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Fine Chemistry

In this research line, the development of innovative catalytic processes for the synthesis of valuable fine chemicals is studied. By using novel solid catalysts (or by optimizing current catalytic materials) and/or by changing the operation conditions and process characteristics, we explore the feasibility of developing new catalytic technologies to obtain fine chemicals. The following processes are studied: a) Synthesis of fine chemicals using guaiacol feedstock; b) One-step synthesis of beta y alfa-ionones from aldol condensation of citral with acetone; c) Synthesis of valuable chemicals by the gas-phase alkylation of phenol and cresols. The products obtained from these reactions are widely employed in food, pharmaceutical and perfumery industries.

Reactions
  • Synthesis of fine chemicals from guaiacol
    We investigate the synthesis of fine chemicals from the alkylation/acylation of biomass-derived guaiacol on solids acids. The acylation of guaiacol with acetic acid may be used to produce pain/anti-inflammatory drugs such as the acetovanillone or apocynin. On the other hand, the alkylation of guaiacol with cyclohexanol or cyclohexene forms valuable intermediates for the production of agrochemicals, dyes, resins and polymer additives.
 
  • Synthesis of ionones
    The b-ionone isomer is used for the synthesis of vitamin A, whereas a- and g-ionones are very appreciated in the fragrance industry.  Ionones are commercially produced via the liquid-phase cyclization of pseudoionone using mineral acids. We study the cyclization of pseudoionone to ionones on solid acids containing essentially strong Brønsted acid sites. The goal is to select the best catalyst and reaction conditions to improve the catalyst activity and selectively for obtaining ionone yields comparable to those of the homogeneous process using liquid acids.                                              

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  • Synthesis of valuable chemicals by alkylation of phenol and cresols
    p-Cresol is employed to produce pharmaceuticals, herbicides, agrochemicals and dyes, but its current commercial synthesis via toluene dehydration using sulphuric acid entails serious environmental concerns. We investigate the gas-phase methylation of phenol on acid zeolites with the goal of significantly improving the selective synthesis of p-cresol. On the other hand, the alkylation of m-cresol with methanol forms valuable chemicals such as 2,5-xylenol that is employed for the manufacture of pharmaceuticals and is also an intermediate in the synthesis of colorants, antiseptics and antioxidants. The goal of our research is to ascertain the effect that the pore microstructure and the nature, density, and strength of surface acid sites have on the catalyst performance. 
 

Recent Publications

  • Insights into the Kinetics of the Guaiacol Alkylation with Cyclohexanol in a One-Pot Process, Montañez Valencia, M.K., Bertero, N.M., Padró, C.L., Sad, M.E, Ind. and Eng. Chem. Research, 63, 15790–15799 (2024).
  • Synthesis of indene in the liquid phase by a one-pot process using orthogonal tandem catalysis, N.M. Bertero, A.F. Trasarti, A.J. Marchi, C.R. Apesteguía, React. Chem. Eng., 8, 2703-2709 (2023).
  • Selective synthesis of 1-indanol by 1-indanone liquid-phase hydrogenation over metal-based catalysts: A LHHW kinetic approach, N.M. Bertero, A.F. Trasarti, A.J. Marchi, C.R. Apesteguía, Chem. Eng. Sci.; 254, 117629 - 117642 (2022).
  • Kinetic modeling of liquid phase catalytic alkylation of guaiacol with cyclohexene, Montañez Valencia, M.K., Bertero, N.M., Padró, C.L., Sad, M.E., Chem. Eng. J. Adv.; 7, 100112 - 100118 (2021).
  • Effect of solvent on heterogeneously catalyzed reactions: The case of hydrogenation of carbonyl compounds for production of fine chemicals, N.M. Bertero, A.F. Trasarti, C.R. Apesteguía, A.J. Marchi, in Solvent Effects in Chemistry: Advances in Applications and Research, Editor Valerie Mireault, Nova Science Publishers, Inc., ISBN: 9781536182262, Chapter 1, pp. 1-100, 2020.
  • Solvent effects in solid acid-catalyzed reactions: The case of the liquid-phase isomerización/cyclization of citronellal over SiO2-Al2O3, N.M. Bertero, A.F. Trasarti, A.J. Marchi, C.R. Apesteguía, Molec. Catal., 481, 110192, 1-9 (2020).
  • Gas phase acylation of guaiacol with acetic acid on acid catalysts, Montañez Valencia, M.K., Padró, C.L., Sad, M.E., Appl. Catal. B: Environmental, 278,119317 (2020).
  • Selective one-pot synthesis of asymmetric secondary amines via N-alkylation of nitriles with alcohols, D.J. Segobia, A.F. Trasarti, C.R. Apesteguia, J. Catal., 380, 178-185 (2019)..
  • Kinetic and mechanistic study of the synthesis of ionone isomers from pseudoionone on Brønsted acid solids, V.K. Díez, C.R. Apesteguía, J.I. Di Cosimo, Catal. Today, 296, 127-134 (2017).
  • m-Cresol methylation: Role of internal and external acid sites in the product distribution, M.D. Acevedo, M.K. Montañez-Valencia, N.B. Okulik, M.E. Sad, C.L. Padró, Catal. Commun. 92, 10-14 (2017).
  • Selective synthesis of p-ethylphenol by gas-phase alkylation of phenol with ethanol, M.E. Sad, C.L. Padró, C.R. Apesteguía, Appl. Catal. A: General, 486, 77-84 (2014).
  • Study of gas phase m-cresol alkylation with methanol on solid acid catalysts, M.D. Acevedo, G.A. Bedogni, N.B. Okulik, C.L. Padró, Catal. Lett., 144, 1946-1954 (2014).
  • Phenol methylation on acid catalysts: Study of the catalyst deactivation kinetics and mechanism, M.E. Sad, H. Duarte, C.L. Padró, C.R. Apesteguía, Appl. Catal. A: General, 475, 305-313 (2014).

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