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 Page: 3,303
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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
Mohammad A. A. Fakhree,tt'# Somaieh Ahmadian,t't'# Vahid Panahi-Azar, William E. Acree, Jr.,l
and Abolghasem Jouyban*'*'
tDepartment of Molecular Cell Biology, Leiden University Medical Center, tDrug Applied Research Center and Faculty of Pharmacy,
and Liver and Gastrointestinal Diseases Research Center, Tabriz University of Medical Sciences, Tabriz 51664, Iran
IIDepartment of Chemistry, University of North Texas, Denton, Texas 76203-5070, United States
'Pharmaceutical Engineering Laboratory, School of Chemical Engineering, College of Engineering, University of Tehran, P.O. Box
11155/4563, Tehran, IranABSTRACT: 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 x1= 0.114, 0.167 of 1-propanol (1) + water (2) and x1= 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 2009, 54, 1168-1170).
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.- II
fX=x1ogC 5:1 gC I f r H) O
OH
*logCse
0.18
0.16
0.14
0.12
0.10
0.08
0.06
oo0s
0.04
0.02
0.00I
f 1-propanol (1) + water (2)
2-propanol (1) +water (2)
o x p-os i o1s0.8 2
0.4 0.6 0.8
xlINTRODUCTION
2-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
HO .O
OH
Figure 1. Chemical structure of salicylic acid.
an active metabolite of acetylsalicylic acid, shows anti-
inflammatory 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, pharmaceut-
ical, 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
ACS Publications 2012 American Chemical Society 3303monosolvents at different temperatures were reported for
water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-
butanol, 2-methyl-l-propanol, 2-methyl-2-propanol, 1-penta-
nol, 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, chloro-
form, 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 poly-
ethylene 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 glycol and 1,4-dioxane; propylene glycol and either
1,4-dioxane, chloroform, or ethyl acetate; 2-propanone and
either benzene, 1,4-dioxane, chloroform, or ethyl acetate; and
ethyl cellosolve and either benzene, 1,4-dioxane, chloroform, or
ethyl acetate.6 10
Received: September 9, 2012
Accepted: October 17, 2012
Published: October 25, 2012dx.doi.org/10.1 021/je300980k I J. Chem. Eng. Data 2012, 57, 3303-3307
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Fakhree, Mohammad Amin Abolghassemi; Ahmadian, Somaieh; Panahi-Azar, Vahid; Jouyban, Abolghasem & Acree, William E. (William Eugene). 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, article, October 25, 2012; [Washington, D.C.]. (https://digital.library.unt.edu/ark:/67531/metadc174731/m1/1/: accessed April 25, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT College of Arts and Sciences.