the step (1), stirring, filtering to obtain a filtrate, preferably washing residues with the acetone aqueous solution, and combining the filtrate and a washing solution to obtain a primary extraction mixed solution;
(3) evaporating and concentrating the filtrate or the primary extraction mixed solution, and extracting the filtrate or the primary extraction mixed solution, wherein preferably the extraction is repeated for two to four times;
(4) concentrating the extract obtained in the step (3), dropwise adding the concentrate into vigorously stirred saturated salt solution for regeneration, and then filtering to obtain solid residues; preferably, the solid is precipitated by adding saturated saline and stirring overnight.
2. The method of claim 1, further comprising freeze drying the solid residue.
3. The method of claim 1, wherein the molar ratio of the first hydrogen bond donor, the second hydrogen bond donor, and the hydrogen bond acceptor in step (1) is 0.01-0.10: 2-10: 1; preferably, the molar ratio is in the range of 0.01 to 0.10:2 to 10:1, and more preferably in the range of 0.01 to 0.05:2: 1.
4. The method of claim 1, wherein the hydrogen bond acceptor in step (1) is selected from one of choline oxide, choline chloride, and betaine; the first hydrogen bond donor is selected from formic acid, acetic acid, oxalic acid, malonic acid, glyoxylic acid and pyruvic acid; the second hydrogen bond donor is selected from p-hydroxybenzene sulfonic acid or p-toluenesulfonic acid.
5. The method of claim 1, wherein the lignocellulosic feedstock in step (1) is selected from the group consisting of softwood, hardwood, bamboo, or grass-type feedstocks; in the step (1), the solid-to-liquid ratio of the lignocellulose raw material to the ternary eutectic solvent is 1: 5-20, preferably 1: 10 to 15.
6. The method according to claim 1, wherein the lignocellulose raw material and the ternary eutectic solvent are mixed and heated in the step (1) at the heating temperature of 100-140 ℃ for 5-120 minutes; the heating temperature is preferably 110-130 ℃, and the treatment time is 60-90 minutes.
7. The method according to claim 1, wherein the acetone aqueous solution in the step (2) is 40-60% of acetone aqueous solution, and the addition amount is 1-5 times, preferably 2-4 times of the volume of the low ternary eutectic solvent.
8. The method according to claim 1, wherein the primary extraction mixture is evaporated and concentrated in step (3) to a water content of 30-50%, preferably 35-45%.
9. The method of claim 1, wherein the extraction in step (3) is performed with an organic solvent, specifically, the organic solvent is one of 2-methyltetrahydrofuran, tetrahydrofuran and 1, 4-dioxane, and is added in an amount of 30-300% (V/V), preferably 100-200% (V/V) of the low ternary eutectic solvent.
10. The method of claim 1, wherein in step (hi), the extract is concentrated to 10-50% by volume of the total organic solvent added; further comprises freeze-drying the solid obtained by filtering.
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| CN115232176A (en) * | 2022-07-14 | 2022-10-25 | 华南理工大学 | Method for extracting lignin by using ternary eutectic solvent |
| CN115678036A (en) * | 2022-10-14 | 2023-02-03 | 华南理工大学 | Method for extracting light-colored lignin based on ternary eutectic solvent |
| CN115678036B (en) * | 2022-10-14 | 2023-09-22 | 华南理工大学 | Method for extracting light-colored lignin based on ternary eutectic solvent |
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