US3760087A - Perfume compositions containing ethyl 2,4-dioxohexanoate - Google Patents
Perfume compositions containing ethyl 2,4-dioxohexanoate Download PDFInfo
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- US3760087A US3760087A US00004134A US3760087DA US3760087A US 3760087 A US3760087 A US 3760087A US 00004134 A US00004134 A US 00004134A US 3760087D A US3760087D A US 3760087DA US 3760087 A US3760087 A US 3760087A
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- dioxohexanoate
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
- C11D9/442—Perfumes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2028—Carboxy compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
Definitions
- ABSTRACT The present invention comprises perfume compositions containing ethyl 2,4-dioxohexanoate.
- the present invention comprises the discovery that ethyl 2,4-dioxohexanoate has a high odor value and desirable blending properties so as to be useful in perfume compositions.
- This invention also includes the discovery that ethyl 2,4-dioxohexanoate has a flavor value for use in flavored compositions.
- a compound must be fragrant and as pleasant as possible, yet not interfere with the purpose for which the final product is intended by significantly affecting factors like solubility, toxicity, color, etc.
- soap incorporat- For example, soap incorporat-,
- ing'an olfactory ingredient should desirably result in a finished product having a uniform fragrance, high odor stability and effective coverage for the unpleasant odor.
- the perfume compositions comprising the present invention provide pleasing odors which can be characterized as burnt caramel, opopanax, Cassia absolute, Genet absolute, Tuberose absolute and butterscotch.
- dioxohexanoate is valuable for use in perfumery, especially since the compound can also be blended with other fragrances to obtain perfume compositions which have widely varying odor characteristics.
- an olfactory effective amount of ethyl 2,4- dioxohexanoate can be incorporated into any of several perfume bases to produce perfume compositions such as cosmetics, soaps, lotions, aerosols, creams, powders and the like.
- perfume bases comprehends materials into which the fragrant ethyl 2,4-dioxohexanoate compound is added; and the term I olfactory effective amount denotes that amount of ethyl 2,4-dioxohexanoate which is added to a perfume base to produce a perfume composition having a pleasing fragrance.
- Suitable perfume bases include bubble bath, hair dressing, detergents, bar soaps, lotions, deodorants, sachets, cold creams and the like.
- a perfume base such as bubble bath can comprise sodium sesquicarbonate and magnesium carbonate
- deodorant dusting powder can comprise talc, hexachlorophene and magnesium carbonate
- after shave lotion can comprise denatured 95 percent ethyl alcohol, hexachlorophene and diethylene glycol, monoethyl ether.
- These or any other perfume base can then be converted to a perfume composition by the addition thereto of an olfactory effective amount of ethyl 2,4-dioxohexanoate.
- the compound which is an oily liquid at room temperature, can be incorporated into any of several perfume bases in two basic ways. Firstly, it can be added directly to a perfume base or; secondly, it can be dissolved in an alcoholic or hydro-alcoholic solution.
- the term solution comprehends colognes, extracts, toilet waters, after shave lotions and the like. Desirably the alcohol used in these solutions is denatured 95 percent ethyl alcohol wherein the denaturant is either l) diethylpthalate (e.g., for perfume extracts) or (2) brucine sulfate and tert. butyl alcohol (e.g., for colognes, toilet waters, etc.).
- Fixatives e.g., pentadecanolide, l5- hydroxypentadecanoice acid lactone
- perfumery alcohols are generally added to perfumery alcohols in order to depress the rawness of the alcohol odor and to hasten the maturing of the olfactory ingredient in solution.
- the compound can also be mixed with other olfactory ingredients to produce perfume compositions having a variety of pleasing odors.
- ethyl 2,4 dioxohexanoate can be mixed with methyl N-3,7- dirnethyl-7-hydroxyoctyliden-anthranilate, linalyl acetate asphalt, linalyl phenal acetate, benzyl acetate, etc.
- the resulting compositions can have odors like, e.g., Cassia Absolute; Tuberose Absolute and Genet Absolute.
