ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Regioselective synthesis of 5-aryl azo salicylaldehydes catalyzed by Zn/SBA-15

Forouzan Zonouzi, Alireza Rahmani, Hamid Dezhampanah, Bahram Ghalami-Choobar, and Afsaneh Zonouzi

University Campus 2, University of Guilan, Rasht, Iran

E-mail: B-ghalami@guilan.ac.ir

Abstract: Synthesis of (E)-2-hydroxy-5-(aryldiazenyl)benzaldehydes was investigated. Various Lewis acids were tested as catalyst to achieve regioselectivity. In addition to various commercial catalysts, mesoporous Zn/SBA-15 was synthesized through a modified direct method with chloride salt as zinc precursor and characterized using N₂-physisorption, low-angle XRD, FESEM and EDX methods; specific surface area of 832 m² g⁻¹ is a noteworthy result compared to the literature. The synthesized catalyst showed the best results in terms of both total yield and regioselectivity. A scalable two-phase reaction media was used to facilitate both reaction progress monitoring and final product separation. Minimizing solvent consumption, this method can be considered for larger scale production of aryl azo dyes and related compounds.

Keywords: Catalyst ; Azo dyes ; Regioselective ; Synthesis ; Lewis acids 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-019-00790-1

Chemical Papers 73 (10) 2409–2415 (2019)