Date of Award
Union College Only
Bachelor of Science
The products of the ozonolysis of tetramethylethylene (TME) in the gas phase was studied. Reactions were run at concentrations between 10 and 400ppm TME and lower concentrations of ozone. The reactions were run at room temperature and atmospheric pressure. Gaseous products were studies by gas chromatography, mass spectrometry and HPLC analysis, the latter using 2, 4-dinitrophenylhydrazine derivatives of carbonyl products. Ozone concentrations and the determination of possible peroxidic products was accomplished by measuring the absorbance of a buffered KI solution (352 nm) after reaction with a known volume of gas. The possibility of acetone/ ozone and TME/ peroxides reactions were experimentally determined. Significant amounts of acetone and formaldehyde were detected. Traces of methylglyoxal were also found. Methyl acetate, and ethyl acetate, acetyldehyde, glyoxal, and dimethyl glyoxal were not detected in any significant amounts. Carbon dioxide, carbon monoxide, methanol, acetic acid, and formic acid were all determined to be undetectable with the methods used. At initial TME concentrations of 100ppm, acetone appeared with nearly a 1:1 ratio with TME consumed. At TME concentrations of 400ppm a 50% increase in yield of acetone was detected. The yield of formaldehyde to TME consumed was approximately 1:5 with slight decrease in the yield of formaldehyde with increasing concentrations. A variation of the Criegee mechanism of ozonolysis was a better explanation for the results observed than the O’Neal-Blumstein mechanism.
DeAngelo, Anthony R., "The products of the gas phase ozonolysis of tetramethylethylene" (1983). Honors Theses. 1887.