CN114105739A - Green alkali lignin micromolecule separation method and product - Google Patents
Green alkali lignin micromolecule separation method and product Download PDFInfo
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Abstract
The invention discloses a green alkali lignin micromolecule separation method and a product; adding water or ethanol/water into black liquor for dilution, performing centrifugal treatment, and performing self-hydrolysis reaction on supernate to obtain hydrolysate; and cooling the hydrolysate, acidifying, standing and centrifuging, extracting the obtained filtrate by using a green organic solvent, and drying to obtain a soluble micromolecule fraction, namely the alkali lignin micromolecules. The method extracts and utilizes the lignin in the alkaline pulping black liquor of an alkaline method, a sulfate method and the like, and has the characteristics of waste utilization, environmental protection, high economic benefit and the like; the method can obtain lignin fractions with different molecular weights, and the polydispersity of each fraction is reduced, and small molecular fractions can be selectively dissolved out; the separation method is environment-friendly, the solvent is non-toxic, the content of the small molecular fraction is rich, the whole process is environment-friendly, and the method has a good industrial production prospect.
Description
Technical Field
The invention relates to the technical field of lignin pretreatment and the technical field of lignin recycling, in particular to a green alkali lignin micromolecule separation method and a product.
Background
The industrial alkali lignin is an important industrial raw material, has good flame retardance, oxidation resistance, thermal stability and the like, and has good application potential in the fields of high polymer materials, carbon materials, adhesives, water reducing agents and the like due to the fact that molecules contain various active functional groups. Currently, industrial alkali lignin is mainly extracted from black liquor generated in the cooking process of the pulping and papermaking industry, and a large amount of lignin micromolecule degradation products are contained in the industrial alkali lignin. Research reports that the methylene dichloride is adopted to classify the crude lignin extracted from the black liquor, so that high-yield lignin small molecular fractions can be obtained, and the small molecular fractions contain a large amount of monomers, dimers and the like, so that the method has important significance for developing and utilizing new materials and chemicals. Although dichloromethane is more selective for small molecule fractions, it is more toxic and unfavorable for subsequent production (C.ZHao, Z.Hu, L.Shi, C.Wang, F.Yue, S.Li, H.Zhang, F.Lu, Green Chem 2020,22, 7366-.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to realize the fractional separation of lignin micromolecule fraction with considerable content from black liquor by adopting a green and efficient self-hydrolysis grading method and combining a green solvent system, so as to replace the traditional solvent system with high selectivity and high toxicity and realize the efficient utilization of lignin.
A large amount of alkali liquor can be remained in the pulping black liquor of an alkaline method and a sulfate method, so that the residual alkali liquor can be utilized to perform self-hydrolysis reaction at high temperature to realize classification, in the process, the bonds which are not completely broken in the lignin are further broken to form fragment products with low molecular weight, and then the lignin micromolecule fraction with relatively high yield is obtained by green organic solvent extraction. The whole process is green and nontoxic, is expected to replace dichloromethane with high toxicity, directly extracts lignin micromolecule fractions from black liquor, realizes effective utilization of lignin, and has important significance from the environmental protection perspective and the economic perspective.
In order to achieve the purpose, the invention adopts the following technical scheme:
a green alkali lignin micromolecule separation method and a product thereof comprise the following steps:
(1) self-hydrolysis reaction: adding water or ethanol/water into the black liquor for dilution, performing centrifugal treatment, and performing self-hydrolysis reaction on supernatant to obtain hydrolysate;
(2) alkali lignin micromolecule separation: and (2) cooling the hydrolysate obtained in the step (1), acidifying, standing and centrifuging, extracting the obtained filtrate with a green organic solvent, and drying to obtain a soluble micromolecule fraction, namely the alkali lignin micromolecules.
Further, the black liquor in the step (1) is black liquor generated in a cooking stage in an alkaline pulping process.
Further preferably, the alkaline pulping process is an alkaline pulping process or a sulfate pulping process.
Further, the dilution quality of the step (1) is 5-15 times of that of the black liquor.
Further, the volume ratio of ethanol to water in the ethanol/water in the step (1) is 0-5: 1 and is not 0; further preferably, the volume ratio of ethanol to water in the ethanol/water in the step (1) is 1:5, 1:1, 5: 1.
Further, the reaction in the step (1) is carried out in a high-pressure reaction kettle.
Further, the temperature of the reaction in the step (1) is 90-140 ℃.
Further, the reaction time of the step (1) is 1-4 h.
Further, the acidification in the step (2) uses hydrochloric acid with the acid concentration of 0.1-6 mol/L; the acidification is to pH < 3.
Further, the standing time in the step (2) is 4-16 h. Further preferably, the standing time is 12 hours.
Further, the organic solvent in the step (2) is ethyl acetate.
Further, the extraction times in the step (2) are 1-5 times.
Further, the solvent removing condition in the step (2) is that the solvent is evaporated to dryness under reduced pressure at the temperature of 30-60 ℃.
The alkali lignin micromolecules obtained by the green alkali lignin micromolecule separation method are separated.
