Method of preparing halogenated silahydrocarbylenes

Patent metadata

Field	Value
Publication number	US-9422316-B2
Application number	US-201314436095-A
Country	US
Kind code	B2
Filing date	Jul 2, 2013
Priority date	Oct 16, 2012
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

A method comprises separate and consecutive steps (i) and (ii). Step (i) includes contacting a copper catalyst with hydrogen gas and a halogenated silane monomer at a temperature of 500° C. to 1400° C. to form a silicon-containing copper catalyst comprising at least 0.1% (w/w) of silicon. Step (ii) includes contacting the silicon-containing copper catalyst with an organohalide at a temperature of 100° C. to 600° C. to form a reaction product. The organohalide has formula H a C b X c , where X is a halogen atom, subscript a is an integer of 0 or more, subscript b is an integer of 1 or more, and subscript c is an integer of 2 or more. The method produces a reaction product. The reaction product includes a halogenated silahydrocarbylene.

First claim

The invention claimed is:

1. A method comprises separate and consecutive steps (i) and (ii), where
Step (i) comprises contacting a copper catalyst with hydrogen gas and a halogenated silane monomer at a temperature of 500° C. to 1400° C. to form a silicon-containing copper catalyst comprising at least 0.1% (w/w) of silicon; and
Step (ii) comprises contacting the silicon-containing copper catalyst with an organohalide at a temperature of 100° C. to 600° C. to form a reaction product comprising a halogenated silahydrocarbylene, where the organohalide has formula H a C b X c , where X is a halogen atom, subscript a is an integer of 0 or more, subscript b is an integer of 1 or more, and subscript c is an integer of 2 or more.

2. The method of claim 1 , where the copper catalyst further comprises at least one element selected from calcium, cesium, gold, magnesium, nickel, sulfur, tin, and zinc.

3. The method of claim 1 , where the halogenated silane monomer comprises a monomer selected from a silicon tetrahalide, a trihalosilane, and a combination thereof.

4. The method of claim 1 , further comprising a third step (iii) in which the separate and consecutive first step (i) and second step (ii) are repeated one or more times.

5. The method of claim 1 , further comprising purging the silicon-containing copper catalyst formed in step (i) with at least one of hydrogen gas and an inert gas before contacting the silicon-containing copper catalyst with the organohalide in step (ii).

6. The method of claim 5 , where the silicon-containing copper catalyst is first purged with hydrogen gas and then subsequently purged with an inert gas.

7. The method of claim 1 , where the copper catalyst further comprises a metal oxide or carbon-based support.

8. The method of claim 1 , where the copper catalyst comprises copper, gold, and magnesium.

9. The method of claim 1 , where a mole ratio of hydrogen gas to halogenated silane monomer is from 15:1 to 1:1.

10. The method of claim 1 , where the organohalide is selected from: 1) an alkyl halide where subscript b is 1 to 10, and 2) a cycloalkyl halide where subscript b is 4 to 10.

11. The method of claim 10 , where the organohalide is an alkyl halide, subscript b is 1, subscript c is 2, 3, or 4, and each X is Cl.

12. The method of claim 1 , where the halogenated silahydrocarbylene has formula X d H e R 1 f Si—R—SiX d H e R 1 f , where each X is independently a halogen atom; each subscript d is independently 0, 1, 2, or 3, with the proviso that at least one instance of d>0; each subscript e is independently 0, 1, or 2; each subscript f is independently 0, 1, or 2; with the proviso that a quantity (d+e+f)=3, each R 1 is independently a monovalent hydrocarbon group, and R is a divalent hydrocarbon group.

13. The method of claim 1 further comprising the step of recovering the halogenated silahydrocarbylene.

14. The method of claim 1 , where the temperature at which the reactants in step (i) contact the copper catalyst is 500° C. to 950° C.

15. The method of claim 1 , where the method further comprises step (iv): forming a resin from the halogenated silahydrocarbylene.

Assignees

• Dow Corning

Inventors

• Dash Aswini K
• Katsoulis Dimitris Elias
• Mclaughlin Matthew J
• Sparschu Wendy

Classifications

• C07F7/125

  by reactions involving both Si-C and Si-halogen linkages, the Si-C and Si-halogen linkages can be to the same or to different Si atoms, e.g. redistribution reactions · CPC title

• C07F7/16 Primary

  Preparation thereof from silicon and halogenated hydrocarbons {direct synthesis} · CPC title

• C08G77/60

  in which all the silicon atoms are connected by linkages other than oxygen atoms · CPC title

• C07F7/122 Primary

  by reactions involving the formation of Si-C linkages (hydrosilylation reactions C07F7/14; direct synthesis C07F7/16) · CPC title