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Ethane 1,1,2 - ethyl ester tricarboxylic acid, preparation method, and application as plasticizer

A technology of ethyl tricarboxylate and ethyl halogenated carboxylate is applied in the field of preparation of ethyl ethane-1,1,2-tricarboxylate, which can solve the problems affecting the development of citric acid ester plasticizers and the development of citric acid ester plasticizers. The shortage of supply in the acid market, unfavorable recovery and reusability, etc., achieve the effect of simple post-processing process, short reaction time and mild reaction conditions

Inactive Publication Date: 2010-05-19
JINGGANGSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the pollution control measures adopted by most production plants are basically terminal treatment methods, which are not only not conducive to the recovery of useful resources that can be reused, but also require a large investment in equipment and high operating costs, resulting in tight market supply of citric acid, which in turn affects the Development of Citrate Plasticizers
[0006] The application of ethyl ethane-1,1,2-tricarboxylate as a plasticizer has not been reported yet

Method used

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  • Ethane 1,1,2 - ethyl ester tricarboxylic acid, preparation method, and application as plasticizer
  • Ethane 1,1,2 - ethyl ester tricarboxylic acid, preparation method, and application as plasticizer

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Embodiment 1

[0030] Embodiment 1, ethane-1,1, the preparation method of 2-tricarboxylic acid ethyl ester, get diethyl malonate and strong alkali solution to obtain intermediate product A at 70 ℃ of reaction in advance for 10 minutes, then to intermediate product A Add a catalyst that is 0.5% by weight of diethyl malonate, and dropwise add the ethyl halocarboxylate to continue the reaction within 30 minutes. The reaction was carried out for 3 hours. After the reaction was completed, the inorganic salt impurities were removed, and the ethane-1,1,2-tricarboxylic acid ethyl ester was obtained by distillation under reduced pressure; Ethanol solution; the catalyst is potassium iodide, sodium iodide or elemental iodine; ethyl chloroacetate or ethyl bromoacetate is the catalyst; diethyl malonate: sodium methoxide or sodium ethoxide: moles of ethyl haloacetate The metering ratio is 1.0:1:1.0.

Embodiment 2

[0031] Embodiment 2, ethane-1,1, the preparation method of 2-tricarboxylic acid ethyl ester, get diethyl malonate and strong alkali solution to obtain intermediate product A at 80 ℃ of reaction in advance for 30 minutes, then to intermediate product A Add the catalyst that is 1% by weight ratio of diethyl malonate, and drop the ethyl halocarboxylate in 50 minutes to continue the reaction. The reaction was carried out for 15 hours, and after the reaction was completed, the inorganic salt impurities were removed, and the ethane-1,1,2-tricarboxylic acid ethyl ester was obtained by distillation under reduced pressure; wherein: the strong base solution was sodium methylate or sodium ethylate with a mass percentage concentration of 21%. Ethanol solution; the catalyst is potassium iodide, sodium iodide or elemental iodine; ethyl chloroacetate or ethyl bromoacetate is the catalyst; diethyl malonate: sodium methoxide or sodium ethoxide: moles of ethyl haloacetate The metering ratio is ...

Embodiment 3

[0032] Embodiment 3, ethane-1,1, the preparation method of 2-tricarboxylic acid ethyl ester, get diethyl malonate and strong alkali solution and obtain intermediate product A at 75 ℃ in advance for 20 minutes, then to intermediate product A Add the catalyst that is 0.8% by weight ratio of diethyl malonate, and dropwise add the ethyl halocarboxylate in 40 minutes to continue the reaction. The reaction was carried out for 10 hours, and after the reaction was completed, the inorganic salt impurities were removed, and the ethane-1,1,2-tricarboxylic acid ethyl ester was obtained by distillation under reduced pressure; wherein: the strong base solution was sodium methylate or sodium ethylate with a mass percentage concentration of 20%. Ethanol solution; the catalyst is potassium iodide, sodium iodide or elemental iodine; ethyl chloroacetate or ethyl bromoacetate is the catalyst; diethyl malonate: sodium methoxide or sodium ethoxide: moles of ethyl haloacetate The metering ratio is 1...

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Abstract

This invention relates to a method for preparing ethyl ethane-1, 1, 2-tricarboxylate and its application as plasticizer. The method comprises: reacting diethyl malonate and strong alkaline solution at70-80 deg.C for 10-30 min to obtain intermediate A, adding catalyst 0.5-1 wt.% of diethyl malonate, dropping halogenated ethyl carboxylate within 30-50 min, reacting at 70-80 deg. C for 3-15 h, removing inorganic salt impurities, and vacuum-distilling to obtain ethyl ethane-1,1,2-tricarboxylate. The method has such advantages as simple process, mild reaction conditions, short reaction time, no obvious waste discharge (only NaCl or NaBr as byproduct), and simple post-treatment.

Description

technical field [0001] The present invention relates to ethyl ethane-1,1,2-tricarboxylate, its preparation method and its application as a plasticizer. Background technique [0002] Among the existing plastic plasticizers, dioctyl phthalate (DOP) and dibutyl phthalate (DBP) are dominant. However, DOP and DBP are toxic in themselves and are banned in the European Union and many countries (including phthalic acid products). Citrate products are non-toxic "green" environmentally friendly plastic plasticizers recognized in the world at present, widely used in food and medical instrument packaging, cosmetics, daily necessities, toys, military supplies, etc., with good compatibility and high plasticizing efficiency , non-toxic, easy to be biodegraded and low volatility, etc., excellent cold resistance, light resistance and water resistance, and has shock resistance in the resin, and does not grow mold. [0003] The traditional synthesis method of citrate plasticizer is to use ci...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/00C07C69/34C08K5/11
Inventor 隋岩曾锡瑞李新发方小牛
Owner JINGGANGSHAN UNIVERSITY