The Solvation and Dissociation of 4-Benzylaniline Hydrochloride in Chlorobenzene

Abstract

A reaction scheme is proposed to account for the liberation of 4-benzylaniline from 4-benzylaniline hydrochloride, using chlorobenzene as a solvent at a temperature of 373 K. Two operational regimes are explored: "closed" reaction conditions correspond to the retention of evolved hydrogen chloride gas within the reaction medium, whereas an "open" system permits gaseous hydrogen chloride to be released from the reaction medium. The solution phase chemistry is analyzed by 1 H NMR spectroscopy. Complete liberation of solvated 4-benzylaniline from solid 4-benzylaniline hydrochloride is possible under "open" conditions, with the entropically favored conversion of solvated hydrogen chloride to the gaseous phase thought to be the thermodynamic driver that effectively controls a series of interconnecting equilibria. A kinetic model is proposed to account for the observations of the open system.

Spectroscopic Characterization of Model Compounds, Reactants, and Byproducts Connected with an Isocyanate Production Chain

“…Polyurethanes are typically prepared by the reaction between an isocyanate and a diol . Methylene diphenyl diisocyanate (MDI, OCNC 6 H 4 CH 2 C 6 H 4 NCO) dominates the global isocyanate market; in 2011 the MDI total production capacity was estimated to be ∼5 Mt …”

Insight into thermal dissociation of tri‐n‐octylamine hydrochloride: The key to realizing CO2 mineralization with waste calcium/magnesium chloride liquids

“…Inspired by the work of Gibson et al, a possible reaction scheme for the thermal dissociation of TOAHCl in decalin was proposed below as Equation . …”

“…Studies have been done for the closed and open system, showing that the release of HCl is crucial to break the reaction equilibrium of dissociation of amine hydrochloride to realize the thermal dissociation process of amine hydrochlorides. With different flow rates of N 2 , Figure was drawn as follows, which shows the substantial influence.…”

“…According to the work of Gibson et al., the dissociation of amine hydrochloride in dilute chlorobenzene follows the first‐order reaction principle in open system. Besides, under certain high N 2 flow rate, the external diffusion could be ignored as far as possible.…”

“…Inspired by the work of Gibson et al, 44,45 a possible reaction scheme for the thermal dissociation of TOAHCl in decalin was proposed below as Equation (13).…”