Determination and correlation of solubility of tylosin tartrate in alcohol mixtures

doi:10.1016/j.jct.2014.08.026

The Journal of Chemical Thermodynamics

Volume 80, January 2015, Pages 128-134

https://doi.org/10.1016/j.jct.2014.08.026 Get rights and content

Highlights

•
The solubility of tylosin tartrate in selected solvents has been obtained in this work.
•
The results show that the three models agree well with the experimental data.
•
The modified Apelblat model were more accurate than λh model and van’t Hoff model.
•
The dissolution enthalpy and entropy of tylosin tartrate were calculated from the solubility data.

Abstract

Data on (solid + liquid) equilibrium of tylosin tartrate in {methanol + (ethanol, 1-propanol or 2-propanol)} solvents will provide essential support for industrial design and further theoretical studies. In this study, the solubility of tylosin tartrate in alcohol mixtures was measured over temperature range from (278.15 to 323.15) K under atmospheric pressure by a gravimetric method. From the experimental results, the solubility of tylosin tartrate in selected solvents noted above was found to increase with increasing temperature and mass fraction of methanol. The solubility data were correlated with the modified Apelblat equation, the λh equation and van’t Hoff equation. The results showed that the three equations agreed well with the experimental values, and that the modified Apelblat equation was more accurate than the λh equation and van’t Hoff equation. Further, the standard enthalpy, standard entropy and standard Gibbs free energy of solution of tylosin tartrate in mixed solvents were calculated according to solubility results, model parameters with modified Apelblat equation and van’t Hoff equation.

Graphical abstract

Data on (solid + liquid) equilibrium of tylosin tartrate in {methanol + (ethanol, 1-propanol or 2-propanol)} solvents was measured over temperature range from (278.15 to 323.15) K under atmospheric pressure by a gravimetric method. From the experimental results, it can be seen that solubility of tylosin tartrate increases with increasing mass fraction of methanol in mixed solvents at a constant temperature, and increases with increasing temperature at the same mass fraction. The solubility of tylosin tartrate in methanol is higher than in methanol mixture solvents, and in 2-propanol is the lowest. The solubility data were correlated well with modified Apelblat equation, λh equation and van’t Hoff equation, and that modified Apelblat equation was more accurate than λh equation and van’t Hoff equation. Further, the standard enthalpy, standard entropy and standard Gibbs free energy of solution of tylosin tartrate in mixed solvents were calculated according to solubility data and model parameters with modified Apelblat equation and van’t Hoff equation.

Introduction

Tylosin tartrate (CAS Registry No: 74610-55-2) is a kind of the tylosin derivative and has the same antibiosis properties as tylosin. The chemical structure is shown in figure 1. Tylosin tartrate is a medium spectrum antibiotic not only used in veterinary medicine for the treatment of infections caused by most Gram-positive bacteria, mycoplasmas, some Gram-negative bacteria and Chlamydia [1], [2], [3], but also used as a feed additive to increase the rates of weight gain and improve the feed efficiency of companion animals, such as cattle, chicken, turkey, and swine [4], [5], [6]. But the residues of these antibiotics may stay in the edible tissue of animals and pose a threat to the health of humans when misused. Therefore, tylosin was banned as a growth promoter by the EU Commission in 1999 [7], disabled as drugs in fishery breeding by China’s agricultural industry standards NY 5071-2002, and canceled from edible animal breeding by FDA in U.S in 2014 [8]. Maximum residue levels (MRLs) of these drugs in livestock products have been established in many countries [9], [10], [11].

For expanding the fields of usage and purification of tylosin tartrate, the data of (solid + liquid) equilibrium are required. Liquid alcohols play an important role and are widely used in industry and science research as reagents, solvents and fuels. The solubility of tylosin tartrate in alcohol solvents has not been published at present. Hence we measured solubility of tylosin tartrate in {methanol + (ethanol, 1-propanol or 2-propanol)} over the temperature range from (278.15 to 323.15) K under atmospheric pressure by a gravimetric method. The experimental values were correlated with the modified Apelblat equation, the λh equation and van’t Hoff equation. The standard enthalpy, entropy and Gibbs free energy of solution of tylosin tartrate were calculated according to the modified Apelblat equation and van’t Hoff equation.

