Selective Liquid-Phase Hydrogenation of a Nitro Group in Substituted Nitrobenzenes over Au/Al2O3 Catalyst in a Packed-Bed Flow Reactor
Full article
| Общее |
Language:
Английский,
Genre:
Full article,
Status:
Published,
Source type:
Original
|
| Journal |
ChemPlusChem
ISSN: 2192-6506
|
| Output data |
Year: 2015,
Volume: 80,
Number: 12,
Pages: 1741 - 1749
Pages count
: 9
DOI:
10.1002/cplu.201500310
|
| Tags |
gold, hydrogenation, nitrobenzenes, supported catalysts, three-phase flow reactor |
| Authors |
Nuzhdin Alexey L.
1
,
Moroz Boris L.
1,2
,
Bukhtiyarova Galina A.
1
,
Reshetnikov Sergey I.
1
,
Pyrjaev Pavel A.
1
,
Aleksandrov Pavel V.
1
,
Bukhtiyarov Valerii I.
1,2
|
| Affiliations |
| 1 |
Boreskov Institute of Catalysis 5, Prospect Akademika Lavrentieva 5, 630090 Novosibirsk (Russia)
|
| 2 |
Novosibirsk State University 2, Pirogova Street, 630090 Novosibirsk (Russia)
|
|
Funding (2)
|
1
|
Council for Grants of the President of the Russian Federation
|
НШ-5340.2014.3
|
|
2
|
Russian Foundation for Basic Research
|
13-03-12178
|
A series of substituted nitrobenzenes with the general formula XC6H4NO2 (X=Cl, CH=CH2, or C(O)CH3) dissolved in toluenewere reduced with hydrogen over the 1.9% Au/Al2O3 catalyst at 60–1108C and 10–20 bar in a three-phase packed-bed reactor operating in up-flow mode. Under these conditions, hydrogenation of isomeric ClC6H4NO2 gives exclusively chloroanilines. Hydrogenation of 3-CH2CHC6H4NO2 and 4-CH3C(O)C6H4NO2 leads to the formation of
3-CH2CHC6H4NH2 and 4-CH3C(O)C6H4NH2 with selectivities of up to 93 and 97% at substrate conversions of 98 and 100%, respectively. Smooth catalyst deactivation was observed regardless of which substituted nitrobenzene was taken for hydrogenation. According to the results obtained by temperature-programmed oxidation of the spent catalyst, a carbonaceous deposit formed that might block the catalyst surface. Almost complete regeneration of
the supported gold catalyst with retention of its high selectivity to hydrogenation of a nitro group was achieved in a flow of air at temperatures up to 400 8C to eliminate carbonaceous deposits.