Effect of choline chloride/ethylene glycol or glycerol as deep eutectic solvents on the solubility and thermodynamic properties of acetaminophen

Abstract To overcome low solubility of acetaminophen (ACP), deep eutectic solvents (DESs) based on choline chloride (ChCl) with glycerol (G) and ethylene glycol (EG) as green solvents have been used up to 0.8 mol fraction of DES at T = (298.15 to 313.15) K. Deep eutectic solvents were prepared by combination of the two components with the molar ratios: ChCl/G (1:2) and ChCl/EG (1:2). The solubility of ACP was measured in the aqueous DESs solutions at different temperatures. The solubility in these solvents was increased with increasing the weight fraction of DESs especially in ChCl/EG. The solubility data were correlated by modified Apelblat, λh (Buchowski), Yalkowsky, NRTL, Wilson and UNIQUAC models. In addition, to study the interactions between the components, the thermodynamic properties including volumetric and compressibility have been investigated using density and speed of sound measurements. Also the thermodynamic functions, Gibbs energy, enthalpy, and entropy of dissolution and mixing were obtained. The solubility data of ChCl/EG is more effective on the ACP solubility rather than the DES containg glycerol. The calculated thermodynamic funtions also confirm the presence of strong solute–solvent interactions between ACP–DESs. The results also show that the main contribution for ACP solubility in the aqueous DES solutions is the enthalpy.

[1]  J. Prausnitz,et al.  LOCAL COMPOSITIONS IN THERMODYNAMIC EXCESS FUNCTIONS FOR LIQUID MIXTURES , 1968 .

[2]  A. Müllertz,et al.  Optimization of self nanoemulsifying drug delivery system for poorly water-soluble drug using response surface methodology , 2013, Drug development and industrial pharmacy.

[3]  Chun-Yan Jia,et al.  Solubility of Potassium Clavulanate in Ethanol, 1-Propanol, 1-Butanol, 2-Propanol, and 2-Methyl-1-propanol between 273 K and 305 K , 2005 .

[4]  Raymond K. Rasheed,et al.  Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. , 2001, Chemical communications.

[5]  Rahmat Sadeghi,et al.  Thermodynamics of the ternary systems: (water + glycine, l-alanine and l-serine + di-ammonium hydrogen citrate) from volumetric, compressibility, and (vapour + liquid) equilibria measurements , 2011 .

[6]  H. Høiland,et al.  Isentropic apparent molal compressibilities and compressibilities of ionization of carboxylic acids in aqueous solution , 1976 .

[7]  F. Martínez,et al.  Solubility and preferential solvation of acetaminophen in methanol + water mixtures at 298.15 K , 2016 .

[8]  E. Su,et al.  Significantly improving the solubility of non-steroidal anti-inflammatory drugs in deep eutectic solvents for potential non-aqueous liquid administration , 2016 .

[9]  W. Acree,et al.  Thermodynamic studies of fluphenazine decanoate solubility in PEG 200 + water mixtures , 2012 .

[10]  Åke C. Rasmuson,et al.  Solubility of Paracetamol in Pure Solvents , 1999 .

[11]  S. Romero,et al.  Enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide, and nalidixic acid in dioxane-water. , 1998, Journal of pharmaceutical sciences.

[12]  P. Liu,et al.  Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions , 2015 .

[13]  H. Buchowski,et al.  Solvent activity along a saturation line and solubility of hydrogen-bonding solids , 1980 .

[14]  F. Martínez,et al.  Preferential solvation of acetaminophen in ethanol + water solvent mixtures according to the inverse Kirkwood-Buff integrals method , 2013 .

[15]  S. Sarmad,et al.  Effect of tri-potassium phosphate on volumetric, acoustic, and transport behaviour of aqueous solutions of 1-ethyl-3-methylimidazolium bromide at T = (298.15 to 318.15) K , 2010 .

[16]  E. C. Abdullah,et al.  Solubility of stearic acid in various organic solvents and its prediction using non-ideal solution models , 2007 .

