CN107337585B - Method for preparing monophenol compounds by microwave depolymerization of lignin - Google Patents
Method for preparing monophenol compounds by microwave depolymerization of lignin Download PDFInfo
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- 229920005610 lignin Polymers 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000002245 particle Substances 0.000 claims abstract description 29
- 238000012691 depolymerization reaction Methods 0.000 claims abstract description 27
- 238000004821 distillation Methods 0.000 claims abstract description 22
- 239000012495 reaction gas Substances 0.000 claims abstract description 19
- 238000004227 thermal cracking Methods 0.000 claims abstract description 17
- 229910010271 silicon carbide Inorganic materials 0.000 claims abstract description 16
- 239000007789 gas Substances 0.000 claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 239000012159 carrier gas Substances 0.000 claims abstract description 13
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 monophenol compound Chemical class 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229920001732 Lignosulfonate Polymers 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- 229910021431 alpha silicon carbide Inorganic materials 0.000 claims description 4
- 229920005611 kraft lignin Polymers 0.000 claims description 4
- 239000005543 nano-size silicon particle Substances 0.000 claims description 4
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000197 pyrolysis Methods 0.000 description 7
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 229940015043 glyoxal Drugs 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
- C07C37/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing a monophenol compound by microwave depolymerization of lignin, which comprises the following steps of firstly, uniformly mixing 10 parts of lignin and 5-10 parts of silicon carbide particles in parts by mass, and placing the mixture in a microwave depolymerization reaction environment; secondly, continuously introducing mixed gas of carrier gas and reaction gas into the microwave depolymerization reaction environment, and starting to perform microwave depolymerization reaction; then cooling the thermal cracking steam generated by the microwave depolymerization reaction to obtain solvent type thermal cracking liquid; and finally, carrying out reduced pressure distillation on the solvent type thermal cracking liquid, and ending the reduced pressure distillation when no distillate is distilled, wherein the undistilled component is the monophenol compound. The method greatly improves the yield and the yield of the monophenol compounds by changing the reaction atmosphere, and provides an important technical support for efficiently converting lignin into the monophenol compounds.
Description
Technical Field
The invention belongs to the technical field of biomass energy, and particularly relates to a method for preparing monophenol compounds by microwave depolymerization of lignin.
Background
Lignin is one of the important constituents of biomass and is a renewable carbon source second to cellulose in abundance on earth. At present, the lignin is mainly industrial lignin, is a byproduct of the pulping and papermaking industry, the quantity of the lignin from the papermaking industry all the year around the world reaches more than 5000 ten thousand tons, the main utilization mode at present is to directly burn the lignin for heat supply, the utilization added value is very low, and a new way for high-value utilization of the lignin is urgently needed to be found.
The lignin has a structure comprising both carbon chains and aromatic rings, and is connected with methoxyl (-OCH)3) Hydroxyl (-OH), carboxyl (-CO) and other active functional group structures, and is an ideal raw material for producing high-value fine chemicals such as aromatic hydrocarbon, phenolic compounds and the like. The lignin can be degraded to a certain extent by means of thermochemical conversion, however, the thermochemical conversion and degradation of the lignin at the present stage have the problems of low degradation efficiency, serious carbonization phenomenon, low yield of conversion products, difficult product collection and the like, and the high-efficiency conversion and utilization of the lignin is severely restricted. Most of the current researches realize the degradation of lignin under the atmosphere of high pressure, high temperature and large amount of hydrogen, but the development of the technology is restricted by overhigh cost input and non-ideal product quality.
Disclosure of Invention
The invention aims to provide a method for preparing monophenol compounds by microwave depolymerization of lignin, which overcomes the defects in the prior art.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing monophenol compounds by microwave depolymerization of lignin comprises the following steps:
the method comprises the following steps: uniformly mixing 10 parts of lignin and 5-10 parts of silicon carbide particles in parts by mass, and placing the mixture in a microwave depolymerization reaction environment;
step two: continuously introducing mixed gas of carrier gas and reaction gas into a microwave depolymerization reaction environment, and starting to perform microwave depolymerization reaction;
step three: cooling thermal cracking steam generated by microwave depolymerization reaction to obtain solvent type thermal cracking liquid;
step four: and (3) carrying out reduced pressure distillation on the solvent type thermal cracking liquid, and ending the reduced pressure distillation when no distillate is distilled, wherein the undistilled component is the monophenol compound.
