Cleaning compositions for solid surfaces – auxiliary compositions – With oxygen – halogen – sulfur – or nitrogen containing or... – Ring in the component
Reexamination Certificate
1999-07-12
2001-01-09
Douyon, Lorna M. (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
With oxygen, halogen, sulfur, or nitrogen containing or...
Ring in the component
C510S108000, C510S119000, C510S152000, C510S276000, C510S367000, C510S394000, C424S076100, C424S076400, C424S401000, C044S275000, C512S022000, C514S844000
Reexamination Certificate
active
06172016
ABSTRACT:
This invention relates to the use of certain substituted pentane derivatives as perfumery materials.
BACKGROUND OF THE INVENTION
Many compounds have been described in the literature as fragrance materials. As is the case with many classes of compounds having varied utilities, of the many compounds that are known to possess pleasing fragrance notes, only a very small portion are utilized commercially. There are several reasons for this, notably toxicological constraints, environmental considerations, biodegradability, performance, and cost effectiveness. While all of these factors must be carefully weighed in consideration of whether to introduce a new fragrance material, perhaps the most critical are performance and cost. Performance properties include odor activity, notes, and aesthetics; substantivity; and solubility. The cost effectiveness involves manufacture costs and the amount of the compound required to impart fragrance to a consumable product. Of course, the lower the amount of fragrance material required, the higher its cost effectiveness. Many materials have met some of the above-mentioned criteria, yet have not been successful because of cost versus performance.
It must further be borne in mind that, because fragrance materials are by nature utilized in comparatively small quantities, only a very few benefit from the cost efficiency of large-scale production. All of these factors, combined with the tendency in many countries to take a more rigid regulatory position concerning ingredients in consumable products, have acted to hamper the introduction of new fragrance materials in recent years.
There is an on-going need for new fragrance materials that can be readily synthesized from relatively inexpensive raw materials, meet the criteria set forth above, possess unique fragrance notes and, perhaps most importantly, are cost-effective in use. Such materials are provided in accordance with the present invention.
SUMMARY OF THE INVENTION
The invention relates to the use of 3-methyl-5-cyclohexylpentanol, 3-methyl-5-cyclohexylpentanal and mixtures thereof as fragrance materials.
DETAILED DESCRIPTION OF THE INVENTION
The compounds found to possess attractive fragrance properties in accordance with the present invention are 3-methyl-5-cyclohexylpentanol, having the structural formula
(C6H11)-CH2-CH2-CH(CH3)-CH2-CH2OH
and 3-methyl-5-cyclohexylpentanal, having the structure
(C6H11)-CH2-CH2-CH(CH3)-CH2-CHO.
Both of these compounds are known in the literature, but there has been to date neither recognition of their fragrant properties nor suggestion that they may possess such properties.
The preparation of 3-methyl-5-cyclohexylpentanol for a configurational relationship study was disclosed by Levene and Marker, J. Biol. Chem. Vol. 110, pages 311-321 (1935). German Offenlegungsschrift 24 44 837 (1975) discloses the preparation of 3-methyl-5-cyclohexyl pentanol, and 3-methyl-5-cyclohexylpentanal as well as intermediates in the preparation of compounds having juvenile hormone activity. Neither citation gives any indication that either of the compounds of the invention might possess fragrant properties.
3-Methyl-5-cyclohexylpentanol is conveniently prepared by hydrogenation of 3-methyl-5-phenylpentanol, a known material. Hydrogenation of phenyl rings is well known in the art and the particular method for accomplishing the above transformation is not critical. Those of ordinary skill in the art will readily appreciate that temperature, solvent, catalyst, pressure, and mixing rate, parameters that effect the hydrogenation, and how such relationships may be adjusted the relationships among them to effect the desired conversion, reaction rate, selectivity, and apparatus limitations.
