CN115785029A - Preparation method of perfluoro-2-methyl-2, 3-epoxypentane - Google Patents
Preparation method of perfluoro-2-methyl-2, 3-epoxypentane Download PDFInfo
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- CN115785029A CN115785029A CN202211572233.XA CN202211572233A CN115785029A CN 115785029 A CN115785029 A CN 115785029A CN 202211572233 A CN202211572233 A CN 202211572233A CN 115785029 A CN115785029 A CN 115785029A
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- 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 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 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 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 238000006735 epoxidation reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 150000002978 peroxides Chemical group 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000005708 Sodium hypochlorite Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- -1 perfluoro Chemical group 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- KGAHKQBZVJJFBW-UHFFFAOYSA-N 1,1,1,2,2,6,6,7,7,7-decafluoro-3,3,5,5-tetrakis(trifluoromethyl)heptan-4-one Chemical compound FC(F)(F)C(F)(F)C(C(F)(F)F)(C(F)(F)F)C(=O)C(C(F)(F)F)(C(F)(F)F)C(F)(F)C(F)(F)F KGAHKQBZVJJFBW-UHFFFAOYSA-N 0.000 description 1
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- WDXWKUDBPNCHTK-UHFFFAOYSA-N [N]=O.CN(C)C Chemical compound [N]=O.CN(C)C WDXWKUDBPNCHTK-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MMAXOAIHEPNELR-UHFFFAOYSA-N n,n-dimethylcyclohexanamine oxide Chemical compound C[N+](C)([O-])C1CCCCC1 MMAXOAIHEPNELR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- ZXNLNZJZSYSNKM-UHFFFAOYSA-M potassium hydrogen peroxide hydroxide Chemical compound [OH-].[K+].OO ZXNLNZJZSYSNKM-UHFFFAOYSA-M 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a preparation method of perfluoro-2-methyl-2, 3-epoxypentane. Adding perfluoro-2-methyl-2-pentene into a solvent with the mass 5-10 times that of the perfluoro-2-methyl-2-pentene, adding acetone with the mass 1-10% of that of the perfluoro-2-methyl-2-pentene, cooling to-20-0 ℃, introducing ozone with a certain concentration, heating to 20-50 ℃, stirring for 2-8 hours, directly rectifying, and collecting fraction with the temperature of 52-54 ℃ to obtain the perfluoro-2-methyl-2, 3-cyclopentane epoxide. The method has the advantages of mild reaction conditions, high reaction yield and little environmental pollution.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a preparation method of perfluoro-2-methyl-2, 3-epoxypentane.
Background
Perfluoro-2-methyl-2, 3-epoxypentane, CAS:788-67-0, boiling point 53 deg.C, is an important fluorine-containing chemical, and can be used as fire extinguishing agent, cleaning agent, solvent, etc. The intermediate can be used for synthesizing perfluorohexanone, fluorine-containing ether solvent and the like, and has wide production application and market prospect. Perfluoro-2-methyl-2, 3-epoxypentane has various preparation methods.
(1) Preparation of perfluoro-2-methyl-2, 3-epoxypentane (Oxides of fluoroolefins.1.New method for the synthesis of fluorinated epoxykanes [ J ] IZVEstia Akademii Nauk SSSR, seriya Khimicisk aya, (11), 2509-12.
(2) Perfluoro-2-methyl-2, 3-cyclopentane is prepared by Philip epoxidizing perfluoro-2-methyl-2-pentene with an oxidant of trimethylamine nitrogen oxide in Ono, taizo and Henderson (Novel epoxidation of perfluor olefins with trimethylamine N-oxide and iodosylbenzene [ J ] Tetrahedron Letters,43 (44), 7961-7965.
(3) The preparation of perfluoro-2-methyl-2, 3-epoxypentane (Novel epoxidation reaction of perfluoroalkenes with triethyleneme [ J ] Asian Journal of Chemistry,24 (5) 2357-2352012) by using triethylamine oxynitride as oxidant to epoxidize perfluoro 2-methyl-2-pentene by Cai, xingwei, etc..
(4) Fayemi, bamidel O, etc. epoxidize perfluoro-2-methyl-2, 3-epoxypentane with a hydrogen peroxide potassium hydroxide system to produce perfluoro-2-methyl-2, 3-epoxypentane (Fluorinated oxygenates as organic Rankine cycle gases and methods of using same [ P ] PCT Int. Appl.,2012134803,04Oct 2012).
(5) The Epoxidation of perfluoro-2-methyl-2, 3-cyclopentane by Cai, xing Wei, etc. using tributylamine oxynitride as an oxidizing agent to produce perfluoro-2-methyl-2, 3-cyclopentane (Epoxidation of perfluor aldehydes with tert-amine N-oxide [ J ] Chinese Chemical Letters,23 (11), 1237-1239.
