Method for synthesizing methyl oleate

A technology for methyl oleate and a synthesis method, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of long reaction time, high production cost and high reaction temperature, and achieves reduction of raw material consumption. , the production cost reduction, the effect of mild reaction conditions

Inactive Publication Date: 2013-09-25
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the reaction time of this method is shorter than that of the traditional preparation method, the reaction temperature is higher, the reaction time is longer, the preparation cost of the catalyst is higher and the dosage is larger, the

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] a. Preparation of solid acid catalyst

[0017] Weigh SiO 2 Stir and mix 10.0g of solid with 40.0ml of anhydrous ether, then slowly add 5.0ml of sulfuric acid with a concentration of 98% dropwise, stirring is required during the dropwise addition, ventilate it after the dropwise addition, let the ether volatilize, and then place it in an oven for drying. Set at 135°C, drying time is 4h, the light brown fine powder obtained is H 2 SO 4 / SiO 2 Immobilized catalyst, ready for use.

[0018] b. Esterification reaction

[0019] Mix 2.00ml of oleic acid with 0.77ml of methanol and 0.044g of the above prepared H 2 SO 4 / SiO 2 The solid-supported catalyst was stirred and mixed, and the esterification reaction was carried out under stirring. The temperature of the reaction oil bath was 50° C., and the reaction time was 3.0 hours.

[0020] c. to purify

[0021] Catalyst is filtered out in the reaction liquid of above-mentioned esterification, and filtrate is purified throu...

Embodiment 2

[0023] a. The solid acid catalyst is the catalyst recovered by filtration in the c step of Example 1, and the recovered catalyst is dried for use.

[0024] b. Esterification reaction

[0025] Mix 2.00ml of oleic acid with 0.52ml of methanol and 0.044g of the above recovered dried H 2 SO 4 / SiO 2 The solid-supported catalyst was stirred and mixed, and the esterification reaction was carried out under stirring. The temperature of the reaction oil bath was 100° C., and the reaction time was 2.0 hours.

[0026] c. Purification

[0027] The catalyst was filtered out from the above-mentioned esterified reaction solution, and the filtrate was purified by silica gel column chromatography to obtain 1.493 g of methyl oleate, a colorless transparent oily liquid, with a yield of 79.6%.

Embodiment 3

[0029] A. the preparation of solid acid catalyst is with embodiment 1

[0030] b. Esterification reaction

[0031] Mix 2.00ml of oleic acid with 0.77ml of methanol and 0.044g of the above prepared H 2 SO 4 / SiO 2 The solid-supported catalyst was stirred and mixed, and the esterification reaction was carried out under stirring. The temperature of the reaction oil bath was 90° C., and the reaction time was 3.0 hours.

[0032] c. to purify

[0033] The catalyst was filtered out from the above-mentioned esterified reaction solution, and the filtrate was purified by silica gel column chromatography to obtain 1.722 g of methyl oleate, a colorless transparent oily liquid, with a yield of 91.8%.

[0034] The resulting product methyl oleate is detected and analyzed by nuclear magnetic spectrum, and its structure can be confirmed as the target product. The nuclear magnetic spectrum measured by the methyl oleate sample: 1 H-NMR (500MHz, CDCl 3 ):δ(ppm) 5.35(m, 2H), 3.68(q, 3H), 2.3...

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PUM

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Abstract

The invention discloses a method for synthesizing methyl oleate. The method is characterized by comprising the following steps: carrying out an esterification reaction between oleic acid and methanol in the presence of an H2SO4/SiO2 immobilized catalyst, filtering the reaction solution, and purifying the filtrate through column chromatography to obtain colorless transparent oily liquid methyl oleate, wherein the molar ratio of oleic acid to methanol is 1: (1.5-5); and the molar ratio of the catalyst to oleic acid is 1: (10-50). Compared with the prior art, the method has the advantages that the method is simple in process, convenient to operate, low in production cost, high in yield and mild in reaction conditions, the consumption of raw materials is further reduced, the yield can be improved to be over 90 percent, and the production cost is obviously reduced; and moreover, the catalyst is simple in after-treatment and slight in pollution and can be recycled, and the method is a methyl oleate synthesizing method which is environment-friendly, economic and high-efficiency and has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing methyl oleate. Background technique [0002] Methyl oleate is a light yellow transparent oily liquid, which is widely used in organic synthesis such as chemical industry, textile and medicine. It is mainly used as an intermediate of surface detergent, emulsifier and stabilizer. Fatty acids serve as raw materials for many oleochemicals. The synthesis of methyl oleate has been studied for a long time. The most typical traditional preparation method is to use oleic acid and methanol as raw materials, use sulfuric acid as a catalyst to heat and reflux, and use sodium methoxide to neutralize to a pH of 8~ 9. Wash with water until neutral, then dry with anhydrous calcium chloride, and filter. (Xu Kexun. Handbook of Fine Organic Chemical Raw Materials and Intermediates. Beijing: Chemical Industry Press 1998, 4:1~350). The disadvantage of t...

Claims

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Application Information

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IPC IPC(8): C07C69/58C07C67/08
CPCY02P20/584
Inventor 张剑波吴长坤戴荣婷张凤海张凯李云辉骆小胜陈和善
Owner EAST CHINA NORMAL UNIVERSITY
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