CN111116342B - Method for preparing hexafluoroacetone through isomerization of hexafluoropropylene oxide - Google Patents
Method for preparing hexafluoroacetone through isomerization of hexafluoropropylene oxide Download PDFInfo
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- CN111116342B CN111116342B CN201911318644.4A CN201911318644A CN111116342B CN 111116342 B CN111116342 B CN 111116342B CN 201911318644 A CN201911318644 A CN 201911318644A CN 111116342 B CN111116342 B CN 111116342B
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- reaction
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- hexafluoroacetone
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- hexafluoropropylene oxide
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- 238000000034 method Methods 0.000 title claims abstract description 20
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 title claims abstract description 18
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000006317 isomerization reaction Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 239000002994 raw material Substances 0.000 claims abstract description 8
- HEBNOKIGWWEWCN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;hydrate Chemical compound O.FC(F)(F)C(=O)C(F)(F)F HEBNOKIGWWEWCN-UHFFFAOYSA-N 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002808 molecular sieve Substances 0.000 claims description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052593 corundum Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910001845 yogo sapphire Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- YEDDVXZFXSHDIB-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoropropan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)F YEDDVXZFXSHDIB-UHFFFAOYSA-N 0.000 description 1
- BKWAVXQSZLEURV-UHFFFAOYSA-N 2-chloro-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(Cl)C(F)(F)F BKWAVXQSZLEURV-UHFFFAOYSA-N 0.000 description 1
- -1 Al2O3 Chemical class 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical group FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the field of fluoride preparation, and particularly relates to a method for preparing hexafluoroacetone through hexafluoropropylene oxide isomerization. The method specifically comprises the following steps: filling a catalyst into a reactor, and introducing reaction raw material gas hexafluoropropylene oxide for reaction, wherein the reaction pressure is normal pressure, the reaction temperature is 0-200 ℃, and the reaction space velocity is 100-‑1And introducing the product into ionized water after the reaction is finished, thus obtaining hexafluoroacetone hydrate. According to the method of the present invention, high purity hexafluoroacetone can be obtained by isomerizing hexafluoropropylene oxide, by-products are hardly formed, selectivity is high, the reaction can be carried out at low temperature and normal pressure, and requirements on reaction conditions are low. Meanwhile, the catalyst used in the invention is simple to prepare, the raw materials are easy to obtain, and the catalyst is easy to form and produce in a large scale.
Description
Technical Field
The invention belongs to the field of fluoride preparation, and particularly relates to a method for preparing hexafluoroacetone through hexafluoropropylene oxide isomerization.
Background
Hexafluoroacetone (CF3COCF3, HFA for short) is a fluorine-containing fine chemical which has a wide range of uses. First reported in the literature, trials were successful in 1957 in the 60's of the 20 th century by Allied Chemical and Du Pont, USA. Due to the strong electron withdrawing property of 2-CF 3 groups, the physical and chemical properties of HFA are greatly different from those of acetone, and the HFA also has unique physical and chemical properties. Hexafluoroacetone is used in the fields of medicines, agricultural chemicals, synthetic materials and the like, and particularly can be used as a raw material for synthesizing high molecular materials in special fields, wherein hexafluoroacetone is used as a raw material of a high-grade solvent, namely hexafluoropropanol, and a monomer of a high-performance fluorine-containing elastomer in a large industrial application.
The preparation technology of hexafluoroacetone mainly comprises an octafluoroisobutylene oxidation method, a hexafluoropropylene oxide rearrangement method, a hexafluoropropylene catalytic oxidation method, a hexachloroacetone high-temperature gas phase catalytic fluorination method and a 2-chlorohexafluoropropane oxidation method. In the prior art, hexafluoropropylene oxide is used as a raw material, hexafluoroacetone is generated through molecular rearrangement isomerization, and solid Lewis acid such as Al2O3, Cr2O3, AlCl3 and the like can be used as a catalyst of the reaction, which is also a main industrial method for producing HFA at present. US patent 4238416 uses fluorinated Al2O3 or Al2O3-SiO2 as catalyst, which has high HFPO conversion rate, but the exothermic reaction is severe, and needs to introduce inert gas and oxygen, which has high requirements for temperature and pressure. Japanese patents JP58062130 and JP58062131 have examined a series of fluorinated Al2O3, Cr2O3, Al2O3-SiO2 catalysts, but with a high number of reaction by-products. U.S. patent US2004186322, which uses TiO2 as a catalyst and US6933413, which uses SnO2 as a catalyst, achieves higher yields but still requires higher reaction temperatures. The catalyst reported in the Chinese patent CN1899692A can be composed of Cr2O3, AlF3, TiO2, graphite or metal powder, and can react at normal temperature and normal pressure, but the catalyst has more components and is complex to prepare.
