Abstract
In order to design an efficient extraction system for the separation of biochemically produced trans-aconitic acid (TAH) from fermentation broth; equilibrium and kinetics of reactive extraction of TAH from aqueous solutions was investigated using tri-n-octylamine (TOA) as an extractant and sunflower oil as a diluent. Through the equilibrium studies stoichiometry (acid, extractant) of complex formations was determined with the help of loading ratio. Formation of (1, 1), (2, 1), & (3, 1) stoichiometry complexes were observed having complexation constants values 179.73 kmol−1 m3, 9512.58 kmol−2 m6, and 614,407.02 kmol−3 m9, respectively. Kinetics experiments were performed in Lewis type stirred cell and results confirmed that reaction between TAH and TOA in sunflower oil fall in regime 1, i.e. slow reaction occurring in bulk organic phase. The overall order of reaction is pseudo first order with rate constant (K mn ) 1.78 × 10−5 (kmol m−3)−0.71 s−1 and physical mass transfer coefficient (K l ) 4.22 × 10−5 m s−1.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: None declared.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
Amruta, T. M., D. P. Kiran, P. K. Shilpa, and S. T. Niraj. 2021. Recovery of Pyruvic Acid: A Theoretical Approach for Selection of Solvents for Reactive Extraction, Materials Today: Proceedings. https://doi.org/10.1016/j.matpr.2021.04.493 (in press).Search in Google Scholar
Connors, K. A. 1987. Binding Constants. The Measurement of Molecular Complex Stability. New York: John Wiley & Sons.Search in Google Scholar
Datta, D., and S. Kumar. 2013. “Equilibrium and Kinetic Studies of the Reactive Extraction of Nicotinic Acid with Tri-n-Octylamine Dissolved in MIBK.” Industrial & Engineering Chemistry Research 52 (41): 4680–6, https://doi.org/10.1021/ie401730v.Search in Google Scholar
Demir, Ö., A. Gök, H. Uslu, and Ş. İ. Kırbaşlar. 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.” Separation and Purification Technology 40: 118899, https://doi.org/10.1016/j.seppur.2021.118899.Search in Google Scholar
Doraiswamy, L. K., and M. M. Sharma. 1984. Heterogeneous Reactions: Analysis, Examples, and Reactor Design. New York: John Wiley & Sons.Search in Google Scholar
Hanna, G. J., and R. D. Noble. 1985. “Measurement of Liquid−Liquid Interfacial Kinetics.” Chemical Reviews 85: 583, https://doi.org/10.1021/cr00070a004.Search in Google Scholar
Holdom, K. S., and W. Norman. 1985. Fermentation Process for the Preparation of Aconitic. European Patent No EP0146378A3.Search in Google Scholar
Holdom, K. S., and W. Norman. 1988. Fermentation Process for the Preparation of Aconitic. U.S. Patent No 4,740,464.Search in Google Scholar
Jarvinen, M., L. Myllykoski, R. Keiski, and J. Sohlo. 2000. “Separation of Lactic Acid from Fermented Broth by Reactive Extraction.” Bioseparation 9 (3): 163–6, https://doi.org/10.1023/a:1008183322075.10.1023/A:1008183322075Search in Google Scholar
Joshi, N., A. Keshav, and A. K. Poonia. 2019. “Reactive Extraction of Gallic Acid Using Tributyl Phosphate in Different Classes of Diluents.” Journal of Chemical & Engineering Data 64: 2826–35, https://doi.org/10.1021/acs.jced.9b00192.Search in Google Scholar
Joshi, N., A. Keshav, and A. K. Poonia. 2020. Modeling and Optimization of Reactive Extraction Equilibria and Kinetic Study of Gallic Acid Using Tributyl Phosphate in Isoamyl Alcohol. Separation Science and Technology 56: 1035–46, https://doi.org/10.1080/01496395.2020.1751200.Search in Google Scholar
Jun, Y. S., Y. S. Huh, W. H. Hong, and Y. K. Hong. 2005. “Kinetics of the Extraction of Succinic Acid with Tri-n-Octylamine in 1-Octanol Solution.” Biotechnology Progress 21: 1673–9, https://doi.org/10.1021/bp050083t.Search in Google Scholar PubMed
Kobayashi, K., J. Maruebi, and K. Kirimura. 2016. “Bioproduction of trans-Aconitic Acid from Citric Acid by Whole-Cell Reaction of Escherichia coli Heterologously Expressing the Aconitate Isomerase Gene from Pseudomonas sp. Wu-0701.” Chemistry Select 1: 1467–71, https://doi.org/10.1002/slct.201600234.Search in Google Scholar
