CN114308007B - Method for preparing solid acid catalyst for preparing dodecanedioic acid dimethyl ester - Google Patents
Method for preparing solid acid catalyst for preparing dodecanedioic acid dimethyl ester Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 66
- 239000011973 solid acid Substances 0.000 title claims abstract description 38
- IZMOTZDBVPMOFE-UHFFFAOYSA-N dimethyl dodecanedioate Chemical compound COC(=O)CCCCCCCCCCC(=O)OC IZMOTZDBVPMOFE-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 239000002243 precursor Substances 0.000 claims abstract description 23
- 239000003610 charcoal Substances 0.000 claims abstract description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002245 particle Substances 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 238000001354 calcination Methods 0.000 claims abstract description 10
- 239000008367 deionised water Substances 0.000 claims abstract description 10
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 10
- 238000002791 soaking Methods 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims description 30
- 238000001035 drying Methods 0.000 claims description 27
- 239000011230 binding agent Substances 0.000 claims description 10
- 238000000967 suction filtration Methods 0.000 claims description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 229920000180 alkyd Polymers 0.000 claims description 2
- 239000012018 catalyst precursor Substances 0.000 claims description 2
- 238000013329 compounding Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000003738 black carbon Substances 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 238000000643 oven drying Methods 0.000 abstract 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparation method of a solid acid catalyst for preparing dimethyl dodecanedioate, and belongs to the field of catalysts. When the catalyst is prepared, charcoal particles with the mass fraction of 20-40% and SnCl with the mass fraction of 10-30% are weighed 4 ·5H 2 Adding O and 30-70% diatomite into a certain deionized water, and neutralizing, stirring and extruding to obtain a precursor; h of precursor at 1-5 mol/L 2 SO 4 Soaking in the solution, oven drying, and adding into N 2 Calcining at 400-650 ℃ under the protection of the catalyst to obtain the solid acid catalyst. The catalyst has higher conversion rate and selectivity when being applied to the preparation of the dimethyl dodecanedioate, and can be recycled.
Description
Technical Field
The invention relates to a preparation method of a solid acid catalyst for preparing dimethyl dodecanedioate, and belongs to the technical field of catalysts.
Background
Dimethyl dodecanedioate is used as an important fine chemical product and is widely applied to the industries of medicines, plastics, polyurethane and paint.
The existing synthesis methods mainly comprise a biological fermentation method and a cyclohexanone oxidation method.
The fermentation method has the problems of long process time and more impurities, and can not be popularized in the fields of spice, medicine and the like.
The cyclohexanone oxidation method has problems of high cost and low yield because a large amount of hydrogen peroxide is consumed as an oxidant.
CN1670010a discloses a method for preparing dimethyl dodecanedioate by oxidation of cyclohexanone, which adopts methanol as a solvent, cyclohexanone as a raw material, prepares peroxide of cyclohexanone by using quaternary ammonium salt, crown ether and other transfer catalysts and hydrogen peroxide as an oxidant, and obtains dimethyl dodecanedioate by ring-opening dimerization. The hydrogen peroxide consumption is 45% -60% of cyclohexanone, and the final yield is about 72%.
The dodecanedioic acid is used as a raw material, and the acid catalyst and the methanol directly perform esterification reaction, so that the reaction steps are reduced, the reaction selectivity is higher, and the method is a feasible scheme for preparing the dimethyl dodecanedioate.
The traditional homogeneous acid catalyst has the problems of difficult separation and easy corrosion to equipment, so that the application of the catalyst in the chemical industry field is limited.
Heterogeneous solid acid catalysts gradually become a hot spot for research in the field of catalysts by virtue of the characteristics of strong acidity, easiness in separation, no corrosion to equipment and reusability.
Carbonaceous solid acid catalysts were originally proposed by Japanese scholars Masakazu Toda, atsushi Takagaki et al. The biomass solid acid catalyst is obtained by taking cellulose as a raw material and performing carbonization and sulfonation, and has higher acidity and lower cost. However, the carbonized sulfonated solid acid catalyst still has the problems of easy pulverization and lower mechanical strength when in use, and limits the large-scale application of the carbonized sulfonated solid acid catalyst.
Disclosure of Invention
The invention aims to provide a preparation method of a composite solid acid catalyst, which takes cheap and easily obtained charcoal particles as active site carriers and composites SnO 2 And the diatomite is used for preparing the solid acid catalyst with excellent catalytic performance, high mechanical strength and low cost. When used for preparing the dimethyl dodecanedioate, the catalyst has higher conversion rate and can be reused.
The main technical proposal of the invention is that the preparation method of the solid acid catalyst for preparing the dimethyl dodecanedioate is characterized in that charcoal particles are taken as active site carriers and pass through SnO 2 And (3) preparing the catalyst by compounding diatomite.
