Date on Master's Thesis/Doctoral Dissertation
College of Arts and Sciences
This problem originated in an attempt to make methyl glyoxal in quantity. Several methods of making methyl glyoxal are mentioned in the literature but in none of them is acetone used as a starting point. Since this seemed a new field it was decided to chlorinate acetone hoping to obtain some product which might be easily converted into methyl glyoxal. Technical acetone was purified and dry chlorine was passed through this warm acetone in the presence of sunlight. During the process three distinct steps were noticed in the reaction. The first step was completed in the first half hour. During this time the acetone was held at the temperature of a boiling water bath and the chlorine was rapidly absorbed with an evolution of hydrochloric acid. At the end of this time the second step in the process set in, which lasted for two hours. Throughout this period no hydrochloric acid was evolved. The chlorine seemed to be simply absorbed with a marked heat of reaction. During the first half hour of this period the water bath was retained, but after that it was noticed that the heat of reaction was sufficient to keep the temperature up to 80 degrees Celsius. This seemed to be the critical temperature for this step of the reaction, for whenever the temperature exceeded 80 degrees Celsius a violent reaction occurred with a flame. As the heat of reaction was so intense during this step it was frequently necessary to cool the reaction mixture.
Borries, Marie, "The chlorination of acetone." (1919). Electronic Theses and Dissertations. Paper 130.