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FLUOROSILICON NITRILE COMPOUNDS

20170283443 · 2017-10-05

    Inventors

    Cpc classification

    International classification

    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

    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 SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH(CN)CH.sub.3); SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH.sub.2CN); SiF.sub.2(CH.sub.3)(CH.sub.2CH(CH.sub.3)CH.sub.2CN); or SiF.sub.2[CH.sub.2CH(CH.sub.3)CH.sub.2CN].sub.2.

    2. 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.

    3. 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.

    4. 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.

    5. 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.

    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 group or cyanoalkyl groups contain(s) a single cyano group per cyanoalkyl group.

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

    10. 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.

    11. 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.

    12. The fluorosilicon nitrile compound of claim 1, wherein the cyanoalkyl group or cyanoalkyl groups are selected from the group consisting of: —CH.sub.2CH(CN)CH.sub.3; —CH(CN)CH.sub.2CH.sub.3; —C(CN)(CH.sub.3).sub.2; —CH.sub.2CH.sub.2CN; —CH(CN)CH.sub.3; —CH.sub.2CH.sub.2CH(CN)CH.sub.3; —CH.sub.2CH(CN)CH.sub.2CH.sub.3; —(CH.sub.2).sub.3CN; —(CH.sub.2).sub.2CN; —(CH.sub.2).sub.4CN; —(CH.sub.2).sub.5CN; —(CH.sub.2).sub.3C(CN).sub.2CH.sub.3; —CH(CH.sub.3)CH.sub.2CN; —CH(CN)CH(CN)CH.sub.3; —C(CN)(CH.sub.3)CH.sub.2CN; —CH(CH.sub.2CN).sub.2; —CH(CN)CH.sub.2CH.sub.2CN; —CH(CH.sub.3)CH(CN).sub.2; —C(CN).sub.2(CH.sub.2CH.sub.3); —CH.sub.2CH(CN)CH.sub.2CN; —C(CN)(CH.sub.3)CH.sub.2CN; —CH(CH.sub.2CH.sub.3)CH.sub.2CN; —CH(CN)CH.sub.2CH.sub.2CH.sub.3; —CH(CH.sub.3)CH.sub.2CH.sub.2CN; —CH(CH.sub.2CN)CH.sub.2CH.sub.3; —CH(CH.sub.3)CH(CN)CH.sub.3; —C(CN)(CH.sub.3)CH.sub.2CH.sub.3; —CH.sub.2CH(CH.sub.3)CH.sub.2CN; —C(CH.sub.3).sub.2CH.sub.2CN; —CH(CN)CH(CH.sub.3).sub.2; —CH.sub.2CH.sub.2CH(CN)CH.sub.3; —CH.sub.2CH(CH.sub.2CN)CH.sub.2CH.sub.3; —C(CH.sub.3)(CH.sub.2CH.sub.3)CH.sub.2CN; —CH.sub.2CH.sub.2CH(CN)CH.sub.2CH.sub.3; —CH(CH.sub.3)CH(CN)CH.sub.2CH.sub.3; —CH.sub.2CH.sub.2CH.sub.2CH(CN)CH.sub.3; —CH(CH.sub.3)CH.sub.2CH(CN)CH.sub.3; —C(CH.sub.2CH.sub.3).sub.2(CN); —CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CN; —CH(CH.sub.3)CH(CH.sub.3)CH.sub.2CN; —(CH.sub.2).sub.2C(CH.sub.3).sub.2CN; —CH(CH.sub.3)C(CH.sub.3).sub.2CN; —CH(CH.sub.2CH.sub.3)CH(CN)CH.sub.3; —CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2CN; —C(CH.sub.3).sub.2CH.sub.2CH.sub.2CN; —CH(CH.sub.2CH.sub.3)CH.sub.2CH.sub.2CN; —CH(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.3; —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.3; —CH(CH.sub.3)CH.sub.2CH.sub.2CH.sub.2CN; —C(CH.sub.3).sub.2CH(CN)CH.sub.3; —C(CH.sub.3)(CN)CH(CH.sub.3).sub.2; —CH(CH.sub.2CN)CH(CH.sub.3).sub.2; —CH.sub.2CH(CN)CH.sub.2CH.sub.2CH.sub.3; —C(CH.sub.3)(CN)CH.sub.2CH.sub.2CH.sub.3; —CH.sub.2CH(CN)CH(CH.sub.3).sub.2; —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.3; —CH.sub.2CH(CH.sub.3)CH(CN)CH.sub.3; —CH(CN)CH.sub.2CH(CH.sub.3).sub.2; —CH(CN)CH(CH.sub.3)CH.sub.2CH.sub.3; —C(CH.sub.3)(CN)CH(CN)CH.sub.2CH.sub.3; —C(CN)(CH.sub.2CH.sub.3)CH(CN)CH.sub.3; —CH(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.2CN; —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN; —CH.sub.2CH(CN)CH.sub.2CH.sub.2CH.sub.2CN; —C(CH.sub.3)(CN)CH.sub.2CH.sub.2CH.sub.2CN; —C(CH.sub.3)(CH.sub.2CH.sub.3)CH(CN).sub.2; —C(CN).sub.2CH(CH.sub.3)CH.sub.2CH.sub.3; —C(CN).sub.2CH.sub.2CH(CH.sub.3).sub.2; —CH(CH(CN).sub.2)CH(CH.sub.3).sub.2; —C(CN)(CH.sub.2CH.sub.3)CH.sub.2CH.sub.2CN; —CH(CH.sub.3)CH(CN)CH.sub.2CH.sub.2CN; —CH.sub.2CH(CN)CH.sub.2CH(CN)CH.sub.3; —C(CN)(CH.sub.3)CH.sub.2CH(CN)CH.sub.3; —(CH.sub.2).sub.3CH(CN)CH.sub.2CN; —CH(CH.sub.3)CH.sub.2CH(CN)CH.sub.2CN; —CH(CH.sub.2CH.sub.3)CH(CN)CH.sub.2CN; —C(CN)(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.3; —C(CH.sub.3).sub.2CH(CN)CH.sub.2CN; —C(CN)(CH.sub.2CN)CH(CH.sub.3).sub.2; —C(CH.sub.3)(CH.sub.2CN)CH.sub.2CH.sub.2CN; —CH(CH.sub.2CN)CH(CH.sub.3)CH.sub.2CN; —CH.sub.2CH(CH.sub.2CN)CH.sub.2CH.sub.2CN; —CH.sub.2CH(CH.sub.2CN)CH(CN)CH.sub.3; —C(CH.sub.3)(CH.sub.2CN)CH(CN)CH.sub.3; —CH(CH(CN).sub.2)CH.sub.2CH.sub.2CH.sub.3; —C(CN).sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.3; —CH(CH.sub.2CN)CH.sub.2CH(CN)CH.sub.3; —CH(CH.sub.2CH.sub.2CN)CH(CN)CH.sub.3; —CH(CH.sub.3)CH.sub.2CH.sub.2CH(CN).sub.2; —CH(CH.sub.2CH.sub.3)CH.sub.2CH(CN).sub.2; —CH.sub.2CH(CH.sub.3)CH.sub.2CH(CN).sub.2; —C(CH.sub.3).sub.2CH.sub.2CH(CN).sub.2; —CH.sub.2CH.sub.2CH.sub.2C(CN).sub.2CH.sub.3; —CH(CH.sub.3)CH.sub.2C(CN).sub.2CH.sub.3; —CH(CH(CN).sub.2)CH(CH.sub.3).sub.2; —CH.sub.2CH.sub.2CH(CH.sub.3)CH(CN).sub.2; —CH(CH.sub.3)CH(CH.sub.3)CH(CN).sub.2; and —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH(CN).sub.2 and combinations thereof.

    13. 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.

    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. 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.

    16. 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.

