Pyrolytic behavior of simple chiral molecules: secondary aromatic alcohols

作者：Keheyan Yeghis^*

来源：Rendiconti Lincei-scienze Fisiche E Naturali, 2013, 24(3): 239-249.

DOI：10.1007/s12210-013-0243-3

• Chiral 1-phenylethanol enantiomers
• Pyrolysis-GC/MS
• Racemization
• Enantiomeric excess
• Catalysts

The present study relates to the problem of the thermal stability of simple chiral molecules. Rough estimates of the temperatures under which the chirality phenomenon could survive have been reported. The chiral molecules tested in the present study were 1-phenylethanol (PE) enantiomers [(S(-)- and R-(+)-], S-(-)-1-phenylpropanol [PPe] and S-(+)-trifluoro-1-phenylethanol. The pyrolysis of the above-mentioned chiral alcohols with and without catalysts at different temperatures (200-600 A degrees C) has been carried out. In the presence of catalysts the partial racemization (a parts per thousand currency sign20 %) and formation of products like styrene, acetophenone, benzaldehyde and chiral benzylic ethers have been detected in the case of PE. Without catalysts almost no racemization was observed and product formation was not appreciable. The kinetics of racemization has been calculated and a tentative mechanism has been proposed. A principal components analysis model was created using the results obtained with all catalysts at different temperatures and with the main products, i.e., acetophenone, dibenzylic ethers and styrene to discriminate the catalysts on the basis of their effects.

• 出版日期2013-9