Abstract
This paper investigates the reactive extraction of gallic acid (HGA) by trioctlyphosphine oxide (TOPO) in different kinds of solvents. The physical extraction studies only with conventional solvents have been carried out to understand the effect of extractant TOPO. The reactive extraction results have been evaluated in terms of the extraction efficiency, the distribution coefficient, and the loading factor. TOPO gave the highest extraction efficiency of 92% in the presence of oleyl alcohol, followed by dimethyl adipate and n-hexane. The complexation constants were estimated by the mass action law model. The model results demonstrated a realistic agreement with the experimental results. The solvent toxicity towards microorganisms has been discussed with solvent lipophilicity (log10 Pa). The number of theoretical units (NTU) and the actual solvent to feed (S/F) ratio were calculated from the experimental outcomes for further design of a liquid–liquid reactive extraction column. A thermodynamic study was executed at varied temperatures to estimate the enthalpy, entropy and free Gibbs energy change of the reaction. Lastly, HGA diffusivities into solvents were calculated by Wilke–Chang and Reddy–Doraiswamy equations. This study provides a detailed investigation on the reactive extraction of HGA by TOPO, and may be useful for its design and development.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Data availability
All data and materials are available in this manuscript.
References
Ahmad A, Othman I, Taher H, Banat F (2021) Lactic acid recovery from date pulp waste fermentation broth by ions exchange resins. Environ Technol Innov. https://doi.org/10.1016/j.eti.2021.101438
Almanasrah M, Brazinha C, Kallioinen M et al (2015) Nanofiltration and reverse osmosis as a platform for production of natural botanic extracts: the case study of carob by-products. Sep Purif Technol 149:389–397. https://doi.org/10.1016/j.seppur.2015.06.008
Antony FM, Wasewar KL (2018a) Reactive separation of protocatechuic acid using tri-n-octyl amine and di-(2-ethylhexyl) phosphoric acid in methyl isobutyl ketone. Sep Purif Technol 207:99–107. https://doi.org/10.1016/j.seppur.2018.06.037
Antony FM, Wasewar K (2018b) Separation of protocatechuic acid using di-(2-ethylhexyl)phosphoric acid in isobutyl acetate, toluene, and petroleum ether. J Chem Eng Data 63:587–597. https://doi.org/10.1021/acs.jced.7b00797
Antony FM, Wasewar K (2020) Effect of temperature on equilibria for physical and reactive extraction of protocatechuic acid. Heliyon 6:e03664. https://doi.org/10.1016/j.heliyon.2020.e03664
Ashok PK, Upadhyaya K (2012) Tannins are astringent. J Pharmacogn Phytochem 1:45–50
Avcı A, İnci İ, Baylan N (2019) A comparative adsorption study with various adsorbents for the removal of ciprofloxacin hydrochloride from water. Water Air Soil Pollut. https://doi.org/10.1007/s11270-019-4315-6
Baylan N (2020) Removal of levulinic acid from aqueous solutions by clay nano-adsorbents: equilibrium, kinetic, and thermodynamic data. Biomass Convers Biorefin 10:1291–1300. https://doi.org/10.1007/s13399-020-00744-8
Bhoite RN, Navya PN, Murthy PS (2013) Statistical optimization of bioprocess parameters for enhanced gallic acid production from coffee pulp tannins by penicillium verrucosum. Prep Biochem Biotechnol 43:350–363. https://doi.org/10.1080/10826068.2012.737399
Brink LES, Tramper J (1985) Optimization of organic solvent in multiphase biocatalysis. Biotechnol Bioeng 27:1258–1269. https://doi.org/10.1002/bit.260270822
Brouwer T, Blahusiak M, Babic K, Schuur B (2017) Reactive extraction and recovery of levulinic acid, formic acid and furfural from aqueous solutions containing sulphuric acid. Sep Purif Technol 185:186–195. https://doi.org/10.1016/j.seppur.2017.05.036
Bruce LJ, Daugulis AJ (1991) Solvent selection strategies for extractive biocatalysis. Biotechnol Prog 7:116–124. https://doi.org/10.1021/bp00008a006
Carvajal-Arroyo JM, Andersen SJ, Ganigué R et al (2021) Production and extraction of medium chain carboxylic acids at a semi-pilot scale. Chem Eng J. https://doi.org/10.1016/j.cej.2020.127886
Choubey S, Goyal S, Varughese LR et al (2018) Probing gallic acid for its broad spectrum applications. Mini-Rev Med Chem 18:1283–1293. https://doi.org/10.2174/1389557518666180330114010
