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

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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.

Keywords: ACETALIZATION; ATR-IR SPECTROSCOPY; ATTENUATED TOTAL REFLECTION INFRARED SPECTROSCOPY; CO2-EXPANDED ALCOHOLS; CYCLOHEXANONE; GE CRYSTAL; HIGH PRESSURE; ZNSE CRYSTAL

Document Type: Research Article

DOI: http://dx.doi.org/10.1366/000370209789379312

Affiliations: 1: Research Fellow of the Japan Society for the Promotion of Science; Institute for Chemical and Bioengineering, Department of Chemistry and Applied Biosciences, ETH Zurich, Hönggerberg, HCI, CH-8093 Zurich, Switzerland 2: Institute for Chemical and Bioengineering, Department of Chemistry and Applied Biosciences, ETH Zurich, Hönggerberg, HCI, CH-8093 Zurich, Switzerland

Publication date: September 1, 2009

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