Insight in the activity and diastereoselectivity of various Lewis acid catalysts for the citronellal cyclization

Both experiment and theory predict ATPH as most active and selective Lewis acid catalyst in the citronellal cyclization. [Display omitted] •Combined experimental and theoretical study on citronellal cyclization toward isopulegol stereoisomers.•Lewis acid homogeneous catalysts (ZnBr2 and ATPH) versus...

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Published in:	Journal of catalysis Vol. 305; pp. 118 - 129
Main Authors:	Vandichel, Matthias, Vermoortele, Frederik, Cottenie, Stijn, De Vos, Dirk E., Waroquier, Michel, Van Speybroeck, Veronique
Format:	Journal Article
Language:	English
Published:	Amsterdam Elsevier Inc 01.09.2013 Elsevier Elsevier BV
Subjects:	Acids Activity aluminum ATPH Catalysis Catalysts Chemical kinetics Chemistry citronellal Citronellal cyclization Cu-BTC Diastereoselective catalysis energy Exact sciences and technology General and physical chemistry Heterogeneous catalysis hydrogen Hydrogenation Lewis acids ligands nitrogen dioxide Selectivity stereoisomers temperature Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry ZnBr2 Heterogeneous catalysis Citronellal cyclization ATPH Chemical kinetics Lewis acids Diastereoselective catalysis Activity ZnBr2 Selectivity Cu-BTC Lewis acid Citronellal Catalytic reaction Diastereoselectivity ZnBr Cyclization Kinetics Catalyst
ISSN:	0021-9517, 1090-2694
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Abstract	Both experiment and theory predict ATPH as most active and selective Lewis acid catalyst in the citronellal cyclization. [Display omitted] •Combined experimental and theoretical study on citronellal cyclization toward isopulegol stereoisomers.•Lewis acid homogeneous catalysts (ZnBr2 and ATPH) versus Cu3BTC2 as hetereogeneous MOF catalyst.•Search for catalyst with the highest activity and highest selectivity toward (−)-isopulegol diastereomer.•ATPH is the most active catalyst with selectivity of about 94% at 298K.•Catalytic conversion in Cu3BTC2 strongly dependent on size of catalyst particles due to diffusional restrictions. Industrial (−)-menthol production generally relies on the hydrogenation of (−)-isopulegol, which is in turn produced with high selectivity by cyclization of (+)-citronellal. This paper uses a combined theoretical and experimental approach to study the activity and selectivity of three Lewis acid catalysts for this reaction, namely ZnBr2, aluminum tris(2,6-diphenylphenoxide) (ATPH), and the heterogeneous metal–organic framework Cu3BTC2 (BTC=benzene-1,3,5-tricarboxylate). ATPH is a strong Lewis acid homogeneous catalyst with bulky ligands which provides very high selectivities for the desired stereoisomer (>99%). The performance of the catalysts was evaluated as a function of temperature, which revealed that a higher catalyst activity allows working at lower temperatures and improves the selectivity for isopulegol. The selectivity distribution is kinetically driven for ZnBr2 and ATPH. The theoretical selectivity distributions rely on the determination of an extensive set of diastereomeric transition states, for which the differences in free energy have been calculated using a complementary set of ab initio techniques. Given the sensitivity of the selectivity to small Gibbs free-energy differences, the agreement between experimental and theoretical selectivities is satisfactory. On basis of the obtained insights, rational design of new catalysts may be obtained. As proof of concept, the hypothetical Cu3(BTC-(NO2)3)2 Lewis catalyst – in which each phenyl hydrogen of the BTC ligand is replaced by a nitro group – is predicted to be very selective.
