662-01-1

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 117, p. 5397, 1995 DOI: 10.1021/ja00124a038

InChI:InChI=1/C3Cl2F6/c4-2(8,9)1(6,7)3(5,10)11

Upstream product

• 2354-04-3 1,1,3,3-tetrachloro-1,2,2,3-tetrafluoropropane 
• 3182-26-1 1,1,1,3,3,3-hexachloro-2,2-difluoro-propane 
• 812-32-8 tetrachloro-1,2,2-trifluoro-1-iodo-propane 
• 678-77-3 hexafluoropentanedioyl dichloride 
• 355-85-1 disilver hexafluoroglutarate 
• 931-91-9 1,1,2,2,3,3-Hexafluoro-cyclopropane 
• 680-00-2 1,1,2,2,3,3-hexafluoropropane 
• 7732-18-5 water 
• 7783-56-4 antimony(III) fluoride 
• 354-34-7 trifluoroacetyl fluoride 
• 14683-12-6 tellurium 
• 75-71-8 Dichlorodifluoromethane 
• 15086-10-9 tritium 
• 116-14-3 polytetrafluoroethylene 

Downstream Products

• 422-55-9 1-chloro-1,1,2,2,3,3-hexafluoropropane 
• 422-86-6 perfluoropropyl chloride 

Relevant academic research and scientific papers

PROCESSES FOR THE SYNTHESIS OF 3-CHLOROPERFLUORO-2-PENTENE, OCTAFLUORO-2-PENTYNE, AND 1,1,1,4,4,5,5,5-OCTAFLUORO-2-PENTENE

Disclosed is a process comprising reacting CF3CF2CCI2CF2CF3 (CFC-41 -10mca) with hydrogen in the presence of a dehalogenation catalyst to produce CF3CF2CCI=CFCF3 (CFC-1419myx). Also disclosed herein is a process comprising reacting CF3CF2CCI=CFCF3 (CFC- 1419myx) with hydrogen in the presence of a dehalogenation catalyst to produce CF3CF2C≡CCF3 (octafluoro-2-pentyne). Also disclosed herein is a process comprising reacting CF3CF2CCI2CF2CF3 (CFC-41 -10mca) with hydrogen in the presence of a dehalogenation catalyst to produce CF3CF2C≡CCF3 (octafluoro-2-pentyne). In addition, a process for reacting CF3CF2C≡CCF3, in a pressure vessel, with a Lindlar catalyst and hydrogen to produce CF3CF2CH=CHCF3 (1,1,1,4,4,5,5,5-octafluoro-2- pentene) is disclosed.

Preparation of highly fluorinated cyclopropanes and ring-opening reactions with halogens

Various highly fluorinated cyclopropanes 1 were prepared by reaction of the appropriate fluorinated olefins with hexafluoropropylene oxide (HFPO) at 180 °C. The fluorinated nitrile le was converted to the triazine derivatives 2a and 2b by catalysis with Ag2O and NH3/(CF3CO)2O, respectively. The fluorinated cyclopropanes reacted with halogens at elevated temperatures to provide the first useful, general synthesis of 1,3-dihalopolyfluoropropanes. At 150-240 °C, hexafluorocyclopropane and halogens X2 produce XCF2CF2CF2X (X = Cl, Br, I) in 50-80% isolated yields. Pentafluorocyclopropanes c-C3F5Y [Y = Cl, OCF3, OC3F7 and OCF2CF(CF3)OCF2CF2Z; Z = SO2F, CN, CO2Me] react regiospecifically at 150 °C to give XCF2CF2CFXY, c-C3F5Br reacts regioselectively with Br2 to give a 16.7:1 mixture of BrCF2CF2 CFBr2:BrCF2CFBrCF2Br, whereas c-C3F5H reacts unselectively with I2 to produce a statistical 2:1 mixture of ICF2CF2CFHI:ICF2CFHCF2I. Tri- and di(pentafluorocyclopropyl) derivatives 2 also undergo ring-opening reaction with halogens to give 16 and 17. Upon treatment of tetrafluorocyclopropanes 1j, 1k, and 1l with Br2 or I2, ring opening occurred exclusively at substituted carbons to give XCF2CF2CXY2. Thermolysis of the ring-opened product ICF2CF2CFIORF at 240 °C gave RFI and ICF2CF2COF in high yields.

Preparation of halogenated compounds

Halogenated compounds are prepared by ring opening reactions of highly fluorinated cyclopropanes with chlorine, bromine, iodine, or mixtures thereof at temperatures over 100° C. A novel compound, which is one type of compound produced, is a highly fluorinated and halogenated ether and other novel compounds are starting materials or products. The products of the process are useful as chain transfer agents for certain free radical polymerizations, and as chemical intermediates in the preparation of various products such as surfactants and textile surface treatments.

19F nuclear magnetic resonance studies of halogenated propanes

The relationship between 19F chemical shifts in halogenated propanes and their structures are elucidated using MNDO calculations to determine the population of rotamers.The pairs of atom gauche to a fluorine atom and van der Waals interaction between the two terminal substituents are responsible for the 19F chemical shifts.The differences among chemical shifts in diastereomers are also discussed in terms of the conformation of molecule.

HALOGEN FLUOROSULFATE REACTIONS WITH FLUOROCARBONS

The scope of the reaction of simple fluorocarbon halides with chlorine fluorosulfate and mixtures of chlorine and bromine fluorosulfate to produce RfOSO2F compounds has been investigated.It is shown that in many cases even primary chlorine in -CF2Cl groups can be replaced by -OSO2F.Primary bromine or iodine in -CF2X are more readily replaced.The mechanism of this replacement reaction has been established by the isolation of the metastable iodine III intermediate RfI(OSO2F)2.Neither secondary chlorine nor bromine in -CFX- groups is affected.With the secondary iodide, i-C3F7I, the salt + - is formed.Furthermore, it has been found that ClOSO2F is capable of converting fluorocarbon acids or their derivatives into fluorocarbon halides.A combination of these two ClOSO2F reactions with the known conversion of RfCF2OSO2F to the corresponding fluorocarbon acid offers a novel, high yield chain shortening reaction for the otherwise unreactive fluorocarbon halides according to: