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Novel isocyanide compound and hydrosilylation reaction catalyst

一种氢化硅烷化、化合物的技术,应用在有机化合物/氢化物/配位配合物催化剂、物理/化学过程催化剂、催化反应等方向,能够解决反应性低、不清楚、处置不容易等问题,达到溶解性好的效果

Active Publication Date: 2018-08-31
SHIN ETSU CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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.

Method used

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  • Novel isocyanide compound and hydrosilylation reaction catalyst
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  • Novel isocyanide compound and hydrosilylation reaction catalyst

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Embodiment

[0303] Hereinafter, synthesis examples, examples, and comparative examples are given to describe the present invention in more detail, but the present invention is not limited by the following examples.

[0304] All the solvents used in the preparation of the metal compound were deoxidized and dehydrated by known methods.

[0305] The obtained metal compound was stored at 25°C under a nitrogen atmosphere and used in the reaction.

[0306] The hydrosilylation reaction and solvent purification of olefins were all carried out under an inert gas atmosphere, and solvents used in various reactions were all purified, dried, and deoxygenated by known methods in advance.

[0307] 1 H. 13 C. 19 The F-NMR measurement was performed using JNM-ECA600 and JNM-LA400 manufactured by JEOL Ltd., and the IR measurement was performed using FT / IR-550 manufactured by JASCO Corporation.

[0308] In addition, in the chemical structural formula shown below, hydrogen atoms are omitted according to c...

Synthetic example 1

[0309] [Synthesis example 1] Synthesis of iron pivalate

[0310] The reference J.Cluster.Sci., 2005, 16, 331. was synthesized by the following method.

[0311] 0.86 g (15.4 mmol) of reduced iron and 3.50 g (34.3 mmol) of pivalic acid were added to a 50 mL two-necked eggplant-shaped flask equipped with a reflux tube, and stirred at 160° C. for 12 hours. At this time, the reaction solution changed from colorless and transparent to green. Furthermore, 2.50 g (24.5 mmol) of pivalic acid was added, and it stirred at 160 degreeC for 19 hours. Then, the reaction solution was filtered, combined with the recovered supernatant, and dried at 80°C under reduced pressure. The obtained solid was washed with hexane to obtain a green solid (2.66 g, yield 67%).

[0312] FT-IR (KBr) ν: 2963, 2930, 2868, 1583, 1523, 1485, 1457, 1427, 1379, 1362, 1229, 1031, 938, 900, 790, 608, 576, 457cm -1

Synthetic example 2

[0313] [Synthesis example 2] Synthesis of cobalt pivalate

[0314] With reference to the document Russ.Chem.Bull., 1999, 48, 1751., it was synthesized by the following method.

[0315] Add 1.15 g (6.5 mmol) of cobalt acetate, 1.55 g (15.2 mmol) of pivalic acid, and 0.5 mL (2.5 mmol) of pivalic anhydride into a 50 mL two-necked eggplant-shaped flask with a reflux tube, and stir at 160 ° C. for 1 hour. At this time, the reaction solution changed from light purple to purple. Then, it was dried under reduced pressure at 80° C., and the obtained solid was washed with pentane and diethyl ether, and dried to obtain a purple solid (1.15 g, yield 68%).

[0316] FT-IR (KBr) ν: 2963, 2929, 2868, 1599, 1524, 1485, 1457, 1420, 1379, 1363, 1229, 1032, 938, 900, 792, 613, 585, 460cm -1

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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. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10B01J31/22C07B61/00
CPCC07B61/00C07F7/10B01J31/0252B01J2231/323B01J2531/821B01J2531/824B01J2531/842B01J2531/845B01J2531/847B01J31/12C07F7/0879C07F7/1876B01J2531/82C07F7/0805C07F7/0838C07F7/21C08G77/38C08G77/08C07F7/081
Inventor 作田晃司永岛英夫砂田祐辅野田大辅
Owner SHIN ETSU CHEM CO LTD
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