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United States Patent (19) 11) 4,423,261 Watanabe Et Al United States Patent (19) 11) 4,423,261 Watanabe et al. 45) Dec. 27, 1983 (54) PROCESS FOR PRODUCING A GRAPHITE (56) References Cited FLUOR DE COMPRISING MANLY POLYD CARBON MONOFLUORIDE U.S. PATENT DOCUMENTS REPRESENTED BY THE FORMULA (CF) 4,243,615 1/1981 Watanabe et al. 2,770,660 1 1/1956 Passino et al. ...................... 570/150 75 Inventors: Nobuatsu Watanabe, 136, Uguisudai, 3,872,032 3/1975 Kanemaru et al. 570/150 Nagaokakyo-shi, Kyoto, Japan; 3,925,492 12/1975 Ukaji et al. ... 570/150 Tsuyoshi Nakajima, Kyoto; 3,929,918 12/1975 Mesbri et al. ....................... 570/150 Masayuki Kawaguchi, Arida, both of 3,929,920 12/1975 Komo et al. ........................ 570/150 Japan Re 30,667 7/1981 Watanabe et al. 73) Assignees: Nobuatsu Watanabe; Applied Science Primary Examiner-Charles F. Warren Research Institute, both of Kyoto, Assistant Examiner-Joseph A. Boska Japan Attorney, Agent, or Firm-Armstrong, Nikaido, Marmelstein & Kubovcik (21) Appl. No.: 338,108 22 Filed: Jan. 8, 1982 57) ABSTRACT A graphite fluoride comprising mainly poly-dicarbon 30 Foreign Application Priority Data monofluoride represented by the formula (C2F)n can be Sep. 10, 1981 JP Japan ................................ 56-143007 produced in an extremely short period of time by a 51) Int. Cl. .............................................. C07C 17/00 process comprising reacting a graphite material with 52 U.S. C. .................................................... 570/150 fluorine in the presence of a specific fluoride. 58 Field of Search ......................................... 570/150 6 Claims, No Drawings 4,423,261 1. 2 Soc., 101,3832, (1979). There is a distinct difference in PROCESS FOR PRODUCING A GRAPHTE infrared spectrum between (CF) and (C2F). Illustra FLUORIDE COMPRISING MANLY tively stated, the absorption peak at 940 cm-1 is ob POLYD CARBON MONOFLUORIDE served in the IR spectrum of (C2F), whereas said peak REPRESENTED BY THE FORMULA (CF) is not observed in the IR spectrum of (CF)n, thus indi cating that (C2F) is utterly different in structure from This invention relates to a process for producing a (CF). graphite fluoride comprising mainly poly-dicarbon However, an extremely long period of time is disad monofluoride represented by the formula (C2F). More vantageously required for the formation of (C2F) by particularly, the present invention is concerned with a 10 completely fluorinating a graphite material without novel process for producing a graphite fluoride com leaving any of the raw graphite material unreacted until prising mainly poly-dicarbon monofluoride represented a constant weight of the resulting reaction product is by the formula (C2F)n, which comprises reacting a attained, especially under such mild conditions as will graphite material with fluorine in the presence of a give (C2F) with high selectivity. For example, when a specific fluoride whereby the reaction period of time is 15 natural graphite from Madagascar ore having a particle extremely shortened as compared with that of the con size of 200 to 250 mesh (Tyler) is reacted at 375 C. with ventional method, and which gives the graphite fluo fluorine gas of 200 mmHg, the reaction time required is ride in a yield as large as 100% with respect to a graph disadvantageously as long as 120 hours. Further, when ite material. a flaky graphite having a particle size of more than Conventionally known graphite fluoride is poly 20 about 20 mesh (Tyler) is employed as the graphite mate monocarbon monofluoride represented by the formula rial, the reaction time as long as several hundred hours (CF), which is highly appreciated, because of its pecu is needed. Thus, the known process for preparing the liar properties, in a wide variety of industrial applica novel graphite fluoride (C2F)n of excellent properties tion fields. For example, (CF) is useful as active materi has a serious drawbck in too long a reaction time als in electrolytic cells, lubricants, anti-wetting, stain 25 thereof, though it provides the desired product in ex resistant and water and/or oil-repellent materials, etc. tremely high yield with respect not only to the graphite Especially, in the field of electrolytic cells, (CF)n is material employed but also to the fluorine employed. known to be an active material capable of providing a We have made extensive and intensive investigations primary cell of high energy density and long shelf life in with a view to overcoming the above-mentioned draw which voltage drop due to discharge is scarcely ob 30 back. As a result, it has unexpectedly been found that served for a long period of time as disclosed in U.S. Pat. when the reaction of a graphite material with fluorine is No. 3,536,532 Specification. However, (CF) has fatal conducted in the presence of a specific fluoride, the rate