Datta D, Babu BV, Kumar S (2017) Equilibrium and thermodynamic studies on reactive extraction of nicotinic acid using a biocompatible extraction system. J Chem Eng Data 62:3431–3436. https://doi.org/10.1021/acs.jced.7b00457
De BS, Wasewar KL, Dhongde VR et al (2018) Experimental and modeling of reactive separation of protocatechuic acid. Chem Eng Res Des 132:593–605. https://doi.org/10.1016/j.cherd.2018.01.054
De BS, Wasewar KL, Dhongde V, Mishra T (2019) A step forward in the development of in situ product recovery by reactive separation of protocatechuic acid. React Chem Eng 4:78–89. https://doi.org/10.1039/c8re00160j
Demir Ö, Gök A, Uslu H, Kırbaşlar Şİ (2021) Reactive extraction of cis, cis-muconic acid from aqueous solution using phosphorus-bonded extractants, tri-n-octylphosphineoxide and tri-n-butyl phosphate: equilibrium and thermodynamic study. Sep Purif Technol. https://doi.org/10.1016/j.seppur.2021.118899
Dhongde VR, De BS, Wasewar KL (2019) Experimental study on reactive extraction of malonic acid with validation by Fourier transform infrared spectroscopy. J Chem Eng Data 64:1072–1084. https://doi.org/10.1021/acs.jced.8b00972
Dhongde VR, De BS, Wasewar KL et al (2020) Experimental perspective for reactive separation of malonic acid using TBP in natural non-toxic solvents. J Ind Eng Chem 91:273–284. https://doi.org/10.1016/j.jiec.2020.08.011
Eda S, Borra A, Parthasarathy R et al (2018) Recovery of levulinic acid by reactive extraction using tri-n-octylamine in methyl isobutyl ketone: equilibrium and thermodynamic studies and optimization using Taguchi multivariate approach. Sep Purif Technol 197:314–324. https://doi.org/10.1016/j.seppur.2018.01.014
Francioso O, Sánchez-Cortés S, Casarini D et al (2002) Spectroscopic study of humic acids fractionated by means of tangential ultrafiltration. J Mol Struct 609:137–147. https://doi.org/10.1016/S0022-2860(01)00971-1
Hasret E, Klrbaşlar ŞI, Uslu H (2018) Extraction of citric acid and maleic acid from their aqueous solutions using a phosphorus-bonded extractant, tri-n-octylphosphineoxide, and a secondary amine, dioctylamine. J Chem Eng Data 63:39–48. https://doi.org/10.1021/acs.jced.7b00562
Hong LS, Ibrahim D, Kassim J, Sulaiman S (2011) Gallic acid: an anticandidal compound in hydrolysable tannin extracted from the barks of Rhizophora apiculata Blume. J Appl Pharm Sci 1:75–79
İnce E, Lalikoglu M, Constantinescu D (2014) Liquid phase equilibria of the water + acetic acid + dimethyl carbonate ternary system at several temperatures. J Chem Eng Data 59:3353–3358. https://doi.org/10.1021/je500332k
Joshi N, Keshav A, Poonia AK (2019) Reactive extraction of gallic acid using tributyl phosphate in different classes of diluents. J Chem Eng Data 64:2826–2835. https://doi.org/10.1021/acs.jced.9b00192
Keshav A, Wasewar KL, Chand S (2008) Equilibrium and kinetics of the extraction of propionic acid using tri-n-octylphosphineoxide. Chem Eng Technol 31:1290–1295. https://doi.org/10.1002/ceat.200700490
Keshav A, Wasewar KL, Chand S (2009) Recovery of propionic acid from an aqueous stream by reactive extraction: effect of diluents. Desalination 244:12–23. https://doi.org/10.1016/j.desal.2008.04.032
Kumar S, Babu BV (2008) Process intensification for separation of carboxylic acids from fermentation broths using reactive extraction. i-manager’s. J Future Eng Technol 3:21–28. https://doi.org/10.26634/jfet.3.3.643
Kumar S, Pandey S, Wasewar KL et al (2021) Reactive extraction as an intensifying approach for the recovery of organic acids from aqueous solution: a comprehensive review on experimental and theoretical studies. J Chem Eng Data 66:1557–1573. https://doi.org/10.1021/acs.jced.0c00405
Lalikoglu M (2022) Intensification of formic acid from dilute aqueous solutions using menthol based hydrophobic deep eutectic solvents. J Indian Chem Soc 99:100303. https://doi.org/10.1016/j.jics.2021.100303
Li S, Tang W, Shi P et al (2020) A new perspective of gallic acid on calcium oxalate nucleation. Cryst Growth Des 20:3173–3181. https://doi.org/10.1021/acs.cgd.0c00044
Liu X, Tanaka H, Yamauchi A et al (2005) Determination of lipophilicity by reversed-phase high-performance liquid chromatography: Influence of 1-octanol in the mobile phase. J Chromatogr A 1091:51–59. https://doi.org/10.1016/j.chroma.2005.07.029
