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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 8 Issue 2 (2003) pp 112-115

Simple Derivation of the pH at Which the Rate of Nitrosation of a Secondary Amine Is Maximized

Michael D. Gernon* and Christine Trumpfheller

Atofina Chemicals, King of Prussia R&D Center, King of Prussia, PA 19406,
Received October 14, 2002. Accepted January 3, 2003.

Published online: 3 February 2003

Abstract. The rate of nitrosation of a simple secondary amine in aqueous solution is greatest at the pH that maximizes the total solution content of nitrous acid and free-base (unprotonated) secondary amine. The value of this pH, designated as pHmax,can be easily derived through consideration of the equilibria involved. The derivation of pHmax as given demonstrates that it is possible to predict from first principles some significant aspects of nitrosation kinetics. The importance of understanding pHmax with respect to promoting or avoiding nitrosamine formation is discussed.

Key Words:  In the Classroom; physical chemistry; kinetics; Nitrosamine; N-nitrosoamine; nitrosation; nitrosating agent; nitrosamine control

(*) Corresponding author. (E-mail:

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Issue date: April 1, 2003

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