drawbacks or disadvantages in the production thereof, of reaction increases greatly as compared with that of since the thermal decomposition temperature of (CF)n is the conventional process, leading to remarkable short extremely close to the temperature employed for the 35 ening of the necessary reaction period of time. The formation of the (CF), so that during the formation of present invention has been made based on such a novel (CF)n, (CF) formed is liable to decompose, resulting in finding, about which an illustrative explanation is give an extremely low yield of (CF). as follows. Watanabe et al. previously found a novel graphite A mixture of 0.8 g of flaky graphite and 1 g of, for fluoride, namely, poly-dicarbon monofluoride repre 40 example, aluminium fluoride (AlF3) was charged in a sented by the formula (C2F) and a process for the pro nickel vessel, and fluorine gas was then introduced to duction thereof. (C2F) can be produced in extremely 760 mmHg at room temperature to 100° C. The reaction high yield, and hence can be provided at comparatively system was then allowed to stand at the above tempera low cost. The novel graphite fluoride (C2F) can be ture for about 5 hours to form a graphite intercalation obtained, as described in detail in Japanese Patent Ap 45 compound of aluminium fluoride, which was heated to plication Laid-Open Specification No. 102893/1978, 400 C. at a temperature elevation rate of 3 C./min. U.S. Pat. No. 4,243,615 specification and U.S. reissued During the course of the heating, the interlayer spacing Patent No. Re 30,667 Specification, by heating a graph of the intercalation compound was expanded so as to ite material at a temperature of 300 to 500 C. in an release the intercalant AlF3 therefrom, that is, decom atmosphere of fluorine gas of 100 to 760 mmHg. As the 50 pose the intercalation compound while being accompa graphite material to be used for the production of nied by the weight decrease. When the heating was (C2F), there can be mentioned a natural graphite, an continued at 400 C. for 5 hrs, the reaction of the graph artificial graphite, a kish graphite, a pyrolytic graphite ite with fluorine proceeded rapidly. Thereby, the in and mixtures thereof. The resulting (C2F)n has a crystal tended graphite fluoride, namely a graphite fluoride line structure in which a layer structure is stacked with 55 comprising mainly (C2F)n could be obtained in a short an interlayer spacing of about 9.0 A to form a packing period of time. It is believed that the decomposition of structure, and in each layer, alternate carbon atom is the graphite intercalation compound and the formation bonded to one fluorine atom, as different from (CF) in of (C2F) do not completely stepwise occur but simulta which each carbon atom is bonded to one fluorine. neously to some extent. Each of (CF) and (C2F)n, however, has CF2 and CF3 60 The novel finding as described above is quite unex groups as the peripheral groups at the terminals of the pected and surprising, and has, for the first time, been carbon hexagonal network layer of the product. There made by the present inventors. fore, when fluorination of a graphite has been com More specifically, in accordance with the present pleted, the F/C ratios of the resulting (C2F)n and (CF) invention, there is provided a process for preparing a exceed 0.5 and 1.0, respectively. The excess amount of 65 graphite fluoride comprising mainly (C2F) which com fluorine due to the peripheral CF2 and CF3 groups in prises reacting a graphite material with fluorine in the creases as the crystallite size of the a,b-axis of a graphite presence of a fluoride of at least one element selected fluoride crystal becomes small see J. Amer. Chem. from the group consisting of elements of alkali metals 4,423,261 3 4. and alkaline earth metals, elements belonging to Groups The reaction system is then heated preferably to I(b), II(b) and III of the periodic table, and elements of about 300' to 500 C. The reaction period of time is not the first period of the transition elements. critical, and the reaction is continued until further The term "a graphite fluoride comprising mainly weight increase of the product is not observed. The (C2F),” used herein is intended to mean poly-dicarbon 5 period of time required for completion of the reaction monofluoride represented by the formula (C2F) or a can be extremely shortened as compared with that of polycarbon fluoride composition consisting essentially the conventional process. of C2F stoichiometry and CF stoichiometry, the con The graphite material to be used in the process ac tent of C2F stoichiometry being more than 50 mole %, cording to the present invention may be a natural based on the composition. The (C2F)n content of the 10 graphite, artificial graphite, kish graphite or pyrolytic product cannot be exactly theoretical.
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