CN107597159B - Catalyst for preparing succinic anhydride by maleic anhydride hydrogenation and preparation method thereof - Google Patents
Catalyst for preparing succinic anhydride by maleic anhydride hydrogenation and preparation method thereof Download PDFInfo
- Publication number
- CN107597159B CN107597159B CN201710815713.7A CN201710815713A CN107597159B CN 107597159 B CN107597159 B CN 107597159B CN 201710815713 A CN201710815713 A CN 201710815713A CN 107597159 B CN107597159 B CN 107597159B
- Authority
- CN
- China
- Prior art keywords
- catalyst
- silicon carbide
- maleic anhydride
- precursor
- succinic anhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Abstract
The pore volume of the catalyst for preparing succinic anhydride by maleic anhydride hydrogenation is 0.1-0.4 cm3A specific surface area of 90 to 400 m/g2The pore diameter is 1-11 nm. The active component nickel content is 7.5-15%, the assistant metal content is 0.2-1.2%, and the rest is silicon carbide ordered mesoporous material. The invention has the advantages of good thermal stability, good activity and high selectivity.
Description
Technical Field
The invention relates to a hydrogenation catalyst, in particular to a catalyst for synthesizing succinic anhydride by maleic anhydride liquid-phase hydrogenation and a preparation method thereof.
Background
Succinic Anhydride (SA), also known as Succinic anhydride, is a colorless, flaky or needle-shaped crystal, slightly pungent in odor, soluble in chloroform, alcohol and carbon tetrachloride, slightly soluble in ether and water. Due to the unique molecular structure, succinic anhydride can be subjected to reactions such as alcoholysis, hydrolysis, halogenation, esterification, acylation and the like, and is widely applied to the fields of medicines, pesticides, food additives, petrochemical industry and the like. At present, succinic anhydride is produced mainly by a succinic acid dehydration method and a maleic anhydride hydrogenation method. Wherein, the maleic anhydride hydrogenation method has the advantages of simple process flow, remarkable economic and ecological benefits and the like, and has higher industrial application prospect. In recent years, the interest of researchers has been increasing.
For the chemical reaction, noble metal catalysts have high activity and anti-carbon deposition performance, but because of high price and limited resources, non-noble metal catalysts are generally researched. The Ni-based catalyst is one of the catalytic systems with excellent catalytic performance for the maleic anhydride liquid-phase hydrogenation reaction except for the noble metal catalyst, but the catalyst is easy to deposit carbon in the reaction process and has poor sintering resistance, so that the catalyst is quickly inactivated.
Although the catalyst above the ordered mesoporous pore channel utilizes the confinement effect of the mesoporous material to limit the growth of Ni nanoparticles, the skeleton of the mesoporous silica material is obviously shrunk after high-temperature treatment, so that the parameters such as specific surface, pore volume, pore diameter and the like are severely reduced, and the low thermal stability of the mesoporous silica material enables the reaction activity of the catalyst at high temperature to be reduced, so that the catalyst is inactivated.
Disclosure of Invention
The invention aims to provide a catalyst for preparing succinic anhydride by maleic anhydride hydrogenation, which has good thermal stability, good activity and high selectivity, and a preparation method thereof.
The invention provides a method for preparing a Ni-based catalyst by using non-oxide mesoporous silicon carbide as a carrier of the Ni-based catalyst, which prevents the growth and aggregation of nickel metal particles, has a limited domain effect on Ni nano particles, has the specific high-temperature structural stability, improves the sintering resistance and the carbon deposition resistance of the catalyst, and utilizes the high thermal stability and the chemical inertness of the silicon carbide to ensure that the prepared catalyst still keeps good activity and stability under high-temperature reaction.
In order to realize the purpose, the catalyst for preparing succinic anhydride by maleic anhydride hydrogenation is a catalyst for preparing succinic anhydride by firstly synthesizing a silicon carbide ordered mesoporous material taking SBA-15, KIT-6, MCM-41, SBA-16 and MCM-48 as templates and then loading active bimetal on a silicon carbide material by an adsorption and impregnation method to form loaded maleic anhydride with ordered mesoporous channels through hydrogenation.
