ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Solubilities of Salicylic Acid in Pure Solvents and Binary Mixtures Containing Cosolvent

View Author Information
Department of Materials and Applied Chemistry, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan, and College of Pharmacy, Nihon University, 7-7-7 Narashinodai, Funabashi-shi, Chiba, 274-8555, Japan
* To whom correspondence should be addressed. Phone: +81-3-3259-0793. Fax: +81-3-3293-7572. E-mail address: [email protected]
†Part of the special issue “Robin H. Stokes Festschrift”.
‡Department of Materials and Applied Chemistry.
§College of Pharmacy.
Cite this: J. Chem. Eng. Data 2009, 54, 2, 480–484
Publication Date (Web):October 11, 2008
https://doi.org/10.1021/je800475d
Copyright © 2008 American Chemical Society

    Article Views

    2208

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Read OnlinePDF (91 KB)

    Abstract

    The solubility of salicylic acid in water, methanol, ethanol, ethyl acetate, polyethylene glycol (PEG) 300, and 1,4-dioxane and in various binary solvent mixtures, methanol + water, ethanol + water, ethanol + ethyl acetate, PEG 300 + water, and 1,4-dioxane + water, were determined using high-performance liquid chromatography (HPLC). The experimental solubility data were correlated by two local composition models: modified Wilson and nonrandom two-liquid (NRTL) 1.

    Cited By

    This article is cited by 40 publications.

