CN117983277B - Preparation method and application of catalyst for oxidative dehydrogenation of hydroxyl-containing compound - Google Patents

Preparation method and application of catalyst for oxidative dehydrogenation of hydroxyl-containing compound Download PDF

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CN117983277B
CN117983277B CN202410154866.1A CN202410154866A CN117983277B CN 117983277 B CN117983277 B CN 117983277B CN 202410154866 A CN202410154866 A CN 202410154866A CN 117983277 B CN117983277 B CN 117983277B
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vanadium
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hydroxyl
based catalyst
catalyst
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CN117983277A (en
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刘宗辉
徐京
周亚利
薛冰
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Changzhou University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/24—Nitrogen compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48—Furfural

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Abstract

The invention relates to a preparation method and application of a catalyst for oxidative dehydrogenation of hydroxyl-containing compounds. Various nitrogen-carbon materials are used as nitrogen sources and carbon sources, different vanadium salts are used as precursors, and a series of vanadium-doped nitrogen-carbon catalysts (V-N-C) are prepared by a mechanical mixing method and a high-temperature roasting method. Wherein the nitrogen-carbon material comprises chitosan, chitin, urea and other substances, and the vanadium salt is organic salt or inorganic salt. By adjusting factors such as the types of the nitrogen-carbon material and the vanadium salt precursor, the roasting temperature and the like, the accurate regulation and control of the oxidation-reduction property of the surface of the catalyst are realized. The vanadium-based catalyst prepared by the method has simple preparation process and better catalytic performance on hydroxyl-containing compounds (such as lactate), and takes ethyl lactate as an example, the conversion rate of the ethyl lactate can reach 99% and the selectivity of the ethyl pyruvate can reach more than 98% at 130 ℃ reaction.

