Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Reexamination Certificate
2001-11-01
2004-04-13
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
C512S008000, C512S026000, C568S375000
Reexamination Certificate
active
06720303
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to musk aroma-imparting, augmenting and enhancing mixtures of oxomacrocyclic compounds containing greater than about 40 weight % &Dgr;
3
-cyclotetradecen-1-one and greater than about 40 weight % cyclo-tetradecanone and less than about 5 weight % &Dgr;
2
-cyclotetradecen-1-one and a process for preparing such mixtures by means of a chemo-selective catalytic hydrogen of mixtures containing greater than 15% by weight of the &Dgr;
2
-cyclotetradecen-1-one and greater than 45% by weight of the &Dgr;
3
-cyclotetradecen-1-one.
There has been considerable work performed relating to substances which can be used to impart, alter, modify or enhance fragrances to or in various consumable materials. These substances are used to diminish the use of natural materials particularly in the musk aroma area where the use of natural materials is being replaced by the use of synthetic materials which provide more uniform and predictable properties in the finished product. Strong, substantive, sweet, warm, natural “animal-musk” aromas with an absence of oily and waxy nuances in the topnotes, middle notes and undertones, heretofore have been highly sought after by those skilled in the perfumery arts.
BACKGROUND OF THE INVENTION
Thus, prior art “animal-musk” aroma-imparting, augmenting and enhancing mixtures containing significant concentrations of cyclotetradecanone, &Dgr;
2
-cyclo-tetradecen-1-one and &Dgr;
3
-cyclotetradecen-1-one, for example, those disclosed in U.S. Pat. No. 4,183,965 issued on Jan. 15, 1980, the disclosure of which is incorporated herein by reference, and those disclosed by Stork and Macdonald at pages 1264 and 1265 of the Journal of the American Chemical Society, Volume 97, No.5, Mar. 5, 1975 which have desirable musk aromas all have the undesirable oily and waxy nuances present in their topnotes, middle notes and undertones, and impart these nuances to finished products produced therefrom.
Thus, nothing in the prior art discloses or suggests cyclotetradecanone/mono-unsaturated cyclotetradecen-1-one mixtures which have desirable natural “animal-musk” aromas but which have no oily and waxy nuances present in the topnotes, middle notes or undertones thereof. We have now discovered that the direct cause of the presence of such waxy and oily notes is the presence in the aroma-imparting, augmenting and enhancing mixture of significant concentrations, greater than 15 weight % on a solvent-free basis, of the isomer, &Dgr;
2
-cyclotetradecen-1-one; but if the concentration, on a solvent-free basis, were to be reduced to less than 5 weight % of the mixture, the existence of the oily and waxy nuances becomes imperceptible.
Accordingly, there exists a need for a practical method to produce cyclotetradecanone/&Dgr;
3
-mono-unsaturated cyclotetradecen-1-one mixtures which have the aforementioned desirable aroma properties but which have insignificant concentrations, less than 5 weight % on a solvent-free basis, of &Dgr;
2
-cyclotetradecen-1-one.
SUMMARY OF THE INVENTION
Our invention is directed to strong, substantive, sweet, warm, natural “animal-musk” aroma-imparting, augmenting and enhancing macrocyclic musk compositions which are mixtures consisting essentially of oxocarbocyclic compounds containing greater than about 40 weight % &Dgr;
3
-cyclotetradecen-1-one and greater than about 40 weight % cyclotetradecanone, less than 5 weight %, of &Dgr;
2
-cyclotetradecen-1-one.
More specifically, our invention is directed to macrocyclic musk compositions of matter consisting essentially of:
(a) from about 40 up to about 60 weight %, on a solvent-free basis, of cyclotetradecanone;
(b) from about 40 up to about 60 weight %, on a solvent-free basis, of &Dgr;
3
-cyclotetradecen-1-one; and
(c) less than 5 weight %, on a solvent-free basis, of &Dgr;
2
-cyclotetradecen-1-one, the weight ratio of cyclotetradecanone: &Dgr;
3
-cyclotetradecen-1-one being from about 6:4 down to about 4:6.