    1. Masoud Sadeghi, Åke C. Rasmuson. Solubility of Salicylic Acid, Salicylamide, and Fenofibrate in Organic Solvents at Low Temperatures. Journal of Chemical & Engineering Data 2020, 65 (10) , 4855-4861. https://doi.org/10.1021/acs.jced.0c00443
    2. Rattavut Teerakapibal, Huayu Li, Brian Linehan, Fredrik L. Nordstrom. Material Impurity Distribution of Lattice-Incorporated Impurities in Salicylic Acid. Crystal Growth & Design 2020, 20 (3) , 1716-1728. https://doi.org/10.1021/acs.cgd.9b01460
    3. Fredrik L. Nordstrom, Brian Linehan, Rattavut Teerakapibal, Huayu Li. Solubility-Limited Impurity Purge in Crystallization. Crystal Growth & Design 2019, 19 (2) , 1336-1346. https://doi.org/10.1021/acs.cgd.8b01734
    4. Lijun Jia, Michael Svärd, and Åke C. Rasmuson . Crystal Growth of Salicylic Acid in Organic Solvents. Crystal Growth & Design 2017, 17 (6) , 2964-2974. https://doi.org/10.1021/acs.cgd.6b01415
    5. Mohammad A. A. Fakhree, Somaieh Ahmadian, Vahid Panahi-Azar, William E. Acree, Jr., and Abolghasem Jouyban . 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. Journal of Chemical & Engineering Data 2012, 57 (11) , 3303-3307. https://doi.org/10.1021/je300980k
    6. Jie Lu, Qing Lin, Zhen Li, and Sohrab Rohani . Solubility of l-Phenylalanine Anhydrous and Monohydrate Forms: Experimental Measurements and Predictions. Journal of Chemical & Engineering Data 2012, 57 (5) , 1492-1498. https://doi.org/10.1021/je201354k
    7. Berkant Kayan, Yu Yang, Edward J. Lindquist and A. Murat Gizir . Solubility of Benzoic and Salicylic Acids in Subcritical Water at Temperatures Ranging from (298 to 473) K. Journal of Chemical & Engineering Data 2010, 55 (6) , 2229-2232. https://doi.org/10.1021/je900769d
    8. Soma Khezri, Parisa Jafari, Elaheh Rahimpour, Abolghasem Jouyban. Enhancing the equilibrium solubility of salicylic acid in aqueous media by using polyethylene glycols 200, 400 and 600 as cosolvents: Correlation and dissolution thermodynamics. The Journal of Chemical Thermodynamics 2023, 186 , 107135. https://doi.org/10.1016/j.jct.2023.107135
    9. Sema Akay, Berkant Kayan, María Ángeles Peña, Abolghasem Jouyban, Fleming Martínez. Solubility of Salicylic Acid in Some (Ethanol + Water) Mixtures at Different Temperatures: Determination, Correlation, Thermodynamics and Preferential Solvation. International Journal of Thermophysics 2023, 44 (8) https://doi.org/10.1007/s10765-023-03224-z
    10. Parisa Jafari, Mohammad Barzegar-Jalali, Abolghasem Jouyban. Effect of temperature and composition on solubility and thermodynamics of salicylic acid in aqueous mixtures of betaine-based deep eutectic solvents. Korean Journal of Chemical Engineering 2023, 40 (4) , 910-924. https://doi.org/10.1007/s11814-022-1284-z
    11. Karima Bitchikh, Smakghi Nabil, Meniai Abdeslam-Hassen. Experimental Study and Modeling of Solid-liquid Equilibrium for Binary and Ternary Pharmaceutical and Food Systems. The Open Chemical Engineering Journal 2023, 17 (1) https://doi.org/10.2174/18741231-v17-e230111-2022-9
    12. Mohammad Barzegar-Jalali, Parisa Jafari, Salar Hemmati, Abolghasem Jouyban. Equilibrium solubility investigation and thermodynamic aspects of paracetamol, salicylic acid and 5-aminosalicylic acid in polyethylene glycol dimethyl ether 250 + water mixtures. Journal of Molecular Liquids 2023, 372 , 121185. https://doi.org/10.1016/j.molliq.2022.121185
    13. Fatemeh Nourizadeh, Masumeh Mokhtarpour, Zahra Valizadeh Ziaee, Mohammad Khorsandi, Asma Sadrmousavi, Hemayat Shekaari. Solubility enhancement and intermolecular interactions of salicylic acid in aqueous solutions of choline chloride based deep eutectic solvents. Journal of Molecular Liquids 2022, 367 , 120433. https://doi.org/10.1016/j.molliq.2022.120433
    14. Omid Faraz, Mozhdeh Poustchi, Ebrahim Nazari Denyani, Parsa Movahedi, Fereshteh Rajabi Kouchi, Reza Shahriari. Thermodynamic modeling of pharmaceuticals solubility in pure, mixed and supercritical solvents. Journal of Molecular Liquids 2022, 353 , 118809. https://doi.org/10.1016/j.molliq.2022.118809
    15. Samane Zarei Mahmoudabadi, Gholamreza Pazuki. Application of PC-SAFT EOS for Pharmaceuticals: Solubility, Co-Crystal, and Thermodynamic Modeling. Journal of Pharmaceutical Sciences 2021, 110 (6) , 2442-2451. https://doi.org/10.1016/j.xphs.2020.12.035
    16. Yuta Sugimoto, Masaki Ota, Yoshiyuki Sato, Richard Lee Smith, Hiroshi Inomata. Distribution coefficients of salicylic acid and methyl salicylate in high-pressure CO2 – water - ethanol systems. The Journal of Supercritical Fluids 2020, 166 , 105013. https://doi.org/10.1016/j.supflu.2020.105013
    17. Samane Zarei Mahmoudabadi, Gholamreza Pazuki. Investigation of COSMO-SAC model for solubility and cocrystal formation of pharmaceutical compounds. Scientific Reports 2020, 10 (1) https://doi.org/10.1038/s41598-020-76986-3
    18. Zahra Iqbal, Ausaf Ahmad, Ziyaul Haque, Mohammed S. Khan, Mohd S. Khan, Mohammed S. Iqbal. RP-HPLC Estimation of Flavonol Derivatives and Phenolic Acids in Capsicum annuum L. and their Correlation with In Vitro Anti-Inflammatory Activity. Current Pharmaceutical Biotechnology 2020, 21 (2) , 149-157. https://doi.org/10.2174/1389201020666190930115035
    19. T Rottiers, Van der B Bruggen, L Pinoy. Production of salicylic acid in a three compartment bipolar membrane electrodialysis configuration. Journal of Industrial and Engineering Chemistry 2017, 54 , 190-199. https://doi.org/10.1016/j.jiec.2017.05.033
