Water Quality Division, Mekorot, Israel National Water Co., P.O.B 2012, 9 Lincoln St., Tel Aviv 61201, Israel.
Chemosphere. 2010 Apr;79(4):476-81. doi: 10.1016/j.chemosphere.2010.01.016. Epub 2010 Feb 26.
The mechanism and kinetics of the spontaneous decomposition of 2,2-bis(bromomethyl)propan-1,3-diol (DBNPG) and its decomposition daughter products were determined in aqueous solution at a temperatures range between 30 and 70 degrees C and pH from 7.0 to 9.5. DBNPG decomposition in basic aqueous solutions involves release of bromide ions through a sequential formation of 3-bromomethyl-3-hydroxymethyloxetane (BMHMO) and 2,6-dioxaspiro[3.3]heptane (DOH). DBNPG decomposition into BMHMO is a two-stage reaction. The first stage is an acid/base equilibrium, in which an alkoxide is formed. In the second stage, DBNPG predominantly undergoes an intramolecular nucleophilic substitution to form the BMHMO. The transformation rate increases with the pH and the energy barrier for the degradation is 98 kJ mol(-1). Good agreement was found between the rate coefficients derived from variations in the organic molecules concentrations and those determined from the changes in the Br(-) concentration. DBNPG is one of the most abundant pollutants in a studied polluted aquitard underneath industrial park in the northern Negev, Israel, and together with its by-products pose an environmental hazard. DBNPG half-life is estimated to be about 65 years. This implies that high concentrations of DBNPG will persist in the aquifer long after the elimination of all its sources.
在 30 至 70°C 的温度范围和 7.0 至 9.5 的 pH 值下，在水溶液中确定了 2,2-双（溴甲基）-1,3-丙二醇（DBNPG）及其分解产物的自发分解的机制和动力学。在碱性水溶液中，DBNPG 分解通过依次形成 3-溴甲基-3-羟甲基氧杂环丁烷（BMHMO）和 2,6-二恶螺[3.3]庚烷（DOH）释放溴化物离子。DBNPG 分解为 BMHMO 是一个两阶段反应。第一阶段是酸碱平衡，其中形成烷氧基。在第二阶段，DBNPG 主要通过分子内亲核取代形成 BMHMO。转化速率随 pH 值增加而增加，降解的能垒为 98 kJ mol(-1)。从有机分子浓度变化得出的速率系数与从 Br(-)浓度变化得出的速率系数之间存在良好的一致性。DBNPG 是在以色列内盖夫北部工业园区下受污染的含水层中最丰富的污染物之一，与其副产物一起构成了环境危害。DBNPG 的半衰期估计约为 65 年。这意味着，在消除其所有来源后，含水层中仍将存在高浓度的 DBNPG，并且会持续很长时间。
