Perfumed compositions include, as an odorant therefor, an olfactory affecting amount of N,N-diethyl-2-ethylhexanamide.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
The present invention relates to novel perfume compositions, including 
novel perfume bases, and, more especially, to such perfume compositions 
comprised of the odorant, N,N-diethyl-2-ethylhexanamide. 
2. Description of the Prior Art 
The use of certain alkanoic acid amides for incorporation into perfume or 
insect repellent compositions has already been proposed to this art, but 
not one of such amides is either distinguished or characterized by any 
unique or original fragrance evoking a pleasant olfactory response. Thus, 
Einhorn et al, Ber., 39, 1,223 (1906) report that 
N,N-diethyl-2-ethylbutanamide evolves a faint scent akin to that of 
menthol; French Pat. No. 1,572,332 notes that 
N,N-diethyldimethylpropanamide has a peppermint fragrance, while 
N,N-dimethyl-2-ethylbutanamide emits the fragrance of natural mint. In 
U.S. Pat. No. 3,909,462 there is attributed to 
N-phenyl-N-methyl-2-ethylbutanamide the odor of grapefruit, utilized in 
the formulation of food and herb aromas to develop a composition suitable 
for use as a base in perfumes having a lavender fragrance. Finally, A. S. 
Lutta et al, Entomol. Obozrenie, 45, 317-25 (1966) noted in a study of the 
insect repellent properties of the alkanamides, the agreeable odor of 
N,N-diethyloctamide, without reflecting upon any specific fragrance. It 
has since been determined that this particular amide has a weakly spicy 
odor that is relatively common. It too has been definitely ascertained 
that the amides of the C.sub.5 -C.sub.6 alkanoic acids, with the exception 
of N-phenyl-N-methyl-2-ethylbutanamide, emit the more or less common mint 
odors. Furthermore, for a given acid, the character of the fragrance 
varies in direct response to the nature of the substituents borne by the 
amido nitrogen atom, but without, however, the ultimate fragrance evolved 
being predictable; thus, N,N-dimethyl-2-ethylbutanamide emits the fresh 
scent of natural mint, far stronger than that of the N,N-diethyl homolog, 
the scent of which latter derivative, even though also being that of mint, 
being much weaker and more akin to that of peppermint. On the other hand, 
the molecular structure of the acid significantly affects the fragrance of 
the amide; thus, N,N-diethylcaprylamide evolves a scent considerably 
different from that of N,N-diethyl-2-ethylbutanamide. It logically 
follows, therefore, that it is difficult, if not impossible for those 
skilled in this art to reliably predict whether or not a given alkanamide 
will have a pleasing odor from an olfactory sensation point of view and, 
if so, just what that particular fragrance would be. 
Accordingly, the perfume industry is continuously seeking novel odorants 
and fragrances which by virtue of their uniqueness, availability and 
strength of scent are well adapted for formulation into perfume 
compositions which are completely unique. 
SUMMARY OF THE INVENTION 
Accordingly, a major object of the present invention is the provision of a 
novel odorant, and perfume compositions/formulations comprised thereof, 
all of which are characterized by an originally unique fragrance. 
Briefly, the present invention features novel perfume 
compositions/formulations, whether perfume bases or final perfume 
products, each of which is characterized in that, in addition to the 
typical perfume ingredients or components comprising same, such products 
contain an effective fragrant, or fragrance attentuating amount of the 
odorant, N,N-diethyl-2-ethylhexanamide. 
DETAILED DESCRIPTION OF THE INVENTION 
More particularly, the present invention features perfume 
compositions/formulations, and perfume bases and perfumed products, each 
of which is characterized by including, as the active ingredient odorant 
thereof, an effective olfactory affecting amount of 
N,N-diethyl-2-ethylhexanamide [DEH]. 
N,N-diethyl-2-ethylhexanamide, which has the structural formula: 
##STR1## 
emits or gives off an original perfume fragrance combining the scents of a 
thorny rose, galbulus of eucalyptus having a slightly peppery jasmine 
fragrance. The powerful, diffusive and abundant nature of the subject 
odorant is atypically unique and, thus, such novel odorant is well adapted 
for per se use as a novel perfume, or for formulation into perfume 
compositions comprising DEH as either the sole odorant, or the DEH in 
combination with at least one other fragrance. 