Mahindrakar KV, Rathod VK (2020) Ultrasonic assisted aqueous extraction of catechin and gallic acid from Syzygium cumini seed kernel and evaluation of total phenolic, flavonoid contents and antioxidant activity. Chem Eng Process Process Intensif 149:107841. https://doi.org/10.1016/j.cep.2020.107841
Mukherjee S, Munshi B (2020) Experimental and theoretical analysis of reactive extraction of caproic acid by using TBP in green diluents. Chem Eng Process Process Intensif 153:107926. https://doi.org/10.1016/j.cep.2020.107926
Murali N, Srinivas K, Ahring BK (2017) Biochemical production and separation of carboxylic acids for biorefinery applications. Fermentation 3:1–25. https://doi.org/10.3390/fermentation3020022
Nawaz H, Shi J, Mittal GS, Kakuda Y (2006) Extraction of polyphenols from grape seeds and concentration by ultrafiltration. Sep Purif Technol 48:176–181. https://doi.org/10.1016/j.seppur.2005.07.006
Pandey S, Kumar S (2018) Reactive extraction of gallic acid using aminic and phosphoric extractants dissolved in different diluents: effect of solvent’s polarity and column design. Ind Eng Chem Res 57:2976–2987. https://doi.org/10.1021/acs.iecr.7b05110
Pardeshi S, Dhodapkar R, Kumar A (2014) Molecularly imprinted microspheres and nanoparticles prepared using precipitation polymerisation method for selective extraction of gallic acid from Emblica officinalis. Food Chem 146:385–393. https://doi.org/10.1016/j.foodchem.2013.09.084
Rewatkar K, Shende DZ, Wasewar KL (2016) Effect of temperature on reactive extraction of gallic acid using tri-n-butyl phosphate, tri-n-octylamine and Aliquat 336. J Chem Eng Data 61:3217–3224. https://doi.org/10.1021/acs.jced.6b00310
Rodrigues LM, Romanini EB, Silva E et al (2020) Camu-camu bioactive compounds extraction by ecofriendly sequential processes (ultrasound assisted extraction and reverse osmosis). Ultrason Sonochem 64:105017. https://doi.org/10.1016/j.ultsonch.2020.105017
Roy S, Olokede O, Wu H, Holtzapple M (2021) In-situ carboxylic acid separation from mixed-acid fermentation of cellulosic substrates in batch culture. Biomass Bioenergy 151:106165. https://doi.org/10.1016/j.biombioe.2021.106165
Serre E, Rozoy E, Pedneault K et al (2016) Deacidification of cranberry juice by electrodialysis: impact of membrane types and configurations on acid migration and juice physicochemical characteristics. Sep Purif Technol 163:228–237. https://doi.org/10.1016/j.seppur.2016.02.044
Toita M, Morita K, Hirayama N (2018) Formation of minimal third phase in ionic liquid extraction system with trioctylphosphine oxide and its possible application to extraction concentration. Anal Sci 34:1063–1065. https://doi.org/10.2116/analsci.18C016
Türk FN, Çehreli S, Baylan N (2021) Reactive extraction of monocarboxylic acids (formic, acetic, and propionic) using tributyl phosphate in green solvents (cyclopentyl methyl ether and 2-methyltetrahydrofuran). J Chem Eng Data 66:130–137. https://doi.org/10.1021/acs.jced.0c00486
Uslu H, Datta D (2015) Experimental and theoretical investigations on the reactive extraction of itaconic (2-methylidenebutanedioic) acid using trioctylamine (N,N-dioctyloctan-1-amine). J Chem Eng Data 60:1426–1433. https://doi.org/10.1021/je501131j
Waghmare MD, Wasewar KL, Sonawane SS, Shende DZ (2013) Reactive extraction of picolinic and nicotinic acid by natural non-toxic solvent. Sep Purif Technol 120:296–303. https://doi.org/10.1016/j.seppur.2013.10.019
Wasewar KL (2012) Reactive extraction: an intensifying approach for carboxylic acid separation. Int J Chem Eng Appl. https://doi.org/10.7763/ijcea.2012.v3.195
Funding
The authors gratefully acknowledge the financial support received from BAP (Project no.: FYL-2021-36067) from the İstanbul University-Cerrahpasa.
Author information
Authors and Affiliations
Contributions
SA: experimental section, ÖD: visualization, writing—original draft, AG: investigation, writing—original draft, ŞİK: writing—original draft, conceptualization, funding acquisition.
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Aras, S., Demir, Ö., Gök, A. et al. Reactive extraction of gallic acid by trioctylphosphine oxide in different kinds of solvents: equilibrium modeling and thermodynamic study. Braz. J. Chem. Eng. 40, 1171–1181 (2023). https://doi.org/10.1007/s43153-022-00292-w
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s43153-022-00292-w