CN111747831A - Method for preparing cyclopentanone - Google Patents
Method for preparing cyclopentanone Download PDFInfo
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- CN111747831A CN111747831A CN202010690023.5A CN202010690023A CN111747831A CN 111747831 A CN111747831 A CN 111747831A CN 202010690023 A CN202010690023 A CN 202010690023A CN 111747831 A CN111747831 A CN 111747831A
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- cyclopentanone
- catalyst
- cyclopentene
- organic solvent
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 24
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims abstract description 62
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 238000005406 washing Methods 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000012074 organic phase Substances 0.000 claims abstract description 18
- 239000013177 MIL-101 Substances 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 239000007800 oxidant agent Substances 0.000 claims abstract description 8
- 230000001590 oxidative effect Effects 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000005265 energy consumption Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012621 metal-organic framework Substances 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- KRNSYSYRLQDHDK-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridine Chemical compound C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- JTHVYOIHZNYRCC-UHFFFAOYSA-N 2-hexylcyclopentan-1-one Chemical compound CCCCCCC1CCCC1=O JTHVYOIHZNYRCC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 description 1
- -1 albendanone Chemical compound 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 1
- 229960002495 buspirone Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C45/33—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 CHx-moieties
- C07C45/34—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 CHx-moieties in unsaturated compounds
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0213—Complexes without C-metal linkages
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention provides a method for preparing cyclopentanone, which comprises the steps of mixing cyclopentene and an organic solvent, stirring uniformly, adding a catalyst Fe-MIL-101, stirring continuously to disperse the system uniformly, introducing an oxidant into the system, heating the system slowly to reflux for 1-3h, filtering to remove the catalyst after the reaction is finished, obtaining an organic phase, washing the catalyst with a second organic solvent to obtain a washing solution, combining the washing solution and the organic phase, and rectifying to obtain the target product cyclopentanone.
Description
Technical Field
The invention relates to the field of organic synthesis, and particularly relates to a method for preparing cyclopentanone.
Background
Cyclopentanone, colorless transparent oily liquid, special ether and mint-like smell, is insoluble in water, soluble in alcohol and ether
Most organic solvents. The product is an important fine chemical intermediate, and is an important raw material for perfume and pharmaceutical industry. The cyclopentanone can be used for preparing jasmone, methyl dihydrojasmonate, albendanone, 2-n-hexyl cyclopentanone, 2, 3-cyclopentenopyridine, buspirone as anxiolytic and various anti-inflammatory and anti-cancer drugs, and can also be used for synthesizing pesticides, herbicides and rubber. Meanwhile, cyclopentanone is widely used as a solvent in the electronic industry because of its good solubility for various resins.
At present, the methods for preparing cyclopentanone mainly comprise the following methods:
(1) the adipic acid method mainly uses adipic acid as a raw material to prepare cyclopentanone through high-temperature decarboxylation, which is the main method for industrially producing cyclopentanone at present, but is limited by the source of the raw material and a large amount of pollutants, so that the further development of the process is limited.
(2) The preparation of cyclopentanone by using cyclopentene as a raw material, obtaining cyclopentanol through indirect hydration or direct hydration, and then preparing cyclopentanone through catalytic dehydrogenation generally comprises the steps of hydration reaction of cyclopentene, recovery of unreacted raw materials, refining of a solvent, refining of cyclopentanol, dehydrogenation and refining of cyclopentanol and the like, but has the problems of long flow path and high energy consumption.
(3) The conversion rate is not high, chlorine-containing by-products are generated, the equipment is corroded greatly, and the post-treatment is difficult.
(4) Using cyclopentene as raw material and N2O is used as an oxidant to prepare cyclopentanone, and although the yield of cyclopentanone is high, the reaction energy consumption is very high due to the adoption of conditions such as high temperature and high pressure, and the industrial development is not facilitated.
Metal Organic Frameworks (MOFs) are a class of porous materials constructed by coordination bonds between Metal ions and Organic ligands. The highly dispersed metal ions in the MOFs structure have unsaturated coordination sites, the ions with the unsaturated coordination sites can be used as catalytic active centers to participate in catalytic reaction, and meanwhile, the material has larger specific surface area and pore volume, so that the rapid reaction is facilitated.
The Fe-MIL-101 has a multi-stage mesoporous structure and a special appearance, and has a large specific surface area, so that the Fe-MIL-101 is widely applied to the fields of degradation of dyes, impurity adsorption, catalysis and the like in recent years, but the prior art does not report that the Fe-MIL-101 can be used for catalyzing cyclopentene to prepare cyclopentanone.
