Highly selective oxidation of toluene using air over [Fe(III)TPP]Cl supported on chitosan

Guan Huang; Chun-Cai Cai; Jin Luo; Hong Zhou; Yong-An Guo; Shang-Yue Liu
March 2008
Canadian Journal of Chemistry;Mar2008, Vol. 86 Issue 3, p199
Academic Journal
The highly selective catalytic oxidation of toluene with air to benzaldehyde and benzyl alcohol in the liquid phase has been studied with the use of iron tetraphenylporphyrin (Fe TPP) supported on chitosan (CTS), (Fe TPP/CTS). The rates of toluene conversion and selectivity (aldehyde + alcohol) were subject to the reaction temperature, air pressure, and amount of iron tetraphenylporphyrin. By the use of the Fe TPP/CTS, containing 2 mg of iron tetraphenylporphyrin as catalyst, toluene oxidation with air under the optimum conditions of 190 °C and 0.6 MPa produced benzaldehyde and benzyl alcohol at 90% selectivity and 5.4% conversion of toluene, the mole turnover of the catalyst was about 6 × 106, and it could be reused efficiently for one more time. It is suggested that the amine groups (–NH2) on the chitosan chain act as a key assistor to the catalysis of Fe TPP for toluene oxidation. Compared with the conventional method of synthesizing benzaldehyde and benzyl alcohol, the new method has the advantages of reduced environmental pollution, higher selectivity for the two main products, and easy recovery of the catalyst.Key words: chitosan-supported iron porphyrin, catalysis, toluene oxidation, benzaldehyde, benzyl alcohol. Utilisant un catalyseur formé de tétraphénylporphyrine-fer (TPP Fe) déposé sur du chitosane (CTS), (TPP Fe/CTS), on a étudié l’oxydation catalytique hautement sélective en phase liquide du toluène par l’air qui conduit à la formation de benzaldéhyde et d’alcool benzylique. Les vitesses de conversion du toluène et la sélectivité (aldéhyde + alcool) varient avec la température de la réaction, la pression de l’air et la quantité de tétraphénylporphyrine-fer. Lorsqu’on utilise du TPP Fe/CTS contenant 2 mg de tétraphénylporphyrine-fer comme catalyseur, dans les conditions optimales pour l’oxydation du toluène par l’air de 190 °C et de 0,6 MPa, il y formation de benzaldéhyde et l’alcool benzylique avec une sélectivité de 90%, une conversion de 5,4% du toluène et une réutilisation molaire interne du catalyseur d’environ 6 × 106 qui pouvait être réutilisé efficacement au moins une fois. On croit que les groupes amino (–NH2) de la chaîne du chitosane sont des assistants clés pour la catalyse de l’oxydation du toluène par la TPP Fe. Par comparaison avec la méthode conventionnelle de synthèse du benzaldéhyde et de l’alcool benzylique, la nouvelle méthode présente des avantages en raison d’une réduction de la pollution environnementale, d’une grande sélectivité pour les deux produits principaux et de la facilité de récupération du catalyseur.Mots-clés : porphyrine-fer déposée sur du chitosane, catalyseur, oxydation du toluène, benzaldéhyde, alcool benzylique.[Traduit par la Rédaction]


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