Issue
Korean Journal of Chemical Engineering,
Vol.37, No.12, 2307-2316, 2020
Natural deep eutectic solvents for enhancing the solubility of two B vitamins in aqueous solutions: Experimental study and thermodynamic aspects
Natural deep eutectic solvents (NADESs) as green solvents have substantial potential for enhancing the solubility of pharmaceuticals in aqueous solutions. In this work, the solubility of two B vitamins (nicotinic acid and 4aminobenzoic acid) in aqueous solutions of two NADESs was measured at temperatures between 298.15 K and 313.15 K and different concentrations of NADESs. The studied NADESs were prepared by mixing dried choline chloride with urea or malonic acid with molar ratios of 1 : 2 and 1 : 1, respectively. Based on the results, chloride+malonic acid was more effective on the solubility of the pharmaceuticals in aqueous solutions. Furthermore, the DESs increased the aqueous solubility of 4aminobenzoic acid more than that of nicotinic acid. The experimental solubility data were modeled with the van Laar activity model as well as the modified Apelblat equation to correlate the solubility of the pharmaceuticals to the temperature and NADESs concentration. The molar enthalpy of dissolution (Δhd) and the molar enthalpy of mixing (Δhmix) of the pharmaceuticals in the aqueous solutions of the NADESs were calculated. These parameters showed that all the dissolution processes were endothermic, while the mixing process as a part of the dissolution process was exothermic.
[References]
  1. Mehta M, Biopharmaceutics classification system (BCS): Development, implementation, and growth, Wiley, New Jersey (2016).
  2. Bouillot B, Teychene S, Biscans B, Fluid Phase Equilib., 309(1), 36, 2011
  3. Cheng C, Cong Y, Du CB, Wang J, Yao GB, Zhao HK, J. Chem. Thermodyn., 101, 372, 2016
  4. Mokhtarpour M, Shekaari H, Zafarani-Moattar MT, Golgoun S, J. Mol. Liq., 297, 111799, 2019
  5. Dhillon B, Goyal NK, Malviya R, Sharma PK, Glob. J. Pharmacol., 8, 26, 2014
  6. Chaudhary A, Nagaich U, Gulati N, Sharma VK, Khosa RL, J. Adv. Pharm. Educ. Res., 2, 32, 2012
  7. Kharwade M, Achyuta G, Subrahmanyam CVS, Puvvadi S, J. Pharm. Res., 5, 4204, 2012
  8. Smith KB, Bridson RH, Leeke GA, J. Chem. Eng. Data, 56(5), 2039, 2011
  9. Egorova KS, Gordeev EG, Ananikov VP, Chem. Rev., 117(10), 7132, 2017
  10. Faria RA, Bogel-Lukasik E, Fluid Phase Equilib., 397, 18, 2015
  11. Kudlak B, Owczarek K, Namiesnik J, Environ. Sci. Pollut. Res., 22, 11975, 2015
  12. Kunz W, Hackl K, Chem. Phys. Lett., 661, 6, 2016
  13. Jiang WJ, Zhong FY, Liu Y, Huang K, ACS Sustain. Chem. Eng., 7, 10552, 2019
  14. Wen Q, Chen JX, Tang YL, Wang J, Yang Z, Chemosphere, 132, 63, 2015
  15. Radosevic K, Curko N, Srcek VG, Bubalo MC, et al., LWT-Food Sci. and Technol., 73, 45, 2016
  16. Abbas Q, Binder L, ECS Trans., 33, 49, 2010
  17. Liu F, Chen W, Mi J, Zhang J, Kan X, Zhong F, Huang K, Zheng A, Jiang L, AIChE J., 65, e16574, 2019
  18. Jiang WJ, Zhong FY, Zhouo LS, Peng HL, Fan JP, Huang K, Chem. Commun., 56, 2399, 2020
  19. Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V, Chem. Commun., 2003, 70, 2003
  20. Dai Y, Van Spronsen J, Witkamp G, Anal. Chim. Acta, 766, 6, 2013
  21. Dai Y, Van Spronsen J, Witkamp GJ, Verpoorte R, Choi YH, J. Nat. Prod., 76, 2162, 2013