Disclosure of Invention
Based on solving the problems of high pollution, strong corrosion, long process, low yield, high energy consumption and the like in the process of preparing cyclopentanone in the prior art, the invention provides a method for preparing cyclopentanone, which comprises the following steps:
the method for preparing cyclopentanone is characterized in that cyclopentanone is obtained by taking cyclopentene as a raw material and Fe-MIL-101 as a catalyst in a first organic solvent and under the condition of an oxidant.
The method comprises the following operation steps of mixing and stirring cyclopentene and an organic solvent uniformly, adding a catalyst Fe-MIL-101, continuing stirring to disperse the system uniformly, introducing an oxidant into the system, and slowly heating the system to reflux for 1-3 hours to obtain cyclopentanone.
The first organic solvent is one or a mixture of ethanol, ethyl acetate, benzene, toluene, dichloromethane and tetrahydrofuran.
The oxidant is selected from oxygen or air.
The mol ratio of the cyclopentene to the catalyst is 1: 0.01-0.1.
Preferably, the method further comprises a post-treatment process, after the reaction is finished, the catalyst is filtered to remove to obtain an organic phase, the catalyst is washed by a second organic solvent to obtain a washing liquid, and the washing liquid and the organic phase are combined and rectified to obtain the target product.
The second organic solvent is one or a mixture of ethanol, ethyl acetate, benzene, toluene, dichloromethane and tetrahydrofuran.
Compared with the prior art, the invention has the following technical effects:
the Fe-MIL-101 is used as the catalyst to catalyze the cyclopentene to prepare the cyclopentanone, the used catalyst is less in dosage, and the method has the advantages of short reaction time, low energy consumption, simple post-treatment, high conversion rate of the cyclopentene, high selectivity of the cyclopentanone and the like.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present disclosure more apparent, the technical solutions of the embodiments of the present disclosure are described below clearly and completely. It is to be understood that the described embodiments are only a few embodiments of the present disclosure, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the described embodiments of the disclosure without any inventive step, are within the scope of protection of the disclosure.
Unless otherwise defined, technical or scientific terms used herein shall have the ordinary meaning as understood by one of ordinary skill in the art to which this disclosure belongs. The use of "first," "second," and similar terms in this disclosure is not intended to indicate any order, quantity, or importance, but rather is used to distinguish one element from another.
Example 1
Preparation of catalyst Fe-MIL-101
0.1mol of terephthalic acid and 0.11mol of FeCl3·6H2Dissolving O in 100mLDMF, adding 10mL of acetic acid, uniformly dispersing, preserving heat for 24h at 110 ℃, cooling to room temperature after the reaction is finished, performing suction filtration by using a suction filtration vacuum pump, repeatedly washing the obtained solid product by using DMF until the color is not changed, recrystallizing by using ethanol, and drying to obtain the solid catalyst Fe-MIL-101.
Example 2
Adding 0.1mol of cyclopentene and 20ml of ethanol into a reaction vessel in sequence, fully mixing the cyclopentene and the ethanol by using a magnetic stirrer, adding 0.001mol of Fe-MIL-101, stirring until the mixture is uniformly dispersed, introducing oxygen into the system, slowly heating the system to reflux, reacting for 1h, filtering to remove a catalyst to obtain an organic phase, washing the catalyst with ethanol for 3 times to obtain a washing solution, combining the washing solution and the organic phase, and rectifying to obtain a target product, wherein the conversion rate of the cyclopentene is 95.5%, and the selectivity of cyclopentanone is 98.1%.
Example 3
Adding 0.1mol of cyclopentene and 20ml of ethyl acetate into a reaction vessel in sequence, fully mixing the cyclopentene and the ethyl acetate by using a magnetic stirrer, adding 0.005mol of Fe-MIL-101, stirring until the mixture is uniformly dispersed, introducing oxygen into the system, slowly heating the system to reflux, reacting for 1.5h, filtering to remove the catalyst to obtain an organic phase, washing the catalyst for 3 times by using ethyl acetate to obtain a washing solution, combining the washing solution with the organic phase, and rectifying to obtain a target product, wherein the conversion rate of the cyclopentene is 97.1%, and the selectivity of cyclopentanone is 98.8%.
Example 4
Adding 0.1mol of cyclopentene and 20ml of benzene into a reaction container in sequence, fully mixing the cyclopentene and the benzene by using a magnetic stirrer, adding 0.002mol of Fe-MIL-101, stirring until the mixture is uniformly dispersed, introducing oxygen into the system, slowly heating the system to reflux, reacting for 1.5h, filtering to remove the catalyst to obtain an organic phase, washing the catalyst with ethanol for 3 times to obtain a washing solution, combining the washing solution and the organic phase, and rectifying to obtain a target product, wherein the conversion rate of the cyclopentene is 96.8%, and the selectivity of cyclopentanone is 99.1%.
