tags
Nitrogen dioxidenitrogensodiumsodium acetatenitrogen trioxideaceticacetic acidAcetic anhydrideoxygenNO2sodium nitratecalcium chlorideDCM

video tutorial Acetic anhydride from sodium acetate and nitrogen dioxide

  • Goal: test if acetic anhydride can be synthesized from sodium acetate and nitrogen dioxide; result confirms it's possible but impractical.
  • Safety: nitrogen dioxide is highly toxic; require excellent ventilation; avoid distilling the intermediate due to explosion risk.
  • Setup overview: generate NO2 from concentrated nitric acid, dry and route it through a cooled apparatus to react with anhydrous sodium acetate; condensation collects in the receiving flask; gas vented to ventilation; keep ice bath and cooling water for the condenser.
  • Reaction observations: NO2 absorbed into sodium acetate over ~30 minutes; blue-green color attributed to nitrogen trioxide in the condensed liquid; some NO2 escaped; larger condenser would have helped contain it.
  • Post-reaction notes: after completion, residual yellow-green liquid observed; mixture chilled to finish reaction; distillation of the mixture was attempted but dangerous due to NO2 release with organic material.
  • Workup and product: extract with dichloromethane, filter, evaporate solvent; obtained ~1.6 g of a pale yellow oily liquid consistent with acetic anhydride; test with water showed a denser-than-water layer and hydrolysis to acetic acid, confirming product identity.
  • Conclusion: acetic anhydride can be produced from NaOAc and NO2, but the method is not viable due to toxicity and low yield; nevertheless, the legend is confirmed and the experiment was educational.

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