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The synthetic method of allyl glycidyl ether

A technology of allyl glycidyl ether and a synthesis method, applied in directions such as organic chemistry, can solve the problems of high consumption of raw materials, cumbersome process and high product cost, and achieve the advantages of improving product yield, concise process and reducing product cost. Effect

Active Publication Date: 2015-08-12
湖北恒鑫化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The disclosed technology for the synthesis of allyl glycidyl ether shows that the synthesis of allyl glycidyl ether by phase transfer catalysis and sodium alkoxide method obviously has the disadvantages of too many reaction product components, difficulty in separation and purification, high raw material consumption, and high product cost.
[0005] The disclosed technology for the synthesis of allyl glycidyl ether shows that there are deficiencies in the synthesis of allyl glycidyl ether by the ring-opening and ring-closing two-step method: the first is that the catalyst selectivity is poor, resulting in a product yield lower than 80%; The reaction uses 32% to 45% sodium hydroxide aqueous solution to react with the intermediate, and there is a large amount of solid sodium chloride in the closed-loop reaction product, which must be filtered, resulting in cumbersome process
These deficiencies increase the cost of the product

Method used

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  • The synthetic method of allyl glycidyl ether
  • The synthetic method of allyl glycidyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Put 174.2 grams (3mol) of allyl alcohol into a three-necked flask, and 0.7 grams of three-way composite catalyst (among them, 0.5 grams of boron trifluoride ether, 0.1 grams of tin tetrachloride, and 0.1 grams of tin dichloride); stir and heat to 75 ℃, keep warm for about 0.5 hours, add 92.5 g (1mol) of epichlorohydrin at a constant speed; after adding, keep warm for 0.6 hours. Unreacted allyl alcohol was recovered by distillation under reduced pressure to obtain a ring-opened product (1-allyloxy-3-chloro-2-propanol); 2.03 mol of allyl alcohol was recovered (directly used as a raw material for the next batch). Cool the ring-opened product to 35°C, and add 200 g of 20% by mass sodium hydroxide aqueous solution to the ring-opened product; after the addition, keep it warm for 1 hour. The temperature was lowered to 30°C and the layers were allowed to stand, and the water layer was separated to obtain 115 grams of a crude product with a purity of 91.02%, and the yield was 91...

Embodiment 2

[0023] Put 174.2 grams (3mol) of allyl alcohol into a three-necked flask, and 0.8 grams of ternary composite catalyst (among them, 0.4 grams of boron trifluoride ether, 0.2 grams of tin tetrachloride, and 0.2 grams of tin dichloride); stir and heat to 90 ℃, maintain around 90 ℃ and add 92.5 g (1 mol) of epichlorohydrin at a constant speed for about 0.5 hours; after the addition, keep warm for 1.3 hours. Unreacted allyl alcohol was recovered by distillation under reduced pressure to obtain a ring-opened product; 2.02 mol of allyl alcohol was recovered (directly used as the raw material of the next batch). The ring-opened product was cooled to 40°C, and 200 g of 22% sodium hydroxide aqueous solution was added to the ring-opened product; after the addition was completed, the reaction was kept for 1 hour. The temperature was lowered to 30°C and the layers were allowed to stand, and the water layer was separated to obtain 114.6 grams of crude product with a purity of 91.12%, and th...

Embodiment 3

[0025] Put 174.2 grams (3mol) of allyl alcohol into a three-necked flask, and 0.6 grams of three-way composite catalyst (among them, 0.45 grams of boron trifluoride ether, 0.1 grams of tin tetrachloride, and 0.05 grams of tin dichloride); stir and heat to 85 ℃, maintain around 85 ℃ and add 92.5 g (1 mol) of epichlorohydrin at a constant speed for about 0.5 hours; after the addition, keep warm for 1.0 hours. Unreacted allyl alcohol was recovered by distillation under reduced pressure to obtain a ring-opened product; 2.03 mol of allyl alcohol was recovered (directly used as the raw material of the next batch). The ring-opened product was cooled to 45° C., and 187 g of 23% sodium hydroxide aqueous solution was added to the ring-opened product; after the addition was completed, the reaction was kept for 1 hour. The temperature was lowered to 30°C and the layers were allowed to stand, and the water layer was separated to obtain 114.3 grams of crude product with a purity of 91.22%, ...

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Abstract

The invention relates to a method for synthesizing allyl glycidyl ether. The method comprises the following steps of: (1) adding an over amount of allyl alcohol into a reactor, further adding a ternary composite catalyst, stirring and heating, preserving the reaction temperature, adding epoxy chloropropane, preserving the temperature and reacting after the addition; (2) distilling and reacting unreacted allyl alcohol so as to obtain a ring-opening product 1, namely, allyloxy-3-chlorine-2-propyl alcohol, recycling the obtained allyl alcohol to be directly used as the raw material for the next batch; (3) cooling down till the ring-closure reaction, adding a sodium hydroxide solution, and carrying out heat preservation reaction after the addition; (4) standing and layering so as to separate the water layer to obtain a crude product, and distilling to obtain the product, namely, the allyl glycidyl ether. The method has the beneficial effects that the process is simple, the production period is short, the operation cost is low, the reaction is stable and easy to control, the raw material consumption is small, and the product cost is lowered. The crude product is detected by using a gas chromatography, the yield is greater than 91% taking the epoxy chloropropane as the reference, and the purity of the product obtained through distillation is greater than 99%.

Description

technical field [0001] The invention relates to a synthesis method of allyl glycidyl ether, which belongs to the technical field of organic synthesis chemistry. Background technique [0002] Allyl glycidyl ether contains unsaturated double bonds and epoxy groups. It is an important polymer monomer and an intermediate in organic synthesis, and is widely used in the field of fine chemicals. The synthetic method of allyl glycidyl ether reported in the literature can be divided into three kinds. The first is a two-step ring-opening and ring-closing method, using allyl alcohol and epichlorohydrin as raw materials, and in the presence of a catalyst, the epoxy ring is opened to obtain the intermediate CH 2 =CHCH 2 OCH 2 CH(OH)CH 2 Cl, and then the intermediate removes HCl and closes the ring under the action of aqueous sodium hydroxide solution to generate the product. The second is the phase transfer catalysis method, using allyl alcohol and epichlorohydrin as raw materials, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/22C07D301/26
Inventor 金炼铁池圣贤陈发德辛小乐
Owner 湖北恒鑫化工有限公司