US-20260125405-A1 - METHOD FOR PRODUCING IMIDIC ACID OR IMIDIC ACID SALT

US20260125405A1US 20260125405 A1US20260125405 A1US 20260125405A1US-20260125405-A1

Abstract

A method for producing an imidic acid or an imidic acid salt having a phosphoryl group by a method for producing an imidic acid or an imidic acid salt represented by the following formula [1], including a reaction of allowing a phosphoryl isocyanate represented by the following formula [2] to react with a compound represented by the following formula [3]:

Inventors

Takayoshi Morinaka
Keita Nakahara
Susumu Iwasaki
Masutaka Shinmen
Mikihiro Takahashi

Assignees

CENTRAL GLASS COMPANY, LIMITED

Dates

Publication Date: 20260507
Application Date: 20231004
Priority Date: 20221007

Claims (17)

1 - 16 . (canceled)
17 . A method for producing an imidic acid or an imidic acid salt represented by the following formula [1], comprising a reaction of allowing a phosphoryl isocyanate represented by the following formula [2] to react with a compound represented by the following formula [3], wherein in the formula [1], X 1 and X 2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, wherein at least one selected from the group consisting of a fluorine atom, an oxygen atom, a nitrogen atom, and an unsaturated bond may be present in the organic group, Z is —P(═O)—, —S(═O) 2 —, or —C(═O)—, when Z is —P(═O)—, a is 1, and when Z is —S(═O) 2 —, or —C(═O)—, a is 0, R 1 and R 2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, wherein at least one selected from the group consisting of a fluorine atom, an oxygen atom, and an unsaturated bond may be present in the organic group, M m+ is a proton, an alkali metal cation, an alkaline earth metal cation, or an onium cation, and m represents the same integer as a valence of the corresponding cation, wherein in the formula [2], X 1 and X 2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, wherein at least one selected from the group consisting of a fluorine atom, an oxygen atom, a nitrogen atom, and an unsaturated bond may be present in the organic group, wherein in the formula [3], Z is —P(═O)—, —S(═O) 2 —, or —C(═O)—, when Z is —P(═O)—, a is 1, when Z is —S(═O) 2 —, a is 0, and when Z is —C(═O)—, a is 0, R 1 and R 2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, wherein at least one selected from the group consisting of a fluorine atom, an oxygen atom, and an unsaturated bond may be present in the organic group, M m+ is a proton, an alkali metal cation, an alkaline earth metal cation, or an onium cation, and m represents the same integer as a valence of the corresponding cation.
18 . The method for producing an imidic acid or an imidic acid salt according to claim 17 , wherein a used amount of the phosphoryl isocyanate represented by the formula [2] is 0.1 to 10 mol per 1 mol of the compound represented by the formula [3].
19 . The method for producing an imidic acid or an imidic acid salt according to claim 17 , wherein a reaction temperature in the reaction is −20 to 200° C.
20 . The method for producing an imidic acid or an imidic acid salt according to claim 17 , wherein the reaction is performed in a reaction solvent.
21 . The method for producing an imidic acid or an imidic acid salt according to claim 20 , wherein the reaction solvent is at least one solvent selected from the group consisting of a nitrile, a chain ether, a cyclic ether, a chain ester, a cyclic ester, a chain carbonate, a cyclic carbonate, and a sulfur-containing solvent.
22 . The method for producing an imidic acid or an imidic acid salt according to claim 17 , wherein M m+ is a proton, a lithium ion, a sodium ion, a potassium ion, a trialkyl ammonium ion, or a tetraalkyl ammonium ion.
23 . The method for producing an imidic acid or an imidic acid salt according to claim 17 , wherein X 1 and X 2 are each independently a chlorine atom, a fluorine atom, or a group selected from the group consisting of a methyl group, a trifluoromethyl group, a phenyl group, a fluorophenyl group, a vinyl group, a thienyl group, and a pyridinyl group.
24 . The method for producing an imidic acid or an imidic acid salt according to claim 17 , wherein a reaction solution after the reaction is degassing-concentrated.
25 . A method for producing an imidic acid or an imidic acid salt represented by the following formula [4], comprising a reaction of allowing a sulfonyl isocyanate represented by the following formula [5] to react with a compound represented by the following formula [6], wherein in the formula [4], X 1 and X 2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, wherein at least one selected from the group consisting of a fluorine atom, an oxygen atom, a nitrogen atom, and an unsaturated bond may be present in the organic group, R 1 is a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, wherein at least one selected from the group consisting of a fluorine atom, an oxygen atom, and an unsaturated bond may be present in the organic group, M m+ is a proton, an alkali metal cation, an alkaline earth metal cation, or an onium cation, and m represents the same integer as a valence of the corresponding cation, wherein in the formula [5], R 1 is a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, wherein at least one selected from the group consisting of a fluorine atom, an oxygen atom, and an unsaturated bond may be present in the organic group, wherein in the formula [6], X 1 and X 2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, wherein at least one selected from the group consisting of a fluorine atom, an oxygen atom, a nitrogen atom, and an unsaturated bond may be present in the organic group, M m+ is a proton, an alkali metal cation, an alkaline earth metal cation, or an onium cation, and m represents the same integer as a valence of the corresponding cation.
26 . The method for producing an imidic acid or an imidic acid salt according to claim 25 , wherein a used amount of the sulfonyl isocyanate represented by the formula [5] is 0.1 to 10 mol per 1 mol of the compound represented by the formula [6].
27 . The method for producing an imidic acid or an imidic acid salt according to claim 25 , wherein a reaction temperature in the reaction is 0 to 150° C.
28 . The method for producing an imidic acid or an imidic acid salt according to claim 25 , wherein the reaction is performed in a reaction solvent.
29 . The method for producing an imidic acid or an imidic acid salt according to claim 28 , wherein the reaction solvent is at least one solvent selected from the group consisting of a nitrile, a chain ether, a cyclic ether, a chain ester, a cyclic ester, a chain carbonate, a cyclic carbonate, and a sulfur-containing solvent.
30 . The method for producing an imidic acid or an imidic acid salt according to claim 25 , wherein M m+ is a proton, a lithium ion, a sodium ion, a potassium ion, a trialkyl ammonium ion, or a tetraalkyl ammonium ion.
31 . The method for producing an imidic acid or an imidic acid salt according to claim 25 , wherein X 1 and X 2 are each independently a chlorine atom, a fluorine atom, or a group selected from the group consisting of a methyl group, a trifluoromethyl group, a phenyl group, a fluorophenyl group, a vinyl group, a thienyl group, and a pyridinyl group.
32 . The method for producing an imidic acid or an imidic acid salt according to claim 25 , wherein the reaction solution after the reaction is degassing-concentrated.

