Solubility of N-Ethylcarbazole in different organic solvent at 279.15–319.15 K

doi:10.1016/j.fluid.2014.06.030

Fluid Phase Equilibria

Volume 378, 25 September 2014, Pages 78-82

https://doi.org/10.1016/j.fluid.2014.06.030 Get rights and content

Highlights

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The solubility of N-Ethylcarbazole in seven solvents was investigated.
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The modified Apelblat equation and the λh equation correlate in good way the solubility values.
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The solution process of N-Ethylcarbazole was endothermic.

Abstract

The solubility of N-Ethylcarbazole in methanol, ethanol, n-propanol, isopropanol, 1-butanol, 1-pentanol and petroleum ether was measured over the temperature range of 279.15–319.15 K at around 4 K intervals under atmospheric pressure. Experimental result showed that the solubility of N-Ethylcarbazole in seven solvents increased with the increasing temperature and they were in good agreement with the calculated solubility of the modified Apelblat equation and the λh equation. The thermodynamic properties of the solution process, including the Gibbs energy, enthalpy, and entropy were calculated by the van’t Hoff analysis. The values of both the standard molar enthalpy change and standard molar Gibbs energy change of solution were positive, which indicated that the process was endothermic.

Introduction

N-Ethylcarbazole (C₁₄H₁₃N, FW195.2597, CASRN:86-28-2, Fig. 1) is a kind of important organic synthetic intermediate which is used for synthesizing dyes such as Sulphur vat blue GNX and Permanent violet RL [1], [2]. Permanent violet RL is now recognized as the best purple pigment. It is widely used in plastics, coatings, printing, printing ink and leather coloring agent [3]. In addition, as one of the coal tar extractive, the price of N-Ethylcarbazole is keep rising with the rising price of coal tar. The physical and chemical properties of N-Ethylcarbazole increasingly attract so much attention and concern. The solubility of N-Ethylcarbazole in different solvents is important because they are guidelines for choosing the suitable solvent and are beneficial to the optimization of the crystallization process [4].

In this study, the solubility of N-Ethylcarbazole in methanol, ethanol, n-propanol, isopropanol, 1-butanol, 1-pentanol and petroleum ether was measured at the temperature range between 279.15 K and 319.15 K under atmospheric pressure by gravimetric method, the solubility data was fitted to the modified Apelblat equation and λh equation to obtain the empirical parameters [5].

Section snippets

Materials and apparatus

N-Ethylcarbazole (C₁₄H₁₃N, FW195.2597, CASRN:86-28-2, Fig. 1) with a mass fraction purity >97 was purchased from Aladdin Industrial Corporation. Its purity was measured by high performance liquid chromatography (HPLC type Agilent 1260 Infinity LC, Agilent Technologies) [6]. All solvents (Shanghai Shenbo Chemical Co., Ltd.) used for experiments were analytical reagent grade and their mass fraction purities were higher than 99. More details about the purity of solvents were listed in Table 1. All

Solubility data and correlation models

The saturated mole fraction solubility (x) and the calculated solubility values (x^c) of N-Ethylcarbazole in methanol, ethanol, n-propanol, isopropanol, 1-butanol, 1-pentanol and petroleum ether over the temperature range of 279.15–319.15 K was presented in Table 2.

The influence of temperatures on the solubility of N-Ethylcarbazole has been represented by the following modified Apelblat model [10], [11]: $\ln x = A + \frac{B}{(T / K)} + C \ln (T / K)$ where T represents the absolute temperature, A, B and C represent the

Conclusions

The solubility of N-Ethylcarbazole in methanol, ethanol, n-propanol, isopropanol, 1-butanol, 1-pentanol and petroleum ether was measured over the temperature range of 279.15–319.15 K. It could be seen from Table 2, Table 3, Table 4 and Fig. 2, the solubility in all the selected solvents increased with the increasing temperature.

According to the solubility of N-Ethylcarbazole in the studied solvents, the solubility in petroleum ether was the highest, whereas the lowest in methanol. The

Acknowledgements

This research work was financially supported by Key topics for State Key Laboratory of Materials-Oriented Chemical Engineering (Grant No. ZK201304), the Doctoral fund project (Grant No. 20133221110010), the science and technology support program-part of agriculture (Grant No. BE2013442) and the Joint innovation and research funding-prospective joint research projects (Grant No. BY2013005-02).

References (20)

C. Wu et al.
Thermochim. Acta
(2012)
K. Wang et al.
Thermochim. Acta
(2012)
Y.H. Hu et al.
J. Mol. Liq.
(2012)
D. Grant et al.
Int. J. Pharm.
(1984)
A. Apelblat et al.
J. Chem. Thermodyn.
(1999)
J.P. Fan et al.
J. Chem. Thermodyn.
(2013)
B.W. Long et al.
Fluid Phase Equilib.
(2008)
M.A. Ruidiaz et al.
Fluid Phase Equilib.
(2010)
W.E. Acree et al.
Thermochim. Acta
(1991)
X.Q. Zhou et al.
Fluid Phase Equilib.
(2012)

There are more references available in the full text version of this article.

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Solubility of N-Ethylcarbazole in different organic solvent at 279.15–319.15 K

Highlights

Abstract

Introduction

Section snippets

Materials and apparatus

Solubility data and correlation models

Conclusions

Acknowledgements

Thermochim. Acta

Thermochim. Acta

J. Mol. Liq.

Int. J. Pharm.

J. Chem. Thermodyn.

J. Chem. Thermodyn.

Fluid Phase Equilib.

Fluid Phase Equilib.

Thermochim. Acta

Fluid Phase Equilib.