Specialist Periodical Reports provide systematic and detailed review coverage of progress in the major areas of chemical research. Written by experts in their specialist fields the series creates a unique service for the active research chemist, supplying regular critical in-depth accounts of progress in particular areas of chemistry. For over 80 years the Royal Society of Chemistry and its predecessor, the Chemical Society, have been publishing reports charting developments in chemistry, which originally took the form of Annual Reports. However, by 1967 the whole spectrum of chemistry could no longer be contained within one volume and the series Specialist Periodical Reports was born. The Annual Reports themselves still existed but were divided into two, and subsequently three, volumes covering Inorganic, Organic and Physical Chemistry. For more general coverage of the highlights in chemistry they remain a 'must'. Since that time the SPR series has altered according to the fluctuating degree of activity in various fields of chemistry. Some titles have remained unchanged, while others have altered their emphasis along with their titles; some have been combined under a new name whereas others have had to be discontinued. The current list of Specialist Periodical Reports can be seen on the inside flap of this volume.

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Fluorocarbon and Related Chemistry Volume 3

A Review of the Literature Published During 1973 and 1974

By R. E. Banks, M. G. Barlow

The Royal Society of Chemistry

Chapter 1 Saturated Fluorocarbons, Fluorocarbon Hydrides, and Fluorocarbon Halides By R. E. Banks, 1, 
Chapter 2 Per-and Poly-fluorinated Olefins, Dienes, Heterocumulenes, and Acetylenes By M. G. Barlow and D.R. Taylor, 49, 
Chapter 3 Aliphatic Per-and Poly-fluorinated Carbonyl and Thiocarbonyl Compounds By A. E. Tipping and V. J. Davis, 127, 
Chapter 4 Per-and Poly-fluorinated Aliphatic Derivatives of the Main-Group Elements By R. E. Banks, 187, 
Chapter 5 Per-and Poly-fluorinated Aliphatic Derivatives of the Transition Elements By R. Fields, 308, 
Chapter 6 Per-and Poly-fluorinated Aromatic Compounds By J.M. Birchall and W. T. Flowers, 356, 
Appendix, 468, 
Author Index, 471,

CHAPTER 1

Saturated Fluorocarbons, Fluorocarbon Hydrides, and Fluorocarbon Halides

BY R. E. BANKS

1 Fluorocarbons

More information concerning the preparation, properties, and applications (lubricants, seals, and bearing; cathode components for high-energy batteries; g.s.c. stationary phase; precursor of diamonds and fluorinated diamonds) of poly(carbon monofluoride) ('graphite fluoride') is now available. Detailed experimental procedures for the direct fluorination of regular or pyrolytic graphite using autoclave, fluidized-bed, or normal flow techniques are now to hand; production of snow-white superstoicheiometric poly(carbon monofluoride), [CF1.12[plus or minus]0.03]n, by the flow or fluidized-bed method demands a reaction temperature range of 627 [plus or minus] 3 �C, outside which either carbon tetrafluoride plus soot (at > 630 �C) or black-to-grey substoicheiometric material (e.g. black [CF0.68]n at 540 �C) are formed. At atmospheric pressure, fluorine does not appear to attack graphite at temperatures below 450�C, but at pressures greater than 225 lbf in-2, reaction occurs spontaneously at 20�C and can lead to a violent explosion if the rate of introduction of fluorine into the autoclave is not regulated carefully. No decomposition of superstoicheiometric poly(carbon monofluoride) appears to occur at 650 — 700 �C in the presence of fluorine. More structural data for poly(carbon monofluoride) are available following an X-ray powder diffraction study on material pressed at 20 kbar and 150 �C and determination of the n.m.r. absorption mode second moment of commercial Fluorographite samples (see Vol. 2, p. 1, ref. 2) of stoicheiometry CFl.06 and CF1.15; the results of the latter study indicate that the most plausible layer structure comprises an infinite array of cis-trans-linked cyclohexane boats .