The pore volume of the catalyst for preparing succinic anhydride by maleic anhydride hydrogenation is 0.1-0.4 cm3A specific surface area of 90 to 400 m/g2The pore diameter is 1-11 nm. The active component nickel content is 7.5-15%, the assistant metal content is 0.2-1.2%, and the rest is silicon carbide ordered mesoporous material.
The preparation method of the catalyst for preparing succinic anhydride by maleic anhydride hydrogenation comprises the following steps:
(1) according to the silicon carbide precursor: the weight ratio of the dimethylbenzene is 1: 5-20, mixing the silicon carbide precursor and xylene, dissolving under stirring, adding the ordered mesoporous template raw material after complete dissolution, and performing reduced pressure rotary evaporation or magnetic stirring until xylene is completely volatilized to obtain a sample 1;
(2) drying the sample 1 in the step (1) at 80-120 ℃ for 12-24 h, then heating to 200-400 ℃ at a heating rate of 0.5-5 ℃/min under a nitrogen atmosphere, keeping the temperature for 2-6 h, then heating to 600-900 ℃ at a heating rate of 0.5-5 ℃/min, keeping the temperature for 1-5 h, crosslinking and pyrolyzing the silicon carbide precursor, and finally heating to 1200-1400 ℃ at a heating rate of 0.5-5 ℃/min, keeping the temperature for 1-3 h, thus obtaining a sample 2;
(3) as per sample 2: the mixed solution is 1 g: 10-100 mL, adding the sample 2 obtained in the step (2) into the mixed solution, stirring for 12-24 h, filtering and washing with water, and finally drying at 80-120 ℃ for 12-24 h to obtain the silicon carbide ordered mesoporous material;
(4) dissolving a nickel precursor, an auxiliary agent precursor and a dispersing agent in water according to the composition of the catalyst, wherein the adding amount of the dispersing agent is the total mass of the nickel precursor and the auxiliary agent precursor, then dropwise adding the dispersing agent into the silicon carbide ordered mesoporous material, continuously stirring, and stirring for 2-24 h after all the dispersing agent is completely dropwise added. Then, the sample is subjected to ultrasonic treatment for 10 min-2 h, dried at 80-120 ℃ for 12-24 h, and heated to 500-750 ℃ at a heating rate of 0.5-5 ℃/min under a flowing inert atmosphere to remove residues, so as to obtain the catalyst.
In the step (1), the silicon carbide precursor is one or two of polysilane, polycarbosilane and polymethylsilane.
The medium pore template raw material in the step (1) is one of SBA-15, KIT-6, MCM-41, SBA-16 and MCM-48 molecular sieves.
In the step (1), the mass ratio of the silicon carbide precursor to the mesoporous template raw material is 1: 0.4-1.2.
And (3) mixing ethanol, water and hydrofluoric acid at a volume ratio of 1: 1-2: 0.5-2.
The nickel salt in the step (4) is nickel nitrate.
The dispersant in the step (4) is one of polyethylene glycol, polyoxyethylene-polyoxypropylene-polyoxyethylene, cetyl trimethyl ammonium bromide and polyvinylpyrrolidone.
The type of the auxiliary agent precursor salt in the step (4) is one of cobalt nitrate, ferric nitrate, cupric nitrate, zinc nitrate and manganese nitrate.
The addition amount of water in the step (4): the mass of the silicon carbide ordered mesoporous material is 3-10 mL: 1g of the total weight of the composition.
And (3) the flowing inert atmosphere in the step (6) is one of flowing nitrogen, argon or helium.
The application conditions of the catalyst in the maleic anhydride liquid phase hydrogenation reaction are as follows:
the reaction was carried out in a 100mL autoclave under the following conditions: the hydrogen pressure is 5MPa, the temperature is 210 ℃, the catalyst is 0.3g, the maleic anhydride is 4.9g, and the tetrahydrofuran solvent is 40 mL.
