Nitrosamine

The nitrosamines are insoluble in water, and the lower members are liquid at ordinary temperatures. The separation of an oily liquid when an aqueous solution of an amine salt is treated with sodium nitrite is therefore strong evidence that the amine is secondary. Diphenylnitrosoamine is selected as a preparation because it is a crystalline substance and is thus easier to manipulate on a small scale than one of the lower liquid members. For this preparation, a fairly pure (and therefore almost colourless) sample of diphenyl-amine should be used. Technical diphenylamine, which is almost black in colour, should not be employed. 

Reaction of Diphenylnitrosoamine. Carry out Liebermann s Nitroso Reaction as described for phenol (p. 340), but use about 0 05 g. of the nitrosamine instead of the one crystal of sodium nitrite, and finally add only 3-4 drops of sulphuric acid. The deep greenish-blue colour is obtained, becoming red on dilution and reverting to blue on being made alkaline. 

Note. The nitrosamines in Class (ii) do not give the Liebermann reaction. 

N-Nitrosodiethylamine. Add 36-5 g. (51-5 ml.) of diethylamine slowly to the calculated quantity of carefully standardised 5A-hydra chloric acid cooled in ice (1). Introduce the solution of the hydi ochloride into a solution of 39 g. of sodium nitrite (assumed to be of 90 per cent, purity) in 45 ml. of water contained in a 250 ml. distilling flask. Distil the mixture rapidly to dryness. Separate the yellow upper layer of the nitrosamine from the distillate saturate the aqueous layer with soUd potassium carbonate and remove the nitroso compound which separates and add it to the main product. Dry over anhydrous potassium carbonate and distil. Collect the diethylnitrosamine at 172-173-5°, The yield is 41 g. 

Reduction of a nitrosamine to a secondary amine. Proceed as for a nitro compound. Determine the solubility of the residue after evaporation of the ether and also its behaviour towards benzenesulphonyl (or p-toluenesulphonyl) chloride. 

N Nitroso amines are more often called nitrosamines and because many of them are potent carcinogens they have been the object of much investigation We encounter nitrosamines m the environment on a daily basis A few of these all of which are known carcinogens are... 

Nitrosamines are formed whenever nitrosating agents come m contact with secondary amines Indeed more nitrosamines are probably synthesized within our body than enter it... 

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