Section snippets

Materials

Tylosin tartrate (C₄₆H₇₇NO₁₇·C₄H₆O₆, molar mass 1066.19) was obtained from Ningxia Tairui Pharmaceutical Co. Ltd., China and re-crystallized. Its mass faction purity was 0.99, which was determined by HPLC (type Agilent 1200, Agilent Technologies). It was dried in vacuum at T = 23.15 K for 24 h and stored in a desiccator. All the solvents (purchased from Tianjin Wind Ship Chemical Co. Ltd., China) were analytical reagent grade. Their mass fraction purities were better than 99.5% and were used

Solubility data

Tylosin tartrate is a biological product and shows excellent stability at temperatures below 333.15 K [16], [17], and that the boiling points of selected solvents are lower. Therefore the solubility values of tylosin tartrate in alcohol mixtures within the temperature range from (278.15 to 323.15) K were determined by experiment. The results show in TABLE 2, TABLE 3 and graphically in FIGURE 3, FIGURE 4, FIGURE 5, respectively. The relative error (RD), the average absolute deviation (RAD) and the

Conclusions

New experimental results for solubility of tylosin tartrate in {methanol + (ethanol, 1-propanol or 2-propanol)} mixtures are presented in this work. The solubility of tylosin tartrate in selected solvents was studied over the temperature range from (278.15 to 323.15) K by a gravimetric method. The solubility of tylosin tartrate increases with increasing mass fraction of methanol in mixtures and with increasing temperature. The experiment results were well correlated with the modified Apelblat

References (27)

X.M. Jiang et al.
Fluid Phase Equilib.
(2013)
Q.S. Yu et al.
Thermochim. Acta
(2013)
X.Y. Zhang et al.
Fluid Phase Equilib.
(2013)
Y. Li et al.
Fluid Phase Equilib.
(2010)
A. Apelblat et al.
J. Chem. Thermodyn.
(1997)
A. Apelblat et al.
J. Chem. Thermodyn.
(1999)
H. Buchowski et al.
Fluid Phase Equilib.
(1986)
T. Li et al.
Fluid Phase Equilib.
(2012)
J.M. McGuire et al.
Antibiot. Chemother.
(1961)
H.A. Kirst. 5 Semi-synthetic derivatives of 16-membered macrolide antibiotics, in: G.P. Ellis, D. K. Luscombe (Eds.),...

D.P. Peng et al.

Agric. Food Chem.

(2012)

J.F. Prescott et al.

(1993)

K. Kumar et al.

Adv. Agron.

(2005)

Cited by (61)

