Synthesis of dihydrocarvone over dendritic ZSM-5 Zeolite: A comprehensive study of experimental, kinetics, and computational insights
[Display omitted] •Kinetics and mechanism of limonene-1,2-epoxide isomerization.•Dendritic ZSM-5 zeolite is highly selective for formation of dihydrocarvone.•Kinetic modeling based on the reaction network with eight parallel reactions.•Adequate description of kinetics with statistically reliable par...
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Published in | Chemical engineering journal (Lausanne, Switzerland : 1996) Vol. 498; p. 155377 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
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Elsevier B.V
15.10.2024
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Abstract | [Display omitted]
•Kinetics and mechanism of limonene-1,2-epoxide isomerization.•Dendritic ZSM-5 zeolite is highly selective for formation of dihydrocarvone.•Kinetic modeling based on the reaction network with eight parallel reactions.•Adequate description of kinetics with statistically reliable parameters.•Density Functional Theory calculations revealed the preferred pathways for limonene-1,2-epoxide isomerization.
This study explores the isomerization of limonene-1,2-epoxide (LE) from kinetic and mechanistic viewpoints, using a dendritic ZSM-5 zeolite (d-ZSM-5) as a highly selective catalyst for the formation of dihydrocarvone (DHC) in the form of diastereoisomers (cis + trans). Ethyl acetate, a green solvent, was used at mild reaction temperatures (50–––70 °C). DHC, which can also be extracted from caraway oil, is widely used as an intermediate for epoxylactone production and as a constituent in flavors and perfumes. Kinetic modeling of LE isomerization was performed using a reaction network with eight parallel reactions and the corresponding rate equations, derived from the assumption of the rate-limiting surface reactions. The large standard errors in the statistical results of some kinetic parameters of the initial data fitting suggested that three of those reactions can be neglected to describe the kinetic model more accurately. This refinement resulted in standard errors in the kinetic parameters lower than ca. 11 %, confirming the statistical reliability of the modified kinetic model. Activation energies of 41.1 and 162 kJ/mol were estimated for the formation of cis-DHC and trans-DHC, respectively. Density Functional Theory (DFT) calculations revealed the preferred pathway for both cis and trans-LE conversion to DHC and carveol. The rate-determining step, carbocation formation (ΔEact = 234 kJ/mol), precedes near-instantaneous dihydrocarvone formation under the studied conditions. |
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AbstractList | [Display omitted]
•Kinetics and mechanism of limonene-1,2-epoxide isomerization.•Dendritic ZSM-5 zeolite is highly selective for formation of dihydrocarvone.•Kinetic modeling based on the reaction network with eight parallel reactions.•Adequate description of kinetics with statistically reliable parameters.•Density Functional Theory calculations revealed the preferred pathways for limonene-1,2-epoxide isomerization.
This study explores the isomerization of limonene-1,2-epoxide (LE) from kinetic and mechanistic viewpoints, using a dendritic ZSM-5 zeolite (d-ZSM-5) as a highly selective catalyst for the formation of dihydrocarvone (DHC) in the form of diastereoisomers (cis + trans). Ethyl acetate, a green solvent, was used at mild reaction temperatures (50–––70 °C). DHC, which can also be extracted from caraway oil, is widely used as an intermediate for epoxylactone production and as a constituent in flavors and perfumes. Kinetic modeling of LE isomerization was performed using a reaction network with eight parallel reactions and the corresponding rate equations, derived from the assumption of the rate-limiting surface reactions. The large standard errors in the statistical results of some kinetic parameters of the initial data fitting suggested that three of those reactions can be neglected to describe the kinetic model more accurately. This refinement resulted in standard errors in the kinetic parameters lower than ca. 11 %, confirming the statistical reliability of the modified kinetic model. Activation energies of 41.1 and 162 kJ/mol were estimated for the formation of cis-DHC and trans-DHC, respectively. Density Functional Theory (DFT) calculations revealed the preferred pathway for both cis and trans-LE conversion to DHC and carveol. The rate-determining step, carbocation formation (ΔEact = 234 kJ/mol), precedes near-instantaneous dihydrocarvone formation under the studied conditions. |
ArticleNumber | 155377 |
