Glyoxal, the simplest dialdehyde, was first prepared by N. Lubawin in 1875, when he oxidized acetaldehyde with HNO3 or H2SeO3. The HNO3 method is still used commercially, along with metal-catalyzed gas-phase oxidation of ethylene glycol. At low temperatures, glyoxal forms yellow crystals; it melts at 15 °C and boils at 51 °C. Its low flash point (–4 °C) makes its green vapor explosive in air. It’s used chiefly in paper coating and textile finishing processes.
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