Further, the lignin is lignosulfonate, kraft lignin, alkali lignin, dealkalized lignin, hydrolyzed lignin or pyrolyzed lignin, the particle size of the lignin is 0.05-0.5 mm, and the water content is less than or equal to 10%.
Furthermore, the silicon carbide particles are nano silicon carbide particles, α -silicon carbide particles or β -silicon carbide particles, and the particle size of the silicon carbide particles is 0.1-1.0 mm.
Further, the flow rate of the mixed gas in the step two is as follows: and the flow rate of the mixed gas corresponding to the lignin in the step one per gram is 10-50 mL/min.
Furthermore, the carrier gas is nitrogen, the reaction gas is a mixture of hydrogen and organic vapor, the volume ratio of the hydrogen to the organic vapor is 1 (10-50), and the volume ratio of the carrier gas to the reaction gas is 10 (1-5).
Further, the organic vapor is methanol, ethanol, acetone, acetaldehyde, glyoxal, formic acid, diethyl ether or methyl formate.
Further, in the second step, the microwave depolymerization reaction conditions are as follows: the microwave frequency is 2.45GHz, the microwave power is 600-1200W, the heating temperature is 500-650 ℃, and the reaction time is 5-8 minutes.
Further, in the third step, the thermal cracking steam generated by the microwave depolymerization reaction is cooled at the condensation temperature of 1-5 ℃.
Furthermore, the reduced pressure distillation temperature in the fourth step is 20-35 ℃, and the relative vacuum degree is-0.085 to-0.095 Mpa.
Further, the distillate distilled out by the reduced pressure distillation in the fourth step is used as organic vapor for recycling in the second step after being vaporized again.
Compared with the prior art, the invention has the following beneficial technical effects:
the method for preparing the monophenol compound by microwave depolymerization of the lignin, which is provided by the invention, realizes the rapid and efficient depolymerization of the lignin, so that the monophenol compound prepared by depolymerization of the lignin reaches the theoretical yield, the utilization rate and the utilization value of the lignin are greatly improved, and the method has the following specific advantages:
(1) in addition, liquid products generated by the reaction by using nitrogen as the carrier gas are usually adhered to the wall of the reactor and cannot be well collected due to large viscosity and poor fluidity. The invention innovatively provides that the carrier gas and the reaction gas are mixed, the reaction gas well prevents secondary polycondensation of a monophenol intermediate generated by depolymerization on one hand, and the reaction gas is used as a solvent to carry the monophenol compound generated by the reaction out of a reaction system on the other hand, so that the collection efficiency is greatly improved.
(2) The invention provides a method for improving the yield of the lignin depolymerized into the monophenol compound by introducing mixed gas of carrier gas and reaction gas in the microwave depolymerization process; the reaction gas is a gas obtained by mixing hydrogen and organic steam, the volume ratio of the hydrogen in the reaction gas is relatively small, and the main function is to reduce the activation energy for breaking ether bonds and carbon-carbon bonds in lignin and assist in breaking the bonds; the organic vapor in the reaction gas is small molecular organic matter with lower boiling point, and the main function is that when ether bond and carbon-carbon bond in lignin are broken, the small molecular organic vapor can be grafted to two ends of broken bond rapidly, for example, methyl and hydroxyl in methanol are grafted to two ends of broken bond respectively, so as to prevent the broken bond from secondary polycondensation, thereby greatly improving the efficiency and conversion rate of lignin microwave depolymerization to generate monophenol compound.
(3) According to the invention, the organic vapor in the reaction gas is collected again in the condensation process, recovered through reduced pressure distillation, and gasified again for recycling as the organic vapor in the reaction gas, so that the efficiency of the organic vapor participating in the reaction is greatly improved, no waste liquid is discharged, and the process is clean and environment-friendly.
Detailed Description
Embodiments of the invention are described in further detail below:
aiming at the problems that the secondary polycondensation phenomenon of monophenol compound intermediates is serious, the conversion efficiency and the yield of monophenol compounds are low, the generated monophenol compounds are high in viscosity and easy to deposit on the tube wall to cause difficulty in collection and the like in the thermal conversion process of lignin at present, the invention provides a method for preparing the monophenol compounds by microwave depolymerization of the lignin, which comprises the following steps:
(1) uniformly mixing 10 parts by mass of lignin and 5-10 parts by mass of silicon carbide particles, and placing the mixture in a microwave depolymerization reaction environment, wherein the lignin is lignosulfonate, kraft lignin, alkali lignin, dealkalized lignin, hydrolyzed lignin or pyrolyzed lignin, the particle size is 0.05-0.5 mm, the water content is less than or equal to 10%, and the silicon carbide is nano silicon carbide, α -silicon carbide or β -silicon carbide, and the particle size is 0.1-1.0 mm.
