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Preparation method of organosilicium compounds

An organosilicon compound, compound technology, applied in the direction of silicon organic compounds, organic chemistry, chemical instruments and methods, etc., can solve the problems of yield and productivity to be improved, unfavorable operating factors of solid NBS, expensive and other problems

Inactive Publication Date: 2008-05-21
RHODIA CHEM SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] 1. In industrial methods, the use of solid NBS is a very unfavorable operational factor
[0019] 2. This method needs to be improved in terms of yield and productivity
[0020] 3. This method is relatively expensive and should be improved economically

Method used

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  • Preparation method of organosilicium compounds
  • Preparation method of organosilicium compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0231] Example 1: Embodiment in which Ox=NBS and Ox and B are used in stoichiometric amounts relative to the precursor (II)

Embodiment 2

[0232] · Embodiment 2: where Ox=Br 2 And an embodiment in which Ox is used in a stoichiometric amount relative to the precursor (II). B is used in a stoichiometric amount relative to the released HBr

Embodiment 3

[0233] Example 3: Workup steps a) to d) then steps e) to h)

[0234] The examples above thus show that:

[0235] • NBS and pyridine can be used in stoichiometric amounts relative to the precursor. This result is particularly advantageous since excess pyridine is very difficult to remove from the medium.

[0236] • From a cost point of view bromine can be advantageously substituted for NBS, even though its use implies doubling the amount of pyridine (in this case twice the hydrobromic acid to be captured).

[0237] • Post-treatment in one or more steps may improve the quality of the final product by facilitating the almost complete removal of pyridine residues without reducing the Silcaf content of the sample.

[0238] Embodiment 1: the usage charge of stoichiometric NBS / pyridine system:

[0239] · Precursor (II)

20.0g

57mmol

Ox=N-bromosuccinimide 99%

10.13g

57mmol

· B = pyridine

4.5g

57mmol

Solvent = dichloromethane

...

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PUM

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Abstract

The invention relates to the synthesis of functionalised organosilicon compounds comprising at least one active azo group having formula (I): [(G<0>)3SiO1 / 2]m[(G<0>)2SiO2 / 2]n [G<0>SiO3 / 2]o[SiO4 / 2]p[(G<2>)a(G<1>)a'(Z-CO-HN=NH-CO-A)SiO (3-a-a') / 2]. The inventive method consists in using at least one hydrazino (-HN-NH-) precursor (II) of the compound (I) and oxidising the precursor (II) into an azo group specific to the compound (I) with the aid of an oxidising system comprising at least one oxidant (Ox) and at least one base (B). The method is characterised in that: 1) Ox is selected from among the oxidants that can oxidise a hydrazine function into an azo function, with or without the exclusion of N-bromosuccinimide (NBS), preferably from among halogens, halogenated derivatives and mixtures thereof and betterstill from the group containing bromine, tert-butyl hypochlorite, trichloroisocyanuric acid, chlorine and mixtures of same; 2) and / or Ox (optionally B) is / are used in stoichiometric quantities in relation to the precursor (II); 3) and / or the organosilicon compounds (I) thus prepared are subjected to a purification post-treatment which is intended to eliminate any unwanted residues of the base B used, on the condition that, when NBS is not excluded, characteristic (1) is combined with characteristic (2) and / or characteristic (3). The invention also relates to pure compounds (I) that can be obtained using said method.

Description

technical field [0001] The present invention relates to the synthesis of functionalized organosilicon compounds. [0002] The present invention more particularly relates to organosilicon compounds which contain at least one activated azo group. Such activation can result, for example, from the presence of a carbonyl group near the nitrogen. The silicone part of these compounds may contain, for example, hydrolyzable or condensable groups of the type ≡SiOR or ≡SiOH. Background technique [0003] Such organosilicon compounds with available activated azo groups (such as those with the group -CO-N=N-CO-) are very useful, especially for the synthesis of organic compounds useful in the agrochemical or pharmaceutical fields. Reactive molecules (eg nitrogen-containing heterocycles) are used as dienophiles, eg in hetero-Diels-Alder reactions. [0004] However, few of these compounds are available, not least because of their difficulty in preparing. It would therefore be desirable ...

Claims

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Application Information

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IPC IPC(8): C07F7/18
CPCC07F7/1892C07F7/08C07F7/18
Inventor S·斯特兰
Owner RHODIA CHEM SA