CN112961130B - Two-dimensional MoS 2 Application of catalyst in preparation of succinic anhydride by catalyzing selective hydrogenation of maleic anhydride - Google Patents
Two-dimensional MoS 2 Application of catalyst in preparation of succinic anhydride by catalyzing selective hydrogenation of maleic anhydride Download PDFInfo
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- CN112961130B CN112961130B CN202110197523.XA CN202110197523A CN112961130B CN 112961130 B CN112961130 B CN 112961130B CN 202110197523 A CN202110197523 A CN 202110197523A CN 112961130 B CN112961130 B CN 112961130B
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- 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
- C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
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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
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
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Abstract
The invention relates to the field of catalysts, and particularly discloses a two-dimensional MoS 2 Application of catalyst in preparation of succinic anhydride by catalyzing selective hydrogenation of maleic anhydride, and two-dimensional MoS 2 The preparation method of the catalyst comprises the following steps: mixing ammonium molybdate and thiourea in water, reacting at 180-240 ℃ for 12-24 h, collecting a product after the reaction is finished, washing for multiple times and drying to obtain the two-dimensional MoS 2 A catalyst. Two-dimensional MoS of the invention 2 The catalyst has high conversion rate and high selectivity for preparing succinic anhydride by selective hydrogenation of maleic anhydride.
Description
Technical Field
The invention relates to the technical field of catalysts, in particular to a two-dimensional MoS 2 The catalyst is applied to the preparation of succinic anhydride by catalyzing the selective hydrogenation of maleic anhydride.
Background
Succinic anhydride is an important organic synthesis intermediate and a fine chemical raw material, and has very wide application in the fields of petrochemical industry, medicines, pesticides, foods and the like. The market price of succinic anhydride is 3800$/t, the price of its raw material maleic anhydride is 1900$/t, and the price of the over-hydrogenated product gamma-butyrolactone is only 1600$/t (Arias et al Biomass Conversion and Biorefinery 2020,10,1021-1033, woo-Sun Kim et al Clean Technology 2020,26,91-95, alqaheem et al chemistry Central Journal 2018, 12, 80). At present, succinic anhydride production faces a 'short supply and demand' situation on a global scale due to the limitation of raw materials and production modes.
The industrialized production method of succinic anhydride is mainly a maleic anhydride method and a succinic acid dehydration method. Compared with a succinic acid dehydration method, the maleic anhydride method has the advantages of simple process flow, separation and purification after the hydrogenation reaction is finished, and the like, so that the maleic anhydride liquid-phase hydrogenation method is widely adopted to produce succinic anhydride at home and abroad. However, deep hydrogenation products such as gamma-butyrolactone, tetrahydrofuran, 1,4 butanediol and the like are easy to occur in the maleic anhydride hydrogenation reaction.
Therefore, designing and developing a catalyst with proper activity to realize selective activation of maleic anhydride to generate succinic anhydride is a very challenging subject in the field of selective hydrogenation, and has great fundamental research significance and industrial application value.
Disclosure of Invention
The invention aims to solve the technical problem of providing a non-noble metal catalyst for catalyzing the hydrogenation reaction of maleic anhydride, so that the maleic anhydride can be converted into succinic anhydride by 100 percent.
In order to solve the technical problem, the invention provides a two-dimensional MoS 2 The catalyst is applied to the preparation of succinic anhydride by catalyzing the selective hydrogenation of maleic anhydride.
Further, the two-dimensional MoS 2 The synthesis method of the catalyst comprises the following steps:
and (2) mixing ammonium molybdate and thiourea in water, reacting at 180-240 ℃ for 12-24 h, collecting a product after the reaction is finished, washing for multiple times, and drying to obtain the two-dimensional MoS2 catalyst.
Further, the two-dimensional MoS 2 The synthesis method of the catalyst comprises the following steps:
using water as solvent, ammonium molybdate as precursor and thiourea as reducing agent, stirring them and uniformly mixing themReacting at 220 ℃ for 18h, cooling at room temperature, washing with water and ethanol for several times, and vacuum drying at 60 ℃ for 8h to obtain the two-dimensional MoS 2 A catalyst.
Further, the process for preparing succinic anhydride by catalyzing selective hydrogenation of maleic anhydride comprises the following steps:
adding maleic anhydride and two-dimensional MoS into a reaction vessel filled with a solvent 2 Catalyst, then introducing H into the reaction vessel 2 Heating to react until reaching the preset pressure, and continuously stirring in the reaction process; and after the reaction is finished, collecting a product to obtain succinic anhydride.
