2356-53-8

Usage

Uses

Used in Fire Suppression Systems:
1,2-Dichlorotrifluoroethyl trifluoromethyl ether is used as a fire-extinguishing agent for its effectiveness in suppressing fires in enclosed spaces. It is particularly suitable for applications where traditional water-based fire suppression methods may not be practical, such as in computer server rooms, aircraft, and some industrial settings.
Used in Environmentally Sensitive Applications:
Due to its relatively low toxicity compared to other halogenated fire-extinguishing agents, 1,2-Dichlorotrifluoroethyl trifluoromethyl ether was once preferred for use in environments where minimizing environmental impact was crucial. However, its potential contribution to ozone depletion has led to the development and adoption of more environmentally-friendly fire suppression alternatives.
Used in Historical Industrial Settings:
Before the awareness of its environmental impact, 1,2-Dichlorotrifluoroethyl trifluoromethyl ether was commonly used in certain industrial settings where its fire-fighting capabilities were essential for safety. The phasing out of 1,2-DICHLOROTRIFLUOROETHYL TRIFLUOROMETHYL ETHER has led to the search for and implementation of alternative fire suppression methods that are both effective and environmentally responsible.

InChI:InChI=1/C3Cl2F6O/c4-1(6,7)2(5,8)12-3(9,10)11

Upstream product

• 156-59-2 cis-1,2-Dichloroethylene 
• 373-91-1 hypofluorous acid trifluoromethyl ester 
• 598-88-9 1,2-dichloro-1,2-difluoroethene 
• 156-60-5 trans-1,2-dichloroethylene 
• 353-50-4 Carbonyl fluoride 
• 201230-82-2 carbon monoxide 
• 94720-91-9 CF₃O-CCl=CClF 
• 359-11-5 1,1,2-trifluoroethylene 
• 79-38-9 Chlorotrifluoroethylene 
• 79-01-6 Trichloroethylene 
• 75-38-7 Vinylidene fluoride 
• 75-02-5 1-fluoroethylene 
• 311-81-9 cis-1,2-dichloro-1,2-difluoroethene 
• 127-18-4 1,1,2,2-tetrachloroethylene 

Downstream Products

• 1187-93-5 trifluoromethyl trifluorovinyl ether 
• 2356-59-4 1,1,2-Trifluor-1-chlor-2-trifluormethoxy-aethan 

Relevant academic research and scientific papers

PROCESS FOR PREPARING FLUOROHALOGENOETHERS

The present invention concerns a process for preparing fluorohalogenoethers in a microreactor.

Method for preparing fluorine-containing halogenated ether

The invention relates to a method for preparing fluorine-containing halogenated ether, belonging to the technical field of organofluorine chemistry. The method comprises the following steps: using fluorooxytrifluoromethane and halogenated alkene as raw materials and continuously feeding gas phase halogenated alkene and gas phase fluorooxytrifluoromethane into a reactor to undergo thermal addition reaction to obtain fluorine-containing halogenated ether; controlling the spray pressure of fluorooxytrifluoromethane to be 0.1-1MPa, the reaction temperature to be 80-200 DEG C and the mole ratio of fluorooxytrifluoromethane to halogenated alkene to be (0.6-1.3) to 1. The method has the beneficial technical effects that the two raw materials are in gas phase; continuous obtainment of fluorine-containing halogenated ether with high yield and efficiency can be ensured by controlling the specific spray pressure of fluorooxytrifluoromethane, the specific reaction temperature and the specific reaction raw material ratio; the method only adopts two kinds of reaction raw materials, is simple in process, can be used for continuous production, has the advantages of low metering requirements, convenience in operation and high yield and efficiency and is very suitable for industrial production.

