Tetraketopiperazine unit-containing compound as an active material in batteries
AssigneeIM&T Research, Inc.
InventorTeruo Umemoto
Life of this patent
Estimating the term…
Abstract
Compounds containing at least one tetraketopiperazine-1,4-diyl unit are disclosed as active materials in the positive electrodes of batteries. Novel methods for preparing the tetraketopiperazine unit-containing compounds include: (i) reacting an oxalyl halide and an oxamide, and adding water or an aqueous alkali solution to the reaction mixture, (ii) reacting an oxalyl halide and a silylamine, (iii) reacting an oximidyl halide and an amine, (iv) reacting an oxalyl halide and a silylamine, and reacting with an amine, (v) reacting an oxalyl halide and a dioxamide, (vi) reacting an oximidyl halide and a diamine, and (vii) reacting an oxalyl halide and a silylamine, and reacting with a diamine. A novel method for preparing an oximidyl halide is also disclosed.
Claims93
A battery comprising:
- a positive electrode wherein the positive electrode comprises a compound having at least one tetraketopiperazine-1,4-diyl unit represented by the formula:
- 22
- a negative electrode for generating electrons;
- and
- an electrolyte disposed between the positive and negative electrodes, wherein the electrons generated at the negative electrode travel to the positive electrode to reduce the compound containing at least one tetraketopiperazine-1,4-diyl unit.
A method for producing a mono(tetraketopiperazine) compound represented by the formula:
- 25
- wherein R1 and R2 are independently a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, the method comprising:
- reacting an oxalyl halide represented by the formula:
- X1—COCO—X2, wherein X1 and X2 are independently a halogen atom, and an oxamide represented by the formula:
- R1NHCOCONHR2, wherein R1 and R2 are independently a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, in a solvent having a nitrile group;
- and
- adding water or an aqueous alkali solution to the reaction mixture.
A method for producing a mono(tetraketopiperazine) compound represented by the formula:
- 26
- wherein R1 and R2 are the same and a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, the method comprising:
- reacting an oxalyl halide represented by the formula X1—COCO—X2, wherein X1 and X2 are independently a halogen atom, and a silylamine represented by the formula:
- 27
- wherein the R1 is a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, and R3, R4, R5, R6, R7, and R8 are independently a substituted or unsubstituted alkyl or aryl group.
A method for producing a mono(tetraketopiperazine) compound represented by the formula:
- 28
- wherein R1 and R2 are independently a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, the method comprising:
- reacting an oximidyl halide represented by the formula:
- 29
- wherein R1 is a hydrogen atom or a substituted or unsubstituted alkyl or aryl group and X1 and X2 are independently a halogen atom, and an amine represented by the formula:
- 30
- wherein R2 is a hydrogen atom or a substituted or unsubstituted alkyl or aryl group and Y1 and Y2 are independently a hydrogen atom, SiR3R4R5, or SiR6R7R8, wherein R3, R4, R5, R6, R7, and R8 are independently a substituted or unsubstituted alkyl or aryl group.
A method for producing a mono(tetraketopiperazine) compound represented by the formula:
- 31
- wherein R1 and R2 are independently a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, the method comprising:
- reacting an oxalyl halide represented by the formula XI-COCO—X2, wherein X1 and X2 are independently a halogen atom, and a silylamine represented by the formula:
- 32
- wherein the R1 is a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, and R3, R4, R5, R6, R7, and R8 are independently a substituted or unsubstituted alkyl or aryl group;
- and reacting with an amine represented by the formula:
- 33
- wherein R2 is a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, and Y1 and Y2 are independently a hydrogen atom, SiR3R4R5, or SiR6R7R8, in which R3, R4, R5, R6, R7, and R8 are independently a substituted or unsubstituted alkyl or aryl group.
A method for producing a di(tetraketopiperazine) compound represented by the formula:
- 34
- wherein R1 and R2 are independently a hydrogen or a substituted or unsubstituted alkyl or aryl group, and A is a substituted or unsubstituted alkylene or arylene group, the method comprising:
- reacting an oxalyl halide represented by the formula X1—COCO—X2, wherein X1 and X2 are independently a halogen atom, and a dioxamide represented by the formula R1—NH—COCO—NH-A-NH—COCO—NH—R2.
A method for producing a di(tetraketopiperazine) compound represented by the formula:
- 35
- wherein R1 and R2 are independently a hydrogen atom or a substituted or unsubstituted-alkyl or aryl group, and A is a substituted or unsubstituted alkylene or arylene group, the method comprising:
- A
- reacting an oxalyl halide represented by the formula X1—COCO—X2, wherein X1 and X2 are independently a halogen atom, and a dioxamide represented by the formula R1—NH—COCO—NH-A-NH—COCO—NH—R2 in a solvent having a nitrile group;
- and
- adding water or an aqueous alkali solution to the reaction mixture.
A method for producing a di(tetraketopiperazine) compound represented by the formula:
- 36
- wherein R1 and R2 are the same and are a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, and A is a substituted or unsubstituted alkylene or arylene group, the method comprising:
- reacting an oximidyl halide represented by the formula:
- 37
- wherein X1 and X2 are independently a halogen atom, and a diamine represented by the formula:
- 38
- wherein A is a substituted or unsubstituted alkylene or arylene group, and Y1, Y2, Y3, and Y4 are independently a hydrogen atom, SiR3R4R5, SiR6R7R8, SiR9R10R11, or SiR12R13R14, in which R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, and R14 are independently a substituted or unsubstituted alkyl or aryl group.
A method for producing a di(tetraketopiperazine) compound represented by the formula:
- 39
- wherein R1 and R2 are the same and are a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, the method comprising:
- reacting an oxalyl halide represented by the formula X1—COCO—X2, wherein the X1 and X2 are independently a halogen atom, and a silylamine represented by the formula:
- 40
- wherein R3, R4, R5, R6, R7, and R8 are independently a substituted or unsubstituted alkyl or aryl group;
- and reacting with a diamine represented by the formula:
- 41
- wherein A is a substituted or unsubstituted alkylene or arylene group, and Y1, Y2, Y3, and Y4 are independently a hydrogen atom, SiR3R4R5, SiR6R7R8, SiR9R10R11, or SiR12R13R14, in which R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, and R14 are independently a substituted or unsubstituted alkyl or aryl group.
A method for producing an oximidyl halide represented by the formula:
- 42
- wherein R1 is a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, and X1 and X2 are independently a halogen atom, the method comprising:
- reacting an oxalyl halide represented by the formula X1—COCO—X2, wherein X1 and X2 are independently a halogen atom, and a silylamine represented by the formula:
- 43
- wherein the R3, R4, R5, R6, R7, and R8 are independently a substituted or unsubstituted alkyl or aryl group.
N,N′-Diethyl-2,3,5,6-tetraketopiperazine.
N-Alkyl-N′-aryl-2,3,5,6-tetraketopiperazine, wherein the alkyl group having 1 to 10 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen atom, an aryl group, an alkoxy group, and an aryloxy group, and the aryl group is an aryl group having 6 to 10 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, a halogen atom, an acyl group, a nitro group, a cyano group, an alkoxy group, an acylamino group, an alkylthio group, and an alkanesulfonyl group.
A di(tetraketopiperazine) compound represented by the formula:
- 44
- wherein R1 and R2 are independently a hydrogen atom or a substituted or unsubstituted alkyl or aryl group, and the A is a substituted or unsubstituted alkylene or arylene group.
Dependencies are inferred from the claim text.