Solubility of 2-Hydroxybenzoic Acid in Select Organic Solvents at 298.15 K

Fina, Karina M. De; Sharp, Tina L.; Roy, Lindsay E.; Acree, William E.

doi:10.1021/je990134w

Cited by 23 publications

(16 citation statements)

References 11 publications

(17 reference statements)

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“…Table 2 lists the densities of the saturated solutions, experimental and correlated, solubility values of salicylic acid in water, 1-propanol, 2-propanol, and 2-propanone solutions at different temperatures. As expected, the solubility of salicylic 1 and 0.1817 1 respectively for 1-propanol, 2-propanol, and 2-propanone with the results of this work 0.132, 0.144, and 0.137 respectively for 1-propanol, 2-propanol, and 2-propanone reveal that there is almost agreement between them. As it is reported and discussed by Matsuda et al, there are considerable differences between reported solubility values for salicylic acid from different groups.…”

Section: ■ Introductionsupporting

confidence: 89%

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

Fakhree¹,

Ahmadian²,

Panahi‐Azar³

et al. 2012

J. Chem. Eng. Data

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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...

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Section: ■ Introductionsupporting

confidence: 89%

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

Fakhree¹,

Ahmadian²,

Panahi‐Azar³

et al. 2012

J. Chem. Eng. Data

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“…The concentration of each diluted solution was calculated from a BeerLambert law absorbance versus concentration curve generated from the measured absorbances of nine carefully prepared standard solutions of known solute concentration. The analysis wavelengths and concentration ranges used for each solute have been reported in our earlier publications [62][63][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78][79]. Molar concentrations were converted into mole fraction solubilities using the mass of the sample analyzed, molar masse of 2-butoxyethanol and the respective solutes, volume of the volumetric flasks, and any dilutions needed to get the measured absorbances on the Beer-Lambert law curve.…”

Section: Solubility Measurementsmentioning

confidence: 99%

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

Sedov

Stolov

Hart

et al. 2015

Journal of Molecular Liquids

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Infinite dilution activity coefficients (γ∞) were measured at 298 K for 12 different aliphatic hydrocarbons (alkanes, cycloalkanes, alkenes), 11 different aromatic compounds (benzene, alkylbenzenes, halobenzenes, naphthalene), and 2-chloro-2-methylpropane dissolved in 2-butoxyethanol at 298 K using a headspace gas chromatographic method. As part of the experimental study solubilities of 19 crystalline nonelectrolyte solutes (2-hydroxybenzoic acid, acetylsalicylic acid, 3,5-dinitro-2-methylbenzoic acid, acenaphthene, trans-stilbene, xanthene, phenothiazine, 3,5-dinitrobenzoic acid, 3-chlorobenzoic acid, 2-methylbenzoic acid, 4-chloro-3-nitrobenzoic acid, 2-chloro-5-nitrobenzoic acid, benzoic acid, 4-aminobenzoic acid, benzil, thioxanthen-9-one, 3-nitrobenzoic acid, fluoranthene, and diphenyl sulfone) were determined in 2-butoxyethanol at 298 K using a static, spectrophotometric method. The experimental values 2 were converted to gas-to-2-butoxyethanol, water-to-2-butoxyethanol partition coefficients, and molar solubility ratios using standard thermodynamic relationships. Abraham model correlations for solute transfer into 2-butoxyethanol were derived from the calculated partition coefficients and solubility ratios. The derived Abraham model describes the observed partition coefficient and solubility data to within 0.14 log units (or less).

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“…Molar concentrations of the diluted solutions were determined from a Beer-Lambert law absorbance versus concentration working curve for nine standard solutions of known concentration. The analysis wavelengths and concentration ranges used for each solute have been reported in earlier solubility publications [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38].…”

Section: Solubility Measurementsmentioning

confidence: 99%

Abraham model correlations for solute transfer into 2-methoxyethanol from water and from the gas phase

Hart

Grover

Zettl

et al. 2015

Journal of Molecular Liquids

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Solubility of 2-Hydroxybenzoic Acid in Select Organic Solvents at 298.15 K

Cited by 23 publications

References 11 publications

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

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

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

Abraham model correlations for solute transfer into 2-methoxyethanol from water and from the gas phase

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