# Do alkylhydroxylamines form N-nitrosamines?

Usual secondary amines can form N-nitrosamines with nitrosating agents, e.g., $$\ce{KNO2}$$, and are therefore forbidden in metalworking fluids.

But can alkylhydroxylamines form N-nitrosamines with nitrosating agents in metalworking fluids?

I assume the basicity of the N-atom in alkylhydroxylamines is lowered by the inductive effect and the mesomeric effect. But is this enough to prevent formation of N-nitrosamines?

Yes they can in acidic solutions according to the abstract of this paper$$^{[1]}$$:
O-Alkylhydroxylamines react with nitrous acid with a rate law $$v = k_2\ce{[R^1NH2^+OR^2][HNO2]}$$; the mechanism involves electrophilic nitrosation at the nitrogen atom of the free base. At acid concentrations below $$\pu{2M}$$-per-chloric acid, hydroxylamine and N-methylhydroxylamine react with nitrous acid by an acid-catalysed mechanism with a rate law $$v = k_3\ce{[RNH2^+OH][HNO2]}h_\circ$$; this involves initial nitrosation at the oxygen atom of the conjugate acid, followed by migration of the nitrosonium ion to the nitrogen. At higher acidities the O-nitrosation can be reversed, and the migration of the nitrosonium ion becomes the rate-determining stage.