Compared with the prior art, the invention has the following advantages:
(1) the method utilizes the characteristic that a large amount of alkali liquor is remained in alkaline pulping black liquor such as an alkaline method and a sulfate method, and adopts a simple, green and low-cost self-hydrolysis method combined with a green organic solvent extraction method to reduce lignin heterogeneity, thereby improving the utilization rate of lignin wastes with rich content.
(2) The invention utilizes the autohydrolysis reaction to further break the connecting bond in the lignin, form fragments with lower molecular weight and improve the yield of small molecular fraction.
(3) The solvent selected by the method is green and nontoxic, is expected to replace the traditional toxic solvent with high selectivity on small molecule level, and is an economic and sustainable method.
Drawings
FIG. 1 is a GC-MS graph of the small molecular fraction of eucalyptus kraft lignin from example 1.
FIG. 2 is a GC-MS graph of the small molecular fraction of eucalyptus kraft lignin from example 2.
FIG. 3 is a GC-MS graph of the small molecular fraction of eucalyptus kraft lignin from example 3.
FIG. 4 is a GC-MS graph of the small molecular fraction of eucalyptus kraft lignin from example 4.
FIG. 5 is a GC-MS graph of the eucalyptus sulphate lignin small molecule fraction of example 5 (blank).
FIG. 6 is a structural view of each substance in each example.
Detailed Description
The present invention will be described in further detail below with reference to examples for better understanding of technical features of the present invention, but the scope of the present invention as claimed is not limited thereto.
Example 1
A green alkali lignin small molecule separation method comprises the following steps:
(1) taking 10g of black liquor sample generated in the cooking stage in the eucalyptus kraft pulping process, adding 60mL of distilled water for dilution, carrying out centrifugal treatment (8000r/min, 15min), and carrying out self-hydrolysis reaction on the supernatant in a reaction kettle at the temperature of 120 ℃ for 3h to obtain hydrolysate;
(2) cooling the hydrolysate, acidifying with 1mol/L hydrochloric acid until pH is less than 3, standing for 12h, centrifuging (8000r/min, 15min), separating the residue from the filtrate, and washing the residue with deionized water for 2 times;
(3) combining the filtrates obtained in step (2), extracting with ethyl acetate for 3 times, evaporating the organic phase at 40 deg.C under reduced pressure to remove ethyl acetate, and vacuum drying at 40 deg.C (overnight) to obtain soluble fraction (eucalyptus sulfate lignin small molecule fraction); the filter residue was dried under vacuum (overnight) at 40 ℃ to give an insoluble fraction.
The GC-MS diagram of the obtained eucalyptus sulfate lignin small molecular fraction is shown in figure 1.
The yield of the obtained small molecular fraction of the eucalyptus sulfate lignin is 20.7%.
Example 2
A green alkali lignin small molecule separation method comprises the following steps:
(1) taking 10g of black liquor sample generated in the cooking stage in the eucalyptus sulfate pulping process, adding 50mL of distilled water and 10mL of ethanol for dilution, carrying out centrifugal treatment (8000r/min, 15min), and carrying out self-hydrolysis reaction on the supernatant in a reaction kettle at the temperature of 120 ℃ for 3h to obtain hydrolysate;
(2) cooling the hydrolysate, acidifying with 1mol/L hydrochloric acid until pH is less than 3, standing for 12h, centrifuging (8000r/min, 15min), separating the residue from the filtrate, and washing the residue with deionized water for 2 times;
(3) combining the filtrates obtained in step (2), extracting with ethyl acetate for 3 times, evaporating the organic phase at 40 deg.C under reduced pressure to remove ethyl acetate, and vacuum drying at 40 deg.C (overnight) to obtain soluble fraction (eucalyptus sulfate lignin small molecule fraction); the filter residue was dried under vacuum (overnight) at 40 ℃ to give an insoluble fraction.
The GC-MS chart of the obtained eucalyptus sulfate lignin small molecular fraction is shown in figure 2.
The yield of the obtained small molecular fraction of the eucalyptus sulfate lignin is 29.8%.
Example 3
A green alkali lignin small molecule separation method comprises the following steps:
(1) taking 10g of black liquor sample generated in the cooking stage in the eucalyptus sulfate pulping process, adding 30mL of distilled water and 30mL of ethanol for dilution, carrying out centrifugal treatment (8000r/min, 15min), and carrying out self-hydrolysis reaction on the supernatant in a reaction kettle at the temperature of 120 ℃ for 3h to obtain hydrolysate;
(2) cooling the hydrolysate, acidifying with 1mol/L hydrochloric acid until pH is less than 3, standing for 12h, centrifuging (8000r/min, 15min), separating the residue from the filtrate, and washing the residue with deionized water for 2 times;
(3) combining the filtrates obtained in step (2), extracting with ethyl acetate for 3 times, evaporating the organic phase at 40 deg.C under reduced pressure to remove ethyl acetate, and vacuum drying at 40 deg.C (overnight) to obtain soluble fraction (eucalyptus sulfate lignin small molecule fraction); the filter residue was dried under vacuum (overnight) at 40 ℃ to give an insoluble fraction.