The invention has the advantages of good thermal stability, good activity and high selectivity, and the nickel-loaded ordered mesoporous silicon carbide catalyst prepared by the method can ensure that the conversion rate of maleic anhydride is more than or equal to 97 percent and the selectivity of succinic anhydride is more than 98 percent.
Drawings
FIG. 1 is a high resolution transmission electron micrograph of the catalyst of example 1;
FIG. 2 is N for the catalyst of example 22An adsorption-desorption curve;
figure 3 is an XRD pattern of the catalyst of example 3.
Detailed Description
The present invention is further illustrated by the following specific examples.
Example 1: weighing 6.0g of polysilane and 30g of xylene solution at room temperature, mixing, dissolving under stirring, adding 7.2g of mesoporous template raw material SBA-15 after complete dissolution, and stirring by reduced pressure rotary evaporation until xylene is basically volatilized. The sample was transferred to a drying oven at 80 ℃ for 24 h. Then heating to 200 ℃ at a heating rate of 1 ℃/min under a nitrogen atmosphere, keeping for 5h, then heating to 600 ℃ at a heating rate of 0.5 ℃/min, keeping for 1h to crosslink and pyrolyze the polysilane, and finally heating to 1200 ℃ at a heating rate of 1 ℃/min, and keeping for 3 h. And adding 5.0g of the obtained sample into a mixed solution of 50mL of ethanol, water and hydrofluoric acid at a volume ratio of 1: 0.5, stirring for 12h, filtering and washing, and finally drying at 80 ℃ for 24h to obtain the ordered mesoporous silicon carbide carrier m-SiC-1 with the SBA-15-like template pore channel structure.
Weighing 1.21g of nickel nitrate, 0.03g of cobalt nitrate and 1.24g of polyethylene glycol dispersant, adding 9mL of water to dissolve the mixture, dropwise adding the mixture into 3.0g of the prepared ordered mesoporous silicon carbide carrier, continuously stirring the mixture, stirring the mixture for 24 hours after all the mixture is dropwise added, then carrying out ultrasonic treatment on the sample for 10 minutes, drying the sample for 24 hours at 80 ℃, heating the sample to 500 ℃ at the heating rate of 1 ℃/min under the flowing nitrogen atmosphere, and removing residues to obtain the ordered mesoporous nickel-based silicon carbide catalyst 7.5Ni-0.2 Co/m-SiC-1.
Example 2: weighing 6.0g of polycarbosilane and 55g of xylene solution at room temperature, mixing, dissolving under stirring, adding 5.0g of mesoporous template raw material KIT-6 after complete dissolution, and stirring by magnetic force until xylene is basically volatilized. The sample was transferred to a 95 ℃ drying oven for 17 h. Then heating to 320 ℃ at a heating rate of 2 ℃/min under a nitrogen atmosphere, keeping the temperature for 4.5h, then heating to 720 ℃ at a heating rate of 0.5 ℃/min, keeping the temperature for 2.5h to crosslink and pyrolyze the polycarbosilane, and finally heating to 1280 ℃ at a heating rate of 2 ℃/min, and keeping the temperature for 2.5 h. And adding 5.0g of the obtained sample into 240mL of mixed solution of ethanol, water and hydrofluoric acid at a volume ratio of 1: 1, stirring for 16h, filtering and washing, and drying at 100 ℃ for 18h to obtain the KIT-6-like template pore canal structure ordered mesoporous silicon carbide carrier m-SiC-2.
Weighing 1.39g of nickel nitrate, 0.08g of ferric nitrate and 1.47g of polyoxyethylene-polyoxypropylene-polyoxyethylene dispersant, adding 15mL of water to dissolve the nickel nitrate, dropwise adding the mixture into 3.0g of the prepared ordered mesoporous silicon carbide carrier, continuously stirring, stirring for 19h after all the mixture is dropwise added, then carrying out ultrasonic treatment on the sample for 20min, drying for 18h at 100 ℃, heating to 580 ℃ at a heating rate of 2 ℃/min under a flowing argon atmosphere, and removing residues to obtain the ordered mesoporous nickel-based silicon carbide catalyst 8.5Ni-0.5 Fe/m-SiC-2.
