Process for the Obtention of Coumaric Acid from Coumarin: Analysis of the Reaction Conditions
Affiliation(s)
. Chemical Engineering Department of the Faculty of Chemistry, Universidad Nacional Autónoma de México (UNAM) Coyoacan, D. F. México, México.
. Chemical Engineering Department of the Faculty of Chemistry, Universidad Nacional Autónoma de México (UNAM) Coyoacan, D. F. México, México.
ABSTRACT
Coumaric acid can be obtained from basic hydrolysis of coumarin, through a reaction process consisting on opening the lactone ring and cis-trans isomerization. Parameters such as reaction time, temperature, NaOH concentration, solvent and reaction atmosphere, have been thoroughly studied and analyzed, in order to determine the appropriate conditions for the maximum conversion efficiency of coumarin into coumaric acid. Experimental results show that the best conditions are a 1 hour reaction time, at 160℃, with a 20% sodium hydroxide aqueous solution, and in an inert reaction atmosphere.
Cite this paper
N. López-Castillo, A. Rojas-Rodríguez, B. Porta and M. Cruz-Gómez, "Process for the Obtention of Coumaric Acid from Coumarin: Analysis of the Reaction Conditions," Advances in Chemical Engineering and Science, Vol. 3 No. 3, 2013, pp. 195-201. doi: 10.4236/aces.2013.33025.
N. López-Castillo, A. Rojas-Rodríguez, B. Porta and M. Cruz-Gómez, "Process for the Obtention of Coumaric Acid from Coumarin: Analysis of the Reaction Conditions," Advances in Chemical Engineering and Science, Vol. 3 No. 3, 2013, pp. 195-201. doi: 10.4236/aces.2013.33025.
References
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[1] R. E. Kirk and D. F. Othmer, “Encyclopedia of Chemical Technology,” 5th Edition; John Wiley & Sons Ltd., Chichester, 2007. [2] J. R. S. Hoult and M. Paydt, “Pharmacological and Biochemical Actions of Simple Coumarins: Natural Products with Therapeutic Potential,” General Pharmacology, Vol. 27, No. 4, 1996, pp. 713-722. doi:10.1016/0306-3623(95)02112-4 [3] E. M. Agostinha, R. Matos, C. C. S. Sousa, et al., “Energetics of Coumarin and Chromone” The Journal of Physical Chemistry B, Vol. 113, No. 32, 2009, pp. 11216-11221. doi:10.1021/jp9026942 [4] J. Preat, D. Jacquemin, et al., “Theoretical Investigation of Substituted Anthraquinone Dyes,” Journal of Chemical Physics, Vol. 415, No. 20, 2005, pp. 1736-1743. doi:10.1063/1.1764497 [5] B. A. Chauder, C. C. Lopes, R. S. C. Lopes, A. J. M. da Silva and V. Snieckus, “Phenylboronic Acid-Mediated Synthesis of 2H-Chromenes,” Synthesis, Vol. 1998, No. 3, 1998, pp. 279-282. doi:10.1055/s-1998-2042 [6] K. A. Parker and T. L. Mindt, “Electrocyclic Ring Closure of the Enols of Vinyl Quinones. A 2H-Chromene Synthesis,” Organic Letters, Vol. 3 No. 24, 2001, pp. 3875-3878. doi:10.1021/ol0167199 [7] I. H. Updergraff and H. G. Cassidy, “Electron Exchange—Polymer II. Vinylhydroquinone Monomer and Polymer,” Journal of the American Chemical Society, Vol. 71, No. 407, 1949, pp. 407-410. doi:10.1021/ja01170a010 [8] S. Patai, “The Chemistry of Functional Groups. The Chemistry of Quinoid Compounds. Part 2,” 1st Edition, John Wiley & Sons Ltd., Chichester, 1974. [9] D. Burton and D. Ollis “Comprehensive Organic Chemistry. (The Synthesis and Reactions of Organic Compounds),” 1st Edition, Pergamon Press, Oxford, 1979. [10] R Murray, J Mendez and S. Brown, “The Natural Coumarins,” John Wiley & Sons, Chichester, 1997. [11] E. Cingolani, “Idrolisi del Ciclo Cumarinico e Transformazione cis—Trans Degli Acidi O-Ossicinnamici,” Gazzeta, Vol. 89, No. 5, 1959, pp. 195-1998. [12] E. Cingolani, “Trasformazione Degli Acidi Cumárico (Trans O-Ossicinnamici) Nelle Cumarina Corrispondenti,” Gazzetta, Vol. 46, No. 9, 1959, pp. 999-1008. [13] D. Bihari and K. Krishna, “Action of Sodium Sulphite on Coumarins,” Journal of the American Chemical Society, Vol. 46, No. 3, 1924, pp. 554-564. [14] R. Adams and T. E. Bockstahler, “Preparation and Reactions of O-Hydroxycinnamic Acids and Esters,” Journal of the American Chemical Society, Vol. 74, No. 21, 1952, pp. 5346-5348. doi:10.1021/ja01141a038 [15] F. D. Dodge, “Some Derivatives of Coumarin,” Journal of the American Chemical Society, Vol. 38, No. 2, 1916, pp. 446-457. doi:10.1021/ja02259a030