The GC-MS chart of the obtained eucalyptus sulfate lignin small molecular fraction is shown in figure 3.
The yield of the obtained small molecular fraction of the eucalyptus sulfate lignin is 41.1%.
Example 4
A green alkali lignin small molecule separation method comprises the following steps:
(1) taking 10g of black liquor sample generated in the cooking stage in the eucalyptus sulfate pulping process, adding 10mL of distilled water and 50mL of ethanol for dilution, carrying out centrifugal treatment (8000r/min, 15min), and carrying out self-hydrolysis reaction on the supernatant in a reaction kettle at the temperature of 120 ℃ for 3h to obtain hydrolysate;
(2) cooling the hydrolysate, acidifying with 1mol/L hydrochloric acid until pH is less than 3, standing for 12h, centrifuging (8000r/min, 15min), separating the residue from the filtrate, and washing the residue with deionized water for 2 times;
(3) combining the filtrates obtained in step (2), extracting with ethyl acetate for 3 times, evaporating the organic phase at 40 deg.C under reduced pressure to remove ethyl acetate, and vacuum drying at 40 deg.C (overnight) to obtain soluble fraction (eucalyptus sulfate lignin small molecule fraction); the filter residue was dried under vacuum (overnight) at 40 ℃ to give an insoluble fraction.
The GC-MS chart of the obtained eucalyptus sulfate lignin small molecular fraction is shown in figure 4.
The yield of the obtained eucalyptus kraft lignin micromolecule fraction is 52.5%.
Example 5
A green alkali lignin small molecule separation method comprises the following steps:
(1) taking 10g of black liquor sample generated in the cooking stage in the eucalyptus kraft pulping process, adding 60mL of distilled water for dilution, carrying out centrifugal treatment (8000r/min, 15min), acidifying the supernatant by 1mol/L hydrochloric acid until the pH value is less than 3, standing for 12h, centrifuging (8000r/min, 15min), separating filter residue from filtrate, and washing the filter residue by deionized water for 2 times;
(2) combining the filtrates obtained in step (1), extracting with ethyl acetate for 3 times, evaporating the organic phase at 40 deg.C under reduced pressure to remove ethyl acetate, and vacuum drying at 40 deg.C (overnight) to obtain soluble fraction (eucalyptus sulfate lignin small molecule fraction); the filter residue was dried under vacuum (overnight) at 40 ℃ to give an insoluble fraction.
The GC-MS chart of the obtained eucalyptus sulfate lignin small molecular fraction is shown in figure 5.
The yield of the obtained small molecular fraction of the eucalyptus sulfate lignin is 14.6%.
The structural diagrams of the substances are shown in fig. 6, and the substances have important roles in developing new materials and chemicals and have important guiding significance for identifying the structure of industrial lignin.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A green alkali lignin small molecule separation method is characterized by comprising the following steps:
(1) self-hydrolysis reaction: adding water or ethanol/water into the black liquor for dilution, performing centrifugal treatment, and performing self-hydrolysis reaction on supernatant to obtain hydrolysate;
(2) alkali lignin micromolecule separation: and (2) cooling the hydrolysate obtained in the step (1), acidifying, standing and centrifuging, extracting the obtained filtrate with a green organic solvent, and removing the solvent to obtain a soluble micromolecule fraction, namely the alkali lignin micromolecules.
2. The method for separating alkali lignin micromolecules in green according to claim 1, which is characterized in that: the black liquor in the step (1) is generated in the cooking stage in the alkaline pulping process.
3. The method for separating alkali lignin micromolecules in green color according to claim 2, which is characterized in that: the alkaline pulping process is an alkaline pulping process or a sulfate pulping process.
4. The method for separating alkali lignin micromolecules in green according to claim 1, which is characterized in that: the dilution quality of the step (1) is 5-15 times of that of the black liquor; the volume ratio of ethanol to water in the ethanol/water is 0-5: 1, and is not 0.
5. The method for separating alkali lignin micromolecules in green according to claim 1, which is characterized in that: the reaction temperature in the step (1) is 90-140 ℃.
6. The method for separating alkali lignin micromolecules in green according to claim 1, which is characterized in that: the reaction time in the step (1) is 1-4 h; the reaction is carried out in a high-pressure reaction kettle.
7. The method for separating alkali lignin micromolecules in green according to claim 1, which is characterized in that: the acidification in the step (2) uses hydrochloric acid with the acid concentration of 0.1-6 mol/L; the acidification is to pH < 3.
8. The method for separating alkali lignin micromolecules in green according to claim 1, which is characterized in that: and (3) standing for 4-16h in the step (2).
9. The method for separating alkali lignin micromolecules in green according to claim 1, which is characterized in that: the extraction times in the step (2) are 1-5 times; the organic solvent is ethyl acetate; the condition of removing the solvent in the step (2) is that the solvent is evaporated to dryness under reduced pressure at the temperature of 30-60 ℃.
10. The alkali lignin small molecule separated by the green alkali lignin small molecule separation method of any one of claims 1 to 9.
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