Fluorosilicon nitrile compounds

Patent metadata

Field	Value
Publication number	US-10155778-B2
Application number	US-201515506330-A
Country	US
Kind code	B2
Filing date	Aug 18, 2015
Priority date	Aug 27, 2014
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

Novel fluorosilicon nitrile compounds, and methods of preparing them, are described. The fluorosilicon nitrile compounds are characterized by having a total of four substituents attached to a silicon atom, wherein one or two of the substituents are fluorine atoms, one or two of the substituents are cyanoalkyl groups, which are the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other.

First claim

What is claimed is:

1. A fluorosilicon nitrile compound having a total of four substituents attached to a silicon atom, wherein one or two of the substituents are fluorine atoms, one or two of the substituents are cyanoalkyl groups containing two cyano groups per cyanoalkyl group, which are the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other.

2. The fluorosilicon nitrile compound of claim 1 , wherein one substitutent is a fluorine atom, one substituent is a cyanoalkyl group containing two cyano groups per cyanoalkyl group, and two substituents are alkyl groups, which are the same as or different from each other.

3. The fluorosilicon nitrile compound of claim 1 , wherein two substituents are fluorine atoms, one substituent is a cyanoalkyl group containing two cyano groups per cyanoalkyl group, and one substituent is an alkyl group.

4. The fluorosilicon nitrile compound of claim 1 , wherein one substituent is a fluorine atom, two substituents are cyanoalkyl groups group containing two cyano groups per cyanoalkyl group, which are the same as or different from each other, and one substituent is an alkyl group.

5. The fluorosilicon nitrile compound of claim 1 , wherein two substituents are fluorine atoms and two substituents are cyanoalkyl groups group containing two cyano groups per cyanoalkyl group, which are the same as or different from each other.

6. The fluorosilicon nitrile compound of claim 1 , wherein the cyanoalkyl groups are C2-C9 cyanoalkyl groups.

7. The fluorosilicon nitrile compound of claim 1 , wherein at least one alkyl group is present and the alkyl group is a C1-C8 alkyl group.

8. The fluorosilicon nitrile compound of claim 1 , wherein the cyanoalkyl groups contain a cyano group which is substituted at a terminal position of an alkyl radical.

9. The fluorosilicon nitrile compound of claim 1 , wherein the cyanoalkyl group or cyanoalkyl groups containing two cyano groups per cyanoalkyl group contain(s) a cyano group which is substituted at an internal position of an alkyl radical.

10. The fluorosilicon nitrile compound of claim 1 , wherein the cyanoalkyl group or cyanoalkyl groups are selected from the group consisting of:
—(CH 2 ) 3 C(CN) 2 CH 3 ;
—CH(CN)CH(CN)CH 3 ;
—C(CN)(CH 3 )CH 2 CN;
—CH(CH 2 CN) 2 ;
—CH(CN)CH 2 CH 2 CN;
—CH(CH 3 )CH(CN) 2 ;
—C(CN) 2 (CH 2 CH 3 );
—CH 2 CH(CN)CH 2 CN;
—C(CN)(CH 3 )CH 2 CN;
—C(CH 3 )(CN)CH(CN)CH 2 CH 3 ;
—C(CN)(CH 2 CH 3 )CH(CN)CH 3 ;
—CH(CH 2 CN)CH 2 CH 2 CH 2 CN;
—CH(CN)CH 2 CH 2 CH 2 CH 2 CN;
—CH 2 CH(CN)CH 2 CH 2 CH 2 CN;
—C(CH 3 )(CN)CH 2 CH 2 CH 2 CN;
—C(CH 3 )(CH 2 CH 3 )CH(CN) 2 ;
—C(CN) 2 CH(CH 3 )CH 2 CH 3 ;
—C(CN) 2 CH 2 CH(CH 3 ) 2 ;
—CH(CH(CN) 2 )CH(CH 3 ) 2 ;
—C(CN)(CH 2 CH 3 )CH 2 CH 2 CN;
—CH(CH 3 )CH(CN)CH 2 CH 2 CN;
—CH 2 CH(CN)CH 2 CH(CN)CH 3 ;
—C(CN)(CH 3 )CH 2 CH(CN)CH 3 ;
—(CH 2 ) 3 CH(CN)CH 2 CN;
—CH(CH 3 )CH 2 CH(CN)CH 2 CN;
—CH(CH 2 CH 3 )CH(CN)CH 2 CN;
—C(CN)(CH 2 CN)CH 2 CH 2 CH 3 ;
—C(CH 3 ) 2 CH(CN)CH 2 CN;
—C(CN)(CH 2 CN)CH(CH 3 ) 2 ;
—C(CH 3 )(CH 2 CN)CH 2 CH 2 CN;
—CH(CH 2 CN)CH(CH 3 )CH 2 CN;
—CH 2 CH(CH 2 CN)CH 2 CH 2 CN;
—CH 2 CH(CH 2 CN)CH(CN)CH 3 ;
—C(CH 3 )(CH 2 CN)CH(CN)CH 3 ;
—CH(CH(CN) 2 )CH 2 CH 2 CH 3 ;
—C(CN) 2 CH 2 CH 2 CH 2 CH 2 CH 3 ;
—CH(CH 2 CN)CH 2 CH(CN)CH 3 ;
—CH(CH 2 CH 2 CN)CH(CN)CH 3 ;
—CH(CH 3 )CH 2 CH 2 CH(CN) 2 ;
—CH(CH 2 CH 3 )CH 2 CH(CN) 2 ;
—CH 2 CH(CH 3 )CH 2 CH(CN) 2 ;
—C(CH 3 ) 2 CH 2 CH(CN) 2 ;
—CH(CH 3 )CH 2 C(CN) 2 CH 3 ;
—CH(CH(CN) 2 )CH(CH 3 ) 2 ;
—CH 2 CH 2 CH(CH 3 )CH(CN) 2 ;
—CH(CH 3 )CH(CH 3 )CH(CN) 2 ; and
—CH 2 CH 2 CH 2 CH 2 CH(CN) 2 and combinations thereof.