In general, the preparation method of the invention comprises the following steps:
(1) Weighing 20-40% of charcoal particles and 10-30% of SnCl by mass fraction 4 ·5H 2 Adding O and 30-70% diatomite into a certain deionized water, and stirring to obtain a stable suspension;
(2) Dropwise adding concentrated ammonia water, adjusting the pH value of the suspension to 6, performing suction filtration and drying, adding 5-10% of binder into the product, uniformly mixing, extruding strips and drying to obtain a catalyst precursor;
(3) Weighing a certain amount of precursor, wherein the precursor is H of 1-5 mol/L 2 SO 4 The precursor is soaked in the solution for acidic activation, and the precursor is dried at 80-130 ℃ after being soaked;
(4) Placing the activated sample in N 2 Calcining at 400-650 ℃ under protection to finally obtain the composite solid acid catalyst.
The invention relates to a preparation method of a solid acid catalyst for preparing dodecanedioic acid dimethyl ester, which is characterized in that charcoal particles can be obtained by crushing one of white charcoal, black charcoal, active carbon and machine-made charcoal.
The preparation method of the solid acid catalyst for preparing the dimethyl dodecanedioate is characterized in that the mesh number of the diatomite is 80-200 mesh.
The preparation method of the solid acid catalyst for preparing the dimethyl dodecanedioate is characterized in that the addition amount of the binder is 5-10%.
The preparation method of the solid acid catalyst for preparing the dimethyl dodecanedioate is characterized in that the drying temperature is 80-130 ℃.
The invention relates to a preparation method of a solid acid catalyst for preparing dodecanedioic acid dimethyl ester, which is characterized by comprising the following steps of 2 SO 4 The soaking time of the solution is 3-24 hours.
The solid acid catalyst prepared by the preparation method is used for preparing the dimethyl dodecanedioate by reacting dodecanedioic acid with methanol.
The reaction materials are dodecanedioic acid and methanol, the ratio of the amounts of alkyd substances is 1-20, the reaction temperature is 60-120 ℃, the conversion rate of the dodecanedioic acid is 71-88%, and the selectivity of the dodecanedioic acid dimethyl ester is 84-93%.
Effects of the invention
The traditional homogeneous catalyst has the defects of easy corrosion equipment and difficult separation, the solid acid catalyst prepared by the method of the invention is prepared by taking low-cost and easily available diatomite and carbon-based particles as carriers through chemical doping and modification, and the solid acid catalyst has strong catalytic activity and high selectivity and can be reused.
Detailed Description
The invention will be described in detail with reference to the following examples
Example 1
20g of charcoal particles and 10g of SnCl 4 ·5H 2 Adding O and 70g of diatomite into 250g of deionized water, stirring for 2 hours, dropwise adding concentrated ammonia water to adjust the pH to 6, filtering, drying, adding 10% of binder, extruding, and drying to obtain a precursor. Soaking the precursor in 1mol/L H 2 SO 4 Drying the solution for 12h, and then adding the product into N 2 Calcining for 6 hours at 450 ℃ under protection to obtain the final solid acid catalyst. 16g of dodecanedioic acid and 27g of methanol are weighed, a certain proportion of catalyst is added, the mixture is reacted for a certain time on a reflux reaction device, and the reaction result is detected by gas chromatography after suction filtration and is as follows:
| (catalyst/acid)/(percent) | Reaction temperature/. Degree.C | Conversion/% | Selectivity/% |
| 2 | 60 | 71 | 91 |
| 4 | 80 | 82 | 87 |
| 10 | 100 | 83 | 85 |
Example 2
20g of charcoal particles and 10g of SnCl 4 ·5H 2 Adding O and 70g of diatomite into 250g of deionized water, stirring for 2 hours, dropwise adding concentrated ammonia water to adjust the pH to 6, filtering, drying, adding 10% of binder, extruding, and drying to obtain a precursor. Soaking the precursor in 2mol/L H 2 SO 4 Drying the solution for 12h, and then adding the product into N 2 Calcining for 6 hours at 450 ℃ under protection to obtain the final solid acid catalyst. 16g of dodecanedioic acid and 27g of methanol are weighed, a certain proportion of catalyst is added, the mixture is reacted for a certain time on a reflux reaction device, and the reaction result is detected by gas chromatography after suction filtration and is as follows:
| (catalyst/acid)/(percent) | Reaction temperature/. Degree.C | Conversion/% | Selectivity/% |
| 2 | 60 | 73 | 91 |
| 4 | 80 | 83 | 88 |
| 10 | 100 | 83 | 84 |
Example 3