Description

Preparation method and application of catalyst for oxidative dehydrogenation of hydroxyl-containing compound
Technical Field
The invention belongs to the technical field of chemical catalytic materials, and particularly relates to preparation of a vanadium-based catalyst and application of the vanadium-based catalyst in liquid-phase catalytic lactate oxidation reaction.
Background
Pyruvic acid (ester) is an important organic intermediate and plays a role in bioenergy metabolism and organic synthesis. At present, the production method of pyruvic acid (ester) mainly comprises a tartaric acid dehydration and dehydroxylation method, a lactic acid (ester) catalytic oxidation method, a hydroxyacetone method, an electrochemical method and a biotechnology method. The technology for producing pyruvic acid in China still uses a lagging tartaric acid method, and the process has simple flow, but low product yield and serious pollution, thereby limiting the large-scale production and application of pyruvic acid. The method for preparing the high-purity pyruvic acid ester by using the lactic acid ester as the raw material through selective oxidation has the characteristics of excellent product quality, environmental protection, high production elasticity and the like. The core of this technical route is how to efficiently achieve the directional conversion of lactate to pyruvate.
With the rise and application of a large amount of carbon materials in recent years, non-metal carbon materials are widely applied to catalysis, and compared with some metal catalysts used in early stages, after adding carbon nitrogen element into the catalyst, the catalyst can generally show very excellent catalytic performance in many heterogeneous catalytic reactions due to various metal-carrier interactions, and has very high potential application value. For example, CN201910642151.X, a graphite phase C 3N4 -loaded V 2O5 catalyst is synthesized by taking urea as a precursor, and is used in the reaction of preparing ethyl pyruvate by oxidizing ethyl lactate, the reaction is carried out for 4 hours at 130 ℃, the conversion rate of the ethyl lactate is 96.2%, and the yield of the ethyl pyruvate is 82.3%.
According to the invention, the nitrogen-carbon material and the vanadium salt are used as precursors, and a catalyst for efficiently catalyzing the conversion of lactate to prepare pyruvic acid ester is developed and prepared through simple mechanical mixing and high-temperature roasting processes. The reaction is carried out for 3 hours at 130 ℃, so that the yield of the pyruvic acid ester can reach more than 97 percent, and the method has universality for oxidative dehydrogenation of other hydroxyl-containing compounds.
Disclosure of Invention
The invention provides a method for synthesizing a hydroxyl-containing compound (such as ethyl lactate) by high-efficiency catalytic oxidative dehydrogenation of a vanadium-based catalyst. The interaction of the active site vanadium and the carrier in the catalyst improves the oxidability of the catalyst, thereby improving the performance of the catalyst.
In order to solve the technical problems, the invention adopts the following technical scheme:
a preparation method of a vanadium-based catalyst is carried out according to the following steps:
(1) Weighing nitrogen-carbon precursor and vanadium the salt is put into a mortar for grinding uniformly. The mass ratio of the nitrogen-carbon precursor to the vanadium salt is 1-2: 1 to 4.
(2) The solid powder obtained by grinding is put into a tube furnace, heated from room temperature to a designated roasting temperature of 500-700 ℃ at 5.0 ℃/min and maintained for 3 hours, and the obtained black powder is marked as V-N-C-X (X is a carrier prepared by different precursors).
As a further limitation of the present invention, the vanadium salts of the present invention are organic vanadium salts such as VO (acac) 2、VOC2O4·5H2 O; or inorganic vanadium salts such as VOSO 4、NH4VO3、VCl3. Preferably, the vanadium salt is VOSO 4、VO(acac)2.
As the limitation of the invention, the nitrogen-carbon material is one of chitosan, chitin, urea, dicyandiamide, melamine and urotropine. Preferably, the nitrogen-carbon material is chitosan or chitin.
As a limitation of the present invention, the firing temperature of the present invention is preferably: 600 ℃.
The application of the prepared vanadium-based catalyst in the catalytic oxidation reaction of hydroxyl-containing compounds; the hydroxyl compound is one of methyl lactate, ethyl lactate, butyl lactate, benzyl alcohol, furfuryl alcohol, cinnamyl alcohol and n-propanol.
(1) Adding a hydroxyl compound, a vanadium-based catalyst and an organic solvent into an intermittent high-pressure reaction kettle, replacing gas with oxygen, and then filling oxygen with initial pressure of 0.2-1.8 MPa;
(2) Setting the reaction temperature to be 100-130 ℃ and the reaction time to be 1-5 h under the stirring state, rapidly cooling the reaction kettle to room temperature after the reaction is finished, analyzing the product by using gas chromatography, and collecting the product.
As a further limitation of the present invention, the mass molar ratio of the catalyst to the hydroxyl group-containing compound described in the present invention is 30 to 50mg:2mmol.
As a further definition of the invention, the molar volume ratio of the reactant to the solvent in step (1) of the invention is 2mmol:15mL.
As a further limitation of the present invention, the solvent in step (1) of the present invention is one of acetonitrile, acetone, diethyl succinate and DMF;
As a further limitation of the present invention, the reaction temperature in step (1) of the present invention is 130℃and the reaction time is 3 hours.
As a further definition of the invention, applicable applications are: methyl lactate is oxidized to obtain methyl pyruvate; oxidizing ethyl lactate to obtain ethyl pyruvate; butyl lactate is oxidized to obtain butyl pyruvate; the benzyl alcohol is oxidized to obtain benzaldehyde; furfuryl alcohol is oxidized to obtain furfural; carrying out an oxidation reaction on cinnamyl alcohol to obtain cinnamyl aldehyde; the oxidation of n-propanol yields n-propanal.
