Preparation method of sun-screening agent iso-octyl p-methoxycinnamate

A technology of methoxycinnamic acid and p-methoxybenzaldehyde, applied in the field of daily chemical industry, can solve the problems of high equipment material and safety requirements, raw material loss, multiple side reactions, etc., to solve the problem of low quality, reduce Production of waste water and the effect of reducing production costs

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

This method has the following disadvantages: the reaction temperature is high, and more energy is consumed, and at such a high temperature, the material and safety requirements of the equipment are relatively high.
However, the above-mentioned process has the following disadvantages from the actual production: the utilization rate of the reaction raw material methyl acetate or isooctyl ester is not high, the decomposition of acetates under alkal

Method used

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  • Preparation method of sun-screening agent iso-octyl p-methoxycinnamate
  • Preparation method of sun-screening agent iso-octyl p-methoxycinnamate

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Add 68kg p-methoxybenzaldehyde, 300kg toluene, 58Kg malonic acid, 2Kg piperidine and 1.41Kg acetic acid in the reaction kettle, heat up to reflux, react at a reaction temperature of 108-110°C, and continuously separate out the reaction produced Water, react for 4.5 hours to complete the reaction, directly lower the temperature to 10°C, filter with suction, and use the filtrate for the next batch; the filter cake is dried at 80°C, the HPLC content is 99.5%, and the yield is 96%. GS-MS analysis molecular weight is 178, by 1 H-NMR detection confirmed that it was p-methoxycinnamic acid.

Embodiment 2

[0046] Add 68kg p-methoxybenzaldehyde, 350kg toluene, 58Kg malonic acid, 2Kg piperidine and 1.41Kg acetic acid in the reaction kettle, heat up to reflux, react when the reaction temperature is 108-110°C, and continuously separate out the reaction produced Water, reacted for 5.0h to complete the reaction, directly cooled to 12°C, suction filtered, and the filtrate was used for the next batch; the filter cake was dried at 80°C, the HPLC content was 99.2%, and the yield was 95.6%. 1 H-NMR detection confirmed that it was p-methoxycinnamic acid.

Embodiment 3

[0048] Add 68kg p-methoxybenzaldehyde, 250kg toluene, 58Kg malonic acid, 2Kg piperidine and 1.41Kg acetic acid in the reaction kettle, heat up to reflux, react when the reaction temperature is 110-112°C, and continuously separate out the reaction produced water, reacted for 4 hours to complete the reaction, directly lowered the temperature to 8°C, and suction filtered, and the filtrate was used for the next batch; the filter cake was dried at 80°C, the HPLC content was 99.4%, and the yield was 93.5%. 1 H-NMR detection confirmed that it was p-methoxycinnamic acid.

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Abstract

The invention relates to a preparation method of a sun-screening agent OMC (iso-octyl P-Methoxycinnamate). The preparation method comprises the following steps of: 1, adding p-anisaldehyde, malonic acid, a catalyst I organic secondary amine substance, a catalyst II organic acid substance and a water-insoluble organic aromatic hydrocarbon solvent to a condensation reaction kettle, and carrying out reflux water diversion reaction for 4-5 hours; 2, after condensation reaction is finished, cooling to 5-15 DEG C, filtering to obtain a p-methoxycinnamic acid crude product, directly applying filter liquor to next reaction, and optionally supplementing a small quantity of catalysts and solvents to the filter liquor; 3, adding catalyst III macroporous type storng acid cation exchange resin, isooctyl alcohol, the p-methoxycinnamic acid crude product and an aromatic hydrocarbon or aliphatic hydrocarbon solvent to an esterifying reaction kettle, and carrying out reflux water diversion reaction for 2-3 hours; and 4, after esterifying reaction is finished, cooling to 65 DEG C, filtering and recovering the catalysts for mechanical application, washing the filter liquor to neutrality through a 5% sodium carbonate water solution, desolventizing, and rectifying to obtain the final product isooctyl p-methoxycinnamate. The method disclosed by the invention has the characteristics of easiness, convenience, easiness in control, industrial production, low environment pollution, low energy consumption, material recycling, high product purity, and the like.

Description

technical field [0001] The invention relates to a preparation method of sunscreen agent isooctyl p-methoxycinnamate, which belongs to the technical field of daily chemical industry. Background technique [0002] Isooctyl p-methoxycinnamate (OMC) is also known as isooctyl 4-methoxycinnamate, trans isooctyl p-methoxycinnamate, isooctyl p-methoxycinnamate; English name Isooctyl p-methoxycinnamate; CAS number: 83834-59-7; Molecular formula: C 18 h 26 o 3 ; Molecular weight: 290.4. [0003] Isooctyl p-methoxycinnamate is a good absorber of ultraviolet rays in the UVB region, and can effectively prevent ultraviolet rays of 280-330nm. It has a high absorption rate, no irritation to the skin, and good safety. It is almost an ideal sunscreen. [0004] The synthetic technique of isooctyl p-methoxycinnamate mainly contains following several. [0005] Perkin reaction preparation, such as in CN102060832; Asian J.Chem.2007,19 (6): 4945-4947; Rev.Roum.Chim.2005,50 (7-8): 627-631 is d...

Claims

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Application Information

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IPC IPC(8): C07C69/734C07C67/08
Inventor 刘启发王荣张业林
Owner ANHUI SHENGNUOBEI CHEM TECH
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