  22. Dai Y, Witkamp G, Verpoorte R, Choi YH, Food Chem., 187, 14, 2015
  23. Zhao H, Baker GA, Holmes S, J. Mol. Catal. B-Enzym., 72, 163, 2011
  24. Ni Y, Bi Z, Su H, Yan L, Green Chem., 21, 1075, 2019
  25. Shekaari H, Zafarani-Moattar MT, Shayanfar A, Mokhtarpour M, J. Mol. Liq., 249, 1222, 2018
  26. Tajmir F, Roosta A, J. Mol. Liq., 303, 112636, 2020
  27. Ghaedi H, Ayoub M, Sufian S, Murshid G, Farrukh S, Shariff AM, Int. J. Greenh. Gas Control, 66, 147, 2017
  28. Carlesi C, Guajardo N, Schrebler R, Vasquez-Sandoval D, J. Clean Prod., 240, 118240, 2019
  29. Lin CM, Leron RB, Caparanga AR, Li MH, J. Chem. Thermodyn., 68, 216, 2014
  30. Jiang H, Diao B, Xu D, Zhang L, Ma Y, Gao J, Wang Y, J. Mol. Liq., 279, 524, 2019
  31. Pan Q, Shang XY, Li J, Ma ST, Li LM, Sun L, Sep. Purif. Technol., 219, 113, 2019
  32. Soares RRG, Azevedo AM, Van Alstine JM, Aires-Barros MR, Biotechnol. J., 10, 1158, 2015
  33. Li C, Li Z, Wang A, Yin J, Wang J, Li H, Liu Q, RSC Adv., 3, 6356, 2013
  34. Xu P, Wang Y, Chen J, Wei X, Xu W, Ni R, Meng J, Zhou Y, Talanta, 202, 1, 2019
  35. Abbott AP, Ballantyne A, Harris RC, Juma JA, Ryder KS, Forrest G, Electrochim. Acta, 176, 718, 2015
  36. Sebastian P, Valles E, Gomez E, Electrochim. Acta, 112, 149, 2013
  37. Wang X, Sun M, Xiang S, Waqas M, Fan Y, Zhong J, Huang K, Chen W, Liu L, Yang J, Electrochim. Acta, 337, 135742, 2020
  38. Zhang X, Cheng L, Wu X, Tang Y, Wu Y, J. Environ. Sci., 33, 97, 2015
  39. Gano ZS, Mjalli FS, Al-Wahaibi T, Al-Wahaibi Y, AlNashef IM, Chem. Eng. Process. Process Intensif., 93, 10, 2015
  40. Jiang W, Dong L, Liu W, Guo T, Liu H, Yin S, Zhu W, Li H, Chem. Eng. Process. Process Intensif., 115, 34, 2017
  41. Juneidi I, Hayyan M, Hashim MA, Hayyan A, Biochem. Eng. J., 117, 129, 2017
  42. Halder AK, Cordeiro MNDS, ACS Sustain. Chem. Eng., 7, 10649, 2019
  43. Hayyan M, Hashim MA, Hayyan A, Al-Saadi MA, AlNashef IM, Mirghani MES, Saheed OK, Chemosphere, 90, 2193, 2013
  44. Macario IPE, Oliveira H, Menezes AC, Ventura SPM, Pereira JL, Goncalves AMM, Coutinho JAP, Goncalves FJM, Sci. Rep., 9, 3932, 2019
  45. Skarpalezos D, Detsi A, Appl. Sci., 9, 4169, 2019
  46. De Morais P, Goncalves F, Coutinho JAP, Ventura SPM, ACS Sustain. Chem. Eng., 3, 3398, 2015
  47. Prausnitz JM, Lichtenthaler RN, de Azevedo EG, Molecular thermodynamics of fluids-phase equilibria, 3rd Ed., Prentice-Hall, New Jersey (1999).
  48. Rehman M, Shekunov BY, York P, Colthorpe P, J. Pharm. Sci., 90, 1570, 2001
  49. Goncalves EM, da Piedade MEM, J. Chem. Thermodyn., 47, 362, 2012
  50. Lin HM, Nash RA, J. Pharm. Sci., 82, 1018, 1993
  51. Wu SH, Caparanga AR, Leron RB, Li MH, Thermochim. Acta, 544, 1, 2012
  52. Apelblat A, Manzurola E, Chem. Thermodyn., 31, 85, 1999
  53. Williamson AT, Trans. Faraday Soc., 40, 421, 1944
  54. Bellich B, Gamini A, Brady JW, Cesaro A, Int. J. Pharm., 540, 65, 2018
  55. Buchholz H, Seidel-Morgenstern A, Lorenz H, Chem. Eng. Technol., 40(7), 1268, 2017
  56. Wang LC, Wang FA, J. Chem. Eng. Data, 49(1), 155, 2004
  57. Lin HM, Nash RA, J. Pharm. Sci., 82, 1018, 1993
  58. Yalkowskyx SH, Valvani SC, Roseman TJ, J. Pharm. Sci., 72, 866, 1983
  59. Flynn GL, Yalkowsky SH, J. Pharm. Sci., 61, 838, 1972
  60. Jia Q, Ma P, Ma S, Wang C, J. Chem. Eng., 15, 710, 2007