Compared with the traditional catalyst, the preparation method of the vanadium-based catalyst provided by the invention has the following advantages:
under mild reaction conditions, the vanadium-based catalyst prepared by the method has better catalytic performance on oxidative dehydrogenation of hydroxyl-containing compounds, for example, the conversion rate of 97.3% ethyl lactate can be realized by reacting ethyl lactate at 130 ℃ for 3 hours, the selectivity to ethyl pyruvate can reach more than 98%, and meanwhile, the method also has the advantages of simple catalyst preparation, low-cost and easily obtained raw materials, high atom utilization rate, environmental friendliness, wide substrate universality and the like.
Drawings
FIG. 1 is an XPS spectrum of a vanadium-based catalyst prepared with chitin and chitosan as nitrogen-carbon precursor materials;
From the figure, it can be seen that the catalyst mainly contains several elements of V, N, C and O, which indicates that V is successfully introduced into the nitrogen-carbon material.
Detailed Description
The invention will be further illustrated with reference to the following examples, but it should be understood that these examples are for illustrative purposes only and should not be construed as limiting the practice of the invention. The materials used in the examples below were all conventional commercial products.
According to the invention, the V-N-C-X catalyst is synthesized by adopting a mechanical grinding and high-temperature roasting method, and different V-N-C-X catalysts can be obtained by adjusting parameters such as roasting temperature, types of vanadium precursors and carriers in the synthesis process.
Examples 1 to 5
The influence of different vanadium precursor types on ethyl lactate conversion rate and ethyl pyruvate selectivity is as follows:
Preparation of V-N-C_chitosan catalyst:
The preparation scheme of the V-N-C-chitosan catalyst comprises the following steps: 1.5g of chitosan and 3g of vanadium salt precursor are weighed and put into a mortar for uniform grinding. The solid powder obtained was placed in a tube furnace and heated from room temperature to 600℃at 5.0℃per minute and maintained for 3 hours, and the black powder obtained was designated as V-N-C-chitosan.
2Mmol ethyl lactate, 50mg V-N-C chitosan catalyst, 0.2MPa O 2 and 15mL acetonitrile are placed in a 50mL intermittent high-pressure reaction kettle, a reaction device is assembled, the temperature is raised to 130 ℃, the stirring reaction is carried out for 3 hours, and the product analysis is carried out by adopting gas chromatography after the reaction is finished.
TABLE 1 influence of vanadium salt precursor species on ethyl lactate conversion and ethyl pyruvate selectivity
Examples Vanadium precursor Conversion (%) Selectivity (%)
1 VO(acac)2 91.5 97.5
2 VOC2O4·5H2O 85.6 96.6
3 VOSO4 95.8 98.1
4 NH4VO3 87.6 97.5
5 VCl3 82.3 95.0
From table 1, it can be seen that the catalysts synthesized by using different vanadium precursors have good catalytic effects on preparing ethyl pyruvate by catalyzing and oxidizing ethyl lactate, and when VOSO 4 is selected as the vanadium-based catalyst precursor, the conversion rate of ethyl lactate and the selectivity of ethyl pyruvate are the highest.
Examples 6 to 11
The influence of different nitrogen-carbon precursor types on ethyl lactate conversion rate and ethyl pyruvate selectivity is as follows:
The catalysts of examples 6-11 were prepared as in example 3 except that chitosan was changed to other nitrogen carbon precursors (chitin, dicyandiamide, melamine, urea, urotropine).
2Mmol of ethyl lactate, 50mg of catalyst, 0.2MPa of O 2 and 15mL of acetonitrile are placed in a 50mL batch high-pressure reaction kettle, a reaction device is assembled, the temperature is raised to 130 ℃, the reaction is stirred for 0.5h, and the product analysis is quantitatively analyzed by adopting gas chromatography after the reaction is finished.
TABLE 2 influence of nitrogen-carbon precursor species on ethyl lactate conversion and ethyl pyruvate selectivity
Examples Nitrogen carbon precursor Conversion (%) Selectivity (%)
6 V-N-C-chitosan 76.2 99.3
7 V-N-C-chitin 75.4 99.0
8 VO x/NC_dicyandiamide 39.5 99.4
9 VO x/NC_melamine 74.0 99.3
10 VO x/NC_urea 33.6 99.1
11 VO x/NC_urotropine 70 98.9
Table 2 shows that the catalyst synthesized by taking different nitrogen-carbon materials as precursors can better catalyze and oxidize ethyl lactate to prepare ethyl pyruvate.
The catalysts used in the following examples (12-18) were all V-N-C-chitin, and the specific preparation process of V-N-C-chitin was the same as in example 7.
Examples 12 to 15
The influence of different reaction temperatures on ethyl lactate conversion rate and ethyl pyruvate selectivity is as follows:
2mmol ethyl lactate, 50mg V-N-C-chitin catalyst, 0.2MPa O 2 and 15mL acetonitrile are placed in a 50mL intermittent high-pressure reaction kettle, a reaction device is arranged, the temperature is raised to 90-130 ℃, the stirring reaction is carried out for 3h, and the product analysis is carried out by adopting gas chromatography after the reaction is finished.
TABLE 3 influence of reaction temperature on ethyl lactate conversion and ethyl pyruvate selectivity
Examples Reaction temperature (. Degree. C.) Conversion (%) Selectivity (%)
12 90 31.9 99.3
13 110 85.8 99.4
14 120 98.4 99.1
15 130 99.8 97.9
Examples 16 to 18
The influence of different reaction times on ethyl lactate conversion and ethyl pyruvate selectivity was studied, and the specific steps were as follows:
2mmol ethyl lactate, 50mg V-N-C-chitin catalyst, 0.2MPa O 2 and 15mL acetonitrile are placed in a 50mL intermittent high-pressure reaction kettle, a reaction device is assembled, the temperature is raised to 120 ℃, and after 0.5-3 h of reaction, quantitative analysis is carried out by adopting gas chromatography.
TABLE 4 influence of reaction time on ethyl lactate conversion and ethyl pyruvate selectivity
