Abstract
When solid-state rhenium sulfide clusters with an octahedral metal framework are treated in a hydrogen stream above 300 °C, a catalytic activity for condensation of butylamine to yield N-butylidenebutylamine develops. Primary amines such as ethylamine, pentylamine, and hexylamine are also converted to the corresponding N-alkylidenealkylamines. Secondary amines such as diethylamine, dipropylamine, and dibutylamine are dehydrogenated to the corresponding N-alkylidenealkylamines. When triethylamine is allowed to react, dealkylation proceeds to yield diethylamine and its dehydrogenated product N-ethylideneethylamine. Trimethylamine is also dealkylated to dimethylamine. This series of catalytic behavior is the same as that of palladium and platinum metals. The similarity in selectivity is attributable to the rhenium atom that accepts electrons from the sulfur ligands leading to isoelectronic with the platinum group metals.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J.-C. P. Gabriel, K. Boubekeur, S. Uriel, and P. Batail (2001). Chem. Rev. 101, 2037.
Y. Sasaki (2005). J. Nucl. Radiochem. Sci. 6, 145.
S. Kamiguchi, S. Nagashima, and T. Chihara (2007). Chem. Lett. 36, 1340.
N. Yoshimura, I. Moritani, T. Shimamura, and S. Murahashi (1973). J. Am. Chem. Soc. 95, 3038.
A. Miyazawa, K. Saitou, K. Tanaka, T. M. Gädda, M. Tashiro, G. K. S. Prakash, and G. A. Olah (2006). Tetrahedron Lett. 47, 1437.
B.-T. Khai, C. Concilio, and G. Porzi (1981). J. Organomet. Chem. 208, 249.
X.-Q. Wei, W. Chen, D. Morales-Morales, and C. M. Jensen (2002). J. Mol. Catal. A 189, 119.
S. Murahashi and T. Yano (1979). J. Chem. Soc. Chem. Commun. 270.
W. Bronger, H.-J. Miessen, R. Neugröschel, D. Schmitz, and M. Spangenberg (1985). Z. Anorg. Allg. Chem. 525, 41.
W. Bronger, M. Loevenich, D. Schmitz, and T. Schuster (1990). Z. Anorg. Allg. Chem. 587, 91.
W. Bronger, H.-J. Miessen, and D. Schmitz (1983). J. Less Common Met. 95, 275.
S. Kamiguchi, M. Noda, Y. Miyagishi, S. Nishida, M. Kodomari, and T. Chihara (2003). J. Mol. Catal. A 195, 159.
J. Ruixia, X. Zaiku, Z. Chengfang, and C. Qingling (2003). Appl. Catal. A 250, 209.
J. A. Ballantine, J. H. Purnell, M. Rayanakorn, K. J. Williams, and J. M. Thomas (1985). J. Mol. Catal. 30, 373.
M. Hronec, Z. Cvengrošová, and J. Čejka (2003). Appl. Catal. A 255, 197.
C. F. Winans and H. Adkins (1932). J. Am. Chem. Soc. 54, 306.
S. Ogasawara, M. Takagawa, and K. Takahashi (1973). J. Catal. 29, 67.
E. P. Parry (1963). J. Catal. 2, 371.
T. R. Hughes and H. M. White (1967). J. Phys. Chem. 71, 2192.
H. Miura, T. Narita, M. Haruta, and K. Sugiyama (1985). Bull. Chem. Soc. Jpn. 58, 1043.
R. B. Levy and M. Boudart (1973). Science 181, 547.
R. Arratia-Pérez and L. Hernández-Acevedo (1999). J. Chem. Phys. 110, 2529.
S. Kamiguchi, S. Nishida, M. Kodomari, and T. Chihara (2005). J. Cluster Sci. 16, 77.
C. M. Fang, G. A. Wiegers, C. Haas, and R. A. de Groot (1997). J. Phys. Condens. Matter. 9, 4411.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kamiguchi, S., Ikeda, N., Nagashima, S. et al. Catalytic Condensation of Primary Amines, Dehydrogenation of Secondary Amines, and Dealkylation of Tertiary Amines over Solid-State Rhenium Sulfide Clusters with an Octahedral Metal Framework. J Clust Sci 20, 683–693 (2009). https://doi.org/10.1007/s10876-009-0271-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10876-009-0271-4