    17. A fluorosilicon nitrile compound of general formula Si(R.sup.1)(R.sup.2)(R.sup.3)(R.sup.4), wherein one or two of R.sup.1-R.sup.4 are fluorine atoms, one or two of R.sup.1-R.sup.4 are cyanoalkyl groups, which are the same as or different from each other where two cyanoalkyl groups are present, and the remaining R.sup.1-R.sup.4, if any, are alkyl groups; subject to the proviso that the fluorosilicon nitrile compound is not SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH(CN)CH.sub.3); SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH.sub.2CN); SiF.sub.2(CH.sub.3)(CH.sub.2CH(CH.sub.3)CH.sub.2CN); or SiF.sub.2[CH.sub.2CH(CH.sub.3)CH.sub.2CN].sub.2.

    18. 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.

    19. The method of claim 18, wherein the fluorinating agent is selected from the group consisting of HF, MF, MHF.sub.2 and SbF.sub.3, where M is Na, K, Rb, Cs or NH.sub.4.

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

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

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

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

    Description

    DETAILED DESCRIPTION OF CERTAIN EMBODIMENTS OF THE INVENTION

    [0007] A fluorosilicon nitrile compound in accordance with the present invention has 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. However, the following fluorosilicon nitrile compounds, which are known compounds, are not considered to be within the scope of the present invention: SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH(CN)CH.sub.3); SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH.sub.2CN); SiF.sub.2(CH.sub.3)(CH.sub.2CH(CH.sub.3)CH.sub.2CN); and SiF.sub.2[CH.sub.2CH(CH.sub.3)CH.sub.2CN].sub.2.

    [0008] In one embodiment of the invention, one substituent attached to the silicon atom 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.

    [0009] In another embodiment of the invention, two substituents attached to the silicon atom are fluorine atoms, one substituent is a cyanoalkyl group, and one substituent is an alkyl group.

    [0010] According to another embodiment, one substituent attached to the silicon atom 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.

    [0011] In still another embodiment of the invention, two substituents attached to the silicon atom are fluorine atoms and two substituents are cyanoalkyl groups, which are the same as or different from each other.

    [0012] The cyanoalkyl group or groups attached to the silicon atom may be C2-C9 cyanoalkyl groups, in one aspect of the invention. If two cyanoalkyl groups are present, they may be the same as or different from each other. The alkyl radical bearing one or more cyano (—CN) groups in the cyanoalkyl group may be a straight chain, branched, or alicyclic-containing alkyl radical. Each cyanoalkyl group may contain one, two or more cyano groups per cyanoalkyl group. Each cyano group may be substituted, for example, at a terminal position of an alkyl radical or at an internal position of an alkyl radical. For example, where the alkyl radical is a straight chain C4 alkyl radical, a cyano group may be substituted at the terminal position to provide the cyanoalkyl group —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN or at an internal position to provide one of the following cyanoalkyl groups: —CH(CN)CH.sub.2CH.sub.2CH.sub.3; —CH.sub.2CH(CN)CH.sub.2CH.sub.3; —CH.sub.2CH.sub.2CH(CN)CH.sub.3.

    [0013] Suitable cyanoalkyl groups may, for example, be selected from the group consisting of: [0014] —CH.sub.2CH(CN)CH.sub.3; [0015] —CH(CN)CH.sub.2CH.sub.3; [0016] —C(CN)(CH.sub.3).sub.2; [0017] —CH.sub.2CH.sub.2CN; [0018] —CH(CN)CH.sub.3; [0019] —CH.sub.2CH.sub.2CH(CN)CH.sub.3; [0020] —CH.sub.2CH(CN)CH.sub.2CH.sub.3; [0021] —(CH.sub.2).sub.3CN; [0022] —(CH.sub.2).sub.2CN; [0023] —(CH.sub.2).sub.4CN; [0024] —(CH.sub.2).sub.5CN; [0025] —(CH.sub.2).sub.3C(CH.sub.3).sub.2CN; [0026] —CH(CH.sub.3)CH.sub.2CN; [0027] —CH(CN)CH(CN)CH.sub.3; [0028] —C(CN)(CH.sub.3)CH.sub.2CN; [0029] —CH(CH.sub.2CN).sub.2; [0030] —CH(CN)CH.sub.2CH.sub.2CN; [0031] —CH(CH.sub.3)CH(CN).sub.2; [0032] —C(CN).sub.2(CH.sub.2CH.sub.3); [0033] —CH.sub.2CH(CN)CH.sub.2CN; [0034] —C(CN)(CH.sub.3)CH.sub.2CN; [0035] —CH(CH.sub.2CH.sub.3)CH.sub.2CN; [0036] —CH(CN)CH.sub.2CH.sub.2CH.sub.3; [0037] —CH(CH.sub.3)CH.sub.2CH.sub.2CN; [0038] —CH(CH.sub.2CN)CH.sub.2CH.sub.3; [0039] —CH(CH.sub.3)CH(CN)CH.sub.3; [0040] —C(CN)(CH.sub.3)CH.sub.2CH.sub.3; [0041] —CH.sub.2CH(CN)CH.sub.2CH.sub.3; [0042] —CH.sub.2CH(CH.sub.3)CH.sub.2CN; [0043] —C(CH.sub.3).sub.2CH.sub.2CN; [0044] —CH(CN)CH(CH.sub.3).sub.2; [0045] —CH.sub.2CH.sub.2CH(CN)CH.sub.3; [0046] —CH.sub.2CH(CH.sub.2CN)CH.sub.2CH.sub.3; [0047] —C(CH.sub.3)(CH.sub.2CH.sub.3)CH.sub.2CN; [0048] —CH.sub.2CH.sub.2CH(CN)CH.sub.2CH.sub.3; [0049] —CH(CH.sub.3)CH(CN)CH.sub.2CH.sub.3; [0050] —CH.sub.2CH.sub.2CH.sub.2CH(CN)CH.sub.3; [0051] —CH(CH.sub.3)CH.sub.2CH(CN)CH.sub.3; [0052] —C(CH.sub.2CH.sub.3).sub.2(CN); [0053] —CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CN; [0054] —CH(CH.sub.3)CH(CH.sub.3)CH.sub.2CN; [0055] —(CH.sub.2).sub.2C(CH.sub.3).sub.2CN; [0056] —CH(CH.sub.3)C(CH.sub.3).sub.2CN; [0057] —CH(CH.sub.2CH.sub.3)CH(CN)CH.sub.3; [0058] —CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2CN; [0059] —C(CH.sub.3).sub.2CH.sub.2CH.sub.2CN; [0060] —CH(CH.sub.2CH.sub.3)CH.sub.2CH.sub.2CN; [0061] —CH(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.3; [0062] —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.3; [0063] —CH(CH.sub.3)CH.sub.2CH.sub.2CH.sub.2CN; [0064] —C(CH.sub.3).sub.2CH(CN)CH.sub.3; [0065] —C(CH.sub.3)(CN)CH(CH.sub.3).sub.2; [0066] —CH(CH.sub.2CN)CH(CH.sub.3).sub.2; [0067] —CH.sub.2CH(CN)CH.sub.2CH.sub.2CH.sub.3; [0068] —C(CH.sub.3)(CN)CH.sub.2CH.sub.2CH.sub.3; [0069] —CH.sub.2CH(CN)CH(CH.sub.3).sub.2; [0070] —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.3; [0071] —CH.sub.2CH(CH.sub.3)CH(CN)CH.sub.3; [0072] —CH(CN)CH.sub.2CH(CH.sub.3).sub.2; [0073] —CH(CN)CH(CH.sub.3)CH.sub.2CH.sub.3; [0074] —C(CH.sub.3)(CN)CH(CN)CH.sub.2CH.sub.3; [0075] —C(CN)(CH.sub.2CH.sub.3)CH(CN)CH.sub.3; [0076] —CH(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.2CN; [0077] —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN; [0078] —CH.sub.2CH(CN)CH.sub.2CH.sub.2CH.sub.2CN; [0079] —C(CH.sub.3)(CN)CH.sub.2CH.sub.2CH.sub.2CN; [0080] —C(CH.sub.3)(CH.sub.2CH.sub.3)CH(CN).sub.2; [0081] —C(CN).sub.2CH(CH.sub.3)CH.sub.2CH.sub.3; [0082] —C(CN).sub.2CH.sub.2CH(CH.sub.3).sub.2; [0083] —CH(CH(CN).sub.2)CH(CH.sub.3).sub.2; [0084] —C(CN)(CH.sub.2CH.sub.3)CH.sub.2CH.sub.2CN; [0085] —CH(CH.sub.3)CH(CN)CH.sub.2CH.sub.2CN; [0086] —CH.sub.2CH(CN)CH.sub.2CH(CN)CH.sub.3; [0087] —C(CN)(CH.sub.3)CH.sub.2CH(CN)CH.sub.3; [0088] —(CH.sub.2).sub.3CH(CN)CH.sub.2CN; [0089] —CH(CH.sub.3)CH.sub.2CH(CN)CH.sub.2CN; [0090] —CH(CH.sub.2CH.sub.3)CH(CN)CH.sub.2CN; [0091] —C(CN)(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.3; [0092] —C(CH.sub.3).sub.2CH(CN)CH.sub.2CN; [0093] —C(CN)(CH.sub.2CN)CH(CH.sub.3).sub.2; [0094] —C(CH.sub.3)(CH.sub.2CN)CH.sub.2CH.sub.2CN; [0095] —CH(CH.sub.2CN)CH(CH.sub.3)CH.sub.2CN; [0096] —CH.sub.2CH(CH.sub.2CN)CH.sub.2CH.sub.2CN; [0097] —CH.sub.2CH(CH.sub.2CN)CH(CN)CH.sub.3; [0098] —C(CH.sub.3)(CH.sub.2CN)CH(CN)CH.sub.3; [0099] —CH(CH(CN).sub.2)CH.sub.2CH.sub.2CH.sub.3; [0100] —C(CN).sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.3; [0101] —CH(CH.sub.2CN)CH.sub.2CH(CN)CH.sub.3; [0102] —CH(CH.sub.2CH.sub.2CN)CH(CN)CH.sub.3; [0103] —CH(CH.sub.3)CH.sub.2CH.sub.2CH(CN).sub.2; [0104] —CH(CH.sub.2CH.sub.3)CH.sub.2CH(CN).sub.2; [0105] —CH.sub.2CH(CH.sub.3)CH.sub.2CH(CN).sub.2; [0106] —C(CH.sub.3).sub.2CH.sub.2CH(CN).sub.2; [0107] —CH.sub.2CH.sub.2CH.sub.2C(CN).sub.2CH.sub.3; [0108] —CH(CH.sub.3)CH.sub.2C(CN).sub.2CH.sub.3; [0109] —CH(CH(CN).sub.2)CH(CH.sub.3).sub.2; [0110] —CH.sub.2CH.sub.2CH(CH.sub.3)CH(CN).sub.2; [0111] —CH(CH.sub.3)CH(CH.sub.3)CH(CN).sub.2; and [0112] —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH(CN).sub.2 and combinations thereof, where the fluorosilicon nitrile compound contains two cyanoalkyl groups per molecule.

