Aceite de trementina comercial enriquecido con α-terpineol usando un catalizador ácido heterogéneo
DOI:
https://doi.org/10.17533/udea.redin.20240101Palabras clave:
Hidratación, Trementina, α-terpineol, α-pineno, Amberlyst-15Resumen
Se estudió la hidratación de α-pineno, limoneno, β-pineno y aceite de trementina comercial en presencia de la resina de intercambio catiónico fuertemente ácida Amberlyst-15. La hidratación catalítica ácida se realizó en un reactor por lotes, evaluándose el efecto del solvente a varias temperaturas y tiempos de reacción. El principal producto de hidratación del α-pineno fue α-terpineol con un rendimiento de 36 % (4 h, 70°C, 2-propanol como solvente); sin embargo, el sistema catalítico seleccionado fue aún más activo a α-terpineol cuando se usó β-pineno como substrato, obteniendo rendimiento a α-terpineol de 38 % en 2 h de reacción. Para la hidratación de trementina (70 °C, relaciones másicas de trementina:agua:2-propanol de 1:0.5:2, 15 %p/p catalizador) la composición de la mezcla de reacción después de 4 h fue 35 %p/p α-terpineol, 8 %p/p α-pineno y 0.5 %p/p de β –pineno; que corresponde al contenido final de α-terpineol cuando α-pineno se empleó como sustrato (36 %p/p).
Descargas
Citas
S. Saeidnia, “Turpentine,” in Encyclopedia of Toxicology, P. Wexler, Ed. Elsevier Inc., 2014, pp. 860–865.
D. F. Zinkel and J. Russell, Naval stores : production, chemistry, utilization. New York, NY: Pulp Chemicals Association, 1989.
H. Pakdel, S. Sarron, and C. Roy, “α-terpineol from hydration of crude sulfate turpentine oil,” Journal of Agricultural and Food Chemistry, vol. 49, no. 9, 2001. [Online]. Available: https://doi.org/10.1021/jf010341b
J. L. F. Monteiro and C. O. Veloso, “Catalytic conversion of terpenes into fine chemicals,” Topics in Catalysis, vol. 27, Feb. 2004. [Online]. Available: https://doi.org/10.1023/B:TOCA.0000013551.99872.8d
N. Comelli, M. Ávila, C. Volzone, and M. Ponzi, “Hydration of α-pinene catalyzed by acid clays,” Open Chemistry, vol. 11, no. 5, Feb. 27, 2013. [Online]. Available: https://doi.org/10.2478/s11532-013-0217-4
P. A. Robles-Dutenhefner, K. A. da Silva, M. R. H. Siddiqui, I. V. Kozhevnikov, and E. V. Gusevskaya, “Hydration and acetoxylation of monoterpenes catalyzed by heteropoly acid,” Journal of Molecular Catalysis A: Chemical, vol. 175, no. 1-2, Sep. 30, 2001. [Online]. Available: https://doi.org/10.1016/S1381-1169(01)00217-5
M. K. Yadav, M. V. Patil, and R. V. Jasra, “Acetoxylation and hydration of limonene and α-pinene using cation-exchanged zeolite beta,” Journal of Molecular Catalysis A: Chemical, vol. 297, no. 2, Sep. 23, 2008. [Online]. Available: https://doi.org/10.1016/j.molcata.2008.09.017
C. M. Williams and D. Whittaker, “Rearrangements of pinane derivatives. part i. products of acid catalysed hydration of α-pinene and β pinene,” Journal of the chemical society B: Physical organic, 1971. [Online]. Available: https://doi.org/10.1039/J29710000668
N. Wijayati1, H. D. Pranowo, J. Jumina, and T. Triyono, “Turpentine oil hydration using trichloroacetic acid as catalyst,” American Journal of Oil and Chemical Technologies, vol. 1, no. 9, Nov. 2013. [Online]. Available: https://doi.org/10.14266/ajoct19-3
K. A. D. Swift, “Catalytic transformations of the major terpene feedstocks,” Topics in Catalysis, vol. 27, 2004. [Online]. Available: https://doi.org/10.1023/B:TOCA.0000013549.60930.da
W. A. Mosher, “The acid catalyzed isomerization of α-pinene,” Journal of the American Chemical Society, vol. 69, no. 9, Sep. 01, 1947. [Online]. Available: https://doi.org/10.1021/ja01201a026
