Method for preparing 2-methyl allyl alcohol by esterification and hydrolysis

A technology of methallyl alcohol and methallyl chloride, applied in chemical instruments and methods, preparation of oxygenated compounds, preparation of organic compounds, etc., can solve the problem of low concentration of lye, many side reactions of etherification, etc. The problem of high reaction temperature can reduce the energy consumption and material consumption of separation, improve the product yield, and achieve the effect of high product selectivity.

Active Publication Date: 2013-08-14
NANJING UNIV OF TECH
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  • Abstract
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Problems solved by technology

The disadvantage of this method is that the raw material source of 2-methallyl aldehyde is limited, and the reaction pressure is high, and the selectivity of 2-methallyl alcohol is low
This method also has limited sources of raw materials, high reaction temperature, and high requirements for equipment
[0007] In summary, the route of synthesizing 2-methallyl alcohol with 2-methallyl chloride as raw material is the most competitive, but there are many side reactions of etherification, low lye concentration, Disadvantages such as complex alkali addition method

Method used

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  • Method for preparing 2-methyl allyl alcohol by esterification and hydrolysis
  • Method for preparing 2-methyl allyl alcohol by esterification and hydrolysis

Examples

Experimental program
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Effect test

Embodiment 1

[0035]In a Hastelloy autoclave, 57g of 2-methallyl chloride, 170g of water, 214g of sodium formate and 11.4g of benzyltriethylammonium chloride were added, the reaction temperature was controlled at 60°C, and the esterification reaction was carried out for 15 hours. The reaction solution was left to stand and separated to obtain 58.5 g of an organic phase and 393.9 g of an aqueous phase. Through gas chromatography analysis, in the organic phase, the mass fraction of 2-methallyl chloride is 1.2%, the mass fraction of 2-methallyl formate is 81.4%, and the mass fraction of 2-methallyl alcohol is 17.2%. Add the organic phase to a three-necked flask, add 299.6g of 40% sodium bicarbonate solution, and hydrolyze at 80°C for 0.5h. After the hydrolysis was completed, the reaction solution was allowed to stand and separate into layers to obtain 44.8 g of an organic phase and 313.3 g of an aqueous phase. Through gas chromatography analysis, the mass fraction of 2-methallyl chloride in ...

Embodiment 2

[0037] In a Hastelloy autoclave, 57g of 2-methallyl chloride, 113.3g of water, 96.9g of potassium valerate and 11.4g of polyethylene glycol were added, the reaction temperature was controlled at 120°C, and the esterification reaction was carried out for 8 hours. The reaction solution was left to stand and separated to obtain 87.7 g of an organic phase and 190.9 g of an aqueous phase. Through gas chromatography analysis, in the organic phase, the mass fraction of 2-methallyl chloride is 1.3%, the mass fraction of 2-methallyl valerate is 81%, and the mass fraction of 2-methallyl alcohol is 16.6%. Add the organic phase to a three-necked flask, add 335.6g of potassium carbonate solution with a mass fraction of 30%, and hydrolyze at 50°C for 1 hour. After the hydrolysis was completed, the reaction solution was allowed to stand and separate into layers to obtain 44.8 g of an organic phase and 378.5 g of an aqueous phase. Through gas chromatography analysis, the mass fraction of 2-...

Embodiment 3

[0039] In a Hastelloy autoclave, 57g of 2-methallyl chloride, 45.3g of water, 60.4g of sodium propionate and 0.29g of tetrabutylammonium chloride were added, the reaction temperature was controlled at 250°C, and the esterification reaction was carried out for 0.5h. The reaction solution was left to stand and separated to obtain 70.9 g of an organic phase and 92.1 g of an aqueous phase. Through gas chromatography analysis, in the organic phase, the mass fraction of 2-methallyl chloride is 1.4%, the mass fraction of 2-methallyl propionate is 81.7%, and the mass fraction of 2-methallyl alcohol is 16.7%. Add the organic phase to a three-necked flask, add 108.5 g of 35% sodium bicarbonate solution, and hydrolyze at 10°C for 4 hours. After the hydrolysis was completed, the reaction solution was left to stand and separated to obtain 45 g of an organic phase and 134.4 g of an aqueous phase. Through gas chromatography analysis, the mass fraction of 2-methallyl chloride in the organic...

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Abstract

The invention belongs to the field of chemical industry, and discloses a method for preparing 2-methyl allyl alcohol by esterification and hydrolysis. The method comprises the following steps of: first, performing esterification reaction of 2-methyl allyl chloride and carboxylate; and then, kalifying for hydrolysis reaction to synthesize 2-methyl allyl alcohol. The synthesizing steps are as follows: (1) esterification reaction: under the effect of a phase transfer catalyst, adding carboxylate, water and 2-methyl allyl chloride into a high pressure kettle for esterification reaction; after esterification reaction, cooling, standing and layering the reaction liquor to obtain an organic layer and a water layer, wherein the organic layer is a mixture which takes 2-methyl allyl carboxylate as a main product; (2) hydrolysis reaction: adding alkali liquor to the organic layer obtained in the esterification reaction stage for hydrolysis reaction; cooling, standing and layering the mixed liquor obtained by hydrolysis to obtain an organic layer and a water layer, wherein the organic layer is a target product, namely 2-methyl allyl alcohol. The method is high in material conversion ratio and product selectivity, the product yield is improved, and the separation energy consumption and material consumption are reduced.

Description

technical field [0001] The invention belongs to the field of chemical industry, and relates to a method for preparing 2-methallyl alcohol by two-step method of esterification and hydrolysis. Specifically, the esterification reaction of 2-methallyl chloride and carboxylate is carried out first, and then alkali is added. A method for synthesizing 2-methallyl alcohol by hydrolysis reaction. Background technique [0002] 2-Methallyl alcohol, also known as isobutenol, is an unsaturated alcohol, a colorless flammable liquid with a pungent odor. As an important intermediate, it is used in the synthesis of polymer monomers, surfactants, fragrances, etc. Its preparation method is mainly divided into hydrolysis method and 2-methacryl aldehyde reduction method, and there are also other methods such as pyran derivative decomposition method and esterification method. [0003] Alkaline hydrolysis is a common method for preparing unsaturated alcohols. U.S. Patent US2072016 reports a meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/03C07C27/02
Inventor 崔咪芬汤吉海徐月婵乔旭陈献费兆阳
Owner NANJING UNIV OF TECH
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