Author | Gallego-Villada, Luis A. Sánchez-Velandia, Julián E. Cueto, Jennifer Perez-Sena, Wander Y. Mäki-Arvela, Päivi Wärmå, Johan del Mar Alonso-Doncel, María Serrano, David P. Alarcón, Edwin A. Murzin, Dmitry Yu |
Author_xml | – sequence: 1 givenname: Luis A. surname: Gallego-Villada fullname: Gallego-Villada, Luis A. email: alfonso.gallego@udea.edu.co organization: Laboratory of Industrial Chemistry and Reaction Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, Henriksgatan 2, 20500 Turku/Åbo, Finland – sequence: 2 givenname: Wander Y. surname: Perez-Sena fullname: Perez-Sena, Wander Y. organization: Laboratory of Industrial Chemistry and Reaction Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, Henriksgatan 2, 20500 Turku/Åbo, Finland – sequence: 3 givenname: Julián E. surname: Sánchez-Velandia fullname: Sánchez-Velandia, Julián E. organization: Sustainable and Supramolecular Research Group, Universidad Jaume I, Av. Vicent Sos Baynot, s/n, 12006, Castelló de la Plana, Spain – sequence: 4 givenname: Jennifer surname: Cueto fullname: Cueto, Jennifer organization: Thermochemical Processes Unit, IMDEA Energy Institute, Avda. Ramón de la Sagra, 3, 28935, Móstoles, Madrid, Spain – sequence: 5 givenname: María surname: del Mar Alonso-Doncel fullname: del Mar Alonso-Doncel, María organization: Thermochemical Processes Unit, IMDEA Energy Institute, Avda. Ramón de la Sagra, 3, 28935, Móstoles, Madrid, Spain – sequence: 6 givenname: Johan surname: Wärmå fullname: Wärmå, Johan organization: Laboratory of Industrial Chemistry and Reaction Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, Henriksgatan 2, 20500 Turku/Åbo, Finland – sequence: 7 givenname: Päivi surname: Mäki-Arvela fullname: Mäki-Arvela, Päivi organization: Laboratory of Industrial Chemistry and Reaction Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, Henriksgatan 2, 20500 Turku/Åbo, Finland – sequence: 8 givenname: Edwin A. surname: Alarcón fullname: Alarcón, Edwin A. organization: Environmental Catalysis Research Group, Chemical Engineering Faculty, Universidad de Antioquia, Medellín, Colombia – sequence: 9 givenname: David P. surname: Serrano fullname: Serrano, David P. email: david.serrano@imdea.org organization: Thermochemical Processes Unit, IMDEA Energy Institute, Avda. Ramón de la Sagra, 3, 28935, Móstoles, Madrid, Spain – sequence: 10 givenname: Dmitry Yu surname: Murzin fullname: Murzin, Dmitry Yu email: dmitry.murzin@abo.fi organization: Laboratory of Industrial Chemistry and Reaction Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, Henriksgatan 2, 20500 Turku/Åbo, Finland |
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Cites_doi | 10.1016/j.cattod.2019.11.031 10.4067/S0717-97072005000300006 10.1016/j.indcrop.2012.05.026 10.1007/s11144-021-01974-1 10.1016/j.molcata.2016.04.013 10.1016/j.apcata.2019.117173 10.4236/ijoc.2013.33027 10.1021/ed064p561 10.1002/anie.200805838 10.1016/j.bmcl.2010.09.113 10.1016/j.cattod.2021.09.011 10.1016/j.crci.2004.12.015 10.1002/jcc.23037 10.1021/acs.jpca.7b09427 10.1007/s11244-013-0029-y 10.1063/1.3382344 10.1021/acs.iecr.3c02633 10.1021/acs.iecr.3c00893 10.1023/B:TOCA.0000013550.28170.6a 10.1016/j.micromeso.2024.113098 10.1016/0021-9517(76)90213-X 10.1021/acsomega.1c03779 10.1021/bm900471a 10.1039/D4GC04003A 10.1039/B715018K 10.1021/acs.cgd.3c00326 10.1016/j.jcat.2021.12.008 10.1021/acs.jctc.9b00823 10.1021/ct049977a 10.1063/1.478304 10.1016/j.jechem.2023.01.023 10.1016/j.cattod.2007.12.107 10.1021/cr050989d 10.1039/C2CY20526B 10.1021/ja00905a001 10.1080/01614940.2024.2329553 10.1016/j.comptc.2013.04.009 10.1016/j.cattod.2013.12.004 10.1016/j.fct.2008.06.032 10.1016/j.ica.2021.120263 |
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Keywords | Dihydrocarvone Dendritic zeolite Limonene epoxide Kinetic modeling Density Functional Theory (DFT) ZSM-5 |
Language | English |
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References | Corma, Iborra, Velty (b0095) 2007; 107 Raptis, Garcia, Stratakis (b0115) 2009; 48 Gallego-Villada, Alarcón, Villa (b0035) 2023; 62 Civalleri, Zicovich-Wilson, Valenzano, Ugliengo (b0170) 2008; 10 Nguyen, Chau, Duus, Le (b0090) 2013; 03 Foreverest, Dihydrocarvone, (n.d.). Thompson (b0210) 1999; 110 Dong, McCullough, Wittlin, Chollet, Vennerstrom (b0070) 2010; 20 Lowe, Tolman, Hillmyer (b0060) 2009; 10 Pearson (b0215) 1963; 85 Alcántara, Hernaiz, Sinisterra (b0015) 2011 Caovilla, Caovilla, Pergher, Esmelindro, Fernandes, Dariva, Bernardo-Gusmão, Oestreicher, Antunes (b0030) 2008; 133–135 Alarcon, Lamilla, Cespedes (b0075) 2013; 42 Reckien, Janetzko, Peintinger, Bredow (b0165) 2012; 33 Zhang, Lu, Yang, Hu, Yuan, Wang, Liu, Yue, Zhou, Xia (b0050) 2021; 499 (accessed November 12, 2023). Di, Cortés (b0235) 2017; 121 Bhatia, McGinty, Letizia, Api (b0085) 2008; 46 Gallego-Villada, Alarcón, Ruiz, Romanelli (b0190) 2022; 528 Ravasio, Zaccheria, Guidotti, Psaro (b0100) 2004; 27 Alonso-Doncel, Giner, de la Calle, Cueto, Horcajada, García-Muñoz, Serrano (b0135) 2023; 23 Takano, Houk (b0180) 2005; 1 Stekrova, Kumar, Díaz, Mäki-Arvela, Murzin (b0080) 2015; 241 Demidova, Suslov, Simakova, Volcho, Salakhutdinov, Simakova, Murzin (b0055) 2016; 420 del Mar Alonso-Doncel, Ochoa-Hernández, Gómez-Pozuelo, Oliveira, González-Aguilar, Peral, Sanz, Serrano (b0130) 2023; 80 Lasne, Mäki-Arvela, Aho, Vajglova, Eränen, Kumar, Sánchez-Velandia, Peurla, Mondelli, Pérez-Ramírez, Murzin (b0185) 2022; 405 Murzin, Wärnå, Haario, Salmi (b0200) 2021; 133 Vaschetti, Cánepa, Barrera, Sapag, Eimer, Casuscelli (b0025) 2020; 481 Lu, Hu, Hou, Wang (b0155) 2013; 1015 Gallego-Villada, Alarcón, Cerrutti, Blustein, Sathicq, Romanelli (b0195) 2023; 62 Sánchez-Velandia, Villa (b0110) 2022; 394–396 Murzin, Salmi (b0150) 2005 Miller, Loy, Rosokha (b0225) 2021; 6 Cotta, Martins, Pereira, da Silva Rocha, Kozhevnikova, Kozhevnikov, Gusevskaya (b0005) 2019; 584 Shao, Mei, Sundholm, Kaila (b0175) 2020; 16 Pearson (b0220) 1987; 64 Kouznetsov, Vladímir, Urbina, Stashenko (b0065) 2005; 50 Grimme, Antony, Ehrlich, Krieg (b0160) 2010; 132 Gallego-Villada, Cueto, Alonso-Doncel, Mäki-Arvela, Alarcón, Serrano, Murzin (b0125) 2024 Bianchi, Gervasio, Marabello (b0230) 2005; 8 Alonso-Doncel, Peral, Shamzhy, Čejka, Sanz, Serrano (b0140) 2020; 345 Vasconcellos-Dias, Nunes, Félix, Brandão, Calhorda (b0045) 2021; 519 Costa, da Silva Rocha, Kozhevnikov, Kozhevnikova, Gusevskaya (b0105) 2013; 3 Arata, Akutagawa, Tanabe (b0120) 1976; 41 Haario (b0205) 1994 Sánchez-Velandia, Gallego-Villada, Mäki-Arvela, Sidorenko, Yu (b0020) 2024 Gallego-Villada, Mäki-Arvela, Kumar, Alarcón, Vajglová, Tirri, Angervo, Lassfolk, Lastusaari, Murzin (b0040) 2024; 372 Kumar, Mäki-Arvela, Diáz, Aho, Demidova, Linden, Shepidchenko, Tenhu, Salonen, Laukkanen, Lashkul, Dahl, Sinev, Leino, Kordas, Salmi, Murzin (b0145) 2013; 56 Alcántara (10.1016/j.cej.2024.155377_b0015) 2011 Kumar (10.1016/j.cej.2024.155377_b0145) 2013; 56 Caovilla (10.1016/j.cej.2024.155377_b0030) 2008; 133–135 Dong (10.1016/j.cej.2024.155377_b0070) 2010; 20 Stekrova (10.1016/j.cej.2024.155377_b0080) 2015; 241 Haario (10.1016/j.cej.2024.155377_b0205) 1994 Di (10.1016/j.cej.2024.155377_b0235) 2017; 121 Kouznetsov (10.1016/j.cej.2024.155377_b0065) 2005; 50 Sánchez-Velandia (10.1016/j.cej.2024.155377_b0110) 2022; 394–396 Zhang (10.1016/j.cej.2024.155377_b0050) 2021; 499 Murzin (10.1016/j.cej.2024.155377_b0200) 2021; 133 Raptis (10.1016/j.cej.2024.155377_b0115) 2009; 48 Thompson (10.1016/j.cej.2024.155377_b0210) 1999; 110 Lowe (10.1016/j.cej.2024.155377_b0060) 2009; 10 Alonso-Doncel (10.1016/j.cej.2024.155377_b0135) 2023; 23 Lasne (10.1016/j.cej.2024.155377_b0185) 2022; 405 Sánchez-Velandia (10.1016/j.cej.2024.155377_b0020) 2024 Ravasio (10.1016/j.cej.2024.155377_b0100) 2004; 27 Alonso-Doncel (10.1016/j.cej.2024.155377_b0140) 2020; 345 Shao (10.1016/j.cej.2024.155377_b0175) 2020; 16 del Mar Alonso-Doncel (10.1016/j.cej.2024.155377_b0130) 2023; 80 Demidova (10.1016/j.cej.2024.155377_b0055) 2016; 420 Gallego-Villada (10.1016/j.cej.2024.155377_b0040) 2024; 372 Vaschetti (10.1016/j.cej.2024.155377_b0025) 2020; 481 Corma (10.1016/j.cej.2024.155377_b0095) 2007; 107 Lu (10.1016/j.cej.2024.155377_b0155) 2013; 1015 Grimme (10.1016/j.cej.2024.155377_b0160) 2010; 132 Nguyen (10.1016/j.cej.2024.155377_b0090) 2013; 03 Takano (10.1016/j.cej.2024.155377_b0180) 2005; 1 Gallego-Villada (10.1016/j.cej.2024.155377_b0125) 2024 Gallego-Villada (10.1016/j.cej.2024.155377_b0195) 2023; 62 Pearson (10.1016/j.cej.2024.155377_b0220) 1987; 64 10.1016/j.cej.2024.155377_b0010 Gallego-Villada (10.1016/j.cej.2024.155377_b0190) 2022; 528 Pearson (10.1016/j.cej.2024.155377_b0215) 1963; 85 Miller (10.1016/j.cej.2024.155377_b0225) 2021; 6 Bhatia (10.1016/j.cej.2024.155377_b0085) 2008; 46 Gallego-Villada (10.1016/j.cej.2024.155377_b0035) 2023; 62 Vasconcellos-Dias (10.1016/j.cej.2024.155377_b0045) 2021; 519 Alarcon (10.1016/j.cej.2024.155377_b0075) 2013; 42 Arata (10.1016/j.cej.2024.155377_b0120) 1976; 41 Costa (10.1016/j.cej.2024.155377_b0105) 2013; 3 Reckien (10.1016/j.cej.2024.155377_b0165) 2012; 33 Murzin (10.1016/j.cej.2024.155377_b0150) 2005 Bianchi (10.1016/j.cej.2024.155377_b0230) 2005; 8 Cotta (10.1016/j.cej.2024.155377_b0005) 2019; 584 Civalleri (10.1016/j.cej.2024.155377_b0170) 2008; 10 |
