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Publication numberUS3884841 A
Publication typeGrant
Publication dateMay 20, 1975
Filing dateMar 29, 1974
Priority dateApr 18, 1973
Also published asDE2415922A1, DE2415922B2, DE2415922C3
Publication numberUS 3884841 A, US 3884841A, US-A-3884841, US3884841 A, US3884841A
InventorsDavid Derijke, Jan Th M F Maessen
Original AssigneeNaarden International Nv
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
2-n-butyl 4,4,6-trimethyl-1,3 dioxane perfume
US 3884841 A
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Description  (OCR text may contain errors)

United States Patent Maessen et al.

[ 51 May 20, 1975 2-N-BUTYL 4,4,6-TRIMETHYL-l,3 DlOXANE PERFUME lnventors: Jan Th. M. F. Maessen; David DeRijke, both of Naarden, Netherlands Naarden International, N.V., Naarden-Bussum, Netherlands Filed: Mar. 29, 1974 Appl. No.: 456,317

Assignee:

Foreign Application Priority Data Apr. 18, 1973 Netherlands 7305487 U.S. Cl. 252/522 Int. Cl Cllb 7/00 Field of Search 252/5 22 [56] References Cited FOREIGN PATENTS OR APPLICATIONS 981,285 l/l965 United Kingdom 252/522 Primary Examiner-Veronica OKeefe Attorney, Agent, or Firm-Stevens, Davis, Miller & Mosher [57] ABSTRACT 1 Claim, 2 Drawing Figures 1 Z-n-BUTYL 4,4,6-TRIMETHYL-1,3 DIOXANE PERFUME 2-n-butyl-4.4.6-trimethyl*l.3-dioxane is the cyclic acetal derived from n-pentanal and 2-methylpentanediol-2.4. According to the literature (S.Arctander, Perq fume and Flavor Chemicals, Montelair, 1969) the following cyclic acetals of the general formula 2 are known as possible perfume of this diol:

v 2 able for perfume compositions for cleaning agents, because the flavour has no granium-rose note:

It is clear that the abovementioned patent gives no positive expectation as to the perfume properties of 1.3-dioxanes having geminal methyl groups. In spite of that the applicants have prepared a series of pompounds of the general formula 2 and have them judged as to flavour and other usefulness in perfume composi R Description the flavour I Literature CH CH=CH- Floral green, almost herbaceous Arctander,

green, odor possibly to be used Monograph in perfume compositions as a 745.

modifier in modern. floral fragrance types of perfume Sweet-green, warm-earthy odor, id. CH2 reseda. To be used in combinat- Monograph ion with Oak-moss, Vetiver, 2485 Lavender and Rose materials warm floral with a fruity id. 2 2 note. As a fixative in Monogr'ph fruity-floral bases 2582.

such as Jasmin.

In addition to these descriptions in the literature (British Pat. No. 981,285) the following compounds of the general formula 2 are indicated, as being not suittions and perfumed articles by a panel of experienced perfumers. Their judgement has been summarized in the following table;

Description of the flavour Green, "floral, peppermintlike,

not interesting,

Green, herbaceous, fruity, not interesting.

soup-ggree'rslike not usuable Lavender, mint, bayleaflike, very interesting.

fatty, not int ere sting.

weak, little characteristic, not interesting.

weak, metallic, unuseful' Continued No. R Description of the flavour ..l.:- T i Y I p 8 li-- very weak rosellke, not useful.

-CH -OH weak, spicy, not lnterestlng The compounds 3 and 9 from the above tabel were Continued known already from the cited literature (S.Arctander) Camphor Chinese 2130 parts Ey wei l: as possibly interesting, but they appear not to be able figmjj i 508 5:2: by ifiifihi to stand the explicit evaluation by experienced perfu- Cedarwood oil Virginia 40 parts by weight mors. Surprisingly it appears, however, that compound 2121 5 522: ii; No.4,2-n-butyl-4,4.6-trimethyl-1.3-dioxane, in spite of 20 Liguvert" parts by weight the negative expectation aroused by the British patent Methylnonylfacemldehyde 3 Pans by welght Opoponax oil 1 parts by weight cited, to possess very attractive perfume properties. Tetrahydmlinalool 2 pans by weight Applied in perfume compositions 2-n-butyl-4.4.6- Cistus Oil 2 Parts y wqght Laurel noble oil 2 parts by weight trimethyl-l.3-dioxane gives a fresh, vegetable note to Myrrhe oil 2 pans by weight it. Dependent on the type of composition the dosage 25 2j:n-Butyl-4.4.6-trimethyl-l.3- 160 parts by weight loxane may he between about 5 and about 15% by weight. As mgthylpmhalme 103 parts by weight a matter of fact in a perfumed product the final concen- 1000 Pans by weight tration will lie much lower.

