Imidic acid compound having divalent anion and process for producing the same

Patent metadata

Field	Value
Publication number	US-10287165-B2
Application number	US-201515529638-A
Country	US
Kind code	B2
Filing date	Dec 1, 2015
Priority date	Dec 1, 2014
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

Provided is a novel imidic acid compound having a divalent anion useful as a pharmaceutical intermediate, an agrochemical intermediate, an acid catalyst, a battery electrolyte or an antistatic agent. The imidic acid compound is a divalent imidic acid compound represented by the following general formula (1) or (2).

[In formulae (1) and (2), R 1 to R 3 represent a fluorine atom or an organic groups selected from a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkoxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, and wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group. M 1 and M 2 represent protons, metal cations or onium cations.]

First claim

What is claimed is:

1. A divalent imidic acid compound, which is represented by the following formula (1) or (2):

wherein in formulae (1) and (2), R 1 to R 3 each independently represent a fluorine atom or an organic group selected from the group consisting of a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkoxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group; and wherein M 1 and M 2 each independently represent a proton, a metal cation or an onium cation.

2. The imidic acid compound according to claim 1 , wherein the R 1 to R 3 represent a fluorine atom or an organic group selected from the group consisting of a C1-10 alkoxy group, a C2-10 alkenyloxy group and a C2-10 alkynyloxy group.

3. The imidic acid compound according to claim 1 , wherein the alkoxy group is selected from the group consisting of a methoxy group, an ethoxy group and a propoxy group; the alkenyloxy group is selected from the group consisting of a 1-propenyloxy group, a 2-propenyloxy group, a 2-butenyloxy group and a 3-butenyloxy group; and the alkynyloxy group is selected from the group consisting of a 2-propynyloxy group and a 1,1-dimethyl-2-propynyloxy group.

4. The imidic acid compound according to claim 1 , wherein the R 1 to R 3 are all fluorine atoms.

5. The imidic acid compound according to claim 1 , wherein, in the formula (1), R 1 represents a fluorine atom, and R 2 represents an organic group selected from the group consisting of a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkyloxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, and wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group.

6. The imidic acid compound according to claim 1 , wherein M 1 and M 2 in the formulae (1) and (2) each represent at least one cation selected from the group consisting of a proton, a lithium ion, a sodium ion, a potassium ion, a tetraalkylammonium ion and a tetraalkylphosphonium ion.

7. An electrolyte for an electrochemical device, comprising the imidic acid compound according to claim 1 .

8. An antistatic agent, comprising the imidic acid compound according to claim 1 .

9. A process for producing an imidic acid compound represented by the following formula (1),

which comprises,
in the presence of an organic base or an inorganic base, reacting a fluorophosphoric amide salt of the formula M 1 [PO 2 F(NH 2 )] and/or M 2 [PO 2 F(NH 2 )], wherein M 1 and M 2 represent protons, metal cations or onium cations with
a halogenated phosphate of the formula O═PR 1 R 2 X, wherein X represents a halogen, and R 1 and R 2 each independently represent a fluorine atom or an organic group selected from the group consisting of a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkoxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, and wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group,
wherein, in formula (1), R 1 , R 2 , M 1 and M 2 are each as defined above.

10. A process for producing an imidic acid compound represented by the following formula (1),

comprising,
in the presence of an organic base or an inorganic base, reacting a phosphoramide of the formula O═PR 1 R 2 (NH 2 ), wherein R 1 and R 2 each independently represent a fluorine atom or an organic group selected from the group consisting of a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkoxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group, with
a fluorophosphate of the formula M 1 [PO 2 FX] and/or M 2 [PO 2 FX], wherein X represents a halogen, and M 1 and M 2 represent protons, metal cations or onium cations,
wherein, in formula (1), R 1 , R 2 , M 1 and M 2 are each as defined above.

11. A process for producing an imidic acid compound represented by the following formula (2),

comprising,
in the presence of an organic base or an inorganic base, reacting a fluorophosphoric amide salt of the formula M 1 [PO 2 F(NH 2 )] and/or M 2 [PO 2 F(NH 2 )], wherein M 1 and M 2 represent protons, metal cations or onium cations with
a sulfonyl halide of the formula R 3 SO 2 X, wherein X represents a halogen, and R 3 represents a fluorine atom or an organic group selected from the group consisting of a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkoxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, and wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group,
wherein, in formula (2), R 3 , M 1 and M 2 are each as defined above.

12. A process for producing an imidic acid compound represented by the following formula (2),

comprising,
in the presence of an organic base or an inorganic base, reacting a sulfonyl amide of the formula R 3 SO 2 NH 2 , wherein R 3 represents a fluorine atom or an organic group selected from the group consisting of a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkoxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group, with
a fluorophosphate of the formula M 1 [PO 2 FX] and/or M 2 [PO 2 FX], wherein X represents a halogen, and M 1 and M 2 represent protons, metal cations or onium cations,
wherein, in formula (2), R 3 , M 1 and M 2 are each as defined above.

Assignees

• Central Glass Co Ltd

Inventors

• Morinaka Takayoshi
• Kubo Makoto
• Kawabata Wataru
• Yamamoto Kenta
• Mori Takashi
• Shinmen Masutaka
• Matsuzaki Hiroki
• Kondo Ryosuke
• Takahashi Mikihiro

Classifications

• B01J31/0264

  Phosphorus acid amides · CPC title

• H01M6/166

  by the solute · CPC title

• H01G11/62

  characterised by the solute, e.g. salts, anions or cations therein · CPC title

• H01M10/0568

  characterised by the solutes · CPC title

• Y02E60/13

  Energy storage using capacitors · CPC title