Further, the solvent is 1, 4-dioxane.
Further, H is introduced 2 The pressure of (A) is 2-6MPa.
Further, the temperature of the reaction is 95-120 ℃.
Further, the reaction time is 2-4h.
Further, H is firstly introduced into the reaction vessel for a plurality of times 2 To exhaust the air in the reaction vessel and introduce H 2 Until a predetermined pressure is reached.
Further, the two-dimensional MoS 2 When the catalyst is used for catalyzing the selective hydrogenation of the maleic anhydride, the conversion rate of the maleic anhydride and the selectivity of the succinic anhydride reach 100 percent.
The invention has the beneficial effects that:
1. commercial MoS containing only pure 2H configuration 2 The catalytic hydrogenation of maleic anhydride does not show any activity, and the unique 2D MoS is prepared by a hydrothermal synthesis method 2 The structure of which simultaneously comprises MoS in 1T configuration 2 And 2H configuration MoS 2 The 2D MoS 2 The catalyst has good activity for the selective hydrogenation of maleic anhydride.
2. Two-dimensional MoS synthesized by the invention 2 Catalyst, different reactions H at a wide operating temperature window (95 ℃ to 120 ℃) 2 The maleic anhydride is catalyzed for hydrogenation reaction under the conditions of pressure (2 to 6 MPa) and different reaction time (2 to 4 h), the selectivity of 100 percent can be kept, and the regulation activity is 19 to 100 percent.
Drawings
FIG. 1 shows different MoS 2 The catalyst catalyzes the reaction property of the maleic anhydride to prepare the succinic anhydride through selective hydrogenation;
FIG. 2 shows different MoS 2 A raman spectrum of the catalyst;
wherein: 2D MoS 2 Two-dimensional MoS synthesized for the invention 2 A catalyst; 800 ℃/6h/Ar MoS 2 Is 2D MoS which is subjected to heat treatment for 6h at 800 ℃ in Ar 2 ；300℃/4h/Air MoS 2 Is 2D MoS which is heat treated for 4 hours at 300 ℃ in air 2 ；Commercial MoS 2 For commercializing MoS 2 A catalyst.
Detailed Description
The present invention is further described below in conjunction with the following figures and specific examples so that those skilled in the art may better understand the present invention and practice it, but the examples are not intended to limit the present invention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
2 Synthetic MoS catalyst
The method comprises the steps of taking water as a solvent, ammonium molybdate as a precursor and thiourea as a reducing agent, mixing the materials uniformly by vigorous stirring, reacting the mixture for 18 hours at the temperature of 220 ℃, cooling the mixture at room temperature, washing the mixture for a plurality of times by using water and ethanol, and drying the washed mixture for 8 hours in vacuum at the temperature of 60 ℃ to obtain the two-dimensional MoS 2 Catalyst (2D MoS) 2 )。
The synthesized 2D MoS 2 Heat treatment is carried out for 6h in Ar at 800 ℃, and the obtained catalyst is 800 ℃/6h/Ar MoS 2 。
The synthesized 2D MoS 2 Heat treating at 300 deg.C for 4h in Air to obtain 300 deg.C/4 h/Air MoS catalyst 2 。
Catalytic test
All catalytic tests were performed in a 50mL autoclave. Adding MoS by using 1, 4-dioxane as a solvent and maleic anhydride as a reaction substrate 2 Is a catalyst. The reaction kettle is filled with H 2 Washing for 11 times to exhaust air in the kettle, and charging H 2 Until the set reaction pressure is reached. And then, gradually raising the reaction temperature to a set temperature to start the reaction, starting timing for 4 hours after the temperature reaches the set temperature, and continuously stirring in the reaction process. After the reaction, the product was analyzed by gas chromatography with an autosampler (GC-2060), and a hydrogen Flame Ionization Detector (FID) equipped with an SE-54 capillary column was used for the analysis of maleic anhydride, succinic anhydride, gamma-butyrolactone and 1, 4-butanediol.
Example 1
Two-dimensional MoS was added with 1, 4-dioxane (20 mL) as solvent and maleic anhydride (0.211 g) as reaction substrate 2 (0.4284 g) as a catalyst, reacting for 4h under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 105 ℃, and synthesizing succinic anhydride. The conversion of maleic anhydride was tested to be 19% and the selectivity to succinic anhydride was 100%.
