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

Heterogeneous catalytic solvent-free synthesis of 3,3,5-trimethyl cyclohexyl anthranilic acid esters via transesterification

Chittaranjan S. Thatte, Manapragada V. Rathnam, Ashutosh Namdeo, and Kiran Rane

Chemistry Research Laboratory, B. N. Bandodkar College of Science, Thane, India

E-mail: mvrathnam58@rediffmail.com

Abstract: The transesterification of anthranilates with both mixtures of cis and trans and pure trans 3,3,5-trimethyl cyclohexanol was studied using ‘calcium-oxide- and magnesium-oxide’-based catalysts under ‘solvent-free’ conditions. The catalysts were characterized by XRD, CO₂-TPD, BET-surface area, and FEG–SEM analysis. Pure calcium oxide was found to be the most effective heterogeneous catalyst. Pure ‘calcium-oxide’-based catalyst was recycled five times without appreciable loss in the catalytic activity. The TOF after five recycles was 10.7 mol/mol of catalyst/h. The study was further extended for the synthesis of new anthranilates. The synthesized pure esters have been characterized by UV–Vis, IR-, ¹H NMR-, and ¹³C NMR spectroscopies and mass spectrometry.

Keywords: Transesterification; Methyl anthranilate; Trimethyl cyclohexanol; Calcium oxide; Mixed magnesium–calcium oxide

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-016-0061-z

Chemical Papers 71 (5) 981–990 (2017)