@article{ca899b5f61c4455283d8a03a2514e913,
title = "From glycerol to chlorohydrin esters using a solvent-free system. Microwave irradiation versus conventional heating",
abstract = "Esterification-chlorination of glycerol provides chlorohydrin esters in high yields. A ratio of reagents close to equivalence can be used, so that atom economy of the reaction is optimized. The reaction can be carried out using either classical or microwave heating, and no solvent is required. 2-Chloro-1-(chloromethyl)ethyl esters can be obtained in high regioisomeric relationship when either low or moderate temperature is used. In contrast, microwave irradiation allows the use of higher reaction temperatures that render mixtures of both regioisomers in variable relationships. Kinetic control of the process is proposed for classical heating, and experimental results are analyzed with the aid of ab initio calculated values. Non-thermal phenomena can be used to explain the high efficiency of microwave irradiation at low temperature.",
keywords = "Chlorohydrin esters, CTMS, Glycerol, MW, Nucleophilic substitution, Rearrangement",
author = "Marc Escrib{\`a} and Jordi Eras and Miquel Duran and S{\'i}lvia Simon and Cristina Butchosa and Gemma Villorbina and Merc{\`e} Balcells and Ramon Canela",
note = "Funding Information: This work was supported in part by a Grant-in-Aid for the Secretar{\'i}a de Estado de Pol{\'i}tica Cient{\'i}fica y Tecnol{\'o}gica of the Spanish Ministry of Education and Culture (Contract grant number: CTQ2006-07451/PPQ). The authors are grateful to the Comissionat per a Universitats i Recerca del Departament d'Innovaci{\'o}, Universitats i Empresa de la Generalitat de Catalunya and to the the European Social Fund (ESF) for the FI grant of Marc Escrib{\`a} Gelonch. The assistance of Joan Sall{\'e}s. Dpt. of Mass Spectrometry, and Miquel Peric{\`a}s. Director of the Institut Catal{\`a} d'Investigaci{\'o} Qu{\'i}mica (Tarragona, Spain), for obtaining HRMS spectra is gratefully acknowledged. The contribution of Albert Tom{\`a}s for his technical assistance is greatly appreciated.",
year = "2009",
month = dec,
day = "12",
doi = "10.1016/j.tet.2009.10.048",
language = "English",
volume = "65",
pages = "10370--10376",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Ltd.",
number = "50",
}