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Hydrosilylation of alkenes catalyzed by rhodium complexes in a room temperature ionic liquid/supercritical CO2 medium

A technology of room temperature ionic liquid and hydrosilylation reaction, applied in organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, compounds of group 4/14 elements of the periodic table, etc., can solve many problems Difficult to separate, recycle and reuse, difficult to apply to industrialization, and low catalytic activity to achieve the effects of inhibiting the formation of by-product alkanes, high selectivity, and simple separation operations

Inactive Publication Date: 2011-12-28
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But for some types of hydrosilylation reactions, such as the hydrosilylation of olefins and alkoxysilanes, transition metals (Rh, Ru, etc.) are used as catalysts, and the catalytic activity is not high (Bogdan Marciniec, and Jacek , J. Organomet. Chem., 1983, 253, 349-362)
At the same time, the catalytic system is also difficult to separate, recover and reuse from the reaction system.
Since then, Chen Yuanyin et al. (Meng Lingzhi, Ke Aiqing, Chen Yuanyin, Applied Chemistry, 1997, 14, 1, 107-109; Liu Ying, Chen Yuanyin, Sheng Rongsheng, Molecular Catalysis, 1997, 11, 5, 394-400; Dai Yanfeng, Xiao Bin, Li Fengyi, Ru Xiang, Chemical Reagents, 2005, 27, 12, 707-709) studied the application of Pt on polymer compounds for hydrosilylation reaction, but the preparation of the catalyst is complicated and the reaction activity is not high , it is difficult to apply to industrialization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 250ml reactor, add Rh(PPh 3 ) 3 Cl(1.25mmol), KO t Bu (1.25mmol), 1-butyl-3-methylimidazolium hexafluorophosphate (BMImPF 6 ) (25ml), styrene (2.5mol) and triethoxyhydrosilane (2.75mol), slowly warming up to 70 ° C, into CO 2 (80atm), stirred and reacted for 5 hours, the product was collected under reduced pressure, and the conversion rate of styrene was measured by GC-MS to be 91.3%, and the β adduct 1-triethoxysilyl-2-phenylethane (PhCH 2 CH 2 Si(OCH 2 CH 3 ) 3 ) yield was 85.8%, and the α-adduct 1-triethoxysilyl-1-phenylethane (PhCH(CH 3 )Si(OCH 2 CH 3 ) 3 ) The yield is 14.2%. The liquid in the kettle was washed with ether and recovered for reuse.

Embodiment 2

[0024] In embodiment 1, add triphenylphosphine rhodium chloride (2.5mmol), the conversion rate of styrene is 100% after the reaction finishes, and β adduct 1-triethoxysilyl-2-phenylethane ( PhCH 2 CH 2 Si(OCH 2 CH 3 ) 3 ) yield was 84.5%, and the α-adduct 1-triethoxysilyl-1-phenylethane (PhCH(CH 3 )Si(OCH 2 CH 3 ) 3 ) The yield is 15.5%.

Embodiment 3

[0026] In embodiment 1, add triphenylphosphine rhodium chloride (0.5mmol), the conversion ratio of styrene after the reaction finishes is 54.3%, β adduct 1-triethoxysilyl-2-phenylethane ( PhCH 2 CH 2 Si(OCH 2 CH 3 ) 3 ) yield was 86.3%, and the α-adduct 1-triethoxysilyl-1-phenylethane (PhCH(CH 3 )Si(OCH 2 CH 3 ) 3 ) The yield is 13.7%.

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Abstract

The invention relates to a hydrosilylation of rhodium complex catalyzed alkene in room-temperature ion liquid / super-critical CO2 medium. The technical problem to be solved is characterized in that thehydrosilylation condition is moderate and safe, the reaction conversion rate is high, the outcome Beta-addition product of the hydrosilylation has strong selection, no outgrowth paraffin hydrocarbonis produced, the outcome and the catalyst are convenient to be separated from each other, and the catalyst can be reclaimed and re-utilized. The hydrosilylation is characterized in that the alkene andhydrogen-contained silanes are taken as raw materials, rhodium compound is taken as the catalyst, the potassium tert-butoxide is taken as adjuvant, and the room-temperature ion liquid / supercritical CO2 is taken as reaction medium; and the mixture is heated and mixed so as to react sufficiently, the outcome is collected by reducing pressure, thus obtaining the hydrosilylation products.

Description

technical field [0001] The invention relates to the field of organic chemistry, specifically a room temperature ionic liquid / supercritical CO 2 (IL / scCO 2 The rhodium complex in the ) medium catalyzes the hydrosilylation reaction of alkenes. Background technique [0002] The hydrosilylation reaction catalyzed by unsaturated olefins is one of the most important ways to synthesize organosilicon coupling agents and functional organosilicon compounds and polymers, and plays an important role in organosilicon chemistry and organosilicon industry (Leslie D. Field , Antony J. Ward, J. Organomet. Chem, 2003, 681, 91-97). Karstedt catalyst is the most widely used catalyst in industrial hydrosilylation reaction. But now the common platinum catalyst for hydrosilylation reaction has the disadvantages of low reaction conversion rate and selectivity, and it is easy to generate platinum black during the same reaction (Chisso Corp. JP, 8204995, 1982). Later, through the study of various...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C07F7/14C07F7/08B01J31/24B01J31/22
CPCY02P20/54
Inventor 厉嘉云来国桥彭家建白赢胡应乾
Owner HANGZHOU NORMAL UNIVERSITY