    [0113] When at least one alkyl group is present in the fluorosilicon nitrile compound as a substituent attached to the silicon atom, the alkyl group may, for example, be a C1-C8 alkyl group. The alkyl group may be straight chain or branched or may contain a cyclic structure (i.e., the alkyl group may be alicyclic). If two alkyl groups are attached to the silicon atom, they may be the same as each other or different from each other. Suitable alkyl groups include, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, and n-octyl and isomers thereof.

    [0114] In one aspect of the invention, 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. In another aspect of the invention, the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, two fluorine atoms, one cyanoalkyl group and one C1-C8 alkyl group. In these embodiments, the C1-C8 alkyl groups may, for example, be selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and combinations thereof.

    [0115] A further embodiment of the invention provides a fluorosilicon nitrile compound of general formula Si(R.sup.1)(R.sup.2)(R.sup.3)(R.sup.4), wherein one or two of R.sup.1-R.sup.4 are fluorine atoms, one or two of R.sup.1-R.sup.4 are cyanoalkyl groups, which are the same as or different from each other where two cyanoalkyl groups are present, and the remaining R.sup.1-R.sup.4, if any, are alkyl groups; subject to the proviso that the fluorosilicon nitrile compound is not SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH(CN)CH.sub.3); SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH.sub.2CN); SiF.sub.2(CH.sub.3)(CH.sub.2CH(CH.sub.3)CH.sub.2CN); or SiF.sub.2[CH.sub.2CH(CH.sub.3)CH.sub.2CN].sub.2. The alkyl groups and cyanoalkyl groups may be any of such groups described previously.

    [0116] For example, R.sup.1 and R.sup.2 may both be F, R.sup.3 may be an alkyl group and R.sup.4 may be a cyanoalkyl group. Alternatively, R.sup.1 and R.sup.2 may both be F and R.sup.3 and R.sup.4 may both be cyanoalkyl groups. In yet another aspect, R1 may be F, R.sup.2 and R.sup.3 may both be alkyl, and R.sup.4 may be cyanoalkyl. Additionally, in a further aspect of the invention, R.sup.1 may be F, R.sup.2 may be alkyl, and R.sup.3 and R.sup.4 may both be cyanoalkyl.

    [0117] Examples of fluorosilicon nitrile compounds in accordance with the present invention are shown in Table I. Each of these compounds may be synthesized from known chlorosilicon nitrile compounds containing Cl atoms, rather than F atoms, substituted on the silicon atom, using the fluorination methods described elsewhere herein.

    TABLE-US-00001 TABLE I Compound # Structure Empirical Formula  1 [00001]embedded image C.sub.6H.sub.12NSiF  2 [00002]embedded image C.sub.5H.sub.9NSiF.sub.2  3 [00003]embedded image C.sub.5H.sub.9NSiF.sub.2  4 [00004]embedded image C.sub.5H.sub.9NSiF.sub.2  5 [00005]embedded image C.sub.5H.sub.9NSiF.sub.2  6 [00006]embedded image C.sub.7H.sub.14NSiF  7 [00007]embedded image C.sub.7H.sub.14NSiF  8 [00008]embedded image C.sub.7H.sub.14NSiF  9 [00009]embedded image C.sub.8H.sub.12N.sub.2SiF.sub.2 10 [00010]embedded image C.sub.7H.sub.11N.sub.2SiF 11 [00011]embedded image C.sub.7H.sub.11N.sub.2SiF 12 [00012]embedded image C.sub.6H.sub.8N.sub.2SiF.sub.2 13 [00013]embedded image C.sub.9H.sub.18NSiF 14 [00014]embedded image C.sub.8H.sub.15NSiF.sub.2 15 [00015]embedded image C.sub.10H.sub.20NSiF 16 [00016]embedded image C.sub.6H.sub.11NSiF.sub.2

    [0118] Additional exemplary fluorosilicon nitrile compounds illustrative of the present invention are shown in Table II. These compounds contain one or two fluorine atoms attached to a silicon atom, a cyanoalkyl group attached to the silicon atom, and one or two methyl groups attached to the silicon atom. Also within the scope of the present invention are fluorosilicon compounds homologous or analogous to those shown in Table II in which the methyl group (in the case of the difluoromethylsilicon nitriles) or one or both of the methyl groups (in the case of the fluorodimethylsilicon nitriles) is or are substituted by an alkyl group other than methyl, in particular a branched or straight chain C2-C8 alkyl group such as ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and the like.

