1187-93-5

Basic information

• Product Name: Trifluoromethyl trifluorovinyl ether
• Synonyms: ethene,trifluoro(trifluoromethoxy)-;ether,trifluoromethyltrifluorovinyl;perfluorinatedmethylvinylether;Perfluoro(methylvinylether);perfluorovinylperfluoromethylether;trifluoro(trifluoromethoxy)-ethen;trifluoro(trifluoromethoxy)-Ethene;trifluoro(trifluoromethoxy)ethylene
• CAS NO: 1187-93-5
• Molecular Formula: C3F6O
• Molecular Weight: 166.02
• EINECS: 214-703-7
• Product Categories: Fluoromonomer
• Mol File: 1187-93-5.mol

Chemical Properties

• Boiling Point: -22 °C
• Flash Point: -32.898 °C
• Appearance: Colorless gas
• Density: 1.3210 (estimate)
• Vapor Pressure: 1090mmHg at 25°C
• Refractive Index: 1.264
• Water Solubility: 31.5mg/L at 28℃
• CAS DataBase Reference: Trifluoromethyl trifluorovinyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Trifluoromethyl trifluorovinyl ether(1187-93-5)
• EPA Substance Registry System: Trifluoromethyl trifluorovinyl ether(1187-93-5)

Safety Data

• Hazard Codes: F
• Statements: 20
• Safety Statements: 23-38
• RIDADR: 3153
• RTECS: KO4350000
• TSCA: T
• HazardClass: GAS, FLAMMABLE
• Hazardous Substances Data: 1187-93-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
Trifluoromethyl trifluorovinyl ether is used as a chemical intermediate for the synthesis of various fluorinated compounds. Its unique properties, such as being heavier than air and easily liquefied, make it suitable for use in the production of specialty chemicals and materials.
Used in Firefighting:
Due to its ability to displace air and potentially cause asphyxiation, trifluoromethyl trifluorovinyl ether can be used in firefighting applications where it can help to smother fires by reducing the oxygen supply. However, caution must be taken to avoid the risk of flash backs and container rupture under certain conditions.
Used in Research and Development:
Trifluoromethyl trifluorovinyl ether's unique properties make it an interesting compound for research and development in various fields, including materials science, chemical engineering, and environmental science. Its potential applications in these areas are still being explored and may lead to new discoveries and innovations.
Used in Safety and Hazardous Material Handling:
Given the potential hazards associated with trifluoromethyl trifluorovinyl ether, such as frostbite, asphyxiation, and the risk of flash backs, it is essential to use this compound in industries that specialize in safety and hazardous material handling. These industries can develop protocols and equipment to safely manage and utilize the compound in various applications.

Air & Water Reactions

Highly flammable.

Reactivity Profile

Trifluoromethyl trifluorovinyl ether oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979. p.151-154, 164].

Health Hazard

Vapors may cause dizziness or asphyxiation without warning. Some may be irritating if inhaled at high concentrations. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire may produce irritating and/or toxic gases.

Fire Hazard

EXTREMELY FLAMMABLE. Will be easily ignited by heat, sparks or flames. Will form explosive mixtures with air. Vapors from liquefied gas are initially heavier than air and spread along ground. CAUTION: Hydrogen (UN1049), Deuterium (UN1957), Hydrogen, refrigerated liquid (UN1966) and Methane (UN1971) are lighter than air and will rise. Hydrogen and Deuterium fires are difficult to detect since they burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.) Vapors may travel to source of ignition and flash back. Cylinders exposed to fire may vent and release flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket.

Flammability and Explosibility

Flammable

InChI:InChI=1/C3F6O/c4-1(5)2(6)10-3(7,8)9

Upstream product

• 24499-36-3 sodium perfluoro-β-methoxypropionate 
• 79630-79-8 calcium perfluoro-β-methoxypropionate 
• 17636-84-9 perfluoro(dimethyl-2-methoxybutylamine) 
• 25032-69-3 potassium perfluoro-β-methoxypropionate 
• 79630-78-7 baryum perfluoro-β-methoxypropionate 
• 2356-53-8 1-trifluoromethoxy-1,2-dichlorotrifluoroethane 
• 116-15-4 perfluoropropylene 
• 36336-08-0 methyl hypofluorite 
• 425-38-7 perfluoro-3-methoxypropionyl fluoride 
• 1479-49-8 bis(trifluoromethyl) ether 
• 353-50-4 Carbonyl fluoride 
• 79-38-9 Chlorotrifluoroethylene 
• 2927-83-5 2,3,3,3-tetrafluoro-2-(trifluoromethoxy)propionic acid fluoride 

