The reaction of sodium on acetic anhydride

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Virginia Agricultural and Mechanical College and Polytechnic Institute
  1. Improved conditions for the reaction of sodium on acetic anhydride were used.
  2. From the products of this reaction sodium acetate, diacetyl, and resin were found.
  3. Negative results for the formation of vinyl acetate and ethylidene diacetate were obtained.
  4. The small amount of hydrogen produced in this reaction is believed to correspond to the presence of acetic acid as an impurity. (If it represents acetic acid then the acetic anhydride used contained from 0.02% to 0.07% acetic acid. If it were a product of the reaction then it represents a 0.04% to 0.12% enolization of the acetic anhydride in the reaction.)
  5. A method for preparing practically 100% acetic anhydride was devised and checked.
  6. The resin formed in this reaction is believed to be polymerized diacetyl built up from its dimer, dimethyl quinogen.
  7. A possible formation of the resin is proposed.
  8. The reaction of sodium on acetic anhydride at room temperature seems to proceed in the same way as at elevated temperatures only much slower with the production of a smaller percentage of resin. Contrary to Kalmin (1) no acetone was found in the products of the room temperature reaction.