CN115490651A - Preparation method of epoxy perfluoropentane - Google Patents
Preparation method of epoxy perfluoropentane Download PDFInfo
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- CN115490651A CN115490651A CN202211267335.0A CN202211267335A CN115490651A CN 115490651 A CN115490651 A CN 115490651A CN 202211267335 A CN202211267335 A CN 202211267335A CN 115490651 A CN115490651 A CN 115490651A
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- China
- Prior art keywords
- perfluoro
- epoxy
- methyl
- pentene
- methylpentane
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- 229960004692 perflenapent Drugs 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000004593 Epoxy Substances 0.000 title claims abstract description 5
- NJCBUSHGCBERSK-UHFFFAOYSA-N perfluoropentane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F NJCBUSHGCBERSK-UHFFFAOYSA-N 0.000 title claims abstract description 5
- NOESGFSFSJKFIF-UHFFFAOYSA-N 2-fluoro-2-(1,1,2,2,2-pentafluoroethyl)-3,3-bis(trifluoromethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C1(F)OC1(C(F)(F)F)C(F)(F)F NOESGFSFSJKFIF-UHFFFAOYSA-N 0.000 claims abstract description 18
- FAEGGADNHFKDQX-UHFFFAOYSA-N 1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)pent-2-ene Chemical compound FC(F)(F)C(C(F)(F)F)=C(F)C(F)(F)C(F)(F)F FAEGGADNHFKDQX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000007800 oxidant agent Substances 0.000 claims abstract description 7
- 239000002270 dispersing agent Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 description 5
- SAPOZTRFWJZUFT-UHFFFAOYSA-N 1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)pent-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(C(F)(F)F)C(F)(F)F SAPOZTRFWJZUFT-UHFFFAOYSA-N 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 Perfluoro-2, 3-epoxy-2-methyl cyclopentane epoxide Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WVSNNWIIMPNRDB-UHFFFAOYSA-N 1,1,1,3,3,4,4,5,5,6,6,6-dodecafluorohexan-2-one Chemical compound FC(F)(F)C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F WVSNNWIIMPNRDB-UHFFFAOYSA-N 0.000 description 1
- PBVZTJDHQVIHFR-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)F.FC(F)=C(F)C(F)(F)F PBVZTJDHQVIHFR-UHFFFAOYSA-N 0.000 description 1
- HZTIKNWLZSIYHM-UHFFFAOYSA-N 2,2,3-trifluoro-3-(1,1,2,2,3,3,3-heptafluoropropyl)oxirane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C1(F)OC1(F)F HZTIKNWLZSIYHM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/06—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the liquid phase
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of epoxy perfluoropentane, wherein perfluoro-2-methyl-2-pentene and a dispersing agent react under the action of an oxidizing agent to obtain a product perfluoro-2, 3-epoxy-2-methylpentane. The method has the advantages of high product selectivity, simple process, high efficiency, good quality and environmental protection.
Description
Technical Field
The invention relates to the technical field of fluorine chemical industry, in particular to a preparation method of epoxy perfluoropentane.
Background
Perfluoro-2, 3-epoxy-2-methyl cyclopentane epoxide is an important fluorine-containing chemical and organic synthesis intermediate, can be used as a fire extinguishing agent, a cleaning agent, a solvent and the like for multiple purposes, can be used as an intermediate for synthesizing perfluorohexanone, a fluorine-containing ether solvent and the like, and has wide application potential.
CN 102992986A discloses a method for preparing perfluoro-2, 3-epoxy-2-methylpentane from hexafluoropropylene dimer mixture, perfluoro-4-methyl-2-pentene or perfluoro-2-methyl-2-pentene as raw materials, sodium hypochlorite as an oxidant, and diethylene glycol dimethyl ether as a solvent. However, the usage amount of the sodium hypochlorite aqueous solution in the method is 5 times of that of a reaction substrate, three wastes are high, and the required sodium hypochlorite has high concentration and is unstable and difficult to recover.
Therefore, it is necessary to develop a method for preparing perfluoropentane epoxide with high efficiency, good quality and environmental protection.
