CN112979423B - Method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin - Google Patents
Method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin Download PDFInfo
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- CN112979423B CN112979423B CN202110188204.2A CN202110188204A CN112979423B CN 112979423 B CN112979423 B CN 112979423B CN 202110188204 A CN202110188204 A CN 202110188204A CN 112979423 B CN112979423 B CN 112979423B
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/04—Sulfides
- B01J27/047—Sulfides with chromium, molybdenum, tungsten or polonium
- B01J27/051—Molybdenum
- B01J27/0515—Molybdenum with iron group metals or platinum group metals
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
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- 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
- C07C37/005—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up
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Abstract
The invention discloses a method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin, which designs a microwave reaction body with a sandwich structure by compounding a microwave absorption medium, the lignin and a catalyst, greatly increases the contact area between the lignin and the catalyst and the microwave absorption medium, reduces the generation of side reactions, and has positive significance for the directional regulation and control mechanism control of converting the lignin into the high-value guaiacol and phenol.
Description
Technical Field
The invention belongs to the technical field of biomass energy and chemicals, and particularly relates to a method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin.
Background
Lignin is one of the important constituents of biomass and is the second most abundant biopolymer next to cellulose on earth. In addition to the vast reserves in nature, lignin is a major byproduct of the pulp and paper industry, which produces about 5000 million tons of lignin each year, but only about 2% of the lignin is separated for various products, most of which are discarded as waste, or heat and power are recovered by combustion, resulting in a great waste of resources. Also, it is imperative that lignin finds new high value added applications.
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. By thermalizationThe chemical conversion means can realize the degradation of lignin to a certain degree, however, the thermal chemical conversion degradation of lignin at the present stage has 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 are seriously restricted.
At present, most researches realize the degradation of lignin under the atmosphere of high pressure, high temperature and a large amount of hydrogen, but the development of the technology is restricted by overhigh cost investment and low controllability of product components, and liquid oil obtained by pyrolysis is often hundreds of types, thereby causing great obstacles to the purification and application of high-value components.
Disclosure of Invention
The invention aims to provide a method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin, which overcomes the defects in the prior art2The composite structure of the coating layer improves the controllability and yield of the lignin pyrolysis reaction, reduces the generation of side reactions in the pyrolysis process, obtains monophenol compounds mainly containing guaiacol and phenol, and provides important technical support for the efficient conversion of the lignin.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin comprises the following steps:
the method comprises the following steps: mixing glycine and Fe (NO)3)3·7H2Dissolving O in a mixed solution of ethanol and water, carrying out hydrothermal reaction, cooling to room temperature after the reaction is finished, washing with ethanol and distilled water for a plurality of times, and drying to obtain Fe2O3Nanospheres;
step two: dissolving lignin in tetrahydrofuran, and adding Fe obtained in the step one2O3The nanospheres are fully and uniformly stirred;
step three: placing the solution obtained in the step two in a dialysis bag with the cut-off molecular weight of 8000-48 hours later, core-shell type Fe was obtained2O3@ lignin, washing with anhydrous ethanol several times, and oven drying to obtain dry core-shell type Fe2O3@ lignin;
step four: adding ammonium molybdate and thiourea into deionized water, uniformly mixing, wherein the mass ratio of ammonium molybdate to thiourea is 1: 2-1: 5, the mass ratio of ammonium molybdate to deionized water is 1: 80-1: 150, stirring for 6 hours at 40-60 ℃, adding oxalic acid, and adjusting the pH value to 2 to obtain an acidic molybdenum-sulfur mixed solution;
step five: mixing dried core-shell Fe2O3Soaking @ lignin in the mixed solution of molybdenum and sulfur, and performing hydrothermal reaction to obtain Fe2O3@ lignin @ MoS2A composite material;
step six: mixing Fe2O3@ Lignin @ MoS2And carrying out microwave-assisted depolymerization reaction on the composite material in a nitrogen atmosphere, and collecting a liquid product to obtain liquid oil.
Further, glycine and Fe (NO) in step one3)3·7H2The mass ratio of O is 1: 5-1: 10, and the concentration of glycine in the mixed solution of ethanol and water is 3-6 g/L.
Further, the volume ratio of the ethanol to the water in the mixed solution of the ethanol and the water is 1: 2.
Further, after the lignin is dissolved in the tetrahydrofuran in the second step, the concentration of the obtained solution is 1-5 mg mL-1。
Further, Fe described in step two2O3The mass ratio of the nanospheres to the lignin is 1: (0.5-2).
Further, the lignin in the second step is one of alkali lignin, sulfate lignin and solvent lignin.
Further, in the third step, the drying temperature is 80-100 ℃, and the time is 12 hours.
