each mole of DNAN degraded. 2-hydroxy-4-nitroanisole (2-
HONAN) together with smaller amounts of DNP were detected
(Fig. 3) but neither the ortho- nor the para- ANAN isomer was
observed. Production of DNP started quickly and reached a maximum
at 7 d of irradiation. In a separate experiment, we found
DNP to be unstable under the same photolytic conditions giving
nitrocatechol as a major degradation product. This finding is in line
with an earlier study by Rao et al. (2013) who found the same
products and neither 2-ANAN nor 4-ANAN during photolysis of
DNAN. Interestingly, we detected several formamide derivatives
of both aminonitroanisole and aminonitrophenol, which most
likely resulted from the reaction of formaldehyde (or formic acid)
originally generated from the demethylation of the ArOAMe group
in DNAN with the amine groups of the amino derivatives.
As for hydrolysis, Hill et al. (2012), Salter-Blanc et al. (2013)
indicated the much slower hydrolysis of DNAN compared to TNT.
Although DNAN has been shown to hydrolyze to give mainly
DNP (Murto and Tommila, 1962; Rochester, 1963; Davies and
Provatas, 2006), the reaction occurred only under severe alkaline
conditions (PpH 12). Under natural environmental conditions,
DNAN does not hydrolyze.