# US 2017/0283443 A1 · Fluorosilicon nitrile compounds

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- Number: US 2017/0283443 A1
- Document ID: US20170283443A1
- Status: Published application
- Kind: A1
- Application number: 15/506,330
- Filed: 2015-08-18
- Published: 2017-10-05
- Earliest claimed: 2014-08-27
- Assignees: Arkema Inc.
- Applicants: Arkema Inc.
- Inventors: Robert George Syvret; Craig Alan Polsz
- Web page: https://patentgrep.com/patent/US20170283443A1

## CPC

- C07F 7/14: Preparation thereof from {optionally substituted} halogenated silanes and hydrocarbons {hydrosilylation reactions}
- C07F 7/12: Organo silicon halides
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## 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.

## Claims

### Claim 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, 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;
subject to the proviso that the fluorosilicon nitrile compound is not
SiF2(CH3)(CH2CH2CH(CN)CH3); SiF2(CH3)(CH2CH2CH2CN);
SiF2(CH3)(CH2CH(CH3)CH2CN); or SiF2[CH2CH(CH3)CH2CN]2.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 1)

The fluorosilicon nitrile compound of claim 1, wherein the cyanoalkyl group or cyanoalkyl groups contain(s) a single cyano group per cyanoalkyl group.

### Claim 9 (depends on 1)

The fluorosilicon nitrile compound of claim 1, wherein the cyanoalkyl group or cyanoalkyl groups contain(s) two cyano groups per cyanoalkyl group.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 1)

The fluorosilicon nitrile compound of claim 1, wherein the cyanoalkyl group or cyanoalkyl groups are selected from the group consisting of:
—CH2CH(CN)CH3;
—CH(CN)CH2CH3;
—C(CN)(CH3)2;
—CH2CH2CN;
—CH(CN)CH3;
—CH2CH2CH(CN)CH3;
—CH2CH(CN)CH2CH3;
—(CH2)3CN;
—(CH2)2CN;
—(CH2)4CN;
—(CH2)5CN;
—(CH2)3C(CN)2CH3;
—CH(CH3)CH2CN;
—CH(CN)CH(CN)CH3;
—C(CN)(CH3)CH2CN;
—CH(CH2CN)2;
—CH(CN)CH2CH2CN;
—CH(CH3)CH(CN)2;
—C(CN)2(CH2CH3);
—CH2CH(CN)CH2CN;
—C(CN)(CH3)CH2CN;
—CH(CH2CH3)CH2CN;
—CH(CN)CH2CH2CH3;
—CH(CH3)CH2CH2CN;
—CH(CH2CN)CH2CH3;
—CH(CH3)CH(CN)CH3;
—C(CN)(CH3)CH2CH3;
—CH2CH(CH3)CH2CN;
—C(CH3)2CH2CN;
—CH(CN)CH(CH3)2;
—CH2CH2CH(CN)CH3;
—CH2CH(CH2CN)CH2CH3;
—C(CH3)(CH2CH3)CH2CN;
—CH2CH2CH(CN)CH2CH3;
—CH(CH3)CH(CN)CH2CH3;
—CH2CH2CH2CH(CN)CH3;
—CH(CH3)CH2CH(CN)CH3;
—C(CH2CH3)2(CN);
—CH2CH2CH(CH3)CH2CN;
—CH(CH3)CH(CH3)CH2CN;
—(CH2)2C(CH3)2CN;
—CH(CH3)C(CH3)2CN;
—CH(CH2CH3)CH(CN)CH3;
—CH2CH(CH3)CH2CH2CN;
—C(CH3)2CH2CH2CN;
—CH(CH2CH3)CH2CH2CN;
—CH(CH2CN)CH2CH2CH3;
—CH(CN)CH2CH2CH2CH3;
—CH(CH3)CH2CH2CH2CN;
—C(CH3)2CH(CN)CH3;
—C(CH3)(CN)CH(CH3)2;
—CH(CH2CN)CH(CH3)2;
—CH2CH(CN)CH2CH2CH3;
—C(CH3)(CN)CH2CH2CH3;
—CH2CH(CN)CH(CH3)2;
—CH(CN)CH2CH2CH2CH3;
—CH2CH(CH3)CH(CN)CH3;
—CH(CN)CH2CH(CH3)2;
—CH(CN)CH(CH3)CH2CH3;
—C(CH3)(CN)CH(CN)CH2CH3;
—C(CN)(CH2CH3)CH(CN)CH3;
—CH(CH2CN)CH2CH2CH2CN;
—CH(CN)CH2CH2CH2CH2CN;
—CH2CH(CN)CH2CH2CH2CN;
—C(CH3)(CN)CH2CH2CH2CN;
—C(CH3)(CH2CH3)CH(CN)2;
—C(CN)2CH(CH3)CH2CH3;
—C(CN)2CH2CH(CH3)2;
—CH(CH(CN)2)CH(CH3)2;
—C(CN)(CH2CH3)CH2CH2CN;
—CH(CH3)CH(CN)CH2CH2CN;
—CH2CH(CN)CH2CH(CN)CH3;
—C(CN)(CH3)CH2CH(CN)CH3;
—(CH2)3CH(CN)CH2CN;
—CH(CH3)CH2CH(CN)CH2CN;
—CH(CH2CH3)CH(CN)CH2CN;
—C(CN)(CH2CN)CH2CH2CH3;
—C(CH3)2CH(CN)CH2CN;
—C(CN)(CH2CN)CH(CH3)2;
—C(CH3)(CH2CN)CH2CH2CN;
—CH(CH2CN)CH(CH3)CH2CN;
—CH2CH(CH2CN)CH2CH2CN;
—CH2CH(CH2CN)CH(CN)CH3;
—C(CH3)(CH2CN)CH(CN)CH3;
—CH(CH(CN)2)CH2CH2CH3;
—C(CN)2CH2CH2CH2CH3;
—CH(CH2CN)CH2CH(CN)CH3;
—CH(CH2CH2CN)CH(CN)CH3;
—CH(CH3)CH2CH2CH(CN)2;
—CH(CH2CH3)CH2CH(CN)2;
—CH2CH(CH3)CH2CH(CN)2;
—C(CH3)2CH2CH(CN)2;
—CH2CH2CH2C(CN)2CH3;
—CH(CH3)CH2C(CN)2CH3;
—CH(CH(CN)2)CH(CH3)2;
—CH2CH2CH(CH3)CH(CN)2;
—CH(CH3)CH(CH3)CH(CN)2; and
—CH2CH2CH2CH2CH(CN)2 and combinations thereof.