Disclosure of Invention
The invention aims to provide a preparation method of perfluoro-2, 3-epoxy-2-methylpentane aiming at the defects of the prior art.
A process for preparing perfluoro-epoxy-pentane includes reaction between perfluoro-2-methyl-2-pentene and disperser under action of oxidant to obtain perfluoro-2, 3-epoxy-2-methylpentane.
Preferably, the reaction temperature is 15 to 80 ℃.
Preferably, the reaction pressure is 0 to 0.6MPa.
Preferably, the oxidizing agent is at least one selected from the group consisting of an aqueous solution of h2o2 at a volume concentration of 30%, a sodium hypochlorite solution at a volume concentration of 8% to 15%, and oxygen at a volume concentration of 30% to 40%.
Preferably, the dispersant is selected from one or more of methyl ether, ethanol and acetonitrile.
Preferably, the conversion of perfluoro-2-methyl-2-pentene is 95 to 99.9%; the selectivity of perfluoro-2, 3-epoxy-2-methylpentane is 95-98%.
Has the advantages that: the perfluoro-2, 3-epoxy-2-methylpentane is prepared by taking perfluoro-2-methyl-2-pentene as a raw material and carrying out an oxidation reaction in the presence of a specific dispersant and an oxidant. The conversion rate and the selectivity of the perfluoro-2, 3-epoxy-2-methylpentane both reach over 95 percent.
Detailed Description
The invention prepares perfluoro-2, 3-epoxy-2-methylpentane by oxidizing perfluoro-2-methyl-2-pentene, and the reaction is an exothermic reaction. A certain amount of energy must be supplied to bring it to the activated state. The temperature is too low, the reaction materials can not completely reach an activated state, and the conversion rate of the meta-perfluoro-2-methyl-2-pentene and the selectivity of perfluoro-2, 3-epoxy-2-methylpentane are influenced; too high a temperature, side reactions tend to occur more and the formation of perfluoro-2, 3-epoxy-2-methylpentane is unfavourable from the viewpoint of chemical equilibrium. Therefore, the reaction temperature is controlled within the range of 15-80 ℃ in the invention. In addition, in addition to the above reaction temperature affecting the reaction conversion rate and selectivity, the reaction pressure is also one of the important factors affecting the reaction effect. However, the reaction is considered to be an irreversible reaction because the conversion rate and selectivity of the reaction are high, but the pressure is too low, and the productivity per unit volume of the reactor is low, so that the reaction is uneconomical; the pressure is too high, and the requirements on equipment materials are strict, so that the invention comprehensively considers various factors, and the pressure control range is 0-0.6MPa.
Example 1:
putting perfluoro-2-methyl-2-pentene into a 5L reaction vessel, adding 2000ml30% to 2 O 2 Stirring an aqueous solution and 200ml of methyl ether, reducing the temperature to 15 ℃, adding 450g of perfluoro-2-methyl-2-pentene under the pressure of 0.2MPa, reacting for 8 hours, and rectifying the material at the outlet of the reactor to finally obtain the perfluoro-2, 3-epoxy-2-methylpentane. The conversion of perfluoro-4-methyl-2-pentene was calculated to be 98.0% and the selectivity of perfluoro-2, 3-epoxy-2-methylpentane was 97.8%.
Examples 2-4 the results are shown in Table I, with the same reaction temperature of 20 ℃, 50 ℃, 70 ℃ and other conditions being unchanged as in example 1.
Table one: selectivity and conversion of examples 2-4
Example 5:
putting perfluoro-2-methyl-2-pentene into a 5L reaction kettle, adding 3000ml of sodium hypochlorite aqueous solution with the effective chlorine content of 12% and 200ml of acetonitrile, starting stirring, cooling to 15 ℃, adding 450g of perfluoro-2-methyl-2-pentene under the pressure of 0.2MPa, reacting for 8 hours, and rectifying the material at the outlet of the reactor to finally obtain perfluoro-2, 3-epoxy-2-methylpentane. The conversion of perfluoro-4-methyl-2-pentene was calculated to be 95.4% with a selectivity of perfluoro-2, 3-epoxy-2-methylpentane of 98.2%.
