Date of Award
Master of Science
This work was begun in an attempt to study further the preparation of thianthrene from 2-dichlorobenzene and alkali sulfides. g_-Dichlorobenzene is a liquid by-product in the preparation of its solid isomer, E-dichlorobenzene, which is used extensively for controlling moths and peach tree borers. The study of the preparation of thianthrene from the liquid isomer was undertaken because the preparation might develop into a possible use for the large quantities available.
Thianthrene might be made from 2-dibromo- and 2-diiodo-benzene but these are not as cheap or as easily obtained as the dichloro derivative and were not used in this study various sulfides and hydrosulfides can be used for the preparation but again sodium sulfide and hydrosulfide were choices made because they are cheap and readily obtainable. Various runs were made with these materials in combination with other reagents in an attempt to prepare thianthrene in fair yield. The best results were obtained using equimolar quantities of 2-dichlorobenzene and sodium hydrosulfide in water solution with a half molar quantity of calcium hydroxide. The calcium hydroxide may be added to the solution contains sodium sulfide or sodium hydroxide before saturating it with hydrogen sulfide to prepare the sodium hydrosulfide, or after it is saturated. If the calcium hydroxide is added ahead of the hydrogen sulfide, the solution should not be agitated very much since if the hydrogen sulfide comes into intimate contact with the calcium hydroxide precipitate it may be converted partially to the sulfide and excess sulfide has been found to cut the yield of thianthrene.
Talley, Eugene Alton, "Preparation of thianthrene" (1938). Master's Theses. 1242.