tags
calcium acetatebenzoicbenzoldehydebenzoic acidketoneformiccalcium saltcarboxylicaldehydeaceticacetoneacetophenonecalcium propionatecalcium saltscalciumcalcium benzoate

video tutorial Prepare aromatic ketones from calcium benzoate

  • Objective: explore forming mixed ketones by heating calcium salts of benzoic acid with another carboxylic acid (formic/acetic) to make ketones such as propiophenone and acetophenone.
  • Experiment 1 (benzoic acid + formic acid): converted to calcium salts; attempted distillation to benzaldehyde but aldehyde oxidized to benzoic acid in air; reaction failed without inert atmosphere.
  • Experiment 2 (benzoic acid + acetic acid): produced acetophenone as the main product, with acetone and benzophenone as byproducts from self-reaction of calcium salts.
  • Isolated products: about 6 g acetophenone (roughly 12% yield relative to benzoic acid) and about 10 mL acetone; benzophenone residue was impure and not fully distilled.
  • Purification: organic layer separated; fractional distillation indicated acetone (bp ~60 C) and acetophenone (bp ~200 C); benzophenone high bp not distilled under the setup.
  • Notes: previous experiment using calcium propionate and calcium benzoate gave better results; this approach is less efficient but offers a route when Friedel–Crafts reagents are unavailable.
  • Tips for improvement: dry reagents, grind to fine powders, apply high heat, consider smaller scale or inert atmosphere for aldehyde formation, and optimize distillation.

more