20g of charcoal particles and 10g of SnCl 4 ·5H 2 Adding O and 70g of diatomite into 250g of deionized water, stirring for 2 hours, dropwise adding concentrated ammonia water to adjust the pH to 6, filtering, drying, adding 10% of binder, extruding, and drying to obtain a precursor. Soaking the precursor in 3mol/L H 2 SO 4 Drying the solution for 12h, and then adding the product into N 2 Calcining for 6 hours at 450 ℃ under protection to obtain the final solid acid catalyst. 16g of dodecanedioic acid and 27g of methanol are weighed, a certain proportion of catalyst is added, the mixture is reacted for a certain time on a reflux reaction device, and the reaction result is detected by gas chromatography after suction filtration and is as follows:
| (catalyst/acid)/(percent) | Reaction temperature/. Degree.C | Conversion/% | Selectivity/% |
| 2 | 60 | 78 | 92 |
| 4 | 80 | 85 | 92 |
| 10 | 100 | 86 | 84 |
Example 4
20g of charcoal particles and 10g of SnCl 4 ·5H 2 Adding O and 70g of diatomite into 250g of deionized water, stirring for 2 hours, dropwise adding concentrated ammonia water to adjust the pH to 6, filtering, drying, adding 10% of binder, extruding, and drying to obtain a precursor. Soaking the precursor in 4mol/L H 2 SO 4 Drying the solution for 12h, and then adding the product into N 2 Calcining for 6 hours at 450 ℃ under protection to obtain the final solid acid catalyst. 16g of dodecanedioic acid and 27g of methanol are weighed, a certain proportion of catalyst is added, the mixture is reacted for a certain time on a reflux reaction device, and the reaction result is detected by gas chromatography after suction filtration and is as follows:
| (catalyst/acid)/(percent) | Reaction temperature/. Degree.C | Conversion/% | Selectivity/% |
| 2 | 60 | 81 | 93 |
| 4 | 80 | 87 | 92 |
| 10 | 100 | 88 | 90 |
Example 5
20g of charcoal particles and 10g of SnCl 4 ·5H 2 Adding O and 70g of diatomite into 250g of deionized water, stirring for 2 hours, dropwise adding concentrated ammonia water to adjust the pH to 6, filtering, drying, adding 10% of binder, extruding, and drying to obtain a precursor. Soaking the precursor in 5mol/L H 2 SO 4 Drying the solution for 12h, and then adding the product into N 2 Calcining for 6 hours at 450 ℃ under protection to obtain the final solid acid catalyst. 16g of dodecanedioic acid and 27g of methanol are weighed, a certain proportion of catalyst is added, the mixture is reacted for a certain time on a reflux reaction device, and the reaction result is detected by gas chromatography after suction filtration and is as follows:
| (catalyst/acid)/(percent) | Reaction temperature/. Degree.C | Conversion/% | Selectivity/% |
| 2 | 60 | 81 | 93 |
| 4 | 80 | 88 | 93 |
| 10 | 100 | 88 | 91 |
Example 6
20g of charcoal particles and 10g of SnCl 4 ·5H 2 Adding O and 70g of diatomite into 250g of deionized water, stirring for 2 hours, dropwise adding concentrated ammonia water to adjust the pH to 6, filtering, drying, adding 10% of binder, extruding, and drying to obtain a precursor. Soaking the precursor in 5mol/L H 2 SO 4 Drying the solution for 12h, and then adding the product into N 2 Calcining for 6 hours at 550 ℃ under protection to obtain the final solid acid catalyst. 16g of dodecanedioic acid and 27g of methanol are weighed, a certain proportion of catalyst is added, the mixture is reacted for a certain time on a reflux reaction device, and the reaction result is detected by gas chromatography after suction filtration and is as follows:
| (catalyst/acid)/(percent) | Reaction temperature/. Degree.C | Conversion/% | Selectivity/% |
| 2 | 60 | 80 | 92 |
| 4 | 80 | 86 | 91 |
| 10 | 100 | 84 | 89 |
Example 7
20g of charcoal particles and 10g of SnCl 4 ·5H 2 Adding O and 70g of diatomite into 250g of deionized water, stirring for 2 hours, dropwise adding concentrated ammonia water to adjust the pH to 6, filtering, drying, adding 10% of binder, extruding, and drying to obtain a precursor. Soaking the precursor in 5mol/L H 2 SO 4 Drying the solution for 12h, and then adding the product into N 2 Calcining for 6 hours at 450 ℃ under protection to obtain the final solid acid catalyst. 16g of dodecanedioic acid and 27g of methanol are weighed, 4% of catalyst is added, the mixture is reacted for a certain time on a reflux reaction device, and the reaction result is detected by gas chromatography after suction filtration and is as follows:
| number of catalyst uses | Reaction temperature/. Degree.C | Conversion/% | Selectivity/% |
| 1 | 80 | 86 | 91 |
| 2 | 80 | 85 | 90 |
| 3 | 80 | 82 | 90 |
| 4 | 80 | 82 | 89 |
| 5 | 80 | 81 | 89 |
Comparative example 1
16g of dodecanedioic acid and 27g of methanol are weighed, a commercial amberlyst15 solid acid catalyst is added, the mixture is reacted for a certain time on a reflux reaction device, and the reaction result is detected by gas chromatography after suction filtration and is as follows:
| (catalyst/acid)/(percent) | Reaction temperature/. Degree.C | Conversion/% | Selectivity/% |
| 2 | 60 | 67 | 85 |
| 4 | 80 | 71 | 82 |
| 10 | 100 | 73 | 82 |
. From the above examples and comparative examples, the solid acid catalyst prepared by the invention has high conversion rate, good selectivity and certain commercial application prospect when catalyzing and synthesizing dimethyl dodecanedioate.