Direct fluorination (flow method) of 'graphite oxide', [C8O2(OH)2]n (from graphite/KMnO4-NaN03-H2SO4 at 66 �C) at 20 �C and 1 atm yields a powdery, pale grey, thermally (above 50 �C) and hydrolytically unstable 'oxyfluoride' (16.25 — 22.4% F; λmax 1095 cm-1 (C — F stretch); c[florin].1 [C4F]n 1090 cm-1, [CF1.12[plus or minus]0.03]n 1217s ([??]C — F), 1342m, 1072w (peripheral CF2) cm-1}.1

Full details have been published of the direct fluorination of hydrocarbon polymersl6 by the so-called LaMar procedure, the principal feature of which is inhite dilution initially with helium or nitrogen followed by gradient changes of fluorine concentration ; with substrate particle sizes greater than lo0 mesh a hydrocarbon core is retained, and large fabricated items such as polyethylene bottles can be given a fluorocarbon skin of thickness ca. 0.2. Complete, or almost complete, fluorination of finely powdered (< 100 mesh) polyethylene, polypropylene, poly(ethylene-co-propylene), polyisobutylene, polyacrylonitrile, polystyrene, and poly-p-xylylene can readily be achieved at room temperature, the nitrile {->[CF•CF(CF2•NF2)]n} and benzenoid polymers undergoing fluorine addition as well as hydrogen substitution (see Scheme 1); polyacrylamide17 and phenol-formaldehyde resins or prepolymers (resols, novolacs) seem to suffer cleavage of pendant groups whilst undergoing change to fluorocarbon systems, and all the linear polymers appear to become cross-linked.

Instructions for the conversion of polynuclear arenes (coronene, anthracene, decacyclene, naphthacene, naphthalene, pentacene, ovalene, 9,1 O-benzphenanthrene, 1,2-benzanthracene, 1,3,6,8-tetraphenylpyrene) into the corresponding perfluoroalicyclic compounds and of 1,4-dichlorobenzene into perfluorocyclohexane by 'LaMar' controlled-concentration direct-flow fluorination at room temperature and atmospheric pressure are now available in the patent literature, and precise details of the use of the method, in conjunction with a cryogenic reactor, to convert neopentane into perfluoroneopentane in low yield (10 % after g.l.c. isolation) are also to hand. The results of kinetic studies on the direct fluorination of methane, [2H2]methane, halogenomethane, and olefins are likewise in print. Treatment of the perfluoropropene dimers (CF3)2C:CF•CF2•CF3 and trans(CF3)2CF•CF:CF•CF3 with fluorine at - 78 �C yields perfluoro-(2-methylpentane) quantitatively, while fluorination of a mixture of the trimers [(CF3)2CF]2C:CF•CF3 and (CF3)2C:C(CF2•CF3)•CF(CF3)z provides the corresponding nonane [(CF3)2CF]2-CF•CF2•CF3 (~95 %) at 30 �C but mainly its isomer (CF3)2CF•C(CF3)(CF2 • CF3)2 at 100 �C, plausibly via the rearrangement depicted in Scheme 2. Direct fluorination of the trimer (CF3)2(CF•CF:C(CF3)•CF2•CF2•CF3 [from CF3•CF:CF2/(CF3•CHF•CF2•O•CH2•CH2)3N/DABCO in DMSO at 36 — 38 �C] gives the perfluorononane (CF3)2CF•CF2•CF(CF3)•CF2•CF2•CF3, while the tetramer [(CF3)2CF]2C:C(CF3)•CF(CF3)2 [from oligomerization of CF3•CF:CF2 as in Scheme 2 but at higher temperatures], at 75 �C (no reaction occurs at 20 �C),undergoes cleavage with formation of [(CF3)2CF]2CF•CF2•CF3, CF3•CF2•CF2•-CF(CF3)• CF(CF3)2. and C3F8. Treatment of syn- perfluorooctamethyltricyclo[4,2,0,0]octa-3,7-diene (from dimerization of perfluorotetramethylcyclobutadiene) or of i s valence isomer perfluoro-octamethylcyclo-octatetraene (see p. 96) with fluorine at - 78 to 163 �C in an attempt to provide chemical evidence of structure (double bond 'co2nt') gave complex mixtures which were not investigated.

Data provided by a kinetic study of the thermal (280 — 450 �C) fluorine-perfluorocyclobutane reaction [activation energy: 170 [plus or minus] 2 kJ mol-1(40.5 [plus or minus] 0.5 kcal mol-1); products: CF4, C2F6, C3F8, n-C4Fl0] have been discussed in terms of initiation by SH2 attack of fluorine atom on ring carbon followed by the sequence presented in Scheme 3 (* indicates a thermally excited species). The possibility that the Cl — C3 fluorocarbons arose via fluorinolysis of perfluoro-n-butane formed first was excluded by lack of reaction in a separate experiment between perfluoropropane and fluorine at 477 �C for 30 h, conditions under which perfluorocyclohexane likewise fails to suffer attack, the difference in reactivity between these fluorocarbons and perfluorocyclobutane presumably arising from ring-strain effects ; consideration of...

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