Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation
Abstract
:1. Introduction
2. Results and Discussion
2.1. trans-Anethole treatment with HY zeolites
Relative amount, %a | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|
Zeolite | HY1 | HY2 | HY3 | |||||||
Compd. | T, °C | 30 | 60 | 90 | 30 | 60 | 90 | 30 | 60 | 90 |
c is-Anethole | 0.3 ± 0.02 | 1.9 ± 0.24 | 0.8 ± 0.01 | 0.2 ± 0.01 | 1.2 ± 0.80 | 0.9 ± 0.11 | 0.2 ± 0.03 | 1.2 ± 0.08 | 0.4 ± 0.06 | |
trans-Anethole | 99 ± 0.02 | 45.0 ± 0.80 | 9.0 ± 0.86 | 99 ± 0.01 | 30 ± 23 | 12 ± 1.1 | 99.0 ± 1.7 | 76 ± 1.4 | 8.0 ± 1.9 | |
2a | --- | 2 ± 0.17 | 3 ± 0.16 | --- | 2.7 ± 0.92 | 2 ± 0.08 | --- | 0.4 ± 0.18 | 1.4 ± 0.17 | |
2b | --- | 1.0 ± 0.08 | 0.9 ± 0.03 | --- | 1.7 ± 0.74 | 4 ± 0.24 | --- | 0.7 ± 0.05 | 2.6 ± 0.27 | |
3a.3b | --- | 2.0 ± 0.06 | 9.0 ± 0.03 | --- | 5 ± 2.02 | 9 ± 0.09 | --- | 1.0 ± 0.19 | 23 ± 2.2 | |
4a | --- | 1.0 ± 0.08 | 3 ± 0.04 | --- | 1.0 ± 0.38 | 5 ± 0.06 | --- | 0.45 ± 0.05 | 2.2 ± 0.18 | |
4b | --- | 2.0 ± 0.05 | 11 ± 0.11 | --- | 3.0 ± 1.14 | 7 ± 1.3 | --- | 0.71 ± 0.06 | 5.9 ± 1.2 | |
5a | --- | tr | tr | --- | tr | tr | --- | tr | tr | |
5b | --- | 45 ± 0.30 | 63 ± 0.92 | --- | 55 ± 18 | 60 ± 0.4 | --- | 20 ± 1.2 | 57 ± 5.6 |
2.2. Transformation of trans-anethole exposed to deuterated zeolite, HDY
2.3. trans-Anethole phototransformation
Dimer | Molecular structure, R = p-Methoxy-phenyl | DB-5 column | tR, min (Polar column, DB-WAX) | Dipole moment, Debye | EI (eV) | |
---|---|---|---|---|---|---|
tR, min (Fig. 3) | RI | |||||
6a | | 29.6 | 2139 | --- | 2.11 | 7.90 |
6b | | 30.2 | 2106 | --- | 3.00 | 8.30 |
6c | | 30.9 | 2266 | 142.8 | 2.54 | 8.10 |
6d | | 30.5 | 2289 | --- | 2.53 | 8.29 |
6e | | 31.1 | 2255 | 151.4 | 2.37 | 8.27 |
T ºC | trans- Anethole conversion, % | Selectivity, % | |||||
---|---|---|---|---|---|---|---|
cis-anethole | 6a | 6b | 6c | 6d | 6e | ||
-5 | 30 | 42 | <1 | 2 | 5 | 1 | 50 |
5 | 35 | 38 | <1 | 2 | 5 | 2 | 54 |
15 | 52 | 34 | <1 | <1 | 8 | 1 | 57 |
2.4. Quantum yield of trans-anethole photoisomerization
T (ºC) | cis-Anethole a | 6c Dimer b | 6e Dimer c |
---|---|---|---|
-5 | 0.09 | 6 | 0.08 |
+5 | 0.11 | 5 | 0.09 |
+15 | 0.12 | 5 | 0.10 |
3. Experimental
3.1. General
3.2. Faujasite preparation and characterization
3.3. Zeolite characterization
3.4. trans-Anethole treatment with dealuminated HY zeolites
3.5. trans-Anethole treatment with deuterated HY zeolite
3.6. Phototransformation kinetics
3.7. Quantum yield determination
4. Conclusions
Acknowledgements
References
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Castro, H.T.; Martínez, J.R.; Stashenko, E. Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation. Molecules 2010, 15, 5012-5030. https://doi.org/10.3390/molecules15075012
Castro HT, Martínez JR, Stashenko E. Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation. Molecules. 2010; 15(7):5012-5030. https://doi.org/10.3390/molecules15075012
Chicago/Turabian StyleCastro, Hans T., Jairo René Martínez, and Elena Stashenko. 2010. "Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation" Molecules 15, no. 7: 5012-5030. https://doi.org/10.3390/molecules15075012