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Acetoxy acetyl chloride chemical synthesizing method

A technology of acetoxyacetyl and acetoxyacetic acid, applied in the field of chemical synthesis of acetoxyacetyl chloride, can solve the problems of high sealing requirements of reaction equipment, low product yield and purity, and high production cost, and achieves a large implementation Value and social and economic benefits, low production cost, and low three wastes

Inactive Publication Date: 2007-04-25
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0004] The tail gas of the thionyl chloride process contains a large amount of asphyxiating sulfur dioxide. The emission of sulfur dioxide is one of the six indicators strictly controlled by the national environmental protection on the atmosphere. There is a big problem in market sales, and because it is an aqueous solution after being absorbed by alkali, it must be concentrated to obtain a mixture of sodium sulfite and sodium chloride, the production process consumes a lot of energy and the production cost is high
In addition, the transportation and use of thionyl chloride are strictly controlled, and the requirements for the tightness of the reaction equipment are high, and the investment is also large. At the same time, there are still problems such as low product yield and purity in the original process that need to be solved.

Method used

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  • Acetoxy acetyl chloride chemical synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The amount ratio of feed material is acetoxyacetic acid: two (trichloromethyl) carbonate: organic amine catalyst is 1: 0.34: 0.01, and catalyzer is tetramethylguanidine, and organic solvent is toluene, and its consumption is the quality of acetoxyacetic acid 2 times.

[0018] In a 100mL three-necked flask equipped with a thermometer, a reflux condenser and mechanical stirring, add 11.8g (100mmol) of acetoxyacetic acid, 10.1g (34mmol) of bis(trichloromethyl)carbonate, 28ml of toluene and tetramethylguanidine 0.1 g (1 mmol). After the addition was completed, the temperature was raised to 40°C and reacted at 40°C for 7 hours. After the reaction was completed, the solvent was evaporated under normal pressure, and the vacuum degree was 1.6kpa. 90.3%, purity 98.5%. 1 H NMR (CDCl 3 )δ: 4.9(s, 2H), 2.2(s, 3H).

Embodiment 2

[0020] The ratio of the amount of feed material to acetoxyacetic acid: bis(trichloromethyl)carbonate: organic amine catalyst is 1: 0.7: 0.01, and the feeding amount of acetoxyacetic acid is 11.8g (100mmol), and bis(trichloromethyl) Carbonate charging capacity is 20.5g (70mmol), and catalyzer is 1,3-dimethyl-2-imidazolidinone, and its consumption is 0.1g (1mmol), and organic solvent is toluene, and its consumption is the quality of acetoxyacetic acid 2 times.

[0021] The reaction temperature was 45-50° C., and other operations were the same as in Example 1 to obtain 12.5 g of acetoxyacetyl chloride with a product yield of 91.5% and a purity of 99.0%. 1 H NMR (CDCl 3 )δ: 4.9(s, 2H), 2.2(s, 3H).

Embodiment 3

[0023] The ratio of the amount of feed material to acetoxyacetic acid: bis (trichloromethyl) carbonate: organic amine catalyst is 1: 1: 0.02, and the feeding amount of acetoxyacetic acid is 11.8g (100mmol), bis (trichloromethyl) The charging amount of carbonate is 29.7g (100mmol), the catalyst is pyridine, and its consumption is 0.2g (2mmol), and the organic solvent is tetrahydrofuran, and its consumption is 2 times of the mass of acetoxyacetic acid.

[0024] The reaction temperature was 60-65° C., and other operations were the same as in Example 1 to obtain 11.8 g of acetoxyacetyl chloride with a product yield of 86.6% and a purity of 99.0%. 1 H NMR (CDCl 3 )δ: 4.9(s, 2H), 2.2(s, 3H).

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Abstract

The invention discloses a chemical synthesizing method of ethoxy acetyl chloride, which is characterized by the following: adopting ethoxy acetate and di (trichloromethyl) carbonate as raw material; reacting in the organic solvent under 40-100 deg.c for 1-10h catalyzed by organic amine; obtaining the product.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of acetoxyacetyl chloride. (2) Background technology [0002] Acetoxyacetyl chloride is an important organic intermediate used in the synthesis of the antineoplastic drug paclitaxel and the herbicide mefenacet. [0003] Before the present invention was given, the chemical synthesis method of acetoxyacetyl chloride in the prior art was mostly prepared by chlorination of acetoxyacetic acid and thionyl chloride or oxalyl chloride. As proposed by Pesticide 1994, 33(6), use 76g (1mol) glycolic acid to react with 141g (1.7mol) acetyl chloride at a temperature of 20 to 30°C to prepare acetoxyacetic acid, then add thionyl chloride 174g (1.42 mol) heated to boiling, reacted for 3h and then distilled under reduced pressure. [0004] The tail gas of the thionyl chloride process contains a large amount of asphyxiating sulfur dioxide. The emission of sulfur dioxide is one of the six indicators strictly cont...

Claims

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Application Information

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IPC IPC(8): C07C51/60C07C59/21
Inventor 陈志卫苏为科徐之俊张松乔汤秋明
Owner ZHEJIANG UNIV OF TECH
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