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Method for preparing bisphenolmonoacryates compounds antioxidant

A monoacrylate and compound technology, which is applied in the field of preparation of bisphenol monoacrylate compound antioxidants, can solve the problems of increased equipment investment and processing costs, waste of triethylamine raw materials, troublesome processing, etc., and achieves reduction in processing process, facilitate industrial production, and improve the effect of molar yield

Inactive Publication Date: 2008-03-26
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In the mid-1980s, with the increasing production and application of polymer materials, traditional phenolic antioxidants could no longer meet the anti-aging requirements of polymer materials for their own mechanical properties and appearance color.
The treatment process of waste water is more troublesome, which increases equipment investment and processing costs
In addition, the waste of triethylamine raw materials also increases the cost of raw materials during production, which is also unfavorable for the formation of economic scale production

Method used

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  • Method for preparing bisphenolmonoacryates compounds antioxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A one-step synthesis process is adopted. Add 2,2'-ethylene bis(4,6-di 1691g (3.424mol) of p-amyl)phenol, 259g (3.596mol) of acrylic acid, and 7800mL of n-hexane. The air in the kettle was replaced with nitrogen. Heat, stir, and raise the temperature to 40-50°C. Keep the temperature constant, and start to add 194g (1.259mol) of phosphorus oxychloride raw material dropwise, and finish adding in 40-50 minutes. While adding phosphorus oxychloride dropwise, 445 g (4.405 mol) of triethylamine raw material was added dropwise, and the time for dropping the triethylamine raw material was 120 to 130 minutes. After adding the triethylamine raw material, the temperature of the reaction solution was raised to 63-66°C. At 63-66°C, keep warm for 150-160 minutes.

[0033] After the reaction is finished, the temperature of the reaction solution is cooled to room temperature, and the material is discharged, and the obtained reaction mixture is a solid-liquid mixture. After filtering,...

Embodiment 2

[0036] Add 2,2'-ethylene bis(4,6-di 1691g (3.424mol) of p-amyl)phenol, 246g (3.424mol) of acrylic acid, and 7800mL of n-hexane. The air in the kettle was replaced with nitrogen. Heat, stir, and raise the temperature to 40-50°C. Keep the temperature constant, and start to add 176g (1.141mol) of phosphorus oxychloride raw material dropwise, and finish adding in 50-60 minutes. While adding phosphorus oxychloride dropwise, 346g (3.424mol) triethylamine raw material was added dropwise, and the synthesis reaction process was completed in the same way as in Example 1. As a result, 1436 g of 2-[1-(2-hydroxyl-3,5-dipentylphenyl)-ethyl]-4,6-dipentylphenyl acrylate of the present invention was obtained. Appearance is white or light yellow crystal, melting point: 117.9-118.4. , HPLC purity: 99.4%. The product molar yield is 76.1%. Elemental analysis: C, 81.2; H, 9.9; O, 8.8. (Theoretical: C, 81.0; H, 10.2; O, 8.8).

Embodiment 3

[0038] Add 2,2'-ethylene bis(4,6-di 1691g (3.424mol) of p-amyl)phenol, 295g (4.109mol) of acrylic acid, and 7800mL of n-hexane. The air in the kettle was replaced with nitrogen. Heat, stir, and raise the temperature to 40-50°C. Keep this temperature constant, start to drop 254g (1.644mol) of phosphorus oxychloride raw material, and add it in 50-60 minutes. While adding dropwise phosphorus oxychloride, dropwise add 664g (6.574mol) triethylamine raw material, complete the synthetic reaction process by the same method of embodiment 1. As a result, 1412 g of 2-[1-(2-hydroxy-3,5-dipentylphenyl)-ethyl]-4,6-dipentylphenyl acrylate of the present invention was obtained. Appearance is white or yellowish crystal, melting point: 117.3-118.5. , HPLC purity: 99.0%. The product molar yield is 74.5%. Elemental analysis: C, 81.1; H, 9.8; O, 9.1. (Theoretical: C, 81.0; H, 10.2; O, 8.8).

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Abstract

The present invention is technological process of preparing bisphenol monoacrylate compound as oxidant with bisphenol compound, acrylic acid and phosphorus oxychloride as materials, triethylamine as acid absorbent and aliphatic hydrocarbon as solvent, and through acyl chlorination and esterification in a reactor. The technological conditions include the molar ratio between bisphenol compound and acrylic acid of 1 to 1.05, the molar ratio between acrylic acid and phosphorus oxychloride of 3 to 1.05, the molar ratio between phosphorus oxychloride and triethylamine of 1 to 3.5; reaction temperature of 63-66 deg.c and reaction time of 150-155 min. After reaction, the resultant is filtered to eliminate solid triethylamine hydrochloride, the filtrate is cooled to re-crystallize to produce white crystal product of smelting point 117.5-18.6 deg.c. The present invention is simple, and has high bisphenol monoacrylate compound yield and low material consumption.

Description

technical field [0001] The present invention relates to a preparation method of a bisphenol monoacrylate compound antioxidant, the bisphenol monoacrylate compound specifically refers to the following formula (I) [0002] [0003] In formula (I): R 1 =C 4 ~C 5 Straight chain alkanes or alkanes with branched chains; [0004] R 2 = H; CH 3 . [0005] Bisphenol monoacrylate compound is an excellent antioxidant product, mainly used in synthetic rubber, polyolefin plastic, engineering plastic and other polymer materials. The stabilization mechanism of bisphenol monoacrylate antioxidants is usually called a bifunctional stabilization mechanism. [0006] Studies have shown that this type of antioxidant is very effective for the thermal and oxidative aging resistance of polymers. Background technique [0007] In the mid-1980s, with the increasing production and application of polymer materials, traditional phenolic antioxidants could no longer meet the anti-aging requireme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C67/08C08K5/107
Inventor 杜飞杜昭辉常美荣
Owner CHANGZHOU UNIV
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