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Sulphur-poisoning-resistant hydrosilylation platinum catalyst, preparation method and application

A platinum catalyst and hydrosilylation technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc., can solve the problem of whether anti-poisoning agents and catalysts can be evenly contacted and other problems, to achieve the effect of strong anti-sulfur poisoning performance and high-efficiency catalytic activity

Active Publication Date: 2013-04-24
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the need to add an additional anti-poisoning agent when chloroplatinic acid catalyzes the hydrosilylation reaction, there are problems such as whether the anti-poisoning agent and the catalyst can be evenly contacted, so it is necessary to improve the existing catalyst

Method used

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  • Sulphur-poisoning-resistant hydrosilylation platinum catalyst, preparation method and application

Examples

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preparation example Construction

[0024] Preparation of platinum complexes (platinum catalysts):

[0025] CH≡CSi(R) 3 (R is -CH 3 , -CH 2 CH 3 , -Ph or -CH(CH 3 ) 2 ) and cis-bis(triphenylphosphine)platinum dichloride were mixed, and at the same time CuI was added to react at 80 °C until fully reacted, the solvent was spin-dried, and recrystallized with hexane / benzene as the solvent to obtain a platinum complex, whose structural formula is as follows:

[0026] , where R is -CH 3 , -CH 2 CH 3 , -Ph or -CH(CH 3 ) 2 .

[0027] The reaction process of the hydrosilylation reaction : Add the platinum complex into the three-necked flask, under the protection of nitrogen, add olefin and triethoxyhydrogensilane dropwise through the dropping funnel, slowly raise the temperature to 90°C to maintain the reaction temperature, turn on the condensing reflux, continue to stir the reaction until fully, static Set, cooled to room temperature, vacuum distillation to collect the corresponding fractions, and cond...

Embodiment 1

[0030] Catalyst preparation: In a three-necked flask equipped with a thermometer, dropping funnel, mechanical stirrer, reflux condenser, and protected by argon, diethylamine was used as the reaction solvent, and CH≡CSi(CH 3 ) 3 (2.2 mmol) and cis-bis(triphenylphosphine)platinum dichloride (1 mmol); at the same time, CuI (5 mg) was added to react at 80 ℃ for 6 h, the solvent was spin-dried, and recrystallized with hexane / benzene as solvent to obtain Platinum complexes (PPh 3 ) 2 Pt[-C≡CSi(CH 3 ) 3 ] 2 , the yield is 92%.

[0031]The reaction process of the hydrosilylation reaction: in a 250 ml three-necked flask, add the platinum catalyst (0.625 mmol) prepared above, under the protection of nitrogen, add styrene (1.25 mol) and triethoxy hydrogen successively dropwise through the dropping funnel Silane (1.5mol), slowly heat up to 90°C, keep the reaction temperature, open the condensing reflux, continue to stir the reaction for 5 hours, let stand, cool to room temperature, ...

Embodiment 2

[0033] Catalyst preparation: with embodiment 1,

[0034] Test the reaction process of anti-sulfur poisoning performance: in the there-necked flask of 250 milliliters, add the above-mentioned prepared platinum catalyst (0.625mmol), under the protection of nitrogen, drop the styrene containing sulfur poisoning agent thiazole (1.25mmol) successively through the dropping funnel (1.25mol) and triethoxyhydrogensilane (1.5mol), slowly warming up to 90°C, maintaining the reaction temperature, turning on condensing reflux, continuing to stir for 5 hours, standing still, cooling to room temperature, and determining styrene by GC-MS The conversion rate was 85.4%, and the β-adduct 1-triethoxysilyl-2-phenylethane (PhCH 2 CH 2 Si(OCH 2 CH 3 ) 3 ) yield was 91.3%, and the α-adduct 1-triethoxysilyl-1-phenylethane (PhCH(CH 3 )Si(OCH 2 CH 3 ) 3 ) yield was 5.8%.

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Abstract

The invention belongs to the field of organic catalytic chemistry and relates to a hydrosilylation platinum catalyst having the characteristic of sulphur-poisoning resistance, and a preparation method and application of the hydrosilylation platinum catalyst. The sulphur-poisoning-resistant hydrosilylation platinum catalyst is characterized by comprising the following structural general formula, wherein R is -CH3, -CH2CH3, -Ph or -CH(CH3)2. Platinum alkyne coordination compounds which are provided by the invention serve as a catalyst for hydrosilylation reaction, the platinum alkyne coordination compounds can promote the silicon hydrogen reaction of olefin and hydrogen-containing silane, and the platinum alkyne coordination compounds have great sulphur-poisoning resistant performance. In the application of the sulphur-poisoning-resistant hydrosilylation platinum catalyst to the hydrosilylation reaction of the olefin and the hydrogen-containing silane, a hydrosilylation product is obtained by using the olefin and the hydrogen-containing silane of a sulphur-containing poisoning agent as raw materials, using the platinum alkyne coordination compounds (the sulphur-poisoning-resistant hydrosilylation platinum catalyst) which are provided by the invention as the catalyst, heating and stirring for full reaction, carrying out reduced pressure distillation, and collecting fractions.

Description

technical field [0001] The invention belongs to the field of organic catalytic chemistry and relates to a platinum catalyst for hydrosilylation, in particular to a platinum hydrosilylation catalyst with anti-sulfur poisoning properties, as well as its preparation method and application. Background technique [0002] As we all know, the hydrosilylation reaction refers to the addition reaction of Si-H and unsaturated double bonds or triple bonds to generate silicon-containing organic compounds or polymers. It is one of the most studied reactions in organosilicon chemistry. It occupies an important position in the chemical and silicone industries. Compared with the conventional catalytic hydrogenation reaction, the conditions of the hydrosilylation reaction are mild, no high-pressure technology is required, and the operability is strong. Since 1957 Speier et al. (Speier, J. L.; Webster, J. A.; Barnes, G. H. J. Am. Chem. Soc. 1957, 79 , 574.) found chloroplatinic acid (H 2 P...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07F7/18
Inventor 来国桥厉嘉云彭家建白赢吕素芳
Owner HANGZHOU NORMAL UNIVERSITY
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