Example 3: weighing 6.0g of polymethylsilane and 90g of xylene solution at room temperature, mixing, dissolving under stirring, adding 4.0g of mesoporous template material MCM-41 after complete dissolution, and stirring by reduced pressure rotary evaporation until xylene is basically volatilized. The sample was transferred to a drying oven at 105 ℃ for 14 h. Then heating to 360 ℃ at a heating rate of 4 ℃/min under a nitrogen atmosphere, keeping the temperature for 2.5h, then heating to 820 ℃ at a heating rate of 1 ℃/min, keeping the temperature for 3.5h to crosslink and pyrolyze the polymethyl silane, and finally heating to 1320 ℃ at a heating rate of 4 ℃/min, and keeping the temperature for 2 h. And adding 5.0g of the obtained sample into 320mL of mixed solution of ethanol, water and hydrofluoric acid at a volume ratio of 1: 2, stirring for 19h, filtering and washing with water, and finally drying at 110 ℃ for 16h to obtain the ordered mesoporous silicon carbide carrier m-SiC-3 with the MCM-41-like template pore channel structure.
Weighing 1.67g of nickel nitrate, 0.10g of copper nitrate and 1.77g of hexadecyl trimethyl ammonium bromide dispersing agent, adding 18mL of water to dissolve, dropwise adding the mixture into 3.0g of the prepared ordered mesoporous silicon carbide carrier, continuously stirring, stirring for 17 hours after all the mixture is dropwise added, then carrying out ultrasonic treatment on the sample for 50 minutes, drying for 16 hours at 110 ℃, heating to 630 ℃ at a heating rate of 4 ℃/min under a flowing helium atmosphere, and removing residues to obtain the ordered mesoporous nickel-based silicon carbide catalyst 10Ni-0.8 Cu/m-SiC-3.
Example 4: at room temperature, 6.0g of a mixture of polysilane and polycarbosilane with the same mass is weighed and mixed with 120g of xylene solution, dissolved under stirring, 3.0g of mesoporous template raw material SBA-16 is added after complete dissolution, and stirring is carried out by reduced pressure rotary evaporation until xylene is basically volatilized. The sample was transferred to a drying oven at 120 ℃ for drying for 13 h. Then heating to 400 ℃ at a heating rate of 5 ℃/min under a nitrogen atmosphere, keeping the temperature for 1h, then heating to 900 ℃ at a heating rate of 5 ℃/min, keeping the temperature for 4h to crosslink and pyrolyze the polysilane and the polycarbosilane, and finally heating to 1380 ℃ at a heating rate of 5 ℃/min, keeping the temperature for 3 h. And adding 5.0g of the obtained sample into 400mL of mixed solution of ethanol, water and hydrofluoric acid at a volume ratio of 1: 2: 0.5, stirring for 24h, filtering and washing, and finally drying at 120 ℃ for 12h to obtain the ordered mesoporous silicon carbide carrier m-SiC-4 with the SBA-16-like template pore channel structure.
Weighing 2.05g of nickel nitrate, 0.16g of zinc nitrate and 2.21g of polyvinylpyrrolidone dispersing agent, adding 24mL of water to dissolve the mixture, dropwise adding the mixture into 3.0g of the prepared ordered mesoporous silicon carbide carrier, continuously stirring, stirring for 15h after all the mixture is dropwise added, then carrying out ultrasonic treatment on the sample for 100min, drying for 12h at 120 ℃, heating to 720 ℃ at a heating rate of 5 ℃/min under a flowing nitrogen atmosphere, and removing residues to obtain the ordered mesoporous nickel-based silicon carbide catalyst 12Ni-1 Zn/m-SiC-4.
