Biotechnology Research Institute, National Research Council of Canada, 6100 Royalmount Ave., Montreal, Quebec, Canada H4P2R2.
Chemosphere. 2010 Mar;79(2):228-32. doi: 10.1016/j.chemosphere.2010.01.013. Epub 2010 Feb 2.
Nitroglycerin (NG), a nitrate ester, is widely used in the pharmaceutical industry and as an explosive in dynamite and as propellant. Currently NG is considered as a key environmental contaminant due to the discharge of wastewater tainted with the chemical from the military and pharmaceutical industry. The present study describes hydrolytic degradation of NG (200 microM) at pH 9 using either conventional or microwave-assisted heating at 50 degrees C. We found that hydrolytic degradation of NG inside the microwave chamber was much higher than its degradation using conventional heating. Products distributions in both heating systems were closely related and included nitrite, nitrate, formic acid, and the novel intermediates 2-hydroxypropanedial (OCHCH(OH)HCO) and glycolic acid (CH2(OH)COOH). Two other intermediates glycolaldehyde (CH2(OH)CHO) and glyoxylic acid (CHOCOOH) were only detected in the microwave treated samples. The molar ratio of nitrite to nitrate in the presence and absence of microwave heating was 2.5 and 2.8, respectively. In both microwave assisted and conventional heating a nitrogen mass balance of 96% and 98% and a carbon mass balance of 58% and 78%, respectively, were obtained. The lower C mass recovery might be attributed to further unknown reactions, e.g., polymerization of the aldehydes CH2(OH)CHO, CHOCOOH and OCHCH(OH)HCO. A hydrolytic degradation pathway for NG was proposed involving denitration (loss of 2 NO2(-)) from the two primary carbons and the loss of one nitrate from the secondary carbon to produce 2-hydroxypropanedial.
硝化甘油（NG），一种硝酸酯，广泛应用于制药工业，并用作炸药中的猛炸药和推进剂。目前，由于来自军事和制药工业的废水含有这种化学物质，NG 被认为是一种关键的环境污染物。本研究描述了在 pH 9 下使用常规或微波辅助加热（50°C）对 NG（200μM）的水解降解。我们发现，微波腔内的 NG 水解降解速度远高于常规加热时的降解速度。两种加热系统中的产物分布密切相关，包括亚硝酸盐、硝酸盐、甲酸和新的中间产物 2-羟基丙二醛（OCHCH（OH）HCO）和甘醇酸（CH2（OH）COOH）。另外两种中间产物乙二醇醛（CH2（OH）CHO）和乙醛酸（CHOCOOH）仅在微波处理的样品中检测到。在存在和不存在微波加热的情况下，亚硝酸盐与硝酸盐的摩尔比分别为 2.5 和 2.8。在微波辅助和常规加热中，氮的质量平衡分别为 96%和 98%，碳的质量平衡分别为 58%和 78%。较低的 C 质量回收率可能归因于进一步未知的反应，例如醛 CH2（OH）CHO、CHOCOOH 和 OCHCH（OH）HCO 的聚合。提出了 NG 的水解降解途径，涉及从两个主要碳原子上的脱硝化（损失 2NO2（-））和从次级碳原子上的损失一个硝酸盐，以产生 2-羟基丙二醛。
