Smith, Keith  ORCID: https://orcid.org/0000-0003-4838-5651, Ajarim, Mansour Dahish and El-Hiti, Gamal A.
2010.
Regioselective nitration of deactivated mono-substituted benzenes using acyl nitrates over reusable acidic zeolite catalysts.
Catalysis Letters
134
(3-4)
, pp. 270-278.
10.1007/s10562-009-0258-7
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Abstract
Nitration of benzonitrile was investigated using a nitric acid/acid anhydride/zeolite catalyst system under different reaction conditions. Trifluoroacetic and chloroacetic anhydrides were found to be the most active among the anhydrides tried. Also, zeolites Hβ and Fe3+β (Si/Al = 12.5) were found to be the most active catalysts. For example, nitration of benzonitrile with trifluoroacetyl nitrate under reflux conditions in dichloromethane gave 3- and 4-nitrobenzonitriles in quantitative yield, of which the para-isomer represented 24–28%. The yield of para-isomer was improved to 33% when passivated Hβ was used under similar reaction conditions. This is easily the most para-selective nitration of benzonitrile ever recorded. Also, no ortho-isomer was formed under the conditions tried. The zeolite can be easily recovered, regenerated by heating and reused up to six times to give results similar to those obtained with a fresh sample of the catalyst. The nitration system was applied successfully to a range of deactivated mono-substituted benzenes to give para-isomers in significantly higher proportions than in the corresponding traditional nitration reactions.
| Item Type: | Article |
|---|---|
| Status: | Published |
| Schools: | Schools > Chemistry |
| Subjects: | Q Science > QD Chemistry |
| Uncontrolled Keywords: | Nitration; Deactivated mono-substituted benzenes; Acyl nitrate; Acidic zeolite catalysis; Hβ; Regioselectivity |
| Publisher: | Springer Verlag |
| ISSN: | 1011-372X |
| Date of First Compliant Deposit: | 30 March 2016 |
| Last Modified: | 05 Aug 2026 04:40 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/12722 |
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