Summary
The central orthogonal composite design methodology is employed to find optimum conditions for the conversion of alkyl halogenides into alkyl azides in a chromatographic system. In spite of the difference in the chemical structure of the starting alkyl halogenides, we have found that there is a similarity in the effect of various factors on the conversion process of alkyl halogenides into the corresponding azides. Conditions have been established which provide 100% conversion of n-butyland isopropyl iodide. Computation of the response functions by the corresponding regression equations permitted us to define a region of optimum conditions common for the primary and secondary propyl- and n-butyl iodides and bromides, as well as for n-pentyl iodide providing for a conversion at least 90–95%. Differences in the relative retention times of the alkyl halogenides and the corresponding azides are sufficient to carry out identification by the peak shift method.
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References
V. G. Berezkin, “Analytical Reaction Gas Chromatography”, Plenum Press, New York, 1968.
L. S. Ettre andW. H. McFadden, eds., “Ancillary Techniques in Gas Chromatography” Wiley—Interscience, 1969.
S. H. Langer andJ. E. Patton, in “New Developments in Gas Chromatography”,H. Purnell, ed., Interscience, Wiley, 1973, p. 294.
D. A. Leathard, “Advances in Chromatography”, Vo. 13,J. C. Giddings E. Grushka, R. A. Keller andJ. Cazes, eds., M. Dekker, Inc., New York, 1975, p. 265.
V. V. Nalimov andN. A. Chernova, “Statisticheskie Methody Planirovaniya Extremal'nych Experimentov” (Statistical Methods of Extremal Experiments Planning), Nauka, Moscow, 1965.
V. S. Boltovskii, V. N. Stanischevskii andYu. I. Khol'kin, “Chromatographicheskii Analis v Chimii Drevesiny” (Chromatographic Analysis in Wood Chemistry), Zinatne, Riga, 1975, p. 136.
S. L. Morgan andS. N. Deming, J. Chromatogr.,112, 267 (1975).
J. Holderith, T. Toth andA. Varadi, J. Chromatogr.119, 215 (1976).
Yu. I. Pirogova, “Issledovanie Putei Povyscheniya Effectivnosti i Proizvoditel'nosti Preparativnych Gazochromatographicheskich Kolonok” (Study of the Increasing the Gas Chromatographic Columns Effectivity and Performance), Avtoreferat Candidatskoi Dissertacii, Gorky, 1975.
B. V. Stolyarov andA. L. Shavarda, J. Org. Chim.14, 202 (1978).
S. N. Sautin, “Planirovanie Experimenta v Chimii i Chimicheskoi Technologii” (Experiments Planning in the Chemistry and the Chemical Technology), Chimiya, Leningrad, 1975.
J. H. Boyer andI. Hamer, J. Am. Chem. Soc.77, 951 (1955).
N. Z. Vorob'jev andL. N. Vorob'jev, Avtorskoe svidetel'stvo S.S.S.R. (Inventor's certificate) 369410; Bull. Izobret. No. 10 (1973).
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Kartsova, L.A., Balakin, I.M. & Stolyarov, B.V. Reaction gas chromatography of alkyl halogenides. Optimization of the conversion into alkyl azides. Chromatographia 11, 720–724 (1978). https://doi.org/10.1007/BF02269107
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DOI: https://doi.org/10.1007/BF02269107