AbstractList	Both experiment and theory predict ATPH as most active and selective Lewis acid catalyst in the citronellal cyclization. Display Omitted * Combined experimental and theoretical study on citronellal cyclization toward isopulegol stereoisomers. * Lewis acid homogeneous catalysts (ZnBr2 and ATPH) versus Cu3BTC2 as hetereogeneous MOF catalyst. * Search for catalyst with the highest activity and highest selectivity toward (-)-isopulegol diastereomer. * ATPH is the most active catalyst with selectivity of about 94% at 298K. * Catalytic conversion in Cu3BTC2 strongly dependent on size of catalyst particles due to diffusional restrictions. Industrial (-)-menthol production generally relies on the hydrogenation of (-)-isopulegol, which is in turn produced with high selectivity by cyclization of (+)-citronellal. This paper uses a combined theoretical and experimental approach to study the activity and selectivity of three Lewis acid catalysts for this reaction, namely ZnBr2, aluminum tris(2,6-diphenylphenoxide) (ATPH), and the heterogeneous metal-organic framework Cu3BTC2 (BTC=benzene-1,3,5-tricarboxylate). ATPH is a strong Lewis acid homogeneous catalyst with bulky ligands which provides very high selectivities for the desired stereoisomer (>99%). The performance of the catalysts was evaluated as a function of temperature, which revealed that a higher catalyst activity allows working at lower temperatures and improves the selectivity for isopulegol. The selectivity distribution is kinetically driven for ZnBr2 and ATPH. The theoretical selectivity distributions rely on the determination of an extensive set of diastereomeric transition states, for which the differences in free energy have been calculated using a complementary set of ab initio techniques. Given the sensitivity of the selectivity to small Gibbs free-energy differences, the agreement between experimental and theoretical selectivities is satisfactory. On basis of the obtained insights, rational design of new catalysts may be obtained. As proof of concept, the hypothetical Cu3(BTC-(NO2)3)2 Lewis catalyst - in which each phenyl hydrogen of the BTC ligand is replaced by a nitro group - is predicted to be very selective. Graphical abstract Both experiment and theory predict ATPH as most active and selective Lewis acid catalyst in the citronellal cyclization. Display Omitted Industrial (-)-menthol production generally relies on the hydrogenation of (-)-isopulegol, which is in turn produced with high selectivity by cyclization of (+)-citronellal. This paper uses a combined theoretical and experimental approach to study the activity and selectivity of three Lewis acid catalysts for this reaction, namely ZnBr2 , aluminum tris(2,6-diphenylphenoxide) (ATPH), and the heterogeneous metal-organic framework Cu3 BTC2 (BTC=benzene-1,3,5-tricarboxylate). ATPH is a strong Lewis acid homogeneous catalyst with bulky ligands which provides very high selectivities for the desired stereoisomer (>99%). The performance of the catalysts was evaluated as a function of temperature, which revealed that a higher catalyst activity allows working at lower temperatures and improves the selectivity for isopulegol. The selectivity distribution is kinetically driven for ZnBr2 and ATPH. The theoretical selectivity distributions rely on the determination of an extensive set of diastereomeric transition states, for which the differences in free energy have been calculated using a complementary set of ab initio techniques. Given the sensitivity of the selectivity to small Gibbs free-energy differences, the agreement between experimental and theoretical selectivities is satisfactory. On basis of the obtained insights, rational design of new catalysts may be obtained. As proof of concept, the hypothetical Cu3 (BTC-(NO2 )3 )2 Lewis catalyst - in which each phenyl hydrogen of the BTC ligand is replaced by a nitro group - is predicted to be very selective. [PUBLICATION ABSTRACT] Industrial (−)-menthol production generally relies on the hydrogenation of (−)-isopulegol, which is in turn produced with high selectivity by cyclization of (+)-citronellal. This paper uses a combined theoretical and experimental approach to study the activity and selectivity of three Lewis acid catalysts for this reaction, namely ZnBr₂, aluminum tris(2,6-diphenylphenoxide) (ATPH), and the heterogeneous metal–organic framework Cu₃BTC₂ (BTC=benzene-1,3,5-tricarboxylate). ATPH is a strong Lewis acid homogeneous catalyst with bulky ligands which provides very high selectivities for the desired stereoisomer (>99%). The performance of the catalysts was evaluated as a function of temperature, which revealed that a higher catalyst activity allows working at lower temperatures and improves the selectivity for isopulegol. The selectivity distribution is kinetically driven for ZnBr₂ and ATPH. The theoretical selectivity distributions rely on the determination of an extensive set of diastereomeric transition states, for which the differences in free energy have been calculated using a complementary set of ab initio techniques. Given the sensitivity of the selectivity to small Gibbs free-energy differences, the agreement between experimental and theoretical selectivities is satisfactory. On basis of the obtained insights, rational design of new catalysts may be obtained. As proof of concept, the hypothetical Cu₃(BTC-(NO₂)₃)₂ Lewis catalyst – in which each phenyl hydrogen of the BTC ligand is replaced by a nitro group – is predicted to be very selective. Both experiment and theory predict ATPH as most active and selective Lewis acid catalyst in the citronellal cyclization. [Display omitted] •Combined experimental and theoretical study on citronellal cyclization toward isopulegol stereoisomers.