Process for preparing fluorohalogenethers

A process for preparing perfluorovinylethers having general formula: ???????? RfO-CF=CF2?????(IA) wherein Rf is a C1-C3 alkyl perfluorinated substituent; comprising the following steps: 1a) fluorination with fluorine of olefins of formula: ???????? CY"Y=CY'Cl?????(II) wherein Y, Y' and Y", equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y' and Y" are not contemporaneously hydrogen; and obtainment of fluorohalogencarbons of formula: ???????? FCY"Y-CY'ClF?????(III) wherein Y, Y' and Y" are as above; 2a) dehalogenation or dehydrohalogenation of the fluorohalogencarbons (III) and obtainment of fluorohalogen olefins of formula: ???????? FCYI=CYIIF?????(IV) wherein YI and YII, equal to or different from each other, have the meaning of H, Cl, Br with the proviso that YI and YII are not both H; 3a) reaction between a hypofluorite of formula RfOF and a fluorohalogenolefin (IV), obtaining the fluorohalogenethers of formula: ???????? RfO-CFYI-CF2YII?????(I) wherein YI, YII, equal to or different from each other, are Cl, Br, H with the proviso that YI and YII cannot be contemporaneously equal to H; 4a) dehalogenation or dehydrohalogenation of the compounds (I) and obtainment of the perfluorovinylethers (IA).

Process for preparing fluorohalogenethers

A process for preparing perfluorovinylethers having general formula: [in-line-formulae]RfO—CF═CF2 ??(IA)[/in-line-formulae] wherein Rf is a C1-C3 alkyl perfluorinated substituent; comprising the following steps: 1a) fluorination with fluorine of olefins of formula: [in-line-formulae]CY″Y═CY′Cl ??(II)[/in-line-formulae]wherein Y, Y′ and Y″, equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y′ and Y″ are not contemporaneously hydrogen; and obtainment of fluorohalogencarbons of formula: [in-line-formulae]FCY″Y—CY′ClF ??(III)[/in-line-formulae]wherein Y, Y′ and Y″ are as above; 2a) dehalogenation or dehydrohalogenation of the fluorohalogencarbons (III) and obtainment of fluorohalogen olefins of formula: [in-line-formulae]FCYI═CYIIF ??(IV)[/in-line-formulae]wherein YI and YII, equal to or different from each other, have the meaning of H, Cl, Br with the proviso that YI and YII are not both H; 3a) reaction between a hypofluorite of formula RfOF and a fluorohalogenolefin (IV), obtaining the fluorohalogenethers of formula: [in-line-formulae]RfO—CFYI—CF2YII ??(I)[/in-line-formulae]wherein YI, YII, equal to or different from each other, are Cl, Br, H with the proviso that YI and YII cannot be contemporaneously equal to H; 4a) dehalogenation or dehydrohalogenation of the compounds (I) and obtainment of the perfluorovinylethers (IA).

Process for preparing fluorohalogenethers

A process for preparing fluorovinylethers having general formula: ???????? RfO-CF=CF2,?????(IA) wherein Rf is a fluorinated or perfluorinated alkyl or cycloalkyl substituent; comprising the following reaction steps: 1) reaction of a hypofluorite of formula RfOF, wherein Rf is as above, with an olefin of formula: ???????? CY"Y=CY'Cl?????(II) wherein Y, Y' and Y", equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y' and Y" are not contemporaneously hydrogen; 2) dehalogenation or dehydrohalogenation of the fluorohalogenethers obtained in step 1) and obtainment of vinyl ethers of formula: ???????? RfO-CYI=CYIIF?????(IV) wherein YI and YII, equal to or different from each other, have the meaning of H, Cl, Br with the proviso that YI and YII are not both H; 3) fluorination with fluorine of the vinyl ethers (IV) and obtainment of fluorohalogenethers of formula: ???????? RfO-CFYI-CF2YII?????(I) wherein YI, YII, equal to or different from each other, are Cl, Br, H with the proviso that YI and YII cannot be contemporaneously equal to H; 4) dehalogenation or dehydrohalogenation of the fluorohalogenethers (I) and obtainment of the fluorovinylethers (IA).

Process for preparing fluorohalogenethers

A process for preparing fluorovinylethers having general formula: [in-line-formulae]RfO—CF═CF2 ??(IA)[/in-line-formulae]wherein Rf is a fluorinated or perfluorinated alkyl or cycloalkyl substituent; comprising the following reaction steps:1) reaction of a hypofluorite of formula RfOF, wherein Rf is as above, with an olefin of formula: [in-line-formulae]CY″Y═CY′CI ??(II)[/in-line-formulae]wherein Y, Y′ and Y″, equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y′ and Y″ are not contemporaneously hydrogen;2) dehalogenation or dehydrohalogenation of the fluorohalogenethers obtained in step 1) and obtainment of vinyl ethers of formula: [in-line-formulae]RfO—CYI═CYIIF ??(IV)[/in-line-formulae]wherein YI and YII, equal to or different from each other, have the meaning of H, Cl, Br with the proviso that YI and YII are not both H;3) fluorination with fluorine of the vinyl ethers (IV) and obtainment of fluorohalogenethers of formula: [in-line-formulae]RfO—CFYI—CF2YII ??(I)[/in-line-formulae]wherein YI, YII, equal to or different from each other, are Cl, Br, H with the proviso that YI and YII cannot be contemporaneously equal to H;4) dehalogenation or dehydrohalogenation of the fluorohalogenethers (I) and obtainment of the fluorovinylethers (IA).

