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Fluorocarbons and Life Support of Humanity

Tech Area / Field

  • CHE-IND/Industrial Chemistry and Chemical Process Engineering/Chemistry
  • MED-DRG/Drug Discovery/Medicine

3 Approved without Funding

Registration date

Leading Institute
Russian Scientific Center of Applied Chemistry, Russia, St Petersburg


  • Freie Universität Berlin / Institut für Chemie / Anorganische u. Analytische Chemie, Germany, Berlin\nLodestar Inc., USA, NJ, Howell\nUniversity of Padova / Facolta di Ingegneria di Padova, Italy, Padova

Project summary

Conversion of elemental fluorine production facilities, earlier applied in nuclear weapons production technology, is currently one of actual problems that open wide range of possibilities to use elemental fluorine in products for peaceful applications. The usage of fluorine in synthesis of polyfluorinated organics with a variety of uncial properties, such as high thermal and chemical resistance, explosion safety, fire-safety etc. is one directions.

In the recent years perfluorinated organic substances with 8-10 C-atoms have obtained large scientific and practical meaning. Those substances include, cyclic and aliphatic perfluorocarbons, e.g., perfluorodecalin, perfluorooctane, perfluorotripropylamine, other perfluorinated linear or cycle amines. Those are inert liquids that, besides of their thermal and chemical stability, have such uncial properties as gas, particularly, oxygen solvency (up to 45% by vol.). It allows us to apply them in medicine and biology for gas-carrier media when transporting oxygen to cells in vivo and removing carbon dioxide from blood.

One of their possible applications is the creation of the new type of blood-substitutes that does not require any group compatibility when used. The creation of such artificial blood-substitutes is of the greatest importance for saving people in emergency at extreme cases that may arise at any country, when huge reserve of blood is needed and time is critical. For instance, for saving people at earthquake, victims of terrorist acts similar to that had place in USA on the 11th of September, 2001, or any other global catastrophes.

High transparency and high specific gravity (1,8-1,9 g/cm3) opened wide range of possible applications for those perfluorocarbons in ophthalmology for curing retina separation or other eye-microsurgery applications.

The next very important application of those compounds is their usage in the apparatus for liquid respiration used in deep underwater works, e.g. in petroleum production from sea or ocean bottom. It is well known that the on-land oil resources are being depleted, and those under water will soon become the main source.

Research has been started on all applications under consideration, and there are positive results that allow us be sure in success of the project fulfillment in case that it is adopted.

The issue of the project is to investigate and develop the scientific base for synthesis of a number of inert perfluorocarbons that have some perspectives in their above-mentioned medical applications.

Here included:

1. The synthesis of perfluorodecalin (PFD) and its analogues through fluorination of the related hydrocarbon substances by the higher fluorides of variable-valency elements (СоF3, etc.), manufactured using elemental fluorine. In the project implementation it is suggested to study the influence of various parameters on the fluorination process so that to improve the synthesis conditions and to increase the target products output as much as possible.

The available published data on the synthesis of high-molecular perfluorocarbons 1-5, 7-12 allow to conclude that the most perspective method for those substances preparation is that of using either elemental fluorine or the higher fluorides of variable-valency elements, e.g., CoF3, CeF4, MnF3, etc.

In so doing, fluorination with the higher fluorides of variable-valency elements is preferable because it permits to carry out the process at more mild conditions, and hence with higher yields and with lower heat-release during the reaction, and makes it possible to solve the problem of heat–removal during the process of fluorination.

2. The synthesis of perfluorotripropylamine through electrochemical fluorination of n-tripropylamine. It is well known /13/, that only electrochemical fluorination can provide perfluorinated tertiary amines with considerable output. During the project implementation it is suggested to study the influence of the electrolyte concentration and temperature, current density, anode structure, polarization regime and electrolyzer construction on the fluorination process, to choose the best synthesis conditions that provide the maximal yield of the target product. It is suggested to develop the conditions of the target product isolation from the crude product and to prepare experimental samples of perfluorotripropylamine.

3. In synthesis of inert perfluorocarbons one of the most important issues is to develop the method for cleaning the obtained substances so that they could be used in medicine and biology. It is suggested to investigate different product cleaning methods, such as cleaning with elemental fluorine on catalysts and with fluorine-carriers, cleaning with various oxidizers in special apparatuses used at FSUE RSC “Applied Chemistry” for production of high performance perfluorinated dielectric liquids. It is suggested to develop the design of the cleaning apparatus and to streamline some stages of the technology of the pure product isolation so that they could be further applied in pilot-industrial scale process development.

4. Synthesis of new perfluorocarbons, perfluorinated cyclic amines, perfluorinated ethers and esters by chemical and electrochemical methods for the further studies as perspective substances for medicine and biology.