M. Román-Aguirre, L. D. la Torre-Sáenz, W. Antúnez-Flores, A. Robau-Sánchez, and A. Aguilar-Elguézabal, “Synthesis of terpineol from α-pinene by homogeneous acid catalysis,” Journal of the American Chemical Society, vol. 107-108, Aug. 25, 2005. [Online]. Available: https://doi.org/10.1016/j.cattod.2005.07.061
Z. Meng, R. Qin, R. Wen, G. Li, Z. Liang, J. Xie, Z. Yang, and et al., “Study on the hydration of α-pinene catalyzed by α-hydroxycarboxylic acid–boric acid composite catalysts,” Molecules, vol. 28, no. 7, Apr. 04, 2023. [Online]. Available: https://doi.org/10.3390/molecules28073202
T. Prakoso, I. A. Putra, L. Handojo, T. H. Soerawidjaja, H. P. Winoto, and A. Indarto, “A method to control terpineol production from turpentine by acid catalysts mixing,” Heliyon, vol. 6, no. 10, Oct. 08, 2020. [Online]. Available: https://doi.org/10.1016/j.heliyon.2020.e04984
T. Prakoso, J. Hanley, M. N. Soebianta, T. H. Soerawidjaja, and A. Indarto, “Synthesis of terpineol from α-pinene using low-price acid catalyst,” Catalysis Letters, vol. 148, Dec. 08, 2017. [Online]. Available: https://doi.org/10.1007/s10562-017-2267-2
A. Aguilar-Elguezabal, L. de la Torre-Sáenz, M. Román-Aguirre, and L. Álvarez Contreras, “Ionic liquid as green solvent for the synthesis of α-terpineol from α-pinene,” Sustainable Chemistry and Pharmacy, vol. 115, Dec. 17, 2019. [Online]. Available: https://doi.org/10.1016/j.scp.2019.100207
J. C. V. der Wall, H. V. Bekkum, and J. M. Vital, “The hydration and isomerization of α-pinene over zeolite beta. a new coupling reaction between α-pinene and ketones,” Journal of Molecular Catalysis A: Chemical, vol. 105, no. 3, Oct. 07, 1998. [Online]. Available: https://doi.org/10.1016/1381-1169(95)00244-8
J. Vital, A. M. Ramos, I. F. Silva, H. Valente, and J. E. Castanheiro, “Hydration of α-pinene over zeolites and activated carbons dispersed in polymeric membranes,” Catalysis Today, vol. 56, no. 1-3, Feb. 25, 2000. [Online]. Available: https://doi.org/10.1016/S0920-5861(99)00273-4
J. Vital, A. M. Ramos, I. F. Silva, and J. E. Castanheiro, “The effect of α-terpineol on the hydration of α-pinene over zeolites dispersed in polymeric membranes,” Catalysis Today, vol. 67, no. 1-3, May. 15, 2001. [Online]. Available: https://doi.org/10.1016/S0920-5861(01)00289-9
T. Mochida, R. Ohnishi, N. Horita, Y. Kamiya, and T. Okuhara, “Hydration of α-pinene over hydrophobic zeolites in 1,4-dioxane-water and in water,” Microporous and Mesoporous Materials, vol. 101, no. 1-2, Apr. 19, 2007. [Online]. Available: https://doi.org/10.1016/j.micromeso.2006.10.022
M. C. Ávila, N. A. Comelli, E. Rodríguez-Castellón, A. J. Jiménez-López, R. Carrizo-Flores, E. N. Ponzi, and M. I. Ponzi, “Study of solid acid catalysis for the hydration of α-pinene,” Journal of Molecular Catalysis A: Chemical, vol. 322, no. 1-2, May. 01, 2010. [Online]. Available: https://doi.org/10.1016/j.molcata.2010.02.028
J. Xie, Q. Han, J. Wang, L. Bai, J. Lu, and Z. Liu, “Enhanced α-terpineol yield from α-pinene hydration via synergistic catalysis using carbonaceous solid acid catalysts,” Industrial & Engineering Chemistry Research, vol. 58, no. 49, 2019. [Online]. Available: https://doi.org/10.1021/acs.iecr.9b04848
A. Chibiryaev, A. Yermakova, and I. V. Kozhevnikov, “Chemical and phase equilibria calculation of α-pinene hydration in co2-expanded liquid,” The Journal of Supercritical Fluids, vol. 51, no. 3, Nov. 12, 2009. [Online]. Available: https://doi.org/10.1016/j.supflu.2009.11.001
R. W. Charlton and A. R. Day, “Isomerization and hydration of pinene,” Industrial & Engineering Chemistry, vol. 29, no. 1, Jan. 01, 1937. [Online]. Available: https://doi.org/10.1021/ie50325a019
G. Yang, Y. Liu, Z. Zhou, and Z. Zhang, “Kinetic study of the direct hydration of turpentine,” Chemical Engineering Journal, vol. 168, no. 1, Mar. 15, 2011. [Online]. Available: https://doi.org/10.1016/j.cej.2011.01.037
