Journal
JOURNAL OF CATALYSIS
Volume 269, Issue 1, Pages 131-139Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2009.10.024
Keywords
Chloronitrobenzene; Chloroaniline; Hydrogenation; Carbon dioxide; Intermolecular interaction
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Funding
- One Hundred Talent Program of CAS [NSFC 20873139, KJCX2, YW.H16]
- Japan Society for the Promotion of Science [18360378]
- CAS-JSPS [GJHZ05]
- Global COE (Center of Excellence) of Hokkaido University
- Grants-in-Aid for Scientific Research [22360327] Funding Source: KAKEN
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The hydrogenation of chloronitrobenzene to chloroaniline was investigated over Ni/TiO2 at 35 degrees C in supercritical CO2 (scCO(2)), ethanol, and n-hexane. The reaction rate followed the order of scCO(2) > n-hexane > ethanol. In scCO(2), the selectivity to chloroaniline and to aniline over Ni/TiO2 were 97-99.5% and < 1%, respectively, in the conversion range of 9-100%. The high chemoselectivity to chloroaniline cannot be achieved over Ni/TiO2 in ethanol and n-hexane. In situ high-pressure Fourier transform infrared measurements were made to study the molecular interactions of CO2 with the following reactant and reaction intermediates: chloronitrobenzene, chloronitrosobenzene, and N-chlorophenylhydroxylamine. The molecular interaction modifies the reactivity of each species and accordingly the reaction rate and the selectivity. The influence of Cl substituent on the interaction modes of CO2 with these reacting species is discussed. Possible reaction pathways for the hydrogenation of chloronitrobenzene in scCO(2) over Ni/TiO2 are also proposed. (c) 2009 Elsevier Inc. All rights reserved
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