2-(Alkylcarbonyloxy)-1, 1-Difluoroethanesulfonic Acid Salt and Method for Producing the Same

A sulfonic acid ammonium salt represented by the following formula [3]

• wherein A+ represents an ammonium ion while R represents a linear or branched alkyl group having 1 to 10 carbon atoms, an alicyclic organic group having 3 to 20 carbon atoms, an organic group having 3 to 20 carbon atoms and containing an alicyclic organic group and a linear alkylene group, a monocyclic or polycyclic lactone having 3 to 30 carbon atoms, or an aryl group having 6 to 20 carbon atoms,
• wherein some or all of hydrogen atoms in each of the alkyl group, the alicyclic organic group, the organic group containing the alicyclic organic group and the linear alkylene group, the monocyclic or polycyclic lactone and the aryl group may be substituted with fluorine, a hydroxyl group, a hydroxycarbonyl group, or a linear, branched or cyclic alkoxy group having 1 to 6 carbon atoms,
• wherein two hydrogen atoms on the same carbon that constructs the alkyl group, the alicyclic organic group, or the organic group containing the alicyclic organic group and the linear alkylene group may be substituted with one oxygen atom to form a keto group, and
• wherein those who have in its R structure an unconjugated unsaturated moiety (a double or triple bond) are excepted.

A method for producing a 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt represented by a formula [2]

• comprising the step of:
• reacting a carboxylic acid bromodifluoroethyl ester represented by a formula [1]
• with a sulfinating agent in the presence of an amine,
• wherein R represents a linear or branched alkyl group having 1 to 10 carbon atoms, an alicyclic organic group having 3 to 20 carbon atoms, an organic group having 3 to 20 carbon atoms and containing an alicyclic organic group and a linear alkylene group, a monocyclic or polycyclic lactone having 3 to 30 carbon atoms, or an aryl group having 6 to 20 carbon atoms,
• wherein some or all of hydrogen atoms in each of the alkyl group, the alicyclic organic group, the organic group containing the alicyclic organic group and the linear alkylene group, the monocyclic or polycyclic lactone and the aryl group may be substituted with fluorine, a hydroxyl group, a hydroxycarbonyl group, or a linear, branched or cyclic alkoxy group having 1 to 6 carbon atoms,
• wherein two hydrogen atoms on the same carbon that constructs the alkyl group, the alicyclic organic group, or the organic group containing the alicyclic organic group and the linear alkylene group may be substituted with one oxygen atom to form a keto group, and
• wherein those who have in its R structure an unconjugated unsaturated moiety (a double or triple bond) are excepted.

A method for producing a 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt represented by a formula [3]

• comprising two processes including:
• a 1st process (a sulfination process) for reacting a carboxylic acid bromodifluoroethyl ester represented by a formula [1]
• with a sulfinating agent in the presence of an amine thereby obtaining a 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt represented by a formula [2]
• and
• a 2nd process (an oxidation process) for reacting the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt represented by the formula [2] and obtained by the 1st process (the sulfination process) with an oxidizing agent thereby obtaining a 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt represented by the formula [3],
• wherein R represents a linear or branched alkyl group having 1 to 10 carbon atoms, an alicyclic organic group having 3 to 20 carbon atoms, an organic group having 3 to 20 carbon atoms and containing an alicyclic organic group and a linear alkylene group, a monocyclic or polycyclic lactone having 3 to 30 carbon atoms, or an aryl group having 6 to 20 carbon atoms,
• wherein some or all of hydrogen atoms in each of the alkyl group, the alicyclic organic group, the organic group containing the alicyclic organic group and the linear alkylene group, the monocyclic or polycyclic lactone and the aryl group may be substituted with fluorine, a hydroxyl group, a hydroxycarbonyl group, or a linear, branched or cyclic alkoxy group having 1 to 6 carbon atoms,
• wherein two hydrogen atoms on the same carbon that constructs the alkyl group, the alicyclic organic group, or the organic group containing the alicyclic organic group and the linear alkylene group may be substituted with one oxygen atom to form a keto group,
• wherein those who have in its R structure an unconjugated unsaturated moiety (a double or triple bond) are excepted, and
• wherein A+ represents an ammonium ion.