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Method for synthesizing diethanolamine acrylate compounds

A technology of diethanolamine acrylate and diethanolamine, which is applied in the field of synthesis of diethanolamine acrylate compounds, can solve the problems of environmental pollution, difficulty in recycling, and high catalyst price, and achieve high yield, mild preparation reaction conditions, and low cost. Effect

Inactive Publication Date: 2016-04-20
CHINA NAT OFFSHORE OIL CORP +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patent CN201180017839.0 uses tetrabutyl titanate as a catalyst, butyl acrylate and methyldiethanolamine for transesterification reaction, the catalyst price is high in the process of this method, it is not easy to recycle, and pollutes the environment
The paper (Chemical Communications, 2011, 47, 11697-11699) used dicyclohexylcarbodiimide DCC and dimethylaminopyridine DMAP as esterification catalysts, and prepared by reaction of acrylic acid and long-chain alkylmethyldiethanolamine quaternary ammonium salt product, the catalyst in this reaction is expensive and not suitable for industrial production

Method used

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  • Method for synthesizing diethanolamine acrylate compounds

Examples

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Effect test

Embodiment 1

[0017] In the reactor that 5000ml is equipped with reactive distillation unit, add 1720g methyl acrylate, 500g toluene, nitroxide free radical piperidinol polymerization inhibitor 15.4g, the zinc bromide catalyst supported by 37.9gZSM-5 molecular sieve (loading capacity 14 %), turn on the stirring, raise the temperature to 70°C, add 595g of methyldiethanolamine dropwise, raise the temperature to reflux, and control the reflux ratio to 8:1. The reaction was detected by gas chromatography. After the reaction was completed, the catalyst was recovered by filtration and rectified under reduced pressure to obtain 911 g of methyldiethanolamine diacrylate with a purity greater than 99%.

Embodiment 2

[0019] In the reactor that 5000ml is equipped with reactive distillation unit, add 2000g methyl methacrylate, 500g heptane, hydroquinone monomethyl ether polymerization inhibitor 16.7g, the zinc bromide catalyst (loading capacity) of 34.4g gac support 22%), stirred, raised the temperature to 70°C, added dropwise 595g of methyldiethanolamine, raised the temperature to reflux, and controlled the reflux ratio to 9:1. The reaction was detected by gas chromatography. After the reaction was completed, the catalyst was recovered by filtration and rectified under reduced pressure to obtain 944 g of methyldiethanolamine dimethacrylate with a purity greater than 99%.

Embodiment 3

[0021] In the reactor that 5000ml is equipped with reactive distillation unit, add 2150g methyl acrylate, 550g cyclohexane, piperidine free radical phosphite triester polymerization inhibitor 17.3g, the zinc bromide catalyst ( Loading capacity 18%), stirring, heating up to 70°C, adding 905g of phenyldiethanolamine dropwise, heating up to reflux, and controlling the reflux ratio to 7:1. The reaction was detected by gas chromatography. After the reaction, the catalyst was recovered by filtration and rectified under reduced pressure to obtain 983 g of phenyldiethanolamine diacrylate with a purity greater than 99%.

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Abstract

The invention relates to a method for synthesizing diethanolamine acrylate compounds. The method comprises the following steps: adding an organic solvent, a catalyst, a polymerization inhibitor and methyl acrylate or methyl methacrylate into a reactor, dropwisely adding diethanolamine compounds into the reaction system, and reacting at 0-90 DEG C for 0.5-12 hours to generate the diethanolamine acrylate compounds, wherein the mole ratio of the catalyst to the methyl acrylate or methyl methacrylate is 0.01-15%, the mole ratio of the methyl acrylate or methyl methacrylate to the diethanolamine compounds is 2.0:1-10.0:1, and the catalyst is supported zinc bromide. The method can be used for efficiently preparing the diethanolamine acrylate products under mild experimental conditions in an environment-friendly mode.

Description

technical field [0001] The invention discloses a method for synthesizing diethanolamine acrylate compounds, and relates to the field of ester synthesis reactions, in particular to a method for preparing diethanolamine acrylate compounds through transesterification reactions between methyl acrylate compounds and diethanolamine compounds. Background technique [0002] Diethanolamine acrylate compounds are an important class of fine chemical intermediates. This type of compound has both amine and vinyl functional groups with high reactivity. It can be widely used in polymer flocculants, zwitterionic crosslinking agents, Quaternary ammonium antibacterial agents, polycarboxylate superplasticizers, drilling mud additives and many other fields. In recent years, it has been widely concerned by many scientific researchers in various countries. [0003] There are many reports on the synthesis method of diethanolamine acrylate compounds, and the patent CN200910232784.X reports the rea...

Claims

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Application Information

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IPC IPC(8): C07C213/06C07C219/32C07C219/08B01J27/138B01J29/40
CPCC07C213/06B01J27/138B01J29/405B01J2229/18C07C219/32C07C219/08
Inventor 周立山宋晓莉游娜滕厚开
Owner CHINA NAT OFFSHORE OIL CORP
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