The invention relates to a use of a fluorination gas, and the elemental fluorine (F.sub.2) is present in a high concentration, for example, in a concentration of elemental fluorine (F.sub.2), especially of equal to much higher than 15 or even 20% by volume, and to a process for the manufacture of a fluorinated compound by direct fluorination employing a fluorination gas, wherein the elemental fluorine (F.sub.2) is present in a high concentration. The process of the invention is directed to the manufacture of a fluorinated compound, for the exception of fluorinated benzene, by direct fluorination. Especially the invention is of interest in the preparation of fluorinated organic compounds, final products and as well intermediates, for usage in agro-, pharma-, electronics-, catalyst, solvent and other functional chemical applications. The fluorination process of the invention may be performed batch-wise or in a continuous manner.

The present disclosure provides, for example, a method that can produce a fluorolactone compound from hexafluoropropylene oxide or the like in a single step. The present disclosure relates to a method for producing a compound represented by formula (1):

##STR00001##

wherein two R.sup.1 are the same and each is a fluorine atom or a fluoroalkyl group, the method comprising step A of reacting a compound represented by formula (2):

##STR00002##

wherein R.sup.1 is as defined above, with a compound represented by formula (3):

##STR00003##

wherein R.sup.31, R.sup.32, and R.sup.33 are the same or different and each is a hydrogen atom or an alkyl group, or two of them are optionally linked to each other to form a ring optionally having one or more substituents, and
a compound represented by formula (4-1) or the like:

##STR00004##

wherein R.sup.41, R.sup.42, R.sup.43, and R.sup.44 are the same or different and each is a hydrogen atom ox an alkyl group, or two of them are optionally linked to each other to form a ring optionally having one or more substituents.

The present invention provides a nonaqueous electrolytic solution capable of improving electrochemical characteristics in the case of using an energy storage device at a high temperature and at a high voltage and further capable of inhibiting the gas generation while maintaining a capacity retention rate after storage at a high temperature and at a high voltage and also provides an energy storage device using the same. Disclosed is a nonaqueous electrolytic solution having an electrolyte salt dissolved in a nonaqueous solvent, the nonaqueous electrolytic solution containing a carboxylic acid ester compound represented by the following general formula (I).

##STR00001##

In the formula, each of R.sup.1 and R.sup.2 independently represents a hydrogen atom, a —C(═O)—OR.sup.4 group, or the like, and R.sup.1 and R.sup.2 may be bonded to each other to form a ring structure. R.sup.3 represents a hydrogen atom or the like, and n represents an integer of 1 to 3. When n is 1, then L and R.sup.4 represent an alkyl group having 1 to 6 carbon atoms or the like; and when n is 2 or 3, then L represents an n-valent connecting group, X represents a —C(═O)— group, an —S(═O)— group, an —S(═O).sub.2— group, an —S(═O).sub.2—R.sup.5—S(═O).sub.2— group or a CR.sup.6R.sup.7 group, R.sup.5 represents an alkylene group having 1 to 4 carbon atoms, and each of R.sup.6 and R.sup.7 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

The present invention provides a nonaqueous electrolytic solution capable of improving electrochemical characteristics in the case of using an energy storage device at a high temperature and at a high voltage and further capable of inhibiting the gas generation while maintaining a capacity retention rate after storage at a high temperature and at a high voltage and also provides an energy storage device using the same. Disclosed is a nonaqueous electrolytic solution having an electrolyte salt dissolved in a nonaqueous solvent, the nonaqueous electrolytic solution containing a carboxylic acid ester compound represented by the following general formula (I).

##STR00001##

In the formula, each of R.sup.1 and R.sup.2 independently represents a hydrogen atom, a —C(═O)—OR.sup.4 group, or the like, and R.sup.1 and R.sup.2 may be bonded to each other to form a ring structure. R.sup.3 represents a hydrogen atom or the like, and n represents an integer of 1 to 3. When n is 1, then L and R.sup.4 represent an alkyl group having 1 to 6 carbon atoms or the like; and when n is 2 or 3, then L represents an n-valent connecting group, X represents a —C(═O)— group, an —S(═O)— group, an —S(═O).sub.2— group, an —S(═O).sub.2—R.sup.5—S(═O).sub.2— group or a CR.sup.6R.sup.7 group, R.sup.5 represents an alkylene group having 1 to 4 carbon atoms, and each of R.sup.6 and R.sup.7 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

