Abstract
The ozonolysis of 1-decene (1) was performed in a falling film microreactor and in a semibatch reactor using different solvents (CH2Cl2, CH3OH, or a mixture of both). The main products of ozonolysis were 3-octyl-1,2,4-trioxolane (7) in CH2Cl2 and 1-hydroperoxy-1-methoxynonane (8) in CH3OH or in a CH2Cl2/CH3OH mixture. In both cases the selectivities were higher than 70% and almost independent of 1-decene conversion and reaction temperature. The ozonolysis proceeds mainly via the cleavage of the primary ozonide into the long-chain carbonyl oxide (6) and formaldehyde (4). Besides off-line analysis in situ ATR-FTIR spectroscopic measurements using a diamond ATR probe were applied to follow the reaction progress. Integral intensities of characteristic IR bands correlate well with quantitative results obtained from gas chromatography/high-performance liquid chromatography analysis. Thus, in situ ATR proved to be a suitable method for fast and real-time monitoring of liquid-phase reactions even in the presence of unstable or explosive intermediates like ozonides and/or hydroperoxides.
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