Examples Reaction time (h) Conversion (%) Selectivity (%)
16 0.5 66.8 99.3
17 2 97.3 97.8
14 3 98.4 99.1
18 5 99.2 98.9
Examples 19 to 20
The catalyst preparation was the same as in example 7 except that the calcination temperatures were different, and the effect of the catalyst prepared at the different calcination temperatures on ethyl lactate conversion and ethyl pyruvate selectivity was studied, and the specific steps were as follows:
2mmol ethyl lactate, 50mg V-N-C-chitin catalyst, 0.2MPa O 2, 15ml acetonitrile are placed in a 50ml intermittent high-pressure reaction kettle, a reaction device is assembled, the temperature is raised to 130 ℃, the stirring reaction is carried out for 0.5h, and the product analysis is carried out by adopting gas chromatography after the reaction is finished.
TABLE 5 influence of calcination temperature on ethyl lactate conversion and ethyl pyruvate selectivity
Examples Firing temperature (. Degree. C.) Conversion (%) Selectivity (%)
19 500 66.1 99.3
7 600 75.4 99.0
20 700 73.2 97.8
Examples 21 to 22
Preparation of V-N-C-chitin catalyst the influence of different reaction atmospheres on ethyl lactate conversion and ethyl pyruvate selectivity was investigated as in example 7, the specific steps were as follows:
2mmol ethyl lactate, 50mg V-N-C-chitin catalyst, 0.2MPa gas and 15mL acetonitrile are placed in a 50mL intermittent high-pressure reaction kettle, a reaction device is arranged, the temperature is raised to 120 ℃, the reaction is stirred for 2h, and the product analysis is quantitatively analyzed by adopting gas chromatography after the reaction is finished.
TABLE 6 influence of reaction atmosphere on ethyl lactate conversion and ethyl pyruvate selectivity
Examples Atmosphere of gas Conversion (%) Selectivity (%)
21 Air 57.3 99.2
22 O2 97.3 97.8
Examples 23 to 24
Preparation of V-N-C-chitin catalyst the effect of different catalyst amounts on ethyl lactate conversion and ethyl pyruvate selectivity was investigated as in example 7, the specific steps were as follows:
2mmol ethyl lactate, 30-50 mg V-N-C-chitin catalyst, 0.2MPaO 2 mL acetonitrile, a 50mL intermittent high-pressure reaction kettle, a reaction device, a temperature rising device, a stirring reaction device, a reaction time of 2h, and a product analysis after the reaction is finished, a gas chromatography is adopted for quantitative analysis.
TABLE 7 influence of catalyst amount on ethyl lactate conversion and ethyl pyruvate selectivity
Examples Catalyst amount (mg) Conversion (%) Selectivity (%)
23 30 78.7 98.8
24 50 97.3 97.8
Examples 25 to 27
Preparation of V-N-C_chitin catalyst the influence of different solvents on ethyl lactate conversion and ethyl pyruvate selectivity was studied as in example 7, the specific steps were as follows:
2mmol ethyl lactate, 50mg V-N-C-chitin catalyst, 0.2MPaO 2 mL solvent, a 50mL intermittent high-pressure reaction kettle, a reaction device, heating to 120 ℃, stirring for 2h, and quantitatively analyzing the product by gas chromatography after the reaction.
TABLE 8 influence of solvent on ethyl lactate conversion and ethyl pyruvate selectivity
Examples Solvent(s) Conversion (%) Selectivity (%)
25 Acetone (acetone) 92.4 98.6
26 Succinic acid diethyl ester 98.5 98.7
27 DMF 96.7 99.1
Examples 28 to 33
Preparation of V-N-C-chitin catalyst the catalyst system was investigated for its general effect on different substrates as in example 7, comprising the following steps:
2mmol substrate, 50mg V-N-C-chitin catalyst, 0.2MPa O 2 and 15mL acetonitrile are placed in a 50mL intermittent high-pressure reaction kettle, a reaction device is assembled, the temperature is raised to 120 ℃, the stirring reaction is carried out for 2 hours, and the product analysis is carried out by adopting gas chromatography after the reaction is finished.
TABLE 9 Universal influence of catalyst systems on different substrates
Examples Substrate(s) Product(s) Conversion (%) Selectivity (%)
28 Lactic acid methyl ester Pyruvic acid methyl ester 98.7 98.2
17 Lactic acid ethyl ester Pyruvic acid ethyl ester 97.3 97.8
29 Butyl lactate Pyruvic acid butyl ester 87.4 88.7
30 Benzyl alcohol Benzaldehyde 95.8 97.8
31 Furfuryl alcohol Furfural 58.6 86.8
32 Cinnamic alcohol Cinnamic aldehyde 100 97.1
33 N-propanol N-propanal 89.1 89.5
Comparative example 1
V 2O5 is used as a catalyst, and the specific steps are as follows:
2mmol of ethyl lactate, 50mg of catalyst, 0.2MPaO 2 mL of acetonitrile and 15mL of acetonitrile are placed in a 50mL batch high-pressure reaction kettle, a reaction device is assembled, the temperature is raised to 130 ℃, the reaction is stirred for 0.5h, and the product analysis is quantitatively analyzed by adopting gas chromatography after the reaction is finished. In this example, the conversion of ethyl lactate was 11.0% and the selectivity of ethyl pyruvate was 96.5%.
Comparative example 2
V 2O3 is used as a catalyst, and the specific steps are as follows:
2mmol of ethyl lactate, 50mg of catalyst, 0.2MPaO 2 mL of acetonitrile and 15mL of acetonitrile are placed in a 50mL batch high-pressure reaction kettle, a reaction device is assembled, the temperature is raised to 130 ℃, the reaction is stirred for 0.5h, and the product analysis is quantitatively analyzed by adopting gas chromatography after the reaction is finished. In this example, the conversion of ethyl lactate was 72.3% and the selectivity of ethyl pyruvate was 99.1%.
As can be seen from tables 3 to 7, the reaction conditions such as the reaction temperature, time, firing temperature, reaction atmosphere, catalyst amount and the like have a large influence on the reaction, but the selectivity of ethyl pyruvate is over 95%. Table 9 shows that the catalyst also has better catalytic effect on other substrates (such as methyl lactate, ethyl lactate, butyl lactate, benzyl alcohol, furfuryl alcohol, cinnamyl alcohol, n-propanol and the like). The results of the examples and the comparative examples show that the catalyst synthesized by the method has better catalytic performance than pure vanadium oxide.
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.

