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Thermal Behavior of Pinan-2-ol and Linalool
Institute for Technical Chemistry and Environmental Chemistry (ITUC), Friedrich-Schiller University Jena, Lessingstr. 12, D-07743 Jena, Germany
Research and Development, DSM Nutritional Products, P.O. Box 2676, CH-4002 Basel, Switzerland
* Author to whom correspondence should be addressed.
Received: 29 May 2013; in revised form: 26 June 2013 / Accepted: 11 July 2013 / Published: 16 July 2013
Abstract: Linalool is an important intermediate for syntheses of isoprenoid fragrance compounds and vitamins A and E. One process option for its production is the thermal gas-phase isomerization of cis- and trans-pinan-2-ol. Investigations of this reaction were performed in a flow-type apparatus in a temperature range from 350–600 °C and a residence time range of 0.6–0.8 s. Rearrangement of the bicyclic alcohol led to linalool, plinols arising from consecutive reactions of linalool and other side products. Effects of residence time, temperature, surface-to-volume-ratio, carrier gas, and the presence of additives on yield and selectivity were studied. Furthermore, the effects of such parameters on ene-cyclization of linalool affording plinols were investigated. Results indicate that manipulation of the reaction in order to affect selectivity is difficult due to the large free path length to other molecules in the gas phase. However, conditions have been identified allowing one to increase the selectivity and the yield of linalool throughout pyrolysis of pinan-2-ol.
Keywords: biradicals; cyclobutane fragmentation; isomerization; pericyclic reactions; pyrolysis; terpenoids; thermal rearrangement
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Leiner, J.; Stolle, A.; Ondruschka, B.; Netscher, T.; Bonrath, W. Thermal Behavior of Pinan-2-ol and Linalool. Molecules 2013, 18, 8358-8375.
Leiner J, Stolle A, Ondruschka B, Netscher T, Bonrath W. Thermal Behavior of Pinan-2-ol and Linalool. Molecules. 2013; 18(7):8358-8375.
Leiner, Janne; Stolle, Achim; Ondruschka, Bernd; Netscher, Thomas; Bonrath, Werner. 2013. "Thermal Behavior of Pinan-2-ol and Linalool." Molecules 18, no. 7: 8358-8375.