Description

TECHNICAL FIELD The present disclosure relates to methods for producing various imidic acids or imidic acid salts having a phosphoryl group. BACKGROUND It has recently been known that various imidic acids having a phosphoryl group such as bis(phosphoryl)imide (HN(POX2)2) and asymmetric phosphorylimide (HN(POX2)(SO2X)), and metal salts and onium salts thereof are useful substances as anion sources for ionic conductive materials and ionic liquids, and electrolytes and additives for a nonaqueous electrolytic solution battery such as a lithium ion battery, a lithium battery, a lithium ion capacitor, and a sodium ion battery. Regarding a method for producing a bis(phosphoryl)imidic acid compound, Patent Literature 1 describes a method for obtaining a bis(halogenated phosphoryl)imidic acid compound by allowing a phosphoryl halide to react with ammonia in the presence of an organic base (the following Reaction Formula: (1)). Non-Patent Literature 1 describes a method for obtaining lithium bis(difluorophosphoryl)imide by allowing LiN(SiMe3)2, which is a silazane metal compound, to react with phosphoryl trifluoride (POF3) (the following Reaction Formula: (2)). Patent Literature 2 describes a method for obtaining an asymmetric phosphoryl imide by allowing a silazane derivative containing a sulfonyl group to react with phosphorus oxychloride (the following Reaction Formula: (3)). PATENT LITERATURE Patent Literature 1: JP2010-254554APatent Literature 2: Chinese Patent Publication No. CN102617414A Non-Patent Literature Non-Patent Literature 1: Z. Anorg. Allg. Chem. 412(1), 65-70 (1975) SUMMARY An object of the present disclosure is to provide a new method for producing an imidic acid or an imidic acid salt having a phosphoryl group. The inventors of the present invention have found a new production method for obtaining an imidic acid or an imidic acid salt having a phosphoryl group represented by the formula [1] or [4] described later and achieved the present disclosure. [1] A method for producing an imidic acid or an imidic acid salt represented by the following formula [1], including a reaction of allowing a phosphoryl isocyanate represented by the following formula [2] to react with a compound represented by the following formula [3]. (Hereinafter, the production method is sometimes referred to as “invention 1”.) In the formula [1], X1 and X2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from the group consisting of a fluorine atom, an oxygen atom, a nitrogen atom, and an unsaturated bond may be present in the organic group. Z is —P(═O)—, —S(═O)2—, or —C(═O)—. When Z is —P(═O)—, a is 1, and when Z is —S(═O)2—, or —C(═O)—, a is 0. R1 and R2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from the group consisting of a fluorine atom, an oxygen atom, and an unsaturated bond may be present in the organic group. Mm+ is a proton, an alkali metal cation, an alkaline earth metal cation, or an onium cation, and m represents the same integer as a valence of the corresponding cation.] [In the formula [2], X1 and X2 are the same as in the formula [1].] [In the formula [3], Z is —P(═O)—, —S(═O)2—, or —C(═O)—. When Z is —P(═O)—, a is 1. When Z is —S(═O)2—, a is 0. When Z is —C(═O)—, a is 0. R1 and R2 are each independently a chlorine atom, a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to