Silylated cyclic phosphonamides

Patent metadata

Field	Value
Publication number	US-2016289247-A1
Application number	US-201415038322-A
Country	US
Kind code	A1
Filing date	Nov 21, 2014
Priority date	Nov 26, 2013
Publication date	Oct 6, 2016
Grant date	—

Abstract

The invention relates to silylated cyclic phosphonamides of the general formula (1) in which R 1 represents an unsubstituted or fluoro-substituted alkyl group with 1-20 carbon atoms, R 2 , R 3 each represent an unsubstituted or fluoro-substituted alkyl or alkyl group with 1-20 carbon atoms or a siloxy group with 1-20 silicon atoms, wherein two or three of the groups R 1 , R 2 , R 3 can be connected to each other, R4 represents an unsubstituted or fluoro-substituted alkyl group with 1-20 carbon atoms, and n represents the values 1 or 2. The invention also relates to a method for producing the phosophonamides of the general formula (1), to diamines used during the production of the phosphonamides, to an electrolyte which contains the phosphonamides of the general formula (1), and to a lithium-ion battery which comprises a cathode, an anode, a separator, and the electrolyte.

First claim

1 . A silylated cyclic phosphonamide of the general formula 1

where
R 1 is an unsubstituted or fluorine-substituted alkyl radical having 1-20 carbon atoms,
R 2 , R 3 are each an unsubstituted or fluorine-substituted alkyl or alkoxy radical having 1-20 carbon atoms or a siloxy radical having 1-20 silicon atoms, where two or three of the radicals R 1 , R 2 , R 3 can be joined to one another,
R 4 is an unsubstituted or fluorine-substituted alkyl radical having 1-20 carbon atoms and
n is 1 or 2.

2 . The silylated cyclic phosphonamide as claimed in claim 1 , wherein R 1 and R 4 are members independently selected from the group consisting of methyl, ethyl, n-propyl and isopropyl radicals.

3 . The silylated cyclic phosphonamide as claimed in claim 1 , wherein R 2 and R 3 are members independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, methoxy and ethoxy radicals.

4 . A process for preparing silylated cyclic phosphonamides of the general formula 1

wherein diamines of the general formula 2
R 1 R 2 R 3 Si—CH 2 —NH—CH 2 —(CH 2 ) n —NH—CH 2 —SiR 1 R 2 R 3   (2)

are reacted with a phosphonic dihalide of the general formula 3
R 4 POX 2   (3),

where
X is fluorine, chloride or bromine,
R 1 is an unsubstituted or fluorine-substituted alkyl radical having 1-20 carbon atoms,
R 2 , R 3 are each an unsubstituted or fluorine-substituted alkyl or alkoxy radical having 1-20 carbon atoms or a siloxy radical having 1-20 silicon atoms, where two or three of the radicals R 1 , R 2 , R 3 can be joined to one another,
R 4 is an unsubstituted or fluorine-substituted alkyl radical having 1-20 carbon atoms and
n is 1 or 2.

5 . The process as claimed in claim 4 , wherein X is chlorine.

6 . An electrolyte containing
aprotic solvent, lithium-containing electrolyte salt and the silylated cyclic phosphonamide of the general formula 1 as claimed in claim 1 .

7 . The electrolyte as claimed in claim 6 , wherein the aprotic solvent is a member selected from the group consisting of organic carbonates, cyclic esters, linear esters, cyclic ethers, linear ethers, ketones, lactones, sulfolanes, dimethyl sulfoxide, formamide, dimethylformamide, 3-methyl-1,3-oxazolidin-2-one and mixtures of these solvents.

8 . The electrolyte as claimed in claim 6 , wherein the lithium-containing electrolyte salt is a member selected from the group consisting of LiPF 6 , LiBF 4 , LiClO 4 , LiAsF 6 , LiSO 3 C x F 2x+1 , (LiB(C 2 O 4 ) 2 , LiBF 2 (C 2 O 4 )), LiN(SO 2 C x F 2x+1 ) 2 and LiC(SO 2 CxF 2x+1 ) 3 , where x is an integer from 0 to 8, and mixtures thereof.

9 . The electrolyte as claimed in claim 6 , containing 1-10% by weight of the phosphonamide of the general formula 1.

10 . A lithium ion battery comprising a cathode, an anode, a separator and the electrolyte as claimed in claim 6 .

11 . (canceled)

12 . The silylated cyclic phosphonamide as claimed in claim 2 , wherein R 2 and R 3 are members independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, methoxy and ethoxy radicals.

13 . The electrolyte as claimed in claim 7 , wherein the lithium-containing electrolyte salt is a member selected from the group consisting of LiPF 6 , LiBF 4 , LiClO 4 , LiAsF 6 , LiSO 3 C x F 2x+1 , (LiB(C 2 O 4 ) 2 , LiBF 2 (C 2 O 4 )), LiN(SO 2 C x F 2x+1 ) 2 and LiC(SO 2 CxF 2x+1 ) 3 , where x is an integer from 0 to 8, and mixtures thereof.

14 . The electrolyte as claimed in claim 13 , containing 0.1-10% by weight of the phosphonamide of the general formula 1.

15 . A lithium ion battery comprising a cathode, an anode, a separator and the electrolyte as claimed in claim 14 .

Assignees

• Wacker Chemie Ag

Inventors

• Bockholt Andreas
• Gigler Peter

Classifications

• C07F9/65848 Primary

  Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring · CPC title

• C07F7/0803 Primary

  Compounds with Si-C or Si-Si linkages · CPC title

• H01M10/0525

  Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries · CPC title

• H01M10/0568

  characterised by the solutes · CPC title

• C07F7/082 Primary

  Chemistry & Metallurgy · mapped topic