Method for preparing halosilane compounds

Patent metadata

Field	Value
Publication number	US-11731992-B2
Application number	US-202217711376-A
Country	US
Kind code	B2
Filing date	Apr 1, 2022
Priority date	Apr 28, 2021
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

A halosilane compound: R1CH2CH2SiR52X is prepared by hydrosilylation reaction of a vinyl compound: R1CH═CH2 with a halogenodiorganosilane compound having formula: HSiR52X in the co-presence of an iridium catalyst, an internal olefin compound, and an allyl halide. The halosilane compound is prepared on an industrial scale with the advantages of low costs, high yields, and high selectivity, using a small amount of iridium catalyst.

First claim

The invention claimed is:

1. A method for preparing a halosilane compound comprising the step of effecting hydrosilylation reaction of a vinyl compound having the general formula (1):
R 1 CH═CH 2   (1)

wherein R 1 is a C 1 -C 20 substituted or unsubstituted monovalent hydrocarbon group which may contain oxygen or silicon, or a silyl group having the general formula (2):
—SiR 2 R 3 R 4   (2)

wherein R 2 to R 4 are each independently halogen, a C 1 -C 10 unsubstituted monovalent hydrocarbon group or a C 1 -C 10 unsubstituted alkoxy group, with a halogenodiorganosilane compound having the general formula (3):
HSiR 5 2 X  (3)

wherein R 5 is each independently a C 1 -C 20 unsubstituted monovalent hydrocarbon group and X is halogen, in the presence of an iridium catalyst to produce a halosilane compound having the general formula (4):
R 1 CH 2 CH 2 SiR 5 2 X  (4)

wherein R 1 , R 5 , and X are as defined above,
the hydrosilylation reaction being effected in the co-presence of an internal olefin compound having the general formula (5):

wherein R 6 and R 7 are each independently a C 1 -C 10 unsubstituted monovalent hydrocarbon group, R 6 and R 7 may bond together to form a ring with the carbon atoms to which they are attached, R 8 and R 9 are each independently hydrogen or a C 1 -C 10 unsubstituted monovalent hydrocarbon group and a halogenated allyl compound having the general formula (6):
YCH 2 CH═CH 2   (6)

wherein Y is halogen, exclusive of the vinyl compound having formula (1).

2. The method of claim 1 wherein the halogenated allyl compound is allyl chloride or allyl bromide.

3. The method of claim 1 wherein in the reaction system, the halogenated allyl compound is present in an amount of 0.00001 to 1 mole per mole of the vinyl compound.

4. The method of claim 1 wherein the iridium catalyst is an iridium complex having the general formula (7):
[Ir(R)Z] 2   (7)

wherein R is a cyclic diene compound having the general formula (8):

wherein R 10 and R 11 are each independently a C 1 -C 5 divalent hydrocarbon group, R 10 and R 11 may bond together to form a ring with the carbon atoms to which they are attached, and Z is halogen.

5. The method of claim 1 wherein the internal olefin compound is a cyclic olefin compound.

6. The method of claim 2 wherein in the reaction system, the halogenated allyl compound is present in an amount of 0.00001 to 1 mole per mole of the vinyl compound.

7. The method of claim 2 wherein the iridium catalyst is an iridium complex having the general formula (7):
[Ir(R)Z] 2   (7)

wherein R is a cyclic diene compound having the general formula (8):

wherein R 10 and R 11 are each independently a C 1 -C 5 divalent hydrocarbon group, R 10 and R 11 may bond together to form a ring with the carbon atoms to which they are attached, and Z is halogen.

8. The method of claim 3 wherein the iridium catalyst is an iridium complex having the general formula (7):
[Ir(R)Z] 2   (7)

wherein R is a cyclic diene compound having the general formula (8):

wherein R 10 and R 11 are each independently a C 1 -C 5 divalent hydrocarbon group, R 10 and R 11 may bond together to form a ring with the carbon atoms to which they are attached, and Z is halogen.

9. The method of claim 2 wherein the internal olefin compound is a cyclic olefin compound.

10. The method of claim 3 wherein the internal olefin compound is a cyclic olefin compound.

11. The method of claim 4 wherein the internal olefin compound is a cyclic olefin compound.

Assignees

• Shinetsu Chemical Co

Inventors

• Nakazawa Koichi
• Kojima Takahiro
• Kiyomori Ayumu

Classifications

• C07F15/0033

  Iridium compounds · CPC title

• C07F7/14 Primary

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

• B01J31/122

  Metal aryl or alkyl compounds · CPC title

• B01J2231/323

  Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation · CPC title

• B01J2531/827

  Iridium · CPC title