The above hydrogenation is preferably carried out in a solvent at elevated temperatures and pressures over a suitable active metal hydrogenation catalyst. Acceptable solvents, catalysts, apparatus, and procedures for aromatic hydrogenation can be found in Augustine, Heterogeneous Catalysis for the Synthetic Chemist, Marcel Decker, New York, N.Y. (1996), incorporated herein by reference. Many hydrogenation catalysts are effective, including, without limitation, palladium, platinum, copper chromite, copper, rhodium, ruthenium and the supported versions thereof. Supported catalysts are preferred because the active metal is used more efficiently. Supported nickel is the preferred catalyst. Preferred supports include alumina, silica, carbon, titania, and kieselguhr, with silica and alumina being particularly preferred. While the weight percent of nickel on the support is not critical, it will be appreciated that the higher the metal weight percent the faster the reaction. Generally the nickel weight percent will range from about 5 to about 95%, preferably 25 to 75%, and most preferably 45 to 65%.
The temperature, amount of supported nickel catalyst, and hydrogenation hydrogen pressure are interrelated. The preferred temperature is from about 50° to 500° C., more preferably from about 100° to about 300° C., and most preferably from about 140° to 200° C. According to these temperature parameters, the amount of metal is preferably about 0.01 to 10 weight percent—relative to the weight of the total reaction mixture—preferably 1 to 5%, most preferably 2 to 3% by weight. The hydrogen pressure is preferably about 50 to about 5000 psi, more preferably about 100 to 1000 psi, and most preferably about 200 to 700 psi. Useful solvents include those well known in the art of hydrogenation, such as, hydrocarbons, ethers, and alcohols. Alcohols are most preferred, particularly lower alkanols such as methanol, ethanol, propanol, butanol, and pentanol. Most preferred is to use no added solvent, i.e., the substrate and product alcohols function as solvents.
3-Methyl-5-cyclohexylpentanal is likewise conveniently prepared by the oxidation of 3-methyl-5-cyclohexylpentanol by methods well known to those of skill in art. Oxidation of alcohols to aldehydes is a well known reaction. Typical reagents for effecting this transformation are pyridinium chlorochromate (available from Aldrich Chemical Co.; procedure in Tetrahedron Letters, 1975, page 2647 and Synthesis, 1982, page 245), or preferably catalytic TEMPO free radical [available from Aldrich Chemical Co.; i.e. 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical] with buffered aqueous hypochlorite in the presence of potassium bromide. The procedure for this oxidation can be found in Anelli, P. et al., Org. Syn. Coll. Vol. 8, page 367 (1993). The TEMPO oxidation is preferably performed by adding 12% sodium hypochlorite (1.05 equivalents, buffered to pH 9.6 with sodium bicarbonate), to a well stirred, cooled (0° C.) solution consisting of the alcohol, 10 mole % of potassium bromide, and 1 mole % TEMPO in 5 equivalents of methylene chloride or toluene. The buffered hypochorite is added at such a rate so that the temperature of the reaction medium does not rise above 5° C. After the addition is complete, the reaction mixture is allowed to warm to room temperature and stir for fifteen minutes. The organic layer is dried, concentrated and vacuum distilled to afford the pure andehyde.
The compounds of the present invention, in contrast to the corresponding nitrile compound, i.e. 3-methyl-5-cyclohexylpentanonitrile, which is known as a citrus odorant, possess strong, fatty, rosy, waxy, muguet, carbinol, woody fragrance notes with slightly green, Phenoxanol™-like top note character. The unique fragrance notes of the subject compounds make them useful in imparting, augmenting or enhancing the olfactory component in perfume or perfume articles whether that component is intended to impart a characteristic perfume to the article or mask or modify the odor of one or more of the components thereof.
As those skilled in the art will appreciate, fragrant materials are typically utilized in combinations that may include both natural and synthetic ingredients to achieve the desired overall perfume effect. The compounds of the present invention possess unique fragrant notes and, therefore, are p
Frank Walter C.
Pagano Alex R.
Bush Boakes Allen Inc.
Douyon Lorna M.
Gibbons Del Deo Dolan Griffinger & Vecchione
LandOfFree
Fragrance materials does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fragrance materials, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fragrance materials will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2500365