Abstract
Aldehydes and ketones readily react with 2,4-dinitrophenylhydrazine (2,4-DNPH) to form the corresponding hydrazones. This reaction has been frequently used for the quantification of airborne carbonyl compounds. Since unsymmetrical aldehydes and ketones are known to form isomeric 2,4-dinitrophenylhydrazones (syn/ anti-isomers), the influence of isomerization on the practicability and accuracy of the 2,4-DNPH-method using 2,4-dinitrophenylhydrazine-coated solid sorbent samplers has been studied with three ketones (methyl ethyl ketone (MEK), methyl isopropyl ketone (MIPK), and methyl isobutyl ketone (MIBK)). With all three ketones the reaction with 2,4-DNPH resulted in mixtures of the isomeric hydrazones which were separated by HPLC and GC and identified by mass spectroscopy and 1H nuclear magnetic resonance spectroscopy. The isomers show similar Chromatographic behaviour in HPLC as well as in GC, thus leading to problems in quantification and interpretation of Chromatographic results.
Similar content being viewed by others
References
Binding N, Thiewens S, Witting U (1986) Staub — Reinhalt Luft 46: 444–446
Levin J-O, Andersson K, Lindahl R, Nilsson C-A (1985) Anal Chem 57: 1032–1035
Schilder K, Binding N, Witting U (1990) Verhandlungen der Deutschen Gesellschaft für Arbeitsmedizin. Gentner, Stuttgart, pp 321–325
Smith RA, Drummond I (1979) Analyst 104: 875–877
Kuwata K, Uebori M, Yamasaki Y (1979) J Chromatogr Sci 17: 264–268
Kuwata K, Uebori M, Yamasaki H, Kuge Y (1983) Anal Chem 55: 2013–2016
Binding N, Witting U (1991) Fresenius J Anal Chem 339: 218–222
Ramirez F, Kirby AF (1954) J Amer Chem Soc 76: 1037–1044
Uralets VP, Rijks JA, Leclercq PA (1980) J Chromatogr 194: 135–144
Seibl J (1970) Organic Mass Spectrometry 3: 417–432
Behforouz M, Bolan JL, Flynt MS (1985) J Org Chem 50: 1186–1189
Karabatsos GJ, Vane FM, Taller RA, Hsi N (1964) J Amer Chem Soc 86: 3351–3357
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Binding, N., Müller, W. & Witting, U. Syn/anti isomerization of 2,4-dinitrophenylhydrazones in the determination of airborne unsymmetrical aldehydes and ketones using 2,4-dinitrophenylhydrazine derivation. Fresenius J Anal Chem 356, 315–319 (1996). https://doi.org/10.1007/s0021663560315
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s0021663560315