5. Extremely severe purity requirements are imposed on inert perfluorocarbons to be used in medicine, and it must have an effect on their production technology. Both physical and chemical properties of the developed products must be thoroughly investigated, such as oxygen and carbon dioxide solvency at various temperatures and pressures, etc.

Both in Russia and all over the world there are considerable facilities for elemental fluorine manufacture now unused in connection with reduction of nuclear weapons. Synthesis of perfluorodecalin and its derivatives for above-mentioned medical and biological applications is a perspective line of inquiry for national economy.

Federal State Unitary Enterprise «Russian Scientific Center Applied Chemistry» (FSUE RSC «Applied Chemistry ») has got many years of experience (over 50 years) in manufacture and usage of elemental fluorine for special purposes and for synthesis of some freons: freon 14 (CF4), 218 (C3F8) and other.

Taking into account the available laboratory and experimental base, and specialists experienced in work with elemental fluorine, quick development of the works on elemental fluorine usage in synthesis of new fluorinated organics extremely needed for national economy is possible.

The decrease in fluorine consumption in special applications makes it possible to use hydrogen fluoride (formerly used for the main raw material in its synthesis) in the manufacture of the perfluorinated products intended for medicine and biology. Perfluorotripropylamine and other perfluorinated amines, esters, and ethers to be studied under this project, are prepared by the electrochemical fluorination method (ECF). Here hydrogen fluoride is used for the main raw material. The method includes electrolysis of hydrocarbon analogues (amines, ethers) dissolved in hydrogen fluoride.

Simons proposed the method in 1949. The most widely the method had been used by "3М" (USA).

The studies on electrochemical synthesis of perfluorinated organics are being conducted in Germany, Japan and some other countries. This kind of research is being carried out in Italy under the direction of professor Gambaretto (Facolta di Ingegneria Dell’Universita Di Padova, Instituto Di Chimica Industriale) /14-16/.

In Russia the technology of electrochemical synthesis of fluorinated substances was mostly developed by FSUE RSC «Applied Chemistry». The manufacture technologies for “Chromin”, perfluoroacids, perfluorodibutyl ether, and perfluorotriethylamine were developed and implemented in pilot-industrial scale. FSUE RSC «Applied Chemistry» owns the technology for electrochemical synthesis of perfluorinated substances. The enterprise has got the necessary experimental base and skillful personnel. RSC «Applied Chemistry» has got the needed production area, logistics and power supply.

List of references:

  1. Stasy M., Tetlow D./ Exhaustive fluorination of organic substance with higher fluorides of variable valency, “Progress in fluorine chemistry”, vol. 1, Moscow, “Chimia”, 1964, p. 424-471.
  2. Maximov B.N., Barabanov V.G. etc. “Industrial organofluoric products”, “Chimia”, St.Petersburg, 1996, 2nd Issue.
  3. Kornilov V.V., Kostyaev R.A., Maximov B.N., “Journal of Applied Chemistry” (Jurnal prikladnoi himii), 1994, vol. 67, #1, p.103-106.
  4. Maximov B.N., Kornilov V.V. et all., “Fluorination of ethylene with higher fluorides of cobalt, manganese, cerium”, “Journal of Applied Chemistry” (Jurnal prikladnoi himii), 1994, vol. 67, #1, p. 107-111.
  5. Pat. US 2578720, US, MKI CO 7C, Fluorination organic connections with the condensed nucleus with cobalt trifluoride.
  6. Pat. US 4777304, US, MKI CO 7C 17/12, Perfluorinated butyldecane.
  7. Patent Application JP 89.186828, Japan, MKI CO7C, 23/00, Exhaustive fluorination.
  8. Patent UK 1281822, United Kingdom, MKI CO7C, Fluorination of organic substances.
  9. Burdon J, Tatlow J C. et all. Tetrahedron, 1976, v.32, p. 1041-1043.
  10. Tatlow J.C., Oliver J A. et all. J. Fluorine Chem, 1975, v.6, #1, p. 19-36.
  11. Redler A.E., Tatlow J.C., J. Fluorine Chem., 1972, v. l, N 3, p. 337-345.
  12. Plevey R., Tatlow J. C., J. Fluorine Chem., 1982, v. 21, p. 265-268.
  13. Aba and Nagace, Chapter 2 in «Industrial organofluoric substances, manufacture and applications….», edited by Banks.
  14. G.P. Gambaretto, M. Napoli, L. Conte, A. Scipioni and R. Armelli, J. Fluorine Chem., 27, (1985) 149.
  15. M. Napoli, L. Conte, G.P. Gambaretto and F.M. Carlini, J. Fluorine Chem., 45 (1989) 213.
  16. M. Napoli, A. Scipioni and G.P. Gambaretto, F.M. Carlini and M. Bertola, J. Fluorine Chem., 67 (1994) 261-264.


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