Example 5: weighing 6.0g of polysilane and polymethylsilane mixture with the same mass at room temperature, mixing with 105g of xylene solution, dissolving under stirring, adding 4.5g of mesoporous template raw material MCM-48 after complete dissolution, and stirring by magnetic force until xylene is basically volatilized. The sample was transferred to a 115 ℃ drying cabinet for drying for 22 h. Then heating to 380 ℃ at a heating rate of 3 ℃/min under a nitrogen atmosphere, keeping the temperature for 3h, then heating to 880 ℃ at a heating rate of 3 ℃/min, keeping the temperature for 5h to crosslink and pyrolyze the polysilane and the polymethylsilane, and finally heating to 1400 ℃ at a heating rate of 3 ℃/min, and keeping the temperature for 1 h. Adding 5.0g of the obtained sample into 500mL of mixed solution of ethanol, water and hydrofluoric acid at a volume ratio of 1: 2: 1, stirring for 21h, filtering and washing with water, and drying at 110 ℃ for 20h to obtain the ordered mesoporous silicon carbide carrier m-SiC-5 with the MCM-48-like template pore channel structure.
Weighing 2.66g of nickel nitrate, 0.20g of manganese nitrate and 2.86g of polyethylene glycol dispersant, adding water into 30mL of water, dissolving, dropwise adding into 3.0g of the prepared ordered mesoporous silicon carbide carrier, continuously stirring, stirring for 7h after all dropwise adding is finished, then carrying out ultrasonic treatment on the sample for 1.5h, drying for 20h at 110 ℃, heating to 750 ℃ at a heating rate of 3 ℃/min under a flowing argon atmosphere, and removing residues to obtain the ordered mesoporous nickel-based silicon carbide catalyst 15Ni-1.2 Mn/m-SiC-5.
Physicochemical characteristic parameters of the nickel-based silicon carbide-supported catalysts prepared in examples 1 to 5 are shown in Table 1.
TABLE 1 physicochemical Properties of Nickel-based silicon carbide Supported catalysts
The use of the catalysts of examples 1-5 in the liquid phase hydrogenation of maleic anhydride is further illustrated below.
Application 1: 0.3g of 40-60 mesh catalyst particles of example 1 and 4.9g of maleic anhydride were weighed and placed in an autoclave, 40mL of tetrahydrofuran was added, the reaction was carried out at a reaction temperature of 210 ℃ under a hydrogen pressure of 5MPa for 3 hours, and the product was analyzed by gas chromatography.
Application 2: 0.3g of 40-60 mesh catalyst particles of example 2 and 4.9g of maleic anhydride were weighed and placed in an autoclave, 40mL of tetrahydrofuran was added, the reaction was carried out at a reaction temperature of 210 ℃ under a hydrogen pressure of 5MPa for 3 hours, and the product was analyzed by gas chromatography.
Application 3: 0.3g of 40-60 mesh catalyst particles of example 3 and 4.9g of maleic anhydride were weighed and placed in an autoclave, 40mL of tetrahydrofuran was added, the reaction was carried out at a reaction temperature of 210 ℃ under a hydrogen pressure of 5MPa for 3 hours, and the product was analyzed by gas chromatography.
Application 4: 0.3g of 40-60 mesh example 4 catalyst particles and 4.9g of maleic anhydride were weighed and placed in an autoclave, 40mL of tetrahydrofuran was added, the reaction was carried out at a reaction temperature of 210 ℃ under a hydrogen pressure of 5MPa for 3 hours, and the product was analyzed by gas chromatography.
Application 5: 0.3g of 40-60 mesh example 5 catalyst particles and 4.9g of maleic anhydride were weighed and placed in an autoclave, 40mL of tetrahydrofuran was added, the reaction was carried out at a reaction temperature of 210 ℃ under a hydrogen pressure of 5MPa for 3 hours, and the product was analyzed by gas chromatography.
