Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/12—Saturated ethers containing halogen
  • C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/12—Saturated ethers containing halogen
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
  • C09K5/02—Materials undergoing a change of physical state when used
  • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
  • C09K5/08—Materials not undergoing a change of physical state when used
  • C09K5/10—Liquid materials
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/22—Organic compounds
  • C11D7/28—Organic compounds containing halogen
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5004—Organic solvents
  • C11D7/5018—Halogenated solvents

Definitions

• This disclosure relates to a fluorine-containing ether compound and a method for producing the same.
• Fluorinated ethers are not only used as solvents, but also for a wide range of other purposes.
• Patent Document 2 describes a hydrofluoroether compound that contains two terminal fluorinated alkyl groups and a substituted or unsubstituted oxymethylene group interposed in the chain, each of the fluorinated alkyl groups containing only one hydrogen atom, and optionally containing at least one in-chain heteroatom, with the proviso that the hydrogen atom is part of a monofluoromethylene moiety.
• Patent Documents 1 and 2 describe that at least one of the two groups bonded to the oxygen of an ether compound is composed of a perfluoroaliphatic group, and at least one of the groups is composed of a fluorinated alkyl group containing only one hydrogen atom.
• the objective of this disclosure is to provide a fluorine-containing ether compound in which at least one of the two groups bonded to the oxygen of the ether compound is a group that does not contain a trifluoromethyl group or a difluoromethylene group.
• R 1 -R 2 -O-R 3 -R 4 (Wherein, R 1 is -CH 3 , -CH 2 F, -CHF 2 , -CH 2 I or -CHFI; R 2 is a fluorinated alkylene group having 1 to 10 carbon atoms and consisting only of units represented by -CHF-, or a fluorinated alkylene group having 2 to 10 carbon atoms and consisting only of units represented by -CHF- and units represented by -CH 2 -, or a fluorinated alkylene group having 3 to 10 carbon atoms and consisting only of units represented by -CFH-, units represented by -CH 2 - and units represented by -CHI-, R3 is a single bond, a non-fluorinated alkylene group having 1 to 5 carbon atoms, or a fluorinated alkylene group having 1 to 10 carbon atoms; R4 is -CH3 ,
• a fluorine-containing ether compound in which at least one of the two groups bonded to the oxygen of the ether compound is a group that does not contain a trifluoromethyl group or a difluoromethylene group.
• the fluorine-containing ether compound of the present disclosure has the general formula: R 1 -R 2 -O-R 3 -R 4 (In the formula, R 1 is -CH 3 , -CH 2 F, -CHF 2 , -CH 2 I or -CHFI; R 2 is a fluorinated alkylene group having 1 to 10 carbon atoms composed only of units represented by -CHF-, or a fluorinated alkylene group having 2 to 10 carbon atoms composed only of units represented by -CHF- and units represented by -CH 2 -, or a fluorinated alkylene group having 3 to 10 carbon atoms composed only of units represented by -CFH-, units represented by -CH 2 - and units represented by -CHI-; R 3 is a single bond, a non-fluorinated alkylene group having 1 to 5 carbon atoms or a fluorinated alkylene group having 1 to 10 carbon atoms; and R 4 is -CH 3 ,
• R 1 is -CH 3 , -CH 2 F, -CHF 2 , -CH 2 I or -CHFI, preferably -CH 2 F, -CHF 2 or -CHFI, more preferably -CH 2 F.
• One feature of the fluorine-containing ether compound of the present disclosure is that at least one of the two groups bonded to oxygen of the ether compound does not have a CF 3 - (trifluoromethyl group) at its terminal.
• R2 is a fluorinated alkylene group having 1 to 10 carbon atoms composed only of units represented by -CHF-, or a fluorinated alkylene group having 2 to 10 carbon atoms composed only of units represented by -CHF- and units represented by -CH 2 -, or a fluorinated alkylene group having 3 to 10 carbon atoms composed only of units represented by -CFH-, units represented by -CH 2 - and units represented by -CHI-.
• One feature of the fluorinated ether compound of the present disclosure is that at least one of the two groups bonded to oxygen of the ether compound necessarily contains a unit represented by -CHF- and does not contain a unit represented by -CF 2 -.
