CN105669337A - Method for converting lignin and model compound thereof - Google Patents
Method for converting lignin and model compound thereof Download PDFInfo
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- CN105669337A CN105669337A CN201410667670.9A CN201410667670A CN105669337A CN 105669337 A CN105669337 A CN 105669337A CN 201410667670 A CN201410667670 A CN 201410667670A CN 105669337 A CN105669337 A CN 105669337A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
The invention relates to a method for converting lignin and a model compound thereof. The method comprises the steps of dispersing the lignin model compound and the lignin into an organic solvent, then, adding a prepared oxygen-doped molybdenum disulfide catalyst (O-MoS2) into the dispersion solution, and carrying out a reaction for 2 to 24 hours under the conditions that the temperature is 160 DEG C to 260 DEG C, the pressure is 1.0MPa to 5.0MPa and hydrogen gas serves as a reducing agent, so as to efficiently convert the lignin model compound and the lignin into corresponding phenols and fine chemicals thereof with aromatic structures.
Description
Technical field
The invention belongs to energy technology field, be specifically related to a kind of lignin and the method for model compound conversion thereof.
Background technology
The energy and chemicals are important motivity and the guarantees of current social development. Oil, natural gas, the fossil energy such as coal is refined through the processing of chemical industry, provides substantial amounts of fuel and chemicals for human society. But being as the continuous consumption of all kinds of fossil energy, the sharply decline of reserves, the supply steady in a long-term of fossil energy receives serious challenge, and the novel of fuel and chemicals is prepared in searching, and reborn type energy becomes the inexorable trend of social development. In numerous candidate's green energy resources, reproducible biomass energy and wide material sources, nature rich reserves (biomass that nature is synthesized by photosynthesis every year are up to 170,000,000,000 tons) enjoys the concern of people.
In plant, lignin, cellulose, hemicellulose association exist, and three is also three key components of plant biomass. Wherein lignin refers to the material that the relative molecular mass being difficult to be hydrolyzed under acid effect is higher, is primarily present in the cell of lignified plant, fortification of plants tissue. Its chemical constitution is the complex compound of phenylpropyl alcohol alkanes construction unit composition, total three basic structures (non-condensed structure), i.e. guaiacyl structure, Syringa oblata Lindl. based structures and p-hydroxyphenyl structure. Containing substantial amounts of functionalization aromatic ring structure in lignin, it is the potential energy product with significant application value of a class, but its structure is complicated three-dimensional heavy polymer, the chemical bond of attachment structure unit is the C-O-C ehter bond that chemical stability is very strong, and C-C key etc., this also makes the exploitation of such energy be faced with important challenge. Although being faced with very big challenge, but in lignin conversion, also achieve a lot of progress.
Koyama etc. have studied the compound (Bioresour.Technol., 1993,44 (3): 209-215.) that a lot of Fe base Mo base hydrogenation catalyst contains dissimilar ehter bond type at hydrogenation. Song Qi etc. have studied C-O-C key hydrocracking performance (ChineseJCatal2013 in the catalyst based upper lignin model compound phenyl ethyl phenyl ether of Ni, 34 (4), 651-658.) and effect (Energy&EnvironmentalScience2013 in true birch lignin hydrocracking, 6 (3), 994-1007.). Bergman etc. are with RuH2(CO)(PPh3)3For catalyst, have studied its application in C-O-C key hydrocracking processes (J.Am.Chem.Soc., 2010,132 (36): 15554-1255.) in phenoxy group-1-phenethanol and derivant thereof.Also a lot of Heterogeneous Noble Metals Catalysts is had from the document in the past delivered, but it is because its hyperactivity, easily it is hydrogenated with aromatic rings, and catalyst in use easily sinters, and air-sensitive is easily aoxidized and loses activity by such catalyst so that the application of such material is limited by very large. In this external non-precious metal catalyst, also have a lot of conventional catalyst with base of molybdenum to be applied in catalytic hydrogenation lignin process, but common activity is not high enough, and need to carry out under higher reaction condition. Therefore a kind of base metal is developed, to air-stable and to have the catalyst of greater activity be a job highly significant.
The invention reside in provide a kind of utilizes cheap easy preparation and the material molybdenum sulfide for air-stable to crack lignin and model compound thereof for catalyst efficient catalytic hydrogen reducing and be converted into phenolic compound and the method for some other fine chemicals with aromatic structure.
Summary of the invention
The present invention relates to a kind of lignin and the method for model compound conversion thereof, lignin model compound and lignin are scattered in organic solvent, the oxygen being subsequently adding preparation mixes molybdenum sulfide catalyst, at 160～260 DEG C, react 2～24h high efficiency conversion lignin model compound when 1.0～5.0MPa hydrogen is reducing agent and organic soluble lignin is corresponding aldehydes matter and the fine chemicals with aromatic structure thereof.