    TABLE-US-00002 TABLE II Fluorodimethylsilicon Difluoromethylsilicon Compound # Nitrile Nitrile 21 [00017]embedded image   21a = C.sub.6H.sub.12NSiF [00018]embedded image   21b = C.sub.5H.sub.9NSiF.sub.2 [00019]embedded image   21c = C.sub.6H.sub.12NSiF [00020]embedded image   21d = C.sub.5H.sub.9NSiF.sub.2 22 [00021]embedded image   22a = C.sub.7H.sub.11N.sub.2SiF [00022]embedded image   22b = C.sub.6H.sub.8N.sub.2SiF.sub.2 [00023]embedded image   22c = C.sub.7H.sub.11N.sub.2SiF [00024]embedded image   22d = C.sub.6H.sub.8N.sub.2SiF.sub.2 23 [00025]embedded image   23a = C.sub.7H.sub.11N.sub.2SiF [00026]embedded image   23b = C.sub.6H.sub.8N.sub.2SiF.sub.2 [00027]embedded image   23c = C.sub.7H.sub.11N.sub.2SiF [00028]embedded image   23d = C.sub.6H.sub.8N.sub.2SiF.sub.2 24 [00029]embedded image   24a = C.sub.7H.sub.11N.sub.2SiF [00030]embedded image   24b = C.sub.6H.sub.8N.sub.2SiF.sub.2 [00031]embedded image   24c = C.sub.7H.sub.11N.sub.2SiF [00032]embedded image   24d = C.sub.6H.sub.8N.sub.2SiF.sub.2 25 [00033]embedded image   25a = C.sub.7H.sub.11N.sub.2SiF [00034]embedded image   25b = C.sub.6H.sub.8N.sub.2SiF.sub.2 [00035]embedded image   25c = C.sub.7H.sub.11N.sub.2SiF [00036]embedded image   25d = C.sub.6H.sub.8N.sub.2SiF.sub.2 26 [00037]embedded image   26a = C.sub.7H.sub.14NSiF [00038]embedded image   26b = C.sub.6H.sub.11NSiF.sub.2 [00039]embedded image   26c = C.sub.7H.sub.14NSiF [00040]embedded image   26d = C.sub.6H.sub.11NSiF.sub.2 27 [00041]embedded image   27a = C.sub.7H.sub.14NSiF [00042]embedded image   27b = C.sub.6H.sub.11NSiF.sub.2 [00043]embedded image   27c = C.sub.7H.sub.14NSiF [00044]embedded image   27d = C.sub.6H.sub.11NSiF.sub.2 28 [00045]embedded image   28a = C.sub.7H.sub.14NSiF [00046]embedded image   28b = C.sub.6H.sub.11NSiF.sub.2 [00047]embedded image   28c = C.sub.7H.sub.14NSiF [00048]embedded image   28d = C.sub.6H.sub.11NSiF.sub.2 29 [00049]embedded image   29a = C.sub.7H.sub.14NSiF [00050]embedded image   29b = C.sub.6H.sub.11NSiF.sub.2 [00051]embedded image   29c = C.sub.7H.sub.14NSiF [00052]embedded image   29d = C.sub.6H.sub.11NSiF.sub.2 30 [00053]embedded image   30a = C.sub.7H.sub.14NSiF [00054]embedded image   30b = C.sub.6H.sub.11NSiF.sub.2 31 [00055]embedded image   31a = C.sub.7H.sub.14NSiF [00056]embedded image   31c = C.sub.6H.sub.11NSiF.sub.2 [00057]embedded image   31b = C.sub.7H.sub.14NSiF 32 [00058]embedded image   32a = C.sub.7H.sub.14NSiF [00059]embedded image   32b = C.sub.6H.sub.11NSiF.sub.2 33 [00060]embedded image   33 = C.sub.7H.sub.14NSiF 34 [00061]embedded image   34a = C.sub.8H.sub.16NSiF [00062]embedded image   34b = C.sub.7H.sub.13NSiF.sub.2 [00063]embedded image   34c = C.sub.8H.sub.16NSiF [00064]embedded image   34d = C.sub.7H.sub.13NSiF.sub.2 35 [00065]embedded image   35a = C.sub.8H.sub.16NSiF [00066]embedded image   35b = C.sub.7H.sub.13NSiF.sub.2 [00067]embedded image   35c = C.sub.8H.sub.16NSiF [00068]embedded image   35d = C.sub.7H.sub.13NSiF.sub.2 36 [00069]embedded image   36a = C.sub.8H.sub.16NSiF [00070]embedded image   36b = C.sub.7H.sub.13NSiF.sub.2 [00071]embedded image   36c = C.sub.8H.sub.16NSiF [00072]embedded image   36d = C.sub.7H.sub.13NSiF.sub.2 37 [00073]embedded image   37a = C.sub.8H.sub.16NSiF [00074]embedded image   37b = C.sub.7H.sub.13NSiF.sub.2 38 [00075]embedded image   38a = C.sub.8H.sub.16NSiF [00076]embedded image   38b = C.sub.7H.sub.13NSiF.sub.2 [00077]embedded image   38c = C.sub.8H.sub.16NSiF [00078]embedded image   38d = C.sub.7H.sub.13NSiF.sub.2 39 [00079]embedded image   39a = C.sub.8H.sub.16NSiF [00080]embedded image   39b = C.sub.7H.sub.13NSiF.sub.2 [00081]embedded image   39c = C.sub.8H.sub.16NSiF [00082]embedded image   39d = C.sub.7H.sub.13NSiF.sub.2 40 [00083]embedded image   40a = C.sub.8H.sub.16NSiF [00084]embedded image   40b = C.sub.7H.sub.13NSiF.sub.2 41 [00085]embedded image   41a = C.sub.8H.sub.16NSiF [00086]embedded image   41b = C.sub.7H.sub.13NSiF.sub.2 [00087]embedded image   41c = C.sub.8H.sub.16NSiF [00088]embedded image   41d = C.sub.7H.sub.13NSiF.sub.2 42 [00089]embedded image   42a = C.sub.8H.sub.16NSiF [00090]embedded image   42b = C.sub.7H.sub.13NSiF.sub.2 [00091]embedded image   42c = C.sub.8H.sub.16NSiF [00092]embedded image   42d = C.sub.7H.sub.13NSiF.sub.2 43 [00093]embedded image   43a = C.sub.8H.sub.16NSiF [00094]embedded image   43b = C.sub.7H.sub.13NSiF.sub.2 44 [00095]embedded image   44a = C.sub.8H.sub.16NSiF [00096]embedded image   44b = C.sub.7H.sub.13NSiF.sub.2 [00097]embedded image   44c = C.sub.8H.sub.16NSiF [00098]embedded image   44d = C.sub.7H.sub.13NSiF.sub.2 45 [00099]embedded image   45a = C.sub.8H.sub.16NSiF [00100]embedded image   45b = C.sub.7H.sub.13NSiF.sub.2 [00101]embedded image   45c = C.sub.8H.sub.16NSiF [00102]embedded image   45d = C.sub.7H.sub.13NSiF.sub.2 46 [00103]embedded image   46a = C.sub.8H.sub.16NSiF [00104]embedded image   46b = C.sub.7H.sub.13NSiF.sub.2 47 [00105]embedded image   47a = C.sub.8H.sub.16NSiF [00106]embedded image   47b = C.sub.7H.sub.13NSiF.sub.2 [00107]embedded image   47c = C.sub.8H.sub.16NSiF [00108]embedded image   47d = C.sub.7H.sub.13NSiF.sub.2 48 [00109]embedded image   48a = C.sub.8H.sub.16NSiF [00110]embedded image   48b = C.sub.7H.sub.13NSiF.sub.2 49 [00111]embedded image   49a = C.sub.8H.sub.16NSiF [00112]embedded image   49b = C.sub.7H.sub.13NSiF.sub.2 50 [00113]embedded image   50a = C.sub.8H.sub.16NSiF [00114]embedded image   50b = C.sub.7H.sub.13NSiF.sub.2 51 [00115]embedded image   51a = C.sub.8H.sub.16NSiF [00116]embedded image   51b = C.sub.7H.sub.13NSiF.sub.2 52 [00117]embedded image   52a = C.sub.8H.sub.16NSiF [00118]embedded image   52b = C.sub.7H.sub.13NSiF.sub.2 53 [00119]embedded image   53a = C.sub.9H.sub.15N.sub.2SiF [00120]embedded image   53b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00121]embedded image   53c = C.sub.9H.sub.15N.sub.2SiF [00122]embedded image   53d = C.sub.8H.sub.12N.sub.2SiF.sub.2 54 [00123]embedded image   54a = C.sub.9H.sub.15N.sub.2SiF [00124]embedded image   54b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00125]embedded image   54c = C.sub.9H.sub.15N.sub.2SiF [00126]embedded image   54d = C.sub.8H.sub.12N.sub.2SiF.sub.2 55 [00127]embedded image   55a = C.sub.9H.sub.15N.sub.2SiF [00128]embedded image   55b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00129]embedded image   55c = C.sub.9H.sub.15N.sub.2SiF [00130]embedded image   55d = C.sub.8H.sub.12N.sub.2SiF.sub.2 56 [00131]embedded image   56a = C.sub.9H.sub.15N.sub.2SiF [00132]embedded image   56b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00133]embedded image   56c = C.sub.9H.sub.15N.sub.2SiF [00134]embedded image   56d = C.sub.8H.sub.12N.sub.2SiF.sub.2 57 [00135]embedded image   57a = C.sub.9H.sub.15N.sub.2SiF [00136]embedded image   57b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00137]embedded image   57c = C.sub.9H.sub.15N.sub.2SiF [00138]embedded image   57d = C.sub.8H.sub.12N.sub.2SiF.sub.2 58 [00139]embedded image   58a = C.sub.9H.sub.15N.sub.2SiF [00140]embedded image   58b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00141]embedded image   58c = C.sub.9H.sub.15N.sub.2SiF [00142]embedded image   58d = C.sub.8H.sub.12N.sub.2SiF.sub.2 59 [00143]embedded image   59a = C.sub.9H.sub.15N.sub.2SiF [00144]embedded image   59b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00145]embedded image   59c = C.sub.9H.sub.15N.sub.2SiF [00146]embedded image   59d = C.sub.8H.sub.12N.sub.2SiF.sub.2 60 [00147]embedded image   60a = C.sub.9H.sub.15N.sub.2SiF [00148]embedded image   60b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00149]embedded image   60c = C.sub.9H.sub.15N.sub.2SiF [00150]embedded image   60d = C.sub.8H.sub.12N.sub.2SiF.sub.2 61 [00151]embedded image   61a = C.sub.9H.sub.15N.sub.2SiF [00152]embedded image   61b = C.sub.8H.sub.12N.sub.2SiF.sub.2 62 [00153]embedded image   62a = C.sub.9H.sub.15N.sub.2SiF [00154]embedded image   62b = C.sub.8H.sub.12N.sub.2SiF.sub.2 63 [00155]embedded image   63a = C.sub.9H.sub.15N.sub.2SiF [00156]embedded image   63b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00157]embedded image   63c = C.sub.9H.sub.15N.sub.2SiF [00158]embedded image   63d = C.sub.8H.sub.12N.sub.2SiF.sub.2 64 [00159]embedded image   64a = C.sub.9H.sub.15N.sub.2SiF [00160]embedded image   64b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00161]embedded image   64c = C.sub.9H.sub.15N.sub.2SiF [00162]embedded image   64d = C.sub.8H.sub.12N.sub.2SiF.sub.2 65 [00163]embedded image   65a = C.sub.9H.sub.15N.sub.2SiF [00164]embedded image   65b = C.sub.8H.sub.12N.sub.2SiF.sub.2 66 [00165]embedded image   66a = C.sub.9H.sub.15N.sub.2SiF [00166]embedded image   66b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00167]embedded image   66c = C.sub.9H.sub.15N.sub.2SiF [00168]embedded image   66d = C.sub.8H.sub.12N.sub.2SiF.sub.2 67 [00169]embedded image   67a = C.sub.9H.sub.15N.sub.2SiF [00170]embedded image   67b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00171]embedded image   67c = C.sub.9H.sub.15N.sub.2SiF [00172]embedded image   67d = C.sub.8H.sub.12N.sub.2SiF.sub.2 68 [00173]embedded image   68a = C.sub.9H.sub.15N.sub.2SiF [00174]embedded image   68b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00175]embedded image   68c = C.sub.9H.sub.15N.sub.2SiF [00176]embedded image   68d = C.sub.8H.sub.12N.sub.2SiF.sub.2 69 [00177]embedded image   69a = C.sub.9H.sub.15N.sub.2SiF [00178]embedded image   69b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00179]embedded image   69c = C.sub.9H.sub.15N.sub.2SiF [00180]embedded image   69d = C.sub.8H.sub.12N.sub.2SiF.sub.2 70 [00181]embedded image   70a = C.sub.9H.sub.15N.sub.2SiF [00182]embedded image   70b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00183]embedded image   70c = C.sub.9H.sub.15N.sub.2SiF [00184]embedded image   70d = C.sub.8H.sub.12N.sub.2SiF.sub.2 71 [00185]embedded image   71a = C.sub.9H.sub.15N.sub.2SiF [00186]embedded image   71b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00187]embedded image   71c = C.sub.9H.sub.15N.sub.2SiF [00188]embedded image   71d = C.sub.8H.sub.12N.sub.2SiF.sub.2 72 [00189]embedded image   72a = C.sub.9H.sub.15N.sub.2SiF [00190]embedded image   72b = C.sub.8H.sub.12N.sub.2SiF.sub.2 73 [00191]embedded image   73a = C.sub.9H.sub.15N.sub.2SiF [00192]embedded image   73b = C.sub.8H.sub.12N.sub.2SiF.sub.2 [00193]embedded image   73c = C.sub.9H.sub.15N.sub.2SiF [00194]embedded image   73d = C.sub.8H.sub.12N.sub.2SiF.sub.2 74 [00195]embedded image   74a = C.sub.9H.sub.15N.sub.2SiF [00196]embedded image   74b = C.sub.8H.sub.12N.sub.2SiF.sub.2

