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Preparation method 1,1,1,4,4,4-hexafluoro-2-butene

A technology of hexachlorobutadiene and butene, which is applied in the field of preparation of fluorine-containing olefins, can solve problems such as high pressure, difficulty in recycling amide solvents, and many wastes, and achieve the effects of large operating flexibility, easy industrialization, and reduction of wastes

Active Publication Date: 2017-07-21
ZHEJIANG QUHUA FLUOR CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage is that the reaction is a liquid phase reaction, the pressure is high, the ratio of cis and trans products is not easy to control, the total yield is not high, it is difficult to reuse the amide solvent, and there are many wastes
This invention is difficult to control the degree of hydrogenation, and some alkane by-products will be generated
[0009] Hexachlorobutadiene (CCl 2 =CClCCl=CCl 2 HCBD, referred to as HCBD) is an ozone-depleting substance (ODS) substance. At present, there is no effective way for resource utilization. It is the main by-product produced in the production process of polychlorinated hydrocarbons such as tetrachlorethylene and trichlorethylene. It is toxic The production and use of chlorine-containing organic pollutants are restricted by the Montreal Protocol. According to incomplete statistics, the production of HCBD in my country is tens of thousands of tons per year. At the same time, HCBD will generate highly toxic dioxins when incomplete combustion secondary pollutants
The disadvantage is that the use of liquid phase dechlorination produces a large amount of chlorine-containing wastewater, and there are many wastes
The present invention uses hexachlorobutadiene and hydrofluoric acid as raw materials to synthesize 1,1,1,4,4,4-hexafluoro-2-butene in one step, and the catalyst is preferably AlF 3 , SbF 3 and SbF 5 , the disadvantage is that the reaction temperature is high, and more by-products will be formed

Method used

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  • Preparation method 1,1,1,4,4,4-hexafluoro-2-butene

Examples

Experimental program
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Effect test

Embodiment 1

[0055] 120ml Cr 2 o 3 / Zn / Mg / Ga catalyst (the loading of Zn is 3wt%, the loading of Mg is 1wt%, and the loading of Ga is 0.1wt%) is loaded into the first reactor, and 200ml Al 2 o 3 / ZnCl 2 Catalyst (ZnCl 2 The load is 3wt%) into the second reactor, 200mlPd / BaSO 4 Catalyst (0.1 wt% Pd loading) was charged into the third reactor. Heat the first reactor to 150°C for drying, continue to heat up to 350°C for 4 hours under the protection of nitrogen flow rate of 2.5L / min, then cool down to 300°C, and feed HF at a flow rate of 50g / h, the heat release is obvious, and the hot spot goes away After completion, the temperature was raised to 350°C and HF was fed into the flow rate of 100g / h to continue fluorination for 40 hours; the second reactor was heated to 350°C, the nitrogen flow rate was 2.5L / min, and solidified for 4 hours; the third reactor was passed into H 2 , the flow rate is 0.4L / min, the temperature is raised to 250°C, and it is stable for 2 hours. Catalyst treatment ...

Embodiment 2

[0060] 120ml Cr 2 o 3 / Zn / Mg / Ga catalyst (the loading of Zn is 5wt%, the loading of Mg is 3wt%, and the loading of Ga is 0.5wt%) is loaded into the first reactor, and 200ml Al 2 o 3 / ZnCl 2 Catalyst (ZnCl 2 The load is 10wt%) into the second reactor, 200mlPd / BaSO 4 Catalyst (0.2 wt% Pd loading) was charged to the third reactor. The catalyst treatment methods of the three reactors are the same as in Example 1.

[0061] Then start the feeding reaction, the molar ratio of HF and HCBD is 15:1, the bed temperature of the first reactor is 230°C, and the space velocity is 500h -1 , the mixture at the outlet of the first reactor is analyzed by gas chromatography for organic composition; the 1,1,1,4,4,4-hexafluoro-2-chloro-2-butene obtained by the hydrogen fluoride separator enters the second reactor and is controlled Bed temperature 300°C, space velocity 200h -1 , the mixture at the outlet of the second reactor is analyzed by gas chromatography for organic composition; the sec...

Embodiment 3

[0065] 120ml Cr 2 o 3 / Zn / Mg / Ga catalyst (the loading of Zn is 5wt%, the loading of Mg is 3wt%, and the loading of Ga is 1wt%) is loaded into the first reactor, and 200ml Al 2 o 3 / ZnCl 2 Catalyst (ZnCl 2 The load is 10wt%) into the second reactor, 200mlPd / BaSO 4 Catalyst (0.2 wt% Pd loading) was charged to the third reactor. The catalyst treatment methods of the three reactors are the same as in Example 1.

[0066] Then start the feeding reaction, the molar ratio of HF and HCBD is 15:1, the bed temperature of the first reactor is 260°C, and the space velocity is 500h -1 , the mixture at the outlet of the first reactor is analyzed by gas chromatography for organic composition; the 1,1,1,4,4,4-hexafluoro-2-chloro-2-butene obtained by the hydrogen fluoride separator enters the second reactor and is controlled Bed temperature 350°C, space velocity 400h -1 , the mixture at the outlet of the second reactor is analyzed by gas chromatography for organic composition; the secon...

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Abstract

The invention discloses a preparation method of 1,1,1,4,4,4-hexafluoro-2-butene. According to the preparation method, raw materials hexachlorobutadiene and hydrogen fluoride are subjected to preheating, and are delivered into a first reactor; reaction is carried out in the presence of zinc, magnesium, gallium-loaded chromic oxide catalyst so as to obtain a mixture containing 1,1,1,4,4,4-hexafluoro-2-chloro-2-butene; separation is carried out, and obtained 1,1,1,4,4,4-hexafluoro-2-chloro-2-butene is delivered into a second reactor; reaction is carried out in the presence of zinc chloride-loaded aluminium oxide catalyst so as to obtain a mixture containing hexafluoro-2-butyne; separation is carried out, and obtained hexafluoro-2-butyne and hydrogen are delivered into a third reactor; reaction is carried out in the presence of Pd / BaSO4 catalyst so as to obtain a mixture containing 1,1,1,4,4,4-hexafluoro-2-butene, and 1,1,1,4,4,4-hexafluoro-2-butene is obtained via separation. The preparation method is simple; the raw materials are easily available; cost is low; and yield is high.

Description

technical field [0001] The invention relates to a preparation method of fluorine-containing olefin, in particular to a preparation method of 1,1,1,4,4,4-hexafluoro-2-butene. Background technique [0002] 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz), Ozone Depletion Potential (ODP) is zero, Greenhouse Effect Potential (GWP) is only 9.4, under ultraviolet irradiation Photolysis reaction is easy to occur under the environment, and the atmospheric life is short. HFO-1336mzz has two isomers, cis (Z type) and trans (E type), E type has a boiling point of 8°C and a liquid phase density of 1.413g / ml, Z type has a boiling point of 34°C and a liquid phase density of 1.356g / ml. Among them, Z-HFO-1336mzz is considered to be one of the ideal substitutes for foaming HCFC-141b, which has good market prospects and economic benefits; E-HFO-1336mzz is also one of the substitutes for refrigerants, and 1-chloro-3 , 3,3-trifluoropropene or ethylene oxide can form azeotrope, which can be use...

Claims

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Application Information

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IPC IPC(8): C07C17/354C07C21/18
CPCC07C17/00C07C17/25C07C17/354C07C21/18C07C21/22
Inventor 洪江永杨波王爱国张彦余国军赵阳欧阳豪
Owner ZHEJIANG QUHUA FLUOR CHEM
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