Comparative example 1
1, 4-dioxane (20 mL) is used as a solvent, maleic anhydride (0.211 g) is used as a reaction substrate, and 800 ℃/6h/Ar MoS is added 2 (0.4284 g) as a catalyst, reacting for 4h under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 105 ℃, and synthesizing succinic anhydride. The conversion of maleic anhydride was tested to be 1% and the selectivity of succinic anhydride to be 100%.
Comparative example 2
1, 4-dioxane (20 mL) was used as a solvent, maleic anhydride (0.211 g) was used as a reaction substrate, and 300 ℃/4h/Air MoS was added 2 (0.4284 g) as a catalyst, reacting for 4h under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 105 ℃, and synthesizing succinic anhydride. The conversion of maleic anhydride was tested to be 0% and the selectivity of succinic anhydride was tested to be 0%.
Comparative example 3
Commercial MoS was added using 1, 4-dioxane (20 mL) as the solvent and maleic anhydride (0.211 g) as the substrate 2 (0.4284 g) as a catalyst, reacting for 4 hours under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 105 ℃, and synthesizing succinic anhydride. The conversion of maleic anhydride was tested to be 0% and the selectivity of succinic anhydride to be 0%.
Referring to FIG. 1, a two-dimensional MoS embodying the present invention is shown 2 The catalyst catalyzes the maleic anhydride to selectively hydrogenate and synthesize the succinic anhydride, the conversion rate of the maleic anhydride reaches 19 percent and is far higher than 800 ℃/6h/Ar MoS 2 Catalyst and selectivity up to 100%. Under the same reaction conditions, 300 ℃/4h/Air MoS 2 And Commercial MoS catalyst 2 Do not have any catalytic activity. From this, it is understood that MoS after the high-temperature treatment 2 The catalytic activity of the catalyst is significantly reduced.
Referring to FIG. 2, a Raman data diagram shows Commercial MoS 2 The configuration only contains 2H-MoS 2 And 2D-MoS 2 In addition to 2H-MoS 2 Besides the configuration, the material also comprises 1T-MoS 2 Configuration. And with the increase of the treatment temperature, 1T-MoS 2 The proportion of the configuration decreases in steps, which indicates that MoS 2 The main active role in catalyzing the hydrogenation reaction process of maleic anhydride is MoS with 1T configuration 2 。
Example 2
1, 4-dioxane (20 mL) was used as a solvent, maleic anhydride (0.1117 g) was used as a reaction substrate, and two-dimensional MoS was added 2 (0.908 g) as a catalyst, reacting for 4h under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 120 ℃ to synthesize succinic anhydride. The conversion of maleic anhydride was tested to be 100% and the selectivity of succinic anhydride to be 100%.
Example 3
Two-dimensional MoS was added using 1, 4-dioxane (20 mL) as the solvent and maleic anhydride (0.1117 g) as the reaction substrate 2 (0.454 g) as a catalyst, reacting for 4 hours under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 120 ℃ to synthesize the succinic anhydride. The conversion of maleic anhydride was tested to be 71%, andthe selectivity to succinic anhydride was 100%.
Example 4
Two-dimensional MoS was added using 1, 4-dioxane (20 mL) as the solvent and maleic anhydride (0.1117 g) as the reaction substrate 2 (0.908 g) as a catalyst, reacting for 4 hours under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 105 ℃, and synthesizing succinic anhydride. The conversion of maleic anhydride was tested to be 74% and the selectivity to succinic anhydride was 100%.
Example 5
Two-dimensional MoS was added using 1, 4-dioxane (20 mL) as the solvent and maleic anhydride (0.1117 g) as the reaction substrate 2 (0.908 g) as a catalyst, reacting for 4 hours under the conditions that the reaction pressure is 0.2MPa and the reaction temperature is 120 ℃ to synthesize the succinic anhydride. The conversion of maleic anhydride was tested to be 27% and the selectivity to succinic anhydride was 100%.
Example 6
1, 4-dioxane (20 mL) was used as a solvent, maleic anhydride (0.1117 g) was used as a reaction substrate, and two-dimensional MoS was added 2 (0.908 g) as a catalyst, reacting for 4h under the conditions that the reaction pressure is 0.4MPa and the reaction temperature is 120 ℃, and synthesizing succinic anhydride. The conversion of maleic anhydride was tested to be 53% and the selectivity of succinic anhydride to be 100%.
