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A kind of preparation method of 2,2-oxalamido-bis[ethyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)] propionate

A technology of phenylpropionate and di-tert-butyl, applied in the field of chemical synthesis, can solve the problems of unstable product quality index, difficult to guarantee crystal form, large product melting range, etc., and achieves short reaction time, mild reaction conditions, The effect of improving product yield

Active Publication Date: 2017-08-15
ZHEJIANG HUAYI ENG DESIGN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above-mentioned 2,2-oxalamido-bis[ethyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)]propionate preparation method mainly has the following disadvantages: (1) the reaction time is long; (2) The quality index of the product is unstable, the melting range of the product is large, and the crystal form is difficult to guarantee; (3) The organotin catalyst remains in the product, which is highly toxic

Method used

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  • A kind of preparation method of 2,2-oxalamido-bis[ethyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)] propionate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Feed nitrogen into the reactor, and add raw materials 3-(3,5-di-tert-butyl-4-hydroxyl) methyl phenylpropionate (raw material A) 332Kg and N, N'-bis(hydroxyethyl) at one time ) oxamide (raw material B) 85.8Kg, add ethyl titanate catalyst, the amount of catalyst is 0.5% of the mole number of raw material A, heat up to 160°C for 2 hours, then heat up to 190°C for 3 hours, while reacting Distill out the by-product methanol or ethanol. After the reaction, lower the temperature of the material in the reactor to 60°C, add methanol solvent for cooling and crystallization, and obtain the product 2,2-oxalamido-bis[ethyl-3-(3 , 5-di-tert-butyl-4-hydroxyphenyl)] propionate.

[0025] The product was sampled, and the purity of the product was detected by liquid chromatography. The product yield based on raw material B was 90.5%.

Embodiment 2

[0027] Feed nitrogen into the reactor, and add raw materials 3-(3,5-di-tert-butyl-4-hydroxyl) methyl phenylpropionate (raw material A) 332Kg and N, N'-bis(hydroxyethyl) at one time ) oxamide (raw material B) 83.8Kg, add butyl titanate catalyst, the amount of catalyst is 1% of the mole number of raw material A, heat up to 155°C for 1.5 hours, then heat up to 185°C for 2.5 hours, while reacting Distill out the by-product methanol or ethanol. After the reaction, reduce the temperature of the material in the reactor to 60°C, add ethanol solvent for cooling and crystallization, and obtain the product 2,2-oxalamido-bis[ethyl-3-(3 , 5-di-tert-butyl-4-hydroxyphenyl)] propionate.

[0028] The product was sampled, and the purity of the product was detected by liquid chromatography, and the product yield based on raw material B was 94.2%.

Embodiment 3

[0030] Feed nitrogen into the reactor, and add raw materials 3-(3,5-di-tert-butyl-4-hydroxyl) methyl phenylpropionate (raw material A) 332Kg and N, N'-bis(hydroxyethyl) at one time ) oxamide (raw material B) 81.9Kg, add ethyl acetoacetate titanium complex catalyst, the amount of catalyst is 2% of the mole number of raw material A, heat up to 150°C for 1 hour, then heat up to 160°C for 2 hours , while reacting, the by-product methanol or ethanol is distilled out. After the reaction, the temperature of the material in the reactor is lowered to 65 ° C, and n-propanol solvent is added to cool and crystallize, and the product 2,2-oxalamido-bis[ethyl Base-3-(3,5-di-tert-butyl-4-hydroxyphenyl)]propionate.

[0031] The product was sampled, and the purity of the product was detected by liquid chromatography, and the product yield based on raw material B was 93.5%.

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Abstract

The invention discloses a synthesis method of a metal ion passivator 2,2-oxamido-di[ethyl-3-(3,5-di-tertiary butyl-4-hydroxyphenyl)] propionate with a hindered phenol antioxidant structure. The synthesis method is implemented by taking 3-(3,5-di-tertiary butyl-4-hydroxy)] phenyl propionate and N,N'-di(hydroxyethyl) oxamide as raw materials and taking organic titanium or organic zirconium as a catalyst through two-section temperature-controlled synthesis at a temperature of 150-160 DEG C and at a temperature of 160-190 DEG C. The synthesis method disclosed by the invention has the advantages of short reaction time, no toxic catalyst residue, stable product quality, and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a method for synthesizing a metal ion passivator with a hindered phenol antioxidant structure, in particular to a 2,2-oxalamido-bis[ethyl-3-(3,5- The preparation method of di-tert-butyl-4-hydroxyphenyl)] propionate. Background technique [0002] When the polymer is in contact with metal, especially copper, even if the polymer contains a large amount of hindered phenolic antioxidant, it cannot inhibit the oxidation reaction caused by the catalysis of copper ions. In order to effectively prevent this reaction, the ideal rubber and plastic products can be produced. [0003] 2,2-oxalamido-bis[ethyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)]propionate is a metal ion passivator with hindered phenolic antioxidant structure Because of the hindered phenol and oxamide tube energy groups in the molecular structure, it has dual functions of anti-oxidation and metal ion passivation. It is widely...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/56C07C231/12
Inventor 唐友明赵外荣
Owner ZHEJIANG HUAYI ENG DESIGN
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