Molybdenum sulfide is the hydrogenation catalyst that a class is important, it is layer structure, and have been reported that the interlamellar spacing of such material of display and the marginal portion of layer serve the effect of key, modified two catalytic effects that can improve catalyst significantly to such character for catalytic action before. We have found that the molybdenum disulfide catalyst that the method only introduced according to this patent prepares just has catalytic effect well by contrasting, the material molybdenum sulfide directly bought does not have activity or catalytic effect very poor. Preparation method about molybdenum sulfide catalyst: with ammonium molybdate, sodium molybdate is predecessor, thiourea, and sodium sulfide is sulfur source, according to n(Mo):n(S)The ratio of=1:3～1:30 is scattered in aqueous solution, and hydrothermal treatment consists 6～72h at 160～240 DEG C, filtration washing obtains catalyst. Wherein better with ammonium molybdate for predecessor effect relatively sodium molybdate effect, thiourea low price and be easily controlled decomposition in sulfur source, more particularly suitable in preparation material molybdenum sulfide process, the synthesis of catalyst is optimized: according to n(Mo):n(S)The ratio of=1:6～1:30 feeds intake, and at 160～220 DEG C, hydrothermal treatment consists 12～48h is comparatively suitable.
Reaction condition about molybdenum sulfide catalysis formic acid and formates can carry out according to following condition: the concentration of substrate, it is 0.001～1mol/L for model compound, it is 0.005～0.1g/mL for lignin, 5～50w% of the consumption substrate quality of catalyst, reaction temperature is 160 DEG C～280 DEG C, the initial pressure of hydrogen is 0.1～8.0MPa, and the response time is 1h～72h. After optimal conditions: the concentration of substrate, it is 0.001～0.05mol/L for model compound, it is 0.005～0.03g/mL for lignin, 5～30w% of the consumption substrate quality of catalyst, reaction temperature is 160 DEG C～260 DEG C, the initial pressure of hydrogen is 1.0～5.0MPa, and the response time is 2h～12h.
Advantageous Effects
The invention reside in provide a kind of utilizes cheap easy preparation and the material molybdenum sulfide for air-stable to crack lignin and model compound thereof for catalyst efficient catalytic hydrogen reducing and be converted into phenolic compound and the method for some other fine chemicals with aromatic structure.
Detailed description of the invention
In order to the present invention is further elaborated, several be embodied as case is given below, but the invention is not restricted to these embodiments.
1. oxygen mixes molybdenum disulfide catalyst (O-MoS2) preparation of catalyst
O-MoS2It is undertaken synthesizing by the mode of hydro-thermal. By ammonium molybdate and thiourea according to n(Mo):n(S)=1:3～30 ratio joins in the stainless steel autoclave of a 150mL tetrafluoro liner, 90mL deionized water is added when stirring, formed after solution airtight, after stainless steel autoclave is put into the baking oven standing 12～48h of 160～250 DEG C, take out reactor, naturally cool to room temperature, the black solid deionized water obtained and absolute ethanol washing. The sample number into spectrum obtained is O-MoS2(x-y-zh), wherein x represents the mol ratio of thiourea molecule and molybdenum atom, the temperature that y representative processes, the time that z representative processes.
2. the conversion of model compound
Model compound and numbering thereof:
Comparative catalyst MoO in embodiment2、MoO3、MoS2、MoS3All it is commercially available from medication suppliers.
Embodiment 1
2mL methanol, 0.2mmol lignin model compound A1, the catalyst MoS of purchase it is sequentially added in the reactor with magnetic agitation250mg, is filled with hydrogen 3MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Lignin model compound conversion ratio is 0.5%.
Embodiment 2
2mL methanol, 0.2mmol lignin model compound A1, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-180-24h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 10.5%.
Embodiment 3
2mL methanol, 0.2mmol lignin model compound B1, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-180-24h) 50mg is filled with hydrogen 1MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 20.5%.
Embodiment 4
2mL methanol, 0.2mmol lignin model compound B1, catalyst MoS it is sequentially added in the reactor with magnetic agitation250mg is filled with hydrogen 1MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 7.5%.
Embodiment 5
2mL methanol, 0.2mmol lignin model compound C1, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-180-24h) 50mg is filled with hydrogen 1MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 67.5%.
Embodiment 6
2mL methanol, 0.2mmol lignin model compound C1, catalyst MoS it is sequentially added in the reactor with magnetic agitation250mg is filled with hydrogen 1MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 20.5%.
Embodiment 7
2mL methanol, 0.2mmol lignin model compound A3, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(20-180-24h) 50mg is filled with hydrogen 2MPa, airtight. Reacting 10h, centrifugation at 200 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 7.6%.