References_xml | – volume: 10 start-page: 405 year: 2008 end-page: 410 ident: b0170 article-title: B3LYP augmented with an empirical dispersion term (B3LYP-D*) as applied to molecular crystals publication-title: CrstEngComm contributor: fullname: Ugliengo – volume: 345 start-page: 27 year: 2020 end-page: 38 ident: b0140 article-title: Untangling the role of the organosilane functional groups in the synthesis of hierarchical ZSM-5 zeolite by crystallization of silanized protozeolitic units publication-title: Catal. Today. contributor: fullname: Serrano – volume: 1 start-page: 70 year: 2005 end-page: 77 ident: b0180 article-title: Benchmarking the conductor-like polarizable continuum model (CPCM) for aqueous solvation free energies of neutral and ionic organic molecules publication-title: J. Chem. Theory Comput. contributor: fullname: Houk – volume: 8 start-page: 1392 year: 2005 end-page: 1399 ident: b0230 article-title: The experimental charge density in transition metal compounds publication-title: Comptes Rendus Chim. contributor: fullname: Marabello – volume: 519 year: 2021 ident: b0045 article-title: New heptacoordinate tungsten(II) complexes with α-diimine ligands in the catalytic oxidation of multifunctional olefins publication-title: Inorganica Chim. Acta. contributor: fullname: Calhorda – volume: 405 start-page: 288 year: 2022 end-page: 302 ident: b0185 article-title: Synthesis of florol via prins cyclization over heterogeneous catalysts publication-title: J. Catal. contributor: fullname: Murzin – volume: 107 start-page: 2411 year: 2007 end-page: 2502 ident: b0095 article-title: Chemical routes for the transformation of biomass into chemicals publication-title: Chem. Rev. contributor: fullname: Velty – volume: 133 start-page: 1 year: 2021 end-page: 15 ident: b0200 article-title: Parameter estimation in kinetic models of complex heterogeneous catalytic reactions using Bayesian statistics publication-title: React. Kinet. Mech. Catal. contributor: fullname: Salmi – volume: 46 start-page: S85 year: 2008 end-page: S87 ident: b0085 article-title: Fragrance material review on carveol publication-title: Food Chem. Toxicol. contributor: fullname: Api – volume: 499 year: 2021 ident: b0050 article-title: Efficient air epoxidation of cycloalkenes over bimetal-organic framework ZnCo-MOF materials publication-title: Mol. Catal. contributor: fullname: Xia – volume: 42 start-page: 268 year: 2013 end-page: 272 ident: b0075 article-title: Insecticidal activity of sesquiterpenes skeleton synthesized by the conventional Robinson annulations reaction on Drosophila melanogaster publication-title: Ind. Crops Prod. contributor: fullname: Cespedes – volume: 584 year: 2019 ident: b0005 article-title: Heteropoly acid catalysis for the isomerization of biomass-derived limonene oxide and kinetic separation of the trans-isomer in green solvents publication-title: Appl. Catal. A Gen. contributor: fullname: Gusevskaya – volume: 241 start-page: 237 year: 2015 end-page: 245 ident: b0080 article-title: H- and Fe-modified zeolite beta catalysts for preparation of trans-carveol from α-pinene oxide publication-title: Catal. Today. contributor: fullname: Murzin – volume: 121 start-page: 9297 year: 2017 end-page: 9305 ident: b0235 article-title: Kinetics of the aqueous phase reactions of atmospherically relevant monoterpene epoxides publication-title: J. Phys. Chem. a. contributor: fullname: Cortés – volume: 110 start-page: 4221 year: 1999 end-page: 4228 ident: b0210 article-title: Quantum mechanical transition state theory and tunneling corrections publication-title: J. Chem. Phys. contributor: fullname: Thompson – volume: 372 year: 2024 ident: b0040 article-title: Zeolite Y-based catalysts for efficient epoxidation of R-(+)-limonene: Insights into the structure-activity relationship publication-title: Microporous Mesoporous Mater. contributor: fullname: Murzin – volume: 80 start-page: 77 year: 2023 end-page: 88 ident: b0130 article-title: Dendritic nanoarchitecture imparts ZSM-5 zeolite with enhanced adsorption and catalytic performance in energy applications publication-title: J. Energy Chem. contributor: fullname: Serrano – volume: 03 start-page: 206 year: 2013 end-page: 209 ident: b0090 article-title: Green synthesis of carvenone by montmorillonite-catalyzed isomerization of 1,2-limonene oxide publication-title: Int. J. Org. Chem. contributor: fullname: Le – volume: 48 start-page: 3133 year: 2009 end-page: 3136 ident: b0115 article-title: Selective isomerization of epoxides to allylic alcohols catalyzed by TiO publication-title: Angew. Chemie Int. Ed. contributor: fullname: Stratakis – start-page: 309 year: 2011 end-page: 331 ident: b0015 article-title: Biocatalyzed production of fine chemicals, in publication-title: Compr. Biotechnol., Second Edi, Elsevier contributor: fullname: Sinisterra – volume: 33 start-page: 2023 year: 2012 end-page: 2031 ident: b0165 article-title: Implementation of empirical dispersion corrections to density functional theory for periodic