Claims (7)
1. A process for preparing the solid acid catalyst of dimethyl dodecanedioate features that the charcoal particles are used as active site carrier and SnO is used as catalyst 2 Preparing a catalyst by compounding diatomite; said preparation of dimethyl dodecanedioateThe preparation method of the solid acid catalyst comprises the following steps:
(1) Charcoal particles with mass fraction of 20-40% and SnCl with mass fraction of 10-30% 4 ·5H 2 Adding O and 30-70% diatomite into deionized water, and stirring to obtain a stable suspension;
(2) Dropwise adding concentrated ammonia water, adjusting the pH value of the suspension to 6, performing suction filtration and drying, adding a binder into the product, uniformly mixing, extruding and drying to obtain a catalyst precursor;
(3) Taking a precursor, wherein the precursor is H of 1-5 mol/L 2 SO 4 The precursor is soaked in the solution for acidic activation, and is dried after being soaked;
(4) The treated product is placed in N 2 Calcining at 400-650 ℃ under protection to finally obtain the composite solid acid catalyst;
the charcoal particles are obtained by crushing one of white carbon, black carbon, active carbon and machine-made carbon.
2. The method for preparing a solid acid catalyst for preparing dimethyl dodecanedioate according to claim 1, wherein the mesh number of the diatomite is 80-200 mesh.
3. The method for preparing the solid acid catalyst for preparing the dimethyl dodecanedioate according to claim 1, which is characterized in that the drying temperature is 80-130 ℃.
4. The method for preparing a solid acid catalyst for preparing dimethyl dodecanedioate according to claim 1, characterized in that H 2 SO 4 The soaking time of the solution is 3-24 hours.
5. The use of the solid acid catalyst prepared by the preparation method according to claim 1, which is characterized in that the catalyst is used for preparing dimethyl dodecanedioate by reacting dodecanedioic acid with methanol.
6. The method according to claim 5, wherein the reaction mixture is dodecanedioic acid and methanol, the ratio of the amounts of alkyd substances is 1-20, and the reaction temperature is 60-120 ℃.
7. The method according to claim 5, wherein the conversion of dodecanedioic acid is 71-88% and the selectivity of dimethyl dodecanedioate is 84-93%.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932306A (en) * | 1973-01-17 | 1976-01-13 | Imi (Tami) Institute For Research & Development | Solid catalyst for heterogeneous reactions |
| CN1613559A (en) * | 2004-09-28 | 2005-05-11 | 北京化工大学 | Preparation for hydrophobic solid acid catalyst |
| CN104028294A (en) * | 2014-06-26 | 2014-09-10 | 江南大学 | Solid acid catalyst suitable for microwave-assisted reaction and preparation method of solid acid catalyst |
| CN106732673A (en) * | 2016-11-10 | 2017-05-31 | 常州大学 | A kind of construction method of the solid acid catalyst with montmorillonite as carrier |
-
2020
- 2020-10-09 CN CN202011070649.2A patent/CN114308007B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932306A (en) * | 1973-01-17 | 1976-01-13 | Imi (Tami) Institute For Research & Development | Solid catalyst for heterogeneous reactions |
| CN1613559A (en) * | 2004-09-28 | 2005-05-11 | 北京化工大学 | Preparation for hydrophobic solid acid catalyst |
| CN104028294A (en) * | 2014-06-26 | 2014-09-10 | 江南大学 | Solid acid catalyst suitable for microwave-assisted reaction and preparation method of solid acid catalyst |
| CN106732673A (en) * | 2016-11-10 | 2017-05-31 | 常州大学 | A kind of construction method of the solid acid catalyst with montmorillonite as carrier |
Non-Patent Citations (1)
| Title |
|---|
| 陈丹云 ; 邹雪艳 ; 何建英.SO42-/SnO2-硅藻土型固体酸的制备及其对正丁酸与异戊醇的催化酯化.《应用化学》.2010,第27卷(第7期),第797-800页. * |
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