Problem to be Solved

It is intended to provide an industrially preferable fluoroalkylating agent and use thereof.

Solution

The present invention provides a fluoroalkylating agent represented by the general formula (1) wherein R.sup.1 is a C1 to C8 fluoroalkyl group; R.sup.2 and R.sup.3 are each independently a C1 to C12 alkyl group or the like; Y.sup.1 to Y.sup.4 are each independently a hydrogen atom, a halogen atom, or the like; and X.sup. is a monovalent anion.

##STR00001##

A compound of the general formula (3): R.sup.4SR.sup.1 having an introduced C1 to C8 fluoroalkyl group is easily obtained by reacting a compound of the general formula (2): R.sup.4SZ wherein R.sup.4 is a hydrocarbon group or the like; and Z is a leaving group, with the compound of the general formula (1).

Disclosed is a method for producing a hexafluoroisopropanol, including the steps of (a) purifying a mixture containing hexafluoroacetone and at least 1,1,1-trifluoro-2,2-dichloroethane as an impurity, thereby obtaining a purified hexafluoroacetone containing 120 ppm or lower of the 1,1,1-trifluoro-2,2-dichloroethane; and (b) bringing hydrogen (H.sub.2) into contact with the purified hexafluoroacetone in the presence of a catalyst, thereby hydrogenating the hexafluoroacetone into the hexafluoroisopropanol. It is possible by this method to produce the hexafluoroisopropanol with a short reaction time and a high conversion. Therefore, it is possible to particularly advantageously produce fluoromethyl hexafluoroisopropyl ether (sevoflurane) by using the hexafluoroisopropanol produced by the method.

Disclosed is a method for producing a hexafluoroisopropanol, including the steps of (a) purifying a mixture containing hexafluoroacetone and at least 1,1,1-trifluoro-2,2-dichloroethane as an impurity, thereby obtaining a purified hexafluoroacetone containing 120 ppm or lower of the 1,1,1-trifluoro-2,2-dichloroethane; and (b) bringing hydrogen (H.sub.2) into contact with the purified hexafluoroacetone in the presence of a catalyst, thereby hydrogenating the hexafluoroacetone into the hexafluoroisopropanol. It is possible by this method to produce the hexafluoroisopropanol with a short reaction time and a high conversion. Therefore, it is possible to particularly advantageously produce fluoromethyl hexafluoroisopropyl ether (sevoflurane) by using the hexafluoroisopropanol produced by the method.

A compound represented by general formula: R.sup.1R.sup.2X, wherein R.sup.1 is CH.sub.3, CH.sub.2F, CHF.sub.2, CH.sub.2I, CHFI, or an anionic group, R.sup.2 is an alkylene group consisting of unit represented by CFH, or an alkylene group consisting of unit represented by CFH and a unit represented by CH.sub.2, provided that these alkylene groups optionally contain epoxy group, CH(OH), CHI, or a divalent cycloalkylene group, X is OH, CH(R.sup.21)OH (wherein R.sup.21 is H, a non-fluorinated alkyl group, or a fluorinated alkyl group), I, CFHI, CH.sub.2I, an anionic group, or COOR.sup.22 (wherein R.sup.22 is a non-fluorinated alkyl group having 1 to 8 carbon atoms, and the total number of carbon atoms of R.sup.1, R.sup.2, and X is 2 to 50).

A compound represented by general formula: R.sup.1R.sup.2X, wherein R.sup.1 is CH.sub.3, CH.sub.2F, CHF.sub.2, CH.sub.2I, CHFI, or an anionic group, R.sup.2 is an alkylene group consisting of unit represented by CFH, or an alkylene group consisting of unit represented by CFH and a unit represented by CH.sub.2, provided that these alkylene groups optionally contain epoxy group, CH(OH), CHI, or a divalent cycloalkylene group, X is OH, CH(R.sup.21)OH (wherein R.sup.21 is H, a non-fluorinated alkyl group, or a fluorinated alkyl group), I, CFHI, CH.sub.2I, an anionic group, or COOR.sup.22 (wherein R.sup.22 is a non-fluorinated alkyl group having 1 to 8 carbon atoms, and the total number of carbon atoms of R.sup.1, R.sup.2, and X is 2 to 50).