systems publication-title: J. Comput. Chem. contributor: fullname: Bredow – volume: 62 start-page: 20152 year: 2023 end-page: 20169 ident: b0035 article-title: Versatile heterogeneous catalytic system for the selective synthesis of limonene epoxide and diepoxide publication-title: Ind. Eng. Chem. Res. contributor: fullname: Villa – volume: 27 start-page: 157 year: 2004 end-page: 168 ident: b0100 article-title: Mono- and bifunctional heterogeneous catalytic transformation of terpenes and terpenoids publication-title: Top. Catal. contributor: fullname: Psaro – volume: 1015 start-page: 64 year: 2013 end-page: 71 ident: b0155 article-title: An improved B3LYP method in the calculation of organic thermochemistry and reactivity publication-title: Comput. Theor. Chem. contributor: fullname: Wang – volume: 394–396 start-page: 208 year: 2022 end-page: 218 ident: b0110 article-title: Selective synthesis of high-added value chemicals from α-pinene epoxide and limonene epoxide isomerization over mesostructured catalysts: Effect of the metal loading and solvent publication-title: Catal. Today. contributor: fullname: Villa – volume: 41 start-page: 173 year: 1976 end-page: 179 ident: b0120 article-title: Isomerization of d-limonene oxide over solid acids and bases publication-title: J. Catal. contributor: fullname: Tanabe – volume: 56 start-page: 696 year: 2013 end-page: 713 ident: b0145 article-title: Isomerization of α-pinene oxide over iron-modified zeolites publication-title: Top. Catal. contributor: fullname: Murzin – year: 1994 ident: b0205 article-title: ModEst user’s guide contributor: fullname: Haario – volume: 85 start-page: 3533 year: 1963 end-page: 3539 ident: b0215 article-title: Hard and soft acids and bases publication-title: J. Am. Chem. Soc. contributor: fullname: Pearson – volume: 133–135 start-page: 695 year: 2008 end-page: 698 ident: b0030 article-title: Catalytic oxidation of limonene, α-pinene and β-pinene by the complex [FeIII(BPMP)Cl(μ-O)FeIIICl3] biomimetic to MMO enzyme publication-title: Catal. Today. contributor: fullname: Antunes – volume: 62 start-page: 10915 year: 2023 end-page: 10929 ident: b0195 article-title: Levulinic acid esterification with n -butanol over a Preyssler catalyst in a microwave-assisted batch reactor: A kinetic study publication-title: Ind. Eng. Chem. Res. contributor: fullname: Romanelli – volume: 16 start-page: 587 year: 2020 end-page: 600 ident: b0175 article-title: Benchmarking the performance of time-dependent density functional theory methods on biochromophores publication-title: J. Chem. Theory Comput. contributor: fullname: Kaila – volume: 420 start-page: 142 year: 2016 end-page: 148 ident: b0055 article-title: Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis publication-title: J. Mol. Catal. A Chem. contributor: fullname: Murzin – volume: 50 start-page: 559 year: 2005 end-page: 563 ident: b0065 article-title: N-Functionalization of dihydrocarvone: Obtainin aminocyclohexane derivatives and their spectrometric study publication-title: J. Chil. Chem. Soc. contributor: fullname: Stashenko – volume: 132 year: 2010 ident: b0160 article-title: A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu publication-title: J. Chem. Phys. contributor: fullname: Krieg – volume: 20 start-page: 6359 year: 2010 end-page: 6361 ident: b0070 article-title: The structure and antimalarial activity of dispiro-1,2,4,5-tetraoxanes derived from (+)-dihydrocarvone publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: Vennerstrom – volume: 3 start-page: 244 year: 2013 end-page: 250 ident: b0105 article-title: Heteropoly acid catalysts for the synthesis of fragrance compounds from biorenewables: isomerization of limonene oxide publication-title: Catal. Sci. Technol. contributor: fullname: Gusevskaya – volume: 528 year: 2022 ident: b0190 article-title: Kinetic study of the esterification of t-cinnamic acid over preyssler structure acid publication-title: Mol. Catal. contributor: fullname: Romanelli – start-page: 1 year: 2024 end-page: 126 ident: b0020 article-title: Murzin, Upgrading biomass to high-added value chemicals: synthesis of monoterpenes-based compounds using catalytic green chemical pathways publication-title: Catal. Rev. contributor: fullname: Yu – year: 2024 ident: b0125 article-title: Dendritic ZSM-5 zeolites as highly active catalysts for the valorization of monoterpene epoxides (submitted) publication-title: Green Chem. contributor: fullname: Murzin – volume: 23 start-page: 5658 year: 2023 end-page: 5670 ident: b0135 article-title: Synthesis of dendritic ZSM-5 Zeolite through micellar templating controlled by the amphiphilic organosilane chain length publication-title: Cryst. Growth Des. contributor: fullname: Serrano – volume: 