A preferred composition of our invention consists essentially of:
(a) about 50% by weight, on a solvent-free basis, of cyclotetradecanone;
(b) about 45% by weight, on a solvent-free basis, of &Dgr;
3
-cyclotetradecen-1-one; and
(c) less than 5 weight %, on a solvent-free basis, of &Dgr;
2
-cyclotetradecen-1-one.
The process of our invention for producing the macrocyclic musk compositions of our invention comprises the steps of:
(a) admixing a cyclotetradecenone reactant mixture comprising greater than 45% by weight of &Dgr;
3
-cyclotetradecen-1-one and greater than 15% by weight of &Dgr;
2
-cyclotetradecen-1-one with a hydrogenation reaction solvent to form a solvent-reactant mixture, with the weight ratio of solvent:cyclotetradecenone reactant mixture being from 20:70 up to 70:20;
(b) treating the resulting solvent-reactant mixture with hydrogen in the presence of a chemo-selective hydrogenation catalyst in a concentration of from about 0.1% up to about 0.5% by weight of the reaction mixture, at a temperature in the range of from about 15° C. up to about 35° C. and at a pressure of from about 0 psig up to about 100 psig thus forming a hydrogenated product reaction mass, whereby a composition comprising, on a solvent-free basis, greater than about 40% by weight of cyclotetradecanone, greater than about 40% by weight of &Dgr;
3
-cyclotetradecen-1-one and less than about 5% by weight of &Dgr;2-cyclotetradecen-1-one is produced; and
(c) recovering the resulting macrocyclic musk composition from the hydrogenated product reaction mass (preferably by means of vacuum distillation).
DETAILED DESCRIPTION OF THE INVENTION
Several techniques for the preparation of the cyclotetradecenone reactant mixtures may be used in the practice of our invention, for example:
(a) The process described in Example I at columns 11-14 of U.S. Pat. No. 4,183,965 issued on Jan. 15, 1980, the disclosure of which is incorporated herein by reference, or
(b) A process, as more particularly described herein in detail in Example I, infra, comprising the steps of (i) treating 3-hydroxycyclotetradecan-1-one in the vapor phase with a dehydrating quantity and concentration of anhydrous aluminum oxide particles, preferably from about 4 mesh up to about 8 mesh, at a dehydrating temperature, preferably from about 360° C. up to about 400° C., and pressure, preferably from about 1 mm Hg up to about 20 mm Hg, to form a dehydration product reaction mass and then (ii) recovering the cyclotetradecenone reactant mixture from the dehydration product reaction mass, preferably by means of vacuum distillation.
Preferably, the chemo-selective hydrogenation catalyst is a supported palladium catalyst containing from about 2 weight % palladium up to about 10 weight % palladium such as palladium on carbon, palladium on calcium carbonate and palladium on barium sulfate.
The hydrogenation reaction solvent is non-reactive with any reactant or reaction product, and is preferably methanol, ethanol, 2-propanol, 1-propanol, acetone, methylethylketone, methylisobutylketone, tetrahydrofuran or mixtures thereof.
A preferred set of hydrogenation reaction conditions is specifically set forth herein in Example II, infra.
Also, a preferred set of hydrogenation reaction conditions is as follows:
(i) Chemo-selective hydrogen catalyst: 5 weight % palladium on carbon;
(ii) Solvent: 2-propanol;
(iii) Hydrogenation reaction pressure: 100 psig;
(iv) Hydrogenation reaction temperature: 35° C.
(v) Weight ratio of solvent:reactant mixture: 50:50.
In carrying out the hydrogenation reaction of our invention, treatment of the solvent-reactant mixture with hydrogen causes the percentage P of &Dgr;
2
-cyclotetradecen-1-one in the composition to be reduced over the period of time, &thgr; (minutes) during which the hydrogenation takes place, according to either of the algorithms:
P=A
(
exp
)(−&thgr;
K
/&agr;)+
B
(1)
or
&thgr;={&agr;
ln A
(
P−B
)
−1
}
1/K
(2)
wherein &thgr; represents the time in minutes as measured from the commencement of the hydrogenation reaction; and &agr;, A, B an
Monteleone Michael G.
Mookherjee Braja Dulal
Narula Anubhav P. S.
Trenkle Robert W.
Cole Monique T.
International Flavors & Fragrances Inc.
Leightner Joseph F.
Warden Jill
LandOfFree
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