An improved gravimetric method with anti-solvent addition to measure the solubility of D-allulose in water
2023, Journal of Food Engineering
Anti-solvent assisted gravimetric (AAG) method as a novel approach was proposed to accelerate solubility measurement. The new method was to add the anti-solvent into the saturated solution to drive a fast crystallization, and then to evaporate the filtered solution in order to collect the residual solid particles that were added with dried filter cake particles to constitute the total mass of solute in the initial saturated solution. The solubility of d-allulose, as a model compound, was measured by AAG method at temperature of 283.15–353.15 K. Moreover, the measurement by AAG method had a higher processing efficiency and more convenient operation than the traditional gravimetric method, which perform better in the solubility measurement of most viscous systems.
Solid-liquid phase equilibrium of adiphenine hydrochloride in twelve pure solvents
2023, Journal of Chemical Thermodynamics
The solubility and apparent thermodynamic properties of Adiphenine hydrochloride (ADH) (Form I) in twelve mono-solvents including methyl acetate, ethyl acetate, n-propyl acetate, n-butyl acetate, n-amyl acetate, isopropyl acetate, isobutyl acetate, n-hexanol, n-heptanol, n-octanol, anisole and acetone were reported in this work. The solubility of ADH (Form I) was quantified by the laser monitoring method at atmospheric pressure and the selected temperature ranged from 278.15 K to 323.15 K. In the same solvent, the lower the temperature is, the less the solubility of ADH (Form I) is. A maximum mole fraction solubility of ADH (Form I) existed in n-hexanol (0.2241) at 323.15 K while the minimum mole fraction solubility (1.139 × 10⁻⁴) appeared in isopropyl acetate at 278.15 K. The experimental values of solubility were fitted by modified Apelblat model, NRTL model and UNIQUAC model, and it was found that the calculated values of the NRTL model and the modified Apelblat model were closer to the experimental values. The dipolarity/polarizability of the solvent and the acidity of the hydrogen bonds both play a positive role in increasing the solubility of ADH (Form I). The apparent thermodynamic properties of the dissolution process of ADH (Form I) were analyzed by the van't Hoff equation. It can be found that the dissolution process is an entropy-driven endothermic processes.
Solubility, MD simulation, thermodynamic properties and solvent effect of perphenazine (Form I) in eleven neat organic solvents ranged from 278.15 K to 318.15 K
2022, Journal of Molecular Liquids
Citation Excerpt :
Owing to detection is introduced into the laser monitoring method, which has the advantages of short time, high accuracy and high reliability, so this method was chosen to investigate the solubility of perphenazine (Form I). The laser dynamic measurement instrument used in this study is the same as that used in the literature [23-25]. The entire experimental measurement system is mainly composed of four parts: photoelectric transformer, laser transmitter, recorder and dissolving kettle with the jacket.
Perphenazine has rather effective in the treatment of mental illness. In this work, the solid-liquid equilibrium data of perphenazine in eleven organic neat solvents were determined by laser dynamic method under the atmospheric pressure and temperature range of 278.15 K ∼ 318.15 K. The selected solvents were n-propanol, n-butyl alcohol, methyl acetate, ethyl acetate, n-propyl acetate, n-amyl acetate, N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAC), acetone, 2-methoxyethanol, glycol ether, respectively. From the results, the solubility of perphenazine is all positively correlated with temperature. Separately, we have adopted the KAT-LSER model and molecular dynamics simulation to investigate the influence of solvent effects and solute-solvent interaction on solute solubility. Meanwhile, there were four activity coefficient models being used to correlate the solubility data and Average relative deviation of models are 4.13% (Margules model), 3.94% (NRTL model), 4.49% (NRTL-SAC model) and 3.06% (UNIQUAC model), respectively, all of which do not exceed 5%. It manifests that the four activity coefficient models can fit the experimental values well, in which the UNIQUAC model gives the best regression effect. Moreover, the apparent thermodynamic properties(△_solG°, △_solH° and △_solS°) of perphenazine in various solvents were calculated by Van’t Hoff equation. In accordance with the analysis and calculation of dissolution, the dissolution process is an endothermic entropy-driven process. This research can provide basic data for the crystallization process of perphenazine.
dl-isoprenaline hydrochloride solubility in four binary solvents at saturation: Thermodynamic analysis, Hansen solubility parameters and molecular simulation
2022, Journal of Molecular Liquids