Example 5
Adding 0.1mol of cyclopentene and 20ml of toluene into a reaction container in sequence, fully mixing the cyclopentene and the toluene by using a magnetic stirrer, adding 0.01mol of Fe-MIL-101, stirring until the mixture is uniformly dispersed, introducing air into the system, slowly heating the system to reflux, reacting for 2 hours, filtering to remove a catalyst to obtain an organic phase, washing the catalyst with ethanol for 3 times to obtain a washing solution, combining the washing solution and the organic phase, and rectifying to obtain a target product, wherein the conversion rate of the cyclopentene is 98.4%, and the selectivity of cyclopentanone is 99.2%.
Example 6
Adding 0.1mol of cyclopentene and 20ml of dichloromethane into a reaction container in sequence, fully mixing the cyclopentene and the dichloromethane by using a magnetic stirrer, adding 0.001mol of Fe-MIL-101, stirring until the mixture is uniformly dispersed, introducing air into the system, slowly heating the system to reflux, reacting for 3 hours, filtering to remove a catalyst to obtain an organic phase, washing the catalyst with dichloromethane for 3 times to obtain a washing solution, combining the washing solution with the organic phase, and rectifying to obtain a target product, wherein the conversion rate of the cyclopentene is 97.7%, and the selectivity of cyclopentanone is 98.2%.
Example 7
Adding 0.1mol of cyclopentene and 20ml of THF into a reaction vessel in sequence, fully mixing the cyclopentene and 20ml of THF by using a magnetic stirrer, adding 0.003mol of Fe-MIL-101, stirring until the mixture is uniformly dispersed, introducing air into the system, slowly heating the system to reflux, reacting for 2.5 hours, filtering to remove the catalyst to obtain an organic phase, washing the catalyst with ethanol for 3 times to obtain a washing solution, combining the washing solution and the organic phase, and rectifying to obtain a target product, wherein the conversion rate of the cyclopentene is 96.9%, and the selectivity of cyclopentanone is 98.9%.
Finally, it should be noted that: it should be understood that the above examples are only for clearly illustrating the present invention and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the scope of the invention.
Claims (7)
1. The method for preparing cyclopentanone is characterized in that cyclopentanone is obtained by taking cyclopentene as a raw material and Fe-MIL-101 as a catalyst in a first organic solvent and under the condition of an oxidant.
2. The method for preparing cyclopentanone according to claim 1, which comprises the steps of mixing cyclopentene and organic solvent, stirring, adding Fe-MIL-101 as catalyst, stirring to disperse the system, introducing oxidant into the system, and slowly heating to reflux for 1-3h to obtain cyclopentanone.
3. The method for preparing cyclopentanone according to claim 1 or 2, wherein the first organic solvent is selected from one or more of ethanol, ethyl acetate, benzene, toluene, dichloromethane, and tetrahydrofuran.
4. Process for the preparation of cyclopentanone according to claim 1 or 2, wherein the oxidizing agent is selected from oxygen or air.
5. The process for preparing cyclopentanone according to claim 1 or 2, wherein the molar ratio of cyclopentene to catalyst is 1: 0.01-0.1.
6. The method for preparing cyclopentanone according to claim 1 or 2, further comprising a post-treatment process, wherein after the reaction, the catalyst is filtered to obtain an organic phase, the catalyst is washed with a second organic solvent to obtain a washing solution, and the washing solution is combined with the organic phase and rectified to obtain the target product.
7. The method for preparing cyclopentanone according to claim 6, wherein the second organic solvent is selected from one or more of ethanol, ethyl acetate, benzene, toluene, dichloromethane, and tetrahydrofuran.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112321399A (en) * | 2020-12-01 | 2021-02-05 | 山东卓俊实业有限公司 | Preparation method of chemical intermediate |
| CN112479838A (en) * | 2020-12-02 | 2021-03-12 | 山东卓俊实业有限公司 | Application of imidazole carbonate in preparation of chemical intermediates |
-
2020
- 2020-07-17 CN CN202010690023.5A patent/CN111747831B/en active Active
Non-Patent Citations (2)
| Title |
|---|
| IGOR Y.SKOBELEV ET AL: ""Solvent-free allyic oxidation of alkenes with O2 mediated by Fe- and Cr-MIL-101"", 《JOURNAL OF CATALYSIS》 * |
| ZHAOKUI JIN ET AL: ""Imparting magnetic functionality to iron-based MIL-101 via facile Fe3O4 nanoparticle encapsulation: an efficient and recoverable catalyst for aerobic oxidation"", 《RSC ADV》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112321399A (en) * | 2020-12-01 | 2021-02-05 | 山东卓俊实业有限公司 | Preparation method of chemical intermediate |
| CN112479838A (en) * | 2020-12-02 | 2021-03-12 | 山东卓俊实业有限公司 | Application of imidazole carbonate in preparation of chemical intermediates |
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| CN111747831B (en) | 2022-07-05 |
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