[17]  Raymond K. Rasheed,et al.  Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. , 2004, Journal of the American Chemical Society.

[18]  Y. Marcus,et al.  Solubility and preferential solvation of indomethacin in 1,4-dioxane+water solvent mixtures , 2010 .

[19]  David L Davies,et al.  Novel solvent properties of choline chloride/urea mixtures. , 2003, Chemical communications.

[20]  J. Prausnitz,et al.  Statistical thermodynamics of liquid mixtures: A new expression for the excess Gibbs energy of partly or completely miscible systems , 1975 .

[21]  F. Martínez,et al.  Thermodynamic Study of the Solubility of Some Sulfonamides in Octanol, Water, and the Mutually Saturated Solvents , 2001 .

[22]  A. Hossain,et al.  Effects of thermodynamics on the solvation of amino acids in the pure and binary mixtures of solutions: A review , 2017 .

[23]  F. Martínez,et al.  Thermodynamic study of the solubility of acetaminophen in propylene glycol + water cosolvent mixtures , 2006 .

[24]  Mohammed Taghi Zafarani-Moattar,et al.  Apparent molar volume and isentropic compressibility of ionic liquid 1-butyl-3-methylimidazolium bromide in water, methanol, and ethanol at T = (298.15 to 318.15) K , 2005 .

[25]  A. Pal,et al.  Interactions of Diglycine in Aqueous Saccharide Solutions at Varying Temperatures: A Volumetric, Ultrasonic and Viscometric Study , 2010 .

[26]  J. Gauchi,et al.  Polymorphism of paracetamol: relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressure-temperature and temperature-volume phase diagrams. , 2005, Journal of pharmaceutical sciences.

[27]  A. Laesecke,et al.  Advanced calibration, adjustment, and operation of a density and sound speed analyzer , 2013 .

[28]  L. Goodman,et al.  The Pharmacological Basis of Therapeutics , 1941 .

[29]  B. K. Hodnett,et al.  Solubility of Form III Piracetam in a Range of Solvents , 2010 .

[30]  Julia L. Shamshina,et al.  Liquid forms of pharmaceutical co-crystals: exploring the boundaries of salt formation. , 2011, Chemical communications.

[31]  Partha Sarathi Guin,et al.  Role of electrolytes in the solubility of l-proline and its transfer free energetics , 2016 .

[32]  S. Romero,et al.  The Behavior of Paracetamol in Mixtures of Amphirotic and Amphiprotic-Aprotic Solvents. Relationship of Solubility Curves to Specific and Nonspecific Interactions , 1996 .

[33]  Masumeh Mokhtarpour,et al.  Solubility, volumetric and compressibility properties of acetaminophen in some aqueous solutions of choline based deep eutectic solvents at T = (288.15 to 318.15) K , 2017, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[34]  M. Nagarsenker,et al.  Formulation and In Vivo Evaluation of Self-Nanoemulsifying Granules for Oral Delivery of a Combination of Ezetimibe and Simvastatin , 2008 .

[35]  K. Tochigi,et al.  Determination and prediction of solubilities of active pharmaceutical ingredients in selected organic solvents , 2015 .

[36]  S. Yalkowsky,et al.  Handbook of aqueous solubility data , 2003 .

[37]  I. Alnashef,et al.  Are deep eutectic solvents benign or toxic? , 2013, Chemosphere.

[38]  G. M. Wilson,et al.  Vapor-Liquid Equilibrium. XI. A New Expression for the Excess Free Energy of Mixing , 1964 .

[39]  Emma L. Smith,et al.  Deep eutectic solvents (DESs) and their applications. , 2014, Chemical reviews.

[40]  Rahmat Sadeghi,et al.  Volumetric and Acoustic Properties of Aqueous Carbohydrate–Polymer Solutions , 2016 .

[41]  Dongwei Wei,et al.  Effect of temperature on the solubility of 3-aminopyridine in binary ethanol + toluene solvent mixtures , 2012 .

[42]  R. Strickley.  Solubilizing Excipients in Oral and Injectable Formulations , 2004, Pharmaceutical Research.