The solubility properties of dl-isoprenaline hydrochloride (dl-IPN) in four kinds of binary-solvents systems {(n-propanol, n-butanol, 2-propoxyethanol and 2-butoxyethanol) + methanol} at temperature range of 278.15–323.15 K under 101.3 kPa was further investigated using the laser monitoring technique. According to the result about solubility of dl-IPN in these chosen binary solvents, it is obvious that dl-IPN is more soluble at higher temperature. Additionally, the solubility values of dl-IPN, in all the investigated binary solvent mixtures, is improved with increasing mass fraction of co-solvent (methanol). The Hansen solubility parameters (HSPs) interpretate reasonably the order of dl-IPN solubility in these binary-solvents systems. Furthermore, the molecular dynamic (MD) simulation is employed to describe the molecular interactions of the types solute–solvent and solvent–solvent, and the obtained results confirm that solute–solvent and solvent–solvent molecular interactions have deep impact on the solubility of dl-IPN. The obtained experimental data about the solubility of dl-IPN is fitted by five models (λh equation, Apelblat equation, Jouyban-Acree-Apelblat (J-A-A) model, Ma model and Sun model). The analysis of thermodynamic properties was based on the values of the calculated thermodynamic parameters. It can be concluded that the dl-IPN dissolution process is entropy-motivated and endothermal in all the investigated binary-solvents systems, and that the main contribution to Δ_disG^o is due to enthalpy.
Solid-liquid phase equilibrium of Nintedanib in ten pure solvents: Determination, thermodynamic analysis, model correlation and molecular simulation
2021, Journal of Chemical Thermodynamics
Citation Excerpt :
Moreover, all the ΔsolH° and ΔsolG° of Nintedanib in all the solvents were positive too. This proves that the dissolution of Nintedanib is an endothermic process [44]. From the records, we can also find out that the values are positive for ΔsolS° (with the relative standard uncertainties being 0.09) of Nintedanib in these solvents with the range being from 37.22 kJ·mol−1 to 119.18 kJ·mol−1, which makes it clear that it is entropy which drives the dissolution process of Nintedanib in the ten neat solvents.
The equilibrium solubility and thermodynamic properties of Nintedanib in solvents including methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, DMF, DMAC, 1,4-dioxane and dichlormethane have been reported. By using the laser monitoring method with T = (278.15–323.15) K and p = 101.3 kPa, experiments for determinations of the solubility were carried out, from which it was proved that the mole fraction solubility of Nintedanib increased distinctly when the experimental temperature increased. The order of Nintedanib solubility in the above ten solvents was proved to be as follows: dichlormethane > DMAC > DMF > 1,4-dioxane > methanol > n-propanol > ethanol > n-butanol > iso-butanol > iso-propanol. The maximum mole fraction solubility of Nintedanib in dichloromethane was acquired (0.1314, T = 308.15 K); meanwhile, the minimum mole fraction solubility of Nintedanib in iso-propanol was acquired as well (4.4462 × 10⁻⁵, T = 278.15 K). Afterward, by using MD simulation, the results of the solute–solvent interaction proved that the solubility of Nintedanib in various solvents could be greatly affected by the interaction of the solute and solvent molecules, which showed that the dissolution behavior of Nintedanib in organic solvents was intricate. It also demonstrated that the solvent–solute interaction could be affected by factors of hydrogen bond acidity and the hydrogen bond donor propensities of the solvents. All records of Nintedanib solubility were regressed by using λh model, modified Apleblat model, Van't Hoff model and Yaws model. After comparing the results, it showed that the average 100ARD of the λh model was smaller than that of the other four models, which perfectly proved that the λh model was more suitable for connecting the solubility data. Moreover, Van't Hoff equation was adopted to calculate and study the apparent thermodynamic properties of Nintedanib in all the relevant solvents, from which the results indicated that the dissolution process of Nintedanib was a non-spontaneous and entropy-driven endothermic process.
Immunochromatographic assay for the detection of antibiotics in animal-derived foods: A review
2021, Food Control
Nowadays, adverse human reactions such as allergies and organ damage caused by antibiotics, as well as the drug resistance of bacteria have raised popular concern. Due to abuse in livestock production and aquaculture, many countries have established standards limiting the residual amounts of antibiotics in food. Therefore, it is necessary to develop analytical methods for the wholesale screening of antibiotics in animal-derived foods. Immunochromatographic assay (ICA) is suitable for simultaneously analyzing considerable numbers of samples at low cost, with high portability, and faster detection. This review introduces the current research status of ICA for eight categories of antibiotics including chloramphenicols (CAPs), tetracyclines (TCs), quinolones (QNs), sulfonamides (SAs), macrolides (MAs), aminoglycosides (AGs), lincosamides (LMs), and β-lactams in animal-derived foods. We summarize pre-treatment (extraction and clean-up) of ICA for the detection of antibiotics in animal-derived foods. Furthermore, the improved optimization strategies for weaknesses (low sensitivity and efficiency) are summarized. Trends in the development of ICA for detection of antibiotics are also reviewed.

View all citing articles on Scopus

View full text

Determination and correlation of solubility of tylosin tartrate in alcohol mixtures

Highlights

Abstract

Graphical abstract

Introduction

Section snippets

Materials

Solubility data

Conclusions

Fluid Phase Equilib.

Thermochim. Acta

Fluid Phase Equilib.

Fluid Phase Equilib.

J. Chem. Thermodyn.

J. Chem. Thermodyn.

Fluid Phase Equilib.

Fluid Phase Equilib.

Antibiot. Chemother.

Agric. Food Chem.

Adv. Agron.