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Applied Spectroscopy

Applied Spectroscopy

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  • Vol. 63, Iss. 9 — Sep. 1, 2009
  • pp: 1008–1014

Tracing the Acetalization of Cyclohexanone in CO2-Expanded Alcohols by Attenuated Total Reflection Infrared Spectroscopy

Tsunetake Seki, Jean-Michel Andanson, Fabian Jutz, and Alfons Baiker

Applied Spectroscopy, Vol. 63, Issue 9, pp. 1008-1014 (2009)


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Abstract

The CO2-catalyzed acetalization is regarded as a promising alternative to the conventional acid-catalyzed method from a viewpoint of green chemistry (C. A. Eckert et al., Ind. Eng. Chem. Res. 43, 2605 (2004)). We have applied in situ attenuated total reflection infrared (ATR-IR) spectroscopy for elucidating and monitoring the acetalization of cyclohexanone in CO2-expanded ethylene glycol and methanol at 50 °C and 3 MPa. The ATR-IR spectra of the reaction mixtures periodically recorded with a ZnSe crystal demonstrate that ATR-IR spectroscopy is a practical tool for tracing the kinetics of acetalizations in situ. In addition, the rate of CO2 dissolution as well as CO2 solubility into the cyclohexanone–alcohol mixtures could be evaluated from the CO23-antisymmetric stretching band. The ZnSe ATR crystal, however, was corroded during longer use under the acidic conditions realized by the dissolution of CO2 in the alcohols. In contrast, the corrosion did not occur when a Ge crystal was used instead of a ZnSe crystal, and therefore the application of a Ge ATR crystal is recommended for continuous long-term experiments with these media.

Citation
Tsunetake Seki, Jean-Michel Andanson, Fabian Jutz, and Alfons Baiker, "Tracing the Acetalization of Cyclohexanone in CO2-Expanded Alcohols by Attenuated Total Reflection Infrared Spectroscopy," Appl. Spectrosc. 63, 1008-1014 (2009)
http://www.opticsinfobase.org/as/abstract.cfm?URI=as-63-9-1008

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