Downstream Products

• 422-61-7 perfluoropropanoyl fluoride 
• 2356-55-0 1-bromo-1,1,2-trifluoro-2-(trifluoromethoxy)ethane 
• 2356-53-8 1-trifluoromethoxy-1,2-dichlorotrifluoroethane 
• 1561-52-0 Trifluormethyl-<1,1,2,2-tetrafluor-2-iod-ethyl>-ether 
• 2356-57-2 1,2-Dibrom-trifluoraethyl-trifluormethyl-aether 
• 99728-23-1 4-phenoxy-3-(trifluoromethoxy)-1,1,1,3,4,4-hexafluorobutan-2-one 
• 144219-48-7 3-Fluoro-4-(1,1,2-trifluoro-2-trifluoromethoxy-ethoxy)-phenylamine 
• 122267-39-4 2-fluoro-4-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]-aniline 
• 122267-40-7 2-chloro-4-[1,1,2-trifluoro-2-(trifluoromethoxy)-ethoxy]-aniline 
• 116714-47-7 3-chloro-4-[ 1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy] aniline 
• 139604-89-0 1-Iodoperfluoro-1-methoxyethane 
• 139604-91-4 2-Iodo-1-chloroperfluoro-1-methoxyethane 
• 139604-90-3 1-Iodo-2-chloroperfluoro-1-methoxyethane 
• 144219-47-6 4-(1,1,2-Trifluoro-2-trifluoromethoxy-ethoxy)-phenylamine 

Relevant articles and documents

Methyl hypofluorite (MeOF) reactions with various fluoroolefins

The reaction of methyl hypofluorite (MeOF) with certain fluoroolefins, such as CF2=CF2, CF2=CFCF3, CF2=CFOCF3, CF2=CFOMe, CF2=CClF, CF2=CHF, CF2=CH2, CHF=CH2, CF2=CFCF=CF2, occurred in CD3CN or in the presence of NaF. Using neat MeOF in the presence of NaF was a novel method and gave good results. We observed that when more than three fluorine atoms are bonded to the C-C double bond, the addition products were obtained in mostly good yields.

PROCESS FOR THE PRODUCTION OF PERFLUORINATED ALKYLVINYLETHERS

The present invention relates to a process for producing a perfluorovinylether A-CRf=CF-O-B, comprising the steps of : - contacting at least one α,β-dihaloperfluoro ether represented by the formula A-CRfX-CFX-O-B with zero valent zinc in the presence of an organic nitrogen compound selected in the group consisting of: tertiary aliphatic amines; aromatic heterocycles comprising nitrogen as heteroatom; and guanidines; to form a mixture comprising perfluorovinylether, and - recovering the perfluorovinylether from the mixture, wherein : X is selected from the group consisting of chlorine, bromine, or iodine, Rf is fluorine or is a group of formula –OR'f, where R'f is selected from the group consisting of linear and branched chain perfluoroalkyl radicals A is selected from the group consisting of fluorine and linear and branched chain perfluoroalkyl radicals, and B is selected from the group consisting of linear and branched chain perfluoroalkyl radicals, wherein A and B can contain oxygen and sulfur heteroatoms configured in functional groups selected from ether, ester, ketone, and sulfonyl fluoride, and wherein A and B can be bonded together forming a ring.

Method for preparing perfluoromethyl vinyl ether

The invention provides a three-step method for preparing perfluoromethyl vinyl ether. The method uses 2-methoxypropanol and perfluoro-2-methoxypropionyl fluoride as raw materials, and conducts an esterification reaction, a fluorination reaction and a thermal decomposition reaction to obtain the fluoromethyl vinyl ether. The method provided by the invention is stable in reaction conditions, easy for industrialized continuous production; and the product perfluoromethyl vinyl ether has high yield and high purity.

METHOD FOR THE MANUFACTURE OF PERFLUOROVINYLETHERS

A method for the hydrodehalogenation of a halofluoroether (HaloFE) having general formula (l-A) or (l-B): (I-A) RfO-CRf'X-CRf"Rf"'X' wherein - Rf represents a C1-C6 perfluoroalkyl or a C1-C6 perfluorooxyalkyl group; - Rf', Rf" and Rf'", equal or different from each other, independently represent fluorine atoms or C1-C5 perfluoroalkyl or C1-C5 perfluorooxyalkyl groups; X and X', equal or different from each other, are independently selected from CI, Br or I; (l-B) wherein: - Rf* and Rf*', equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoroalkyl or C1-C3 perfluorooxyalkyl groups; - Y1 and Y2, equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoroalkyl groups; X and X' are as above defined; is herein disclosed, the method comprising contacting said halofluoroether (HaloFE) with hydrogen in the presence of a catalyst comprising at least one transition metal of group VI 11 B and at least one alkali metal of group IA.

