Method for producing 3-methylcycloalkenone compound
AssigneeTakasago International Corporation
InventorHironori Maeda
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Abstract
The present invention relates to a method for producing a 3-methylcycloalkenone compound and a method for producing muscone. In the presence of a zirconium oxide catalyst, a diketone represented by the following general formula (1): wherein in formula (1), n represents 8, 9, 10, 11 or 12, is subjected to a vapor-phase intramolecular condensation reaction, whereby a 3-methylcycloalkenone compound can be produced with high reaction efficiency. When a 3-methylcyclopentadecenone compound produced by this method is hydrogenated in a known manner, muscone can be produced efficiently.
Claims20
A method for producing a 3-methylcycloalkenone compound represented by the following general formula (2), comprising vaporizing a diketone represented by the following general formula (1):
- wherein in formula (1), n represents 8, 9, 10, 11 or 12, and contacting the vaporized diketone of formula (1) with a catalyst consisting of zirconium oxide and an optional additional metal oxide, wherein an amount of the optional additional metal oxide in the catalyst is 3 mass % or less, to cause a vapor-phase intramolecular condensation reaction thereby producing a 3-methylcycloalkenone compound represented by the following general formula (2):
- wherein in formula (2), among the three double lines each consisting of solid and dotted lines, one represents a double bond and the other two represent single bonds, in which the configuration of the double bond may be either cis or trans, and n is as defined in general formula (1), wherein a mass ratio of the vaporized diketone of formula (1) to the catalyst is 0.2 or more.
A method for producing muscone, comprising vaporizing 2,15-hexadecanedione;
- and contacting the vaporized 2,15-hexadecanedione with a catalyst consisting of zirconium oxide and an optional additional metal oxide, wherein an amount of the optional additional metal oxide in the catalyst is 3 mass % or less, to cause a vapor-phase intramolecular condensation reaction thereby producing a 3-methylcyclopentadecenone compound represented by the following general formula (2′):
- wherein among the three double lines each consisting of solid and dotted lines, one represents a double bond and the other two represent single bonds, the configuration of the double bond may be either cis or trans, and n′ represents 10, wherein a mass ratio of the vaporized diketone of formula (1) to the catalyst is 0.2 or more, and hydrogenating the produced 3-methylcyclopentadecenone compound.
Dependencies are inferred from the claim text.