NDLI: Thermo-analytical determination of intermediates in the copper catalysed rearrangement of <i>o</i>-toluic acid to <i>meta</i>-cresol

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Comment on “Nickel nanoparticles catalyse reversible hydration of carbon dioxide for mineralization carbon capture and storage” by G. Bhaduri and L. Šiller, Catal. Sci. Technol., 2013, 3, 1234

Reply to the ‘Comment on “Nickel nanoparticles catalyse reversible hydration of carbon dioxide for mineralization carbon capture and storage”’ by D. Britt, Catal. Sci. Technol., 2013, 3, DOI: 10.1039/C3CY00142C

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Thermo-analytical determination of intermediates in the copper catalysed rearrangement of o-toluic acid to meta-cresol

Content Provider	Royal Society of Chemistry (RSC)
Author	Sunil, Abraham C. Bezuidenhoudt, Barend C. B. Langner, Ernst H. G. Marais, Charlene
Copyright Year	2013
Abstract	The intermediates formed during the conversion of o-toluic acid 2 to m-cresol 1 in the presence of Cu(II) according to the Keading process, together with the temperatures at which crucial changes occur, have been investigated by means of X-ray diffractometry [which confirmed the formation of the paddlewheel copper complex tetrakis(μ2-2-methylbenzoato)bis(2-methylbenzoic acid)copper(II) 5 with two apical o-toluic acid ligands], differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), NMR spectroscopy, infrared spectrometry (IR) and Maldi-Tof mass spectrometry. The major chemical change observed at 164 °C might be ascribed to the dissociation of the apical o-toluic acid ligands from 5 to give tetrakis(μ2-2-methylbenzoato)copper(II) 6 accompanied by water loss. O–C bond formation between the carboxylate oxygens and ortho-carbons of the toluic acid moieties in adjacent paddlewheels of the stepped polymeric 6 is proposed to explain the formation of copper(I) 2-methyl-6-{[(2-methylphenyl)carbonyl]oxy}benzoate 8via intermediate 7 and initiates the decomposition observed by DSC at 236 °C. Decarboxylation of 8 at 249.5 °C gives 3-methylphenyl 2-methylbenzoate 4, which can be hydrolysed to o-toluic acid 2 and the target compound, m-cresol 1.
Starting Page	2227
Ending Page	2233
Page Count	7
File Format	HTM / HTML PDF
ISSN	20444753
Volume Number	3
Issue Number	9
Journal	Catalysis Science & Technology
DOI	10.1039/c3cy00119a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Benzoic acid Paddle wheel Differential scanning calorimetry Infrared spectroscopy Thermogravimetric analysis Chemical bond M-Cresol Nuclear magnetic resonance spectroscopy Tof Dissociative X-ray crystallography DSC Carboxylic acid Decarboxylation Carbonyl group Copper Mass spectrometry
Content Type	Text
Resource Type	Article
Subject	Catalysis

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