Formula C3H6S Appearance Brown liquid | Molar mass 74.14 g/mol ChemSpider ID 557043 | |
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Thioacetone is an organosulfur compound with the chemical formula (CH3)2CS. It is a lightly studied compound. The compound has been isolated as an orange or brown liquid at low temperatures. Above -20 °C, thioacetone readily converts to a polymer and a trimer.
Contents
Preparation
Thioacetone is usually obtained by cracking the cyclic trimer [(CH3)2CS]3. The trimer is prepared by pyrolysis of allyl isopropyl sulfide or by treating acetone with hydrogen sulfide in the presence of Lewis acids. The trimer cracks at 500-600 °C to give the thione.
Thioacetone trimer
The trimer of thioacetone is a white or colorless compound with a melting point of 24 °C, near room temperature. It also has a disagreeable odor. It is also known as 1,1,3,3,5,5-hexamethyltrithiane. Taste at 0.35-0.50 ppm is recommended, its organoleptic characteristics are described as berry; earthy; minty; citrus; sulfurous.
Odor
Thioacetone has a foul odor. Like many low molecular weight organosulfur compounds, the smell is potent. And like such compounds it can be detected at high dilution. In 1889, an attempt to distill the chemical in the German city of Freiburg im Breisgau was followed by cases of vomiting, nausea and unconsciousness in an area of 0.75 kilometres (0.47 mi) around the laboratory due to the smell. The soap manufacturer Whitehall Soap Works later noted in an 1890 report that dilution seemed to make the smell worse and described the smell as "fearful". Thioacetone is considered a dangerous chemical due to its extremely foul odor and ability to render people unconscious, induce vomiting, and be detected over long distances.