TABLE 2 liquid-phase hydrogenation results of maleic anhydride catalyzed by nickel-based silicon carbide supported catalyst
Claims (8)
1. A catalyst for preparing succinic anhydride by maleic anhydride hydrogenation is characterized in that the pore volume of the catalyst is 0.1-0.4 cm3A specific surface area of 90 to 400 m/g2The pore diameter is 1-11 nm, the content of active component nickel is 7.5-15%, the content of auxiliary metal is 0.2-1.2%, and the rest is silicon carbide ordered mesoporous material; the auxiliary metal is one of cobalt, iron, copper, zinc or manganese;
the preparation method of the catalyst comprises the following steps:
(1) according to the silicon carbide precursor: the weight ratio of the dimethylbenzene is 1: 5-20, mixing the silicon carbide precursor and xylene, dissolving under stirring, adding the ordered mesoporous template raw material after complete dissolution, and performing reduced pressure rotary evaporation or magnetic stirring until xylene is completely volatilized to obtain a sample 1;
(2) drying the sample 1 in the step (1) at 80-120 ℃ for 12-24 h, then heating to 200-400 ℃ at a heating rate of 0.5-5 ℃/min under a nitrogen atmosphere, keeping the temperature for 2-6 h, then heating to 600-900 ℃ at a heating rate of 0.5-5 ℃/min, keeping the temperature for 1-5 h, crosslinking and pyrolyzing the silicon carbide precursor, and finally heating to 1200-1400 ℃ at a heating rate of 0.5-5 ℃/min, keeping the temperature for 1-3 h, thus obtaining a sample 2;
(3) as per sample 2: the mixed solution is 1 g: 10-100 mL, adding the sample 2 obtained in the step (2) into the mixed solution, stirring for 12-24 h, filtering and washing with water, and finally drying at 80-120 ℃ for 12-24 h to obtain the silicon carbide ordered mesoporous material;
(4) dissolving a nickel precursor, an auxiliary agent precursor and a dispersing agent in water according to the composition of a catalyst, wherein the adding amount of the dispersing agent is the total mass of the nickel precursor and the auxiliary agent precursor, then dropwise adding the dispersing agent into the silicon carbide ordered mesoporous material, continuously stirring, stirring for 2-24 h after all the dispersing agent is completely dropwise added, then carrying out ultrasonic treatment on a sample for 10-2 h, drying for 12-24 h at 80-120 ℃, heating to 500-750 ℃ at a heating rate of 0.5-5 ℃/min under a flowing inert atmosphere, and removing residues to obtain the catalyst;
the ordered mesoporous template raw material in the step (1) is one of SBA-15, KIT-6, MCM-41, SBA-16 and MCM-48 molecular sieves;
the mixed liquid in the step (3) is ethanol, water and hydrofluoric acid in a volume ratio of 1: 1-2: 0.5-2.
2. The catalyst for preparing succinic anhydride by hydrogenating maleic anhydride according to claim 1, wherein the silicon carbide precursor in the step (1) is one or two of polysilane, polycarbosilane and polymethylsilane.
3. The catalyst for preparing succinic anhydride by hydrogenating maleic anhydride according to claim 1, wherein the mass ratio of the silicon carbide precursor to the ordered mesoporous template raw material in the step (1) is 1: 0.4-1.2.
4. The catalyst for preparing succinic anhydride by hydrogenating maleic anhydride as claimed in claim 1, wherein the nickel precursor in the step (4) is nickel nitrate.
5. The catalyst for preparing succinic anhydride by hydrogenating maleic anhydride as claimed in claim 1, wherein the dispersant in the step (4) is one of polyethylene glycol, polyoxyethylene-polyoxypropylene-polyoxyethylene, cetyl trimethyl ammonium bromide, and polyvinylpyrrolidone.
6. The catalyst for preparing succinic anhydride by hydrogenating maleic anhydride according to claim 1, wherein the kind of the precursor of the assistant in the step (4) is one of cobalt nitrate, ferric nitrate, copper nitrate, zinc nitrate and manganese nitrate.
7. The catalyst for preparing succinic anhydride by hydrogenating maleic anhydride as claimed in claim 1, wherein the amount of water added in the step (4) is: the mass of the silicon carbide ordered mesoporous material is 3-10 mL: 1g of the total weight of the composition.
