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Synthetic method of 1,1,1,4,4,4-hexafluoro-2-butene

A synthesis method and technology of hexachlorobutadiene are applied in the directions of dehalogenation preparation, organic chemistry, etc., which can solve the problems of high raw material price, complicated process, difficult to obtain, etc., and achieve the effects of easy availability of raw materials, simple process and low cost.

Active Publication Date: 2015-07-15
JUHUA GROUP TECH CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation of 1,1,1,4,4,4-hexafluoro-2-butene by using hexafluoropropylene and chloroform as raw materials and carbon tetrachloride and ethylene as raw materials has the disadvantages of long steps and complicated processes.
Synthesis of 1,1,1,4,4,4-hexafluoro-2-butene from 1,1,1-trifluoro-2-bromo-2-chloroethane has the disadvantages of high raw material price and difficult availability

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 30g (0.10mol) antimony pentachloride and 400g (20mol) hydrogen fluoride to a 1.0L autoclave, stir, and then add 260.8g (1.0mol) hexachlorodibutene at a rate of 2.0g / min with a metering pump . After the addition of hexachlorodibutene, react at 40°C for 1h, then raise the temperature to 80°C for 6h, cool, add the reaction solution to 1200g of ice water, add 300g of dichloromethane for extraction, separate layers, and use the organic layer 200g of saturated sodium bicarbonate solution was washed and rectified to obtain 202.1g (0.86mol) of 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane with a content of 99.2%, yield 86 %.

[0031]In a 500ml four-necked flask with a condenser tube, add 65g (1.0mol) of zinc powder activated by dilute hydrochloric acid, 180g of N,N-dimethylformamide, pass through the nitrogen to replace the air in the flask, and pass through the condenser tube into industrial water, and the tail gas was collected with a cold trap at -30°C. Stir, heat up to 5...

Embodiment 2

[0033] Add 2.6g (0.01mol) tin tetrachloride and 500g (25mol) hydrogen fluoride to a 1.0L high-pressure reactor, stir, and then add 130.4g (0.5mol) hexachlorodibutyl at a speed of 1.0g / min with a metering pump alkene. After the addition of hexachlorodibutene, react at 50°C for 0.5h, then raise the temperature to 150°C for 3h, cool, add the reaction solution to 2000g of ice water, then add 400g of dichloromethane for extraction, separate layers, and the organic layer Wash with 200g saturated sodium bicarbonate solution and then rectify to obtain 62.5g (0.27mol) of 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane with a content of 99.0%, yield 53.2%.

[0034] In a 250ml four-necked flask with a condenser tube, add 48.8g (0.75mol) of zinc powder and 100g of dimethyl sulfoxide, pass nitrogen to replace the air in the flask, pass industrial water into the condenser tube, and use -30 ℃ cold trap collection. Stir, heat up to 80°C, add dropwise 10g of 1,1,1,4,4,4-hexafluoro-2,3-dichlorobut...

Embodiment 3

[0036] Add 38g (0.20mol) titanium tetrachloride and 160g (8mol) hydrogen fluoride to a 1.0L autoclave, stir, and then add 260.8g (1.0mol) hexachlorodibutene at a rate of 1.0g / min with a metering pump . After the addition of hexachlorodibutene, react at 30°C for 2h, then raise the temperature to 60°C for 8h, cool, add the reaction liquid to 1000g of ice water, then add 200g of dichloromethane for extraction, separate the layers, and use the organic layer 100g of saturated sodium bicarbonate solution was washed and rectified to obtain 155.1g (0.66mol) of 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane with a content of 99.3%, yield 66 %.

[0037] In a 500ml four-necked flask with a condenser tube, add 41g (0.63mol) of zinc powder activated by dilute hydrochloric acid, 80g of N,N-dimethylformamide, pass through nitrogen to replace the air in the flask, and pass through the condenser tube into industrial water, and the tail gas was collected with a cold trap at -30°C. Stir, raise the...

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Abstract

The invention discloses a synthetic method of 1,1,1,4,4,4-hexafluoro-2-butene, and the synthetic method comprises the steps of carrying out a reaction between hexachlorobutadiene and hydrogen fluoride in the presence of a catalyst to generate 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane, and carrying out a reductive dechlorination reaction on the 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane in a solvent by using zinc powder to generate the 1,1,1,4,4,4-hexafluoro-2-butene. According to the synthetic method, the process is simple, the steps are short, the reaction conditions are mild and the product can be obtained through two steps of reaction; and the raw materials are easy to get, the cost is low, and the byproduct hexachlorobutadiene obtained by reducing tetrachloroethylene by carbon tetrachloride at high temperature can be used as a raw material, so that the cost is further reduced.

Description

technical field [0001] The present invention relates to the synthetic method of fluoroalkene, be specifically related to a kind of 1,1,1,4,4,4-hexafluoro-2-butene (CF 3 CH=CHCF 3 ) synthesis method. Background technique [0002] 1,1,1,4,4,4-hexafluoro-2-butene can be divided into cis and trans isomers, usually a colorless and odorless gas. Hexafluoro-2-butene is considered to be one of the ideal substitutes for blowing agent HCFC-141b, and can be used as a new blowing agent, refrigerant and fire extinguishing agent. The foaming agent product is environmentally friendly, has remarkable heat insulation properties, is non-flammable, does not deplete ozone, can replace other liquid foaming agents with low conversion costs, and has broad application prospects. [0003] 1,1,1,4,4,4-hexafluoro-2-butene mainly has the following synthesis methods. [0004] Honeywell Company (patent publication number: US2011288349A1) synthesized 1,1,1,4,4,4-hexafluoro-2-butene by using hexafluoro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C21/18C07C17/23
Inventor 王树华叶立峰周强
Owner JUHUA GROUP TECH CENT
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