Efficient reduction of nitroarenes using supercritical alcohols as a source of hydrogen in flow-type reactor in the presence of alumina

•Reduction of nitroarenes using sc alcohols as a source of hydrogen was studied.•Methanol was used as the reducing agent, the main reaction product was N,N-dimethylaniline.•The use of scCO2 co-solvent had a significant impact on the course of the reduction process.•Conditions for the reduction of ha...

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Bibliographic Details
Published in:The Journal of supercritical fluids 2014-02, Vol.86, p.137-144
Main Authors: Sivcev, V.P., Korchagina, D.V., Suslov, E.V., Volcho, K.P., Salakhutdinov, N.F., Anikeev, V.I.
Format: Article
Language:English
Subjects:
Alcohols
Alumina
Aluminum oxide
Aniline
Carbon dioxide
Conversion
Hydrogen transfer
Meerwein–Ponndorf–Verley reduction
Methyl alcohol
Nitrobenzene
Reactors
Reduction
Selectivity
Supercritical alcohols
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Summary:•Reduction of nitroarenes using sc alcohols as a source of hydrogen was studied.•Methanol was used as the reducing agent, the main reaction product was N,N-dimethylaniline.•The use of scCO2 co-solvent had a significant impact on the course of the reduction process.•Conditions for the reduction of halogenated nitroarenes into respective amines were found. Reduction of nitroarenes using supercritical alcohols as a source of hydrogen was studied in a flow reactor in the presence of alumina at temperatures 515–615K and residence times not exceeding 6min. In the reaction of nitrobenzene reduction by 4-methylpentan-2-ol in supercritical (sc) CO2, the selectivity for aniline reached 95% with a conversion of 71%. If methanol was used as the reducing agent, the main reaction product was N,N-dimethylaniline. It was shown that the use of scCO2 co-solvent had a significant impact on the course of the reduction process including secondary and side reactions. The conditions for the reduction of halogenated nitroarenes into respective amines with high conversion and nearly 100% selectivity almost without dehalogenation were found.
ISSN:0896-8446
1872-8162
DOI:10.1016/j.supflu.2013.12.012