Efficacy of tri-n-octylamine, tri-n-butyl phosphate and di-(2-ethylhexyl) phosphoric acid for reactive separation of protocatechuic acid

References

• Guglielmi, F.; Luceri, C.; Giovannelli, L.; Dolara, P.; Lodovici, M. (2003) Effect of 4-coumaric and 3,4-dihydroxybenzoic acid on oxidative DNA damage in rat colonic mucosa. British Journal of Nutrition, 89: 581. doi:10.1079/BJN2003849.
   PubMed Web of Science ®Google Scholar
• Lende, A.B.; Kshirsagar, A.D.; Deshpande, A.D.; Muley, M.M.; Patil, R.R. (2011) Anti-inflammatory and analgesic activity of protocatechuic acid in rats and mice. Inflammo Pharmacology, 19: 255. doi:10.1007/s10787-011-0086-4.
   PubMedGoogle Scholar
• Lin, C.Y.; Huang, C.S.; Huang, C.Y.; Yin, M.C. (2009) Anticoagulatory, antiinflammatory, and antioxidative effects of protocatechuic acid in diabetic mice. Journal of Agricultural and Food Chemistry, 57: 6661. doi:10.1021/jf9015202.
   PubMed Web of Science ®Google Scholar
• Yip, E.C.; Chan, A.S.; Pang, H.; Tam, Y.K.; Wong, Y.H. (2006) Protocatechuic acid induces cell death in HepG2 hepatocellular carcinoma cells through a c-Jun N-terminal kinase-dependent mechanism. Cell Biology and Toxicology, 22: 293. doi:10.1007/s10565-006-0082-4.
   PubMed Web of Science ®Google Scholar
• Li, P.; Wang, X.Q.; Wang, H.Z.; Wu, Y.N. (1993) Highperformance liquid chromatographic determination of phenolic acids in fruits and vegetables. Biomedical and Environmental Sciences, 6: 389.
   PubMedGoogle Scholar
• Khan, A.K.; Rashid, R.; Fatima, N.; Mahmood, S.; Mir, S.; Khan, S.; Jabeen, N.; Murtaza, G. (2015) Pharmacological activities of protocatechuic acid. Acta poloniae pharmaceutica, 72: 643.
   PubMed Web of Science ®Google Scholar
• Stich, H.F. (1991) The beneficial and hazardous effects of simple phenolic compounds. Mutation Research, 259: 307. doi:10.1016/0165-1218(91)90125-6.
   PubMed Web of Science ®Google Scholar
• Toma`s-Barberan, F.A.; Clifford, M.N. (2000) Dietary hydroxibenzoic acid derivatives – nature, occurrence and dietary burden. Journal of the Science of Food and Agriculture, 80: 1024. doi:10.1002/(SICI)1097-0010(20000515)80:7<1024::AID-JSFA567>3.0.CO;2-S.
   Web of Science ®Google Scholar
• Kakkar, S.; Bais, S. (2014) A review on protocatechuic acid and its pharmacological potential. ISRN Pharmacology, 2014:9. Article ID 95 2943. doi:10.1155/2014/952943.
   Google Scholar
• Ou, C.; Shi, N.; Yang, Q.; Zhang, Y.; Wu, Z.; Wang, B.; Compans, R.W.; He, C. (2014) Protocatechuic Acid, a Novel Active Substance against Avian Influenza Virus H9N2 Infection. PloS One, 9: 9. doi:10.1371/journal.pone.0111004.
   Web of Science ®Google Scholar
• Ou, C.B.; Pang, Q.; Chen, X.; Hou, N.; He, C. (2012) Protocatechuic acid, a new active substance against the challenge of avian infectious bursal disease virus. Poultry Science, 91: 1604. doi:10.3382/ps.2011-02069.
   PubMed Web of Science ®Google Scholar
• Okai, N.; Miyoshi, T.; Takeshima, Y.; Kuwahara, H.; Ogino, C.; Kondo, A. (2016) Production of protocatechuic acid by Corynebacterium glutamicum expressing chorismate-pyruvate lyase from Escherichia coli. Applied Microbiology and Biotechnology, 100: 135. doi:10.1007/s00253-015-6976-4.
   PubMed Web of Science ®Google Scholar
• Alemika, T.E.; Onawunm, G.O.; Olugbade, T.O. (2016) Antibacterial phenolics from Boswellia dalzielii. Nigerian Journal of Natural Products and Medicine, 10: 108.
   Google Scholar
• Mallavadhani, U.V.; Mahapatra, A. (2005) A new aurone and two rare metabolites from the leaves of Diospyros melanoxylon. Natural Product Research, 19: 91. doi:10.1080/14786410410001704705.
