Preparation method of ultraviolet absorbent intermediate etocrilene (ETO)

The technology of an ultraviolet absorber and relying on toril is applied in the preparation of organic intermediates and in the field of preparation of sunscreen intermediates relying on toril. Achieve the effect of reducing difficulty and equipment investment, reducing amide by-products, and good separation

Active Publication Date: 2013-08-14
ANHUI SHENGNUOBEI CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method does not have much industrial production value due to the use of expensive and difficult-to-obtain raw materials, toxic catalysts and solvent diethyl ether

Method used

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  • Preparation method of ultraviolet absorbent intermediate etocrilene (ETO)
  • Preparation method of ultraviolet absorbent intermediate etocrilene (ETO)
  • Preparation method of ultraviolet absorbent intermediate etocrilene (ETO)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Add 182kg benzophenone, 226kg ethyl cyanoacetate, 10Kg di-n-butylamine, 5.7Kg propionic acid and 273Kg cyclohexane into the reactor, heat up to reflux (reaction temperature is 85-87°C), and continuously separate the reaction Produced water, when the amount of water separated by the reaction is very small, the reaction is completed, and it takes about 14 hours to obtain 16Kg of water. Directly lower the temperature to 50-55°C, transfer 16Kg of water into the kettle, add 75Kg of preheated fresh water, stir for 15 minutes, let stand for 30 minutes, and separate the liquids to obtain 105Kg of water layer and 661.2Kg of oil layer.

[0059] Gained water layer 105Kg is simply distilled under-700mmHg vacuum until anhydrous steams out, and obtains water 73Kg, and this water can be used for embodiment 2; Distillation bottom 13.4Kg, is the catalyst of reclaiming, can be used for embodiment 2 and apply. .

[0060] The obtained oil layer was 661.2Kg, distilled at normal pressure un...

Embodiment 2

[0064] Embodiment 2 has investigated the mechanical application of each reclaimed material, to illustrate the applicability of the present invention.

[0065] Add benzophenone and ETO mixture 80Kg that reclaims in embodiment 1 in reactor, new benzophenone 132Kg; Add in embodiment 1 and reclaim ethyl cyanoacetate 138Kg, new ethyl cyanoacetate 95Kg; Add the catalyst that reclaims 13.4Kg, add new 1.5Kg di-n-butylamine and 0.8Kg propionic acid, add recovered cyclohexane 239Kg and new cyclohexane 25Kg, heat up to reflux (reaction temperature is 86-88°C), and continuously separate the reaction products When the amount of water separated by the reaction is very small, the reaction is completed, and it takes about 12 hours to obtain 21Kg of water. Directly lower the temperature to 50-55°C, transfer the separated 21Kg of water into the kettle, then add 73Kg of preheated recovered water, stir for 15 minutes, let stand for 30 minutes, and separate the liquids to obtain 106.4Kg of water l...

Embodiment 3

[0071] Add 182kg benzophenone, 226kg ethyl cyanoacetate, 6.6kg piperidine, 11.2kg n-octanoic acid and 275kg n-heptane in the reactor, heat up to reflux (reaction temperature is 99-102°C), and continuously separate the reaction products When the amount of water separated by the reaction is very small, the reaction is completed, and it takes about 13 hours to obtain 15.9kg of water. Directly lower the temperature to 52-55°C, transfer 15.9kg of water into the kettle, then add 75kg of preheated tap water, stir for 20 minutes, let stand for 40 minutes, and separate the liquids to obtain 107kg of water layer and 658kg of oil layer.

[0072] Gained water layer is simply distilled under -700mmHg vacuum until anhydrous is evaporated, and 75kg of water is obtained, which can be recycled; the distillation bottom 17.2kg is the catalyst recovered and can be recycled.

[0073] The resulting oil layer was distilled at normal pressure until the flow was cut off to obtain 265 kg of n-heptane; ...

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Abstract

The invention relates to a preparation method of an ultraviolet absorbent intermediate etocrilene (ETO). The preparation method comprises the following steps of: 1, adding benzophenone, ethyl cyanoacetate, a catalyst and a water-insoluble solvent into a condensation reaction kettle, carrying out backflow water distribution reaction for 12-15h, and then, cooling to 50-55 DEG C, wherein the excessive equivalent of the ethyl cyanoacetate relative to the benzophenone is 0.2-5; 2, washing the reaction liquid by using water, and separating the liquid to respectively obtain a water layer and an organic layer; distilling the recycled water at the water layer at normal pressure, dissolving distillation tailings by using a solvent same as the solvent used in the step 1, and then, replenishing a proper quantity of catalyst to obtain a product, wherein the distilled recycled water is used in the step 2, and the product is used in the step 1; and distilling the recycled solvent at the organic layer at normal pressure, and carrying out reduced pressure distillation to recycle the excessive ethyl cyanoacetate, wherein the recycled solvent and ethyl cyanoacetate are used in the step 1; 3, carrying out reduced pressure distillation on the distillation tailings, adding 75-100% of ethanol for crystallizing, and filtering to obtain the etocrilene; and 4, filtering a mother solution obtained in the step 3, recycling the ethanol at normal pressure, and carrying out reduced pressure recycle on the benzophenone and the etocrilene, wherein the recycled ethanol is used in the step 3, and the recycled benzophenone and etocrilene are used in the step 1. The preparation method has the advantages of simplicity in operation, short production period, little environment pollution, low energy consumption, realization of material recycling, and the like.

Description

technical field [0001] The invention relates to a method for preparing an organic intermediate, in particular to a method for preparing an intermediate of sunscreen agent etolylene, and belongs to the technical field of daily chemical industry. Background technique [0002] The ultraviolet absorber octocrylene, the chemical name is 2-cyano-3,3-diphenylacrylate-2-ethylhexyl, the trade name is UV-3039, and the CAS number is 6197-30-4. The English name is Octocrilene, and the English aliases are 2-Ethylhexyl2-cyano-3,3-diphenylpropenoate; 2-Cyano-3,3-diphenyl-2-propa noic acid2-ethylhexyl ester. Its structural formula is as follows: [0003] [0004] Octocrylene is a light yellow liquid with a boiling point of 200°C (13.33Pa), a relative molecular mass of 361, a relative density of 1.0478g / cm (25°C), and a maximum absorption wavelength of ultraviolet rays of 308nm. It has good compatibility with resin and is not colored. It is widely used as light stabilizer in plastics su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/41C07C253/30
Inventor 刘启发王荣宋小明
Owner ANHUI SHENGNUOBEI CHEM TECH
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