UNEXPECTEDLY RAPID ESTERIFICATION OF NITRITE APPLIED TO DETERMINATION OF NITRITE IN WATER

Nitrite is converted to an alkyl nitrite by passing an acidified solution through a bed of packed beads (XAD-2) coated with 1-decanol, the latter acting both as a reactant and as an extractant. The reaction proceeds by rate limited diffusion of nitrous acid into the alkanol phase where it is rapidly esterified. Esterification by this pathway is quite rapid (obsd t// one-half equals 11 s) and efficient. The product, decyl nitrite, is retained in the alkanol phase where it is reistant to hydrolysis because of the limited solubility of water in the alkanol phase. Under optimized conditions, 68% of the nitrite present in the original water solution was retained on the column as decyl nitrite. Decyl nitrite was eluted from the column with acetone and then converted to a highly colored azo dye by sequential reaction with sulfanilamide and N-(1-naphthyl)ethylenediamine.