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Volkswagen Seat is not the only manufacturer to have its own mapping technology.1. Field of the Invention
The invention is directed to a process for the production of 4-hydroxy-2(E)-alkenals by catalytic hydrogenation of geranyl geraniol in the presence of ruthenium catalysts. The 4-hydroxy-2(E)-alkenals can be used as intermediates for the production of other useful intermediate compounds.
2. Description of Related Art
Dihydropyrans are very useful for the preparation of valuable intermediate compounds for the production of pharmaceuticals, such as prostaglandins and prostacyclins, and for the synthesis of fine chemicals. Thus, the development of economical processes for the production of dihydropyrans is of interest. However, dihydropyrans are notoriously difficult to prepare by chemical syntheses [D. Klessinger, “Vinylketals and Dihydropyrans: Modern Syntheses Based on the Carbene-Lewis-Criegee Mechanism” in Carbocationic Reactions: Multicenter and Multinuclear Reactions, H. Rehdiger, H. J. Rehr and G. Dancker-Voegtle, eds., Vol. 1 (2000), Wiley-VCH].
Hydrogenation of diene systems is a known method for the production of such compounds. Thus, catalysts comprising rhodium (see, for example, U.S. Pat. Nos. 5,338,778, 5,543,401 and 5,554,730, JP-81442/96, DE-19622645, EP-702349), ruthenium (JP-A-08107126, JP-A-02009029) and iron (WO 96/08523) catalysts have been disclosed. However, even with these rhodium-, ruthenium- and iron-catalyzed hydrogenation processes diene systems generally give poor dihydropyran yields.
U.S. Pat. Nos. 5,374,719 and 5,354,861 disclose the use of ruthenium catalysts for the hydrogenation of geranyl geraniol in the presence of silica gel to produce 4-hydroxy-2(E)-alkenals. There is no disclosure of the subsequent use of the 4-hydroxy-2(E)-alken