Acrolein hydrolysis byproducts are
a part of good industrial stewardship
practice. Aqueous acrolein is used worldwide as an industrial raw
material, an herbicide, an oilfield biocide, a hydrogen sulfide scavenger,
and a molluscicide. Industrial acrolein is obtained by the catalytic
oxidation of propylene followed by aqueous absorption and then by
distillations. Generally, the fate of aqueous acrolein is described
as occurring by hydrolysis, evaporation, absorption into the ground,
and its consumption by the intended application purposes and conditions.
Measurements of acrolein in water are normally confined to its loss.
However, its byproducts are rarely discussed. In this study, an aged
acrolein solution has been found to contain byproduct aldehydes, including
the major soluble 5,6-dihydro-2H-pyran-3-carboxaldehyde.
Despite acrolein’s facile hydrolysis degradation, this byproduct
is surprisingly stable in aqueous media for at least 25 years at ambient
temperatures. The presence of this byproduct has been established
by 1H and 13C NMR, using DEPT, COSY, and HMBC,
and UV spectroscopy at λmax 229 nm in natural water
systems.