    [0119] Also provided by the present invention are methods of making the above-mentioned fluorosilicon nitrile compounds.

    [0120] In one aspect of the invention, a method is provided which 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. 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. The chlorosilicon nitrile compound may correspond to general formula Si(R.sup.1)(R.sup.2)(R.sup.3)(R.sup.4), wherein one or two of R.sup.1-R.sup.4 are chlorine atoms, one or two of R.sup.1-R.sup.4 are cyanoalkyl groups, which are the same as or different from each other where two cyanoalkyl groups are present, and the remaining R.sup.1-R.sup.4, if any, are alkyl groups.

    [0121] The fluorinating agent may, for example, be selected from the group consisting of HF, MF, MHF.sub.2 and SbF.sub.3, where M is Na, K, Rb, Cs or NH.sub.4. Fluorides of antimony, zinc, lead, mercury, silver, cobalt, copper, tungsten and other metals may be utilized as the fluorinating agent. Sodium fluoroborate may also be used, as can mixtures of SbF.sub.3 and BF.sub.3 or NaF and sulfuric acid. Other suitable fluorinating agents include neat BF.sub.3, BF.sub.3 etherates, Na.sub.2SiF.sub.6, NaPF.sub.6, NaSbF.sub.6, NaBF.sub.4, Me.sub.3SnF, PF.sub.5, PhCBF.sub.4, NOBF.sub.4, and NO.sub.2BF.sub.4. If HF (hydrogen fluoride) is employed, it may be used in anhydrous form or in an aqueous-alcoholic or aqueous medium. Potassium hydrogen difluoride and ammonium hydrogen difluoride (ammonium bifluoride) are especially useful fluorinating agents.