(6) Du, jianke et al epoxidize perfluoro 2-methyl-2-pentene with sodium hypochlorite, changing the reaction conditions (Preparation method of perfluorethyl isopropyl ketone [ P ] CN 102992986).
(7) Sha, min et al further epoxidize perfluoro 2-methyl-2-pentene (One-pot catalytic oxidation reaction of perfluor-2-methyl-2-pentene with tri-nbutylamine N-oxide or N, N-Dimethylcyclohexylamine N-oxide [ J ] Advanced Materials Research (Durnten-Zurich, itzerland), 685,357-361, pp 6.; 2013) by oxidizing tributylamine et al with m-chloroperoxybenzoic acid as an oxidizing agent.
(8) Chen, yanfeng et al synthesized perfluoro-2,3-epoxy-2-methylpentane (Method for preparing perfluor-2, 3-epoxy-2-methyl pentane, CN 106749108) by molecular oxygen oxidation.
(9) Miao, guangzhou et al use calcium hypochlorite as an epoxidizing agent (Method for synthesizing perfluorohexanone, CN 107382692).
(10) Jiang, biao et al used a continuous process using sodium hypochlorite as an epoxidation reagent (Method for continuous preparation of perfluor-2-methyl-3-pentanone, CN 107879912).
(11) The Cai, xingwei, etc. uses perfluoro-4-methyl-2-pentene or a mixture of perfluoro-4-methyl-2-pentene and perfluoro-2-methyl-2-pentene as a raw material, converts the perfluoro-4-methyl-2-pentene into perfluoro-2-methyl-2-pentene through an isomerization reaction, epoxidizes the perfluoro-2-methyl-2-pentene into perfluoro-2-methyl-2, 3-cyclopentane, and catalytically rearranges the perfluoro-2-methyl-2, 3-cyclopentane into perfluoroethyl isopropyl ketone. The method has the advantages that the catalytic isomerization reaction can be carried out without solvent, thereby avoiding the problems of large use of toxic solvent, difficult recycling and the like in the prior art; the method adopts tertiary amine oxynitride or N, N-dialkyl hydroxylamine as an epoxidation reagent, realizes the quantitative conversion of perfluoro-2-methyl-2-pentene into perfluoro-2-methyl-2, 3-epoxypentane under mild conditions, and avoids the problems of large amount of sodium hypochlorite solution, severe corrosion of equipment, difficult recovery of a large amount of brine generated by aftertreatment, harsh use conditions and the like in the prior art. Andenza et al concluded the epoxidation of perfluoro (polyfluoro) olefins (ranistrength, panyan, nihon, the progress of the epoxidation of perfluoro (polyfluoro) olefins, chekiang chemical, vol 46, vol 12, 2015, 1-4).
However, the existing preparation technology of perfluoro-2-methyl-2, 3-epoxypentane generally has the problems of low reaction yield and great environmental pollution.
Disclosure of Invention
The invention aims to overcome the problems of low reaction yield and great environmental pollution in the prior art for preparing perfluoro-2-methyl-2, 3-epoxypentane, and provides a preparation method of perfluoro-2-methyl-2, 3-epoxypentane.
The technical scheme of the invention is as follows:
the invention provides a preparation method of perfluoro-2-methyl-2, 3-epoxypentane, which comprises the following steps:
adding perfluoro-2-methyl-2-pentene into a solvent, adding acetone accounting for 1-10% of the mass of the perfluoro-2-methyl-2-pentene, cooling to-20-0 ℃, introducing ozone into the solvent, heating to 20-50 ℃ after the ozone introduction is finished, stirring for 2-8 hours, and separating a product after the reaction is finished to obtain the perfluoro-2-methyl-2, 3-cyclopentane epoxide.
In a preferred embodiment of the present invention, the solvent is one or more of acetonitrile, dimethylformamide or dimethylsulfoxide.
In a preferred embodiment of the present invention, the amount of the solvent is 5 to 10 times the mass of perfluoro-2-methyl-2-pentene.
As a preferable embodiment of the present invention, the concentration of ozone introduced into the solvent is 80 to 120g/m 3 。
As a preferable scheme of the invention, the flow rate of the ozone introduced into the solvent is 50-200mL/min; the ozone is introduced for 2-5 hours.
As a preferred scheme of the invention, the method for separating the reaction product is to directly rectify the organic phase reaction product at normal pressure, and collect the fraction with the temperature of 52-54 ℃ at the top of the tower, namely the perfluoro-2-methyl-2, 3-epoxypentane.
