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Process for preparing esteramide compounds

A compound and amide ester technology, applied in the field of preparing amide ester compounds, can solve the problems of lowering reaction kinetics, lowering productivity and the like of reaction temperature

Active Publication Date: 2013-07-10
RHODIA OPERATIONS SAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, lowering the reaction temperature significantly reduces the kinetics of the reaction, and thus the productivity of the process

Method used

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  • Process for preparing esteramide compounds
  • Process for preparing esteramide compounds
  • Process for preparing esteramide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1 (comparison): dimethylamine (gas) joins in Mixture of IRIS / sodium methoxide In-T=20℃

[0074] A solution of sodium methoxide in methanol (50 wt % solution, weight 18.8 g) and 304 g of Rhodia under the trade name A mixture of 2-methyl-glutaric acid diester, 2-ethyl-succinic acid diester and adipate diester sold by IRIS was added to a well-stirred 1-liter double-jacketed reaction set with mechanical stirring and pre-dried device.

[0075] The reaction medium was seen to have an orange color.

[0076] The temperature of the reaction mixture was stabilized at the set point + 20° C. and dimethylamine gas was bubbled through the reaction medium comprising the mixture of sodium methoxide and diester for two hours (82 g of dimethylamine were added, 5% relative to the diester molar excess).

[0077] The temperature of the reaction medium is kept constant throughout the sparging period.

[0078] The temperature of the reaction medium is maintained at +20°...

Embodiment 2

[0088] Embodiment 2 sodium methylate joins in In IRIS / Dimethylamine Mixtures - Effect of Temperature

[0089] In a well-stirred 1-liter double-jacketed reactor equipped with mechanical stirring and pre-dried, dimethylamine (pure DMA, 83 g, 5% molar excess relative to the diester) was introduced and dissolved in 304 g of by Rhodia under the trade name In the mixture of 2-methylglutaric acid diester, 2-ethylsuccinic acid diester and adipate diester sold by IRIS.

[0090] The temperature of the reaction medium is stabilized at the desired set point (refer to Table 2 below), and a solution of sodium methoxide in methanol (50 wt % solution, weight 18.8 g) is poured into the In the reaction mixture of a mixture of amine and diester.

[0091] Once the pouring is complete, the temperature of the reaction medium is kept constant until more than 96% of the charged diester load has been consumed.

[0092] Excess dimethylamine was distilled under reduced pressure (about 200 mbars)...

Embodiment 3

[0101] Example 3 IRIS added to sodium methoxide / dimethylamine mixture - effect of temperature - over amount of DMA effects.

[0102] Dimethylamine in methanol (50 wt % solution, weight 188 g) and sodium methoxide in methanol (50 wt % solution, weight 18.8 g) were introduced into a well-stirred 1 liter double clamp provided with mechanical stirring and pre-dried in the reactor.

[0103] The temperature of the reaction medium is stabilized at the desired stated value, and within a defined period of time, 304 g of Rhodia under the trade name A mixture of 2-methylglutaric acid diester, 2-ethylsuccinic acid diester and adipate diester sold by IRIS was poured into a reaction mixture comprising dimethylamine and sodium methoxide.

[0104] Once the pouring is complete, the temperature of the reaction medium is kept constant until more than 96% of the charged diester load has been consumed.

[0105] Excess dimethylamine was distilled under reduced pressure (about 200 mbars) ...

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Abstract

The present invention relates to a process for preparing esteramide compounds. More particularly, the invention relates to a process for preparing esteramide compounds by reaction between a diester and an amine, in the presence of a basic compound, in which - the amine is solubilized in an organic solvent or in the diester, - when the amine is solubilized in an organic solvent, the diester is added to the reaction mixture comprising the amine and the basic compound, - when the amine is solubilized in the diester, the basic compound is added to the reaction mixture comprising the amine and the diester (II), - the reaction is carried out at a temperature greater than or equal to 30 DEG C, - the amine is present in a molar excess ranging from 0.01 to 50%, relative to the diester.

Description

technical field [0001] The present invention relates to a process for the preparation of amide ester compounds. [0002] More specifically, the present invention relates to a method for preparing amidate compounds by reaction between diesters and amines. Background technique [0003] Amide ester compounds are well known for their use as solvents, in particular in plant protection applications, as described, for example, in document WO 2009 / 092795. [0004] There are several routes for obtaining said amide ester compounds. [0005] Document US 4588833 describes a process for the preparation of amide esters by cobalt-catalyzed high-temperature reaction of unsaturated amides with alcohols and carbon monoxide. [0006] Document US 3417114 describes a kind of simultaneous preparation formula in embodiment 9 and is MeOOC-(CH 2 ) 3 -CONMe 2 The amide ester compound (DMGME) and the formula is Me 2 NOC-(CH 2 ) 3 -CONMe 2 diamide compound (TMG), followed by distillation to se...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02
CPCC07C231/02C07C233/05C07C231/14
Inventor T·维达尔R·雷切德M·古格利日
Owner RHODIA OPERATIONS SAS