Skip to main content
SpringerLink
Log in

Effect of alkyl chain length on the electrochemical perfluorination of n-alkane (C6–C10) carboxylic acid chlorides

  • Original Paper
  • Published:
Journal of Applied Electrochemistry Aims and scope Submit manuscript

An Erratum to this article was published on 10 November 2007

Abstract

Electrochemical perfluorination (ECPF) of n-hexanoyl, n-heptanoyl, n-octanoyl, n-nonanoyl and n-decanoyl chlorides was carried out under identical experimental conditions in liquid HF. The product distribution among perfluorinated carboxylic acids, perfluoro ethers, perfluoroalkanes, isomerised and fragmented products containing less number of carbon atoms was identified using 19F NMR. The selectivity of C6–C10 perfluoro carboxylic acid varied between 29 and 36%. The alkali insoluble perfluoro cyclic ether and perfluoro alkane fractions increased with increasing chain length. The increase of perfluoroalkane fractions is mainly due to decarboxylation. Cyclic ether fractions also decreased slightly with increase in chain length. Among the cyclic ethers α substituted oxolanes were the predominant products. Six membered cyclic ethers were always found to contain β substitution. The possible pathways for these products are also indicated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. Diesslin AR, Kauck EA (1951) Fluoro carbon acids and derivatives. US Patent no. 2567011

  2. Kauck EA, Minn St.P, Simons JH (1952) Cyclic fluoro alkylene oxide compounds. US Patent no. 2594272

  3. Kauck EA, Minn St.P, Simons JH (1953) Cyclic fluorocarbon ethers. US Patent no. 2644823 (1954) British Patent no. 718318

  4. Ludwigshalle S A-G (1959) Method of producing organic cyclic Perfluoro ethers having 5 or 6-membered rings. German Patent no. 1069639 (1961) British Patent no. 862538

  5. Abe T, Nagase S (1982) In: Banks RE (ed) Preparation properties and Industrial application of organofluorine compounds. Ellis Horwood, Chichester, pp 19–33

    Google Scholar 

  6. Childs WV, Christensen L, Klink FW, Kolpin CF (1991) In: Lund H, Baizer MM (eds) Organic electrochemistry. Marcel Dekker, New York, pp 1103–1127

    Google Scholar 

  7. Alsmeyer YW, Childs WV, Flynn RM, Moore GGI, Smeltzer JC (1994) In: Banks RE, Smart BE, Tatlow JC (eds) Organofluorine chemistry. Plenum Press, New York, pp 121–143

    Google Scholar 

  8. Drakesmith FG (1997) Electrofluorination of organic compounds. In: Chambers RD (ed) Organofluorine chemistry: techniques and synthons, topics in current chemistry, vol 193. Verlag, Berlin, pp 197–242

    Google Scholar 

  9. Sartori P, Ignatev N (1998) J Fluor Chem 87:157

    Article  CAS  Google Scholar 

  10. Abe T (2000) J. Fluor Chem 105:181

    Article  CAS  Google Scholar 

  11. Conte L, Gamberetto G (2004) J Fluor Chem 125:139

    Article  CAS  Google Scholar 

  12. Abe T, Nagase S, Baba H (1976) Bull Chem Soc Jpn 49:1888

    Article  CAS  Google Scholar 

  13. Abe T, Kodaira K, Baba H, Nagase S (1978) J Fluor Chem 12:1

    Article  CAS  Google Scholar 

  14. Abe T, Nagase S (1979) J Fluor Chem 13:519

    Article  CAS  Google Scholar 

  15. Comninellis Ch, Javet Ph, Plattner E (1974) J Appl Electrochem 4:289

    Article  CAS  Google Scholar 

  16. Drakesmith FG, Hughes DA (1979) J Appl Electrochem 9:685

    Article  CAS  Google Scholar 

  17. Lines D, Sutcliffe H (1981) J Fluor Chem 17:423

    Article  CAS  Google Scholar 

  18. Drakesmith FG, Hughes DA (1986) J Fluor Chem 32:103

    Article  CAS  Google Scholar 

  19. Prokop HW, Zhou H-J, Xu S-Q, Wu C-H, Chuey SR, Liu CC (1989) J Fluor Chem 43:257

    Article  CAS  Google Scholar 

  20. Prokop HW, Zhou H-J, Xu S-Q, Wu C-H, Chuey SR, Liu CC (1989) J Fluor Chem 43:277

    Article  CAS  Google Scholar 

  21. Napoli M, Conte L, Gambaretto GP (1989) J Fluor Chem 45:213

    Article  CAS  Google Scholar 

  22. Chambers RD, Fuss RW, Jones M, Sartori P, Swales AP, Herkelmann R (1990) J Fluor Chem 49:409

    Article  CAS  Google Scholar 

  23. Napoli M, Scipioni A, Gambaretto GP, Carlini F M, Bertola M (1994) J Fluor Chem 67:261

    Article  CAS  Google Scholar 

  24. Scholberg HM, Brice HG (1955) US Patent no. 2717871

  25. Gramstad T, Haszeldine RN (1956) J Chem Soc 173 (1957) J Chem Soc 2460

  26. Brice TH, Trott PW (1956) US Patent no. 2732398

  27. Murray J (1977) Unpublished work as cited by A. J. Rudge in: Industrial Electrochemical Process, A. T. Huhn (ed) Elsevier, Amsterdam pp 77

  28. Kauck EA, Diesslin AR (1951) Ind Eng Chem 43:2332

    Article  CAS  Google Scholar 

  29. Ignatev NV, Wek-Biermann U, Heider U, Kucheryma A, Ansen SV, Hubel W, Sartori P, Willner H (2003) J Fluor Chem 124:21

    Article  CAS  Google Scholar 

  30. Velayutham D, Jayaraman K., Kulangiaappar K, Ilayaraja N, Rambabu Y, Santhan Rao P, Narayana Reddy S, Victor Babu K, Noel M (2006) J Fluor Chem 127:1111

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank the Ministry of Environment & Forests, Govt. of India, for financial support.

Author information

Authors and Affiliations

  1. Electro Organic Division, Central Electrochemical Research Institute, Karaikudi, 630006, India

    N. Ilayaraja, A. Manivel, D. Velayutham & M. Noel

Authors
  1. N. Ilayaraja
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Manivel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. Velayutham
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Noel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. Noel.

Additional information

An erratum to this article can be found at http://dx.doi.org/10.1007/s10800-007-9443-9

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ilayaraja, N., Manivel, A., Velayutham, D. et al. Effect of alkyl chain length on the electrochemical perfluorination of n-alkane (C6–C10) carboxylic acid chlorides. J Appl Electrochem 38, 175–186 (2008). https://doi.org/10.1007/s10800-007-9421-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10800-007-9421-2

Keywords

Search

Navigation