Compared with the prior art, the invention has the beneficial effects that:
the invention selects acetone and ozone as epoxidation reagents, and realizes the following reactions in one step:
the disclosed prior art is mainly a process for generating a large amount of brine through sodium hypochlorite and the like, which severely corrodes equipment and is difficult to recover in post-treatment:
the invention solves the technical problem that the prior art generates a large amount of waste water and waste residue by generating the epoxidation reagent in situ and optimizing the material proportion and reaction process parameters; the process of the invention has the advantages of less waste water and waste residue, safe and easily obtained raw materials, and suitability for industrial production.
By optimizing the reaction process and the post-treatment process, the purity of the obtained product is up to more than 99 percent through GC detection, and compared with the prior art, the yield and the product purity of the target product are improved.
Drawings
FIG. 1 is a gas chromatogram for measuring perfluoro-2-methyl-2, 3-epoxypentane in example 1.
Detailed Description
The invention will be further illustrated and described with reference to specific embodiments. The technical characteristics of the embodiments of the invention can be correspondingly combined without mutual conflict.
The preparation method of the perfluoro-2-methyl-2, 3-epoxypentane provided by the invention can be carried out according to the following steps: adding perfluoro-2-methyl-2-pentene into a solvent, adding acetone accounting for 1-10% of the mass of the perfluoro-2-methyl-2-pentene, cooling to-20-0 ℃, then introducing ozone into the solvent, heating to 20-50 ℃, stirring for reacting for 2-8 hours, and separating a product after the reaction is finished to obtain the perfluoro-2-methyl-2, 3-cyclopentane epoxide.
In the above method, the solvent is used as a medium for the reaction, and is required to be capable of dissolving or dispersing the raw material perfluoro-2-methyl-2-pentene well, so that the reaction can be carried out gently. Preferably, the solvent is an organic solvent, preferably an organic solvent having a certain solubility to ozone. More preferably, the solvent is one or more of acetonitrile, dimethylformamide or dimethylsulfoxide. Although the amount of the solvent is not particularly limited in general, it can be generally used in the art, and the amount of the solvent is preferably 5 to 10 times the amount of perfluoro-2-methyl-2-pentene added to ensure the amount of ozone added.
In the above method, ozone is usually generated by an ozone generator, and the ozone is introduced into the solvent by a method conventional in the art, and preferably, the concentration of the ozone introduced into the solvent is 50 to 120g/m 3 The flow rate of the ozone introduced into the solvent is 50-200mL/min; the ozone is introduced for 2-5 hours. The concentration of ozone in the solvent is detected or measured using methods conventional in the art.
In the above method, the rotation speed of the reaction stirring is not particularly limited, the stirring is performed for the purpose of making the reaction more uniform, and generally, the higher the rotation speed of the stirring, the more sufficient the stirring is, but the power required for the stirring is increased (thereby causing an increase in the stirring cost); therefore, the stirring can be carried out at the stirring speed recommended by the design of a common stirring reactor in industrial production.
In the above method, the separation of the reaction product may be performed by selecting the difference in physical and chemical properties between the target product and other compounds in the reaction product mixture. For example, it can be carried out by a difference in boiling point, solubility in a specific solvent, or the like. Preferably, the product separation is carried out by rectification, and more preferably, the fraction with the temperature of 52-54 ℃ is collected by normal pressure rectification, namely, the high-purity perfluoro-2-methyl-2, 3-epoxypentane is obtained.
Example 1
50 g of perfluoro-2-methyl-2-pentene were added to 250 g of acetonitrile, 0.5 g of acetone was added, the mixture was cooled to 0 ℃ and a concentration of 80g/m was passed through 3 The flow rate of the ozone is 100mL/min, the ozone generator is closed after the ozone is continuously introduced for 2 hours, the temperature is increased to 20 ℃ for reaction, the stirring is carried out for 8 hours, starch potassium iodide test paper is used for testing whether peroxide residues exist after the reaction is finished, if no peroxide residues exist, the organic phase is rectified at normal pressure, fractions at 52-54 ℃ are collected, 502 g of perfluoro-2-methyl-2, 3-epoxypentane is obtained, the yield is 95.2%, and the purity is 99.69% (a gas chromatogram is shown in figure 1, and a gas chromatogram is shown in figure 1, which corresponds to 7.423min and is the perfluoro-2-methyl-2, 3-epoxypentane, and the content is 99.6973%).