### Claim 13 (depends on 12)

The fluorosilicon nitrile compound of claim 12, wherein the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, one fluorine atom, one cyanoalkyl group, and two C1-C8 alkyl groups, which are the same as or different from each other.

### Claim 14 (depends on 13)

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.

### Claim 15 (depends on 12)

The fluorosilicon nitrile compound of claim 12, wherein the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, two fluorine atoms, one cyanoalkyl group and one C1-C8 alkyl group.

### Claim 16 (depends on 15)

The fluorosilicon nitrile compound of claim 15, 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.

### Claim 17

A fluorosilicon nitrile compound of general formula Si(R1)(R2)(R3)(R4), wherein one or two of R1-R4 are fluorine atoms, one or two of R1-R4 are cyanoalkyl groups, which are the same as or different from each other where two cyanoalkyl groups are present, and the remaining R1-R4, if any, are alkyl groups; subject to the proviso that the fluorosilicon nitrile compound is not SiF2(CH3)(CH2CH2CH(CN)CH3); SiF2(CH3)(CH2CH2CH2CN); SiF2(CH3)(CH2CH(CH3)CH2CN); or SiF2[CH2CH(CH3)CH2CN]2.

### Claim 18 (depends on 1)

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.

### Claim 19 (depends on 18)

The method of claim 18, wherein the fluorinating agent is selected from the group consisting of HF, MF, MHF2 and SbF3, where M is Na, K, Rb, Cs or NH4.

### Claim 20 (depends on 18)

The method of claim 18, wherein the chlorosilicon nitrile compound is prepared by hydrosilylation of an alkene with a chloroalkylsilane.

### Claim 21 (depends on 20)

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

### Claim 22 (depends on 1)

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

### Claim 23 (depends on 22)

The method of claim 22, wherein the alkene is a cyanoalkene.