The object is to selectively separate a linear compound from a treatment subject containing linear and alicyclic compounds as double bond-containing hydrocarbon compounds in which every hydrogen is replaced with fluorine or chlorine. A method of separating a double bond-containing linear hydrocarbon in which every hydrogen is replaced with fluorine or chlorine includes bringing a treatment subject containing a double bond-containing linear hydrocarbon in which every hydrogen is replaced with fluorine or chlorine and a double bond-containing alicyclic hydrocarbon in which every hydrogen is replaced with fluorine or chlorine into contact with at least one amine compound selected from the group consisting of a heterocyclic aromatic amine compound and a tertiary amine represented by a formula: NR.sup.1R.sup.2R.sup.3 (R.sup.1, R.sup.2, and R.sup.3 are each independently an alkyl group, and two thereof may in combination form an alkylene group that is optionally interrupted by oxygen or sulfur).

The object is to selectively separate a linear compound from a treatment subject containing linear and alicyclic compounds as double bond-containing hydrocarbon compounds in which every hydrogen is replaced with fluorine or chlorine. A method of separating a double bond-containing linear hydrocarbon in which every hydrogen is replaced with fluorine or chlorine includes bringing a treatment subject containing a double bond-containing linear hydrocarbon in which every hydrogen is replaced with fluorine or chlorine and a double bond-containing alicyclic hydrocarbon in which every hydrogen is replaced with fluorine or chlorine into contact with at least one amine compound selected from the group consisting of a heterocyclic aromatic amine compound and a tertiary amine represented by a formula: NR.sup.1R.sup.2R.sup.3 (R.sup.1, R.sup.2, and R.sup.3 are each independently an alkyl group, and two thereof may in combination form an alkylene group that is optionally interrupted by oxygen or sulfur).

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).

##STR00001##

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).

##STR00001##

According to a method for producing a perfluoroalkadiene compound represented by general formula (1): CF.sub.2═CF—(CF.sub.2).sub.n-4—CF═CF.sub.2 (1), wherein n is an integer of 4 or more, the method comprising a reaction step of adding a nitrogen-containing compound to a solution of a compound represented by general formula (2): X.sup.1CF.sub.2—CFX.sup.2—(CF.sub.2).sub.n-4—CF.sub.2—CF.sub.2X.sup.1 (2), wherein n is the same as above, X.sup.1 is the same or different and is a halogen atom other than fluorine, and X.sup.2 is a halogen atom, the perfluoroalkadiene compound can be obtained at a high yield.

According to a method for producing a perfluoroalkadiene compound represented by general formula (1): CF.sub.2═CF—(CF.sub.2).sub.n-4—CF═CF.sub.2 (1), wherein n is an integer of 4 or more, the method comprising a reaction step of adding a nitrogen-containing compound to a solution of a compound represented by general formula (2): X.sup.1CF.sub.2—CFX.sup.2—(CF.sub.2).sub.n-4—CF.sub.2—CF.sub.2X.sup.1 (2), wherein n is the same as above, X.sup.1 is the same or different and is a halogen atom other than fluorine, and X.sup.2 is a halogen atom, the perfluoroalkadiene compound can be obtained at a high yield.

According to a method for producing a perfluoroalkadiene compound represented by general formula (1): CF.sub.2═CF—(CF.sub.2).sub.n-4—CF═CF.sub.2 (1), wherein n is an integer of 4 or more, the method comprising a reaction step of adding a nitrogen-containing compound to a solution of a compound represented by general formula (2): X.sup.1CF.sub.2—CFX.sup.2—(CF.sub.2).sub.n-4—CF.sub.2—CF.sub.2X.sup.1 (2), wherein n is the same as above, X.sup.1 is the same or different and is a halogen atom other than fluorine, and X.sup.2 is a halogen atom, the perfluoroalkadiene compound can be obtained at a high yield.

Provided is a method for producing hexafluoro-1,3-butadiene, and the method can produce hexafluoro-1,3-butadiene at an industrially sufficient level of yield. In a reaction liquid containing a halogenated butane represented by chemical formula, CF.sub.2X.sup.1—CFX.sup.2—CFX.sup.3—CF.sub.2X.sup.4 (X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently a halogen atom other than a fluorine atom), zinc, and an organic solvent, a reaction is conducted to eliminate the halogen atoms other than a fluorine atom, X.sup.1, X.sup.2, X.sup.3, and X.sup.4, from the halogenated butane, yielding hexafluoro-1,3-butadiene. During the reaction, the concentration of a zinc halide generated by the reaction, in the reaction liquid is not more than the solubility of the zinc halide in the organic solvent.

Provided is a method for producing hexafluoro-1,3-butadiene, and the method can produce hexafluoro-1,3-butadiene at an industrially sufficient level of yield. In a reaction liquid containing a halogenated butane represented by chemical formula, CF.sub.2X.sup.1—CFX.sup.2—CFX.sup.3—CF.sub.2X.sup.4 (X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently a halogen atom other than a fluorine atom), zinc, and an organic solvent, a reaction is conducted to eliminate the halogen atoms other than a fluorine atom, X.sup.1, X.sup.2, X.sup.3, and X.sup.4, from the halogenated butane, yielding hexafluoro-1,3-butadiene. During the reaction, the concentration of a zinc halide generated by the reaction, in the reaction liquid is not more than the solubility of the zinc halide in the organic solvent.

Provided is a method for producing hexafluoro-1,3-butadiene, and the method can produce hexafluoro-1,3-butadiene at an industrially sufficient level of yield. In a reaction liquid containing a halogenated butane represented by chemical formula, CF.sub.2X.sup.1—CFX.sup.2—CFX.sup.3—CF.sub.2X.sup.4 (X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently a halogen atom other than a fluorine atom), zinc, and an organic solvent, a reaction is conducted to eliminate the halogen atoms other than a fluorine atom, X.sup.1, X.sup.2, X.sup.3, and X.sup.4, from the halogenated butane, yielding hexafluoro-1,3-butadiene. During the reaction, the concentration of a zinc halide generated by the reaction, in the reaction liquid is not more than the solubility of the zinc halide in the organic solvent.