By the expression "perfume composition" or "formulation" any admixture of 
the different perfume ingredients, such as the typical solvents, solid or 
liquid perfume carriers, fixing agents, any one or more of the known 
fragrances or scents, and the like, and with which the 
N,N-diethyl-2-ethylhexanamide is formulated or incorporated, such 
admixtures being utilized to impart to any type of substrate, or finished 
or final product, the particular fragrance desired. The perfume bases 
constitute preferred examples of the perfume compositions consistent 
herewith wherein the N,N-diethyl-2-ethylhexanamide may be used to 
advantage. Other compositions wherein the DEH may advantageously be 
incorporated are the conventional detergent compositions. These 
compositions typically comprise one or more of the following ingredients: 
anionic, cationic or amphoteric surface active agents, bleaching agents, 
optical bluing or whitening agents, various fillers and anti-redeposition 
ingredients. The nature of these different ingredients is not critical and 
the N,N-diethyl-2-ethylhexanamide may be added to any type of detergent. 
Toilet waters, after shave lotions, perfumes, soaps and deodorant and 
sanitary products, for example in aerosol form, are exemplary of those 
substrates and final products which can be uniquely scented with 
N,N-diethyl-2-ethylhexanamide according to this invention. 
N,N-diethyl-2-ethylhexanamide is itself a colorless liquid, boiling a 
87.degree. C. under a pressure of 1.5 mm Hg, and is very soluble in the 
conventional organic solvents, such as the alcohols, ketones, esters or 
ethers. 
The amount of DEH in the various compositions according to the invention, 
expressed in percentages by weight in the particular composition under 
consideration, strictly depends on the nature of each such composition 
(perfume or toilet base, for example) and the intensity of the fragrance 
desired in the final product. It is thus obvious that in a perfume base 
the amount of N,N-diethyl-2-ethylhexanamide may be very high, for example, 
higher than 50% by weight, and as much as 90% by weight, while in a 
perfume, a toilet water, an after shave lotion or a soap, such amount may 
be considerably lower than 50% by weight. Thus, for all practical purposes 
the lower limit on the amount of N,N-diethyl-2-ethylhexanamide is that 
amount which effects a perceptible modification in the odor, fragrance, or 
scent of the final product. In certain cases, this minimum amount may be 
on the order of 0.01% by weight. Obviously, contents without the 
aforenoted range too may be utilized without departing from the scope of 
the present invention. 
Moreover, the DEH incorporated per the invention is itself conveniently 
prepared by simply reacting a 2-ethylhexanoyl halide with diethylamine in 
the presence of an aqueous solution of an alkali metal base (preferably 
sodium or potassium).

In order to further illustrate the present invention and the advantage 
thereof. The following specific examples are given, it being understood 
that same are intended only as illustrative and in nowise limitative. 
EXAMPLE 1 
A perfume base having a floral scent was formulated from the following 
ingredients: 
______________________________________ 
(i) .alpha.-Hexylcinnamaldehyde; 
20 g 
(ii) Benzyl acetate; 5 g 
(iii) 4-Nonanolide; 0.5 g 
(iv) Pure rose oil; 10 g 
(v) Tonquin musk, 3% by weight in 
ethanol; and 2 g 
(vi) N,N-Diethyl-2-ethylhexanamide [DEH] 
62.5 g 
______________________________________ 
The DEH inparted to this floral fragrence the fine flowery scent of rose by 
aiding in the emitting of the volatile pure rose oil and by imbuing the 
jasmine scent with a strikingly natural aroma. 
EXAMPLE 2 
A peppermint base was formulated from the following ingredients: 
______________________________________ 
(i) Eugenol; 10 g 
(ii) Isoeugenol; 10 g 
(iii) Methyl dihydrojasmonate; 
5 g 
(iv) Essential oil of black pepper; 
5 g 
(v) Isobornylcyclohexanol; and 
10 g 
(vi) DEH 60 g 
______________________________________ 
In the foregoing composition, the DEH enhanced the apparent concentration 
of the pepper scent and added thereto a scent of galbulus of eucalyptus 
and of pepperly rosebud. 