TFE-based thermoprocessable copolymers

TFE-based thermoprocessable copolymers having the following composition, expressed in percentage by moles on the total of the monomers: A) from 0.01 to 15% of the monomer of formula: [in-line-formulae]CF2═CFOCF2OCF3??(a); [/in-line-formulae] A1) tetrafluoroethylene from 99.99 to 85%; optionally B) one or more (per)fluorinated comonomers having at least one unsaturation of ethylene type, different from TFE; the sum of the molar percentages A)+B) being such as to give polymers showing at least one melting peak at the thermogravimetric analysis (DSC).

Process for preparing fluorohalogenethers

A process for preparing (per)fluorohalogenethers having general formula (I): (R)nC(F)mOCAF—CA′F2??(I) wherein: A and A′, equal to or different the one from the other, are Cl or Br or one is selected from A and A′ and hydrogen and the other is halogen selected from Cl, Br; R═F, or a fluorinated, preferably perfluorinated, substituent, selected from the following groups: linear or branched C1-C20 alkyl more preferably C1-C10; C3-C7 cycloalkyl; aromatic, C6-C10 arylalkyl, alkylaryl; C5-C10 heterocyclic or alkylheterocyclic; when R is fluorinated or perfluorinated alkyl, cycloalkyl, arylalkyl, alkylaryl, it can optionally contain in the chain one or more oxygen atoms; when R is fluorinated it can optionally contain one or more H atoms and/or one or more halogen atoms different from F: n is an integer and is 1 or 2; m=3-n; by reaction of carbonyl compounds having formula (II): (R)pC(F)q(O)??(II) wherein: p is an integer and is 1 or 2; q is an integer and is zero or 1, R is as above; in liquid phase with elemental fluorine and with olefinic compounds having formula (III): CAF═CA′F??(III) wherein A and A′ are as above, at temperatures in the range from ?120° C. to ?20° C.

Process for preparing fluorohalogenethers

A process for preparing (per) fluorohalogenethers having general formula (I):(R)nC(F)mOCAF-CA'F2 wherein:A and A', equal to or different the one from the other, are Cl or Br or one is selected from A and A' and hydrogen and the other is halogen selected from Cl, Br; R = F, or a fluorinated, preferably perfluorinated, substituent, selected from the following groups: linear or branched C1-C20 alkyl more preferably C1-C10; C3-C7 cycloalkyl; aromatic, C6-C10 arylalkyl, alkylaryl; C5-C10 heterocyclic or alkylheterocyclic; when R is fluorinated or perfluorinated alkyl, cycloalkyl, arylalkyl, alkylaryl, it can optionally contain in the chain one or more oxygen atoms;when R is fluorinated it can optionally contain one or more H atoms and/or one or more halogen atoms different from F:n is an integer and is 1 or 2; m = 3-n; by reaction of carbonyl compounds having formula (II):(R)pC(F)q(O) wherein:p is an integer and is 1 or 2; q is an integer and is zero or 1, R is as above; in liquid phase with elemental fluorine and with olefinic compounds having formula (III):CAF=CA'F wherein A and A' are as above, at temperatures in the range from -120°C to -20°C.

Defluorination of homologous chlorofluoroethers to chlorofluoroacetates

The research was focused on the defluorination of chlorofluoroethers to corresponding esters using porous aluminum fluoride (PAF) or MFn/PAF. In the work up process, the product was easily separated from the reagent. Thus, the reaction would be a practical preparation method for polyfluorinated esters. Trifluoromethyl chlorodifluoroacetate was obtained by the reaction of 1,2-dichlorotrifluoroethyltrifluoromethyl ether with fuming sulfuric acid in 49% yield.