   PubMed Web of Science ®Google Scholar
• Garner, B.L.; Arceneaux, J.E.L.; Byers, B.R. (2004) Temperature control of a 3,4-dihydroxybenzoate (protocatechuate)-based siderophore in Bacillus anthracis. Current Microbiology, 49: 89. doi:10.1007/s00284-004-4305-8.
   PubMed Web of Science ®Google Scholar
• Wilson, M.K.; Abergel, R.J.; Raymond, K.N.; Arceneaux, J.E.; Byers, B.R. (2006) Siderophores of Bacillus anthracis, Bacillus cereus, and Bacillus thuringiensis. Biochemical and Biophysical Research Communications, 348: 320. doi:10.1016/j.bbrc.2006.07.055.
   PubMed Web of Science ®Google Scholar
• Williams, K.M.; Martin, W.E.; Smith, J.; Williams, B.S.; Garner, B.L. (2012) Production of protocatechuic acid in Bacillus thuringiensis ATCC33679. International Journal of Molecular Sciences, 13: 3765. doi:10.3390/ijms13033765.
   PubMed Web of Science ®Google Scholar
• Cascaval, D.; Oniscu, C.; Dumitru, I.F.; Galaction, A.I. (2001) New separation techniques in biotechnology. Romanian Biotechnological Letters, 6: 207.
   Google Scholar
• Kumar, S.; Babu, B.V. (2009) Process intensification of nicotinic acid production via enzymatic conversion using reactive extraction. Chemical And Biochemical Engineering Quarterly, 23: 367.
   Web of Science ®Google Scholar
• Wasewar, K.L.; Yawalkar, A.; Moulijn, J.; Pangarkar, V.G. (2004) Fermentation of glucose to lactic acid coupled with reactive extraction: areview. Industrial & Engineering Chemistry Research, 43: 5969. doi:10.1021/ie049963n.
   Web of Science ®Google Scholar
• Tamada, J.A.; Kertes, A.S.; King, C.J. (1990) Extraction of carboxylic acids with amine extractants, 1: equilibria and law of mass action modeling. Industrial & Engineering Chemistry Research, 29: 1319. doi:10.1021/ie00103a035.
   Web of Science ®Google Scholar
• Kertes, A.S.; King, C. (1986) Extraction chemistry of fermentation product carboxylic acids. Journal of Biotechnology and Bioengineering, 28: 269. doi:10.1002/bit.260280217.
   PubMed Web of Science ®Google Scholar
• Malmary, G.; Albet, J.; Putranto, A.M.H.; Molinier, J. (2001) Recovery of carboxylic acids from aqueous solutions by liquid-liquid Extraction with a triisooctylamine diluent system. Brazilian Journal of Chemical Engineering, 18 (4): 441. doi:10.1590/S0104-66322001000400008.
   Web of Science ®Google Scholar
• Athankar, K.K.; Wasewar, K.L.; Varma, M.N.; Shende, D.Z. (2017) Separation of phenylacetic acid using tri-n-butyl phosphate in hexanol: equilibrium and kinetics. Separation Science and Technology, 52: 2696.
   Web of Science ®Google Scholar
• Athankar, K.K.; Varma, M.N.; Shende, D.Z.; Yoo, C.K.; Wasewar, K.L. (2013) Reactive extraction of phenylacetic acid with Tri-n-butyl phosphate in benzene, hexanol, and rice bran oil at 298 K. Journal of Chemical & Engineering Data, 58: 3240. doi:10.1021/je400696d.
   Web of Science ®Google Scholar
• Athankar, K.K.; Wasewar, K.L.; Varma, M.N.; Shende, D.Z.; Uslu, H. (2015) Extractive separation of benzylformic acid with phosphoric acid tributyl ester in CCl4, Decanol, Kerosene, Toluene, and Xylene at 298 K. Journal of Chemical & Engineering Data, 60: 1014. doi:10.1021/je500943m.
   Web of Science ®Google Scholar
• Athankar, K.K.; Wasewar, K.L.; Varma, M.N.; Shende, D.Z. (2016) Reactive extraction of gallic acid with tri-n-caprylylamine. New Journal of Chemistry, 40: 2413. doi:10.1039/C5NJ03007B.
   Web of Science ®Google Scholar
• Rewatkar, K.; Shende, D.Z.; Wasewar, K.L. (2016) Effect of temperature on reactive extraction of gallic acid using Tri-n-butyl phosphate, Tri-n-octylamine and Aliquat 336. Journal of Chemical & Engineering Data, 61: 3217. doi:10.1021/acs.jced.6b00310.
