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Preparation of bis(N,N-diethyl) aminomethyl phenyl silane

A technology of diethylaminomethylphenylchlorosilane and aminomethylphenylsilane, which is applied in the field of organic silicon preparation and can solve the problems of inability to obtain high-purity methylphenyldichlorosilane and difficulty in separation and purification , to achieve the effect of convenient process, easy access to raw materials and simple operation

Inactive Publication Date: 2008-12-24
HANGZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0008] As we all know, due to the conjugation effect of the benzene ring, there are significant differences in the electron cloud density and distribution between the methylphenylsilyl group and the dimethylsilyl group, resulting in the There are big differences in the physical and chemical properties of chlorosilanes. For example, dimethyldichlorosilane has a low boiling point (atmospheric pressure boiling point 70.5°C), and is easy to purify. The purity of industrial grade dimethyldichlorosilane can reach more than 99.995wt%, while methylbenzene Phenyldichlorosilane has a high boiling point (atmospheric pressure boiling point 205.5°C), currently all methylphenyldichlorosilane prepared by various production processes inevitably contains phenyltrichlorosilane, and its atmospheric pressure boiling point is 201°C, due to The boiling points of methylphenyldichlorosilane and phenyltrichlorosilane are very high and very close, which makes it impossible to obtain high-purity methylphenyldichlorosilane
Therefore, compared with the preparation of bis(N,N-diethyl)amine dimethyl silane, the synthesis of bis(N,N-diethyl)aminomethylphenylsilane and the bis(N,N-diethyl) The separation and purification of aminomethylphenylsilane is more difficult

Method used

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  • Preparation of bis(N,N-diethyl) aminomethyl phenyl silane
  • Preparation of bis(N,N-diethyl) aminomethyl phenyl silane
  • Preparation of bis(N,N-diethyl) aminomethyl phenyl silane

Examples

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Embodiment 1～9

[0028]Under the protection of nitrogen, add 150mL of dichloromethane and a certain amount of diethylamine that were treated with calcium hydride drying and reflux into a 500mL four-port container equipped with an electric stirrer, a constant pressure dropping funnel and an air port device after drying. In the round-bottomed flask, when the temperature of the reaction system reaches -20°C, slowly add 19.1 g (0.1 mol) of methylphenyldichlorosilane with a purity of 97wt% dropwise for 2 hours. After the dropwise addition, the temperature was maintained for 2h, and then the reaction was stopped. The reaction mixture was transferred to a rotary evaporator, and 80 mL of dichloromethane was recovered, then the concentrated reaction mixture was lowered to room temperature, airtight, protected from light and allowed to stand for 24 hours, and then filtered by centrifugal filtration to remove ammonium salts, and the filtrate was GC -MS to analyze and calculate the yield of bis(N,N-diethy...

Embodiment 10

[0033] After mixing the 233g filtrate obtained in Examples 1 to 9, add it to a 500mL three-necked flask, distill under reduced pressure, collect 199.4°C / 2.0Kpa cuts, and obtain 156g of a light yellow solution, which consists of 67.92wt% (N,N-di Ethyl) aminomethylphenyl chlorosilane, 22.12wt% of two (N, N-diethyl) aminomethylphenylsilane, 6.24wt% unreacted methylphenyldichlorosilane, 0.96wt % of bis(N,N-diethyl)aminophenylchlorosilane and 2.75 wt% of methylphenylcyclotrisiloxane.

[0034] Add 53.3g (0.73mol) of diethylamine that adopts the method described in Example 1 to dry handle in a 500mL four-neck round bottom flask equipped with an electric stirrer, a constant pressure dropping funnel, and an air inlet device, and then add 100mL of the dried dichloromethane solution, when the temperature of the reaction mixture reaches -15°C, slowly add 100g of the fractions collected by the above vacuum distillation into the reaction flask under stirring, and the dropwise addition time ...

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Abstract

The invention discloses a method for preparing organosilicon, in particular a method for preparing bi-(N, N-diethyl) amine methyl phenyl silicane. The method comprises the following steps that: dried methylene dichloride and di-ethylamine are reacted with methyl phenyl dichlorosilane under nitrogen protection, and partial solvent is recovered after evaporation under normal pressure; after protecting from light and standing, ammonium salt is removed from the partial solvent; after vacuum distillation recovery, filtrate is reacted with the di-ethylamine at a low temperature, and all dichloromethane solvent is recovered after evaporation under normal pressure; ammonium salt is removed by filtration; and then the colorless transparent bi-(N, N-diethyl) amine methyl phenyl silicane is prepared after vacuum rectification. The method has the advantages that: the technological process is simple; the operation is convenient; the industrialization is easy; the purity of the target product bi-(N, N-diethyl) amine methyl phenyl silicane obtained is high; and the method is particularly suitable for synthesizing series diamino compounds, namely (bi-n-amino phenoxyl) methyl phenyl silicane (n is equal to 2, 3 or 4).

Description

technical field [0001] The invention relates to a method for preparing organosilicon, in particular to a method for preparing an intermediate bis(N,N-diethyl)aminomethylphenylsilane for preparing a diamine monomer compound for silicon-containing polyimide. technical background [0002] Bis(N,N-diethyl)aminomethylphenylsilane is an important intermediate for the synthesis of siloxane-containing diamino compound (bis-4-aminophenoxy)methylphenylsilane, and its structural formula is: [0003] [0004] Bis(N,N-diethyl)aminomethylphenylsilane reacts with p-aminophenol or p-nitrophenol compound to obtain diamino compound bis-(4-aminophenoxy)methylphenylsilane Or dinitro compound bis-(4-nitrophenoxy)methylphenylsilane, bis(4-nitrophenoxy)methylphenylsilane finally generates bis-(4 -aminophenoxy)methylphenylsilane. Bis(N,N-diethyl)aminomethylphenylsilane reacts with m-aminophenol or m-nitrophenol compound to obtain diamino compound bis(3-aminophenoxy)methylphenylsilane or Dinit...

Claims

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Application Information

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IPC IPC(8): C07F7/10
Inventor 伍川胡从达蒋剑雄董红杨雄发
Owner HANGZHOU NORMAL UNIVERSITY
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