Novel isocyanide compound and hydrosilylation reaction catalyst

Abstract

Provided are a novel isocyanide compound, a hydrosilylation reaction catalyst having excellent handling properties and storage properties that allows a hydrosilylation reaction to proceed under moderate conditions by using the isocyanide compound, and a method for producing an addition compound by a hydrosilylation reaction using the hydrosilylation reaction catalyst. A hydrosilylation reaction catalyst prepared from a catalyst precursor comprising a transition metal compound of groups 8, 9, or 10 of the periodic table, excluding platinum, such as an iron carboxylate, cobalt carboxylate, or nickel carboxylate, and a ligand comprising an isocyanide compound having an organosiloxane group.

Description

technical field [0001] The present invention relates to a novel isonitrile compound effective in obtaining a hydrosilylation catalyst and a hydrosilylation catalyst using the compound as a ligand. More specifically, it relates to a metal compound as a catalyst precursor and a ligand component. Catalysts for hydrosilylation reactions formed by novel isonitrile compounds. It also relates to a method for producing an addition compound using the catalyst using a hydrosilylation reaction. Background technique [0002] A hydrosilylation reaction in which an Si-H functional compound is added to a compound having a carbon-carbon double bond or a carbon-carbon triple bond is a useful means for synthesizing organosilicon compounds and is an industrially important synthesis reaction. [0003] Pt, Pd, and Rh compounds are known as catalysts for this hydrosilylation reaction, and among them, Pt compounds typified by Speier catalyst and Karstedt catalyst are the most used catalysts. [...

AI Technical Summary

Problems solved by technology

[0013] However, in the reaction using this complex, there are problems in that the reactivity to internal olefins is low, and Na amalgam, which is composed of water-restricted sodium and highly toxic mercury, needs to be handled carefully when synthesizing the complex. (or use water-repellent NaBEt 3 H), the stability of the coordination compound itself is low, and special equipment such as a glove box is required for handling. In addition, it must be stored under an inert gas nitrogen atmosphere and at low temperature

[0019] The reaction example of 1-hexene and triethoxysilane is also shown, but the amount of catalyst needs to be 2 mol%, and the catalytic activity is not high

[0020] In addition, as far as this catalyst is concerned, the stability of the coordination compound is low, and it is not easy to handle

[0021] Examples of iron, cobalt, and nickel catalysts in which the ligand is terpyridine, bisiminopyridine, or bisiminoquinoline have also been reported (Patent Documents 3 to 6), but the same as the above-mentioned Non-Patent Documents 6 to 8 , there are the following problems: the synthesis of the catalyst precursor, or the synthesis from the precursor to the complex catalyst is not easy in industry; the stability of the coordination compound itself is low; special equipment is required for disposal

However, in these patent documents, it is described that hydrosilylation was carried out in several combinations, but there is no description of the yield, etc., and it is unclear whether the reaction proceeds efficiently to a certain extent.

In addition, in all examples, ionic salts and hydride reducing agents were used as activators, however, almost all of the examples had no catalytic activity.

Images