- the resulting solution of the olfactory ingredient is aged and then chilled.
- the solution is desirably aged for at least 24 hours and chilled for about 1 2 hours in the same container which is used for preparing the solution.
- a solution of deodorant colognes should preferably be aged longer, i.e., about 10 days.
- the concentration of the olfactory ingredient varies with the particular kind of solution.
- a perfume extract can comprise an alcohol and from about 12 percent to about 25 percent of the olfactory ingredient; and a toilet water can comprise a hydro-alcoholic solution and from about 6 to about 8 percent of the compound in from about to about percent alcohol.
- a cologne can comprise up to about 5 percent of the olfactory ingredient in from about 75 to about 85 percent alcohol.
- All solutions are generally made on weightzvolume basis except cosmetic solutions (e.g., after shave lotions, deodorant colognes, etc., which are generally made on a weightzweight basis.
- cosmetic solutions e.g., after shave lotions, deodorant colognes, etc.
- the olfactory ingredient is added by weight and the solvent is added on a sufficient quantity (q.s.) basis.
- the solution is hydro-alcholic
- the alcohol is computed as a percentage of the total volume and is added by volume to the established weight of the compound.
- Incorporation of the olfactory ingredient into a perfume base is effected by manual stirring.
- Certain perfume compositions such as talc should, however, be preferably prepared with the aid of a power blender. Regardless of the blending means, sufficient mixing is necessary in order to ensure a thoroughly homogenous distribution of the olfactory ingredient into the perfume base.
- the olfactory effective amount of ethyl 2,4-dioxohexanoate is up to about 25 percent of the weight of the perfume composition.
- Excellent odorant results are obtained when the olfactory effective amount is up to about 5 percent on the same basis.
- the o1- factory amount of ethyl 2,4-dioxohexanoate is suitably about 8 percent by weight.
- a preferred embodiment utilizes about 5 percent of the olfactory ingredient.
- ethyl 2,4- dioxohexanoate is useful for blending with food products to provide compositions having a taste characterized as: apple, butterscotch, butter-nut, maple and maple-honey.
- Such flavors are of particular advantage in compositions such as confections, jams, jellies, syrups, ice cream and the like.
- Such compositions can contain, as the flavoring ingredient,ethyl 2,4-dioxohexanoate alone or in an admixture with other flavoring ingredients.
- the dioxohexanoate compound can be mixed with vanillin, solid extract Foenugreek, etc., to produce a syrup which has an imitation maple flavormg.
- an effective amount of the flavoring compound is added to a food carrier to impart a palatable flavor.
- the relative amount of the flavoring compound in the mixture can be expressed as a percentage of the finished food product. The percentage varies inter alia with the particular kind of food product, taste, etc.
- Ethyl 2,4-dioxohexanoate can be incorporated into many food carriers, e.g., ice cream, custard, ice milk,
- the flavoring compound can be used to produce other tasty food products such as table syrup, cream center candy and the like. Where the flavoring compound is utilized in a table syrup, the effective amount of the flavoring compound constitutes from about 0.1 to about 0.5 percent of the weight of the food product. Likewise, cream center candy and ice cream suitably use from about 0.5 percent of the weight of the food product. Likewise, cream center candy and ice cream suitably use from about 0.25 to about 1 percent of the flavoring compound on the same basis.
- the olfactory ingredient and flavoring compound namely, ethyl 2,4-dioxohexanoate
- ethyl 2,4-dioxohexanoate can be prepared by a Claisen condensation of 2-butanone and diethyl oxalate using a solution of sodium ethoxide in ethyl alcohol as the base.
- the ethyl alcohol is anhydrous and has a moisture content of less then 0.15 percent (by Karl Fischer determination) so as to produce good yields.
- the mixture is then cooled to a range of 0 to 5C whereupon a mixture of 72 gm of 2-butanone and 146 gm of diethyl oxalate is slowly added through the addition funnel over a 30 minute period and under a nitrogen atmosphere at 0 to 5C.
- the resulting mixture was then further cooled and agitated for 3 hours at 0 to 5C.
