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Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation

An alkyl, unsaturated technology, used in catalytic reactions, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problems of reduced catalytic performance, aggregation or agglomeration, low activity, etc.

Active Publication Date: 2016-08-31
MOMENTIVE PERFORMANCE MATERIALS INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This makes such materials generally unsuitable for production or industrial-scale applications
[0009] Furthermore, many industrially important homogeneous metal catalysts suffer from the disadvantage that the catalytically active metal is lost to aggregation or agglomeration as the first charge of substrate is consumed, and its beneficial catalytic performance is greatly reduced by gel formation or precipitation
This is an expensive loss, especially for precious metals such as platinum
Heterogeneous catalysts are used to alleviate this problem, but have limited application to polymers and also have lower activity than their homogeneous counterparts

Method used

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  • Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation
  • Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation
  • Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0140] Embodiment 1: the synthesis of allyloxydiphenylsilane (alloxydiphenylsilane)

[0141]

[0142] The synthesis of allyloxydiphenylsilane follows a modified literature procedure described by Bergens, S.H.; Noheda, P.; Whelan, J.; Bosnich, B.J.Am.Chem.Soc. Implemented in the air. Allyl alcohol (2.9 g, 50 mmol) and triethylamine (5.1 g, 50 mmol) were dissolved in Et in an ice bath 2 The solution in O (250 mL) was cooled. The solution was treated dropwise with diphenylsilane chloride (11 g, 50 mmol) with rapid stirring. A large fluffy white precipitate was immediately observed (Et 3 NHCl). The mixture was warmed to room temperature and stirred for 1 h. The resulting solution was filtered through Celite and washed with Et 2 O washing. The filtrate was concentrated and resulted in a colorless oil which upon distillation (84-85°C, 65mmTorr) gave the desired product in 80% yield as a colorless oil. 1 H NMR (400MHz, benzene-d 6 )δ7.74–7.62(m,4H),7.27–7.06(m,6H),5.81(...

Embodiment 2

[0143] Embodiment 2: the synthesis of allyloxydimethylsilane (alloxydimethylsilane)

[0144]

[0145] Allyloxydimethylsilane was prepared in a similar manner to allyloxydiphenylsilane. Allyl alcohol (2.9 g, 50 mmol) and triethylamine (5.1 g, 50 mmol) were dissolved in Et in an ice bath 2 The solution in O (250 mL) was cooled. With rapid stirring, dimethylsilyl chloride (4.7 g, 50 mmol) was added dropwise to the solution. A large fluffy white precipitate was immediately observed (Et 3 NHCl). The mixture was warmed to room temperature and stirred for 1 h. The resulting solution was filtered through celite and washed with Et 2 O washing. The filtrate was concentrated and produced a colorless oil, which was then fractionally distilled (79-83 °C) to provide the product as a colorless oil in 50% yield. 1 H NMR (400MHz, chloroform-d) δ5.93 (ddt, J = 17.2, 10.1, 5.0Hz, 1H), 5.26 (dq, J = 17.2, 1.8Hz, 1H), 5.12 (dq, J = 10.4, 1.6 Hz, 1H), 4.68–4.55 (m, 1H), 4.18 (dt, J=5.0...

Embodiment 3

[0146] Embodiment 3: ( Mes PDI)Co(Ph 2 SiOC 3 H 5 )Synthesis

[0147]

[0148] In the glove box, place in 1mL Et 2 O in ( Mes PDI) a purple solution of CoMe (47mg, 0.1mmol) and Et of allyloxydiphenylsilane (24mg, 0.1mmol) 2 The O (1 mL) solution was mixed and stirred for 0.5 h. A maroon solution was observed. The solution was filtered through celite and concentrated under vacuum. The resulting solution was layered with pentane and stored at -35°C for 2 days and maroon crystals resulted. 1 H NMR (400MHz, benzene-d 6 )δ7.77(d,J=7.6Hz,1H),7.70(d,J=7.6,1H),7.31(t,J=7.6Hz,1H),7.10–6.94(m,8H),6.88–6.82 (m,2H),6.73–6.64(m,2H),6.62(s,1H),6.57(s,1H),5.24(dd,J=9.9,5.4Hz,1H),4.78(br,1H), 3.49(t, J=10.4Hz, 1H), 3.16(d, J=8.7Hz, 1H), 2.72(d, J=12.5Hz, 1H), 2.05(s, 3H), 2.01(s, 3H), 1.87(s,3H),1.76(s,3H),1.65(s,3H),1.44(s,3H),1.42(s,3H)1.02(s,3H). 13 C NMR (126MHz, benzene-d 6 )δ154.33,150.22,149.42,148.74,147.28,146.88,144.56,140.38,137.90,134.80,134.69,13...

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Abstract

Disclosed herein are cobalt complexes containing pyridine di-imine ligands and chelating alkenyl-modified silyl ligands, and their use as hydrosilylation and / or dehydrogenative silylation and crosslinking catalysts. The cobalt complexes also exhibit adequate air stability for handling and manipulation.

Description

[0001] Cross References to Related Applications [0002] This application claims priority and benefit to U.S. Provisional Application No. 61 / 906,210, filed November 19, 2013, entitled "Cobalt Catalysts and Their Use for Hydrosilylation and Dehydrogenative Silylation," the entire contents of which are hereby incorporated by reference in their entirety into this article. technical field [0003] The present invention relates generally to transition metal-containing compounds, and more particularly to cobalt complexes containing pyridinediimine ligands, and their use as catalysts for hydrosilylation and dehydrosilylation reactions. Background technique [0004] Hydrosilylation chemistry, generally involving the reaction between silyl hydrides and unsaturated organic groups, is the basis for the preparation of commercial silicone-based products such as silicone surfactants, silicone fluids and silanes as well as many Basis for synthetic routes to additional curing products such...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/06C07F7/08C07F7/18
CPCC07F15/065C07F7/0879C07F7/1876C07F7/0838C07F7/1804B01J31/2295C07F15/06C08G81/02B01J2531/845B01J2231/766B01J2231/323B01J2231/14
Inventor 刁天宁保罗·J·奇里克阿罗波·库马尔·罗伊肯里克·路易斯苏珊·奈基思·J·韦勒约翰尼斯·G·P·代利斯虞任远
Owner MOMENTIVE PERFORMANCE MATERIALS INC
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