8. The catalyst for preparing succinic anhydride by hydrogenating maleic anhydride as claimed in claim 1, wherein the flowing inert atmosphere in the step (4) is one of flowing nitrogen, argon or helium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710815713.7A CN107597159B (en) | 2017-09-12 | 2017-09-12 | Catalyst for preparing succinic anhydride by maleic anhydride hydrogenation and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710815713.7A CN107597159B (en) | 2017-09-12 | 2017-09-12 | Catalyst for preparing succinic anhydride by maleic anhydride hydrogenation and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107597159A CN107597159A (en) | 2018-01-19 |
| CN107597159B true CN107597159B (en) | 2020-06-12 |
Family
ID=61062602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710815713.7A Active CN107597159B (en) | 2017-09-12 | 2017-09-12 | Catalyst for preparing succinic anhydride by maleic anhydride hydrogenation and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107597159B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108132316A (en) * | 2018-02-10 | 2018-06-08 | 浙江华海药业股份有限公司 | A kind of method of succinic anhydride content in gas chromatographic detection sample |
| CN108709948A (en) * | 2018-04-27 | 2018-10-26 | 河南能源化工集团鹤壁煤化工有限公司 | A method of quickly measuring industrial succinic anhydride purity using gas chromatography |
| CN109529850A (en) * | 2018-12-19 | 2019-03-29 | 山西大学 | A kind of nisiloy catalyst and its preparation method and application |
| CN113231069B (en) * | 2021-04-15 | 2024-02-06 | 云南大为恒远化工有限公司 | Maleic anhydride bulk hydrogenation succinic anhydride preparation composite efficient catalyst and preparation method thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666412A (en) * | 1968-10-21 | 1972-05-30 | Du Pont | Dispersed phase activated and stabilized metal catalysts |
| CN1106714A (en) * | 1994-07-05 | 1995-08-16 | 化学工业部北京化工研究院 | Maleic anhydride catalyst with heavy rare earth oxide and its application |
| CN1453066A (en) * | 2003-04-30 | 2003-11-05 | 山西大学 | Catalyst for hydrogenating cis-butenedioic anhydride to prepare butanedioic anhydride and its prepn and application |
| EP2144698A2 (en) * | 2007-05-02 | 2010-01-20 | Sicat | Composite consisting of nanotubes or nanofibres on a b-sic film |
| CN101844976A (en) * | 2010-04-27 | 2010-09-29 | 湖南长岭石化科技开发有限公司 | Method for preparing butanedioic acid under catalytic hydrogenation |
| CN103769105A (en) * | 2012-10-24 | 2014-05-07 | 中国石油化工股份有限公司 | Catalyst for hydrogenating cis-butenedioic anhydride to prepare butanedioic anhydride and its preparation method and application |
| CN104607204A (en) * | 2015-01-29 | 2015-05-13 | 武汉科林精细化工有限公司 | Catalyst for continuously producing succinic anhydride by hydrogenating maleic anhydride and preparation method of catalyst |
-
2017
- 2017-09-12 CN CN201710815713.7A patent/CN107597159B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666412A (en) * | 1968-10-21 | 1972-05-30 | Du Pont | Dispersed phase activated and stabilized metal catalysts |
| CN1106714A (en) * | 1994-07-05 | 1995-08-16 | 化学工业部北京化工研究院 | Maleic anhydride catalyst with heavy rare earth oxide and its application |
| CN1453066A (en) * | 2003-04-30 | 2003-11-05 | 山西大学 | Catalyst for hydrogenating cis-butenedioic anhydride to prepare butanedioic anhydride and its prepn and application |
| EP2144698A2 (en) * | 2007-05-02 | 2010-01-20 | Sicat | Composite consisting of nanotubes or nanofibres on a b-sic film |
| CN101844976A (en) * | 2010-04-27 | 2010-09-29 | 湖南长岭石化科技开发有限公司 | Method for preparing butanedioic acid under catalytic hydrogenation |
| CN103769105A (en) * | 2012-10-24 | 2014-05-07 | 中国石油化工股份有限公司 | Catalyst for hydrogenating cis-butenedioic anhydride to prepare butanedioic anhydride and its preparation method and application |