   Web of Science ®Google Scholar
• Rewatkar, K.; Shende, D.Z.; Wasewar, K.L. (2017) Reactive separation of gallic acid: experimentation and optimization using response surface methodology and artificial neural network. Chemical And Biochemical Engineering Quarterly, 31: 33. doi:10.15255/CABEQ.2016.931.
   Web of Science ®Google Scholar
• Wasewar, K.L.; Shende, D.Z.; Keshav, A. (2011) Reactive extraction of itaconic acid using aliquat 336 in various diluents. Industrial & Engineering Chemistry Research, 50: 1003. doi:10.1021/ie1011883.
   Web of Science ®Google Scholar
• Keshav, A.; Wasewar, K.L. (2009) Reactive extraction of acrylic acid using Tri-n-Butyl phosphate in different solvents. Journal of Chemical & Engineering Data, 54: 1782. doi:10.1021/je800856e.
   Web of Science ®Google Scholar
• Sharma, H.; Singh, K.; Wasewar, K.L.; Athankar, K.K. (2017) L(+)-tartaric acid separations using aliquat 336 in n Heptane, Kerosene, and 1 Octanol at 300 ± 1 K. Journal of Chemical & Engineering Data, 62: 4047. doi:10.1021/acs.jced.6b01070.
   Web of Science ®Google Scholar
• Wasewar, K.L.; Heesink, A.B.M.; Versteeg, G.F.; Pangarkar, V.G. (2004) Equilibria and kinetics for back extraction of lactic acid using trimethylamine. Journal of Chemical & Engineering Data, 59: 2315.
   Google Scholar
• Wasewar, K.L.; Heesink, A.B.M.; Versteeg, G.F.; Pangarkar, V.G. (2002) Reactive extraction of lactic acid using alamine 336 in mibk: equilibria and kinetics. Journal of Biotechnology, 97:59–68.
   Web of Science ®Google Scholar
• Wasewar, K.L.; Heesink, A.B.M.; Versteeg, G.F.; Pangarkar, V.G. (2002) Equilibria and kinetics for reactive extraction of lactic acid using alamine 336 in decanol. Journal of Chemical Technology & Biotechnology, 77: 1068. doi:10.1002/jctb.680.
   Web of Science ®Google Scholar
• Wasewar, K.L.; Heesink, A.B.M.; Versteeg, G.F.; Pangarkar, V.G. (2002) Intensification of enzymatic conversion of glucose to lactic acid by reactive extraction. Chemical Engineering Science, 58 (15): 3385. doi:10.1016/S0009-2509(03)00221-5.
   Web of Science ®Google Scholar
• Uslu, H.; Kirbaslar, S.I.; Wasewar, K.L. (2009) Reactive extraction of levulinic acid by amberlite LA-2 extractant. Journal of Chemical & Engineering Data, 54: 712–718. doi:10.1021/je800261j.
   Web of Science ®Google Scholar
• Keshav, A.; Chand, S.; Wasewar, K.L. (2008) Equilibrium studies for extraction of propionic acid using Tri-n-Butyl phosphate in different solvents. Journal of Chemical & Engineering Data, 53: 1424. doi:10.1021/je7006617.
   Web of Science ®Google Scholar
• Keshav, A.; Wasewar, K.L.; Chand, S. (2009) Reactive extraction of propionic acid using Tri-n-Octylamine. Chemical Engineering Communications, 197: 606. doi:10.1080/00986440903249015.
   Web of Science ®Google Scholar
• Keshav, A.; Wasewar, K.L. (2010) Back extraction of propionic acid from loaded organic phase. Chemical Engineering Science, 65: 2751. doi:10.1016/j.ces.2010.01.010.
   Web of Science ®Google Scholar
• Wasewar, K.L.; Shende, D.Z. (2011) Equilibrium for the reactive extraction of caproic acid using tri-n-butyl phosphate in methylisobutyl ketone and xylene. Journal of Chemical & Engineering Data, 56: 3318. doi:10.1021/je200138w.
   Web of Science ®Google Scholar
• Wasewar, K.L.; Shende, D.Z. (2011) Reactive extraction of caproic acid using tri-n-butyl phosphate in hexanol, octanol, and decanol. Journal of Chemical & Engineering Data, 56: 288. doi:10.1021/je100974f.
   Web of Science ®Google Scholar
• Wasewar, K.L.; Shende, D.Z. (2010) extraction of caproic acid using tri-n-butyl phosphate in benzene and toluene at 301 K. Journal of Chemical & Engineering Data, 55: 4121. doi:10.1021/je100337m.
