Conversion of 1-tetralone over HY zeolite: An indicator of the extent of hydrogen transfer

Abstract

The conversion of pure 1-tetralone and its mixtures with n-decane, decalin, tetralin, or 1,5-dimethyl tetralin (DMT) has been investigated over HY zeolite. The dominant reactions undergone by 1-tetralone are the dehydrogenation to 1-naphthol and the subsequent isomerization to 2-naphthol. In the presence of hydrocarbons, the hydrogen transfer/dehydration of naphthols is accelerated, and naphthalene is formed in different amounts, depending on the nature of the co-fed hydrocarbon. In this contribution, it is demonstrated how the product distribution from the tetralone conversion can be used as an indicator of the hydrogen transfer ability of a particular hydrocarbon, or mixture of hydrocarbons. The relative order of hydrogen transfer ability of the various hydrogen donating compounds, as inferred from the naphthalene-to-naphthol product ratio, is DMT > tetralin ≈ decalin > n-decane. This trend agrees well with the hydride dissociation energy of individual donors calculated by DFT. © 2010 Elsevier B.V. All rights reserved.