PMID: 15707050Feb 15, 2005Paper

Chemical transformation of 3-bromo-2,2-bis(bromomethyl)-propanol under basic conditions

Environmental Science & Technology
Shai EzraJiwchar Ganor

Abstract

The mechanism of the spontaneous decomposition of 3-bromo-2,2-bis(bromomethyl)propanol (TBNPA) and the kinetics of the reaction of the parent compound and two subsequent products were determined in aqueous solution at temperatures from 30 to 70 degrees C and pH from 7.0 to 9.5. TBNPA is decomposed by a sequence of reactions that form 3,3-bis(bromomethyl)oxetane (BBMO), 3-bromomethyl-3-hydroxymethyloxetane (BMHMO), and 2,6-dioxaspiro[3.3]-heptane (DOH), releasing one bromide ion at each stage. The pseudo-first-order rate constant of the decomposition of TBNPA increases linearlywith the pH. The apparent activation energy of this transformation (98+/-2 KJ/mol) was calculated from the change of the effective second-order rate constant with temperature. The pseudoactivation energies of BBMO and BMHMO were estimated to be 109 and 151 KJ/mol, respectively. Good agreement was found between the rate coefficients derived from changes in the organic molecules concentrations and those determined from the changes in the Br- concentrations. TBNPA is the most abundant semivolatile organic pollutant in the aquitard studied, and together with its byproducts they posess an environmental hazard. TBNPA half-life is estimated to be about 100 years....Continue Reading

References

Aug 1, 1987·Environmental Science & Technology·T M VogelP L McCarty
Sep 1, 1982·Environmental Science & Technology·N E BurlinsonD H Rosenblatt

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Citations

Jun 22, 2013·Chemosphere·Yinon YecheskelBrian Berkowitz
May 13, 2006·Journal of Contaminant Hydrology·Shai EzraItzhak Bilkis
Aug 19, 2007·Environmental Science & Technology·Barbara G KutchkoNiels Thaulow

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