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A kind of synthetic method of acryloyl chloride

A synthesis method and technology of acryloyl chloride, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate, etc., can solve the problems of low product purity, high raw material price, poor availability, etc., and achieve reaction yield high effect

Inactive Publication Date: 2016-03-30
HUBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Using phosphorus trichloride as the main raw material to prepare acryloyl chloride, the product yield is only about 66%, and the purity is not high
Since the boiling point of phosphorus trichloride is 76°C, which is close to the boiling point of the product acryloyl chloride, the separation method is difficult and complicated; using thionyl chloride as the chlorination agent to prepare acryloyl chloride, the yield of the target product after separation and purification is 63.0 ~79.9%, the yield is low, and there are HCl and SO in the reaction process 2 Such poisonous irritating gas produces, and reaction time is also too long; Because the reaction of benzoyl chloride and acrylic acid is a reversible reaction, productive rate is lower; Prepare acryloyl chloride as raw material with β-chloropropionyl chloride, and target product yield can be Up to 80%, compared with the aforementioned method, the yield is significantly higher, but technically there are also disadvantages such as difficult separation, low product purity, high raw material price, and poor availability; what European patent EP387116 reported is based on acrylic acid and trichlorotoluene. Acryloyl chloride is prepared from raw materials, and its by-product benzoyl chloride is an important fine chemical raw material, but trichlorotoluene has poor raw material availability, low product purity, and low yield (70%); in Japanese Patent P2003-277319A, synthesis uses Phosgene is a banned chemical raw material. In addition, another raw material, diphosgene, is very unstable and easily decomposed into phosgene, which poses a safety hazard during the experimental operation.

Method used

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  • A kind of synthetic method of acryloyl chloride
  • A kind of synthetic method of acryloyl chloride
  • A kind of synthetic method of acryloyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 3.60g of acrylic acid (0.05mol), 0.11g of dimethyl sulfoxide, and 0.09g of cuprous chloride to a 25mL reactor equipped with a thermometer, a condenser, and a constant pressure dropping funnel, and mix well; use 7.58g of triphosgene with Dissolve 20mL of chloroform to form a chloroform solution of triphosgene, then transfer it to the above-mentioned constant pressure dropping funnel, add the chloroform solution of triphosgene to the reactor dropwise at 70°C, and keep the reaction for 9 hours after the addition is completed. Cooling and distillation under reduced pressure gave 4.30 g of the product acryloyl chloride, with a yield of 95.0%. The product was analyzed by gas chromatography, and the purity was 98.9%.

Embodiment 2

[0024] Add 3.60 g of acrylic acid (0.05 mol), 0.056 g of N,N'-dimethylformamide, 0.09 g of tin tetrachloride and hydroquinone into a 25 mL reactor equipped with a thermometer, condenser and constant pressure dropping funnel (mass ratio 1:1) mixture, mix well; 7.58g triphosgene is dissolved with 20mL ether to form the ether solution of triphosgene, then it is transferred to the above-mentioned constant pressure dropping funnel, at 70 ℃, the triphosgene The diethyl ether solution of gas was added dropwise to the reactor, and the reaction was kept for 24 hours after the dropwise addition was completed. Cooling and distillation under reduced pressure gave 4.35 g of the product acryloyl chloride, with a yield of 96.1%. The product was analyzed by gas chromatography, and the purity was 99.2%.

Embodiment 3

[0026] Add 72.06g of acrylic acid (1mol), 0.44g of triethylamine, and 0.09g of cuprous chloride to a 1000mL reactor equipped with a thermometer, a condenser, and a constant pressure dropping funnel, and mix well; mix 148.38g of triphosgene with 800mL of tetrahydrofuran Dissolve to form a tetrahydrofuran solution of triphosgene, and then transfer it to the above-mentioned constant pressure dropping funnel. At 70°C, add the tetrahydrofuran solution of triphosgene dropwise into the reactor, and keep warm for 24 hours after the dropwise addition. Cooling and distillation under reduced pressure yielded 87.60 g of the product acryloyl chloride with a yield of 96.8%. The product was analyzed by gas chromatography, and the purity was 98.0%.

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Abstract

The invention discloses a synthetic method of acryloyl chloride. Triphosgene reacts with acrylic acid to produce the acryloyl chloride. The triphosgene and the acrylic acid are used as raw materials, and one of dichloromethane, chloroform, acetone, ethyl ether, benzene, tetrahydrofuran, n-hexane, cyclohexane and the like is used as an organic solvent; one of hydroquinone, resorcinol, cupper chloride and a mixture of tin tetrachloride and hydroquinone is used as an acrylic acid polymerization inhibitor, the triphosgene is firstly dissolved in the organic solvent, then the organic solvent is added to a reactor containing the polymerization inhibitor, an organic nitrogen compound and the acrylic acid for reaction at the temperature of 70 DEG C for 9-38 h, and the high-yield acryloyl chloride can be obtained. The reaction is high in conversion rate which is about 99%, no other by-product is produced, the reaction condition is mild, and materials can be directly fed for the next reaction without separation.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing acryloyl chloride, in particular to a method for preparing acryloyl chloride by using triphosgene as a main raw material. Background technique [0002] Acryloyl chloride is a chlorine-containing acrylic acid derivative, which can be used as a multi-purpose organic chemical intermediate. Utilizing the active chemical properties of acryloyl chloride, many kinds of chemical reactions can be realized, and then corresponding chemicals can be prepared. Especially in the acrylic acid industry, acryloyl chloride can be used to prepare special acrylates, including special acrylate products with high technical difficulty. Another important application of acryloyl chloride is to prepare acrylamide, such as N-acetylacrylamide, from acryloyl chloride as a raw material component. In terms of pharmaceutical chemicals, because it contains acyl chloride groups,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C57/66C07C51/60
CPCC07C51/60C07C51/64C07C57/66
Inventor 王薇孙丹周宝晗胡立新任家强李陵岚
Owner HUBEI UNIV OF TECH