(2) And continuously introducing mixed gas of carrier gas and reaction gas into the microwave reaction environment to start the microwave depolymerization reaction. The flow rate of the mixed gas is as follows: the flow rate of the mixed gas corresponding to each gram of lignin is 10-50 mL/min; the carrier gas is nitrogen, and the volume ratio of the carrier gas to the reaction gas is 10 (1-5); the reaction gas is a mixture of hydrogen and organic steam, the volume ratio of the hydrogen to the organic steam is 1 (10-50), wherein the organic steam is one of methanol, ethanol, acetone, acetaldehyde, glyoxal, formic acid, diethyl ether and methyl formate. The microwave depolymerization reaction conditions are microwave frequency of 2.45GHz, microwave power of 600-1200W, heating temperature of 500-650 ℃ and reaction time of 5-8 minutes.
(3) And cooling the thermal cracking steam generated by microwave depolymerization at a condensation temperature of 1-5 ℃ to obtain the solvent type thermal cracking liquid.
(4) And (3) carrying out reduced pressure distillation on the solvent type thermal cracking liquid, wherein the reduced pressure distillation temperature is 20-35 ℃, the relative vacuum degree is-0.085-0.095 Mpa, and when no distillate is distilled, the reduced pressure distillation is finished, and the undistilled component is the monophenol compound.
(5) The distillate distilled out above is re-vaporized and recycled for the organic vapor in step (2).
The present invention is described in further detail below with reference to examples:
example 1
The implementation process of the invention is described by taking alkali lignin as an example as follows:
10g of alkali lignin (particle size of 0.2-0.5 mm, water content of 8%) and 5g of nano silicon carbide particles (particle size of 0.1-0.45 mm) are uniformly mixed and subjected to microwave depolymerization reaction. And continuously introducing a mixed gas of 100mL/min nitrogen, 1mL/min hydrogen and 10mL/min methanol in the microwave depolymerization reaction, and starting to perform the microwave depolymerization reaction under the conditions of microwave frequency of 2.45GHz, microwave power of 600W, heating temperature of 500 ℃ and reaction time of 8 minutes. And cooling the thermal cracking steam generated by microwave depolymerization at a condensation temperature of 1 ℃ to obtain solvent type thermal cracking liquid. And (3) carrying out reduced pressure distillation on the solvent type thermal cracking liquid, wherein the reduced pressure distillation temperature is 20 ℃, the relative vacuum degree is-0.085 Mpa, and when no distillate is distilled, the reduced pressure distillation is finished, and the undistilled component is the monophenol compound. After weighing, the monophenolic compound accounts for 7.6g, and the yield reaches 76%; the molecular weight measurement range is concentrated at 95-179 Da, which indicates that the product is mainly monophenolic compounds.
Example 2
The implementation process of the invention is described by taking the pyrolysis lignin raw material as an example as follows:
uniformly mixing 10g of pyrolytic lignin (with the particle size of 0.05-0.1 mm and the water content of 3%) and 10g of α -silicon carbide particles (with the particle size of 0.45-1.0 mm), carrying out microwave depolymerization reaction, continuously introducing mixed gas of 300mL/min nitrogen, 3mL/min hydrogen and 150mL/min acetaldehyde into the microwave depolymerization reaction, and starting to carry out microwave depolymerization reaction under the conditions of microwave frequency of 2.45GHz, microwave power of 1200W, heating temperature of 650 ℃ and reaction time of 5 minutes, cooling pyrolysis steam generated by microwave depolymerization at the condensation temperature of 5 ℃ to obtain solvent type pyrolysis liquid, carrying out reduced pressure distillation on the solvent type pyrolysis liquid at the reduced pressure distillation temperature of 35 ℃ and relative vacuum degree of-0.095 MPa, wherein when no distillate exists, the reduced pressure distillation is finished, the components which are not obtained are monophenol compounds, weighing the monophenol compounds, wherein the yield reaches 68%, and the molecular weight determination range is concentrated on 95-131 Da, and the product is mainly monophenol compounds.
