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Adipic Acid: Cyclohexanol Oxidised with Boiling Nitric Acid, 1925
Cyclohexanol dripped slowly into boiling concentrated nitric acid is oxidised to adipic acid, which crystallizes when the liquid cools (Organic Syntheses, 1925: 500 g cyclohexanol gives 375–386 g). The acid must already be boiling, or unreacted cyclohexanol can explode. Adipic acid is half of nylon 66.
The picture: our diagram of the four stages.
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