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Molecular CatalysisVolume 434, 2017, Pages 175-183

Kinetic study of Friedel-Crafts acylation reactions over hierarchical MCM-22 zeolites(Article)

  • aÁrea Departamental de Engenharia Química, Instituto Superior de Engenharia de Lisboa, IPL R. Conselheiro Emídio Navarro, Lisboa, 1959-007, Portugal
  • bCentro de Química e Bioquímica, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa Ed. C8, Campo Grande, Lisboa, 1749-016, Portugal
  • cDepartamento de Química e Farmácia, Universidade do Algarve, Campus de Gambelas, Faro, 8005-139, Portugal

Abstract

Friedel-Crafts acylation was studied under mild conditions using hierarchical MCM-22 zeolites prepared by desilication and by desilication + acid treatment, using furan, pyrrole and anisole as substrates, and acetic anhydride as acylating agent. Enhanced catalysis was observed for furan and anisole, especially at short reaction times. Kinetic results modelling using non-linear regressions applied to a simplified Langmuir–Hinshelwood equation showed that desilication treatment followed by acid treatment improved kinetics (higher k and TOF). A QSPR methodology using nine substrate and zeolite descriptors was applied to model kinetics and adsorption. For both processes, the best QSPR model equations lead to the same descriptors, namely, Brønsted acidity, as zeolite's feature, and both van der Waals volume and Dimroth–Reichardt ETN parameter (related to dipolarity and Lewis acidity) as substrates’ characteristics. Normalization of descriptors allowed quantification of each descriptor's relative importance leading to a better understanding of the catalytic and adsorption processes. © 2017 Elsevier B.V.

Author keywords

Friedel-Crafts acylation reactionsHierarchical MCM-22Kinetic modellingNon-linear regressionsQSPR methodology

Indexed keywords

Engineering controlled terms:Aromatic compoundsKinetic theoryKineticsOrganic pollutantsSubstratesVan der Waals forcesZeolites
Engineering uncontrolled termsFriedel-crafts acylationHierarchical MCM-22Kinetic modellingNon-linear regressionQSPR methodology
Engineering main heading:Acylation

Funding details

Funding sponsor Funding number Acronym
Fundação para a Ciência e a Tecnologia
See opportunities
PEST UID/MULTI/00612/2013
  • 1

    The authors acknowledge the financial support of FCT through PEST UID/MULTI/00612/2013. Appendix A

  • ISSN: 24688231
  • CODEN: MCOAD
  • Source Type: Journal
  • Original language: English
  • DOI: 10.1016/j.mcat.2017.03.007
  • Document Type: Article
  • Publisher: Elsevier B.V.

  Nunes, N.; Área Departamental de Engenharia Química, Instituto Superior de Engenharia de Lisboa, IPL R. Conselheiro Emídio Navarro, Lisboa, Portugal;
© Copyright 2017 Elsevier B.V., All rights reserved.

Cited by 2 documents

Shkuropatov, A.V. , Knyazeva, E.E. , Ponomareva, O.A.
Synthesis of Hierarchical MWW Zeolites and Their Catalytic Properties in Petrochemical Processes (Review)
(2018) Petroleum Chemistry
Makihara, M. , Aoki, H. , Komura, K.
Reaction Profiles of High Silica MOR Zeolite Catalyzed Friedel–Crafts Acylation of Anisole Using Acetic Anhydride in Acetic Acid
(2018) Catalysis Letters
View details of all 2 citations
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