    [0122] Certain of the chlorosilicon nitrile compounds useful as the starting material in the aforementioned fluorination reaction are known compounds that may be prepared using methods known in the art. Such compounds include, for example, compounds having the following CAS registration numbers: 42759-42-2; 59343-99-6; 42759-43-3; 100792-00-5; 1068-40-2; 18243-57-7; 1274903-71-7; 876343-97-4; 2617-09-6; 18276-25-0; 18135-77-8; 103613-06-5; 1071-17-6; 18727-31-6; 7031-17-6; 169206-21-7; 875478-07-2; 161582-95-2; 113641-37-5; and 1186-40-9. Additional chlorosilicon nitrile compounds may be readily synthesized by hydrosilylation of an alkene with a chloroalkylsilane. In one embodiment of such a synthesis, the alkene is a cyanoalkene. The cyanoalkene may suitably be a C3-C10 cyanoalkene, for example, and may contain a single carbon-carbon double bond and one, two or more cyano (—CN) groups per molecule. The structure of the cyanoalkene is selected so as to provide a cyanoalkyl group of the type desired in the fluorosilicon nitrile produced by hydrosilylation. Illustrative examples of suitable cyanoalkenes include, but are not limited to, CH.sub.3CH═CHCN (CAS 4786-20-3); CH.sub.3C(CN)═CHCN (CAS 70240-55-0); NCCH.sub.2CH═CHCN (CAS 7717-24-0); CH.sub.3CH═C(CN).sub.2 (CAS 1508-07-2); CH.sub.2═C(CN)CH.sub.2CN (CAS 24412-94-0); CH.sub.3CH.sub.2CH═CHCN (CAS 13284-42-9); CH.sub.2═CHCH.sub.2CH.sub.2CN (CAS 592-51-8); CH.sub.3CH═CHCH.sub.2CN (CAS 4635-87-4); CH.sub.3CH═C(CN)CH.sub.3 (CAS 4403-61-6); CH.sub.2═C(CN)CH.sub.2CH.sub.3 (CAS 1647-11-6); CH.sub.2═C(CH.sub.3)CH.sub.2CN (CAS 4786-19-0); (CH.sub.3).sub.2C═CHCN (CAS 4786-24-7); CH.sub.2═CHCH(CN)CH.sub.3 (CAS 16529-56-9); CH.sub.2═C(CH.sub.2CN)CH.sub.2CH.sub.3 (CAS 1462956-36-0); CH.sub.2═CHCH(CN)CH.sub.2CH.sub.3 (CAS 180974-28-1); CH.sub.2═CHCH.sub.2CH(CN)CH.sub.3 (CAS 89464-18-6); CH.sub.3CH.sub.2C(CN)═CHCH.sub.3 (CAS 89580-25-6); CH.sub.2═CHCH(CH.sub.3)CH.sub.2CN (CAS 51980-04-2); CH.sub.2═CHC(CH.sub.3).sub.2CN (CAS 41405-16-7); CH.sub.3CH(CN)CH═CHCH.sub.3 (CAS 37674-62-7); CH.sub.2═C(CH.sub.3)CH.sub.2CH.sub.2CN (CAS 34998-36-2); CH.sub.3CH.sub.2CH═CHCH.sub.2CN (CAS 16170-44-8); CH.sub.3CH.sub.2CH.sub.2CH═CHCN (CAS 5636-69-1); CH.sub.2═CHCH.sub.2CH.sub.2CH.sub.2CN (CAS 5048-19-1); (CH.sub.3).sub.2C═C(CH.sub.3)CN (CAS 4786-37-2); (CH.sub.3).sub.2C═CHCH.sub.2CN (CAS 4786-23-6); CH.sub.2═C(CN)CH.sub.2CH.sub.2CH.sub.3 (CAS 3931-57-5); CH.sub.2═C(CN)CH(CH.sub.3).sub.2(CAS 2813-69-6); CH.sub.3CH.sub.2CH.sub.2CH═CHCN (CAS 67889-07-0); CH.sub.2═C(CH.sub.3)CH(CN)CH.sub.3 (CAS 25653-08-1); (CH.sub.3).sub.2CHCH═CHCN (CAS 19124-15-3); CH.sub.3CH.sub.2C(CH.sub.3)═CHCN (CAS 14799-77-0); CH.sub.3C(CN)═C(CN)CH.sub.2CH.sub.3 (CAS 1003003-54-0); NCCH.sub.2CH.sub.2CH.sub.2CH═CHCN (CAS 872307-67-0); CH.sub.2═C(CN)CH.sub.2CH.sub.2CH.sub.2CN (CAS 856347-40-5); CH.sub.3CH.sub.2C(CH.sub.3)═C(CN).sub.2 (CAS 13017-50-0); (CH.sub.3).sub.2CHCH═C(CN).sub.2 (CAS 13134-03-7); CH.sub.3CH═C(CN)CH.sub.2CH.sub.2CN (CAS 22485-88-7); CH.sub.2═C(CN)CH.sub.2CH(CN)CH.sub.3 (CAS 35299-21-9); CH.sub.2═CHCH.sub.2CH(CN)CH.sub.2CN (CAS 364453-09-5); CH.sub.3CH═CHCH(CN)CH.sub.2CN (CAS 36453-10-8); CH.sub.3CH.sub.2CH═C(CN)CH.sub.2CN (CAS 36453-11-9); (CH.sub.3).sub.2C═C(CN)CH.sub.2CN (CAS 67386-03-2); NCCH.sub.2C(CH.sub.3)═CHCH.sub.2CN (CAS 76257-96-0); CH.sub.2═C(CH.sub.2CN)CH.sub.2CH.sub.2CN (CAS 80718-20-3); CH.sub.2═C(CH.sub.2CN)CH(CN)CH.sub.3 (CAS 80718-26-9); CH.sub.3CH.sub.2CH.sub.2CH═C(CN).sub.2 (CAS 87948-15-0); CH.sub.3CH(CN)CH═CHCH.sub.2CN (CAS 122917-04-8); (NC).sub.2CHCH.sub.2CH═CHCH.sub.3 (CAS 130575-29-0); CH.sub.2═C(CH.sub.3)CH.sub.2CH(CN).sub.2 (CAS 145050-18-6); CH.sub.2═CHCH.sub.2C(CN).sub.2CH.sub.3 (CAS 154657-02-0); (CH.sub.3).sub.2C═CHCH(CN).sub.2 (CAS 442661-89-4); CH.sub.2═CHCH(CH.sub.3)CH(CN).sub.2 (CAS 443124-95-6); and CH.sub.2═CHCH.sub.2CH.sub.2CH(CN).sub.2 (CAS 475197-78-5).

    [0123] The chloroalkylsilane may be a silane containing, as substituents attached to the silicon atom, one or two hydrogen atoms, one chlorine atom and one or two alkyl groups, which may be the same as each other or different from each other. Where one hydrogen atom is present, one molecule of cyanoalkene reacts with one molecule of chloroalkylsilane in the hydrosilylation reaction, thereby introducing a single cyanoalkyl group into the silane. When two hydrogen atoms are present, two molecules of cyanoalkene react with one molecule of chloroalkylsilane, thereby introducing two cyanoalkyl groups into the silane. In this embodiment, the chloroalkyl silane may correspond to the general structure SiCl(H).sub.n(R).sub.3-n, where n is 1 or 2 and R is alkyl. In another aspect of the invention, the chloroalkyl silane may be a silane containing, as substituents attached to the silicon atom, one or two hydrogen atoms, two chlorine atoms, and, where only one hydrogen atom is attached to silicon, a single alkyl group. In this embodiment, the chloroalkyl silane may correspond to the general structure SiCl.sub.2(H).sub.n(R).sub.2-n, where n is 1 or 2 and R, if present, is alkyl. Where one hydrogen atom is present, one molecule of cyanoalkene reacts with one molecule of chloroalkylsilane in the hydrosilylation reaction, thereby introducing a single cyanoalkyl group into the silane. When two hydrogen atoms are present, two molecules of alkene react with one molecule of chloroalkylsilane, thereby introducing two cyanoalkyl groups into the silane.

    [0124] The alkyl groups may, for example, be a C1-C8 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl and isomers thereof, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, n-octyl and isomers thereof and combinations of such alkyl groups. The chloroalkylsilane thus may correspond to the general formula HSi(R.sup.1)(R.sup.2)(R.sup.3), wherein one or two of R.sup.1-R.sup.3 are chlorine atoms and the remaining R.sup.1-R.sup.3 are alkyl groups, which may be the same as or different from each other where more than one alkyl group per molecule is present.

    [0125] An example of such a synthetic reaction scheme is shown below. In this example, the alkene 2-cyanobut-1-ene (CAS #1647-11-6) is hydrosilylated with chlorodimethylsilane (CDMS), leading to a chlorosilicon nitrile having the structure shown (Reaction 1A). The chlorosilicon nitrile is then reacted with a fluorinating agent to produce fluorosilicon nitrile compound 30a having the structure shown (Reaction 1B).

    ##STR00197##

    [0126] A further method of making a fluorosilicon nitrile compound in accordance with the present invention comprises hydrosilylation of an alkene with a fluoroalkylsilane (i.e., reacting the alkene and fluoroalkylsilane under hydrosilylation conditions). The reacted alkene may be a cyanoalkene, for example. Suitable cyanoalkenes include any of the previously mentioned cyanoalkenes.