11. The fluorosilicon nitrile compound of claim 10 , wherein the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, one fluorine atom, one cyanoalkyl group containing two cyano groups per cyanoalkyl group, and two C1-C8 alkyl groups, which are the same as or different from each other.

12. The fluorosilicon nitrile compound of claim 11 , wherein the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, two alkyl groups selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and combinations thereof.

13. The fluorosilicon nitrile compound of claim 10 , wherein the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, two fluorine atoms, one cyanoalkyl group containing two cyano groups per cyanoalkyl group and one C1-C8 alkyl group.

14. The fluorosilicon nitrile compound of claim 13 , wherein the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, two alkyl groups selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and combinations thereof.

15. A method of making a fluorosilicon nitrile compound in accordance with claim 1 , wherein the method comprises reacting a chlorosilicon nitrile compound with a fluorinating agent under conditions effective to exchange fluorine atoms for the chlorine atoms in the chlorosilicon nitrile compound and wherein the chlorosilicon nitrile compound has a total of four substituents attached to a silicon atom, wherein one or two of the substituents are chlorine atoms, one or two of the substituents are cyanoalkyl groups, which may be the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other.

16. The method of claim 15 , wherein the fluorinating agent is selected from the group consisting of HF, MF, MHF 2 and SbF 3 , where M is Na, K, Rb, Cs or NH 4 .

17. The method of claim 15 , wherein the chlorosilicon nitrile compound is prepared by hydrosilylation of an alkene with a chloroalkylsilane.

18. The method of claim 17 , wherein the alkene is a cyanoalkene.

19. A method of making a fluorosilicon nitrile compound in accordance with claim 1 , wherein the method comprises hydrosilylation of an alkene with a fluoroalkylsilane.

20. The method of claim 19 , wherein the alkene is a cyanoalkene.

21. A fluorosilicon nitrile compound of general formula Si(R 1 )R 2 )(R 3 )(R 4 ), wherein one or two of R 1 -R 4 are fluorine atoms, one or two of R 1 -R 4 are cyanoalkyl groups containing two cyano groups per cyanoalkyl group, which are the same as or different from each other where two cyanoalkyl groups containing two cyano groups per cyanoalkyl group are present, and the remaining R 1 -R 4 , if any, are alkyl groups.

Assignees

• Arkema Inc

Inventors

• Syvret Robert George
• Polsz Craig Alan

Classifications

• C07F7/12

  Organo silicon halides · CPC title

• C07F7/14 Primary

  Preparation thereof from {optionally substituted} halogenated silanes and hydrocarbons {hydrosilylation reactions} · CPC title