Solubility of 2-Hydroxybenzoic Acid in Water, 1-Propanol, 2-Propanol, and 2-Propanone at (298.2 to 338.2) K and Their Aqueous Binary Mixtures at 298.2 K

Abstract

Solubility of 2-hydroxybenzoic acid (salicylic acid, with measured melting point of 432 K) in water, 1-propanol, 2-propanol, and 2-propanone was determined at (298.2 to 338.2) K and atmospheric pressure. Also, the solubility of salicylic acid in binary mixtures of 1-propanol (1) + water (2), 2-propanol (1) + water (2), and 2-propanone (1) + water (2) at 298.2 K and atmospheric pressure was investigated. Phase separation occurred in x 1 = 0.114, 0.167 of 1-propanol (1) + water (2) and x 1 = 0.171, 0.237 of 2-propanone (1) + water (2) mixtures. The van't Hoff and Grant equations were used to correlate the solubility of salicylic acid in monosolvents at different temperatures. The solubility values of salicylic acid in binary mixtures of solvents were calculated using the Jouyban−Acree model (J. Chem. Eng. Data 2009Data , 54, 1168Data −1170. The mean deviation was used as an error criterion. The overall mean deviation of correlated solubility data in monosolvents at different temperatures, and in mixed solvents at 298.2 K were 1.0 % and 8.3 %, respectively. ■ INTRODUCTION2-Hydroxybenzoic or salicylic acid, a phenolic acid compound, is a metabolite of salicin, one of the most ancient pain relievers extracted from the bark of willow (Figure 1). Salicylic acid, also an active metabolite of acetylsalicylic acid, shows antiinflammatory effects and is used in topical formulations as a chemical exfoliating agent. It is used in the organic synthesis of many other medicinal compounds including salicylates (its ester and salt derivatives) and acetylsalicylic acid (Aspirin). In recent years, it has been used in cocrystal synthesis of medicinal compounds with a desirable increase in solubility properties. Hence, solubility data of this compound might be of interest for chemists and formulator researchers in chemical, pharmaceutical, food, and cosmetic industries.There are a number of previously reported solubility data for salicylic acid in monosolvents and mixtures of solvents at different temperatures. Solubility data for salicylic acid in monosolvents at different temperatures were reported for water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol, 1-pentanol, 1-octanol, dibutyl ether, ethylene glycol, propylene glycol, glycerin, acetone, ethyl acetate, butyl acetate, acetic acid, ethyl cellosolve, 1,4-dioxane, tetrahydrofuran, 2-propanone, 2-butanone, cyclohexanone, cyclohexanol, acetonitrile, chloroform, carbon tetrachloride, benzene, benzyl alcohol, and xylene.1−7 Salicylic acid solubility data in mixtures of solvents were reported for water and either methanol, ethanol, 1-propanol, 2-propanone, 2-ethoxyethanol, 1,4-dioxane, or polyethylene glycol 300; methanol and either benzene, 1,4-dioxane, chloroform, or ethyl acetate; ethanol and either benzene, 1,4-dioxane, chloroform, or ethyl acetate; 1-propanol and either benzene, 1,4-dioxane, chloroform, or ethyl acetate; 1-butanol and either benzene, 1,4-dioxane, chloroform, or ethyl acetate; ethylene glyco...

Solubility of pharmaceuticals: A comparison between SciPharma, a PC-SAFT-based approach, and NRTL-SAC

“…Finally, in Figure 6 are shown the experimental [46,47] and calculated solubilities of salicylic acid in aqueous mixtures of propanol and 1,4-dioxane. Solubility in pure propanol and 1,4-dioxane solvents is not known to the models.…”

Prediction of deferiprone solubility in some non-aqueous binary solvent mixtures at various temperatures

“…As described earlier, J i terms could be computed at 298.2 K, and then could be used to predict the solubility at other temperatures and the only required data for these predictions are the solubility of the solute in the mono-solvents at temperature of interest [26,[28][29][30]. To solve this limitation, it is possible to combine the trained versions of the Jouyban-Acree model using whole data points (from Table 2) and the van't Hoff equation taken from previous works [14,15] for providing predictive models for solubility prediction of DFP in EG + PG, EG + PEG 400, EG + NMP and EG + EtOH mixtures at various temperatures as: …”

“…From a mathematical viewpoint, it is possible to compute J i terms at one temperature, and employ these constants for solubility prediction of pharmaceutical compounds in the binary mixtures at other temperatures by using the solubility data in the mono-solvents as input values as has been shown in earlier works [14,15,[21][22][23][24][25][26]. This numerical method provided acceptable and accurate predictions however two data points are required at each temperature of interest.…”

Solubility and preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in propylene glycol+water mixtures at 298.15K

“…(2) could be used to predict the solute solubility at various temperatures after training by solubility data of the solute in binary solvents at 298.15 K as shown in earlier works [15][16][17]. It is obvious that Eq.…”