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Preparation method and application of octyl methoxycinnamate

A technology for methoxymeat and p-methoxybenzaldehyde is applied in the field of preparation of p-methoxycinnamate, can solve problems such as high cost and regeneration, and achieves high use efficiency, simple operation process and good catalytic effect. Effect

Inactive Publication Date: 2017-06-13
广州星业科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The precious metal palladium is used as a catalyst in the above technical scheme, and its cost is extremely high, so the problem of catalyst regeneration must be solved in industrial production in order to make it have the prospect of industrialization

Method used

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  • Preparation method and application of octyl methoxycinnamate
  • Preparation method and application of octyl methoxycinnamate
  • Preparation method and application of octyl methoxycinnamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The preparation of embodiment 1 methyl methoxycinnamate

[0032] 1. Stir 136 grams (1mol) of p-methoxybenzaldehyde, 148 grams (2mol) of methyl acetate, 303 grams (3mol) of dipropylamine and 1000g toluene, and control the temperature at 0°C;

[0033] 2. Add 285 g (1.5 mol) of titanium tetrachloride catalyst dropwise for about 30 minutes. After the dropwise addition, raise the temperature to 20°C and react for 5 hours;

[0034] 3. After the reaction was completed, the reaction solution was washed with 5% dilute hydrochloric acid until neutral, washed with water, and the organic phase was dried by adding anhydrous sodium sulfate. After desolventization, 188 grams of methyl p-methoxycinnamate were obtained, with a yield of 98%.

[0035] Synthetic route is as shown in formula (2):

[0036]

Embodiment 2

[0037] The preparation of embodiment 2 ethyl methoxycinnamate

[0038] 1. Stir 136 g (1 mol) of p-methoxybenzaldehyde, 132 g (1.5 mol) of ethyl acetate, 170 g (2 mol) of piperidine and 1000 g of n-hexane, and control the temperature at -5°C;

[0039] 2. Add 95 g (0.5 mol) of titanium tetrachloride catalyst dropwise for about 15 minutes. After the dropwise addition, raise the temperature to 30°C and react for 2 hours;

[0040] 3. After the reaction was completed, the reaction solution was washed with 5% dilute hydrochloric acid to neutrality, washed with water, the organic phase was dried by adding anhydrous sodium sulfate, and 203 grams of ethyl p-methoxycinnamate was obtained after desolventization, with a yield of 99%.

[0041] Synthetic route is as shown in formula (3):

[0042]

Embodiment 3

[0043] The preparation of embodiment 3 p-methoxycinnamic acid isobutyl esters

[0044] 1. Stir 136 g (1 mol) of p-methoxybenzaldehyde, 140 g (1.2 mol) of isobutyl acetate, 158 g (2 mol) of pyridine and 1500 g of xylene, and control the temperature at -10°C;

[0045] 2. Add 152 g (0.8 mol) of titanium tetrachloride catalyst dropwise for about 20 minutes. After the dropwise addition, raise the temperature to 10°C and react for 12 hours;

[0046] 3. After the reaction was completed, the reaction solution was washed with 5% dilute hydrochloric acid to neutrality, washed with water, and the organic phase was dried by adding anhydrous sodium sulfate. After desolventization, 230 g of isobutyl p-methoxycinnamate was obtained, with a yield of 98%.

[0047] Synthetic route is as shown in formula (4):

[0048]

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Abstract

The invention discloses a preparation method of octyl methoxycinnamate (OMC). The preparation method comprises the following steps: firstly, uniformly stirring p-methoxybenzaldehyde, acetate, organic amine substances and a solvent, and controlling the temperature to be from 20 DEG C below zero to 10 DEG C; then dropwise adding a titanium tetrachloride catalyst, and after dropwise addition, rising the temperature to 10 to 40 DEG C, and carrying out reaction for 2 to 16h; after the reaction is completed, washing a reaction solution with dilute acid until being neutral, washing with water, drying an organic phase with anhydrous sodium sulfate, and carrying out solvent removal to obtain the octyl methoxycinnamate, wherein the yield reaches 98 percent or above. The preparation method has the characteristics of simpleness, convenience, easiness in control and industrial production, small environmental pollution, low energy consumption, capability of recycling materials, high purity and the like. The prepared octyl methoxycinnamate has the advantages of being colorless and transparent, high purity and the like and can be applied to the field of sun-screening cosmetics, chemical industry for daily supplies, plastics, rubber, coatings and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method and application of p-methoxycinnamate. Background technique [0002] p-methoxycinnamate is currently the most commonly used sunscreen agent in the world. It has excellent ultraviolet light absorption range, high absorption rate, low skin irritation, good safety, and good solubility to oily raw materials. It is a kind of very ideal sunscreen agent, which has good application in the fields of daily chemical industry, plastic, rubber and paint. At present, it is mainly prepared by the following methods: [0003] 1. Aldol condensation reaction preparation: For example, it is disclosed in CN1218794, CN1170401 and CN102627559, and is prepared by aldol condensation reaction under the action of sodium alkoxide with p-methoxybenzaldehyde and methyl acetate or isooctyl acetate as raw materials p-Methoxycinnamate. However, the above-mentioned pr...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/734
CPCC07C67/343C07C69/734
Inventor 李方孟巨光
Owner 广州星业科技股份有限公司
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