• R 2 is a fluorinated alkylene group composed only of units represented by -CHF-
• R 2 is preferably, for example, a fluorinated alkylene group represented by -(CHF) n1 - (n1 is an integer of 1 to 10).
• R 2 is a fluorinated alkylene group composed only of units represented by -CHF- and units represented by -CH 2 -
• examples of R 2 include fluorinated alkylene groups represented by -CHF-(CHF-CHF) n2 -(CH 2 ) m1 - (n2 is an integer of 1 to 4, m1 is an integer of 1 or more) and fluorinated alkylene groups represented by -(CHF) n7 -CH 2 -CH 2 -(CH 2 ) q - (wherein n7 is an integer of 1 to 7, and q is an integer of 1 to 6).
• R 2 is a fluorinated alkylene group composed only of units represented by -CHF- and units represented by -CH 2 -
• R 2 is preferably a fluorinated alkylene group represented by -(CHF) n2 -CH 2 - (n2 is an integer of 1 to 9) or a fluorinated alkylene group represented by -(CHF) n7 -CH 2 -CH 2 -(CH 2 ) q - (wherein n7 is an integer of 1 to 7, and q is an integer of 1 to 6), and more preferably a fluorinated alkylene group represented by -CHF-(CHF-CHF) n3 -CH 2 - (n3 is an integer of 0 to 4) or -CHF-(CHF-CHF) n8 -CH 2 -CH 2 -(CH 2 ) q - (wherein n8 is an integer of 0 to 2, and q is an integer of 1 to 6).
• R 2 is an alkylene group composed only of units represented by -CFH-, units represented by -CH 2 - and units represented by -CHI-
• R 2 is preferably a fluorinated alkylene group represented by -(CHF) n7 -CH 2 -CHI-(CH 2 ) q - (wherein n7 is an integer from 1 to 7, and q is an integer from 1 to 6), and more preferably a fluorinated alkylene group represented by -CHF-(CHF-CHF) n8 -CH 2 -CHI-(CH 2 ) q - (wherein n8 is an integer from 0 to 2, and q is an integer from 1 to 6).
• the group represented by R 1 -R 2 - is CH 2 F-CHF- or a fluorinated alkyl group represented by the general formula: CH 2 F-CHF-(CHF-CHF) n3 -CH 2 - (wherein n3 is an integer of 0 to 4);
• n3 is preferably 0 or 1.
• R 3 is a single bond, a non-fluorinated alkylene group having 1 to 5 carbon atoms, or a fluorinated alkylene group having 1 to 10 carbon atoms.
• the number of carbon atoms in R 3 is preferably 0 to 5, more preferably 0 to 3, and even more preferably 0 or 1.
• the number of carbon atoms in the non-fluorinated alkylene group of R 3 is preferably 1 or 2.
• the number of carbon atoms in the fluorinated alkylene group of R 3 is preferably 1 to 5, and more preferably 1 or 2.
• R 3 is preferably a single bond, a non-fluorinated alkylene group having 1 to 5 carbon atoms, a fluorinated alkylene group represented by -(CHF) n4 - (wherein n4 is an integer of 1 to 10), or a fluorinated alkylene group represented by -(CHF) n5 -CH 2 - (wherein n5 is an integer of 1 to 9).
• R4 is -CH3 , -CH2F or -CHF2 , with -CH3 or -CH2F being preferred.
• the group represented by R 4 -R 3 - is a non-fluorinated alkyl group having 1 to 4 carbon atoms, or a group represented by the general formula: CH2F -CHF-(CHF-CHF) n6 - CH2- (wherein n6 is an integer of 0 to 4) is preferred.
• the non-fluorinated alkyl group preferably has 1 or 2 carbon atoms.
• n6 is preferably 0 or 1.