Embodiment 8
2mL methanol, 0.2mmol lignin model compound A2, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-220-24h) 50mg is filled with hydrogen 3MPa, airtight.Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 6.2%.
Embodiment 9
2mL methanol, 0.2mmol lignin model compound A1, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-180-24h) 50mg is filled with hydrogen 2MPa, airtight. Reacting 10h, centrifugation at 200 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 9.5%.
Embodiment 10
2mL methanol, 0.2mmol lignin model compound B2, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(20-200-24h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 12h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 30.5%.
Embodiment 11
2mL methanol, 0.2mmol lignin model compound B3, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(25-200-48h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 12h, centrifugation at 200 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 16.7%.
Embodiment 12
2mL methanol, 0.2mmol lignin model compound B2, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(25-180-24h) 50mg is filled with hydrogen 2MPa, airtight. Reacting 12h, centrifugation at 200 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 15.7%.
Embodiment 13
2mL methanol, 0.2mmol lignin model compound B3, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-190-24h) 50mg is filled with hydrogen 4MPa, airtight. Reacting 12h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 25.6%.
Embodiment 14
2mL methanol, 0.2mmol lignin model compound C2, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-210-24h) 50mg is filled with hydrogen 2.5MPa, airtight. Reacting 12h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 45.5%.
Embodiment 15
2mL methanol, 0.2mmol lignin model compound C3, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-230-12h) 50mg is filled with hydrogen 2MPa, airtight. Reacting 6h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 50.5%.
Embodiment 16
2mL methanol, 0.2mmol lignin model compound C2, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-180-48h) 50mg is filled with hydrogen 2MPa, airtight. Reacting 12h, centrifugation at 200 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 64.5%.
Embodiment 17
2mL methanol, 0.2mmol lignin model compound C3, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(20-180-24h) 50mg is filled with hydrogen 1MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis.Model compound conversion ratio is 50.5%.
Embodiment 18
2mL methanol, 0.2mmol lignin model compound C1, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-180-24h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 8h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 83.5%.
Embodiment 19
2mL methanol, 0.2mmol lignin model compound C2, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-200-24h) 50mg is filled with hydrogen 2MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 73.8%.
Embodiment 20
2mL methanol, 0.2mmol lignin model compound C3, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(25-200-24h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 12h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. Model compound conversion ratio is 79.5%.
3. the conversion of lignin
Lignin as substrate: ground wood quality, alkali lignin, ionic liquid separating lignin, enzymolysis xylogen, organic soluble Acell lignin, Isosorbide-5-Nitrae-dioxane lignin and wood powder.
Embodiment 1
5mL methanol, 100mg organic soluble Acell lignin, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-200-24h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 10h, centrifugation at 230 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 36mg after using internal standard substance conversion.
Embodiment 2
5mL methanol, 100mg1,4-dioxane lignin lignin, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-180-24h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 10h, centrifugation at 250 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 22mg after using internal standard substance conversion.
Embodiment 3
In the reactor with magnetic agitation, it is sequentially added into 5mL methanol, 100mg organic soluble Acell lignin, catalyst-free, is filled with hydrogen 3MPa, airtight. Reacting 10h, centrifugation at 180 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 8mg after using internal standard substance conversion.
Embodiment 4
5mL methanol, 100mg alkali lignin, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-220-24h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 12h, centrifugation at 220 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 16mg after using internal standard substance conversion.
Embodiment 5
5mL methanol, 100mg ionic liquid separating lignin lignin, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-180-24h) 50mg is filled with hydrogen 4MPa, airtight. Reacting 12h, centrifugation at 240 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 16mg after using internal standard substance conversion.
Embodiment 6
5mL methanol, 100mg enzymolysis xylogen, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-200-24h) 50mg is filled with hydrogen 3MPa, airtight. Reacting 10h, centrifugation at 250 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 5.9mg after using internal standard substance conversion.
Embodiment 7
5mL methanol, 100mg ground wood quality, catalyst O-MoS it is sequentially added in the reactor with magnetic agitation2(30-220-12h) 50mg is filled with hydrogen 4MPa, airtight. Reacting 10h, centrifugation at 240 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 8mg after using internal standard substance conversion.
Embodiment 8
Being sequentially added into 5mL methanol in the reactor with magnetic agitation, 100mg removes fat birch lignin, catalyst O-MoS2(25-200-24h) 50mg is filled with hydrogen 5MPa, airtight. Reacting 10h, centrifugation at 220 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 17mg after using internal standard substance conversion.
Embodiment 9
Being sequentially added into 5mL methanol in the reactor with magnetic agitation, 100mg removes fat birch lignin, catalyst O-MoS2(30-200-24h) 50mg is filled with hydrogen 5MPa, airtight. Reacting 8h, centrifugation at 250 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 15mg after using internal standard substance conversion.
