N-Nitrosodiethanolamine Revisited

N-nitrosodiethanolamine is believed to be a weakly carcinogenic chemical, and as it occurs widely--in consumer products for example--it may constitute a significant hazard to humans. However, the chemical evidence concerning the identity, purity and properties of N-nitrosodiethanolamine is incomplete, and this casts some doubt on the basis of the current interest in this substance. In the present paper a purification procedure of synthetic N-nitrosodiethanolamine based on high-performance liquid chromatography is given. Other fractionation procedures such as gas liquid chromatography, ambient pressure column chromatography and distillation are shown to be inadequate. The purity and identity of purified N-nitrosodiethanolamine is established by means of electron impact and field ionization mass spectrometry, including metastable defocusing and collision induced decomposition techniques. Furthermore, 1H and 13C nuclear magnetic resonance and, to a lesser extent, infrared and ultraviolet spectroscopy are used. Deuterium labelled analogues of N-nitrosodiethanolamine and the parent diethanolamine are employed in rationalizing the results obtained.