Paracyclophane (PCP) and byproducts were obtained from (p-methylbenzyl)trimethylammonium hydroxide (QOH) by reaction with NaOH in concentrated water solutions. The system presents a miscibility gap: selectivities and kinetics were separately studied in a NaOH-rich ("Na") region, a QOH-rich ("Q") region, and a "dilute" region, at temperatures in the range 70-110 °C. The reaction rate is much higher in the Na region, particularly at high levels of NaOH concentration, but selectivity to PCP is better in the other regions. The dependence of the reaction rate on the alkali concentration is discussed, relating it to the poor solvation of OH- ions.
SYNTHESIS OF [2.2]PARACYCLOPHANE VIA HOFMANN ELIMINATION - A KINETIC-STUDY OF THE HOMOGENEOUS REACTION / P. BELTRAME, P. BELTRAME, P. CARNITI, P. DELOGU, C. PINA, G. ZURETTI. - In: INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH. - ISSN 0888-5885. - 28:8(1989), pp. 1125-1130.
SYNTHESIS OF [2.2]PARACYCLOPHANE VIA HOFMANN ELIMINATION - A KINETIC-STUDY OF THE HOMOGENEOUS REACTION
P. BELTRAMEPrimo
;P. CARNITI;G. ZURETTIUltimo
1989
Abstract
Paracyclophane (PCP) and byproducts were obtained from (p-methylbenzyl)trimethylammonium hydroxide (QOH) by reaction with NaOH in concentrated water solutions. The system presents a miscibility gap: selectivities and kinetics were separately studied in a NaOH-rich ("Na") region, a QOH-rich ("Q") region, and a "dilute" region, at temperatures in the range 70-110 °C. The reaction rate is much higher in the Na region, particularly at high levels of NaOH concentration, but selectivity to PCP is better in the other regions. The dependence of the reaction rate on the alkali concentration is discussed, relating it to the poor solvation of OH- ions.
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