Example 3
The implementation process of the invention is described by taking lignosulfonate as an example as follows:
uniformly mixing 10g of lignosulfonate (with the particle size of 0.1-0.3 mm and the water content of 5%) and 8g of β -silicon carbide particles (with the particle size of 0.45-0.6 mm), carrying out microwave depolymerization reaction, continuously introducing a mixed gas of 200mL/min nitrogen, 2mL/min hydrogen and 50mL/min methyl formate in the microwave depolymerization reaction, starting to carry out microwave depolymerization reaction under the conditions of microwave frequency of 2.45GHz, microwave power of 1000W, heating temperature of 550 ℃ and reaction time of 6 minutes, cooling pyrolysis steam generated by microwave depolymerization at the condensation temperature of 3 ℃ to obtain a solvent type pyrolysis liquid, carrying out reduced pressure distillation on the solvent type pyrolysis liquid at the reduced pressure distillation temperature of 30 ℃ and the relative vacuum degree of-0.090 MPa, finishing the reduced pressure distillation when no distillate exists, wherein the components which are not obtained are monophenol compounds, weighing the monophenol compounds, wherein the yield reaches 73%, and the molecular weight determination range is concentrated in 110-184 Da, and the product is mainly monophenol compounds.
The lignin in the above embodiments may also be kraft lignin, dealkalized lignin or hydrolyzed lignin; the organic vapor may also be ethanol, acetone, glyoxal, formic acid, or diethyl ether.
Claims (5)
1. The method for preparing monophenol compounds by microwave depolymerization of lignin is characterized by comprising the following steps:
the method comprises the following steps: uniformly mixing 10 parts of lignin and 5-10 parts of silicon carbide particles in parts by mass, and placing the mixture in a microwave depolymerization reaction environment, wherein the lignin is lignosulfonate, kraft lignin, alkali lignin, dealkalized lignin, hydrolyzed lignin or pyrolyzed lignin, the particle size of the lignin is 0.05-0.5 mm, and the water content is less than or equal to 10%;
step two: continuously introducing mixed gas of carrier gas and reaction gas into a microwave depolymerization reaction environment, wherein the flow of the mixed gas corresponding to lignin in the first step is 10-50 mL/min per gram, starting to perform microwave depolymerization reaction, the carrier gas is nitrogen, the reaction gas is gas obtained by mixing hydrogen and organic vapor, the volume ratio of the hydrogen to the organic vapor is 1 (10-50), the volume ratio of the carrier gas to the reaction gas is 10 (1-5), the organic vapor is methanol, acetaldehyde or methyl formate, and the microwave depolymerization reaction conditions are as follows: the microwave frequency is 2.45GHz, the microwave power is 600-1200W, the heating temperature is 500-650 ℃, and the reaction time is 5-8 minutes;
step three: cooling thermal cracking steam generated by microwave depolymerization reaction to obtain solvent type thermal cracking liquid;
step four: and (3) carrying out reduced pressure distillation on the solvent type thermal cracking liquid, and ending the reduced pressure distillation when no distillate is distilled, wherein the undistilled component is the monophenol compound.
2. The method for preparing monophenolic compounds through microwave depolymerization of lignin according to claim 1, wherein silicon carbide particles are nano silicon carbide particles, α -silicon carbide particles or β -silicon carbide particles, and the particle size of the silicon carbide particles is 0.1-1.0 mm.
3. The method for preparing monophenolic compounds through microwave depolymerization of lignin according to claim 1, wherein in the third step, thermal cracking steam generated through microwave depolymerization is cooled at a condensation temperature of 1-5 ℃.
4. The method for preparing monophenol compounds from lignin by microwave depolymerization according to claim 1, wherein the reduced pressure distillation temperature in step four is 20-35 ℃, and the relative vacuum degree is-0.085-0.095 Mpa.
5. The method for preparing monophenolic compounds by microwave depolymerization of lignin according to claim 1, wherein the distillate distilled from the vacuum distillation in the fourth step is re-vaporized and recycled as organic vapor for the second step.
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| CN110407888B (en) * | 2019-08-09 | 2020-11-06 | 陕西科技大学 | Method for promoting depolymerization of sulfate lignin by using waste cigarette filter tip |
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