TY - JOUR
T1 - Iron and Electron Shuttle Mediated (Bio)degradation of 2,4-Dinitroanisole (DNAN)
AU - Niedźwiecka, Jolanta B.
AU - Drew, Scott R.
AU - Schlautman, Mark A.
AU - Millerick, Kayleigh A.
AU - Grubbs, Erin
AU - Tharayil, Nishanth
AU - Finneran, Kevin T.
N1 - Funding Information:
We thank Kelly Nevin of the University of Massachusetts at Amherst for the original Geobacter metallireducens culture. This work was supported by the Department of Defense Strategic Environmental Research and Development Program (SERDP), project number ER-2222.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/9/19
Y1 - 2017/9/19
N2 - The Department of Defense has developed explosives with the insensitive munition 2,4-dinitroanisole (DNAN), to prevent accidental detonations during training and operations. Understanding the fate and transport of DNAN is necessary to assess the risk it may represent to groundwater once the new ordnance is routinely produced and used. Experiments with ferrous iron or anthrahydroquinone-2,6-disulfonate (AH2QDS) were conducted from pH 6.0 to 9.0 with initial DNAN concentrations of 100 μM. DNAN was degraded by 1.2 mM Fe(II) at pH 7, 8, and 9, and rates increased with increasing pH. Greater than 90% of the initial 100 μM DNAN was reduced within 10 min at pH 9, and all DNAN was reduced within 1 h. AH2QDS reduced DNAN at all pH values tested. Cells of Geobacter metallireducens were added in the presence and absence of Fe(III) and/or anthraquinone-2,6-disulfonate (AQDS), and DNAN was also reduced in all cell suspensions. Cells reduced the compound directly, but both AQDS and Fe(III) increased the reaction rate, via the production of AH2QDS and/or Fe(II). DNAN was degraded via two intermediates: 2-methoxy-5-nitroaniline and 4-methoxy-3-nitroaniline, to the amine product 2,4-diaminoanisole. These data suggest that an effective strategy can be developed for DNAN attenuation based on combined biological-abiotic reactions mediated by Fe(III)-reducing microorganisms.
AB - The Department of Defense has developed explosives with the insensitive munition 2,4-dinitroanisole (DNAN), to prevent accidental detonations during training and operations. Understanding the fate and transport of DNAN is necessary to assess the risk it may represent to groundwater once the new ordnance is routinely produced and used. Experiments with ferrous iron or anthrahydroquinone-2,6-disulfonate (AH2QDS) were conducted from pH 6.0 to 9.0 with initial DNAN concentrations of 100 μM. DNAN was degraded by 1.2 mM Fe(II) at pH 7, 8, and 9, and rates increased with increasing pH. Greater than 90% of the initial 100 μM DNAN was reduced within 10 min at pH 9, and all DNAN was reduced within 1 h. AH2QDS reduced DNAN at all pH values tested. Cells of Geobacter metallireducens were added in the presence and absence of Fe(III) and/or anthraquinone-2,6-disulfonate (AQDS), and DNAN was also reduced in all cell suspensions. Cells reduced the compound directly, but both AQDS and Fe(III) increased the reaction rate, via the production of AH2QDS and/or Fe(II). DNAN was degraded via two intermediates: 2-methoxy-5-nitroaniline and 4-methoxy-3-nitroaniline, to the amine product 2,4-diaminoanisole. These data suggest that an effective strategy can be developed for DNAN attenuation based on combined biological-abiotic reactions mediated by Fe(III)-reducing microorganisms.
UR - http://www.scopus.com/inward/record.url?scp=85029672506&partnerID=8YFLogxK
U2 - 10.1021/acs.est.7b02433
DO - 10.1021/acs.est.7b02433
M3 - Article
C2 - 28849653
AN - SCOPUS:85029672506
VL - 51
SP - 10729
EP - 10735
JO - Environmental Science and Technology
JF - Environmental Science and Technology
SN - 0013-936X
IS - 18
ER -