S. Talwalkar and P. Kumbhar and S. Mahajani, “Hydration of dicyclopentadiene in the presence of cation exchange resin,” Industrial & Engineering Chemistry Research, vol. 45, no. 24, Nov. 01, 2006. [Online]. Available: https://doi.org/10.1021/ie060470n
S. Talwalkar, P. Kumbhar, and S. Mahajani, “In situ coating on cation exchange resin catalyst, amberlyst-15, and its impact on the hydration of dicyclopentadiene,” Catalysis Communications, vol. 7, no. 9, Feb. 28, 2006. [Online]. Available: https://doi.org/10.1016/j.catcom.2006.02.018
S. H. Ali, “In situ coating on cation exchange resin catalyst, amberlyst-15, and its impact on the hydration of dicyclopentadiene,” Kinetics of catalytic esterification of propionic acid with different alcohols over Amberlyst 15, vol. 41, no. 6, Mar. 25, 2009. [Online]. Available: https://doi.org/10.1002/kin.20416
P. Delgado, M. T. Sanz, and S. Beltrán, “Kinetic study for esterification of lactic acid with ethanol and hydrolysis of ethyl lactate using an ion-exchange resin catalyst,” Chemical Engineering Journal, vol. 126, no. 2-3, Feb. 15, 2007. [Online]. Available: https://doi.org/10.1016/j.cej.2006.09.004
N. Wijayati, H. D. Pranowo, J. Jumina, and T. Triyono, “Synthesis of terpineol from α-pinene catalyzed by tca/y-zeolite,” Indonesian Journal of Chemistry, vol. 11, no. 3, 2011. [Online]. Available: https://doi.org/10.22146/ijc.21386
C. Reichardt and T. Welton, Solvents and Solvent Efects in Organic Chemistry, 4th ed. Weinheim, GE: Wiley-VCH, 2011.
W. Xiao-Feng, Solvents as Reagents in Organic Synthesis: Reactions and Applications. Wiley-VCH, 2017.
I. F. McConvey, D. Woods, M. Lewis, Q. Gan, and P. Nancarrow, “The importance of acetonitrile in the pharmaceutical industry and opportunities for its recovery from waste,” Organic Process Research & Development, vol. 16, no. 4, Feb. 27, 2012. [Online]. Available: https://doi.org/10.1021/op2003503
(2023, Apr. 17,) Global acetonitrile market is poised to generate a revenue of US$ 595.96 million by 2031. Astute Analytica. [Online]. Available: http://tinyurl.com/32e7598f
N. Wijayati, H. D. Pranowo, J. Jumina, and T. Triyono, “The acid catalyzed reaction of α-pinene over y-zeolite,” Indonesian Journal of Chemistry, vol. 13, no. 1, 2013. [Online]. Available: https://doi.org/10.22146/ijc.21327
Descargas
Publicado
Cómo citar
Número
Sección
Licencia
Derechos de autor 2024 Revista Facultad de Ingeniería Universidad de Antioquia
Esta obra está bajo una licencia internacional Creative Commons Atribución-NoComercial-CompartirIgual 4.0.
Los artículos disponibles en la Revista Facultad de Ingeniería, Universidad de Antioquia están bajo la licencia Creative Commons Attribution BY-NC-SA 4.0.
Eres libre de:
Compartir — copiar y redistribuir el material en cualquier medio o formato
Adaptar : remezclar, transformar y construir sobre el material.
Bajo los siguientes términos:
Reconocimiento : debe otorgar el crédito correspondiente , proporcionar un enlace a la licencia e indicar si se realizaron cambios . Puede hacerlo de cualquier manera razonable, pero no de ninguna manera que sugiera que el licenciante lo respalda a usted o su uso.
No comercial : no puede utilizar el material con fines comerciales .
Compartir igual : si remezcla, transforma o construye a partir del material, debe distribuir sus contribuciones bajo la misma licencia que el original.
El material publicado por la revista puede ser distribuido, copiado y exhibido por terceros si se dan los respectivos créditos a la revista, sin ningún costo. No se puede obtener ningún beneficio comercial y las obras derivadas tienen que estar bajo los mismos términos de licencia que el trabajo original.
Twitter