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Nitrosamine formation from ternary nitrogen compounds

R N Loeppky, W Tomasik, J R Outram

    IARC Scientific Publications
    |January 1, 1982
    PubMed
    Summary
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    Heating pyrrolidine amides with sodium nitrite forms N-nitrosopyrrolidines (NPYR). Polyol solvents like ethylene glycol enhance reaction rates and yields, suggesting a novel ester-mediated nitrosation pathway for tertiary amine formation.

    Area of Science:

    • Organic Chemistry
    • Chemical Kinetics
    • Nitrosamine Formation

    Background:

    • Pyrrolidine amides can form N-nitrosamines (NPYR) upon heating with sodium nitrite.
    • Solvent choice significantly impacts reaction kinetics and yields in nitrosamine formation.

    Purpose of the Study:

    • To investigate the mechanism of N-nitrosopyrrolidine (NPYR) formation from pyrrolidine amides and sodium nitrite.
    • To explore the role of polyol solvents in enhancing nitrosation reactions.
    • To elucidate a novel mechanism for tertiary amine nitrosation.

    Main Methods:

    • Heating pyrrolidine amides with sodium nitrite in various solvents, including polyols (ethylene glycol, glycerine).
    • Kinetic analysis to determine reaction rates and identify intermediates.

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  • Characterization of nitrosamine products, including N-nitrosodiethanolamine (NDELA) and N-nitrosodimethylamine (NDMA).

    • Main Results:

    • Polyol solvents (ethylene glycol, glycerine) increased both the rate and yield of NPYR formation.
    • Kinetic data supports a mechanism involving polyol ester formation, followed by reaction with sodium nitrite to form nitrite esters, which then nitrosate the amine.
    • Heating LDEA with sodium nitrite yielded high NDELA amounts rapidly, consistent with the proposed mechanism.
    • 2-N,N-dimethylaminomethylpyrrole reacted rapidly with nitrous acid to yield NDMA, suggesting a new tertiary amine nitrosation pathway.

    Conclusions:

    • A novel ester-mediated mechanism for nitrosation of pyrrolidine amides in polyol solvents has been proposed.
    • This mechanism explains the enhanced reaction rates and yields observed.
    • The rapid nitrosation of 2-N,N-dimethylaminomethylpyrrole indicates a new pathway for tertiary amine nitrosation.