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

A synthesis method and technology of butene, applied in the direction of halogen substitution preparation, dehydrohalogenation preparation, organic chemistry, etc., can solve the problems of high price, large pollution, low selectivity, etc., and achieve the effect of high price and low cost

Active Publication Date: 2015-02-25
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example: WO 2009117458 reported the synthesis of HFO-1336 by reacting a chemical amount of copper powder with HCFC-123. The ratio of cis and trans in the product is close to 1:1, which not only has low selectivity but also causes great pollution
[0005] WO 2011119370 reported the catalytic telomerization of trifluoropropene and carbon tetrachloride to synthesize tetrachlorotrifluorobutane, and catalyzed fluorination to synthesize the product 1,1,1,4,4,4-hexafluoro-2-butene, using raw materials Trifluoropropene has not yet been produced on a large scale and is expensive. The sum of the selectivities of cis-HFO-1336 and trans-HFO-1336 in the product is 93%

Method used

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

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Embodiment 1

[0031] (a) Add 1.4 grams of copper chloride and 3.2 grams of 2,2-bipyridine to a 500 mL titanium alloy belt stirred autoclave, dissolve them in 20 mL of methanol, replace the air in the kettle with nitrogen, and inject 312 grams of R123 and 63 g CH 2 =CHCl, reaction temperature 120°C, reaction pressure 1.2MPa, reaction time 10 hours, remove R123 and methanol from the crude product after reaction by distillation at atmospheric pressure, recycle R123 and methanol, continue vacuum distillation to collect CF 3 CHClCH 2 CHCl 2 , conversion rate 91.3%, selectivity 87.6%.

[0032] (b) Add 150 g of CF to a 500 mL quartz photochemical reactor 3 CHClCH 2 CHCl 2 Dissolve in 300mL carbon tetrachloride solution, slowly pass in about 140 grams of chlorine gas under stirring, react at 0°C for 24 hours, and continue to collect the product CF after vacuum distillation to separate carbon tetrachloride 3 CHClCH 2 CCl 3 , conversion rate 90.5%, selectivity 78.7%.

[0033] (c) In a nickel...

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Abstract

The invention provides a method for synthesizing trans-1, 1, 1, 4, 4, 4-hexafluoro-2-butene by three steps by taking 1, 1, 1-triflluoro-2, 2-dichloroethane and chloroethylene CH2=CX2 as raw materials. The method comprises the following steps: (a) in the presence of a telomerization catalyst and a catalytic addictive, carrying out reactive synthesis on 1, 1, 1-triflluoro-2, 2-dichloroethane and CH2=CX2 to obtain CF3CHClCH2CClX2; (b) carrying out photochlorination on CF3CHClCH2CClX2 to synthesize CF3CHClCH2CCl3; and (c) in the presence of a fluorination catalyst, carrying out gas phase fluorination on CF3CHClCH2CCl3 to synthesize trans-1, 1, 1, 4, 4, 4-hexafluoro-2-butene, wherein CH2=CX2 is ethylene, chloroethylene and 1, 1-dichloroethylene. The method provided by the invention has the characteristics of high trans-selectivity and low price of raw materials.

Description

technical field [0001] The invention relates to a method for synthesizing hydrofluoroolefins, in particular to a method for synthesizing trans-1,1,1,4,4,4-hexafluoro-2-butene. Background technique [0002] Due to the destruction of the ozone layer by the first and second generation blowing agents (fluorotrichloromethane CFC-11, fluorodichloroethane HCFC-141b, etc.), the use of the third generation blowing agents (1,1, 1,3,3-pentafluoropropane (HFC-245fa, etc.) will have a strong greenhouse effect. With the increasing impact of global warming on the earth's ecology, it is urgent to find green and environmentally friendly blowing agents. [0003] As a hydrofluoroolefin (HFO) substance, the ozone depletion potential (ODP) of cis-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336) is zero, and the greenhouse effect potential The value (GWP) is extremely low, and has little impact on the environment. Because its performance is similar to that of previous generations of blowing agents, i...

Claims

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Application Information

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IPC IPC(8): C07C21/18C07C17/25C07C17/20
CPCC07C17/20C07C17/25C07C21/18
Inventor 吕剑赵波毛伟王博曾纪珺张伟郝志军唐晓博马辉李凤仙
Owner XIAN MODERN CHEM RES INST
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