- V.P.C. Vapor phase chromatography (V.P.C.) analysis (C/SE 30) showed Fract. l to be the desired product plus a small amount of unreacted diethyl oxalate. Fracts. 2-4 were shown to be 97 99 percent of the desired product and were accordingly combined to give a fraction of about 98 percent pure ethyl 2,4- dioxohexanoate. Fract. 5 was shown to contain the desired product plus about 5 6 percent of unknown byproduct.
- EXAMPLE 2 Preparation of Imitation Maple Flavoring An imitation maple syrup containing the following ingredients Ingredients Amount methyl cyclopentenolene l5 g vanillin 50 g gum balsam peru 5 g alcohol 190 375 ml solid extract Foenugreek I25 g .caramel coloring 185 g ethyl 2,4-dioxohexanoate 40 g water q.s.
- Tuberose Absolute Perfume Composition A perfume composition containing the following ingredients and having a Tuberose absolute odor Ingredients Amount methyl n-nonyl acetaldehyde 70 ml gamma-nonalactone 420 ml amyl cinnamic aldehyde 280 ml Aurantiol 57-20 ml balsam tolu soluble resin 70 ml benzoin siam soluble resin 70 ml benzyl acetate 700 ml benzyl salicylate 700 ml celery seed oil 70 ml folione 70 ml ethyl 2,4-dioxohexanoate, 10% 500 ml indolene, 10% 42 ml iso eugcnol extra I54 ml methyl benzoate 350 ml methyl salicylate (syn) 364 ml methyl tuberate 28 ml vanilla soluble odo
- EXAMPLE 7 Preparation of Scented Bath Salts A scented bath salts composition is produced by incorporating ethyl 2,4-dioxohexanoate into the-following ingredients in the following manner so that the finished composition contains about percent, by weight, of the dioxohexanoate compound:
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- Food Science & Technology (AREA)
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Abstract
The present invention comprises perfume compositions containing ethyl 2,4-dioxohexanoate.
Description
United States Patent 1 Hajos et al.
[ PERFUME COMPOSITIONS CONTAINING ETHYL 2,4-DIOXOHEXANOATE [75] Inventors: Zoltan G. Hajos, Upper Montclair;
David R. Parrish, Glen Ridge, both Sept. 18, 1973 3,240,710 3/1966 Schiltz 252/106 3,240,711 3/1966 Wittwer 252/106 FOREIGN PATENTS OR APPLICATIONS 709,435 8/1941 Germany 424/311 OTHER PUBLICATIONS Chemical Abstracts" Vol. 53 (1959) 4309.
Primary Examiner-Albert T. Meyers Assistant Examiner-Frederick E. Waddell Attorney-Samuel L. Welt, Jon S. Saxe, Bernard S. Leon, William 1-1. Epstein and George M. Gould [57] ABSTRACT The present invention comprises perfume compositions containing ethyl 2,4-dioxohexanoate.
3 Claims, No Drawings PERFUME COMPOSITIONS CONTAINING ETI'IYL 2,4-DIOXOI-IEXANOATE This invention relates to ethyl 2,4-dioxohexanoate as a component of perfume and flavored compositions i.e., as an olfactory and flavoring ingredient.
In particular, the present invention comprises the discovery that ethyl 2,4-dioxohexanoate has a high odor value and desirable blending properties so as to be useful in perfume compositions. This invention also includes the discovery that ethyl 2,4-dioxohexanoate has a flavor value for use in flavored compositions.
The application of odiferous principles to commercial compositions like soaps, cosmetics, creams, powders, and lotions involves a multitude of complex problems. For example, soaps having unpleasant and sometimes offensive odors cannot be successfully marketed without counteracting such undesirable characteristics. The magnitude of this problem is especially great since soaps are an inexpensive commodity and cannot justify the use of precious odorants. Accordingly, a major consideration in the selection of an olfactory ingredient is its economical coverage over the products objectionable character.