• fluorine-containing ether compound examples include CH 2 FCHFOCH 3 , CH 2 FCHFCH 2 OCH 3 , CH 2 FCHFCH 2 OCHFCFH 2 , CH 2 FCHFCH 2 OCH 2 CH 3 , CH 2 FCHFCHFCHFCH 2 OCH 3 , CHF 2 -CHF-CH 2 -CHI-CH 2 -OCH 3 , CHF 2 -CHF-CH 2 -CH 2 -CH 2 -OCH 3 , CHF 2 -CHF-CH 2 -CH 2 -OCHFCFH 2 , CHF 2 -CHF-CH 2 -CH 2 -CH 2 -OCH 2 CH 3 , CHF 2 -CHF-CH 2 -CHI-CH 2 -CH 2 At least one selected from the group consisting of -CH 2 -CH 2 -OCH 3 and CHF 2 -CHF-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -OCH 3 is
• the fluorine-containing ether compound of the present disclosure can be produced, for example, by a production method for producing a fluorine-containing ether compound represented by the general formula CH 2 F-CHF-O-R 3 -R 4 (wherein R 3 and R 4 are as defined above) by reacting CHF ⁇ CHF with an alcohol represented by the general formula R 4 -R 3 -OH (wherein R 3 and R 4 are as defined above) in the presence of a basic compound (hereinafter, this method may be referred to as the first production method).
• a production method for producing a fluorine-containing ether compound represented by the general formula CH 2 F-CHF-O-R 3 -R 4 (wherein R 3 and R 4 are as defined above) by reacting CHF ⁇ CHF with an alcohol represented by the general formula R 4 -R 3 -OH (wherein R 3 and R 4 are as defined above) in the presence of a basic compound hereinafter, this method may be referred to as the first production method.
• the basic compound acts as a catalyst.
• the basic compound is preferably an inorganic basic compound, more preferably an alkali metal hydroxide or an alkaline earth metal hydroxide such as NaOH, KOH, CsOH, LiOH, Ca(OH) 2 , or Ba(OH) 2 .
• the amount of the basic compound used is preferably 0.01 to 1.0 moles, and more preferably 0.2 to 0.8 moles, per mole of alcohol.
• the solvent include polar organic solvents such as water, diethyl ether, glymes, dioxane, tetrahydrofuran, and acetonitrile.
• the present invention can be produced by a production method (hereinafter sometimes referred to as the second production method) in which a fluorinated ether compound represented by the general formula: CH 2 F- CHF- (CHF- CHF ) n3 -CH 2 -O -R 3 -R 4 (wherein n3, R 3 and R 4 are as defined above) is produced by reacting a fluorinated alcohol with a compound represented by R 4 -R 3 -X (wherein R 3 and R 4 are as defined above, and X is a halogen atom or -OSO 3 R' (wherein R' is a non-fluorinated alkyl group or
• n3 is an integer from 0 to 4, preferably 0 or 1.
• organic peroxides are preferred, and examples thereof include dialkyl peroxycarbonates such as diisopropyl peroxydicarbonate and disec-butyl peroxydicarbonate, peroxyesters such as 2-ethylhexanoyl (tert-butyl) peroxide, t-butyl peroxyisobutyrate and t-butyl peroxypivalate, and dialkyl peroxides such as di-t-butyl peroxide. Of these, di-t-butyl peroxide is the most preferred radical initiator.
• the amount of radical initiator used is preferably 0.01 to 2 moles per mole of methanol.
• the resulting fluorine-containing alcohol is then reacted with a compound represented by R 4 -R 3 -X to alkylate the oxygen of the fluorine-containing alcohol to produce a fluorine-containing ether compound.
• a fluorine-containing ether compound can be produced by reacting a fluorine-containing alcohol with a base such as sodium hydride and reacting the resulting fluorine-containing alkoxide with a compound represented by R 4 -R 3 -X (X is a halogen atom).
• a fluorinated ether compound can be produced, for example, by reacting a fluorinated alcohol with a compound represented by R4 - R3 -X (X is -OSO3R ') in an aqueous hydroxide solution.
• R 4 —R 3 —X (X is —OSO 3 R′) is preferably (R 4 —R 3 —O—) 2 SO 2 (R 3 and R 4 are as defined above).
• the pressure of the reaction between the fluorine-containing alcohol and the compound represented by R 4 -R 3 -X is preferably 0.1 to 2.0 MPaG.
• the temperature of the reaction between the fluorine-containing alcohol and the compound represented by R 4 -R 3 -X is preferably 20 to 95°C.
• n8 is 1 or 2, preferably 1.
• a radical initiator include organic peroxides and azo compounds.
