355-68-0Relevant articles and documents
PROCESS FOR PREPARING DECAFLUOROCYCLOHEXENE
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Page/Page column 3, (2010/06/11)
Disclosed herein is a process of preparing decafluorocyclohexene using hexafluorobenzene as a raw material. The hexafluorobenzene reacts with an activated fluorinating agent at 60-200° C. in an inert gas atmosphere. The activated fluorinating agent is prepared by mixing 1-50 wt % of cobalt difluoride with 50-99 wt % of other metal fluoride selected from calcium fluoride, magnesium fluoride, aluminum fluoride, sodium fluoride and potassium fluoride. The mixture reacts with fluorine gas at 200-400° C.
Electrochemical fluorination of toluene and benzotrifluoride in the presence of triallylamine
Matalin,Kaurova,Berenblit,Gribel'
, p. 2090 - 2092 (2008/09/17)
Electrochemical fluorination of benzotrifluoride in the presence of triallylamine as depolarizer was studied. The possibility of preparing perfluoromethylcyclohexane and its isomers with high current efficiency and substance yield in combination with perfluorinated tertiary amines was examined.
Electrochemical fluorination of unsaturated sulfides and sulfones
Grigor'eva,Shainyan,Kaurova,Gracheva,Lesnevskaya,Barabanov
, p. 1095 - 1100 (2007/10/03)
Electrochemical fluorination of some unsaturated sulfides and sulfones and their reactions with anhydrous HF were studied.
Skeletal Rearrangements during the Fluorination of C6-Hydrocarbons over Cobalt(III) Trifluoride
Burdon, James,Creasey, Jeremy C.,Proctor, Lee D.,Plevey, Raymond G.,Yeoman, J.R. Neil
, p. 445 - 447 (2007/10/02)
Perfluorination of hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, 2,3-dimethylbutane, methylcyclopentane and cyclohexane over cobalt(III) trifluoride gave, in each case except perhaps cyclohexane, a mixture of linear, branched and cyclic C6-fluorocarbons: the degree of skeletal rearrangement (excluding cyclohexane) varied from ca. 7percent (methylcyclopentane) to 96percent (2,2-dimethylbutane).A carbocation mechanism, which does not proceed to equilibrium, is suggested.
Synthesis of Functional Perfluorinated Resins, Branched Perfluorinated Ethers and Perfluoroalkanoyl Fluorides
Huang, Hsu-Nan,Lagow, Richard J.
, p. 871 - 875 (2007/10/02)
Functional-group-containing perfluorinated resins have been prepared by carefully controlled direct fluorination of poly-(3-methyloxetane-3-methanol).Branched perfluorinated ethers such as bis(perfluoroneopentyl) ether and perfluoro-(2,2-dimethylbutyl methyl ether) have also been synthesized by direct fluorination of alkanols.The by-products, perfluoroalkanoyl fluorides, are useful intermediates.
Reactions of Polyfluorocyclohexane- and Polyfluorocyclohexene-carbonitriles
Phull, Gurjeet S.,Plevey, Raymond G.,Tatlow, John Colin
, p. 455 - 458 (2007/10/02)
The vapour phase reaction of undecafluorocyclohexanecarbonitrile (1) with cobalt(III) or silver(II) fluoride caused stepwise saturation of the CN triple bond to give C6F11CF=NF and C6F11CF2NF2, whereas reaction in a sealed tube with silver(II) fluoride gave the azomethane C6F11CF2N=NCF2C6F11 and with silver(I) fluoride gave tris(undecafluorocyclohexyl)-s-triazine.Methylamine, isopropylamine, and dimethylamine with the nitrile (1) gave the corresponding amidines.Vapour phase fluorination of pentafluorobenzonitrile by cobalt(III) fluoride or potassium tetrafluorocobaltate(III) afforded the nitrile (1), together with nonafluorocyclohex-3-enecarbonitrile (4).The latter was oxidised by potassium permanganate to 3-cyanoheptafluorohexane-1,6-dioic acid.Nonafluorocyclohex-1-enecarbonitrile (2) underwent classical nucleophilic addition-elimination sequences with methanol and with sodium methoxide to give progressively octafluoro-2-methoxy-, heptafluoro-6,6-dimethoxy-, and hexafluoro-2,6,6-trimethoxy-cyclohex-1-enecarbonitrile, whilst with ammonia, 2-aminohexafluoro-6-iminocyclohex-1-enecarbonitrile was formed, again by stepwise addition-elimination.