To be useful as an olfactory ingredient, a compound must be fragrant and as pleasant as possible, yet not interfere with the purpose for which the final product is intended by significantly affecting factors like solubility, toxicity, color, etc. For example, soap incorporat-,
ing'an olfactory ingredient should desirably result in a finished product having a uniform fragrance, high odor stability and effective coverage for the unpleasant odor.
SUMMARY OF THE INVENTION DESCRIPTION OF THE PREFERRED EMBODIMENT The perfume compositions comprising the present invention provide pleasing odors which can be characterized as burnt caramel, opopanax, Cassia absolute, Genet absolute, Tuberose absolute and butterscotch.
As a compound reminiscent of such odors, ethyl 2,4-
' dioxohexanoate is valuable for use in perfumery, especially since the compound can also be blended with other fragrances to obtain perfume compositions which have widely varying odor characteristics. For example an olfactory effective amount of ethyl 2,4- dioxohexanoate can be incorporated into any of several perfume bases to produce perfume compositions such as cosmetics, soaps, lotions, aerosols, creams, powders and the like. As used herein, the term perfume bases comprehends materials into which the fragrant ethyl 2,4-dioxohexanoate compound is added; and the term I olfactory effective amount denotes that amount of ethyl 2,4-dioxohexanoate which is added to a perfume base to produce a perfume composition having a pleasing fragrance.
Suitable perfume bases include bubble bath, hair dressing, detergents, bar soaps, lotions, deodorants, sachets, cold creams and the like. Of course, the chemical composition of each perfume base varies. For example, a perfume base such as bubble bath can comprise sodium sesquicarbonate and magnesium carbonate; deodorant dusting powder can comprise talc, hexachlorophene and magnesium carbonate, and after shave lotion can comprise denatured 95 percent ethyl alcohol, hexachlorophene and diethylene glycol, monoethyl ether. These or any other perfume base can then be converted to a perfume composition by the addition thereto of an olfactory effective amount of ethyl 2,4-dioxohexanoate.
The compound, which is an oily liquid at room temperature, can be incorporated into any of several perfume bases in two basic ways. Firstly, it can be added directly to a perfume base or; secondly, it can be dissolved in an alcoholic or hydro-alcoholic solution. As used herein, the term solution comprehends colognes, extracts, toilet waters, after shave lotions and the like. Desirably the alcohol used in these solutions is denatured 95 percent ethyl alcohol wherein the denaturant is either l) diethylpthalate (e.g., for perfume extracts) or (2) brucine sulfate and tert. butyl alcohol (e.g., for colognes, toilet waters, etc.). The alcohols used are of two types with a fixative and without a fixative. Fixatives (e.g., pentadecanolide, l5- hydroxypentadecanoice acid lactone) are generally added to perfumery alcohols in order to depress the rawness of the alcohol odor and to hasten the maturing of the olfactory ingredient in solution.
The compound can also be mixed with other olfactory ingredients to produce perfume compositions having a variety of pleasing odors. For example, ethyl 2,4 dioxohexanoate can be mixed with methyl N-3,7- dirnethyl-7-hydroxyoctyliden-anthranilate, linalyl acetate coeur, linalyl phenal acetate, benzyl acetate, etc. Where mixed with other olfactory ingredients, the resulting compositions can have odors like, e.g., Cassia Absolute; Tuberose Absolute and Genet Absolute.
Irrespective of whether the alcohol is fixed, the resulting solution of the olfactory ingredient is aged and then chilled. The solution is desirably aged for at least 24 hours and chilled for about 1 2 hours in the same container which is used for preparing the solution. A solution of deodorant colognes should preferably be aged longer, i.e., about 10 days.
The concentration of the olfactory ingredient, namely, ethyl 2,4-dioxohexanoate, varies with the particular kind of solution. For example, a perfume extract can comprise an alcohol and from about 12 percent to about 25 percent of the olfactory ingredient; and a toilet water can comprise a hydro-alcoholic solution and from about 6 to about 8 percent of the compound in from about to about percent alcohol. Similarly, a cologne can comprise up to about 5 percent of the olfactory ingredient in from about 75 to about 85 percent alcohol.
