The use of sodium triacetoxyborohydride
(STAB) as a mild and effective
reagent for the reduction of imines is well characterized in the literature.
For reduction products that require a nonacidic workup, but cannot
tolerate a strongly basic quenching regime, the reaction mixture is
typically quenched with bicarbonate solution in excess to neutralize
any remaining active reagent. We recently experienced a near-miss
incident in our pilot plant operation, where the drummed, aqueous
waste stream from a reductive amination process generated unexpected
internal pressure, resulting in significant deformation of a mild
steel drum during temporary storage. This article details the incident,
associated hazard evaluation investigation, and recommendation to
prevent future occurrences. The root cause was determined to be the
slow reaction (hence slow generation of carbon dioxide) of weekly
acidic boric acid, with excess potassium bicarbonate, present in the
fully quenched aqueous waste stream.