Synthesis of Perfluoroalkyl Alcohol, 3-(Perfluorooctyl)propan-2-ol, Using Two-Step Alcoholization

Nguyen, Trung Hieu; Tae, Beom-Seok; Park, Jun-Seo; Lee, Kwang-Nam

doi:10.5012/jkcs.2012.56.5.603

HOME > Journal Browse > About Journal > Journal Vol & Issue > Full Record

Synthesis of Perfluoroalkyl Alcohol, 3-(Perfluorooctyl)propan-2-ol, Using Two-Step Alcoholization

Journal title : Journal of the Korean Chemical Society
Volume 56, Issue 5, 2012, pp.603-608
Publisher : Korean Chemical Society
DOI : 10.5012/jkcs.2012.56.5.603

Title & Authors

Synthesis of Perfluoroalkyl Alcohol, 3-(Perfluorooctyl)propan-2-ol, Using Two-Step Alcoholization
Nguyen, Trung Hieu; Tae, Beom-Seok; Park, Jun-Seo; Lee, Kwang-Nam;

Abstract

3-(Perfluorooctyl)propan-2-ol was synthesized using an alcoholization process. The synthesis consisted of two steps: (1) addition of the olefin propylene to perfluorooctyl iodide to yield the corresponding iodo-adduct perfluorooctyl propyl iodide and (2) hydrolysis of the adduct reacted with water and dimethylformamide to yield the final product. The adduct and product were analyzed using gas chromatography to determine the yield and purity. The optimal conditions for each step of the process were determined, and a 93% yield of adduct and 95% yield of final product was achieved.

Keywords

Perfluoroalkyl alcohol;Perfluoroalkyl iodide;Alcoholization;Fluorinated surfactant;

Language

English

Cited by

References

Kissa, E. In Fluorinated Surfactants and Repellents; Marcel Dekker, Inc.: New York, 2001; Vol. 97, p 1.

Lehmler, H. J. Chemosphere 2005, 58, 1471.

Loganathan, B. G.; Sajwan, K. S.; Sinclair, E.; Senthil Kumar, K.; Kannan, K. Water Res. 2007, 41, 4611.

Fromel, T.; Knepper, T. P. In Reviews of Environmental Contamination and Toxicology: Perfluorinated Alkylated Substances; Whitacre, D. M.; Voogt, P. d., Ed.; Springer: New York, 2010; Vol. 208, p 161.

Brace, N. O. J. Fluorine Chem. 1999, 93, 1.

Petrov, V. A.; Krespan, C. G. J. Fluorine Chem. 2000, 102, 199.

Lewandowski, G.; Meissner, E.; Milchert, E. J. Fluorine Chem. 2006, 127, 337.

Davis, C. R.; Burton, D. J.; Yang, Z.-Y. J. Fluorine Chem. 1995, 70, 135.

Hayashi, T.; Matsuo, M. U.S. Patent 4001309 (to Asahi Glass Company, Ltd., Tokyo, Japan), 1977.

10.

Brace, N. O. J. Fluorine Chem. 2005, 126, 7.

11.

Brace, N. O. J. Fluorine Chem. 1999, 96, 101.

12.

Brace, N. O. J. Fluorine Chem. 2001, 108, 147.

13.

Gambaretto, G.; Conte, L.; Fornasieri, G.; Zarantonello, C.; Tonei, D.; Sassi, A.; Bertani, R. J. Fluorine Chem. 2003, 121, 57.

14.

Paterová, J.; Skalický, M.; Rybácková, M.; Kvícalová, M.; Cvacka, J.; Kvícala, J. J. Fluorine Chem. 2010, 131, 1338.

15.

Yoneda, N. J. Fluorine Chem. 2004, 125, 7.

16.

Bargigia, G.; Tonelli, C.; Tortelli, V. U.S. Patent 4748282 (to Ausimont S.p.A., Milan, Italy), 1988

17.

Day, R. I. U.S. Patent 3283012 (to E.I. Du Pont de Nemours), 1966.

18.

McNair, H. M.; Miller, J. M. In Basic Gas Chromatography; John Wiley & Sons, Inc.: New York, 1997; p 1.

19.

Stuart, B.; Prichard, E. In Practical Laboratory Skills Training Guides; LGC, Teddington, UK: Cambridge, 2003; p 1.

20.

Grob, R. L.; Barry, E. F. In Modern Practice of Gas Chromatography; John Wiley & Sons, Inc.: New Jersey, 2004; p 25.