All solutions are generally made on weightzvolume basis except cosmetic solutions (e.g., after shave lotions, deodorant colognes, etc., which are generally made on a weightzweight basis. In the former case the olfactory ingredient is added by weight and the solvent is added on a sufficient quantity (q.s.) basis. Where the solution is hydro-alcholic, the alcohol is computed as a percentage of the total volume and is added by volume to the established weight of the compound.
Incorporation of the olfactory ingredient into a perfume base is effected by manual stirring. Certain perfume compositions such as talc should, however, be preferably prepared with the aid of a power blender. Regardless of the blending means, sufficient mixing is necessary in order to ensure a thoroughly homogenous distribution of the olfactory ingredient into the perfume base.
Good odorant results are obtained when the olfactory effective amount of ethyl 2,4-dioxohexanoate is up to about 25 percent of the weight of the perfume composition. Excellent odorant results are obtained when the olfactory effective amount is up to about 5 percent on the same basis. For example, in bubble bath, the o1- factory amount of ethyl 2,4-dioxohexanoate is suitably about 8 percent by weight. A preferred embodiment utilizes about 5 percent of the olfactory ingredient.
Where used as a flavoring ingredient, ethyl 2,4- dioxohexanoate is useful for blending with food products to provide compositions having a taste characterized as: apple, butterscotch, butter-nut, maple and maple-honey. Such flavors are of particular advantage in compositions such as confections, jams, jellies, syrups, ice cream and the like. Such compositions can contain, as the flavoring ingredient,ethyl 2,4-dioxohexanoate alone or in an admixture with other flavoring ingredients. For example, the dioxohexanoate compound can be mixed with vanillin, solid extract Foenugreek, etc., to produce a syrup which has an imitation maple flavormg.
In using ethyl 2,4-dioxohexanoate as a synthetic flavoring, an effective amount of the flavoring compound is added to a food carrier to impart a palatable flavor. The relative amount of the flavoring compound in the mixture (flavoring compound-i-food carrier) can be expressed as a percentage of the finished food product. The percentage varies inter alia with the particular kind of food product, taste, etc.
Ethyl 2,4-dioxohexanoate can be incorporated into many food carriers, e.g., ice cream, custard, ice milk,
water ices, candy, flavor bases, cake mixes, icings, fill ings, and the like.
1 Food palatable results are obtained when the effective amount of the flavoring compound constitutes up to about 5 percent of the weight of the food product. Excellent palatable results are obtained when the effective amount of the flavoring compound constitutes up to about 1 percent on the same basis As noted, the flavoring compound can be used to produce other tasty food products such as table syrup, cream center candy and the like. Where the flavoring compound is utilized in a table syrup, the effective amount of the flavoring compound constitutes from about 0.1 to about 0.5 percent of the weight of the food product. Likewise, cream center candy and ice cream suitably use from about 0.5 percent of the weight of the food product. Likewise, cream center candy and ice cream suitably use from about 0.25 to about 1 percent of the flavoring compound on the same basis.
The olfactory ingredient and flavoring compound, namely, ethyl 2,4-dioxohexanoate, can be prepared by a Claisen condensation of 2-butanone and diethyl oxalate using a solution of sodium ethoxide in ethyl alcohol as the base. Preferably, the ethyl alcohol is anhydrous and has a moisture content of less then 0.15 percent (by Karl Fischer determination) so as to produce good yields.
Ethyl 2,4-dioxohexanoate has already been described in the literature, for example, in 1906 by Otto Diels in Chem.Berichte 39, 1333. However, despite the fact that ethyl 2,4-dioxohexanoate has been known for over half a century, no one until now has recognized the unique olfactory and flavoring properties of this compound. It was accordingly most surprising to find that the fragrance of ethyl 2,4-dioxohexanoate provides not only a desirable perfume odor, but also that the compound possesses the aforementioned desirable flavoring properties.
In order to illustrate our invention the following examples are given each of which utilizes ethyl 2,4- dioxohexanoate.