A method is disclosed for producing polyfluorinated alcohols of formula (I)

##STR00001##

starting from a ketone of formula (II),

##STR00002##

and a carboxylic acid salt of formula (III) (R.sup.3COO).sub.xY. The substituents R.sup.1 and R.sup.2 can be selected from C.sub.1-C.sub.10 alkyl, C.sub.3-C.sub.10 cycloalkyl, C.sub.6-C.sub.14 aryl, and C.sub.5-C.sub.14 heteroaryl. The substituents may be unsubstituted or partially or completely fluorinated. R.sup.3 is a partially or completely fluorinated C.sub.1-C.sub.10 alkyl, Y is a cation of K, Li, Na, Cs, Mg, Ca, Fe, Cu, Ag, and Zn, and x is 1 or 2. In the method, the R.sup.3 group of the carboxylic acid salt is transferred to the carbonyl carbon of the ketone of formula (II) with the release of CO.sub.2.

A method is disclosed for producing polyfluorinated alcohols of formula (I)

##STR00001##

starting from a ketone of formula (II),

##STR00002##

and a carboxylic acid salt of formula (III) (R.sup.3COO).sub.xY. The substituents R.sup.1 and R.sup.2 can be selected from C.sub.1-C.sub.10 alkyl, C.sub.3-C.sub.10 cycloalkyl, C.sub.6-C.sub.14 aryl, and C.sub.5-C.sub.14 heteroaryl. The substituents may be unsubstituted or partially or completely fluorinated. R.sup.3 is a partially or completely fluorinated C.sub.1-C.sub.10 alkyl, Y is a cation of K, Li, Na, Cs, Mg, Ca, Fe, Cu, Ag, and Zn, and x is 1 or 2. In the method, the R.sup.3 group of the carboxylic acid salt is transferred to the carbonyl carbon of the ketone of formula (II) with the release of CO.sub.2.

According to an embodiment, a method for producing a (hydro)halocarbon includes a step of purifying the (hydro)halocarbon by reduced-pressure distillation of an azeotropic or azeotropic-like composition containing the (hydro)halocarbon and a compound different from the (hydro)halocarbon. According to another embodiment, a method for producing a (hydro)halocarbon includes a step purifying the (hydro)halocarbon by reduced-pressure distillation of an azeotropic or azeotropic-like composition containing the (hydro)halocarbon and a compound different from the (hydro)halocarbon, wherein standard boiling points of both the (hydro)halocarbon and the compound are 80 C. or lower.

According to an embodiment, a method for producing a (hydro)halocarbon includes a step of purifying the (hydro)halocarbon by reduced-pressure distillation of an azeotropic or azeotropic-like composition containing the (hydro)halocarbon and a compound different from the (hydro)halocarbon. According to another embodiment, a method for producing a (hydro)halocarbon includes a step purifying the (hydro)halocarbon by reduced-pressure distillation of an azeotropic or azeotropic-like composition containing the (hydro)halocarbon and a compound different from the (hydro)halocarbon, wherein standard boiling points of both the (hydro)halocarbon and the compound are 80 C. or lower.

An object of the present disclosure is to provide a method for producing an organic compound, and a composition. The object is achieved by a method for producing a compound represented by formula (1): ##STR00001## wherein X represents O, an optionally substituted imino group, or S, R.sup.1 represents a hydrogen atom or a hydrocarbyl group optionally having at least one substituent, and R.sup.2 represents a hydrogen atom or a monovalent organic group, or R.sup.1 and R.sup.2, together with X and one carbon atom respectively adjacent to R.sup.1 and R.sup.2, may form a heterocyclic ring optionally having at least one substituent, R.sup.3 represents a hydrogen atom or a monovalent organic group, and R.sup.4 represents CF.sub.2CH.sub.3 or CH.sub.2CHF.sub.2; the method including step A of reacting a compound represented by formula (2): ##STR00002## wherein the alphabetical symbols are as defined above, with vinylidene fluoride under light irradiation.