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Preparation of secondary aminoisobutyl alkoxysilanes

A technology for secondary aminoisobutylalkoxysilane and hydrogenated alkoxysilane, applied in the field of preparing secondary aminoisobutylalkoxysilane, can solve the problem of low equipment yield, high level of waste or excess raw materials, and difficulty in disposal Solid hydrochloride and other problems, to achieve the effect of high yield and conversion rate

Inactive Publication Date: 2003-07-02
GENERAL ELECTRIC CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These pathways suffer from low yields per unit volume of equipment used, high levels of waste or excess raw material and generation of large quantities of solid hydrochloride that are difficult to dispose of

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1- Hydrosilation of N-ethylmethallylamine and trimethoxysilane

[0033] Install a magnetic stir bar, standard heating mantle, thermocouple, addition funnel, condenser and N to a one-liter three-necked round bottom flask 2 Inlet / bubbler. Put 220g (1.80mol) of trimethoxysilane into the flask, heat it to 60℃, and add 0.25ml of tris(divinyltetramethyldisiloxane) diplatinum (O) (containing 5% Pt / Toluene-referred to as Pt catalyst in these examples). The solution was further heated to 68°C, and then 150 g (1.52 mol) of N-ethylmethallylamine was added dropwise over 45 minutes. After the addition, the contents were heated to 90°C and kept at this temperature for 1 hr. Then the temperature was increased to 105°C and held for 4.5 hr. Once the reaction is complete, the mixture is cooled to room temperature, 16 g (0.5 mol) of methanol is added, heated slightly, and then distilled. Finally, it was purified by vacuum distillation to obtain 273 g (1.24 mol) of N-ethyl-3-trimetho...

Embodiment 2

[0034] Example 2 Hydrosilation of N-ethylmethallylamine and methyldiethoxysilane

[0035] The equipment is similar to Example 1 except that the distillation head replaces the condenser. 381 g (2.84 mol) of methyl diethoxysilane and 0.65 ml of platinum catalyst were charged into the flask. The contents were heated to 90°C, and 260 g (2.63 mol) of N-ethylmethallylamine was added via the addition funnel over 30 minutes. Immediately after the addition was completed, the contents were heated to 110°C for one hr. The product was separated by vacuum distillation to obtain 485 g (2.08 mol) of N-ethyl-(3-diethoxymethylsilyl)-2-methylpropylamine. The product (b.p. 88-90°C, 27 mmHg) was identified by GC / MS. The isolated yield was 79%.

Embodiment 3

[0036] Example 3- Hydrosilation of N-ethylmethallylamine and trimethoxysilane

[0037] 16.8kg (167mol) N-ethylmethallylamine and 42ml platinum catalyst were added into a 50L jacketed glass reactor equipped with overhead columns. The contents were then heated to 93°C, and 24.9 kg (204 mol) of trimethoxysilane was slowly added over 4 hours. After the addition was complete, the reaction mixture was heated to 105°C for 2 hr. After the heating stage, the contents were cooled to below 50°C, and 1.5 L of methanol was added. The crude material was distilled to obtain 28.9 kg (131 mol) of material with a purity of 99%. The yield of isolated N-ethyl-3-trimethoxysilyl-2-methylpropylamine was 78% based on N-ethylmethallylamine.

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PUM

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Abstract

A highly efficient method is provided for preparing secondary aminoisobutylalkoxysilanes by reacting hydridoalkoxysilanes with secondary methallylamines in the presence of a hydrosilation catalyst.

Description

Invention field [0001] The present invention relates to an efficient method for preparing secondary amino isobutyl alkoxy silane via noble metal-catalyzed hydrosilation between secondary methallylamine and hydrogenated alkoxysilane. Background of the invention [0002] Secondary amino isobutyl alkoxy silane can be prepared by various chemical methods. Recently, providing cross-linking sites for alkoxy silane functional polyurethane has proved its commercial value in polyurethane sealants (EP 676,403). However, the preparation of such silanes has a certain degree of complexity in realization. [0003] Me(MeO) 2 SiCH 2 CHMeCH 2 The preparation of NHMe is reported (Journal of Organic Chemistry, vol. 36, 3120 (1971)) through a series of reactions, including methallyl chloride and MeSiHCl 2 The hydrosilation effect of this product and a large excess of MeNH 2 The reaction of and the reaction of the resulting cyclic silazane with MeOH. A similar version of trialkoxysilane is prepared i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B61/00C07F7/18
CPCC07F7/1876C07F7/10
Inventor R·S·乔德莱斯M·A·菲利普考夫斯基C·L·小施灵
Owner GENERAL ELECTRIC CO