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AssigneeBASF SE
InventorsRichard Dehn, Joaquim Henrique Teles, Michael Limbach, Stephan Deuerlein, Manuel Danz, Ralf Pelzer, Daniel Schneider
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The present invention relates to a process for preparing cyclic compounds having at least eight carbon atoms and at least one keto group, to the cyclic compounds obtained by this process and to the use thereof, in particular as fragrance or for providing a fragrance.
A process for preparing at least one cyclic compound having at least eight carbon atoms and at least one keto group, wherein
Dependencies are inferred from the claim text.
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By isomerisation; by change of size of the carbon skeleton: by increase in the number of carbon atoms
By isomerisation; by change of size of the carbon skeleton: by change of size of the carbon skeleton
Ketones; Ketenes; Dimeric ketenes ; Ketonic chelates: unsaturated compounds containing keto groups bound to rings other than six-membered aromatic…
Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings: to a seven- to twelve-membered ring
About 6 years 8 months of term left · ends 12 Jun 2033 (estimated)
The present invention relates to a process for preparing cyclic compounds having at least eight carbon atoms and at least one keto group, to the cyclic compounds obtained by this process and to the use thereof, in particular as fragrance or for providing a fragrance.
There is a need for effective processes for preparing cyclic compounds based on medium and specifically based on large rings which have at least one keto group. Medium rings generally have 8 to 11 carbon atoms, above 12 carbon atoms one talks of large rings, and compounds based on large rings are also referred to as macrocyclic compounds. Macrocyclic ketones, lactones and epoxides as well as further functionalized macrocycles are aroma chemicals valued in the fragrance industry. Important representatives are e.g. muscone (1), (E/Z)-8-cyclohexadecenone (2), cyclohexadecanone (3) or 9-hexadecen-16-olide (4).
The known processes for preparing cyclic ketones are generally associated with considerable synthetic expenditure. Thus, A. S. Williams gives, in Synthesis 1999, 10, 1707-1723, an overview of the synthesis of macrocyclic musk compounds. For example, the preparation of muscone (1) takes place according to this in a multistage synthesis starting from cyclododecanone by ring expansion.
In step a) of the process according to the invention, pure cyclododeca-4,8-dienone or an industrially available cyclododeca-4,8-dienone-containing mixture can be used as cyclododeca-4,8-dienone-containing starting material.
Preferably, to provide the cyclododeca-4,8-dienone-containing starting material in step a), a 1,5,9-cyclododecatriene-containing composition is used and subjected to an oxidation, giving an oxidation product which comprises cyclododeca-4,8-dienone.
1,5,9-Cyclododecatriene can generally be used in the form of any possible isomer, for example cis,trans,trans-1,5,9-cyclododecatriene, cis,cis,trans-1,5,9-cyclododecatriene, all-trans-1,5,9-cyclododecatriene or all-cis-1,5,9-cyclododecatriene. In step a) of the process according to the invention, it is also possible to use an isomer mixture which comprises at least two of the aforementioned isomers.