Kumar, T. P., B. Vishwanadham, K. N. P. Rani, M. Mallikarjun, and V. V. B. Rao. 2010. “Reactive Extraction of Levulinic Acid from Aqueous Solutions with Tri-n-octylamine (Toa) in 1-Octanol: Equilibria, Kinetics, and Model Development.” Chemical Engineering Communications 198 (4): 572–89, https://doi.org/10.1080/00986445.2010.512549.Search in Google Scholar
Keshav, A., K. Wasewar, and S. Chand. 2008. “Equilibrium and Kinetics of the Extraction of Propionic Acid Using Tri-n-octyl Phosphine Oxide.” Journal of Chemical Engineering and Technology 31: 1290–5, https://doi.org/10.1002/ceat.200700490.Search in Google Scholar
Kertes, A. S., and C. J. King. 1986. “Extraction Chemistry of Fermentation Product Carboxylic Acids.” Biotechnology and Bioengineering 28: 269–82, https://doi.org/10.1002/bit.260280217.Search in Google Scholar PubMed
Kumar, S., S. Pandey, K. L. Wasewar, N. Ak, and H. Uslu. 2021. “Reactive Extraction as an Intensifying Approach for the Recovery of Organic Acids from Aqueous Solution: A Comprehensive Review on Experimental and Theoretical Studies.” Journal of Chemical & Engineering Data 66: 1557–73, https://doi.org/10.1021/acs.jced.0c00405.Search in Google Scholar
Li, Q. Z., X. L. Jiang, X. J. Feng, Ji. M. Wang, C. Sun, H. B. Zhang, M. Xian, and H. Z. Li. 2017. “Recovery Processes of Organic Acids from Fermentation Broths in the Biomass-Based Industry.” Journal of Microbiology and Biotechnology 26: 1–8, https://doi.org/10.4014/jmb.1505.05049.Search in Google Scholar PubMed
Marti, M. E., T. Gurkan, and L. K. Doraiswamy. 2011. “Equilibrium and Kinetic Studies on Reactive Extraction of Pyruvic Acid with Trioctylamine in 1-Octanol.” Industrial & Engineering Chemistry Research 50: 13518–25, https://doi.org/10.1021/ie200625q.Search in Google Scholar
Pal, D., and A. Keshav. 2015. “Kinetics of Reactive Extraction of Pyruvic Acid Using Tributylamine Dissolved in n-Butyl Acetate.” International Journal of Chemical Reactor Engineering 13: 63–9, https://doi.org/10.1515/ijcre-2014-0117.Search in Google Scholar
Pandey, S., and S. Kumar. 2020. “Reactive Extraction of Gallic Acid from Aqueous Solution with Tri-n-octylamine in Oleyl Alcohol: Equilibrium, Thermodynamics and Optimization Using RSM-rCCD.” Separation and Purification Technology 231: 115904, https://doi.org/10.1016/j.seppur.2019.115904.Search in Google Scholar
Reddy, K. A., and L. K. Doraiswamy. 1967. “Estimating Liquid Diffusivity.” Industrial & Engineering Chemistry Fundamentals 6: 77–9, https://doi.org/10.1021/i160021a012.Search in Google Scholar
Swarnkar, A., A. B. Soni, and A. Keshav. 2016. “Kinetic Studies on Recovery of Acrylic Acid from Dilute Solutions.” Academic Journal of Science 06 (01): 163–70.Search in Google Scholar
Tamada, J. A., A. S. Kertes, and C. J. King. 1990. “Extraction of Carboxylic Acids with Amine Extractants. 1. Equilibria and Law of Mass Action Modeling.” Industrial & Engineering Chemistry Research 29 (7): 1319–26, doi:https://doi.org/10.1021/ie00103a035.Search in Google Scholar
Thakre, N., D. Datta, A. K. Prajapati, P. K. Chaudhari, and D. Pal. 2017. “Reactive Extraction of Citric Acid Using Different Extractants: Equilibrium, Kinetics and Modeling.” Chemical and Biochemical Engineering Quarterly 31: 437–46.10.15255/CABEQ.2016.859Search in Google Scholar
Türk, F. N., S. Çehreli, and N. Baylan. 2021. “Reactive Extraction of Monocarboxylic Acids (Formic, Acetic, and Propionic) Using Tributyl Phosphate in Green Solvents (Cyclopentyl Methyl Ether and 2-Methyltetrahydrofuran).” Journal of Chemical & Engineering Data 66: 130–7, https://doi.org/10.1021/acs.jced.0c00486.Search in Google Scholar
Uslu, H. 2006. “Linear Solvation Energy Relationship (LSER) Modeling and Kinetic Studies on Propionic Acid Reactive Extraction Using Alamine 336 in a Toluene Solution.” Industrial & Engineering Chemistry Research 45: 5788–95, https://doi.org/10.1021/ie060453y.Search in Google Scholar
Uslu, H. 2008. “Reactive Extraction of Levulinic Acid Using TPA in Toluene Solution: LSER Modeling, Kinetic and Equilibrium Studies.” Separation Science and Technology 43: 1535–48, https://doi.org/10.1080/01496390801941216.Search in Google Scholar
