Solubility and mixing thermodynamic properties of levamisole hydrochloride in twelve pure solvents at various temperatures

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Abstract

The solubility of solid compounds and active pharmaceutical ingredient in different solvents is important for its crystallization and purification industry. In this work, by using a laser dynamic method, the solubility of levamisole hydrochloride in methanol (MT), ethanol (ET), isopropanol (IPA), n-propanol (NPA), n-butanol (NBA), 2-butanol (SBA), isobutanol (IBA), n-pentanol (NPT), 3-methyl-1-butanol (IAA) and n-hexanol (NHA) from (283.15 to 323.15) K, dimethyl sulfoxide (DMSO) from (293.15 to 333.15) K and water from (283.15 to 308.15) K were measured under atmospheric pressure. The measured results showed that the experimental solubility of levamisole hydrochloride increased non-linearly with the temperature in the studied pure solvents. The measured solubility data were all correlated by the Yaws model equation, non-random two liquid (NRTL) model equation, universal quasi chemical (UNIQUAC) model equation, Wilson model equation and λh equation. Besides, the logarithm of activity coefficient of levamisole hydrochloride (lnγ1) were calculated with the NRTL model, Wilson model and UNIQUAC model. The maximum relative average deviation (ARD) was 0.2008, the maximum root-mean-square deviation (RMSD) was 0.0089. Basically speaking, the measured solubility data in this study can be well correlated with the five thermodynamic models. Based on the solubility data and Wilson model, the mixing entropy, mixing enthalpy and mixing Gibbs energy were evaluated. The logarithm of the solute activity coefficients lnγ1in the studied saturated solutions were calculated, The positive values of lnγ1 means that the repulsive interactions exist between levamisole hydrochloride and the corresponding solvents (NBA, NPA, NHA, IPA, IBA, SBA and IAA), and the solutions system positively deviate from Raoult’s law; The negative values of lnγ1 means that the attractive interactions exist between levamisole hydrochloride and the corresponding solvents (MT, ET, NPT, DMSO and water), and the solutions system minus deviate from Raoult’s law. This work can give fundamental data for the crystallization and purification of levamisole hydrochloride.

Introduction

Levamisole hydrochloride (CAS Registry No. 16595-80-5) is a white crystalline powder, which chemical structure is presented in Fig. 1. Its molecular formula and molar mass are C11H12N2S.ClH and 240.75 g·mol−1, respectively. Levamisole hydrochloride is a broad-spectrum, highly effective, low toxic nematode repellent and it is effective against gastrointestinal nematodes in many animals. The industrial products of levamisole hydrochloride always have some problems, such as low purity, poor crystallization habits and low yield, these problems directly affect the efficacy of levamisole hydrochloride. In order to solve the problems mentioned above, solution crystallization process is the preferred option. Therefore, the experimental solubility data of levamisole hydrochloride is significant for its purification process.

As mentioned above, the main aim of this study is to extend the experimental solubility database of levamisole hydrochloride, and to evaluate the solution thermodynamic behavior of levamisole hydrochloride in the studied solvents. Specifically speaking, the contents of our present study are to (1) measure the experimental solubility data of levamisole hydrochloride in (MT, ET, NPA, IPA, NBA, IBA, SBA, NPT, IAA and NHA) from (283.15 to 323.15) K, DMSO from (293.15 to 333.15) K and water from (283.15 to 308.15) K; (2) use the Yaws model equation, NRTL model equation, UNIQUAC model equation, Wilson model equation and λh equation to correlate the solubility data of levamisole hydrochloride; (3) evaluate the thermodynamic properties for the mixing process of levamisole hydrochloride in the studied solvents. Meanwhile, the melting properties of levamisole hydrochloride was obtained by the technology of thermogravimetry and differential scanning calorimetry (TG-DSC) analysis. Furthermore, the power X-ray diffraction (PXRD) data of levamisole hydrochloride used in this work was collected to evaluate the possible polymorphic transition. This work can give fundamental data for the crystallization and purification of levamisole hydrochloride.

Section snippets

Materials

The experimental raw levamisole hydrochloride (0.99 mass fraction purity, lot number: K1214026) used in this work was supplied by Shanghai Aladdin Biochemical Technology Co., Ltd. of china, the mass fraction purity of levamisole hydrochloride was analyzed by high performance liquid chromatography (HPLC, Agilent-1100, USA). In the present study, all the organic solvents, including MT, ET, NPA, IPA, NBA, IBA, SBA, NPT, IAA, NHA and DMSO, were used as received without further purification and the

TG-DSC analysis

From the DSC scan result of levamisole hydrochloride presented in Fig. 2, the TG and DSC curves were obtained between 350 and 600 K. Levamisole hydrochloride was stable without obvious mass loss when the temperature below 503 K, and the onset melt temperature (Tonset) of the raw sample was 499.15 K and then there was about 0.48% loss of mass in the TG curve. When the temperature reached at 503 K and then the loss of mass was about 0.82%, which indicated that the melting process was accompanied

Conclusion

The solubility of levamisole hydrochloride in methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, 2-butanol, n-pentanol, 3-methyl-1-butanol and n-hexanol from (283.15 to 323.15) K, dimethyl sulfoxide from (293.15 to 333.15) K and water from (283.15 to 308.15) K was measured by a laser dynamic method at atmospheric pressure. Results shows that the solubility of levamisole hydrochloride increases with the increase of temperature. The order of the experimental mole fraction

Acknowledgment

This research work was financially supported by the National Science Foundation of China (Grant No. 21506197, Grant No. 21646011).

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