JP2634441B2 - Method for producing alkenylsilane - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a method for producing alkenylsilane. Specifically, using a specific hydrogenating agent, a silyl group represented by the general formula SiR _n Cl _3-n (where R is an alkyl group or a phenyl group, n Is 0
Alkenylsilane represented by SiR _n R'H _3-n for hydrogenating alkenyl chlorosilane represented by the formula (2), wherein R is an alkyl group or a phenyl group, R 'is a vinyl group or The present invention relates to a method for producing an allyl group or a butenyl group, wherein n is 0 to 2).

(Prior art)

A method for producing alkenylsilane by hydrogenating alkenylchlorosilane is well known, and a method using lithium aluminum hydride or alkylaluminum hydride as a hydrogenating agent is well known (JWCurr
Y et al., J. Am. Chem. Soc., VOL 78, 1686-9 (1956), JP-A-58
−9809).

[Problems to be Solved by the Invention] The former method has a problem that the yield is poor in addition to the use of ether as the reaction solvent, and the latter method has a problem in terms of yield.
%, But there is a problem that the hydrogen source is special.

[Means for solving the problem]

The present inventors have earnestly studied a method for solving the above-mentioned problem and completed the present invention.

That is, in the present invention, a silyl group represented by the general formula SiR _n Cl _3-n (where R is an alkyl group or a phenyl group and n is 0 to 2) is used as an unsaturated group selected from vinyl, allyl, and butenyl. Is hydrogenated from an alkenylchlorosilane represented by a bond, and the corresponding alkenylsilane represented by SiR _n R'H _3-n (where R is an alkyl group or a phenyl group, R 'is a vinyl group or an allyl A method for producing an alkenyl silane, comprising using a sodium aluminum hydride glycol as a hydrogenating agent in the method for producing a alkenylsilane or a butenyl group, wherein n is 0 to 2).

In the present invention, alkenyl chlorosilanes represented by the general formula Si include unsaturated groups selected from vinyl, allyl and butenyl.
A silyl group represented by R _n Cl _3-n
As an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, or a phenyl group,
n is 0 to 2; Specific examples include trichlorovinylsilane, trichloroallylsilane, trichlorobutenylsilane, methyldichlorovinylsilane, methyldichloroallylsilane, dimethylchlorovinylsilane, and dimethylchloroallylsilane.

The sodium aluminum hydride alkyl glycols important in the present invention are those obtained by substituting 1 to 3 hydrogen atoms of sodium aluminum hydride with an alkyl glycol. Specific examples of the alkyl glycol group include a methoxyethyloxy group, Monoethers of ethylene glycol such as an ethoxyethyloxy group and a propoxyethyloxy group are preferably exemplified, and monoethers of diethylene glycol and triethylene glycol are also exemplified.

In the present invention, the reaction is usually carried out in the presence of a solvent, but it is not necessary to use ethers as the solvent, and a hydrocarbon compound, particularly an aromatic hydrocarbon compound, is sufficient.
Benzene, toluene, xylene, ethylbenzene, propylbenzene and the like are preferably used.

In the present invention, since the reaction takes place extremely easily, it is not necessary to particularly heat and normal temperature is sufficient. However, removal of the heat of reaction or alkenylsilane represented by hydrogenated SiR _n R′H _3-n (formula Wherein R is an alkyl or phenyl group;
′ Is a vinyl group, an allyl group, or a butenyl group, and n is 0 to
In order to recover 2), it is preferable to remove the heat of reaction or control the mixing speed of the two so that the temperature becomes an appropriate temperature equal to or higher than the boiling point of the alkenylsilane. The reaction pressure is not particularly limited, but it is preferable to carry out the reaction at normal pressure to slightly elevated pressure because the apparatus is simple.

〔Example〕

 Hereinafter, the present invention will be further described with reference to Examples.

Was synthesized dimethylvinylsilane dimethyl chloro vinyl silane with a compound represented by Example -1 Formula NaAlH ₂ as sodium hydride aluminum alkyl glycol _{(CH 3 O-C 2 H} 4 O-) 2. Using cumene as a reaction solvent, NaAlH ₂ (CH ₃ O-
402 g of C ₂ H ₄ O-) ₂ and dimethylchlorovinylsilane 2
00 g was added dropwise while controlling the dropping rate so that the temperature became 80 ° C., and the dimethylvinylsilane obtained at the same time was collected in a trap cooled at 0 ° C. The yield based on dimethylchlorosilane was 88%.

Comparative Example 1 The procedure of Example 1 was repeated except that 500 g of dibutyl ether was used as a solvent and 19 g of lithium aluminum hydride was used as a hydrogenating agent. However, since the temperature could not be controlled at the dropping speed, the flask was heated first to 65 ° C. to start the reaction. 64% yield based on dimethylchlorosilane
Met.

Example 2 Instead of dimethylchlorovinylsilane, 117 g of methyldichlorovinylsilane was used, the reaction temperature was 70 ° C., and collection was performed at dry ice-methanol temperature. The yield is
It was 92%.

〔The invention's effect〕

By performing the method of the present invention, an unsaturated group selected from vinyl, allyl, and butenyl is converted to a general formula SiR _n Cl _3-n
Wherein R is an alkyl group or a phenyl group, and n is 0 to 2, and a corresponding silyl group is represented by a corresponding SiR _n R′H _3-n. Alkenylsilane (where R is an alkyl group or a phenyl group,
R 'is a vinyl group, an allyl group, or a butenyl group;
2) can be produced in good yield and is industrially valuable.

Claims (1)

(57) [Claims] 1. An unsaturated group selected from vinyl, allyl and butenyl is substituted by a silyl group represented by the general formula SiR _n Cl _3-n (wherein
R is an alkyl group or a phenyl group, and n is an alkenyl silane represented by SiR _n R′H _3-n by hydrogenating an alkenyl chlorosilane represented by a form in which 0 to 2 is bonded. Is an alkyl group or a phenyl group, R 'is a vinyl group, an allyl group or a butenyl group, and n is 0 to 2), characterized in that sodium aluminum hydride alkyl glycols are used as a hydrogenating agent. A method for producing the alkenylsilane.