2-n-Butyl-4.4.6-trimethyl-1.3-dioxane may be prepared in the following way:

Into an 1 liter reaction receiver, provided with a agitator, Vigreux head having a tray trap and thermometer, are brought:

118 g (1 mol) of 2-methyl pentane diol-2.4.

86 g (1 mol) n-pentanal and 250 g of methylene chloride.

0,05 g p-toluene sulfonic acid is then added at about C under stirring. Subsequently in about 3 hours 18 g of water are removed by azeotropic distillation at a flask temperature of 57C. The contents of the flask are cooled and, after transfer into a separating funnel, washed with 100 g soda solution (5%) and thereafter with 100 g of water. Thereafter the organic solution is distilled under decreased pressure mm Hg) to a bottom temperature of 70C. There are obtained:

200 g of methylene chloride back and 180 g of evaporation residue.

The evaporation residue is fractionated in a distillation apparatus with a 40 cm Vigreus-head, at which is obtained: 4 g fore-runnings, boiling point up to 81C/l mm Hg and 170 g 2-n-butyl-4.4 .6-trimethyl-l .3- dioxane boiling point 8l-82C/1 mm Hg; u 1,4295.

The invention can be illustrated with the following examples:

Absolue Mousse de Chene Coumarine Musk R l Olibanum-resinoid 5 parts by weight 5 parts by weight 10 parts by weight 40 parts by weight (Liguvert a perfume base of Naarden lntemational) EXAMPLE II Perfume composition Lavender-Fougere for soap.

Absolue Labdanum dEspagne 5 Galbanum resinoid 5 parts by weight Coumarine l5 parts by weight Perpetual crist. 25 parts by weight Absolue Mousse de Chefie 20 parts by we ght- Hexylbenzoate 50 parts by we ght Benzylsalicylate 50 parts by weight Lavender oil 230 parts by weight Bergamot oil 150 parts by weight Petitgrain oil parts by weight Rosemary oil Spanish 50 parts by weight Geranium oil 50 parts by weight Vetiveryl acetate 50 parts by weight Patchouli oil 40 parts by weight Lavandin concrete 15 parts by weight Tetrahydrolinalool 10 parts by weight Eugenol 5 parts by weight 2-n-butyl-4.4.6-trimethyl-l.3- parts by weight dioxane 1000 parts by weight parts by weight The perfume compositions prepared according to the invention may be applied in a great variety of perfumed materials. Thus they may be applied e.g. in soaps, detergents, shampoos, toilet waters or in cosmetic preparations, such as shave lotions, sun creams, face creams and tallow powders.

We claim:

1. A perfume composition comprising from 5 to 16% of 2-n-butyl-4,4,6-trimethyl-1,3-dioxane in a perfume carrier.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
GB981285A * Title not available
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3966647 *Apr 8, 1975Jun 29, 1976Lever Brothers CompanyPerfume compositions containing monoalkyl-para-dioxanes
US4124541 *Jun 15, 1977Nov 7, 1978Henkel Kommanditgesellschaft Auf AktienDioxa bicyclo dodecane and -hexadecane perfume compositions
US4146506 *Oct 21, 1977Mar 27, 1979Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa)Perfume compositions with 4-isopropyl-5,5-dimethyl-1,3-dioxane
US4198323 *Jul 12, 1978Apr 15, 1980Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa)2,2,5-Trimethyl-5-phenyl-1,3-dioxane and perfume compositions containing it
US4211674 *Mar 23, 1979Jul 8, 1980Polak's Frutal Works B.V.Cyclic acetals and ketals and their use in perfume compositions
US4372880 *Apr 15, 1981Feb 8, 1983Henkel Kommanditgesellschaft Auf AktienUse of substituted 2-(1-methylbutyl)-1,3-dioxanes as perfuming agents
EP1316553A1 *Nov 21, 2002Jun 4, 2003Celanese Chemicals Europe GmbHFragrances based on cyclic acetals
EP1481974A1 *Nov 21, 2002Dec 1, 2004Celanese Chemicals Europe GmbHFragrances based on cyclic acetals
Classifications
U.S. Classification512/12
International ClassificationC11B9/00, C07D319/06, A61K8/49, A61Q13/00
Cooperative ClassificationC07D319/06, C11B9/008
European ClassificationC07D319/06, C11B9/00H2B