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Synthesis of hydrofluoroalkanols and hydrofluoroalkenes

A technology for hydrofluoroalkanols and hydrofluoroalkenes, which can be applied to compounds of Group 2/12 elements of the periodic table, organic compounds of Group 2/12 without C-metal bonds, preparation of halogenated hydrocarbons, etc., and can solve the limitation And other issues

Inactive Publication Date: 2013-08-07
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However due to concerns related to global warming HFCs are now restricted

Method used

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  • Synthesis of hydrofluoroalkanols and hydrofluoroalkenes
  • Synthesis of hydrofluoroalkanols and hydrofluoroalkenes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1 shows the preparation of 2-chloro-3,3,3-trifluoropropanol from 1,1,1,2-tetrafluoro-2,2-dichloroethane.

[0058] in N 2 Add 32.8g (0.5mol) of active zinc powder, 12g (0.5mol) of paraformaldehyde and 180mL of anhydrous DMF into a 400mL Hastelloy C shaking tube. The tube was cooled to -15°C, and 64.4 g (0.2 mol) of 1,1-dichlorotetrafluoroethane was added. The reaction mixture was then stirred at 50°C for 6 hours. The results of gas chromatographic analysis of the reactions are summarized in Table 1. After the reaction mixture was cooled to room temperature, it was poured into a mixture of 200 mL of ice, 10% aqueous HCl and 200 mL of diethyl ether with stirring. After stirring for another 30 min, the organic layer was separated and washed with 100 mL of 2% aqueous HCl followed by 100 mL of brine. Using MgSO 4 After it was dried, the ether was removed in vacuo to obtain 13.36 g of product (8% yield).

[0059] Table 1

[0060] components

Embodiment 2

[0062] Example 2 shows the conversion of 2-chloro-2,3,3,3-tetrafluoropropanol to 2,3,3,3-tetrafluoro-1-propene.

[0063] in N 2 Add 26g (0.4mol) active zinc powder, 33.3g (0.2mol) 2-chloro-2,3,3,3-tetrafluoropropanol, 30.6g (0.3mol) ethyl alcohol to the 400mL Hastelloy C shaking tube anhydride and 180 mL of anhydrous DMF. The reaction mixture was then stirred at 50°C for 6 hours. After the reaction mixture was cooled to room temperature, the product was collected in a cold trap frozen with dry ice to obtain 18.1 g of 2,3,3,3-tetrafluoropropene.

Embodiment 3

[0065] Example 3 shows the synthesis of 2,3,3,3-tetrafluoro-1-propene from 1,1,1,2-tetrafluoro-2,2-dichloroethane.

[0066] in N 2 Add 20 g (0.315 mol) of active zinc powder, 7.5 g (0.25 mol) of paraformaldehyde and 130 mL of anhydrous DMF into a 400 mL Hastelloy C shaking tube. The tube was cooled to -15°C, and 43 g (0.25 mol) of 1,1-dichlorotetrafluoroethane was added. The reaction mixture was then stirred at 60°C for 6 hours. After the reaction mixture was cooled to room temperature, 30 g (0.46 mol) of active zinc powder and 50 g (0.5 mol) of acetic anhydride were added to the reactor. The reaction mixture was stirred at 50 °C for 6 hours, then cooled to room temperature. The gas and liquid phases were analyzed by GC-MS. The results are summarized in Table 2.

[0067] Table 2

[0068] Component (liquid phase)

[0069] Components (gas phase)

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Abstract

Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF=CHR from halofluorocarbons of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, comprising (1) reacting halofluorocarbons of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal to generate a reaction product comprising a metal hydrofluoroalkoxide, and reductively dehydroxyhalogenating said metal hydrofluoroalkoxide to produce a hydrofluoroalkene or (2) reacting a hydrofluoroalkanol of the structure RfCFXCHROH or a hydrofluoroalkoxide of the structure RfCFXCHROMX, wherein M is a reactive metal in the +2 oxidation state, with a carboxylic acid anhydride and a reactive metal in a reaction solvent to form a hydrofluoroalkene and isolating the hydrofluoroalkene. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(=O)R'.

Description

Background of the invention [0001] public domain [0002] In general, the present disclosure relates to methods of making hydrofluoroalkanols and methods of making hydrofluoroalkenes, and in particular to making 2,3,3,3-tetrafluoroalkanols and hydrofluoroalkanol esters. Fluoro-1-propene method. Background technique [0003] The refrigeration industry has been working for decades to find alternative refrigerants to the ozone-depleting chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) that are being phased out under the Montreal Protocol. For most refrigerant producers, the solution has been the commercialization of hydrofluorocarbon (HFC) refrigerants. However, due to concerns related to global warming, HFCs are now restricted. [0004] There is a continuing need for new and better methods of preparing halohydrocarbons that can be used as refrigerants or in other applications such as foam expansion agents, aerosol propellants, flame retardants or fire extingu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F3/00C07C17/363C07C23/06C07C29/40C07C31/28C07C67/08C07C69/63
CPCC07C17/363C07C69/63C07C23/06C07F3/003C07C67/08C07C29/40C07C17/10C07C2101/04C07C2601/04
Inventor M·J·纳帕X·孙L·M·亚古波尔斯基A·A·费拉托夫V·N·博伊科Y·L·亚古波尔斯基
Owner EI DU PONT DE NEMOURS & CO
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