Embodiment 10
Being sequentially added into 5mL methanol in the reactor with magnetic agitation, 100mg removes fat spruce wood lignin, catalyst O-MoS2(30-180-24h) 50mg is filled with hydrogen 5MPa, airtight. Reacting 10h, centrifugation at 230 DEG C, the sample of gained uses GC-MS and GC qualitative and quantitative analysis. The phenolic compound that model compound is converted into is 10mg after using internal standard substance conversion.
Claims (9)
1. the method that a lignin and model compound thereof convert, it is characterised in that: being scattered in organic solvent by one or two or more kinds in lignin model compound or lignin, the oxygen being subsequently adding preparation mixes molybdenum disulfide catalyst (O-MoS2), at 160～260 DEG C, hydrogen is reducing agent, when initial pressure is 1.0～5.0MPa, reacts 2～24h, converts lignin model compound and lignin is corresponding aldehydes matter and the fine chemicals with aromatic structure thereof.
2. in accordance with the method for claim 1, it is characterised in that:
(1) lignin model compound is:
Wherein, R represents different substituent groups, R=-H ,-CH3,-CH2CH3,-CH (OH) CH3,-OH ,-CH2OH,-OCH3,-CH (OH) CH2One or two or more kinds in OH or-CHO, x=1～5, x represents the number of substituent R, as x > 1 time, the substituent group that R can be identical can also be different substituent group;
(2) lignin is one or two or more kinds in ground wood quality, alkali lignin, ionic liquid separating lignin, enzymolysis xylogen, cuprammonium lignin, hydrochloric acid lignin, ligninsulfonate, organic soluble Acell lignin, 1,4-dioxane lignin.
3. in accordance with the method for claim 2, it is characterised in that:
Lignin is preferably one or more in ground wood quality, alkali lignin, ionic liquid separating lignin, enzymolysis xylogen, organic soluble Acell lignin, 1,4-dioxane lignin.
4. in accordance with the method for claim 1, it is characterised in that:
Oxygen mixes molybdenum disulfide catalyst (O-MoS2) preparation method: with ammonium molybdate or sodium molybdate for predecessor, thiourea or sodium sulfide are sulfur source, according to n(Mo):n(S)The ratio of=1:3～30 is scattered in deionized water, and hydrothermal treatment consists 6～72h at 160～240 DEG C, filtration washing obtains oxygen and mixes material molybdenum sulfide.
5. in accordance with the method for claim 4, it is characterised in that:
The preferred ammonium molybdate of predecessor, the preferred thiourea in sulfur source, according to n(Mo):n(S)The ratio of=1:6～30 is scattered in aqueous solution, hydrothermal treatment consists 12～48h at 160～220 DEG C, and filtration washing obtains filtration washing and obtains oxygen and mix material molybdenum sulfide.
6. in accordance with the method for claim 1, it is characterised in that:
When substrate is lignin model compound, lignin model compound molar concentration is 0.001～1mol/L;
When substrate is lignin, lignin quality concentration is 0.005～0.1g/mL, and the consumption of catalyst is 5～50w% of substrate quality.
7. in accordance with the method for claim 6, it is characterised in that:
When substrate is lignin model compound, the preferred molar concentration of lignin model compound is 0.001～0.05mol/L;
When substrate is lignin, lignin preferred mass concentration is 0.005～0.03g/mL, and the consumption of catalyst is preferably 5～30w% of substrate quality.
8. in accordance with the method for claim 1, it is characterised in that: preferable reaction temperature is 160 DEG C～260 DEG C, and the preferred initial pressure of hydrogen is 1.0～5.0MPa, it is preferable that the response time is 2h～24h.
9. in accordance with the method for claim 1, it is characterised in that: organic solvent is one or more in methanol, acetone, Isosorbide-5-Nitrae-dioxane, ethylene glycol.
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| CN115724465A (en) * | 2022-11-29 | 2023-03-03 | 陕西科技大学 | High-oxygen-content doped molybdenum disulfide material and preparation method thereof |
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Cited By (9)
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| CN108947783A (en) * | 2017-05-18 | 2018-12-07 | 中国科学院大连化学物理研究所 | A kind of method that molybdenum Catalytic lignin is degraded to fragrant monomer |
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| CN115160382A (en) * | 2022-07-28 | 2022-10-11 | 中国科学技术大学 | Method for catalytic depolymerization of lignin |
| CN115160382B (en) * | 2022-07-28 | 2024-03-26 | 中国科学技术大学 | Method for catalytic depolymerization of lignin |
| CN115724465A (en) * | 2022-11-29 | 2023-03-03 | 陕西科技大学 | High-oxygen-content doped molybdenum disulfide material and preparation method thereof |
| CN115724465B (en) * | 2022-11-29 | 2024-04-12 | 陕西科技大学 | High-oxygen-content doped molybdenum disulfide material and preparation method thereof |
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