Synthesis and characterization of a new class of polyfluorinated alkanes: tetrakis(perfluoroalkyl)alkane |
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| Authors: | G. Gambaretto G. Fornasieri D. Tonei R. Bertani |
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| Affiliation: | a Dipartimento Processi Chimici dell’Ingegneria, Facoltà di Ingegneria, Via Marzolo 9, 35131 Padova, Italy
b Istituto di Scienze e Tecnologie Molecolari, CNR, Facoltà di Ingegneria, Via F. Marzolo 9, 35131 Padova, Italy |
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| Abstract: | The synthesis and physico-chemical characterization of 1,1,2,2-tetrakis(perfluoroalkyl-methylene)ethane {[F(CF2)nCH2]2CH}2 (n=6, TK6; n=8, TK8) are reported. The synthesis consists of four steps: (1) addition of allyl alcohol to a perfluoroalkyl iodide, F(CF2)nI (n=6,8) to give the corresponding iodo-adduct; (2) dehalogenation of the adduct by treatment with zinc in aqueous acetic acid, yielding 3-perfluoro-n-alkyl-1-propene; (3) addition of 3-perfluoro-n-alkyl-l-propene to perfluoroalkyl iodide, F(CF2)nI (n=6,8) to give 1,3-perfluoro-n-alkyl-2-iodo-propane; (4) coupling of 1,3-perfluoro-n-alkyl-2-iodo-propane by zinc in acetic anhydride giving the final products. TK6 and TK8 are characterized by very low surface tension values and exhibit very good properties as potential ski-waxes. |
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| Keywords: | (Perfluoroalkyl)alkanes Perfluoroalkyliodides Wurtz reaction Fluorinated lubricants |
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