Uslu, H., D. Datta, D. Santos, H. S. Bamufleh, and C. Bayat. 2016. “Separation of 2,4,6-Trinitrophenol from Aqueous Solution by Liquid–Liquid Extraction Method: Equilibrium, Kinetics, Thermodynamics and Molecular Dynamic Simulation.” Chemical Engineering Journal 299: 342–52, https://doi.org/10.1016/j.cej.2016.04.080.Search in Google Scholar
Uslu, H., E. Baykal, A. Gök, Ş. İ. Kırbaşlar, and D. Santos. 2020. “Study on Oxalic Acid Extraction by Tripropylamine: Equilibrium and Computational COSMO-SAC Analysis.” Journal of Chemical & Engineering Data 65: 4347–53, https://doi.org/10.1021/acs.jced.9b01150.Search in Google Scholar
Wasewar, K. L., A. B. M. Heesink, G. F. Versteeg, and V. G. Pangarkar. 2002a. “Equilibria and Kinetics for Reactive Extraction of Lactic Acid Using Alamine 336 in Decanol.” Journal of Chemical Technology & Biotechnology 77 (9): 1068–75, https://doi.org/10.1002/jctb.680.Search in Google Scholar
Wasewar, K. L., A. B. M. Heesink, G. F. Versteeg, and V. G. Pangarkar. 2002b. “Reactive Extraction of Lactic Acid Using Alamine 336 in MIBK: Equilibria and Kinetics.” Journal of Biotechnology 97: 59–68, https://doi.org/10.1016/s0168-1656(02)00057-3.Search in Google Scholar
Wasewar, K. L., A. A. Yawalkar, J. A. Moulijn, and V. G. Pangarkar. 2004. “Fermentation of Glucose to Lactic Acid Coupled with Reactive Extraction: A Review.” Industrial & Engineering Chemistry Research 43: 5969, https://doi.org/10.1021/ie049963n.Search in Google Scholar
Wasewar, K., A. Keshav, and S. Chand. 2009. “Equilibrium and Kinetics of Propionic Acid Using Aliquat 336 and Tri-n-butylphosphate in n-Hexanol.” International Journal of Chemical Reactor Engineering 7 (A35): 1–19, https://doi.org/10.2202/1542-6580.1850.Search in Google Scholar
Wilke, C. R., and P. Chang. 1955. “Correlation of Diffusion Coefficient in Dilute Solutions.” AIChE Journal 1: 264, https://doi.org/10.1002/aic.690010222.Search in Google Scholar
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Articles in the same Issue
- Frontmatter
- Editorial
- Preface: Special issue dedicated to the International Conference on Reaction Engineering National Institute of Technology, Raipur, India
- Special Issue Article
- Semiconducting nanomaterials for photocatalytic desulfurization of liquid fuel under sunlight irradiation
- Optimization and experimental design by response surface method for reactive extraction of glutaric acid
- Equilibrium & kinetic studies of reactive extraction of trans-aconitic acid using sunflower oil with tri-n-octylamine
- Simulation of a kinetic model integrated with variable catalyst holdup applied in industrial fluid catalytic cracking risers
- Alkaline electro-hydrolysis pretreatment of rice straw for enhanced biogas production under ambient temperature
- Acclimatization studies for degradation of Acid Red 3BN dye and its treatment in moving bed biofilm reactor
- Value addition study on coker kero for producing alpha olefin and alkyl benzene
- Cyclic voltammetry to study kinetics of blast furnace slag and cerium dioxide modified electrode
Articles in the same Issue
- Frontmatter
- Editorial
- Preface: Special issue dedicated to the International Conference on Reaction Engineering National Institute of Technology, Raipur, India
- Special Issue Article
- Semiconducting nanomaterials for photocatalytic desulfurization of liquid fuel under sunlight irradiation
- Optimization and experimental design by response surface method for reactive extraction of glutaric acid
- Equilibrium & kinetic studies of reactive extraction of trans-aconitic acid using sunflower oil with tri-n-octylamine
- Simulation of a kinetic model integrated with variable catalyst holdup applied in industrial fluid catalytic cracking risers
- Alkaline electro-hydrolysis pretreatment of rice straw for enhanced biogas production under ambient temperature
- Acclimatization studies for degradation of Acid Red 3BN dye and its treatment in moving bed biofilm reactor
- Value addition study on coker kero for producing alpha olefin and alkyl benzene
- Cyclic voltammetry to study kinetics of blast furnace slag and cerium dioxide modified electrode