Abstract
A chromium-incorporated microporous aluminophosphate, CrAPO-5, was tested as a catalyst for the oxidation of tetralin using either a combination of aldehyde and O2 (1 atm) or tert-butyl hydroperoxide as an oxidant system. The former resulted in significantly improved catalytic performance (69.6% yield to 1-tetralone) over the latter (38.5% yield to 1-tetralone) at 80 °C in 8 h, and conversion increased in the sequence of acetaldehyde≪isobutyl aldehyde<pivalaldehyde. CrAPO-5 also exhibited good activity and high selectivity (53.7% yield to 1-tetralone) after 24 h using pivalaldehyde and O2 at room temperature. Hot filtration and recycle experiments established that oxidation takes place mostly on Cr sites in CrAPO-5. A plausible reaction mechanism involving acylperoxy radicals and oxo-chromium(V) species on CrAPO-5 was proposed for the tetralin oxidation.
Similar content being viewed by others
References
J. Muzart, Bull. Soc. Chim., 65 (1986).
H. G. Franck and J. W. Stadelhofer, Industrial Aromatic Chemistry, Springer-Verlag, Berlin, 313 (1988).
G. A. Wachter, R. W. Hartman, T. Sergejew, G. L. Grun and D. Ledergerber, J. Med. Chem., 39, 834 (1996).
R. G. Tailleur, G. A. Salva and G. Garcia, Fuel, 88, 744 (2009).
J. Muzart, Tetrahedron Lett., 28, 2131 (1987).
J. Muzart, J. Chem. Rev., 92, 113 (1992).
J. Muzart and A. A. Nait, J. Mol. Catal., 92, 277 (1994).
S. L. H. Rebelo, M. M. Q. Simoes, M. P. M. S. Neves, A. M. S. Silva, P. Tagliatesta and J. A. S. Cavaleiro, J. Mol. Catal. A: Chem., 232, 135 (2005).
L. J. Csanyi, K. Jaky, Z. Kota and T. Pali, J. Mol. Catal. A: Chem., 209, 59 (2004).
Y. M. Chung, W. S. Ahn and P. K. Lim, J. Catal., 173, 210 (1998).
S. H. Cho, M. S. Cheong, K. D. Jung, C. S. Kim and S. H. Han, Appl. Catal. A: Gen., 267, 241 (2004).
S. Sithambaram, E. K. Nyutu and S. L. Suib, Appl. Catal. A: Gen., 348, 214 (2008).
X. F. X. Llabres, O. Casanova, R. G. Tailleur, H. Garcia and A. Corma, J. Catal., 255, 220 (2008).
J. Kim, S. Bhattacharjee, K. E. Jeong, S. Y. Jeong and W. S. Ahn, Chem. Commun., 3904 (2009).
S. Bhattacharjee, K. E. Jeong, S. Y. Jeong and W. S. Ahn, New J. Chem., 34, 156 (2010).
J. D. Chen and R. A. Sheldon., J. Catal., 153, 1 (1995).
H. E. B. Lempers and R. A. Sheldon, Appl. Catal. A: Gen., 143, 137 (1996).
P. Tian, Z. Liu, Z. Wu, L. Xu and Y. He, Catal. Today, 93, 735 (2004).
R. A. Shaikh, G. Chandrasekar, K. Biswas, J. S. Choi, W. J. Son, S. Y. Jeong and W. S. Ahn, Catal. Today, 132, 52 (2008).
O. B. Ryan, D. E. Akporiaya, R. H. Holm and M. Stocker, Stud. Surf. Sci. Catal., 108, 369 (1997).
S. E. Dapurkar, H. Kawanami, T. Yokoyama and Y. Ikushima, New J. Chem., 33, 538 (2009).
S. E. Dapurkar, H. Kawanami, T. Yokoyama and Y. Ikushima, Catal. Commun., 10, 1025 (2009).
S. K. Mohapatra, F. Hussain and P. Selvam, Catal. Lett., 85, 217 (2009).
A. Sakthivel, S. K. Badamali and P. Selvam, J. Catal., 80, 73 (2002).
Z. Lounis, A. Riahi, F. Djafri and J. Muzart, Appl. Catal. A: Gen., 309, 270 (2006).
B. M. Choudary, A. D. Prasad, V. Bhuma and V. Swapna, J. Org. Chem., 57, 5841 (1992).
S. K. Mohapatra and P. Selvam, J. Catal., 249, 394 (2007).
C. Mahendiran, P. Sangeetha, P. Vijayan, S. J. Sardhar and K. Shanthi, J. Mol. Catal. A: Chem., 275, 84 (2007).
R. A. Sheldon, J. Mol. Catal. A: Chem., 107, 75 (1996).
K. B. Sharpless and T. R. Verhoeven, Aldrichim. Acta., 12, 63 (1979).
J. Kim, S. Bhattacharjee, K. E. Jeong, S. Y. Jeong, M. Choi, R. Ryoo and W. S. Ahn, New J. Chem., 34, 2971 (2010).
A. Sakthivel, S. E. Dapurkar and P. Selvam, Catal. Lett., 77, 155 (2001).
P. Karandikar, M. A. Gashe, K. Vijayamohanan and A. Chandwadkar, J. Appl. Catal. A: Gen., 257, 133 (2004).
P. Aguirre, S. Zolezzi, J. Parada, E. Bunel, S. A. Moya and R. Sariego, Appl. Organometal. Chem., 20, 260 (2006).
S. I. Murahashi, T. Naota and N. Komiya, Tetrahedron Lett., 36, 8059 (1995).
M. M. Dell’Anna, P. Mastrorilli and C. F. Nobile, J. Mol. Catal. A: Chem., 130, 65 (1998).
T. Yamauchi and H. Nabu, US Patent, 4,283,352 (1981).
M. Martan, J. Manassen and D. Vofsi, Tetrahedron, 26, 3815 (1970).
Y. O. Moro, Catal. Today, 45, 3 (1998).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Bhattacharjee, S., Lee, YR. & Ahn, WS. Oxidation of tetralin to 1-tetralone over CrAPO-5. Korean J. Chem. Eng. 34, 701–705 (2017). https://doi.org/10.1007/s11814-016-0310-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11814-016-0310-4