•Lewis acid homogeneous catalysts (ZnBr2 and ATPH) versus Cu3BTC2 as hetereogeneous MOF catalyst.•Search for catalyst with the highest activity and highest selectivity toward (−)-isopulegol diastereomer.•ATPH is the most active catalyst with selectivity of about 94% at 298K.•Catalytic conversion in Cu3BTC2 strongly dependent on size of catalyst particles due to diffusional restrictions. Industrial (−)-menthol production generally relies on the hydrogenation of (−)-isopulegol, which is in turn produced with high selectivity by cyclization of (+)-citronellal. This paper uses a combined theoretical and experimental approach to study the activity and selectivity of three Lewis acid catalysts for this reaction, namely ZnBr2, aluminum tris(2,6-diphenylphenoxide) (ATPH), and the heterogeneous metal–organic framework Cu3BTC2 (BTC=benzene-1,3,5-tricarboxylate). ATPH is a strong Lewis acid homogeneous catalyst with bulky ligands which provides very high selectivities for the desired stereoisomer (>99%). The performance of the catalysts was evaluated as a function of temperature, which revealed that a higher catalyst activity allows working at lower temperatures and improves the selectivity for isopulegol. The selectivity distribution is kinetically driven for ZnBr2 and ATPH. The theoretical selectivity distributions rely on the determination of an extensive set of diastereomeric transition states, for which the differences in free energy have been calculated using a complementary set of ab initio techniques. Given the sensitivity of the selectivity to small Gibbs free-energy differences, the agreement between experimental and theoretical selectivities is satisfactory. On basis of the obtained insights, rational design of new catalysts may be obtained. As proof of concept, the hypothetical Cu3(BTC-(NO2)3)2 Lewis catalyst – in which each phenyl hydrogen of the BTC ligand is replaced by a nitro group – is predicted to be very selective.
Author	Vermoortele, Frederik Vandichel, Matthias Waroquier, Michel Cottenie, Stijn De Vos, Dirk E. Van Speybroeck, Veronique
Author_xml	– sequence: 1 givenname: Matthias surname: Vandichel fullname: Vandichel, Matthias organization: Center for Molecular Modeling (CMM), Ghent University, Technologiepark 903, 9052 Zwijnaarde, Belgium – sequence: 2 givenname: Frederik surname: Vermoortele fullname: Vermoortele, Frederik organization: Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, 3001 Leuven, Belgium – sequence: 3 givenname: Stijn surname: Cottenie fullname: Cottenie, Stijn organization: Center for Molecular Modeling (CMM), Ghent University, Technologiepark 903, 9052 Zwijnaarde, Belgium – sequence: 4 givenname: Dirk E. surname: De Vos fullname: De Vos, Dirk E. email: dirk.devos@biw.kuleuven.be organization: Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, 3001 Leuven, Belgium – sequence: 5 givenname: Michel surname: Waroquier fullname: Waroquier, Michel organization: Center for Molecular Modeling (CMM), Ghent University, Technologiepark 903, 9052 Zwijnaarde, Belgium – sequence: 6 givenname: Veronique surname: Van Speybroeck fullname: Van Speybroeck, Veronique email: veronique.vanspeybroeck@ugent.be organization: Center for Molecular Modeling (CMM), Ghent University, Technologiepark 903, 9052 Zwijnaarde, Belgium
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Keywords	Heterogeneous catalysis Citronellal cyclization ATPH Chemical kinetics Lewis acids Diastereoselective catalysis Activity ZnBr2 Selectivity Cu-BTC Lewis acid Citronellal Catalytic reaction Diastereoselectivity ZnBr Cyclization Kinetics Catalyst
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Snippet	Both experiment and theory predict ATPH as most active and selective Lewis acid catalyst in the citronellal cyclization. [Display omitted] •Combined... Industrial (−)-menthol production generally relies on the hydrogenation of (−)-isopulegol, which is in turn produced with high selectivity by cyclization of... Graphical abstract Both experiment and theory predict ATPH as most active and selective Lewis acid catalyst in the citronellal cyclization. Display Omitted... Both experiment and theory predict ATPH as most active and selective Lewis acid catalyst in the citronellal cyclization. Display Omitted * Combined...
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SubjectTerms	Acids Activity aluminum ATPH Catalysis Catalysts Chemical kinetics Chemistry citronellal Citronellal cyclization Cu-BTC Diastereoselective catalysis energy Exact sciences and technology General and physical chemistry Heterogeneous catalysis hydrogen Hydrogenation Lewis acids ligands nitrogen dioxide Selectivity stereoisomers temperature Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry ZnBr2
Title	Insight in the activity and diastereoselectivity of various Lewis acid catalysts for the citronellal cyclization
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