Furthermore, the temperature of the hydrothermal reaction in the fifth step is 120-180 ℃ and the time is 24 hours.
Furthermore, the nitrogen flow rate in the sixth step is 400-600 mL/min.
Further, in the sixth step, the microwave-assisted depolymerization reaction is carried out at a power of 800-1000W and a temperature of 500-600 ℃ for 10-15 min.
Compared with the prior art, the invention has the following beneficial technical effects:
the method for preparing the guaiacol and the phenol by microwave-assisted depolymerization of the lignin, disclosed by the invention, realizes the rapid and efficient depolymerization of the lignin, improves the yield of the guaiacol and the phenol prepared by depolymerization of the lignin, has a positive promotion effect on improving the utilization rate and the utilization value of the lignin, and has the following specific advantages:
(1)MoS2the conversion rate of converting lignin into high-value guaiacol and phenol is improved by the coating structure of the lignin, the content of guaiacol and phenol in the obtained liquid oil product is higher under the same raw material usage amount and microwave pyrolysis condition, the utilization value and economic effect of the product are better, and the method has a positive effect on high-value utilization of lignin resources.
(2) In the preparation of Fe2O3@ Lignin @ MoS2In the composite material, a microwave reaction body with a sandwich structure is designed by compounding a microwave absorption medium, lignin and a catalyst, so that the heat transfer efficiency can be effectively improved, and the reaction time can be shortened; at the same time, Fe2O3And MoS2And the lignin microwave absorption material is a good microwave absorption medium, and can further improve the heat transfer efficiency and the reaction efficiency of the lignin microwave absorption material on lignin.
(3) Cocatalyst Fe2O3Main catalyst MoS2The combination of the lignin layer greatly increases the contact area between the lignin and the catalyst and the microwave absorption medium, reduces the generation of side reactions, is beneficial to the direct catalysis of a lignin cracking product by a surface catalyst, and improves the conversion efficiency of the lignin to guaiacol and phenol, so that a sandwich structure among the main catalyst, the lignin and the cocatalyst has positive significance for the directional regulation and control mechanism control of the conversion of the lignin to the guaiacol and the phenol with high value.
Detailed Description
The invention is further described below.
A method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin comprises the following steps:
the method comprises the following steps: mixing glycine and Fe (NO)3)3·7H2O is dissolved in a mixed solution of ethanol and water in a mass ratio of 1: 5-1: 10 (the volume ratio of ethanol to water is 1: 2), and the concentration of glycine in the mixed solution is 3-6 g/L. Carrying out hydrothermal reaction for 12 hours at 150-200 ℃. Cooling to room temperature, washing with ethanol and distilled water for 3-5 times, and drying in a drying oven at 50-80 ℃ for 6-8 hours to obtain Fe2O3Nanospheres;
step two: 1-5 mg mL of lignin-1Is dissolved in tetrahydrofuran, and then the Fe obtained above is added2O3Nanospheres, stirring well for 3 hours, said Fe2O3The mass ratio of the nanospheres to the lignin is 1: (0.5 to 2); the lignin is one of alkali lignin, sulfate lignin and solvent lignin.
Step three: placing the solution in a dialysis bag with the cut-off molecular weight of 8000-14000, placing the dialysis bag in deionized water, slowly stirring and dialyzing in a fume hood for 24-48 hours to obtain core-shell Fe2O3@ lignin. Washing with absolute ethyl alcohol for 4-6 times, and drying at 80-100 ℃ for 12h to obtain dry core-shell Fe2O3@ lignin;
step four: adding ammonium molybdate and thiourea into deionized water, uniformly mixing, wherein the mass ratio of ammonium molybdate to thiourea is 1: 2-1: 5, the mass ratio of ammonium molybdate to deionized water is 1: 80-1: 150, stirring for 6 hours at 40-60 ℃, adding oxalic acid, and adjusting the pH value to 2 to obtain an acidic molybdenum-sulfur mixed solution;
step five: mixing dried core-shell Fe2O3Immersing @ lignin in the mixed solution of acid Mo and S, and hydrothermal reacting at 120-180 deg.C for 24 hr to obtain Fe2O3@ Lignin @ MoS2A composite material;
step six: mixing Fe2O3@ woodTexel @ MoS2Placing the composite material in a microwave reactor, adjusting the power to 800-1000W under the nitrogen atmosphere of 400-600 mL/min, reacting at 500-600 ℃ for 10-15 min for microwave-assisted depolymerization reaction, and collecting a liquid product to obtain liquid oil.
The present invention will be described in detail with reference to examples. It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict.
The following detailed description is illustrative of the embodiments and is intended to provide further details of the invention. Unless otherwise defined, all technical terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention.
