422-91-3Relevant articles and documents
SYNTHESIS OF DIIODOPERFLUORO-C3 TO C7-ALKANES
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Paragraph 0089-0090, (2016/09/26)
The present invention is the process comprising forming a stable mixture comprising I(CF2)nI, wherein n is at least 3 and at least one of I(CF2)nI, wherein n is 1 or 2, as a contaminant in said mixture and heating said mixture to a temperature of at least 220° C. to reduce the amount of said contaminant to be no greater than 1% when said contaminant is ICF2I (n=1) and no greater than 0.1% when said contaminant is ICF2CF2I (n=2).
METHOD OF MAKING ALPHA, OMEGA-DIIODOPERFLUOROALKANES
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Page/Page column 12-13, (2014/05/07)
A method of making α,ω-diiodoperfluoroalkanes includes combining: diatomic iodine, at least one perfluoroalkylene oxide represented by the formula wherein Rf represents a perfluoroalkyl group; and at least one of: a) a first metallic compound comprising nickel, and a second metallic compound comprising molybdenum that is compositionally different from the first metallic compound; or b) a metallic alloy comprising from 50 to 70 percent by weight of nickel and from 20 to 40 percent by weight of molybdenum, based on the total weight of the metallic alloy, thereby producing at least one product represented by the formula I(CF2)nI, wherein n independently represents an integer in the range of from 1 to 11. The total weight of the at least one product wherein n is 3 or greater exceeds the total weight of the at least one product wherein n is 1 or 2 by a factor of at least 4.
Environmentally Benign Processes for Making Useful Fluorocarbons: Nickel- or Copper(I) Iodide-Catalyzed Reaction of Highly Fluorinated Epoxides with Halogens in the Absence of Solvent and Thermal Addition of CF2I 2 to Olefins
Yang, Zhen-Yu
, p. 2394 - 2403 (2007/10/03)
Highly fluorinated epoxides react with halogens in the presence of nickel powder or CuI at elevated temperatures to provide a useful and general synthesis of dihalodifluoromethanes (CF2X2) and fluoroacyl fluorides (RFCOF) in the absence of solvent. At 185 °C, hexafluoropropylene oxide and halogens produce CF2X 2 (X = I, Br) in 68-90% isolated yields, along with small amounts of X(CF2)nX, (n = 2, 3). With interhalogens I-X (X = Cl, Br), a mixture of CF2I2, CF2XI, and CF 2X2 was obtained. The fluorinated epoxides substituted with perfluorophenyl, fluorosulfonyl, and chlorofluoroalkyl groups also react cleanly with iodine to give CF2I2 and the corresponding fluorinated acyl fluorides in good yields. The reaction probably involves an oxidative addition of fluorinated epoxides into metal surfaces to form an oxametallacycle, followed by rapid decomposition to difluorocarbene-metal surfaces, which alters the reactivity of the difluorocarbene carbon from electrophilic to nucleophilic. The increase of nucleophilicity of difluorocarbene facilitates the reaction with electrophilic halogens. CF 2I2 reacted with olefins thermally to give 1,3-diiodofluoropropane derivatives. Both fluorinated and nonfluorinated alkenes gave good yields of the adducts. Reaction with ethylene, propylene, perfluoroalkylethylene, vinylidene fluoride, and trifluoroethylene provided the corresponding adducts in 58-86% yields. With tetrafluoroethylene, a 1:1 adduct was predominantly formed along with small amounts of higher homologues. In contrast to perfluoroalkyl iodides, CF2I2 also readily adds to perfluorovinyl ethers to give 1,3-diiodoperfluoro ethers.
Preparation of highly fluorinated cyclopropanes and ring-opening reactions with halogens
Yang, Zhen-Yu
, p. 4410 - 4416 (2007/10/03)
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.
Synthesis of new nitrogen-containing perfluoroalkyl iodides
Fukaya, Haruhiko,Hayashi, Eiji,Hayakawa, Yoshio,Abe, Takashi
, p. 117 - 123 (2007/10/03)
Perfluoro(dimethylamino)-, perfluoro(diethylamino)-, perfluoro(1-pyrrolidinyl)-, perfluoromorpholino-, perfluoropiperidino-and perfluoropropoxy-substituted perfluoroalkyl iodides were synthesized directly by the reaction of the corresponding perfluoroacyl fluorides with lithium iodide in high yield. Under controlled reaction conditions, it was possible to synthesize either iodo-perfluoroacyl fluorides or perfluoroalkylidene diiodides by the reaction of perfluoro(alkanedioyl) difluorides with lithium iodide. Perfluoro(α-alkylamino-substituted alkyl) iodides may be good candidates for the media of solar-pumped lasers.