Purity (V.P.C. analysis) Empirical formula percent=9 l 98 a 12 4 EXAMPLE 1 Preparation of ethyl 2,4-dioxohexanoate 236 gm of anhydrous ethyl alcohol is distilled directly into a 1,000 ml three-necked flask equipped with a fast agitator, water-cooled condenser, addition funnel, thermometer and gas-inlet/outlet tube. The reaction is conducted under a nitrogen atmosphere. Anhydrous sodium ethoxide (68 gm) is added with agitation and the mixture refluxed for 1 hour. The mixture is then cooled to a range of 0 to 5C whereupon a mixture of 72 gm of 2-butanone and 146 gm of diethyl oxalate is slowly added through the addition funnel over a 30 minute period and under a nitrogen atmosphere at 0 to 5C. The resulting mixture was then further cooled and agitated for 3 hours at 0 to 5C.
After cooling to 0C, 168 ml of a 1:1 hydrochloric acid/H O (6M) solution was added and the temperature of the resultant solution was maintained below 10C. The acidified solution was extracted twice, each time with 300 ml of toluene. The organic phase was then successively washed twice with 600 ml water, once with 600 ml of a 10 percent Na CO solution and once with 400 ml of a saturated sodium chloride solution. The toluene layers were then separated from the aqueous layers, combined, dried over magnesium sulfate and filtered. The toluene was removed by distillation under 25 mm/Hg pressure yielding ethyl 2,4-
dioxohexanoate. Purity (V.P.C.) about 91 percent. Optional and further purification was effected by fractional distillation through a 6 inch glass Helix packed column at 0.2 mm/Hg. Distillation yielded:
Fract. Vapor Pot. Pressure l. -85C 958-104C 2.0 mm 2. C 104C 2.0 mm 3. 86C 112C 2.0 mm 4. 89C 122C 2.0 mm 5. 85C 165C 2.0 mm
Vapor phase chromatography (V.P.C.) analysis (C/SE 30) showed Fract. l to be the desired product plus a small amount of unreacted diethyl oxalate. Fracts. 2-4 were shown to be 97 99 percent of the desired product and were accordingly combined to give a fraction of about 98 percent pure ethyl 2,4- dioxohexanoate. Fract. 5 was shown to contain the desired product plus about 5 6 percent of unknown byproduct.
EXAMPLE 2 Preparation of Imitation Maple Flavoring An imitation maple syrup containing the following ingredients Ingredients Amount methyl cyclopentenolene l5 g vanillin 50 g gum balsam peru 5 g alcohol 190 375 ml solid extract Foenugreek I25 g .caramel coloring 185 g ethyl 2,4-dioxohexanoate 40 g water q.s.
L000 ml was prepared by:
l. combining the first seven ingredients above, and 2. bringing the solution up to a final volume of 1,000 ml. with water (q.s.).
EXAMPLE 3 Preparation of Cassia Absolute Perfume Composition A perfume composition containing the following ingredients and having a Cassia absolute odor Ingredients Amount n-nonyl aldehyde 560 ml methyl n-nonyl acetaldehyde 392 ml anisic aldehyde 280 ml anisyl aldehyde 280 ml benzyl alcohol (P.G.)" 2240 ml citronellol extra I68 ml cuminic aldehyde 56 ml dipropylene glycol I48 ml methyl Z-octynoate 560 ml geraniol 560 ml geranyl butyrate 392 ml ethyl 2,4-dioxohexanoate 500 ml benzopyrrole(indol) l0% in triethanolaminc 280 ml 2-nonenal pure 1% 112 ml beta-iononc 560 ml hydroxycitronellal l I20 ml linalool coeur 280 ml methyl salicylate(syn) 560 ml p-methyl acetophenone, 10% H2 ml styrax soluble resin 560 ml terpineol extra 280 ml P.G. perfume grade was prepared (10,000 ml) by:
l. combining the ingredients in the order as above listed, and
2. adequately mixing each ingredient into the resulting mixture in order to ensure a homogenous dispersion of each ingredient.