10 start-page: 2003 year: 2009 end-page: 2008 ident: b0060 article-title: Oxidized dihydrocarvone as a renewable multifunctional monomer for the synthesis of shape memory polyesters publication-title: Biomacromolecules contributor: fullname: Hillmyer – year: 2005 ident: b0150 article-title: Catalytic kinetics contributor: fullname: Salmi – volume: 64 start-page: 561 year: 1987 ident: b0220 article-title: Recent advances in the concept of hard and soft acids and bases publication-title: J. Chem. Educ. contributor: fullname: Pearson – volume: 481 year: 2020 ident: b0025 article-title: Limonene oxyfunctionalization over Cu-modified silicates employing hydrogen peroxide and t-butyl hydroperoxide: Reaction pathway analysis publication-title: Mol. Catal. contributor: fullname: Casuscelli – volume: 6 start-page: 23588 year: 2021 end-page: 23597 ident: b0225 article-title: Examining a transition from supramolecular halogen bonding to covalent bonds: Topological analysis of electron densities and energies in the complexes of bromosubstituted electrophiles publication-title: ACS Omega contributor: fullname: Rosokha – start-page: 309 year: 2011 ident: 10.1016/j.cej.2024.155377_b0015 article-title: Biocatalyzed production of fine chemicals, in publication-title: Compr. Biotechnol., Second Edi, Elsevier contributor: fullname: Alcántara – volume: 345 start-page: 27 year: 2020 ident: 10.1016/j.cej.2024.155377_b0140 article-title: Untangling the role of the organosilane functional groups in the synthesis of hierarchical ZSM-5 zeolite by crystallization of silanized protozeolitic units publication-title: Catal. Today. doi: 10.1016/j.cattod.2019.11.031 contributor: fullname: Alonso-Doncel – volume: 50 start-page: 559 year: 2005 ident: 10.1016/j.cej.2024.155377_b0065 article-title: N-Functionalization of dihydrocarvone: Obtainin aminocyclohexane derivatives and their spectrometric study publication-title: J. Chil. Chem. Soc. doi: 10.4067/S0717-97072005000300006 contributor: fullname: Kouznetsov – volume: 42 start-page: 268 year: 2013 ident: 10.1016/j.cej.2024.155377_b0075 article-title: Insecticidal activity of sesquiterpenes skeleton synthesized by the conventional Robinson annulations reaction on Drosophila melanogaster publication-title: Ind. Crops Prod. doi: 10.1016/j.indcrop.2012.05.026 contributor: fullname: Alarcon – volume: 133 start-page: 1 year: 2021 ident: 10.1016/j.cej.2024.155377_b0200 article-title: Parameter estimation in kinetic models of complex heterogeneous catalytic reactions using Bayesian statistics publication-title: React. Kinet. Mech. Catal. doi: 10.1007/s11144-021-01974-1 contributor: fullname: Murzin – volume: 420 start-page: 142 year: 2016 ident: 10.1016/j.cej.2024.155377_b0055 article-title: Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis publication-title: J. Mol. Catal. A Chem. doi: 10.1016/j.molcata.2016.04.013 contributor: fullname: Demidova – volume: 584 year: 2019 ident: 10.1016/j.cej.2024.155377_b0005 article-title: Heteropoly acid catalysis for the isomerization of biomass-derived limonene oxide and kinetic separation of the trans-isomer in green solvents publication-title: Appl. Catal. A Gen. doi: 10.1016/j.apcata.2019.117173 contributor: fullname: Cotta – volume: 03 start-page: 206 year: 2013 ident: 10.1016/j.cej.2024.155377_b0090 article-title: Green synthesis of carvenone by montmorillonite-catalyzed isomerization of 1,2-limonene oxide publication-title: Int. J. Org. Chem. doi: 10.4236/ijoc.2013.33027 contributor: fullname: Nguyen – volume: 64 start-page: 561 year: 1987 ident: 10.1016/j.cej.2024.155377_b0220 article-title: Recent advances in the concept of hard and soft acids and bases publication-title: J. Chem. Educ. doi: 10.1021/ed064p561 contributor: fullname: Pearson – volume: 48 start-page: 3133 year: 2009 ident: 10.1016/j.cej.2024.155377_b0115 article-title: Selective isomerization of epoxides to allylic alcohols catalyzed by TiO2 -supported gold nanoparticles publication-title: Angew. Chemie Int. Ed. doi: 10.1002/anie.200805838 contributor: fullname: Raptis – year: 2005 ident: 10.1016/j.cej.2024.155377_b0150 contributor: fullname: Murzin – volume: 20 start-page: 6359 year: 2010 ident: 10.1016/j.cej.2024.155377_b0070 article-title: The structure and antimalarial activity of dispiro-1,2,4,5-tetraoxanes derived from (+)-dihydrocarvone publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2010.09.113 contributor: fullname: Dong – volume: 394–396 start-page: 208 year: 2022 ident: 10.1016/j.cej.2024.155377_b0110 article-title: Selective synthesis of high-added value chemicals from α-pinene epoxide and limonene epoxide isomerization over mesostructured catalysts: Effect of the metal loading and solvent publication-title: