p-Toluenesulfonamide for the environment

IUPAC Name: 4-Methylbenzenesulfonamide  
Molecular Formula: C7H9NO2S 
Molecular Weight: 171.21 g/mol 
EINECS: 200-741-1
Melting Point: 134-137 C(lit.)
Water Solubility: 0.32 g/100 mL (25 C) 
Index of Refraction: 1.564  
Molar Refractivity: 43.81 cm3  
Molar Volume: 134.6 cm3
Surface Tension: 46.3 dyne/cm  
Density: 1.271 g/cm3  
Flash Point: 148.6 C  
Enthalpy of Vaporization: 56.4 kJ/mol  
Boiling Point: 322.2 C at 760 mmHg  
CAS NO: 70-55-3

A novel 1:1 cocrystal between p-toluenesulfonamide and triphenylphosphine oxide has been prepared and structurally characterized. This 1:1 cocrystal was observed to form during solid state grinding experiments, with subsequent formation of a known 3:2 cocrystal in the presence of excess sulfonamide. Both cocrystals are stable in the solid state. 

The ternary phase diagram for the two coformers was constructed in two different solvents: acetonitrile and dichloromethane. Examination of these diagrams clarified solution crystallization of both the newly discovered 1:1 cocrystal and the previously reported 3:2 cocrystal, and identified regions of stability for each cocrystal in each solvent. The choice of solvent was found to have a significant effect on the position of the solid state regions within a cocrystal system.

p-Toluenesulfonamide's production and use in organic synthesis, as a fungicide and mildewicide in paints and coatings,and in plasticizers and resins may result in its release to the environment through various waste streams. It has been detected in drinking water, surface water, ground water and in the effluents from the non ferrous metals and the printing and publishing industries. If released to soil, p-toluenesulfonamide(CAS NO:70-55-3) should have high mobility. 

Volatilization of p-toluenesulfonamide should not be important from moist or dry soil surfaces. p-Toluenesulfonamide will not be susceptible to direct photolysis on soil surfaces based on its lack of absorption of light at wavelengths >290 nm. Anaerobic biodegradation of p-toluenesulfonamide in soil and water is not expected to be an important fate process according to a biodegradation study conducted in anaerobic aquifer slurries. The importance of aerobic biodegradation is unknown. 

However, the lack of biodegradation in the MITI test of the ortho isomer suggests that aerobic biodegradation of p-toluenesulfonamide may be slow. If released to water, p-toluenesulfonamide should not adsorb to suspended solids and sediment. p-Toluenesulfonamide will be essentially non-volatile from water surfaces. An estimated BCF value of 2.5 suggests that it will not bioconcentrate in aquatic organisms. If released to the atmosphere, p-toluenesulfonamide will exist as both a vapor and particulate in the ambient atmosphere. 

Vapor-phase p-toluenesulfonamide is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 13 days. Particulate-phase p-toluenesulfonamide may be physically removed from the air by wet and dry deposition.

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