Process for preparing perfluoroalkanesulfonyl fluorides

Chemistry: electrical and wave energy – Processes and products

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

204 81, C25B 300, C25B 308

Patent

active

054862710

ABSTRACT:
A process for preparing perfluoroalkanesulfonyl fluorides, e.g., perfluoromethanesulfonyl fluoride, is described which comprises electrochemically fluorinating in the presence of anhydrous hydrogen fluoride mono-, di- or tri- alkylsulfonyl alkyl esters or amides, or mono-, bis- or tris- alkylsulfonyl alkanes or disulfones. The process can be used to prepare perfluoroalkanesulfonyl fluorides in good yield and can be both more electrically-efficient and more fluorine-efficient than the conventional preparative method involving the electrochemical fluorination of hydrocarbon alkanesulfonyl halides.

REFERENCES:
patent: 2519983 (1950-08-01), Simons
patent: 2732398 (1956-01-01), Brice et al.
patent: 3028321 (1962-04-01), Danielson et al.
patent: 3333007 (1967-07-01), Scanley
patent: 3419595 (1968-12-01), Hansen
patent: 3692643 (1972-09-01), Holland
patent: 4411841 (1983-10-01), Geisler
patent: 4739103 (1988-04-01), Hansen et al.
patent: 4970337 (1990-11-01), Bielefeldt et al.
patent: 5326437 (1994-07-01), Bulan et al.
Ser. No. 08/085,540 filed Jun. 30, 1993 to Behr.
Willis, C. J., "Inorganic Analogues of Olefins" Thesis Cambridge University, pp. 32-43, 110-111 Sep. (1958).
March, J., Advanced Organic Chemistry, Third Edition, John Wiley & Sons, New York, pp. 358, 363, 376, 411, 445, and 1089 No Month (1985).
Farng and Kice, "Substituted Reactions of Alkanesulfonyl Derivitives," J. Am. Chem. Soc. No Month 1981, 103, 1137-1145.
Fluorine Chemistry, edited by J. H. Simons, pub. No Month 1950 Academic Press, Inc., New York, vol. 1, pp. 416-418.
Gard et al., "New Perfluoro and Perfluoralkoxy Sulfonyl Fluorides Part V. Fluorination Studies," Journal of Fluorine Chemistry, 55, pp. 313-321, (1991) No Month.
Stang, P. J. and White, M. J., "Trific Acid and It's Derivatives," Aldrichima Acta, vol. 16, pp. 15-22 (1983) No Month.
Novikova et al., "Synthesis of trifluoromethyl sulfonic acid fluoride by direct gas-phase fluorination of (fluorosulphonyl) difuoroacetic acid fluoride," Journal of Fluorine Chemistry, vol. 58, Nos. 2-3, Aug.-Sep. 1992, p. 326.
Rozhkov, I. N., "Anodic Fluorination," Organic Electrochemistry, Second Edition, Marcel Dekker, Inc., New York and Basel, pp. 803-825 (1983) No Month.
Preparation, Properties, and Industrial Applications of Organofluorine Compounds, Banks, ed., John Wiley & Sons, New York, pp. 37-43, (1982) No Month.
Howells et al., "Trifluoromethanesulfonic Acid and Derivatives," Chemical Reviews, vol. 77, Feb. 1977, pp. 69-92.
Hollitzer et al., "The Electrochemical Perfluorination (ECPF) Of Propanesulfonyl Fluorides, Part I. Preparation and ECPF Of 1-Propanesulfonyl Fluoride and 1,3-Propanedisulfonyl Difloride," Journal of Fluorine Chemistry, 35, pp. 329-341, (1991) No Month.
Volkov, N. D., et al., "Preparation of Halodifluoromethanesulfonic Acid Derivatives," Synthesis, pp. 972-975 (1979) No Month.
Clark, "Perfluoroalkyl Derivatives of the Elements," Advances in Fluorine Chemistry, vol. 3, pp. 19, 25-29, 55-56, Butterworths, London (1963) No Month.
Sokol'skii, G. A. and Dmitriev, M. A., "Electrochemical Fluorination of Methyl Chlorosulfonate," Zhurnal Obshchei Khimii, vol. 31, No. 3, pp. 706-710, (Mar. 1961).
Sokol'skii, G. A. and Dmitriev, M. A. "Hexafluorodimethylsulfonate," Zhurnal Obshchei Khimii, vol. 31, No. 4, pp. 1107-1110, (Apr. 1961).
Haszeldine, R. J. and Kidd, J. M., "Perfluoroalkyl Derivatives of Sulphur . . . ," J. of the Chemical Society, pp. 2901-2910 May (1955).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for preparing perfluoroalkanesulfonyl fluorides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing perfluoroalkanesulfonyl fluorides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing perfluoroalkanesulfonyl fluorides will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1502892

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.