Catal. Today. doi: 10.1016/j.cattod.2021.09.011 contributor: fullname: Sánchez-Velandia – volume: 8 start-page: 1392 year: 2005 ident: 10.1016/j.cej.2024.155377_b0230 article-title: The experimental charge density in transition metal compounds publication-title: Comptes Rendus Chim. doi: 10.1016/j.crci.2004.12.015 contributor: fullname: Bianchi – volume: 33 start-page: 2023 year: 2012 ident: 10.1016/j.cej.2024.155377_b0165 article-title: Implementation of empirical dispersion corrections to density functional theory for periodic systems publication-title: J. Comput. Chem. doi: 10.1002/jcc.23037 contributor: fullname: Reckien – volume: 121 start-page: 9297 year: 2017 ident: 10.1016/j.cej.2024.155377_b0235 article-title: Kinetics of the aqueous phase reactions of atmospherically relevant monoterpene epoxides publication-title: J. Phys. Chem. a. doi: 10.1021/acs.jpca.7b09427 contributor: fullname: Di – volume: 56 start-page: 696 year: 2013 ident: 10.1016/j.cej.2024.155377_b0145 article-title: Isomerization of α-pinene oxide over iron-modified zeolites publication-title: Top. Catal. doi: 10.1007/s11244-013-0029-y contributor: fullname: Kumar – year: 1994 ident: 10.1016/j.cej.2024.155377_b0205 contributor: fullname: Haario – volume: 132 year: 2010 ident: 10.1016/j.cej.2024.155377_b0160 article-title: A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu publication-title: J. Chem. Phys. doi: 10.1063/1.3382344 contributor: fullname: Grimme – volume: 62 start-page: 20152 year: 2023 ident: 10.1016/j.cej.2024.155377_b0035 article-title: Versatile heterogeneous catalytic system for the selective synthesis of limonene epoxide and diepoxide publication-title: Ind. Eng. Chem. Res. doi: 10.1021/acs.iecr.3c02633 contributor: fullname: Gallego-Villada – volume: 62 start-page: 10915 year: 2023 ident: 10.1016/j.cej.2024.155377_b0195 article-title: Levulinic acid esterification with n -butanol over a Preyssler catalyst in a microwave-assisted batch reactor: A kinetic study publication-title: Ind. Eng. Chem. Res. doi: 10.1021/acs.iecr.3c00893 contributor: fullname: Gallego-Villada – volume: 27 start-page: 157 year: 2004 ident: 10.1016/j.cej.2024.155377_b0100 article-title: Mono- and bifunctional heterogeneous catalytic transformation of terpenes and terpenoids publication-title: Top. Catal. doi: 10.1023/B:TOCA.0000013550.28170.6a contributor: fullname: Ravasio – volume: 372 year: 2024 ident: 10.1016/j.cej.2024.155377_b0040 article-title: Zeolite Y-based catalysts for efficient epoxidation of R-(+)-limonene: Insights into the structure-activity relationship publication-title: Microporous Mesoporous Mater. doi: 10.1016/j.micromeso.2024.113098 contributor: fullname: Gallego-Villada – volume: 41 start-page: 173 year: 1976 ident: 10.1016/j.cej.2024.155377_b0120 article-title: Isomerization of d-limonene oxide over solid acids and bases publication-title: J. Catal. doi: 10.1016/0021-9517(76)90213-X contributor: fullname: Arata – volume: 528 year: 2022 ident: 10.1016/j.cej.2024.155377_b0190 article-title: Kinetic study of the esterification of t-cinnamic acid over preyssler structure acid publication-title: Mol. Catal. contributor: fullname: Gallego-Villada – volume: 6 start-page: 23588 year: 2021 ident: 10.1016/j.cej.2024.155377_b0225 article-title: Examining a transition from supramolecular halogen bonding to covalent bonds: Topological analysis of electron densities and energies in the complexes of bromosubstituted electrophiles publication-title: ACS Omega doi: 10.1021/acsomega.1c03779 contributor: fullname: Miller – volume: 10 start-page: 2003 year: 2009 ident: 10.1016/j.cej.2024.155377_b0060 article-title: Oxidized dihydrocarvone as a renewable multifunctional monomer for the synthesis of shape memory polyesters publication-title: Biomacromolecules doi: 10.1021/bm900471a contributor: fullname: Lowe – year: 2024 ident: 10.1016/j.cej.2024.155377_b0125 article-title: Dendritic ZSM-5 zeolites as highly active catalysts for the valorization of monoterpene epoxides (submitted) publication-title: Green Chem. doi: 10.1039/D4GC04003A contributor: fullname: Gallego-Villada – volume: 10 start-page: 405 year: 2008 ident: 10.1016/j.cej.2024.155377_b0170 article-title: B3LYP augmented with an empirical dispersion term (B3LYP-D*) as applied to molecular crystals publication-title: CrstEngComm doi: 10.1039/B715018K contributor: fullname: Civalleri – volume: 23 start-page: 5658 year: 2023 ident: 10.1016/j.cej.2024.155377_b0135 article-title: Synthesis of dendritic ZSM-5 Zeolite through micellar templating controlled by the amphiphilic organosilane chain length publication-title: Cryst. Growth Des. doi: 10.1021/acs.cgd.3c00326 contributor: fullname: Alonso-Doncel – ident: 10.1016/j.cej.2024.155377_b0010 – volume: 