Examples 6-8 the results are shown in Table II, except that the reaction temperature was changed to 20 ℃, 50 ℃ and 70 ℃ and the other conditions were changed as in example 5.
Table two: selectivity and conversion of examples 6-8
Example 9:
putting perfluoro-2-methyl-2-pentene into a 5L reaction kettle, charging oxygen with the oxygen content of 30% and 200ml of ethanol, starting stirring, cooling to 15 ℃, adding 450g of perfluoro-2-methyl-2-pentene under the pressure of 0.2MPa, reacting for 8 hours, and rectifying the material at the outlet of the reactor to finally obtain perfluoro-2, 3-epoxy-2-methylpentane. The conversion of perfluoro-4-methyl-2-pentene was calculated to be 96.1% and the selectivity of perfluoro-2, 3-epoxy-2-methylpentane was 97.2%.
In examples 10 to 12, the reaction temperature was changed to 20 ℃, 50 ℃ and 70 ℃ in the same manner as in example 9, and the other conditions were not changed, and the results are shown in Table III.
A third table: selectivity and conversion of examples 10-12
Examples 13 to 15 the same as example 9 except that the following conditions were changed to fill oxygen gas having oxygen contents of 28%, 35% and 40%, and the other conditions were not changed, the results are shown in Table four.
Table four: selectivities and conversions of examples 13-15
Claims (6)
1. A preparation method of epoxy perfluoropentane is characterized in that perfluoro-2-methyl-2-pentene and a dispersing agent react under the action of an oxidizing agent to obtain a product of perfluoro-2, 3-epoxy-2-methylpentane.
2. The process according to claim 1, wherein the reaction temperature is 15 to 80 ℃.
3. The process according to claim 1, wherein the reaction pressure is from 0 to 0.6MPa.
4. The method of claim 1, wherein the oxidizing agent is selected from the group consisting of 30% by volume H 2 O 2 At least one of an aqueous solution, a sodium hypochlorite solution with the volume concentration of 8% -15% and oxygen with the volume concentration of 30% -40%.
5. The method of claim 1, wherein the dispersant is selected from the group consisting of a mixture of one or more of methyl ether, ethanol, acetonitrile.
6. The process of any one of claims 1-5, wherein the perfluoro-2-methyl-2-pentene conversion is 95 to 99.9%; the selectivity of perfluoro-2, 3-epoxy-2-methylpentane is 95-98%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211267335.0A CN115490651A (en) | 2022-10-17 | 2022-10-17 | Preparation method of epoxy perfluoropentane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211267335.0A CN115490651A (en) | 2022-10-17 | 2022-10-17 | Preparation method of epoxy perfluoropentane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115490651A true CN115490651A (en) | 2022-12-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211267335.0A Pending CN115490651A (en) | 2022-10-17 | 2022-10-17 | Preparation method of epoxy perfluoropentane |
Country Status (1)
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| CN (1) | CN115490651A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105198719A (en) * | 2015-09-06 | 2015-12-30 | 浙江工业大学 | Preparation method of perfluoro-2-methyl-3-pentanone |
| CN106749108A (en) * | 2016-11-30 | 2017-05-31 | 上海三爱富新材料科技有限公司 | A kind of method for preparing the methylpentane of 2,3 epoxy of perfluor 2 |
| CN112142578A (en) * | 2020-10-26 | 2020-12-29 | 安徽天辰云泽安全科技有限公司 | Preparation method of perfluorohexanone |
-
2022
- 2022-10-17 CN CN202211267335.0A patent/CN115490651A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105198719A (en) * | 2015-09-06 | 2015-12-30 | 浙江工业大学 | Preparation method of perfluoro-2-methyl-3-pentanone |
| CN106749108A (en) * | 2016-11-30 | 2017-05-31 | 上海三爱富新材料科技有限公司 | A kind of method for preparing the methylpentane of 2,3 epoxy of perfluor 2 |
| CN112142578A (en) * | 2020-10-26 | 2020-12-29 | 安徽天辰云泽安全科技有限公司 | Preparation method of perfluorohexanone |
Non-Patent Citations (1)
| Title |
|---|
| 张付利主编: "《绿色化学应用及发展》", 国防工业出版社, pages: 52 * |
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