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Method for preparing alkoxyamines by photolysis of dithiocarbamates

A technology of dithiocarbamate and alkoxylamine, which is applied in the field of synthesizing N--N--O-hydroxylamine alkoxy-amine, which can solve the problems of difficult purification steps and amplification

Inactive Publication Date: 2008-07-30
ARKEMA FRANCE SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] These methods require difficult purification steps that may produce large effluents that may or may not contain metals, or steps that cannot be scaled up industrially such as chromatography on silica

Method used

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  • Method for preparing alkoxyamines by photolysis of dithiocarbamates
  • Method for preparing alkoxyamines by photolysis of dithiocarbamates
  • Method for preparing alkoxyamines by photolysis of dithiocarbamates

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Experimental program
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Effect test

Embodiment 1

[0031] Preparation of S-(1-methyl-1-carboxyethyl)-N,N-diethyldithiocarbamate

[0032]

[0033] 6.68 g of 2-bromoisobutyric acid (0.04 mol) and 60 ml of water were introduced into a 100 ml glass round bottom flask. By adding Na 2 CO 3 The medium is neutralized to pH=9. Next, 9 g of sodium diethyldithiocarbamate trihydrate (0.04 mol) are added, and the medium is then stirred at ambient temperature for 15 hours. The reaction mixture was then acidified to pH=2 by adding 33% hydrochloric acid. The white precipitate that appeared was recovered by filtration and dried under vacuum. Thus, 3.1 g of S-(1-methyl-1-carboxyethyl)-N,N-diethyldithiocarbamate (yield = 33%) were obtained from 1 HNMR to characterize.

[0034] 1 H NMR (CDCl 3 -300MHz): 1.25-1.30ppm (m, 6H); 1.78ppm (s, 6H); 3.5-4ppm (m, 4H).

[0035] Furthermore, N-tert-butyl-1-diethylphosphono-2,2-dimethylpropylnitroxy (SG1) was prepared according to the teaching of EP1349862.

[0036] Introduced into the photochem...

Embodiment 2

[0042] The procedure in Example 1 was followed except that the dithiocarbamate / nitrogen ratio was increased to 1.5 instead of 1.3, i.e. 6.93 g dithiocarbamate (23.5 mmol) and 4.62 g SG1 ( 15.7 mmol).

[0043] Thus, 5.4 g of alkoxyamine (I) were yielded, ie a yield of 90%.

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Abstract

The invention concerns a novel method for preparing alkoxyamines from nitroxide and dithiocarbamate by photolysis reaction. The method does not generate effluent containing metals, can be performed in batch or continuously and is carried out at a temperature lower than known methods for the synthesis of alkoxyamines.

Description

technical field [0001] The invention relates to a method for preparing alkoxyamines by photochemical reaction between dithiocarbamate organic compounds and nitroxide. This method is particularly suitable for the synthesis of N-(tert-butyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamine alkane Oxy-amine. [0002] The alkoxyamines prepared according to the process of the invention can be used in the synthesis of polymer materials or polymer additives (for example of the following types: dispersants, rheology modifiers, emulsifiers, impact additives) in the fields of : Plastics, elastomers, paints, adhesives, cosmetics, paper, hydraulic adhesives (cement or plaster), ceramics, asphalt, lubricants, petroleum production, emulsification or coatings (controlled salts of active ingredients analysis). Background technique [0003] The synthesis of alkoxyamines can be carried out by various methods. For example, mention may be made of the article (re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40
CPCC07C333/20C07C333/30C07F9/4006C07C239/08C07C239/20
Inventor 丹尼斯·伯廷让-卢克·库图里尔迪迪尔·吉梅斯奥利维尔·格雷特约安·吉勒诺伊夫
Owner ARKEMA FRANCE SA