405 start-page: 288 year: 2022 ident: 10.1016/j.cej.2024.155377_b0185 article-title: Synthesis of florol via prins cyclization over heterogeneous catalysts publication-title: J. Catal. doi: 10.1016/j.jcat.2021.12.008 contributor: fullname: Lasne – volume: 16 start-page: 587 year: 2020 ident: 10.1016/j.cej.2024.155377_b0175 article-title: Benchmarking the performance of time-dependent density functional theory methods on biochromophores publication-title: J. Chem. Theory Comput. doi: 10.1021/acs.jctc.9b00823 contributor: fullname: Shao – volume: 481 year: 2020 ident: 10.1016/j.cej.2024.155377_b0025 article-title: Limonene oxyfunctionalization over Cu-modified silicates employing hydrogen peroxide and t-butyl hydroperoxide: Reaction pathway analysis publication-title: Mol. Catal. contributor: fullname: Vaschetti – volume: 1 start-page: 70 year: 2005 ident: 10.1016/j.cej.2024.155377_b0180 article-title: Benchmarking the conductor-like polarizable continuum model (CPCM) for aqueous solvation free energies of neutral and ionic organic molecules publication-title: J. Chem. Theory Comput. doi: 10.1021/ct049977a contributor: fullname: Takano – volume: 110 start-page: 4221 year: 1999 ident: 10.1016/j.cej.2024.155377_b0210 article-title: Quantum mechanical transition state theory and tunneling corrections publication-title: J. Chem. Phys. doi: 10.1063/1.478304 contributor: fullname: Thompson – volume: 80 start-page: 77 year: 2023 ident: 10.1016/j.cej.2024.155377_b0130 article-title: Dendritic nanoarchitecture imparts ZSM-5 zeolite with enhanced adsorption and catalytic performance in energy applications publication-title: J. Energy Chem. doi: 10.1016/j.jechem.2023.01.023 contributor: fullname: del Mar Alonso-Doncel – volume: 133–135 start-page: 695 year: 2008 ident: 10.1016/j.cej.2024.155377_b0030 article-title: Catalytic oxidation of limonene, α-pinene and β-pinene by the complex [FeIII(BPMP)Cl(μ-O)FeIIICl3] biomimetic to MMO enzyme publication-title: Catal. Today. doi: 10.1016/j.cattod.2007.12.107 contributor: fullname: Caovilla – volume: 107 start-page: 2411 year: 2007 ident: 10.1016/j.cej.2024.155377_b0095 article-title: Chemical routes for the transformation of biomass into chemicals publication-title: Chem. Rev. doi: 10.1021/cr050989d contributor: fullname: Corma – volume: 3 start-page: 244 year: 2013 ident: 10.1016/j.cej.2024.155377_b0105 article-title: Heteropoly acid catalysts for the synthesis of fragrance compounds from biorenewables: isomerization of limonene oxide publication-title: Catal. Sci. Technol. doi: 10.1039/C2CY20526B contributor: fullname: Costa – volume: 85 start-page: 3533 year: 1963 ident: 10.1016/j.cej.2024.155377_b0215 article-title: Hard and soft acids and bases publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00905a001 contributor: fullname: Pearson – start-page: 1 year: 2024 ident: 10.1016/j.cej.2024.155377_b0020 article-title: Murzin, Upgrading biomass to high-added value chemicals: synthesis of monoterpenes-based compounds using catalytic green chemical pathways publication-title: Catal. Rev. doi: 10.1080/01614940.2024.2329553 contributor: fullname: Sánchez-Velandia – volume: 1015 start-page: 64 year: 2013 ident: 10.1016/j.cej.2024.155377_b0155 article-title: An improved B3LYP method in the calculation of organic thermochemistry and reactivity publication-title: Comput. Theor. Chem. doi: 10.1016/j.comptc.2013.04.009 contributor: fullname: Lu – volume: 499 year: 2021 ident: 10.1016/j.cej.2024.155377_b0050 article-title: Efficient air epoxidation of cycloalkenes over bimetal-organic framework ZnCo-MOF materials publication-title: Mol. Catal. contributor: fullname: Zhang – volume: 241 start-page: 237 year: 2015 ident: 10.1016/j.cej.2024.155377_b0080 article-title: H- and Fe-modified zeolite beta catalysts for preparation of trans-carveol from α-pinene oxide publication-title: Catal. Today. doi: 10.1016/j.cattod.2013.12.004 contributor: fullname: Stekrova – volume: 46 start-page: S85 year: 2008 ident: 10.1016/j.cej.2024.155377_b0085 article-title: Fragrance material review on carveol publication-title: Food Chem. Toxicol. doi: 10.1016/j.fct.2008.06.032 contributor: fullname: Bhatia – volume: 519 year: 2021 ident: 10.1016/j.cej.2024.155377_b0045 article-title: New heptacoordinate tungsten(II) complexes with α-diimine ligands in the catalytic oxidation of multifunctional olefins publication-title: Inorganica Chim. Acta. doi: 10.1016/j.ica.2021.120263 contributor: fullname: Vasconcellos-Dias |
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Title | Synthesis of dihydrocarvone over dendritic ZSM-5 Zeolite: A comprehensive study of experimental, kinetics, and computational insights |
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