EXAMPLE 4 Preparation of Tuberose Absolute Perfume Composition A perfume composition containing the following ingredients and having a Tuberose absolute odor Ingredients Amount methyl n-nonyl acetaldehyde 70 ml gamma-nonalactone 420 ml amyl cinnamic aldehyde 280 ml Aurantiol 57-20 ml balsam tolu soluble resin 70 ml benzoin siam soluble resin 70 ml benzyl acetate 700 ml benzyl salicylate 700 ml celery seed oil 70 ml folione 70 ml ethyl 2,4-dioxohexanoate, 10% 500 ml indolene, 10% 42 ml iso eugcnol extra I54 ml methyl benzoate 350 ml methyl salicylate (syn) 364 ml methyl tuberate 28 ml vanilla soluble odo resin 42 ml Ylang bourbon extra 350 ml Methyl N-3,7-dimethyl-7-hydroxyoctyliden-anthranilate was prepared (10,000 ml) by:
l. combining the ingredients in the order as above listed, and
2. adequately mixing each ingredient into the resulting mixture in order to ensure a homogenous dispersion of each ingredient.
EXAMPLE 5 Preparation of Genet Absolute Perfume Composition A perfume composition containing the following ingredients and having a Genet absolute odor Ingredients Amount benzo pyrone (coumarin) extra 16 ml oranger crystals ethyl B-napthyl I 1 ml ketone lauryl acetate I ml n-nonyl aldehyde, l0% in I 1 ml dipropylene glycol n-decyl aldehyde l l ml n-decyl alcohol 3 ml Anisic Aldehyde 5 ml Aurantiol 50 3 ml Benzyl Alcohol R0. 415 ml Constituant I5 29 ml P-cuminic aldehyde, l0% in 5 ml dipropylene glycol ethyl phenyl acetate 5 ml ethyl propionate 5 ml folione l% in dipropylene glycol 5 ml geraniol 3 ml ethyl 2,4-dioxohexanoate I0 ml indol 10 ml iso eugenol 52 ml Labdanum soluble resin 52 ml Iaurine extra 52 ml linalyl acetate coeur 6 ml linalyl phenyl acetate 52 ml methyl aceto phenone 10 ml Peru balsam soluble resin 124 ml phenyl ethyl alcohol extra 2l ml vetivert (El) 83 ml Perfume grade was prepared (1,000 ml) by:
l. combining the ingredients in the order as above listed, and
2. adequately mixing each ingredient into the resulting mixture in order to ensure a homogenous dispersion of each ingredient.
EXAMPLE 6 Preparation of Scented Bar Soap A scented bar soap composition is produced by incorporating the perfume composition prepared in Example 5 into soap chips in the following manner so that the finished product contains about I percent, by weight, of said perfume composition:
I. weigh soap chips and transfer into mixing container (percent of perfume composition is based on total weight of chips used),
2. weigh perfume composition and premix with a small amount of soap chips,
3. combine premix with chips in container and mix until homogeneous,
4. pass chips through a worm-screw driver,
5. place ground chips into a die press and compress to a pressure of about 6,000 PSI, and
6. remove compressed cake and 'cut into quarters.
EXAMPLE 7 Preparation of Scented Bath Salts A scented bath salts composition is produced by incorporating ethyl 2,4-dioxohexanoate into the-following ingredients in the following manner so that the finished composition contains about percent, by weight, of the dioxohexanoate compound:
Ingredients Amount sodium sesquicarbonate 90 magnesium carbonate 5 ethyl 2,4-dioxohexanoate 5 was prepared by:
1. grinding the ethyl 2,4-dioxohexanoate into the magnesium carbonate in a milling apparatus,
2. adding the perfumed magnesium carbonate to the position is a bath salt.
Claims (2)
- 2. The method of claim 1 wherein the said cosmetic composition is a perfume containing a mixture of different perfume ingredients other than ethyl 2,4-dioxohexanoate.
