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Hazard Predictions

• Flammable: Reaction products may be flammable
• Generates gas: Reaction liberates gaseous products and may cause pressurization
• Generates heat: Exothermic reaction at ambient temperatures (releases heat)
• Toxic: Reaction products may be toxic

There is a variety of reactivity with this combination, depending on whether metal hydrides or metal alkyl reagents are involved.

No evidence was found for an adverse reaction between quaternary ammonium or phosphonium ions (i.e. those with four carbon groups on the nitrogen or phosphorus) and hydrides; in fact several complex hydrides include quaternary ammonium or phosphonium ions as counterions (Eggeman, T. 2001. Hydrides. In Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. (Online)).

Methyllithium and phenyllithium can remove alkyl groups from quaternary ammonium ions (i.e. those with four carbon groups on the nitrogen) in a reaction called a Hofmann degradation. The products of the reaction are the free amine, an alkene (derived from the alkyl group removed from the ammonium ion), methane or benzene (depending on which organolithium reagent was used), and a lithium salt. The hydrocarbon products and the amine may be volatile and flammable, depending on the conditions (Wittig, G., Polster, R. Justus Liebigs Annalen der Chemie (1957), 612, 102-8).