Method for producing phosphoryl imide salt, method for producing nonaqueous electrolyte solution containing said salt, and method for producing nonaqueous secondary battery

A method for producing a nonaqueous electrolyte solution, which comprises the steps of:

• (1) performing cation exchange by bringing a phosphoryl imide salt represented by the following formula (2) into contact with a cation exchange resin having M1 n+ or a metal salt represented by the formula (4) in an organic solvent having a water content of 0.3% by mass or less, so as to produce a phosphoryl imide salt represented by the following formula (1):
• wherein M1 n+ is an alkali metal cation, an alkaline earth metal cation, a quaternary ammonium cation or a quaternary phosphonium cation,
• M2 n+ is a quaternary ammonium cation, or a tertiary ammonium cation (a protonated form of a tertiary organic amine base), or a mixture thereof,
• a cation M1 n+ of the product is different from a cation M2 n+ of the raw material,
• N is a nitrogen atom, P is a phosphorus atom, and S is a sulfur atom,
• n is 1 or 2,
• B is a chloride ion, a sulfate ion, a sulfonate ion or a carbonate ion, and
• R1, R2, and R3 are each independently selected from the group consisting of a fluorine atom, an alkyl group, an alkoxy group, an alkenyl group, an alkenyloxy group, an alkynyloxy group and an aryloxy group, and
• wherein, before the step of performing the cation exchange, said method further comprises the step of:
• mixing with an organic base, a mixture which has been previously prepared by mixing a phosphoric acid amide represented by the formula (a) below with a sulfonyl halide represented by the formula (b) below, or
• mixing with a phosphoric acid amide represented by the formula (a) below, a mixture which has been previously prepared by mixing a sulfonyl halide represented by the formula (b) below with an organic base:
• wherein R1, R2 and R3 are as defined above;
• and
• (2) dissolving at least the resultant phosphoryl imide salt and a solute in a nonaqueous solvent.

A method for producing a nonaqueous secondary battery, which comprises the steps of:

• (1) performing cation exchange by bringing a phosphoryl imide salt represented by the following formula (2) into contact with a cation exchange resin having M1 n+ or a metal salt represented by the formula (4) in an organic solvent having a water content of 0.3% by mass or less, so as to produce a phosphoryl imide salt represented by the following formula (1):
• wherein M1 n+ is an alkali metal cation, an alkaline earth metal cation, a quaternary ammonium cation or a quaternary phosphonium cation,
• M2 n+ is a quaternary ammonium cation, or a tertiary ammonium cation (a protonated form of a tertiary organic amine base), or a mixture thereof,
• a cation M1 n+ of the product is different from a cation M2 n+ of the raw material,
• N is a nitrogen atom, P is a phosphorus atom, and S is a sulfur atom,
• n is 1 or 2,
• B is a chloride ion, a sulfate ion, a sulfonate ion or a carbonate ion, and
• R1, R2, and R3 are each independently selected from a fluorine atom, an alkyl group, an alkoxy group, an alkenyl group, an alkenyloxy group, an alkynyloxy group and an aryloxy group, and
• wherein, before the step of performing the cation exchange, said method further comprises the step of:
• mixing with an organic base, a mixture which has been previously prepared by mixing a phosphoric acid amide represented by the formula (a) below with a sulfonyl halide represented by the formula (b) below, or
• mixing with a phosphoric acid amide represented by the formula (a) below, a mixture which has been previously prepared by mixing a sulfonyl halide represented by the formula (b) below with an organic base:
• wherein R1, R2 and R3 are as defined above;
• (2) dissolving at least the resultant phosphoryl imide salt and a solute in a nonaqueous solvent, so as to produce a nonaqueous electrolyte solution;
• and
• (3) fabricating a nonaqueous secondary battery comprising a positive electrode, a negative electrode and the resultant nonaqueous electrolyte solution.