Epoxidation of DL-limonene using an indenyl molybdenum(II) tricarbonyl complex as catalyst precursor
authors Abrantes, M; Bruno, SM; Tome, C; Pillinger, M; Goncalves, IS; Valente, AA
nationality International
journal CATALYSIS COMMUNICATIONS
author keywords Molybdenum; Indenyl complexes; Oxidative decarbonylation; Limonene; Epoxidation; Tert-butylhydroperoxide
keywords OLEFIN EPOXIDATION; TUNGSTEN COMPLEXES; ETA(5)-CYCLOPENTADIENYL MOLYBDENUM; CYCLOALKYL MOIETIES; CRYSTAL-STRUCTURES; BRIDGING UNITS; ANSA COMPOUNDS; OXIDATION; DERIVATIVES; REACTIVITY
abstract The complex IndMo(CO)(3)Me (Ind = eta(5)-C9H7) is an effective catalyst precursor for the epoxidation of DL-limonene using the following oxidant solutions: (i) commercial tert-butylhydroperoxide in decane (TBHPdec), (ii) commercial aqueous TBHP (TBHPaq) pre-mixed with limonene (TBHP_lim), or (iii) TBHPaq pre-mixed with 1,2-dichloroethane (TBHPdce); simple pre-drying treatments of the reaction solutions were applied prior to feeding the catalyst precursor to the batch reactor. The best results were found for the efficiently pre-dried reaction system (iii), which gave higher 1,2-epoxy-p-meth-8-ene yield at 35 min/55 degrees C than (i) (82% and 73% yield, respectively). This approach avoids the undesirable partial oxidation of decane, which would imply costly work-up procedures to remove high boiling point impurities from the epoxides. These results together with studies on the reactivity of different olefins indicate fairly high regioselectivity toward the epoxidation of the internal double bonds. (C) 2011 Elsevier B.V. All rights reserved.
publisher ELSEVIER SCIENCE BV
issn 1566-7367
year published 2011
volume 15
issue 1
beginning page 64
ending page 67
digital object identifier (doi) 10.1016/j.catcom.2011.08.015
web of science category Chemistry, Physical
subject category Chemistry
unique article identifier WOS:000297570500015
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journal impact factor 3.463
5 year journal impact factor 3.468
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