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Platinum catalyzed hydrosilylation reactions utilizing cyclodiene additives

A technology of hydrosilylation and cyclodiene, which is applied in the fields of compounds, organic chemistry, chemical instruments and methods of elements of group 4/14 of the periodic table, and can solve the problem of no COD-Pt substances, etc.

Inactive Publication Date: 2017-04-19
MOMENTIVE PERFORMANCE MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, as reported in a JACS publication, the use of only one COD per Pt resulted in no identifiable COD-Pt species

Method used

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  • Platinum catalyzed hydrosilylation reactions utilizing cyclodiene additives
  • Platinum catalyzed hydrosilylation reactions utilizing cyclodiene additives
  • Platinum catalyzed hydrosilylation reactions utilizing cyclodiene additives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Example 1: Allyl Methacrylate (AMA) and SiMeCl 2 H Hydrosilylation using diene additives

[0086] A 4-neck round bottom flask was fitted with an addition funnel, syringe port, alcohol thermometer, magnetic stir bar, and straight water condenser topped with a dry ice condenser. Addition funnel with N 2 inlet and before reacting the N 2 The tubing is separate from the t-piece that connects to the bubbler. The system uses N 2 Rinse and load with appropriate inhibitor. SiMeCl 2 H (16.5 g, 0.140 mol) was charged to the addition funnel. A solution of allyl methacrylate (19.7 g, 0.16 mol), chloroplatinic acid (2 ppm Pt) and cyclooctadiene (COD) in ethanol (0.39 μ mol, equimolar with Pt) was charged in the round bottom flask, Among them, COD is used as an additive. The reaction mixture was heated to 80 °C. Approximately 1 mL of chlorosilane was added and the reaction was monitored for exotherm. Once an exothermic reaction was detected, the chlorosilane was added slowl...

Embodiment 2

[0089] Example 2: Allyl Methacrylate with SiMeCl 2 H Hydrosilylation using a diene additive to evaluate the color of the reaction product

[0090] Reactions were performed similar to those discussed above with a 5 ppm Pt loading, except that no color-imparting inhibitor was added to the reaction. For allyl methacrylate and SiMeCl performed with different amounts of COD equivalents 2 The reaction of H evaluates the color of the product.

[0091] Table 1.

[0092] COD equivalent Color (Pt / Co) 0 331 0 193 0.5 150 1 46

Embodiment 3

[0093] Embodiment 3: Allyl methacrylate and Si(OEt) 3 H hydrosilylation with diene additive

[0094] A 4-neck round bottom flask was equipped with a magnetic stir bar, a direct condenser with a dry ice condenser on top, a syringe port, a liquid addition funnel, and a thermometer and was placed under N 2 Down. A reaction vessel was charged with inhibitor and allyl methacrylate (15 mL, 0.11 mol), chloroplatinic acid solution (2 ppm Pt) COD solution (equimolar to Pt). The addition funnel was charged with triethoxysilane (19 mL, 0.1 mol). The reaction was heated to 90°C, then an aliquot of triethoxysilane (3-5 vol%) was added and the reaction was monitored for exotherm. After confirmation of the exotherm, the remaining triethoxysilane was added via the addition funnel at a rate to maintain the reaction at 85°C-95°C. After the final addition of triethoxysilane, the reaction was heated at 90°C for 90 minutes. by GC and 1 The resulting product was analyzed by H NMR. The averag...

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Abstract

A process for the hydrosilylation of an unsaturated compound comprising reacting (a) a silyl hydride with (b) an unsaturated compound in the presence of (c) a platinum compound and (d) a cyclodiene, with the provisos that (i) when the unsaturated compound is a terminal alkyne, the silyl hydride is other than a halosilane, and (ii) when the platinum compound is a Pt(II)-based compound, the ratio of total moles of cyclodiene to moles of platinum is less than 3:1.

Description

[0001] Cross References to Related Applications [0002] This patent application claims priority and benefit to U.S. Provisional Application No. 62 / 011,825, entitled "Platinum-Catalyzed Hydrosilylation Reactions Using Cyclodiene Additives," filed June 13, 2014, which is incorporated by reference in its entirety. into this article. technical field [0003] The present invention generally relates to the use of cyclodiene additives to improve catalyst performance in platinum-catalyzed hydrosilylation reactions. Background technique [0004] Hydrosilylation chemistry, involving the reaction between silylhydrides and unsaturated organic groups, is the basis for synthetic routes to produce commercial silicone products such as silicone surfactants, silicone fluids, and organosilanes. Conventionally, hydrosilylation reactions have been catalyzed by noble metal catalysts such as platinum or rhodium metal complexes. [0005] Various noble metal complex catalysts are known in the art...

Claims

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Application Information

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IPC IPC(8): C07F7/14C07F7/18
CPCC07F7/14C07F7/1876C07F7/12C07F7/1804C07F7/0829C07F7/0879
Inventor 阿罗波·罗伊朱莉·波伊尔于尔根·科勒大卫·詹金斯安德里亚·特罗托肯里克·路易斯
Owner MOMENTIVE PERFORMANCE MATERIALS INC
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