• organic peroxides examples include dialkyl peroxycarbonates such as diisopropyl peroxydicarbonate and disec-butyl peroxydicarbonate, peroxyesters such as 2-ethylhexanoyl (tert-butyl) peroxide, t-butyl peroxyisobutyrate and t-butyl peroxypivalate, and dialkyl peroxides such as di-t-butyl peroxide.
• dialkyl peroxycarbonates such as diisopropyl peroxydicarbonate and disec-butyl peroxydicarbonate
• peroxyesters such as 2-ethylhexanoyl (tert-butyl) peroxide
• t-butyl peroxyisobutyrate examples of organic peroxides
• dialkyl peroxides such as di-t-butyl peroxide.
• azo compounds examples include azobisisobutyronitrile.
• the amount of radical initiator used is preferably 0.01 to 2 moles per mole of fluorine-containing alkyl iodide.
• the first or second fluorine-containing alkyl iodide is then reacted with an unsaturated compound represented by the general formula: CH 2 ⁇ CH-(CH 2 ) q -OH (wherein q is an integer of 1 or more) to produce a fluorine-containing alcohol represented by the general formula: R 1 -CHF-(CHF-CHF) n8 -CH 2 -CHI-(CH 2 ) q -OH (wherein R 1 is as defined above, n8 is an integer of 0 to 2, and q is an integer of 1 to 6).
• R 1 of the fluorine-containing alcohol is the same as R 1 of the first or second fluorine-containing alkyl iodide, and is —CHF2 or —CHFI.
• n8 of the fluorine-containing alcohol is an integer from 0 to 2, preferably 0 or 1.
• the reaction between the first or second fluorine-containing alkyl iodide and the unsaturated compound can be carried out in the presence of a compound that generates radicals.
• a compound that generates radicals examples include organic peroxides and azo compounds.
• organic peroxides examples include dialkyl peroxycarbonates such as diisopropyl peroxydicarbonate and disec-butyl peroxydicarbonate, peroxyesters such as 2-ethylhexanoyl (tert-butyl) peroxide, t-butyl peroxyisobutyrate and t-butyl peroxypivalate, and dialkyl peroxides such as di-t-butyl peroxide.
• dialkyl peroxycarbonates such as diisopropyl peroxydicarbonate and disec-butyl peroxydicarbonate
• peroxyesters such as 2-ethylhexanoyl (tert-butyl) peroxide
• t-butyl peroxyisobutyrate examples of organic peroxides
• dialkyl peroxides such as di-t-butyl peroxide.
• azo compounds examples include azobisisobutyronitrile.
• the amount of the unsaturated compound used is preferably 0.01 to 100 moles per mole of the first or second fluorine-containing alkyl iodide.
• the amount of the radical-generating compound used is preferably 0.001 to 1 mole per mole of the first or second fluorine-containing alkyl iodide.
• the temperature for the reaction between the first or second fluorine-containing alkyl iodide and the unsaturated compound can be selected as appropriate, but is preferably 50 to 200°C.
• the pressure for the reaction between the first or second fluorine-containing alkyl iodide and the unsaturated compound can be selected as appropriate, but is preferably 0.1 to 5 MPaG.
• the time for the reaction between the first or second fluorine-containing alkyl iodide and the unsaturated compound can be selected as appropriate, but is preferably 0.1 to 96 hours.
• the resulting fluorine-containing alcohol is then reacted with a compound represented by R 4 -R 3 -X to alkylate the oxygen of the fluorine-containing alcohol to produce a fluorine-containing ether compound.
• a fluorine-containing ether compound can be produced by reacting a fluorine-containing alcohol with a base such as sodium hydride and reacting the resulting fluorine-containing alkoxide with a compound represented by R 4 -R 3 -X (X is a halogen atom).
• a fluorinated ether compound can be produced, for example, by reacting a fluorinated alcohol with a compound represented by R4 - R3 -X (X is -OSO3R ') in an aqueous hydroxide solution.
• R 4 —R 3 —X (X is —OSO 3 R′) is preferably (R 4 —R 3 —O—) 2 SO 2 (R 3 and R 4 are as defined above).
• the pressure of the reaction between the fluorine-containing alcohol and the compound represented by R 4 -R 3 -X is preferably 0.1 to 2.0 MPaG.
• the temperature of the reaction between the fluorine-containing alcohol and the compound represented by R 4 -R 3 -X is preferably 20 to 95°C.
