FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol

Hiessl R, Hennecke L, Plass C, Kleber J, Wahlefeld S, Otter R, Gröger H, Liese A (2020)
ANALYTICAL METHODS 12(24): 3137-3144.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Hiessl, Robert; Hennecke, Leon; Plass, CarmenUniBi; Kleber, Joscha; Wahlefeld, Stefan; Otter, Rainer; Gröger, HaraldUniBi; Liese, Andreas
Abstract / Bemerkung
In this study, an inline analytical method was designed and applied in process characterisation and development. The model reaction is the two-step diesterification of 3-methylphthalic anhydride with 2-ethylhexanol consisting of alcoholysis as the first step, followed by an acid-catalysed, second esterification step leading to the corresponding diester. The final product is a potential, alternative plasticiser. For the inline measurements, attenuated total reflection Fourier transformed infrared spectroscopy (ATR-FTIR) was implemented. In order to evaluate the spectra recorded during the reaction, a chemometric model was established. In this work, Indirect Hard Modeling (IHM), a non-linear modeling approach was employed. The respective model was calibrated by using offline samples analysed with gas (GC) and liquid chromatography (HPLC). After successful validation of the chemometric model, the inline measurements were utilized for reaction characterisation. The acid-catalysed, second esterification step was identified as the limiting reaction step. From batch reactions conducted at different temperatures, the energy of activation of this step was determined to be 79.5 kJ mol(-1). Additionally, kinetics were shown to follow a pseudo-first order with respect to the monoester formation and a kinetic model was established. The model was validated in simulations with changed reaction conditions.
Erscheinungsjahr
2020
Zeitschriftentitel
ANALYTICAL METHODS
Band
12
Ausgabe
24
Seite(n)
3137-3144
ISSN
1759-9660
eISSN
1759-9679
Page URI
https://pub.uni-bielefeld.de/record/2944769

Zitieren

Hiessl R, Hennecke L, Plass C, et al. FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol. ANALYTICAL METHODS. 2020;12(24):3137-3144.
Hiessl, R., Hennecke, L., Plass, C., Kleber, J., Wahlefeld, S., Otter, R., Gröger, H., et al. (2020). FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol. ANALYTICAL METHODS, 12(24), 3137-3144. doi:10.1039/d0ay00686f
Hiessl, R., Hennecke, L., Plass, C., Kleber, J., Wahlefeld, S., Otter, R., Gröger, H., and Liese, A. (2020). FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol. ANALYTICAL METHODS 12, 3137-3144.
Hiessl, R., et al., 2020. FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol. ANALYTICAL METHODS, 12(24), p 3137-3144.
R. Hiessl, et al., “FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol”, ANALYTICAL METHODS, vol. 12, 2020, pp. 3137-3144.
Hiessl, R., Hennecke, L., Plass, C., Kleber, J., Wahlefeld, S., Otter, R., Gröger, H., Liese, A.: FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol. ANALYTICAL METHODS. 12, 3137-3144 (2020).
Hiessl, Robert, Hennecke, Leon, Plass, Carmen, Kleber, Joscha, Wahlefeld, Stefan, Otter, Rainer, Gröger, Harald, and Liese, Andreas. “FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol”. ANALYTICAL METHODS 12.24 (2020): 3137-3144.

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