Measurement and correlation of solubility of abietic acid in ethanol + water mixtures

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Highlights

  • We measured the solubility of abietic acid in (ethanol + water) mixtures.

  • We correlated the SLE data using the Wilson, NRTL and λh equations.

  • We discussed the solution characteristics via the molar mixing enthalpy (HE).

Abstract

Using a laser monitoring observation technique, the solubility of abietic acid in (ethanol + water) mixtures was measured by a dynamic method at atmospheric pressure. The solubility of abietic acid increased with an increase of temperature and the concentration of ethanol. Experimental solubility data were correlated by means of the Wilson, NRTL and λh equations utilizing parameters derived from the (solid + liquid) equilibrium (SLE) data. The results showed that the three equations are suitable for description of the solubility data of abietic acid in the (ethanol + water) mixtures investigated.

Introduction

Abietic acid is a substance with biological activity, and can be widely used in many industries such as medicine [1], [2], [3], pesticide [4], [5], and fine chemicals [6], [7], [8]. Abietic acid is the major component of rosin, the chemical structure of which is shown in figure 1. All the components in rosin, including pimaric acid, isopimaric acid, palustric acid, levopimaric acid, dehydroabietic acid, neoabietic acid, are mono-carboxylic acids with three-ring phenanthrene skeleton [9], [10]. Most of which are isomers. This makes the isolation of abietic acid from rosin a difficult problem. In order to broaden the application of renewable rosin resource, it is vital to isolate and purify every component for the raw material of chemical synthesis and biotransformation. The separation of abietic acid from rosin involves preparation of derivatives of abietic acid in the crude mixtures, purification of these derivatives by crystallization procedures and regeneration of the acid [11], [12]. Pure abietic acid can be obtained after further purification by means of crystallization using ethanol as solvent. Unfortunately, the solubility of abietic acid in ethanol is scarce, except for abietic acid in methanol, absolute alcohol, propanol and n-butanol [13]. To the best of our knowledge, the solubility of abietic acid in (ethanol + water) mixtures has not been reported in the literature. Solubility data of abietic acid could be valuable in pharmaceutical applications as many abietic acid derivatives are of the main and important pharmaceutical compounds. Therefore, in this paper, we carried out the systematic studies on solubility of abietic acid in (ethanol + water) mixtures. The solubility was measured at atmospheric pressure by a laser monitoring observation technique, and the Wilson, NRTL and λh equations were used for the correlation of the experimental data.

Section snippets

Materials

Abietic acid was prepared in our laboratory by the method suggested in literature [14]. The mass fraction of abietic acid was 99.11% by gas chromatography (Aglient GC 6890, USA). Ethanol (99.8 mass%) was purchased from Guangdong Guanghua Chemical Co., Ltd. and used without further purification. Distilled deionised water was obtained from a RO-EDI Barnstead Easy pure RF compact ultrapure water system (Guangzhou JingYuan Seawater Desalination and Water Treatment Company). The provenance and

Results and discussion

Solubility of abietic acid in (ethanol + water) mixtures belongs to (solid + liquid) equilibrium of single solute in mixed solvent. However, because of abietic acid is not dissolved in water, the energy parameters of binary activity coefficient models which used to describe (solid + liquid) equilibrium of abietic acid in water cannot be obtained, and cannot correlate solubility data by ternary activity coefficient models directly. In this study, mixed solvent of ethanol and water was considered as a

Conclusions

Using a laser monitoring observation technique, the solubility of abietic acid in (ethanol + water) mixtures has been determined in this work. The solubility of abietic acid in the (ethanol + water) mixtures investigated increase with the increasing of temperature, and the concentration of ethanol. The lowest and highest solubility were found in w2 = 0.7209 and w2 = 1.0000, respectively. Three equations were used for the correlation of the SLE experimental data (Wilson, NRTL, λh). The results of the

Acknowledgements

The authors gratefully acknowledge financial support for this research from the National Natural Science Foundation of China (Grant Nos. 20976031 and 31060102), the Natural Science Foundation of Guangxi Autonomous Region (Grant Nos. 2011GXNSFD018011, 2010GXNSFA013042 and 0991030), Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (Grant No. Z001), Scientific and Technological Project of Guangxi (Grant No. 1099060-2), the Science and Technology Program

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