The detection result of the product perfluoro-2-methyl-2, 3-epoxypentane is as follows: IR (KBr, v/cm-1) 1468, 19 F NMRδ:-54.0～-54.8(1F),-77.0～-80.5(2F),-118.0～-118.5(3F),-133.0～-133.5(3F),-133.7～-134.0(3F)。
example 2
50 g of perfluoro-2-methyl-2-pentene were added to 300 g of dimethylformamide, 2.5 g of acetone was added, the mixture was cooled to-10 ℃ and the concentration was passed through a tube at 100g/m 3 The flow rate of the ozone is 100mL/min, the ozone generator is closed after the ozone is continuously introduced for 4 hours, the temperature is increased to 30 ℃ for reaction, the stirring is carried out for 4 hours, starch potassium iodide test paper is used for testing whether peroxide residue exists after the reaction, if no peroxide residue exists, the organic phase is rectified at normal pressure, the fraction at 52 to 54 ℃ is collected, 50.2 g of perfluoro-2-methyl-2, 3-epoxy pentane is obtained, the yield is 95.2 percent,
example 3
50 g of perfluoro-2-methyl-2-pentene are added to 500 g of dimethyl sulfoxide, 5.0 g of acetone are added, the mixture is cooled to-20 ℃ and the concentration of 120g/m is passed through 3 The flow of the ozone is 100mL/min, after the ozone is introduced for 5 hours, the ozone generator is closed, the temperature is raised to 50 ℃ for reaction, the reaction is stirred for 2 hours, starch potassium iodide test paper is used for testing whether peroxide residues exist or not after the reaction is finished, if no peroxide residues exist, the organic phase is rectified at normal pressure, fractions at 52 to 54 ℃ are collected, and perfluoro-2-methyl-2, 3-cyclopentane is obtained, 96.8 percent of 51.0 g, and the purity is 99.35 percent.
Comparative example 1
Adding 80ml of sodium hypochlorite aqueous solution and 80ml of acetonitrile into a 500ml three-neck flask, dropwise adding 15 g of perfluoro-2-methyl-2-pentene at room temperature, reacting for 5 hours, stopping stirring after the reaction is finished, standing, separating a lower layer, drying by anhydrous magnesium sulfate, filtering, distilling to obtain 11 g of perfluoro-2-methyl-2, 3-epoxypentane with the purity of 98.50%. More than 80ml of wastewater containing high salt was produced.
Comparative example 2
50 g of perfluoro-2-methyl-2-pentene are added to 250 g of acetonitrile, cooled to 0 ℃ and passed through at a concentration of 80g/m 3 The flow of the ozone is 100mL/min, after the ozone is introduced for 2 hours, the ozone generator is closed, the temperature is increased to 20 ℃ for reaction, the stirring is carried out for 8 hours, after the reaction is finished, a starch potassium iodide test paper is used for testing whether peroxide residues exist, if no peroxide residues exist, the organic phase is rectified at normal pressure, and no product is generated.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present invention should be subject to the appended claims.
Claims (6)
1. A preparation method of perfluoro-2-methyl-2, 3-cyclopentane oxide is characterized by comprising the following steps:
adding perfluoro-2-methyl-2-pentene into a solvent, adding acetone accounting for 1-10% of the mass of the perfluoro-2-methyl-2-pentene, cooling to-20-0 ℃, then introducing ozone into the solvent, heating to 20-50 ℃ after the ozone introduction is finished, stirring for reacting for 2-8 hours, and separating a reaction product after the reaction is finished to obtain the perfluoro-2-methyl-2, 3-cyclopentane.
2. The process of claim 1, wherein the solvent is one or more of acetonitrile, dimethylformamide or dimethylsulfoxide.
3. The process for preparing perfluoro-2-methyl-2, 3-epoxypentane of claim 1, wherein the amount of said solvent is 5 to 10 times the mass of perfluoro-2-methyl-2-pentene.
4. The process for producing perfluoro-2-methyl-2, 3-epoxypentane according to claim 1, wherein the concentration of ozone introduced into the solvent is 80 to 120g/m 3 。
5. The process for producing perfluoro-2-methyl-2, 3-epoxypentane as claimed in claim 1 or 4, wherein the flow rate of ozone introduced into the solvent is 50 to 200mL/min; the ozone is introduced for 2-5 hours.
6. The process for preparing perfluoro-2-methyl-2, 3-epoxypentane as claimed in claim 1, wherein the method for separating the reaction product is to directly rectify the organic phase reaction product at normal pressure, and collect the fraction at 52-54 ℃ at the top of the column, i.e. perfluoro-2-methyl-2, 3-epoxypentane.
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| CN103787854A (en) * | 2014-01-24 | 2014-05-14 | 奥瑞安有限公司 | Preparation process of perfluoro-2-methyl-3-pentanone |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103787854A (en) * | 2014-01-24 | 2014-05-14 | 奥瑞安有限公司 | Preparation process of perfluoro-2-methyl-3-pentanone |
Non-Patent Citations (2)
| Title |
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| FERRAZ HELENA M.C.等: "A simple and efficient protocol for epoxidation of olefins using dimethyldioxirane", 《TETRAHEDRON LETTERS》, vol. 41, pages 5021 - 5023 * |
| 孙苏赟: "双键的环氧化反应（二）", pages 1, Retrieved from the Internet <URL:https://cn.chem-station.com/reactions/2020/03/双键的环氧化反应（二）.html> * |
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