Therefore, a catalyst which has high activity, high stability and simple preparation at low temperature and normal pressure is needed to be suitable for preparing hexafluoroacetone by the catalytic isomerization of hexafluoropropylene oxide.
Disclosure of Invention
The invention aims to provide a method for preparing hexafluoroacetone by isomerizing hexafluoropropylene oxide.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing hexafluoroacetone by isomerizing hexafluoropropylene oxide adopts the following reaction formula (I):
the method specifically comprises the following steps: filling a catalyst into a reactor, and introducing reaction raw material gas hexafluoropropylene oxide for reaction, wherein the reaction pressure is normal pressure, the reaction temperature is 0-200 ℃, and the reaction space velocity is 100--1And introducing the product into ionized water after the reaction is finished, thus obtaining hexafluoroacetone hydrate.
Preferably, the reaction temperature is 20-100 ℃, and the reaction space velocity is 150--1。
Preferably, the reaction space velocity is 300h-1。
Wherein, the catalyst is prepared by the following method: silicon is mixedZSM-5 molecular sieve with aluminum ratio of 50 is dried in a baking oven at 120 ℃ for 4 hours, 10g of the molecular sieve is put into a tube furnace, N2 is introduced, the temperature is raised to 350 ℃, CHClF is introduced2The gas flow is 30ml/min, fluorination is carried out for 4 hours, and N2 is introduced to be cooled to room temperature. Tabletting to 20-40 mesh.
Compared with the prior art, the invention has the beneficial effects that:
according to the method of the present invention, high purity hexafluoroacetone can be obtained by isomerizing hexafluoropropylene oxide, by-products are hardly formed, selectivity is high, the reaction can be carried out at low temperature and normal pressure, and requirements on reaction conditions are low. Meanwhile, the catalyst used in the invention is simple to prepare, the raw materials are easy to obtain, and the catalyst is easy to form and produce in a large scale.
Detailed Description
In order to make the technical solutions of the present invention better understood by those skilled in the art, the present invention will be further described in detail with reference to the following preferred embodiments.
The embodiment is as follows: preparation of the catalyst: drying a ZSM-5 molecular sieve (the silica-alumina ratio is 50) in an oven at 120 ℃ for 4 hours, taking 10g of the molecular sieve, putting the molecular sieve into a tube furnace, introducing N2, heating to 350 ℃, introducing R22 gas at the flow rate of 30ml/min, fluorinating for 4 hours, and introducing N2, and cooling to room temperature. Tabletting to obtain 20-40 mesh powder as catalyst.
And (3) preparing hexafluoroacetone by catalytic isomerization of hexafluoropropylene oxide: the reaction test is carried out in a fixed bed reactor, a stainless steel reaction tube (with the inner diameter of 10mm and the length of 300mm) is filled with 5.0ml (20-40 meshes) of catalyst, the reaction temperature is 20 ℃, 60 ℃, 100 ℃, 150 ℃, 200 ℃, the operation pressure is normal pressure, and the reaction space velocity is 300h < -1 >. And analyzing and measuring the reaction product by adopting a gas chromatography analysis method, and then introducing the reaction product into deionized water to absorb and generate hexafluoroacetone hydrate. The reaction results are shown in table 1.
Wherein, the comparative catalyst is TiO2 prepared by US2004186322 as the catalyst;
TABLE 1
As can be seen from table 1, according to the process of the present invention, high-purity hexafluoroacetone can be obtained by isomerizing hexafluoropropylene oxide, by-products are hardly formed, selectivity is high, the reaction can be carried out at low temperature and normal pressure, and the requirements on reaction conditions are low.
The above description is only a preferred embodiment of the present invention, and for those skilled in the art, the present invention should not be limited by the description of the present invention, which should be interpreted as a limitation.