EXAMPLE 3 
A lilac base was formulated from the following ingredients: 
______________________________________ 
(i) Terpineol; 20 g 
(ii) Linalol; 5 g 
(iii) Benzyl acetate; 10 g 
(iv) Linalyl acetate; 5 g 
(v) .beta.-Phenylethyl alcohol; 
10 g 
(vi) 60 -Hexylcinnamaldehyde; 
5 g 
(vii) Essential oil of Styrax; 
10 g 
(viii) Anisaldehyde diethyl acetal; and 
10 g 
(ix) DEH 25 g 
______________________________________ 
The DEH imparted to this formulation an exceptional lilac bouquet combined 
with the natural freshness of its floral scent, the strong and penetrating 
scent of eucalyptus, and the rosy scent of lilac. 
EXAMPLE 4 
150 g of N,N-diethyl-2-ethylhexanamide were added to a lemon based washing 
powder comprised of the following ingredients: 
______________________________________ 
(i) Essence of peel of mandarin orange; 
30 g 
(ii) Essence of grapefruit; 
50 g 
(iii) Essence of cypress; 10 g 
(iv) Essence of Florida orange; 
120 g 
(v) Essence of lemon peel; 
80 g 
(vi) Essence of Java citronella; 
30 g 
(vii) d-Limonene; 260 g 
(viii) Isobornylcyclohexanol 
50 g 
(ix) Para-tertbutylcyclohexyl acetate; 
10 g 
(x) Isocyclocitral 5 g 
(xi) Citral; 95 g 
(xii) diPhenyl oxide; 30 g 
(xiii) Hexylcinnamaldehyde; 
35 g 
(xiv) C.sub.10 aldehyde; and 
15 g 
(xv) Terpene oils of geranium 
30 g 
850 g 
______________________________________ 
The DEH formulation was then compared to the lemon scented base, per se, 
and it was determined that incorporation of the 
N,N-diethyl-2-ethylhexanamide attenuated the artificial nature of the base 
powder and imparted to the composition the natural scent of ripe lemon 
peels. 
COMATIVE EXAMPLE A 
In each of the compositions described in the foregoing Examples 1 to 3, the 
DEH was replaced with dipropylene glycol which functioned as a neutral 
solvent. In each case, such replacement resulted in the complete loss of 
those characteristics noted as being imparted upon the respective 
compositions by the DEH. 
COMATIVE EXAMPLE B 
In each of the compositions described in the foregoing Examples 1 to 3, the 
DEH was replaced by one of the following amides: 
(i) N,N-diethyl-2-ethylbutanamide; 
(ii) N,N-diethyl-2,2-dimethylpropanamide; 
(iii) N,N-dimethyl-2-ethylbutanamide; 
(iv) N-phenyl-N-methyl-2-ethylbutanamide; and 
(v) N,N-diethylcaprylamide. 
In each case, the fragrance imparted to the respective composition by DEH 
had totally disappeared, and the more common mint or camphor scents 
appeared in its stead. 
The DEH utilized in the preceding examples was a colorless liquid, having a 
boiling point of 87.degree. C. under a pressure of 1.5 mm Hg; its density 
at 20.degree. C. was 0.869 and its index of refraction was 1.447. Such 
compound was prepared in the following manner: 
Into a stainless steel reactor having a capacity of 3.81 and equipped with 
means for mechanical agitation, an internal thermometer, a 1 liter 
discharge ampoule and water cooling means, 892 g water were charged. The 
agitator was actuated and over the course of 40 minutes, 824 g 
diethylamine were added, while maintaining the temperature under 
20.degree. C. Subsequently, 824 g 2-ethylhexanoyl chloride were added 
thereto, over a period of 3 hours. The agitation was continued for 2 more 
hours at a temperature of less than 20.degree. C., followed by the 
separation of the organic layer, which was washed, first with 300 ml of a 
10% aqueous solution of sodium hydroxide, and then with 200 ml of a 5% by 
weight aqueous solution of sodium hydroxide. The organic layer was then 
distilled. A product was obtained, which was treated with active carbon 
under a nitrogen blanket. After filtration, 1,033 g of a product having 
the aforenoted characteristics was obtained, the elemental analysis and 
infra red spectrum thereof being that of a compound having the structural 
formula: 
##STR2## 
While the invention has been described in terms of various preferred 
embodiments, the skilled artisan will appreciate that various 
modifications, substitutions, omissions, and changes may be made without 
departing from the spirit thereof. Accordingly, it is intended that the 
scope of the present invention be limited solely by the scope of the 
following claims.