Example 1
3g of glycine and 15g of Fe (NO)3)3·7H2Dissolving O in 1000mL of mixture of ethanol and water (volume ratio of ethanol to water is 1: 2), performing hydrothermal reaction at 150 deg.C for 12 hr, cooling to room temperature, washing with ethanol and distilled water for 3 times, and drying in 50 deg.C drying oven for 8 hr to obtain Fe2O3Nanospheres; 1g of alkali lignin was dissolved in 1000mL of tetrahydrofuran, and 2g of Fe obtained above was added2O3The nanospheres are placed in a dialysis bag with the molecular weight cutoff of 8000 after being fully stirred for 3 hours, the dialysis bag is placed in deionized water, and the dialysis bag is slowly stirred and dialyzed for 24 hours in a fume hood to obtain core-shell Fe2O3Washing with absolute ethanol for 4 times, and drying at 100 deg.C for 12 hr to obtain dry core-shell type Fe2O3@ lignin; adding 1g of ammonium molybdate and 5g of thiourea into 150mL of deionized water, uniformly mixing, stirring at 60 ℃ for 6 hours, adding oxalic acid, adjusting the pH to 2, and taking dry core-shell Fe2O3@ lignin is immersed in the acidic molybdenum-sulfur mixed solution and undergoes hydrothermal reaction for 24 hours at 150 ℃ to obtain Fe2O3@ Lignin @ MoS2Composite material, Fe to be obtained2O3@ Lignin @ MoS2Placing the composite material in a microwave reactor, adjusting the power to 1000W under the nitrogen atmosphere of 400mL/min, reacting for 15min at 600 ℃, collecting the microwave pyrolysis product liquid oil, analyzing the components of the liquid oil, wherein the ratio of guaiacol to phenol in the liquid oil reaches 38.2% and 15.7%, respectively, which indicates that the product is mainly guaiacol and phenol.
Example 2
3g of glycine and 30g of Fe (NO)3)3·7H2Dissolving O in 500mL of a mixture of ethanol and water (volume ratio of ethanol to water is 1: 2), carrying out hydrothermal reaction at 180 ℃ for 12 hours, cooling to room temperature, washing with ethanol and distilled water for 4 times, and drying in a drying oven at 80 ℃ for 6 hours to obtain Fe2O3Nanospheres; 1g of solvent lignin was dissolved in 200mL of tetrahydrofuran, and then 0.5g of the above-obtained Fe was added2O3The nanospheres are placed in a dialysis bag with the molecular weight cutoff of 14000 after being fully stirred for 3 hours, the dialysis bag is placed in deionized water, the stirring is slowly carried out in a fume hood, the dialysis is carried out for 36 hours, and the core-shell Fe is obtained2O3@ lignin was washed with absolute ethanol 6 times, dried at 80 ℃ for 12h to obtain dry core-shell type Fe2O3@ lignin; adding 1g of ammonium molybdate and 2g of thiourea into 80mL of deionized water, uniformly mixing, stirring at 50 ℃ for 6 hours, adding oxalic acid, adjusting the pH to 2, and taking dry core-shell Fe2O3@ lignin is immersed in the acid molybdenum-sulfur mixed solution and undergoes hydrothermal reaction for 24 hours at 180 ℃ to obtain Fe2O3@ Lignin @ MoS2Composite material, Fe to be obtained2O3@ Lignin @ MoS2Placing the composite material in a microwave reactor, adjusting the power to 800W under the nitrogen atmosphere of 500mL/min, reacting for 10min at 550 ℃, collecting the microwave pyrolysis product liquid oil, analyzing the components of the liquid oil, wherein the ratio of guaiacol to phenol in the liquid oil respectively reaches 31.4% and 17.3%, and the product is mainly guaiacol and phenol.