Claims (5)

1. The application of a vanadium-based catalyst in the oxidative dehydrogenation of hydroxyl-containing compounds is characterized in that:
Adding a hydroxyl-containing compound, a vanadium-based catalyst and an organic solvent into a high-pressure reaction kettle, replacing gas with oxygen, and then filling oxygen with an initial pressure of 0.2 MPa; setting the reaction temperature to be 100-130 ℃ and the reaction time to be 1-3 h under the stirring state, rapidly cooling the reaction kettle to room temperature after the reaction is finished, analyzing the product by using gas chromatography, and collecting the product; the specific application is that methyl lactate is oxidized to obtain methyl pyruvate; oxidizing ethyl lactate to obtain ethyl pyruvate; butyl lactate is oxidized to obtain butyl pyruvate; the benzyl alcohol is oxidized to obtain benzaldehyde; furfuryl alcohol is oxidized to obtain furfural; carrying out an oxidation reaction on cinnamyl alcohol to obtain cinnamyl aldehyde; oxidizing n-propanol to obtain n-propanal;
the vanadium-based catalyst is prepared according to the following steps:
(1) Weighing a nitrogen-carbon precursor and vanadium salt, and grinding uniformly; wherein the nitrogen-carbon precursor is chitosan or chitin; the vanadium salt is VOSO 4 or VO (acac) 2;
(2) And (3) placing the obtained solid powder into a tube furnace, increasing the temperature from room temperature to a specified roasting temperature of 500-700 ℃, roasting to obtain a vanadium-based catalyst, and marking the vanadium-based catalyst as V-N-C_X, wherein X is a carrier prepared by different nitrogen-carbon precursors.
2. Use of the vanadium-based catalyst according to claim 1 in the oxidative dehydrogenation of hydroxyl-containing compounds, characterized in that: the mass ratio of the nitrogen-carbon precursor to the vanadium salt is 1-2: 1-4.
3. Use of the vanadium-based catalyst according to claim 1 in the oxidative dehydrogenation of hydroxyl-containing compounds, characterized in that: the mass molar ratio of the vanadium-based catalyst to the hydroxyl-containing compound is 30-50 mg:2mmol.
4. Use of the vanadium-based catalyst according to claim 1 in the oxidative dehydrogenation of hydroxyl-containing compounds, characterized in that: the organic solvent is one of acetonitrile, acetone, diethyl succinate and DMF.
5. Use of the vanadium-based catalyst according to claim 1 in the oxidative dehydrogenation of hydroxyl-containing compounds, characterized in that: the reaction temperature was 130℃and the reaction time was 3 hours.
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CN115368323A (en) * 2021-05-21 2022-11-22 矫文策 Method for preparing gamma-butyrolactone by catalytic oxidation of tetrahydrofurfuryl alcohol

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