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Method for preparing trans-1,1,1,4,4,4-hexafluoro-2-butene

A technology for hexafluorobutane and butene, applied in the field of preparing trans-1,1,1,4,4,4-hexafluoro-2-butene, can solve the problem of low conversion rate, low conversion rate, High energy consumption and other issues, to achieve the effect of high catalytic activity

Active Publication Date: 2019-05-07
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent CN 102884030 B has reported that catalyst SbCl 5 In the presence of 1,1,1,3-tetrachloro-4,4,4-trifluorobutane (CF 3 CHClCH 2 CCl 3 ) reaction, a large excess of chlorine gas needs to be introduced at the beginning, and chlorine gas is intermittently introduced every 4 hours during operation to maintain the activity of the catalyst, and the product is 1,1,1,4,4,4-hexafluoro-2-butene And 1,1,1,4,4,4-hexafluoro-2-chlorobutane, under the catalytic conditions, 1,1,1,4,4,4- Hexafluoro-2-butene is chlorinated to generate chlorinated products, which reduces the selectivity of the product, and the selectivity of the specific configuration of 1,1,1,4,4,4-hexafluoro-2-butene is also not In addition, in the gas phase dehydrochlorination of 2-chloro-1,1,1,4,4,4-hexafluorobutane to prepare 1,1,1,4,4,4-hexafluoro-2-butene , using fluorinated chromium oxide as a catalyst, at a temperature of 350°C, the conversion rate of 2-chloro-1,1,1,4,4,4-hexafluorobutane is only 92%, the reaction temperature of this method is high, and the energy consumption Large and low conversion rate
In the first step of this method, the reaction temperature of 1,1,1,4,4,4-hexafluorobutane and halogen is high, the energy consumption is high, and there are many chlorinated by-products, 1,1,1,4,4,4 - low conversion rate of hexafluorobutane (9.1%~44.2%), 1,1,1,4,4,4-hexafluoro-2-halobutane selectivity only (88%~94.5%); the second step 1,1,1,4,4,4-hexafluoro-2-halobutane reacts in alkaline aqueous solution at 100°C, 1,1,1,4,4,4-hexafluoro-2-butane The yield of the cis-trans mixture of alkenes is 78% to 94%, and the reaction temperature is high and the yield is low

Method used

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  • Method for preparing trans-1,1,1,4,4,4-hexafluoro-2-butene

Examples

Experimental program
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Effect test

Embodiment 1

[0018] The liquid phase fluorination reaction to prepare 2-chloro-1,1,1,4,4,4-hexafluorobutane was carried out in a 250mL stainless steel autoclave with stirring. Put 20.4g TaF into the reactor one by one 5 , 20g HF and 6.1g 1,1,1,3-tetrachloro-4,4,4-trifluorobutane, the reaction temperature is 100 ℃, the reaction is 2h. After the reaction, a sample was taken, washed with water to remove the acid, and then analyzed by gas chromatography. The result showed that the conversion rate of 1,1,1,3-tetrachloro-4,4,4-trifluorobutane was 100%, 2-chloro-1,1 The selectivity of 1,4,4,4-hexafluorobutane is 98.5%.

Embodiment 2

[0020] The preparation of E-HFO-1336mzz by alkali removal reaction was carried out in a 250 mL stainless steel autoclave with stirring. Put 100g of 50% KOH aqueous solution, 1.0g of 18-crown-6 and 60g of 2-chloro-1,1,1,4,4,4-hexafluorobutane into the reactor in turn, turn on the stirring, and set the reaction temperature Control at 30°C and react for 30 minutes, slowly drain the low-boiling reaction materials from the gas port of the reactor, collect them in cold hydrazine at -20°C, and analyze the collected materials by gas chromatography. The result shows that 2-chloro-1, The conversion rate of 1,1,4,4,4-hexafluorobutane is 100%, and the selectivity of E-HFO-1336mzz is 99.5%.

Embodiment 3～10

[0022] Examples 3 to 10 Preparation of 2-chloro-1,1,1,4,4,4-hexafluorobutane by liquid-phase fluorination reaction is the same as Example 1, except that the metal fluoride, reaction temperature and reaction are changed Time and response results are shown in Table 1.

[0023] Table 1

[0024]

[0025] The preparation of E-HFO-1336mzz by alkali dereaction is the same as in Example 2, except that the phase transfer catalyst, reaction temperature and reaction time are changed. The reaction results are shown in Table 2.

[0026] Table 2

[0027]

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Abstract

The invention discloses a method for preparing trans-1,1,1,4,4,4-hexafluoro-2-butene. The method comprises the following steps: (1) under the catalysis of a metal fluoride, carrying out liquid-phase fluorination on hydrogen fluoride with 1,1,1,3-tetrachloro-4,4,4-trifluorobutane to prepare 2-chloro-1,1,1,4,4,4-hexafluoro butane, wherein the reaction temperature is 70-110 DEG C, the reaction time is 0.5-10 hours, and the metal fluoride is TaF5, NbF5 or TiF4; and (2) under the action of a phase transfer catalyst, carrying out dehydrochlorination on the 2-chloro-1,1,1,4,4,4-hexafluoro butane in an alkaline solution to prepare the trans-1,1,1,4,4,4-hexafluoro-2-butene, wherein the reaction temperature is 20-40 DEG C, the reaction time is 10-100 minutes, the phase transfer catalyst is a crown ether or a quaternary ammonium salt, and the alkaline solution is a water solution of sodium hydroxide or a water solution of potassium hydroxide. The method is mainly used for preparing the trans-1,1,1,4,4,4-hexafluoro-2-butene.

Description

Technical field [0001] The present invention relates to a method for preparing trans-1,1,1,4,4,4-hexafluoro-2-butene, in particular to 1,1,1,3-tetrachloro-4,4,4 -A method for preparing trans-1,1,1,4,4,4-hexafluoro-2-butene with trifluorobutane as a raw material through liquid phase fluorination and alkali dehydrochlorination. Background technique [0002] As the global warming problem has become increasingly severe in recent years, the third-generation foaming agent is facing elimination or being eliminated in advance. Cis-1,1,1,4,4,4-hexafluoro-2-butene (Z-HFO-1334mzz) as the fourth-generation liquid foaming agent has a good market prospect. Trans-1,1,1,4,4,4-hexafluoro-2-butene (E-HFO-1334mzz), as one of the important intermediates of Z-HFO-1334mzz, has important research and industry Value. [0003] Chinese patent CN 102884030 B reported that the catalyst SbCl 5 In the presence of liquid phase fluorinated 1,1,1,3-tetrachloro-4,4,4-trifluorobutane (CF 3 CHClCH 2 CCl 3 ) The re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/25C07C21/18
Inventor 吕剑韩升曾纪珺张伟赵波谷玉杰唐晓博杨志强郝志军亢建平李凤仙
Owner XIAN MODERN CHEM RES INST