    [0127] The fluoroalkylsilane may be a silane containing, as substituents attached to the silicon atom, one or two hydrogen atoms, one fluorine atom and one or two alkyl groups, which may be the same as each other or different from each other. The total number of hydrogen atoms, fluorine atom, and alkyl groups equals four. Where one hydrogen atom attached to silicon is present, one molecule of cyanoalkene reacts with one molecule of fluoroalkylsilane in the hydrosilylation reaction, thereby introducing a single cyanoalkyl group into the silane. When two hydrogen atoms attached to silicon are present, two molecules of cyanoalkene react with one molecule of fluoroalkylsilane, thereby introducing two cyanoalkyl groups into the silane. In this embodiment, the fluoroalkyl silane may correspond to the general structure SiF(H).sub.n(R).sub.3-n, where n is 1 or 2 and R is alkyl. In another aspect of the invention, the fluoroalkyl silane may be a silane containing, as substituents attached to the silicon atom, one or two hydrogen atoms, two fluorine atoms, and, where only one hydrogen atom is attached to silicon, a single alkyl group. The total number of hydrogen atoms, fluorine atoms and alkyl group equals four. In this embodiment, the fluoroalkyl silane may correspond to the general structure SiF.sub.2(H).sub.n(R).sub.2-n, where n is 1 or 2 and R, if present, is alkyl. Where one hydrogen atom attached to silicon is present, one molecule of cyanoalkene reacts with one molecule of fluoroalkylsilane in the hydrosilylation reaction, thereby introducing a single cyanoalkyl group into the silane. When two hydrogen atoms attached to silicon are present, two molecules of cyanoalkene react with one molecule of fluoroalkylsilane, thereby introducing two cyanoalkyl groups into the silane.

    [0128] The alkyl groups may, for example, be a C1-C8 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl and isomers thereof, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, n-octyl and isomers thereof and combinations of such alkyl groups.

    [0129] The fluoroalkylsilane thus may correspond to the general formula HSi(R.sup.1)(R.sup.2)(R.sup.3), wherein one or two of R.sup.1-R.sup.3 are fluorine atoms and the remaining R.sup.1-R.sup.3 are alkyl groups, which may be the same as or different from each other where more than one alkyl group per molecule is present.

    [0130] The following reaction scheme (Reaction 1C) is an example of such a reaction. In this example, fluorosilicon nitrile compound 30a is prepared by direct hydrosilylation of the alkene 2-cyanobut-1-ene with fluorodimethylsilane (FDMS).

    ##STR00198##

    [0131] In one embodiment of the invention, the above-mentioned hydrosilylation reactions are carried out in the presence of a hydrosilylation catalyst, in particular an organoplatinum coordination complex having activity as a hydrosilylation catalyst. Karstedt's catalyst, which is an organoplatinum compound derived from divinyl-containing disiloxane (by treatment of chloroplatinic acid with divinyltetramethyldisiloxane), is an example of a suitable catalyst for this purpose. Other suitable hydrosilylation catalysts include, for example, Wilkinson's catalyst (tris(triphenylphosphone)rhodium (I) chloride), the cobalt carbonyl complex Co.sub.2(CO).sub.8, and H.sub.2PtCl.sub.6 (Speier's catalyst). Hydrosilylation typically proceeds in an anti-Markovnikov manner. However, depending upon the reaction conditions used, hydrosilylation may not be completely selective; that is, a mixture of isomeric hydrosilylation products may be obtained. The individual components of such reaction product mixtures may be purified and isolated using any conventionally known techniques, such as fractional distillation. Alternatively, the mixture of components may be utilized for the desired end use without such fractionation or separation.

    [0132] Typically, where it is desired to introduce a single cyanoalkyl group into a silane, the molar ratio of cyanoalkene to fluoroalkylsilane may be approximately 1:1, e.g., from about 0.7:1 to about 1.3:1. If it is desired to introduce two cyanoalkyl groups, the molar ratio of cyanoalkene to fluoroalkylsilane may be approximately 2:1, e.g., from about 1.5:1 to about 2.5:1. The hydrosilylation may be carried out using an organic solvent, e.g., an aromatic hydrocarbon, as a reaction medium. The mixture of cyanoalkene, fluoroalkylsilane, hydrosilylation catalyst and optional solvent may be heated for a time and at a temperature effective to provide the desired conversion of the starting materials. For example, reaction temperatures of from about 50° C. to about 110° C. and reaction times of from about 1 to about 6 hours may be utilized.