   Web of Science ®Google Scholar
• Antony, F.M.; Wasewar, K.L. (2018) Reactive separation of protocatechuic acid using Tri-n-octyl amine and Di-(2-ethylhexyl) phosphoric acid in methyl isobutyl ketone. Separation and Purification Technology. doi:10.1016/j.seppur.2018.06.037.
   Web of Science ®Google Scholar
• Reichardt, C.;. (1979) Empirical parameters of solvent polarity as linear free-energy relationships. Angewandte Chemie International Edition in English, 18: 98. doi:10.1002/anie.197900981.
   Web of Science ®Google Scholar
• Kojima, T.; Fukutomi, H. (1987) Extraction equilibria of hydrochloric acid by trioctylamine in low-polar organic solvents. Bulletin of the Chemical Society of Japan, 60: 1309. doi:10.1246/bcsj.60.1309.
   Web of Science ®Google Scholar
• Datta, D.; Kumar, S.; Wasewar, K.L.; Babu, B.V. (2012) Comparative study on reactive extraction of picolinic acid with six different extractants (phosphoric and aminic) in two different diluents (benzene and decan-1-ol). Separation Science and Technology, 47: 997. doi:10.1080/01496395.2011.638961.
   Web of Science ®Google Scholar
• Keshav, A.; Wasewar, K.L.; Chand, S. (2010) Reactive extraction of propionic acid using Tri-n-octylamine. Chemical Engineering Communications, 197: 606. doi:10.1080/00986440903249015.
   Web of Science ®Google Scholar
• Keshav, A.; Wasewar, K.L.; Chand, S. (2008) Extraction of propionic acid using different extractants (Tri-n-butylphosphate, Tri-n-octylamine, and Aliquat 336). Industrial & Engineering Chemistry Research, 47: 6192. doi:10.1021/ie800006r.
   Web of Science ®Google Scholar
• Datta, D.; Kumar, S.; Uslu, H. (2015) Status of the reactive extraction as a method of separation. J. Chem, 2015. Article ID 853789 16 pages. http://dx.doi.org/10.1155/2015/853789.
   Google Scholar
• Keshav, A.; Wasewar, K.L.; Chand, S. (2008) Equilibrium studies for extraction of propionic acid using Tri-n-butyl phosphate in different solvents. Journal of Chemical & Engineering Data, 53: 1424. doi:10.1021/je7006617.
   Web of Science ®Google Scholar
• Kumar, S.; Babu, B.V. (2009) Process intensification of nicotinic acid production via enzymatic conversion using reactive extraction. Chemical And Biochemical Engineering Quarterly, 23: 36.
   Web of Science ®Google Scholar
• Niitsu, M.; Sekine, T. (1978) Solvent extraction of ionic solutes in aqueous solutions. Bulletin of the Chemical Society of Japan, 51: 705. doi:10.1246/bcsj.51.705.
   Web of Science ®Google Scholar
• Hong, Y.K.; Hong, W.H.; Han, D.H. (2001) Application of reactive extraction to recovery of carboxylic acids. Biotechnology And Bioprocess Engineering, 6: 386. doi:10.1007/BF02932319.
   Google Scholar
• Bart, H.-J.; (2013) Reactive Extraction Springer Science & Business Media
   Google Scholar
• Wilke, C.R.; Chang, P. (1955) Correlation of diffusion coefficients in dilute solutions. American Institute of Chemical Engineers, 1: 264–270. doi:10.1002/(ISSN)1547-5905.
   Web of Science ®Google Scholar
• Reddy, K.A.; Doraiswamy, L.K. (1967) Estimating liquid diffusivity. Industrial & Engineering Chemistry Fundamentals, 6: 77–79. doi:10.1021/i160021a012.
   Web of Science ®Google Scholar
• Shan, X.C.;, 2003. Study on extraction equilibria behavior of carboxylic acids with relative basicity. Bachelor Thesis, Tsinghua University
   Google Scholar
• Haan, A.B.; deBosch, H. (2013) Industrial Separation Processes, DeGruyter: Berlin.
   Google Scholar
• Krzyzaniak, A.; Schuur, B.; Haan, A.B. (2014) Equilibrium studies on lactic acid extraction with N,N-didodecylpyridin-4-amine (DDAP) extractant. Chemical Engineering Science, 109: 236. doi:10.1016/j.ces.2014.01.030.
   Web of Science ®Google Scholar
• Antony, F.M.; Wasewar, K.L. (2018) Separation of protocatechuic acid using di-(2-ethylhexyl)phosphoric acid in isobutyl acetate, toluene, and petroleum ether. Journal of Chemical & Engineering Data, 207: 99 doi:10.1021/acs.jced.7b00797.
   Web of Science ®Google Scholar