From glycerol to chlorohydrin esters using a solvent-free system. Microwave irradiation versus conventional heating

Marc Escribà, Jordi Eras, Miquel Duran, Sílvia Simon, Cristina Butchosa, Gemma Villorbina, Mercè Balcells, Ramon Canela

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17 Cites (Scopus)

Resum

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.

Idioma originalAnglès
Pàgines (de-a)10370-10376
Nombre de pàgines7
RevistaTetrahedron
Volum65
Número50
DOIs
Estat de la publicacióPublicada - 12 de des. 2009
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