| CN104607204A (en) * | 2015-01-29 | 2015-05-13 | 武汉科林精细化工有限公司 | Catalyst for continuously producing succinic anhydride by hydrogenating maleic anhydride and preparation method of catalyst |
Non-Patent Citations (2)
| Title |
|---|
| "Highly stable Ni/SiC catalyst modified by Al2O3 for CO methanation reaction";Guojing Jin等;《RSC Advances》;20160115;第6卷;9631-9639 * |
| "载体对镍基催化剂顺酐液相加氢性能的影响";张因等;《化工学报》;20150731;第66卷(第7期);2505-2513 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107597159A (en) | 2018-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107597159B (en) | Catalyst for preparing succinic anhydride by maleic anhydride hydrogenation and preparation method thereof | |
| Cui et al. | Pd-doped Ni nanoparticle-modified N-doped carbon nanocatalyst with high Pd atom utilization for the transfer hydrogenation of nitroarenes | |
| CN105032424B (en) | A kind of catalyst and preparation method thereof for aromatic nitro compound selective hydrogenation | |
| CN103303903B (en) | Metal or metal oxide loaded mesoporous carbon material and preparation method thereof | |
| CN110756225B (en) | Metal/MOFs nano catalyst and preparation method and application thereof | |
| JP2020528499A (en) | Carbon-coated transition metal nanocomposites, their manufacture and applications | |
| Ma et al. | Biosynthesized ruthenium nanoparticles supported on carbon nanotubes as efficient catalysts for hydrogenation of benzene to cyclohexane: An eco-friendly and economical bioreduction method | |
| WO2017207555A1 (en) | Preparation of mesoporous carbon with catalytically active metal oxide nanoparticles for the selective hydrogenation of alpha-beta-unsaturated aldehydes | |
| CN103008012A (en) | Metal organic skeleton structure material load platinum catalyst, as well as preparation method and application thereof | |
| CN109701529B (en) | High-dispersion dehydrogenation catalyst, preparation method and use method | |
| CN110152654B (en) | Ordered mesoporous carbon-TiO 2 Composite material supported palladium catalyst, preparation method and application thereof | |
| CN113145144B (en) | Ni 3 P/SiO 2 Catalyst, preparation method and application thereof | |
| Wang et al. | Ceria-promoted Co@ NC catalyst for biofuel upgrade: synergy between ceria and cobalt species | |
| CN113750993B (en) | Palladium monoatomic catalyst, preparation method thereof and application thereof in Suzuki coupling reaction | |
| CN108371953A (en) | It is a kind of for the BCN catalyst of Knoevenagel condensation reactions and its preparation and application | |
| CN109647517A (en) | One kind being used for nitro benzene and its derivative hydrogenation catalyst preparation method | |
| CN110152703A (en) | A kind of N doping ordered mesopore carbon load nano palladium material and preparation method thereof | |
| CN111604051A (en) | Lignin-based ordered mesoporous carbon catalyst and preparation method and application thereof | |
| CN113351214B (en) | Carbon-doped silicon dioxide-loaded nickel-copper alloy and preparation method and application thereof | |
| CN111111649A (en) | Heteroatom-modified Pd nano catalytic material and preparation method and application thereof | |
| CN109701520B (en) | High-dispersion dehydrogenation catalyst, preparation method and application method | |
| CN112295580B (en) | Sodium carbonate supported palladium-copper nano catalyst and application thereof in preparation of olefin by catalytic hydrogenation of alkyne | |
| CN107970920A (en) | High dispersion metal material and purposes | |
| CN107497470B (en) | Nickel-loaded silicon carbide catalyst for methane and carbon dioxide reforming reaction and preparation method and application thereof | |
| CN114797929A (en) | Porous nitrogen modified carbon material loaded cobalt-based catalyst and preparation and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |