Other Industrial Pollutants and Natural Toxins

Abstract

Tris(l,3-dichloro-2-propyl)phosphate(I) and tris(2,3-dibromopropyl)-phospate(II) are industrial flame retardants which have been used to impregnate fabrics. The carcinogenicity of II resulted in its removal from commercial products. A key scientific study, which indicated human exposure to II, was the negative-ion atmospheric pressure ionization MS detection of 2,3-dibromopropanol, a hydrolysis product of II, in the urine of children wearing pajamas treated with this flame retardant.⁽¹⁾ The analytical procedure involved selective-ion monitoring of the m/z 81 and 79 bromine isotopes. The rat also metabolized II to give a diester urinary metabolite which was identified by the mass spectra of its corresponding methyl derivative. The EIMS of this compound did not give a molecular ion but a relatively intense [M — Br]⁺ ion at m/z 429 (3 Br) and several diagnostic fragment ions were observed. The chlorinated flame retardant I was also metabolized in the rat to a bis phosphate which was identified by the MS of the trimethylsilyl derivative.⁽²⁾ Recently, negative chemical ionization mass spectral screening of human seminal fluid has identified I by its m/z 463 ion (i.e., M⁺ + CI) which exhibited an ion cluster pattern characteristic of a CI₇ species.⁽³⁾