- 3. The method of claim 1 wherein said cosmetic composition is a bath salt.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US413470A | 1970-01-19 | 1970-01-19 | |
US350662A US3860727A (en) | 1970-01-19 | 1973-04-12 | Perfume and flavored compositions containing ethyl 2,4-dioxohexanoate |
Publications (1)
Publication Number | Publication Date |
---|---|
US3760087A true US3760087A (en) | 1973-09-18 |
Family
ID=26672661
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00004134A Expired - Lifetime US3760087A (en) | 1970-01-19 | 1970-01-19 | Perfume compositions containing ethyl 2,4-dioxohexanoate |
US350662A Expired - Lifetime US3860727A (en) | 1970-01-19 | 1973-04-12 | Perfume and flavored compositions containing ethyl 2,4-dioxohexanoate |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US350662A Expired - Lifetime US3860727A (en) | 1970-01-19 | 1973-04-12 | Perfume and flavored compositions containing ethyl 2,4-dioxohexanoate |
Country Status (7)
Country | Link |
---|---|
US (2) | US3760087A (en) |
BE (1) | BE761684A (en) |
CH (1) | CH539681A (en) |
DE (1) | DE2101908A1 (en) |
FR (1) | FR2077214B1 (en) |
GB (1) | GB1315587A (en) |
NL (1) | NL7100578A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4126585A (en) * | 1976-06-11 | 1978-11-21 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | 2-Methyl-2-ethyl-hexanoate ester perfume compositions |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE709435C (en) * | ||||
US3098789A (en) * | 1960-03-29 | 1963-07-23 | Socony Mobil Oil Co Inc | Agricultural spray emulsion concentrates and their method of manufacture |
US3240711A (en) * | 1958-10-08 | 1966-03-15 | Wittwer John | Germicidal detergent bar |
US3240710A (en) * | 1962-06-15 | 1966-03-15 | Swift & Co | Lauryl pyridinium salt of 5-chloro-2-mercaptobenzothiazole and tri- and dibrominatedsalicylanilides bactericide composition |
-
1970
- 1970-01-19 US US00004134A patent/US3760087A/en not_active Expired - Lifetime
-
1971
- 1971-01-14 CH CH54971A patent/CH539681A/en not_active IP Right Cessation
- 1971-01-15 NL NL7100578A patent/NL7100578A/xx unknown
- 1971-01-15 DE DE19712101908 patent/DE2101908A1/en active Pending
- 1971-01-18 FR FR7101507A patent/FR2077214B1/fr not_active Expired
- 1971-01-18 BE BE761684A patent/BE761684A/en unknown
- 1971-01-19 GB GB257071A patent/GB1315587A/en not_active Expired
-
1973
- 1973-04-12 US US350662A patent/US3860727A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE709435C (en) * | ||||
US3240711A (en) * | 1958-10-08 | 1966-03-15 | Wittwer John | Germicidal detergent bar |
US3098789A (en) * | 1960-03-29 | 1963-07-23 | Socony Mobil Oil Co Inc | Agricultural spray emulsion concentrates and their method of manufacture |
US3240710A (en) * | 1962-06-15 | 1966-03-15 | Swift & Co | Lauryl pyridinium salt of 5-chloro-2-mercaptobenzothiazole and tri- and dibrominatedsalicylanilides bactericide composition |
Non-Patent Citations (1)
Title |
---|
Chemical Abstracts Vol. 53 (1959) 4309. * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4126585A (en) * | 1976-06-11 | 1978-11-21 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | 2-Methyl-2-ethyl-hexanoate ester perfume compositions |
Also Published As
Publication number | Publication date |
---|---|
US3860727A (en) | 1975-01-14 |
BE761684A (en) | 1971-07-19 |
NL7100578A (en) | 1971-07-21 |
CH539681A (en) | 1973-09-14 |
GB1315587A (en) | 1973-05-02 |
FR2077214A1 (en) | 1971-10-22 |
FR2077214B1 (en) | 1974-08-19 |
DE2101908A1 (en) | 1971-07-29 |
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