[43]  Jianji Wang,et al.  Effect of temperature on volumetric and viscosity properties of some α-amino acids in aqueous calcium chloride solutions , 2004 .

[44]  S. Roy,et al.  Thermodynamic solvation of a series of homologous α-amino acids in non-aqueous mixture of ethylene-glycol and N,N-dimethyl formamide , 2011 .

[45]  F. Martínez,et al.  Solubility of Carvedilol in Ethanol + Propylene Glycol Mixtures at Various Temperatures , 2013 .

[46]  A. Hossain,et al.  Solubility of DL-serine and DL-phenylalanine in aqueous mixtures of dimethyl sulfoxide and solvation thermodynamics , 2015 .

[47]  R. Bogel-Łukasik,et al.  A favourable solubility of isoniazid, an antitubercular antibiotic drug, in alternative solvents , 2012 .

[48]  F. Martínez,et al.  Solubility of drugs in ethyl acetate-ethanol mixtures at various temperatures , 2012 .

[49]  Tomi Raatikainen,et al.  Application of several activity coefficient models to water-organic-electrolyte aerosols of atmospheric interest , 2005 .

[50]  Liying Qin,et al.  Solubility and Solution Thermodynamics of Betaine in Different Pure Solvents and Binary Mixtures , 2012 .

[51]  L. Hepler.  Thermal expansion and structure in water and aqueous solutions , 1969 .

[52]  C. Chiappe,et al.  Are ionic liquids a proper solution to current environmental challenges , 2014 .

[53]  J. Wang,et al.  Solubility of 16α,17α-Epoxyprogesterone in Six Different Solvents , 2005 .

[54]  Jinglan Wu,et al.  Solubility of l-phenylalanine in water and different binary mixtures from 288.15 to 318.15K , 2012 .

[55]  H. Eshghi,et al.  Deep eutectic solvent for multi-component reactions: a highly efficient and reusable acidic catalyst for synthesis of 2,4,5-triaryl-1H-imidazoles , 2015, Research on Chemical Intermediates.

[56]  Pei-sheng Ma,et al.  The effect of temperature on the solubility of benzoic acid derivatives in water , 2006 .

[57]  F. Mjalli,et al.  Zinc (II) chloride-based deep eutectic solvents for application as electrolytes: Preparation and characterization , 2015 .

[58]  J. S. Rowlinson,et al.  Molecular Thermodynamics of Fluid-Phase Equilibria , 1969 .

[59]  H. Shekaari,et al.  Effect of ionic liquid, 1-octyl-3-methylimidazolium bromide on the thermophysical properties of aqueous d-glucose solutions at 298.15K , 2011 .

[60]  Bhupinder Singh,et al.  Optimized self nano-emulsifying systems of ezetimibe with enhanced bioavailability potential using long chain and medium chain triglycerides. , 2012, Colloids and surfaces. B, Biointerfaces.

[61]  E. Voutsas,et al.  Separation of the ethanol/water azeotropic mixture using ionic liquids and deep eutectic solvents , 2016 .

[62]  François Jérôme,et al.  Deep eutectic solvents: syntheses, properties and applications. , 2012, Chemical Society reviews.

[63]  Kenneth S. Pitzer,et al.  ELECTROLYTES: FROM DILUTE SOLUTIONS TO FUSED SALTS , 1980 .

[64]  S. Stolte,et al.  Toxicity and biodegradability of dicationic ionic liquids , 2014 .

[65]  H. Shekaari,et al.  Solvation properties of acetaminophen in aqueous ionic liquid, 1-hexyl-3-methylimidazolium bromide, solutions at different temperatures , 2015 .

[66]  Alexander Apelblat,et al.  Solubilities ofo-acetylsalicylic, 4-aminosalicylic, 3,5-dinitrosalicylic, andp-toluic acid, and magnesium-DL-aspartate in water fromT=(278 to 348) K , 1999 .

[67]  D. Reid,et al.  Thermodynamic studies of dilute aqueous solutions of cyclic ethers and simple carbohydrates , 1972 .