The butoxylation of dodecylamine: reaction mechanism and kinetics

Pia Müller, R.D.E. Krösschell, Wyatt Winkenwerder, John van der Schaaf (Corresponding author)

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Abstract

The reaction mechanism and kinetics of the butoxylation of dodecylamine were investigated experimentally using a semi-batch, fully liquid process at temperatures ranging from 120 °C to 150 °C and varying stoichiometric ratios of the reactants. In addition, the catalytic effect of adding 1-3%mol of twelve different functional organic species containing hydroxyl, aldehyde, amine, and/or amide functional groups was studied. It was found that only proton donating groups increase the observed reaction rate. In particular hydroxyl groups in combination with an amine group resulted in a strong acceleration of the reaction. Since the reaction intermediates mono-and dibutoxylated amines have this combination, an auto-catalytic reaction mechanism and corresponding rate law are proposed. The kinetic constants were fitted to the experimental data as a function of temperature, following an Arrhenius type of dependency. The results from the model describe the experimental data with 95% accuracy. Moreover, the results show that the butoxylation of dodecylamine, as a model reactant for a short substituted ethylene oxide, with fatty amines, follows the same mechanism and has similar kinetics as epoxide hardening reactions with amines.
Original languageEnglish
Article number122939
Number of pages9
JournalChemical Engineering Journal
Volume382
DOIs
Publication statusPublished - 15 Feb 2020

Funding

This research was carried out within the HighSinc program – a joint development between Nouryon Specialty Chemicals and the Department of Chemical Engineering and Chemistry from Eindhoven University of Technology.

FundersFunder number
Eindhoven University of Technology
Monash University

    Keywords

    • Alkoxylation
    • Auto-catalysis
    • Mechanistic study
    • Non-ionic surfactants
    • Reaction modelling

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