    20. J. Seidel, J. Ulrich. Reprint of: Effects of solution degassing on solubility, crystal growth and dissolution–Case study: Salicylic acid in methanol. Journal of Crystal Growth 2017, 469 , 78-83. https://doi.org/10.1016/j.jcrysgro.2017.03.046
    21. Baptiste Bouillot, Theodora Spyriouni, Sébastien Teychené, Béatrice Biscans. Solubility of pharmaceuticals: A comparison between SciPharma, a PC-SAFT-based approach, and NRTL-SAC. The European Physical Journal Special Topics 2017, 226 (5) , 913-929. https://doi.org/10.1140/epjst/e2016-60225-5
    22. J. Seidel, J. Ulrich. Effects of solution degassing on solubility, crystal growth and dissolution—Case study: Salicylic acid in methanol. Journal of Crystal Growth 2017, 459 , 153-158. https://doi.org/10.1016/j.jcrysgro.2016.11.037
    23. Audrey L. Ingram, Tara M. Nickels, Dalia K. Maraoulaite, Robert L. White. Thermogravimetry-mass spectrometry investigations of salicylic acid and acetylsalicylic acid desorption from montmorillonites. Thermochimica Acta 2016, 639 , 120-129. https://doi.org/10.1016/j.tca.2016.07.016
    24. Michael H. Abraham, William E. Acree. Equations for the Partition of Neutral Molecules, Ions and Ionic Species from Water to Water–Methanol Mixtures. Journal of Solution Chemistry 2016, 45 (6) , 861-874. https://doi.org/10.1007/s10953-016-0479-5
    25. Zhihui Ai, Jilin Wang, Lizhi Zhang. Substrate-dependent photoreactivities of BiOBr nanoplates prepared at different pH values. Chinese Journal of Catalysis 2015, 36 (12) , 2145-2154. https://doi.org/10.1016/S1872-2067(15)60986-X
    26. Hiroyuki Matsuda, Kanako Mori, Mariko Tomioka, Nozomi Kariyasu, Toshiro Fukami, Kiyofumi Kurihara, Katsumi Tochigi, Kazuo Tomono. Determination and prediction of solubilities of active pharmaceutical ingredients in selected organic solvents. Fluid Phase Equilibria 2015, 406 , 116-123. https://doi.org/10.1016/j.fluid.2015.07.032
    27. José Rodrigo Vergara‐Salinas, José Cuevas‐Valenzuela, José R. Pérez‐Correa. Pressurized hot water extraction of polyphenols from plant material. 2015, 63-101. https://doi.org/10.1002/9781118733103.ch3
    28. Donal Mealey, Denise M. Croker, Åke C. Rasmuson. Crystal nucleation of salicylic acid in organic solvents. CrystEngComm 2015, 17 (21) , 3961-3973. https://doi.org/10.1039/C4CE01428F
    29. Hakmin Kim, Junhyuk Lim, Jung Hyun Hong, Ah Reum Kim, Moon Sam Shin, Hwayong Kim. Solubility of climbazole in various alcohols at different temperatures. The Journal of Chemical Thermodynamics 2014, 77 , 1-6. https://doi.org/10.1016/j.jct.2014.04.011
    30. William E. Acree. IUPAC-NIST Solubility Data Series. 102. Solubility of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) in Neat Organic Solvents and Organic Solvent Mixtures. Journal of Physical and Chemical Reference Data 2014, 43 (2) https://doi.org/10.1063/1.4869683
    31. Yuma Naito, Hiroyuki Matsuda, Kazuya Shimomura, Kiyofumi Kurihara, Katsumi Tochigi, Kazuo Tomono. Measurement and correlation of solubilities of the poorly water-soluble pharmaceutical compound etodolac by addition of co-solvents. Fluid Phase Equilibria 2013, 357 , 43-49. https://doi.org/10.1016/j.fluid.2013.05.025
    32. William E. Acree. IUPAC-NIST Solubility Data Series. 99. Solubility of Benzoic Acid and Substituted Benzoic Acids in Both Neat Organic Solvents and Organic Solvent Mixtures. Journal of Physical and Chemical Reference Data 2013, 42 (3) https://doi.org/10.1063/1.4816161
    33. Junhyuk Lim, Sunghyun Jang, Hye Kyoung Cho, Moon Sam Shin, Hwayong Kim. Solubility of salicylic acid in pure alcohols at different temperatures. The Journal of Chemical Thermodynamics 2013, 57 , 295-300. https://doi.org/10.1016/j.jct.2012.09.006
    34. Mariam Saifullah, Shulin Ye, Laura M. Grubbs, Nohelli E. De La Rosa, William E. Acree, Michael H. Abraham. Abraham Model Correlations for Transfer of Neutral Molecules to Tetrahydrofuran and to 1,4-Dioxane, and for Transfer of Ions to Tetrahydrofuran. Journal of Solution Chemistry 2011, 40 (12) , 2082-2094. https://doi.org/10.1007/s10953-011-9776-1
    35. Michael H. Abraham, William E. Acree. Partition Coefficients and Solubilities of Compounds in the Water–Ethanol Solvent System. Journal of Solution Chemistry 2011, 40 (7) , 1279-1290. https://doi.org/10.1007/s10953-011-9719-x
    36. Abolghasem Jouyban, Vahid Panahi-Azar, Fatemeh Khonsari. Solubility of salicylic acid in ethanol, propylene glycol, and N-methyl-2-pyrrolidone at various temperatures and their binary mixtures at 298.2K. Journal of Molecular Liquids 2011, 160 (1) , 14-16. https://doi.org/10.1016/j.molliq.2011.02.001
    37. Hiroyuki Matsuda, Sho Matsumoto, Kenta Kaguragi, Kiyofumi Kurihara, Katsumi Tochigi, Kazuo Tomono. Determination and correlation of solubilities of famotidine in water+co-solvent mixed solvents. Fluid Phase Equilibria 2011, 302 (1-2) , 115-122. https://doi.org/10.1016/j.fluid.2010.09.029
    38. Hiroyuki Matsuda, Kenta Kaburagi, Kiyofumi Kurihara, Katsumi Tochigi, Kazuo Tomono. Prediction of solubilities of pharmaceutical compounds in water+co-solvent systems using an activity coefficient model. Fluid Phase Equilibria 2010, 290 (1-2) , 153-157. https://doi.org/10.1016/j.fluid.2009.08.021
    39. . Solubility Data in Organic Solvents. 2009, 69-202. https://doi.org/10.1201/9781439804889-c2
    40. . Solubility Data in Binary Solvent Mixtures. 2009, 203-505. https://doi.org/10.1201/9781439804889-c3

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect