Matrix-isolation pyrolysis investigation of mercapto-functionalized 1,3,4-thiadiazoles: thermal stability of thiadiazole lubricant additives†
Roland A. Fischer,Jens Müller
Physical Chemistry Chemical Physics Pub Date : 02/04/2005 00:00:00 , DOI:10.1039/B415019H
Abstract

A series of high-vacuum thermolysis experiments with alkyldithio thiadiazoles was performed between ambient temperature and 900 °C to investigate the thermal stability of thiadiazole type lubricant additives. The thermolysis products were trapped by matrix-isolation techniques and characterized by IR spectroscopy. Thermolysis of 2-(tert-butyldithio)-5-methyl-1,3,4-thiadiazole (TB1) gave 2-methylpropene, isothiocyanic acid (HNCS), 2-mercapto-5-methyl-1,3,4-thiadiazole (McMT), hydrogen cyanide (HCN), carbon disulfide (CS2), acetonitrile (CH3CN), and elemental sulfur Sx [x = (2), 4, 6, 8]. A decomposition mechanism is discussed explaining the temperature-dependent composition of product mixtures, and a general precursor concept for organosulfur type anti-wear additives is presented.

Graphical abstract: Matrix-isolation pyrolysis investigation of mercapto-functionalized 1,3,4-thiadiazoles: thermal stability of thiadiazole lubricant additives