METHOD FOR THE MANUFACTURE OF PERFLUOROVINYLETHERS

The invention pertains to a method for the manufacture of a perfluorovinylether by hydrodehalogenation of a halofluoroether (HaloFE) having general formula (l-A) or RfO-CRf'X-CRf"Rf"'X' (l-A) wherein Rf represents a C1-C6 perfluoro(oxy)alkyl group; Rf', Rf" and Rf'", equal or different from each other, independently represent fluorine atoms or C1-C5 perfluoro(oxy)alkyl groups; X and X', equal or different from each other, are independently selected from CI, Br or I; (l-B) wherein Rf* and Rf*', equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoro(oxy)alkyl groups; Y1 and Y2, equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoroalkyl groups; X and X' are as above defined; said method comprising contacting said halofluoroether (HaloFE) with hydrogen in the presence of a catalyst comprising at least one transition metal (M) of group VI 11 B and tin.

Perfluoromethyl vinyl ether preparation method

The present invention discloses a perfluoromethyl vinyl ether preparation method, wherein a trifluoromethoxy salt CF3OM is adopted as a raw material, and reacts with chlorotrifluoroethylene in the presence of a phase transfer agent to prepare the perfluoromethyl vinyl ether. The present invention further discloses a preparation method of the perfluoromethyl vinyl ether. According to the present invention, the preparation method has characteristics of high product yield, low risk factor, safety and environmental protection, and is suitable for industrial production.

Methods for producing perfluoromethyl vinyl ether and intermediate thereof

The invention discloses a method for producing perfluorinated-2-methoxy propionyl fluorine. In the presence of a polar aprotic solvent, under the action of a main catalyst alkali metal fluoride and a phase transfer catalyst, carbonyl fluoride and hexafluoropropylene oxide react to prepare perfluorinated-2-methoxy propionyl fluorine. The invention further provides a method for preparing perfluoromethyl vinyl ether from perfluorinated-2-methoxy propionyl fluorine. According to the methods, the reaction yield is high, the prepared products are high in purity, operation is easy, and environment friendliness is achieved.

Method for Preparing Fluorine-Containing Vinyl Ether

Provided is a method for preparing fluorine-containing vinyl ether. The method comprises: carrying out hydrolytic neutralization on a small molecular weight byproduct which is produced in the process of preparing perfluoropolyether or a perfluorinated surfactant by photooxidation of fluorine-containing olefin; and obtaining fluorine-containing vinyl ether by drying and cracking. The byproduct produced in the process of preparing perfluoropolyether or the perfluorinated surfactant is utilized, thereby solving the emission problem of industrial wastes, reducing environment pollution, and generating available fluorine-containing vinyl ether.

Method for manufacturing perfluorovinylethers

The invention pertains to a process for the manufacture of a perfluorovinylether by hydrodehalogenation of a halofluoroether (HFE) having general formula (I-A) or (I-B): [in-line-formulae]RfO—CRf′X—CRf″Rf′″X″??(I-A)[/in-line-formulae] wherein Rf represents a C1-C6 perfluoro(oxy)alkyl group; Rf′, Rf″ and Rf′″, equal or different from each other, independently represent fluorine atoms or C1-C5 perfluoro(oxy)alkyl groups; X and X′, equal or different from each other, are independently chosen among Cl, Br or I; wherein Rf* and Rf*′, equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoro(oxy)alkyl groups; Y1 and Y2, equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoroalkyl groups; X and X′ are as above defined; said process comprising contacting said halofluoroether (HFE) with hydrogen in the presence of a catalyst comprising palladium and at least one transition metal (M) selected from the group consisting of the metals of group VIIIB, other than palladium, and of group IB.

METHOD FOR MANUFACTURING PERFLUOROVINYLETHERS

The invention pertains to a process for the manufacture of a perfluorovinylether by hydrodehalogenation of a halofluoroether (HFE) having general formula (l-A) or (l-B): RfO-CRf'X-CRf"Rf"'X' (l-A) wherein Rf represents a C1-C6 perfluoro(oxy)alkyl group; Rf', Rf" and Rf'", equal or different from each other, independently represent fluorine atoms or C1-C5 perfluoro(oxy)alkyl groups; X and X', equal or different from each other, are independently chosen among CI, Br or I; wherein Rf* and Rf*', equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoro(oxy)alkyl groups; Y1 and Y2, equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoroalkyl groups; X and X' are as above defined; said process comprising contacting said halofluoroether (HFE) with hydrogen in the presence of a catalyst comprising palladium and at least one transition metal (M) selected from the group consisting of the metals of group VIIIB, other than palladium, and of group IB.