• the first fluorine-containing alcohol may be reduced to the second fluorine-containing alcohol.
• the reduction can be carried out, for example, by using a metal catalyst and hydrogen, or by using zinc as a reducing agent.
• the first or second fluorine-containing alkyl iodide can be reacted with an unsaturated compound represented by the general formula: CH 2 ⁇ CH-(CH 2 ) q -O-R 3 -R 4 (wherein q is an integer of 1 or more, and R 3 and R 4 are as defined above for R 3
• the methods for producing the first and second fluorine-containing alkyl iodides are as described in the third production method.
• the reaction between the first or second fluorine-containing alkyl iodide and the unsaturated compound represented by the general formula: CH 2 ⁇ CH-(CH 2 ) q -O-R 3 -R 4 can be carried out in the same manner as the reaction between the first or second fluorine-containing alkyl iodide and the unsaturated compound represented by the general formula: CH 2 ⁇ CH-(CH 2 ) q -OH explained in the third production method.
• the obtained fluorine-containing ether compound may be reduced to produce a fluorine-containing ether compound represented by the general formula: R 1 -CHF-(CHF-CHF) n8 -CH 2 -CH 2 -(CH 2 ) q -O-R 3 -R 4 (wherein R 1 , R 3 and R 4 are as defined above, n8 is an integer of 0 to 2, and q is an integer of 1 to 6).
• the reduction can be carried out, for example, using a metal catalyst and hydrogen, or using zinc as a reducing agent.
• the composition of the present disclosure may contain the above-mentioned fluorine-containing ether compound and a solvent.
• the solvent may be at least one selected from the group consisting of alcohols, ethers, alkanes, alkenes, perfluorinated carbons, perfluorinated tertiary amines, perfluorinated ethers, cycloalkanes, esters, ketones, aromatic compounds, siloxanes, hydrochlorocarbons, hydrochlorofluorocarbons, and hydrofluorocarbons.
• composition of the present disclosure may also contain the above-mentioned fluorine-containing ether compound and other components such as surfactants, stabilizers, pigments, dyes, colorants, antioxidants, and flame retardants.
• composition of the present disclosure may contain the above-mentioned fluorine-containing ether compound, as well as other fluorine-containing ether compounds different from the above-mentioned fluorine-containing ether compounds.
• fluorine-containing ether compounds include hydrofluoroether compounds.
• the fluorine-containing ether compounds and compositions disclosed herein can be suitably used as heat transfer fluids, cleaning solvents, bubble size regulators for adjusting the bubble size of foam insulation materials, fire extinguishing agents, carrier fluids, working fluids, polymerization solvents, abrasives, drying agents, resist spreaders, resist strippers, etc.
• they can be used for the applications of hydrofluoroether compounds described in JP-A-2009-507840.
• R 1 -R 2 -O-R 3 -R 4 (Wherein, R 1 is -CH 3 , -CH 2 F, -CHF 2 , -CH 2 I or -CHFI; R 2 is a fluorinated alkylene group having 1 to 10 carbon atoms and consisting only of units represented by -CHF-, or a fluorinated alkylene group having 2 to 10 carbon atoms and consisting only of units represented by -CHF- and units represented by -CH 2 -, or a fluorinated alkylene group having 3 to 10 carbon atoms and consisting only of units represented by -CFH-, units represented by -CH 2 - and units represented by -CHI-, R3 is a single bond, a non-fluorinated alkylene group having 1 to 5 carbon atoms, or a fluorinated alkylene group having 1 to 10 carbon atoms; R4 is -CHCH 3 , -CH 2 F, -CHF 2 ,
• the present invention provides a fluorine-containing ether compound represented by the following formula: ⁇ 2> According to a second aspect of the present disclosure, there is provided a fluorine-containing ether compound according to a first aspect, in which R 1 is —CH 2 F, —CHF 2 or —CHFI.