    [0133] Aspects of the present invention include: [0134] 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; [0135] subject to the proviso that the fluorosilicon nitrile compound is not SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH(CN)CH.sub.3); SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH.sub.2CN); SiF.sub.2(CH.sub.3)(CH.sub.2CH(CH.sub.3)CH.sub.2CN); or SiF.sub.2[CH.sub.2CH(CH.sub.3)CH.sub.2CN].sub.2. [0136] 2. 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. [0137] 3. 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. [0138] 4. 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. [0139] 5. 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. [0140] 6. The fluorosilicon nitrile compound of any one of the preceding claims, wherein the cyanoalkyl groups are C2-C9 cyanoalkyl groups. [0141] 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. [0142] 8. The fluorosilicon nitrile compound of any one of the preceding claims, wherein the cyanoalkyl group or cyanoalkyl groups contain(s) a single cyano group per cyanoalkyl group. [0143] 9. The fluorosilicon nitrile compound of any one of claims 1 through 7, wherein the cyanoalkyl group or cyanoalkyl groups contain(s) two cyano groups per cyanoalkyl group. [0144] 10. The fluorosilicon nitrile compound of any one of the preceding claims, wherein the cyanoalkyl group or cyanoalkyl groups contain(s) a cyano group which is substituted at a terminal position of an alkyl radical. [0145] 11. The fluorosilicon nitrile compound of any one of the preceeding claims, wherein the cyanoalkyl group or cyanoalkyl groups contain(s) a cyano group which is substituted at an internal position of an alkyl radical. [0146] 12. The fluorosilicon nitrile compound of any one of the preceding claims, wherein the cyanoalkyl group or cyanoalkyl groups are selected from the group consisting of: [0147] —CH.sub.2CH(CN)CH.sub.3; [0148] —CH(CN)CH.sub.2CH.sub.3; [0149] —C(CN)(CH.sub.3).sub.2; [0150] —CH.sub.2CH.sub.2CN; [0151] —CH(CN)CH.sub.3; [0152] —CH.sub.2CH.sub.2CH(CN)CH.sub.3; [0153] —CH.sub.2CH(CN)CH.sub.2CH.sub.3; [0154] —(CH.sub.2).sub.3CN; [0155] —(CH.sub.2).sub.2CN; [0156] —(CH.sub.2).sub.4CN; [0157] —(CH.sub.2).sub.5CN; [0158] —(CH.sub.2).sub.3C(CN).sub.2CH.sub.3; [0159] —CH(CH.sub.3)CH.sub.2CN; [0160] —CH(CN)CH(CN)CH.sub.3; [0161] —C(CN)(CH.sub.3)CH.sub.2CN; [0162] —CH(CH.sub.2CN).sub.2; [0163] —CH(CN)CH.sub.2CH.sub.2CN; [0164] —CH(CH.sub.3)CH(CN).sub.2; [0165] —C(CN).sub.2(CH.sub.2CH.sub.3); [0166] —CH.sub.2CH(CN)CH.sub.2CN; [0167] —C(CN)(CH.sub.3)CH.sub.2CN; [0168] —CH(CH.sub.2CH.sub.3)CH.sub.2CN; [0169] —CH(CN)CH.sub.2CH.sub.2CH.sub.3; [0170] —CH(CH.sub.3)CH.sub.2CH.sub.2CN; [0171] —CH(CH.sub.2CN)CH.sub.2CH.sub.3; [0172] —CH(CH.sub.3)CH(CN)CH.sub.3; [0173] —C(CN)(CH.sub.3)CH.sub.2CH.sub.3; [0174] —CH.sub.2CH(CH.sub.3)CH.sub.2CN; [0175] —C(CH.sub.3).sub.2CH.sub.2CN; [0176] —CH(CN)CH(CH.sub.3).sub.2; [0177] —CH.sub.2CH.sub.2CH(CN)CH.sub.3; [0178] —CH.sub.2CH(CH.sub.2CN)CH.sub.2CH.sub.3; [0179] —C(CH.sub.3)(CH.sub.2CH.sub.3)CH.sub.2CN; [0180] —CH.sub.2CH.sub.2CH(CN)CH.sub.2CH.sub.3; [0181] —CH(CH.sub.3)CH(CN)CH.sub.2CH.sub.3; [0182] —CH.sub.2CH.sub.2CH.sub.2CH(CN)CH.sub.3; [0183] —CH(CH.sub.3)CH.sub.2CH(CN)CH.sub.3; [0184] —C(CH.sub.2CH.sub.3).sub.2(CN); [0185] —CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CN; [0186] —CH(CH.sub.3)CH(CH.sub.3)CH.sub.2CN; [0187] —(CH.sub.2).sub.2C(CH.sub.3).sub.2CN; [0188] —CH(CH.sub.3)C(CH.sub.3).sub.2CN; [0189] —CH(CH.sub.2CH.sub.3)CH(CN)CH.sub.3; [0190] —CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2CN; [0191] —C(CH.sub.3).sub.2CH.sub.2CH.sub.2CN; [0192] —CH(CH.sub.2CH.sub.3)CH.sub.2CH.sub.2CN; [0193] —CH(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.3; [0194] —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.3; [0195] —CH(CH.sub.3)CH.sub.2CH.sub.2CH.sub.2CN; [0196] —C(CH.sub.3).sub.2CH(CN)CH.sub.3; [0197] —C(CH.sub.3)(CN)CH(CH.sub.3).sub.2; [0198] —CH(CH.sub.2CN)CH(CH.sub.3).sub.2; [0199] —CH.sub.2CH(CN)CH.sub.2CH.sub.2CH.sub.3; [0200] —C(CH.sub.3)(CN)CH.sub.2CH.sub.2CH.sub.3; [0201] —CH.sub.2CH(CN)CH(CH.sub.3).sub.2; [0202] —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.3; [0203] —CH.sub.2CH(CH.sub.3)CH(CN)CH.sub.3; [0204] —CH(CN)CH.sub.2CH(CH.sub.3).sub.2; [0205] —CH(CN)CH(CH.sub.3)CH.sub.2CH.sub.3; [0206] —C(CH.sub.3)(CN)CH(CN)CH.sub.2CH.sub.3; [0207] —C(CN)(CH.sub.2CH.sub.3)CH(CN)CH.sub.3; [0208] —CH(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.2CN; [0209] —CH(CN)CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN; [0210] —CH.sub.2CH(CN)CH.sub.2CH.sub.2CH.sub.2CN; [0211] —C(CH.sub.3)(CN)CH.sub.2CH.sub.2CH.sub.2CN; [0212] —C(CH.sub.3)(CH.sub.2CH.sub.3)CH(CN).sub.2; [0213] —C(CN).sub.2CH(CH.sub.3)CH.sub.2CH.sub.3; [0214] —C(CN).sub.2CH.sub.2CH(CH.sub.3).sub.2; [0215] —CH(CH(CN).sub.2)CH(CH.sub.3).sub.2; [0216] —C(CN)(CH.sub.2CH.sub.3)CH.sub.2CH.sub.2CN; [0217] —CH(CH.sub.3)CH(CN)CH.sub.2CH.sub.2CN; [0218] —CH.sub.2CH(CN)CH.sub.2CH(CN)CH.sub.3; [0219] —C(CN)(CH.sub.3)CH.sub.2CH(CN)CH.sub.3; [0220] —(CH.sub.2).sub.3CH(CN)CH.sub.2CN; [0221] —CH(CH.sub.3)CH.sub.2CH(CN)CH.sub.2CN; [0222] —CH(CH.sub.2CH.sub.3)CH(CN)CH.sub.2CN; [0223] —C(CN)(CH.sub.2CN)CH.sub.2CH.sub.2CH.sub.3; [0224] —C(CH.sub.3).sub.2CH(CN)CH.sub.2CN; [0225] —C(CN)(CH.sub.2CN)CH(CH.sub.3).sub.2; [0226] —C(CH.sub.3)(CH.sub.2CN)CH.sub.2CH.sub.2CN; [0227] —CH(CH.sub.2CN)CH(CH.sub.3)CH.sub.2CN; [0228] —CH.sub.2CH(CH.sub.2CN)CH.sub.2CH.sub.2CN; [0229] —CH.sub.2CH(CH.sub.2CN)CH(CN)CH.sub.3; [0230] —C(CH.sub.3)(CH.sub.2CN)CH(CN)CH.sub.3; [0231] —CH(CH(CN).sub.2)CH.sub.2CH.sub.2CH.sub.3; [0232] —C(CN).sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.3; [0233] —CH(CH.sub.2CN)CH.sub.2CH(CN)CH.sub.3; [0234] —CH(CH.sub.2CH.sub.2CN)CH(CN)CH.sub.3; [0235] —CH(CH.sub.3)CH.sub.2CH.sub.2CH(CN).sub.2; [0236] —CH(CH.sub.2CH.sub.3)CH.sub.2CH(CN).sub.2; [0237] —CH.sub.2CH(CH.sub.3)CH.sub.2CH(CN).sub.2; [0238] —C(CH.sub.3).sub.2CH.sub.2CH(CN).sub.2; [0239] —CH.sub.2CH.sub.2CH.sub.2C(CN).sub.2CH.sub.3; [0240] —CH(CH.sub.3)CH.sub.2C(CN).sub.2CH.sub.3; [0241] —CH(CH(CN).sub.2)CH(CH.sub.3).sub.2; [0242] —CH.sub.2CH.sub.2CH(CH.sub.3)CH(CN).sub.2; [0243] —CH(CH.sub.3)CH(CH.sub.3)CH(CN).sub.2; and [0244] —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH(CN).sub.2 and combinations thereof. [0245] 13. 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. [0246] 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. [0247] 15. 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. [0248] 16. The fluorosilicon nitrile compound of claims 12 or 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. [0249] 17. A fluorosilicon nitrile compound of general formula Si(R.sup.1)(R.sup.2)(R.sup.3)(R.sup.4), wherein one or two of R.sup.1-R.sup.4 are fluorine atoms, one or two of R.sup.1-R.sup.4 are cyanoalkyl groups, which are the same as or different from each other where two cyanoalkyl groups are present, and the remaining R.sup.1-R.sup.4, if any, are alkyl groups; subject to the proviso that the fluorosilicon nitrile compound is not SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH(CN)CH.sub.3); SiF.sub.2(CH.sub.3)(CH.sub.2CH.sub.2CH.sub.2CN); SiF.sub.2(CH.sub.3)(CH.sub.2CH(CH.sub.3)CH.sub.2CN); or SiF.sub.2[CH.sub.2CH(CH.sub.3)CH.sub.2CN].sub.2. [0250] 18. A method of making a fluorosilicon nitrile compound in accordance with any one of the preceding claims, 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. [0251] 19. The method of claim 18, wherein the fluorinating agent is selected from the group consisting of HF, MF, MHF.sub.2 and SbF.sub.3, where M is Na, K, Rb, Cs or NH.sub.4. [0252] 20. The method of claims 18 or 19, wherein the chlorosilicon nitrile compound is prepared by hydrosilylation of an alkene with a chloroalkylsilane. [0253] 21. The method of claims 18 through 20, wherein the alkene is a cyanoalkene. [0254] 22. A method of making a fluorosilicon nitrile compound in accordance with any one of the preceding claims, wherein the method comprises hydrosilylation of an alkene with a fluoroalkylsilane. [0255] 23. The method of claim 22, wherein the alkene is a cyanoalkene.

    [0256] Within this specification embodiments have been described in a way which enables a clear and concise specification to be written, but it is intended and will be appreciated that embodiments may be variously combined or separated without parting from the invention. For example, it will be appreciated that all preferred features described herein are applicable to all aspects of the invention described herein.