Preparation of Methoxy and Ethoxy Nonafluorobutanes

Sun-Hee Hwang; Ju-Ryun Kim; Sang Deuk Lee; Hyunjoo Lee; Hoon Sik Kim; Honggon Kim

Journal of Industrial and Engineering Chemistry, Vol.13, No.4, 537-544, July, 2007

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Preparation of Methoxy and Ethoxy Nonafluorobutanes

Sun-Hee Hwang, Ju-Ryun Kim, Sang Deuk Lee , Hyunjoo Lee , Hoon Sik Kim¹, and Honggon Kim^†

Energy and Environment Technology Division, Korea Institute of Science and Technology, P.O. Box 131,Cheongryang, Seoul 130-650, Korea
¹Department of Chemistry, Kyunghee University, 1 Hoegy-dong, Dongdaemoon-gu, Seoul 130-701, Korea

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Syntheses of methoxynonafluorobutane (C4F9OCH3) and ethoxynonafluorobutane (C4F9OC2H5), which are considered as prospective third generation alternative cleaning agents replacing CFC-113 (CF2ClCFCl2), CH3CCl3, and HCFC-141b (CH3CFCl2), were studied. Heptafluorobutyryl chloride (C3F7COCl) or heptafluorobutyryl fluoride (C3F7COF) was firstly reacted with alkali metal fluoride (KF or CsF) in an aprotic polar solvent to produce alkali metal nonafluorobutoxide. It was consecutively converted to C4F9OCH3 and C4F9OC2H5 through the reaction with alkylating agents such as dimethyl sulfate, methyl trifluoromethane sulfonate and diethyl sulfate. Identification and characterization of major products were carried out by GC-MS, FT-IR, 1H-NMR, and 19F-NMR spectroscopies.

Keywords:methoxynonafluorobutane;ethoxynonafluorobutane;perfluoroacyl halide;heptafluorobutyryl chloride;heptafluorobutyryl fluoride;nonafluorobutoxide

[References]

Rosenqvist P, in Proc. The Earth Technology Forum Conference, pp. 75-80, Washington D.C., United States (1998)
Tsai WT, J. Hazard. Mater., A119, 69 (2005)
Koenig T, Owens JG, The Role of Hydrofluoroethers in Stratospheric Ozone Protection, 3M Report 98-0212-0035-1 (1996)
Flynn RM, Grenfell MW, Moore GL, Owens JG, WO22356 (1996)
Park JH, Cha AJ, Kim HG, Bae JH, J. Korean Ind. Eng. Chem., 15(7), 773 (2004)
Cha AJ, Park JN, Kim H, Bae JH, J. Korean Ind. Eng. Chem., 16(4), 533 (2005)
Ishikawa N, Kitazume T, Yamazaki T, Mochida Y, Tatsuno T, Chem. Lett., 761 (1981)
Fawcett FS, Tullock CW, Coffmann DD, J. Am. Chem. Soc., 84, 4275 (1962)
Redwood ME, Willis CJ, Can. J. Chem., 43, 1893 (1965)
Sherman PD, Kavasmaneck PR, Kirk-Othmer Encyclopedia of Chemical Technology, M. Grayson Ed., 3rd Edn. vol. 9, p 342-347, John Wiley & Sons, New York (1983)
Scherer O, Millauer H, Deutsches Pat 1,294,949 (1969)
Stang PJ, Hanack M, Subramanian LR, Synthesis, 85 (1982)
Bates RB, Taylor SR, J. Org. Chem., 58, 4469 (1993)
Redwood ME, Willis CJ, Can. J. Chem., 45, 389 (1967)

[Related Articles]

[1] Rosenqvist P, in Proc. The Earth Technology Forum Conference, pp. 75-80, Washington D.C., United States (1998)

[2] Tsai WT, J. Hazard. Mater., A119, 69 (2005)

[3] Koenig T, Owens JG, The Role of Hydrofluoroethers in Stratospheric Ozone Protection, 3M Report 98-0212-0035-1 (1996)

[4] Flynn RM, Grenfell MW, Moore GL, Owens JG, WO22356 (1996)

[5] Park JH, Cha AJ, Kim HG, Bae JH, J. Korean Ind. Eng. Chem., 15(7), 773 (2004)

[6] Cha AJ, Park JN, Kim H, Bae JH, J. Korean Ind. Eng. Chem., 16(4), 533 (2005)

[7] Ishikawa N, Kitazume T, Yamazaki T, Mochida Y, Tatsuno T, Chem. Lett., 761 (1981)

[8] Fawcett FS, Tullock CW, Coffmann DD, J. Am. Chem. Soc., 84, 4275 (1962)

[9] Redwood ME, Willis CJ, Can. J. Chem., 43, 1893 (1965)

[10] Sherman PD, Kavasmaneck PR, Kirk-Othmer Encyclopedia of Chemical Technology, M. Grayson Ed., 3rd Edn. vol. 9, p 342-347, John Wiley & Sons, New York (1983)

[11] Scherer O, Millauer H, Deutsches Pat 1,294,949 (1969)

[12] Stang PJ, Hanack M, Subramanian LR, Synthesis, 85 (1982)

[13] Bates RB, Taylor SR, J. Org. Chem., 58, 4469 (1993)

[14] Redwood ME, Willis CJ, Can. J. Chem., 45, 389 (1967)