A method of stabilizing perfluoro(2-methylene-4-methyl-1,3-dioxolane) (hereinafter simply referred to as a “stabilization method”), including incorporating at least one selected from the group consisting of a hydroxy group-containing fluoroaromatic compound represented by General Formula (1) below and a hydroxy group-containing fluoroaromatic compound represented by General Formula (2) below into a composition containing perfluoro(2-methylene-4-methyl-1,3-dioxolane): ##STR00001##
(in the formula, R.sup.1 to R.sup.6 each independently represent one selected from the group consisting of a fluorine atom, a perfluoroalkyl group and a hydroxy group, and at least one of R.sup.1 to R.sup.6 is a hydroxy group); ##STR00002##
(in the formula, R.sup.7 to R.sup.14 each independently represent one selected from the group consisting of a fluorine atom, a perfluoroalkyl group and a hydroxy group, and at least one of R.sup.7 to R.sup.14 is a hydroxy group).

A method of stabilizing perfluoro(2-methylene-4-methyl-1,3-dioxolane) (hereinafter simply referred to as a “stabilization method”), including incorporating at least one selected from the group consisting of a hydroxy group-containing fluoroaromatic compound represented by General Formula (1) below and a hydroxy group-containing fluoroaromatic compound represented by General Formula (2) below into a composition containing perfluoro(2-methylene-4-methyl-1,3-dioxolane): ##STR00001##
(in the formula, R.sup.1 to R.sup.6 each independently represent one selected from the group consisting of a fluorine atom, a perfluoroalkyl group and a hydroxy group, and at least one of R.sup.1 to R.sup.6 is a hydroxy group); ##STR00002##
(in the formula, R.sup.7 to R.sup.14 each independently represent one selected from the group consisting of a fluorine atom, a perfluoroalkyl group and a hydroxy group, and at least one of R.sup.7 to R.sup.14 is a hydroxy group).

The present invention relates to a method for producing a 1,3-dioxolane compound represented by formula 1, the method containing step (a), in which hexafluoroacetone monohydrate is brought into contact with a metal fluoride, step (b), in which fluorine gas is brought into contact, and step (c), in which an olefin compound represented by formula 2 is brought into contact. In formulae 1 and 2, X.sup.1 to X.sup.4 each independently represent a hydrogen atom, fluorine atom, chlorine atom, or trifluoromethyl group. ##STR00001##

The present invention relates to a method for producing a 1,3-dioxolane compound represented by formula 1, the method containing step (a), in which hexafluoroacetone monohydrate is brought into contact with a metal fluoride, step (b), in which fluorine gas is brought into contact, and step (c), in which an olefin compound represented by formula 2 is brought into contact. In formulae 1 and 2, X.sup.1 to X.sup.4 each independently represent a hydrogen atom, fluorine atom, chlorine atom, or trifluoromethyl group. ##STR00001##

The invention relates to a use of a fluorination gas, and the elemental fluorine (F.sub.2) is present in a high concentration, for example, in a concentration of elemental fluorine (F.sub.2), especially of equal to much higher than 15 or even 20% by volume, and to a process for the manufacture of a fluorinated compound by direct fluorination employing a fluorination gas, wherein the elemental fluorine (F.sub.2) is present in a high concentration. The process of the invention is directed to the manufacture of a fluorinated compound, for the exception of fluorinated benzene, by direct fluorination. Especially the invention is of interest in the preparation of fluorinated organic compounds, final products and as well intermediates, for usage in agro-, pharma-, electronics-, catalyst, solvent and other functional chemical applications. The fluorination process of the invention may be performed batch-wise or in a continuous manner.

The invention relates to a use of a fluorination gas, and the elemental fluorine (F.sub.2) is present in a high concentration, for example, in a concentration of elemental fluorine (F.sub.2), especially of equal to much higher than 15 or even 20% by volume, and to a process for the manufacture of a fluorinated compound by direct fluorination employing a fluorination gas, wherein the elemental fluorine (F.sub.2) is present in a high concentration. The process of the invention is directed to the manufacture of a fluorinated compound, for the exception of fluorinated benzene, by direct fluorination. Especially the invention is of interest in the preparation of fluorinated organic compounds, final products and as well intermediates, for usage in agro-, pharma-, electronics-, catalyst, solvent and other functional chemical applications. The fluorination process of the invention may be performed batch-wise or in a continuous manner.