Claims (1)
1. A method for preparing hexafluoroacetone by isomerizing hexafluoropropylene oxide is characterized by adopting the following reaction formula (I):
the method specifically comprises the following steps: filling a catalyst into a reactor, and introducing reaction raw material gas hexafluoropropylene oxide for reaction, wherein the reaction pressure is normal pressure, the reaction temperature is 60 ℃, and the reaction space velocity is 300h-1Introducing the product into ionized water after the reaction is finished, and obtaining hexafluoroacetone hydrate;
wherein, the catalyst is prepared by the following method: drying a ZSM-5 molecular sieve with a silicon-aluminum ratio of 50 in an oven at 120 ℃ for 4 hours, taking 10g of the molecular sieve, putting the molecular sieve into a tube furnace, introducing N2, heating to 350 ℃, introducing CHClF2 gas with the flow of 30ml/min, fluorinating for 4 hours, and introducing N2, and cooling to room temperature; tabletting to 20-40 mesh.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911318644.4A CN111116342B (en) | 2019-12-19 | 2019-12-19 | Method for preparing hexafluoroacetone through isomerization of hexafluoropropylene oxide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911318644.4A CN111116342B (en) | 2019-12-19 | 2019-12-19 | Method for preparing hexafluoroacetone through isomerization of hexafluoropropylene oxide |
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| Publication Number | Publication Date |
|---|---|
| CN111116342A CN111116342A (en) | 2020-05-08 |
| CN111116342B true CN111116342B (en) | 2022-07-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201911318644.4A Active CN111116342B (en) | 2019-12-19 | 2019-12-19 | Method for preparing hexafluoroacetone through isomerization of hexafluoropropylene oxide |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116532133B (en) * | 2023-03-24 | 2025-05-27 | 湖南有色郴州氟化学有限公司 | Method for preparing hexafluoroacetone by isomerization of hexafluoropropylene oxide |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4238416A (en) * | 1976-08-21 | 1980-12-09 | Daikin Kogyo Co., Ltd. | Method for isomerization of fluorinated epoxy compounds |
| SU859348A2 (en) * | 1979-08-10 | 1981-08-30 | Предприятие П/Я Г-4567 | Method of producing hexafluoroacetone |
| US4705904A (en) * | 1984-02-14 | 1987-11-10 | Allied Corporation | Vapor phase synthesis of hexafluoroisobutylene |
| RU2152923C2 (en) * | 1996-03-14 | 2000-07-20 | АООТ "Кирово-Чепецкий химический комбинат им.Б.П.Константинова" | Method of preparing hexafluoroacetone |
| CN1899692A (en) * | 2006-07-25 | 2007-01-24 | 浙江蓝天环保高科技股份有限公司 | Catalyst for preparing hexafloroacetone by isomerization method and its preparing method and use |
| CN101036882A (en) * | 2007-04-13 | 2007-09-19 | 上海泰卓科技有限公司 | Catalyzer of the Epoxide including fluorin isomerization and the preparing method and application |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE345321T1 (en) * | 2001-07-19 | 2006-12-15 | Daikin Ind Ltd | METHOD FOR PRODUCING HEXAFLUOROCACETONE AND ITS HYDRATE |
-
2019
- 2019-12-19 CN CN201911318644.4A patent/CN111116342B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4238416A (en) * | 1976-08-21 | 1980-12-09 | Daikin Kogyo Co., Ltd. | Method for isomerization of fluorinated epoxy compounds |
| SU859348A2 (en) * | 1979-08-10 | 1981-08-30 | Предприятие П/Я Г-4567 | Method of producing hexafluoroacetone |
| US4705904A (en) * | 1984-02-14 | 1987-11-10 | Allied Corporation | Vapor phase synthesis of hexafluoroisobutylene |
| RU2152923C2 (en) * | 1996-03-14 | 2000-07-20 | АООТ "Кирово-Чепецкий химический комбинат им.Б.П.Константинова" | Method of preparing hexafluoroacetone |
| CN1899692A (en) * | 2006-07-25 | 2007-01-24 | 浙江蓝天环保高科技股份有限公司 | Catalyst for preparing hexafloroacetone by isomerization method and its preparing method and use |
| CN101036882A (en) * | 2007-04-13 | 2007-09-19 | 上海泰卓科技有限公司 | Catalyzer of the Epoxide including fluorin isomerization and the preparing method and application |
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