Example 7
Two-dimensional MoS was added using 1, 4-dioxane (20 mL) as the solvent and maleic anhydride (0.1117 g) as the reaction substrate 2 (0.908 g) as a catalyst, reacting for 4 hours under the conditions that the reaction pressure is 0.5MPa and the reaction temperature is 120 ℃ to synthesize the succinic anhydride. The conversion of maleic anhydride was tested to be 81% and the selectivity of succinic anhydride to be 100%.
Example 8
1, 4-dioxane (20 mL) was used as a solvent, maleic anhydride (0.1863 g) was used as a reaction substrate, and two-dimensional MoS was added 2 (0.3785 g) is used as a catalyst to react for 4h under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 95 ℃ to synthesize succinic anhydride. The conversion of maleic anhydride was tested to be 18.7% and the selectivity to succinic anhydride was 35.7%.
Example 9
Two-dimensional MoS was added using 1, 4-dioxane (20 mL) as the solvent and maleic anhydride (0.1117 g) as the reaction substrate 2 (0.454 g) as a catalyst, reacting for 4h under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 95 ℃ to synthesize succinic anhydride. The conversion of maleic anhydride was tested to be 23% and the selectivity of succinic anhydride to be 100%.
Example 10
1, 4-dioxane (20 mL) was used as a solvent, maleic anhydride (0.1117 g) was used as a reaction substrate, and two-dimensional MoS was added 2 (0.908 g) as a catalyst, reacting for 4h under the conditions that the reaction pressure is 0.6MPa and the reaction temperature is 105 ℃, and synthesizing succinic anhydride. The conversion of maleic anhydride was tested to be 44% and the selectivity to succinic anhydride was 100%.
In conclusion, the unique 2D MoS prepared by hydrothermal synthesis method of the invention 2 The catalyst has good activity for selective hydrogenation of maleic anhydride, and can be used for catalyzing selective hydrogenation of maleic anhydride to prepare succinic anhydride.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitutions or changes made by the person skilled in the art on the basis of the present invention are all within the protection scope of the present invention. The protection scope of the invention is subject to the claims.
Claims (9)
1. Two-dimensional MoS 2 The application of the catalyst in catalyzing selective hydrogenation of maleic anhydride to prepare succinic anhydride; wherein the two-dimensional MoS 2 The synthesis method of the catalyst comprises the following steps:
mixing ammonium molybdate and thiourea in water, reacting at 180-240 ℃ for 12-24h, collecting a product after the reaction is finished, washing for many times, and drying to obtain the two-dimensional MoS 2 A catalyst.
2. The use according to claim 1, wherein the two-dimensional MoS 2 The synthesis method of the catalyst comprises the following steps:
using water as a solvent, ammonium molybdate as a precursor and thiourea as a reducing agent, stirring to uniformly mix the materials, reacting at 220 ℃ for 18h, cooling at room temperature, washing with water and ethanol for several times, and vacuum drying at 60 ℃ for 8h to obtain the two-dimensional MoS 2 A catalyst.
3. The use according to claim 1, wherein the process for preparing succinic anhydride by catalytic selective hydrogenation of maleic anhydride comprises:
adding maleic anhydride and two-dimensional MoS into a reaction vessel filled with a solvent 2 Catalyst, then feeding H into the reaction vessel 2 Heating to react until reaching the preset pressure, and continuously stirring in the reaction process; and after the reaction is finished, collecting a product to obtain succinic anhydride.
4. Use according to claim 3, wherein the solvent is 1, 4-dioxane.
5. Use according to claim 3, wherein H is introduced 2 The pressure of (A) is 2-6MPa.
6. Use according to claim 3, wherein the temperature of the reaction is 95-120 ℃.
7. Use according to claim 3, wherein the reaction time is 2-4h.
8. The use of claim 3, wherein H is first introduced into the reaction vessel a plurality of times 2 To exhaust the air in the reaction vessel and then introduce H 2 Until a predetermined pressure is reached.
9. Use according to claim 3, wherein the two-dimensional MoS is 2 When the catalyst is used for catalyzing the selective hydrogenation of the maleic anhydride, the conversion rate of the maleic anhydride and the selectivity of the succinic anhydride reach 100 percent.
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