• R2 is General formula: -(CHF) n1 - (wherein n1 is an integer from 1 to 10) or a fluorinated alkylene group represented by General formula: -(CHF) n2 -CH 2 - (wherein n2 is an integer from 1 to 9) or a fluorinated alkylene group represented by a fluorinated alkylene group represented by -(CHF) n7 -CH 2 -CH 2 -(CH 2 ) q - (wherein n7 is an integer of 1 to 7, and q is an integer of 1 to 6), or
• a fluorinated ether compound according to the first or second aspect which is a fluorinated alkylene group represented by the formula -(CHF) n7 -CH 2 -CHI-(CH 2 ) q - (wherein n7 is an integer of 1 to 7, and q is an integer of 1 to 6).
• R 1 -R 2 - is CH2F -CHF-, or General formula: a fluorinated alkyl group represented by the formula CH 2 F-CHF-(CHF-CHF) n3 -CH 2 - (wherein n3 is an integer of 0 to 4), or General formula: There is provided a fluorinated alkyl group represented by the formula: CHF 2 -CHF-(CHF-CHF) n8 -CH 2 -CHX 11 -(CH 2 ) q - (wherein n8 is an integer of 0 to 2, X 11 is I or H, and q is an integer of 1 to 6).
• R3 is a single bond, a non-fluorinated alkylene group having 1 to 5 carbon atoms, General formula: -(CHF) n4 - (wherein n4 is an integer from 1 to 10) or a fluorinated alkylene group represented by General formula: -(CHF) n5 -CH 2 - (wherein n5 is an integer from 1 to 9)
• the present invention provides a fluorine-containing ether compound according to any one of the first to fourth aspects, in which the fluorinated alkylene group is represented by ⁇ 6>
• R 4 -R 3 - is a non-fluorinated alkyl group having 1 to 4 carbon atoms, or General formula: CH 2 F—CHF—(CHF—CHF) n6 —CH 2 — (wherein n6 is an integer from 0 to 4)
• a fluorine-containing ether compound according to any one of the first to fourth aspects, in which the fluorinated alkylene
• a fluorine-containing ether compound according to any one of the first to seventh aspects, and there is provided a composition containing at least one selected from the group consisting of alcohols, ethers, alkanes, alkenes, perfluorinated carbons, perfluorinated tertiary amines, perfluorinated ethers, cycloalkanes, esters, ketones, aromatic compounds, siloxanes, hydrochlorocarbons, hydrochlorofluorocarbons, and hydrofluorocarbons.
• a heat transfer fluid containing the fluorinated ether compound according to any one of the first to seventh aspects or the composition according to the eighth aspect.
• a cleaning solvent containing the fluorinated ether compound according to any one of the first to seventh aspects or the composition according to the eighth aspect.
• Example 1 Synthesis of 1,1,2-trifluoro-2-iodoethane 37.1 g of iodine and 16.1 g of IF5 were added to a 300 mL pressure vessel, and the vessel was sealed. After cooling the vessel to -78°C, 10 g of (E)-1,2-difluoroethene was introduced into the vessel, and the vessel was heated at 80°C for 20 hours. After cooling the vessel with ice water, the contents of the pressure vessel were washed with water and then further washed with a 5% Na2S2O4 aqueous solution , to obtain 5.8 g of the title compound.
• Example 2 Synthesis of 4,5,5-trifluoro-2-iodopentanol 1.84 g of 1,1,2-trifluoro-2-iodoethane, 509 mg of allyl alcohol, and 288 mg of azobisisobutyronitrile were placed in a 10 mL pressure vessel. The vessel was then heated at 80° C. for 22 hours. After cooling the vessel with ice water, the contents of the pressure vessel were analyzed by gas chromatography-mass spectrometry. It was found that the title compound was produced in an area ratio of 75.9% compared to an area ratio of 24.1% for the raw material 1,1,2-trifluoro-2-iodoethane. LRMS (EI 70 eV) m/z (%): 268 (M+, 1), 251 (1), 185 (2), 141 (95), 73 (100), 51 (38).
• Example 3 Synthesis of 1,1,2-trifluoro-4-iodo-8-methoxyoctane 500 mg of 1,1,2-trifluoro-2-iodoethane, 272 mg of 6-methoxyhexene, and 117 mg of azobisisobutyronitrile were placed in a 10 mL pressure vessel. The vessel was cooled to -78°C, substituted with nitrogen, and then charged with nitrogen up to 0.5 MPa. The vessel was heated at 80°C for 13 hours. After cooling the vessel with ice water, a mixture containing the target compound was obtained.

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