TY - JOUR
T1 - Anaerobic biodegradation of nitroglycerin
AU - Christodoulatos, Christos
AU - Bhaumik, Syamalendu
AU - Brodman, Bruce W.
PY - 1997/6
Y1 - 1997/6
N2 - Nitroglycerin (C3H5(ONO2)3) or glycerol trinitrate (GTN), a constituent of various propellant formulations and a vasodilator prescribed to treat angina pectoris and other heart diseases, was completely mineralized in serum vials under strict anaerobiosis by mixed cultures from an anaerobic digester. Anaerobic biodegradation occurred via successive denitration of the parent molecule and production of glycerol dinitrate (GDN), and glycerol mononitrate (GMN), which was converted to a utilizable carbon source, most likely glycerol. Both isomeric forms of GDN were detected, namely glycerol 1,3-dinitrate (1,3-GDN) and glycerol 1,2-dinitrate (1,2-GDN), which were converted to glycerol 1-mononitrate (1-GMN) and glycerol 2-mononitrate (2-GMN). Significant regioselectivity of the enzymatic degradation was observed with preferential attack at the secondary (C2) nitro group, which favored production of 1,3-GDN and 1-GMN. Addition of cosubstrates substantially enhanced the rates of conversion of GTN; however, biodegradation also occurred in the absence of external carbon sources. The rates of biodegradation were significantly decreased at each successive denitration, with conversion of GMN to glycerol being the rate limiting step. The destruction of the GDN and GMN intermediates, which are more soluble than the parent compound, and possibly more toxic and mutagenic, is extremely important for the treatment of wastewater and soils contaminated with GTN. Nitrate and nitrite, the main nitrogen products of denitration, were also removed under anaerobic conditions.
AB - Nitroglycerin (C3H5(ONO2)3) or glycerol trinitrate (GTN), a constituent of various propellant formulations and a vasodilator prescribed to treat angina pectoris and other heart diseases, was completely mineralized in serum vials under strict anaerobiosis by mixed cultures from an anaerobic digester. Anaerobic biodegradation occurred via successive denitration of the parent molecule and production of glycerol dinitrate (GDN), and glycerol mononitrate (GMN), which was converted to a utilizable carbon source, most likely glycerol. Both isomeric forms of GDN were detected, namely glycerol 1,3-dinitrate (1,3-GDN) and glycerol 1,2-dinitrate (1,2-GDN), which were converted to glycerol 1-mononitrate (1-GMN) and glycerol 2-mononitrate (2-GMN). Significant regioselectivity of the enzymatic degradation was observed with preferential attack at the secondary (C2) nitro group, which favored production of 1,3-GDN and 1-GMN. Addition of cosubstrates substantially enhanced the rates of conversion of GTN; however, biodegradation also occurred in the absence of external carbon sources. The rates of biodegradation were significantly decreased at each successive denitration, with conversion of GMN to glycerol being the rate limiting step. The destruction of the GDN and GMN intermediates, which are more soluble than the parent compound, and possibly more toxic and mutagenic, is extremely important for the treatment of wastewater and soils contaminated with GTN. Nitrate and nitrite, the main nitrogen products of denitration, were also removed under anaerobic conditions.
KW - Anaerobic degradation
KW - Degradation pathway
KW - Energetic materials
KW - Glycerol trinitrate
KW - Kinetics
KW - Nitroglycerin
KW - Regioselectivity
KW - Wastewater treatment
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U2 - 10.1016/S0043-1354(96)00390-9
DO - 10.1016/S0043-1354(96)00390-9
M3 - Article
AN - SCOPUS:0031172573
SN - 0043-1354
VL - 31
SP - 1462
EP - 1470
JO - Water Research
JF - Water Research
IS - 6
ER -