Example 3
3g of glycine and 24g of Fe (NO)3)3·7H2Dissolving O in 750mL of a mixture of ethanol and water (the volume ratio of ethanol to water is 1: 2), carrying out hydrothermal reaction at 200 ℃ for 12 hours, cooling to room temperature, washing with ethanol and distilled water for 5 times, and drying in a drying oven at 60 ℃ for 7 hours to obtain Fe2O3Nanospheres; 1g of kraft lignin was dissolved in 500mL of tetrahydrofuran, and then 1g of the Fe obtained above was added2O3The nanospheres are placed in a dialysis bag with the molecular weight cutoff of 10000 after being fully stirred for 3 hours, the dialysis bag is placed in deionized water, the stirring is slowly carried out in a fume hood, the dialysis is carried out for 48 hours, and the core-shell type Fe is obtained2O3Washing with absolute ethanol for 5 times, and drying at 90 deg.C for 12 hr to obtain dry core-shell type Fe2O3@ lignin; adding 1g of ammonium molybdate and 3g of thiourea into 100mL of deionized water, uniformly mixing, stirring at 40 ℃ for 6 hours, adding oxalic acid, adjusting the pH to 2, and taking dry core-shell Fe2O3@ lignin is immersed in the acidic molybdenum-sulfur mixed solution and undergoes hydrothermal reaction for 24 hours at 120 ℃ to obtain Fe2O3@ Lignin @ MoS2Composite material, Fe to be obtained2O3@ Lignin @ MoS2Placing the composite material in a microwave reactor, adjusting the power to 900W under the atmosphere of 600mL/min nitrogen, reacting for 13min at 500 ℃, collecting the microwave pyrolysis product liquid oil, analyzing the components of the liquid oil, wherein the ratio of guaiacol to phenol in the liquid oil reaches 39.4% and 16.7%, respectively, which indicates that the product is mainly guaiacol and phenol.
It will be appreciated by those skilled in the art that the invention may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The embodiments disclosed above are therefore to be considered in all respects as illustrative and not restrictive. All changes which come within the scope of or equivalence to the invention are intended to be embraced therein.
Claims (10)
1. A method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin is characterized by comprising the following steps:
the method comprises the following steps: mixing glycine and Fe (NO)3)3·7H2Dissolving O in a mixed solution of ethanol and water, carrying out hydrothermal reaction, cooling to room temperature after the reaction is finished, washing with ethanol and distilled water for a plurality of times, and drying to obtain Fe2O3Nanospheres;
step two: dissolving lignin in tetrahydrofuran, and adding Fe obtained in the first step2O3The nanospheres are fully and uniformly stirred;
step three: putting the solution obtained in the step two into a dialysis bag with the cut-off molecular weight of 8000-14000, putting the dialysis bag into deionized water, slowly stirring and dialyzing for 24-48 hours in a fume hood to obtain core-shell Fe2O3@ lignin, washing with anhydrous ethanol several times, and oven drying to obtain dry core-shell type Fe2O3@ lignin;
step four: adding ammonium molybdate and thiourea into deionized water, uniformly mixing, wherein the mass ratio of ammonium molybdate to thiourea is 1: 2-1: 5, the mass ratio of ammonium molybdate to deionized water is 1: 80-1: 150, stirring for 6 hours at 40-60 ℃, adding oxalic acid, and adjusting the pH value to 2 to obtain an acidic molybdenum-sulfur mixed solution;
step five: mixing dried core-shell Fe2O3Soaking @ lignin in the mixed solution of molybdenum and sulfur, and performing hydrothermal reaction to obtain Fe2O3@ Lignin @ MoS2A composite material;
step six: mixing Fe2O3@ Lignin @ MoS2And carrying out microwave-assisted depolymerization reaction on the composite material in a nitrogen atmosphere, and collecting a liquid product to obtain liquid oil.
2. The method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin according to claim 1, wherein glycine and Fe (NO) are added in the first step3)3·7H2The mass ratio of O is 1: 5-1: 10, and the concentration of glycine in the mixed solution of ethanol and water is 3-6 g/L.
3. The method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin according to claim 2, wherein the volume ratio of ethanol to water in the mixed solution of ethanol and water is 1: 2.
4. The method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin according to claim 1, wherein in the second step, after the lignin is dissolved in tetrahydrofuran, the concentration of the obtained solution is 1-5 mg mL-1。
5. The method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin according to claim 1, wherein Fe is used in step two2O3The mass ratio of the nanospheres to the lignin is 1: (0.5-2).
6. The method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin according to claim 1, wherein said lignin in step two is one of alkali lignin, kraft lignin and solvent lignin.
7. The method for preparing guaiacol and phenol through microwave-assisted depolymerization of lignin according to claim 1, wherein the drying temperature in the third step is 80-100 ℃ and the drying time is 12 hours.
8. The method for preparing guaiacol and phenol by microwave-assisted depolymerization of lignin according to claim 1, wherein the temperature of the hydrothermal reaction in the fifth step is 120 ℃ to 180 ℃ for 24 hours.
9. The method for preparing guaiacol and phenol through microwave-assisted depolymerization of lignin according to claim 1, wherein in the sixth step, the flow rate of nitrogen is 400-600 mL/min.
10. The method for preparing guaiacol and phenol through microwave-assisted depolymerization of lignin according to claim 1, wherein in the sixth step, the microwave-assisted depolymerization reaction is performed at a power of 800-1000W, a temperature of 500-600 ℃ and a time of 10-15 min.
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