THE REPLACEMENT OF VINYLIC HYDROGEN BY FLUORINE
Burdon, James,Parsons, Ian W.,Shommakhi, Ahmed
, p. 357 - 364 (2007/10/02)
In 3H,4H-tetrafluoro-3-thiolen and 1H,2H-octafluorocyclohexene, the conversion of -CH=CH- into -CH=CF- by fluorination over KCoF4 takes place by saturation to -CHF-CHF- followed by dehydrofluorination, and not by direct replacement of a vinylic hydrogen.
FLUORINATIONS WITH COMPLEX METAL FLUORIDES PART 8. RING REARRANGEMENT IN THE FLUORINATIONS OF QUINOLINE WITH CAESIUM TETRAFLUOROCOBALTATE AND WITH COBALT(III) FLUORIDE
Plevey, Raymond G.,Rendell, Richard W.,Tatlow, John Colin
, p. 413 - 428 (2007/10/02)
Fluorination of quinoline by caesium tetrafluorocobaltate at ca. 350 deg C afforded mainly a mixture of pentadecafluoro-2-azabicyclodec-1(2)-ene (E), and heptadecafluoro-1-azabicyclodecane (F), arising by skeletal rearrangement.Minor products were six polyfluorocyclohexapyridines (G-L) all with carbocyclic rings having the -(CF2)4 - moiety.Compound F was unreactive, but E was highly susceptible to nucleophiles, e.g. water and methanol.Isoquinoline was fluorinated similarly, but the only new product isolated was tridecafluoro-3-azabicyclodeca-1(6)-2-diene (R).The rearrangement occurring with quinoline prompted a re-examination of its fluorination by cobalt(III) fluoride.At ca. 350 deg C, compound F was the major product, with very little E: there were some ring-opened materials, the most important being tetradecafluoro-4-pentafluoroethyl-2-azaoct-2(Z)-ene (N).
Low-Temperature Fluorination of Aerosol Suspensions of Hydrocarbons Utilizing Elemental Fluorine
Adcock, James L.,Horita, Kiyoshi,Renk, Ehrengard B.
, p. 6937 - 6947 (2007/10/02)
This work describes a new concept in direct fluorination methodology and an apparatus designed to achieve conditions necessary for the rapid, continuous partial or complete fluorination of hydrocarbon molecules under controlled conditions of temperature and concentration.Results from the fluorination of neopentane are presented which indicate that although the degree of fluorination for a given set of conditions indicates a Gaussian distribution, investigation of specific isomers indicates significant deviations from statistical isomer distributions in fluorinated neopentanes.Photochemical assisted fluorinations of neopentane, 1,4-dioxane, cyclohexane, and 2,2-dimethyl-1,3-dioxolane are described which produce the perfluorinated analogues directly in good purity and in high yields.
Fluorination with Complex Metal Fluorides. Part 5. Fluorination of Nitriles over Caesium Tetrafluorocobaltate(III)
Phull, Gurjeet S.,Plevey, Raymond G.,Rendell, Richard W.,Tatlow, John Colin
, p. 1507 - 1511 (2007/10/02)
Benzonitrile and the isomers of benzenedicarbonitrile (phthalo-, isophthalo-, and terephthalo-nitrile) have been fluorinated over caesium tetrafluorocobaltate(III) at elevated temperatures to give a mixtures containing undecafluorocyclohexanecarbonitrile.In addition the dinitriles gave decreasing yields (1,4- > 1,3- > 1,2-) of the corresponding cyclohexanedircarbonitriles.Some reactions (addition, defluorination, hydrolysis, and reduction) of undecafluorocyclohexanecarbonitrile are described.
