WO1996039371A1 - Composes carbonyles aromatiques - Google Patents

Composes carbonyles aromatiques Download PDF

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Publication number
WO1996039371A1
WO1996039371A1 PCT/EP1996/002282 EP9602282W WO9639371A1 WO 1996039371 A1 WO1996039371 A1 WO 1996039371A1 EP 9602282 W EP9602282 W EP 9602282W WO 9639371 A1 WO9639371 A1 WO 9639371A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen
compounds
carbon atoms
alkyl group
carbonyl compounds
Prior art date
Application number
PCT/EP1996/002282
Other languages
German (de)
English (en)
Inventor
Thomas Markert
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1996039371A1 publication Critical patent/WO1996039371A1/fr

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Classifications

    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • the invention relates to the use of special aromatic carbonyl compounds of the structure given below as fragrances.
  • fragrance industry has a constant need for new fragrances with interesting fragrance notes in order to supplement the range of naturally available fragrances and to make the necessary adaptations to changing fashionable tastes, as well as the constantly increasing need for odor improvers for everyday products To cover needs such as cosmetics and cleaning agents.
  • the compounds of the general formula (I) meet the above requirements excellently in all respects and can advantageously be used as fragrances with differently nuanced odor notes with good adhesive strength.
  • the compounds of the formula (I) have an improved odor intensity over compounds of the prior art which are structurally close to them, i.e. develop their effect at lower concentrations.
  • the present invention relates to the use of aromatic carbonyl compounds of the general formula (I)
  • radicals R to R3 independently of one another are hydrogen or an alkyl group having 1 to 4 carbon atoms
  • radical R 4 is hydrogen or an alkyl group having 1 to 4 carbon atoms and
  • Ph is a phenyl group
  • fragrances mean as fragrances.
  • the radical R is methyl.
  • the radicals R2 and R3 are hydrogen.
  • R 4 is hydrogen, methyl or ethyl.
  • 4-phenyl-hexan-2-one is very particularly preferred. It is characterized by an olfactory characteristic, in which fruity, floral as well as cinnamon and As ascone pronounced notes dominate and excellent stability in recipes from cosmetics and perfumery.
  • the compounds (I) are prepared by known synthetic organic chemical methods.
  • the compounds (I) are preferably produced in a 2-stage process.
  • An aromatic and (olefinically) unsaturated carbonyl compound, the C C double bond of which is subsequently selectively hydrogenated in a customary manner, is first produced in a first stage by means of the so-called Carroll reaction from the corresponding allyl alcohols (eg cinnamon alcohol) .
  • Carroll reaction in the context of the present invention means the conversion of allyl alcohols into gamma-delta-unsaturated ketones.
  • the allyl alcohol is converted into the corresponding allyl acetoacetate by reaction with acetoacetic ester, from which the alpha-allylacetoacetic acid is formed by [3,3] sigmatropic rearrangement (Claisen rearrangement) thermal decarboxylation gives the desired gamma-delta unsaturated ketone (I).
  • the allyl acetoacetate can be used in bulk or formed in situ.
  • allyl alcohols are reacted with 2-alkoxyalkenes, in particular 2-methoxypropene, in the Carroll reaction.
  • 2-alkoxyalkenes in particular 2-methoxypropene
  • the intermediate allyl vinyl ether can be isolated or subjected directly to the subsequent [3,3] sigmatropic rearrangement to the corresponding ketone (I) in situ.
  • the invention therefore furthermore relates to a process for the preparation of the aromatic carbonyl compounds (I) by a Carroll reaction from the corresponding allyl alcohols, together with selective hydrogenation of the C CC double bond of the primary product obtained in the Carroll reaction.
  • This is the variant in which the [3,3] sigmatropic rearrangement takes place via the allyl vinyl ether in the course of the Carroll reaction and in which the Allyl alcohol used at the beginning of the synthesis is reacted with a 2-alkoxyalkene, preferably since this type of preparation ensures a particularly high product purity and thus the desired high olfactory quality of the compounds (I) is ensured.
  • the compounds (I) reinforce the harmony and charisma and naturalness as well as the adhesion, the dosage being matched to the desired fragrance note, taking into account the other components of the composition.
  • the compounds of the formula (I) are particularly suitable for modifying and enhancing known compositions. Particularly to be emphasized is their extraordinary olfactory strength, which generally contributes to the refinement of the composition.
  • the compounds of formula (I) can be combined with numerous known fragrance ingredients, for example other fragrances of natural, synthetic or partially synthetic origin, essential oils and plant extracts.
  • the range of natural fragrances can include both volatile and moderately volatile components and that of synthetic fragrances include representatives from practically all classes of substances. Examples are:
  • Natural products such as tree moss absolute, basil oil, agricultural oils such as bergamot oil, mandarin oil, etc., mastic absolute, myrtle oil, pal arosa oil, patchouli oil, petitgrain oil, wormwood oil, myrrh oil, olibanum oil
  • aldehydes such as citral, HelionalR, ⁇ -hexylcinnamaldehyde, hydroxycitronellal, Lilial R [p-tert-butyl- ⁇ -methyldihydrocinnamaldehyde], methylnonyl acetaldehyde,
  • ketones such as allyl ionone, ⁇ -ionone, ⁇ -ionone, isoraldein, methyl ionone,
  • esters such as allylphenoxyacetate, benzyl salicylate, cinnamylpropionate, citronellylacetate, decyl acetate, dimethylbenzylcarbinylacetate, ethyllacetoacetate, hexenylisobutyrate, linalyl acetate, methyldihydrojasmonate, vetiveryl acetate, cyclylatyl cyclylhexyl
  • lactones such as gamma-undecalactone, l-0xaspiro [4.4] nonan-2-one,
  • perfumery such as musk and sandalwood fragrances, indole, p-menthan-8-thiol-3-one, methylleugenol, ambroxan.
  • the compounds according to the invention contain centers of chirality, so that these compounds can exist in different spatial forms.
  • the compounds according to the invention are obtained as mixtures of the corresponding isomers and are used as such as fragrances.
  • the usable proportions of the compounds according to the invention or their mixtures in fragrance compositions range from 1 to 70 percent by weight, based on the mixture as a whole.
  • compositions of this type can be used both for perfuming cosmetic preparations such as lotions, creams, sha poos, soaps, ointments, powders, aerosols, toothpastes, mouthwashes, deodorants and in alcoholic perfumery (eg Eaux de Cologne, Eaux de Toilette, extras) can be used.
  • perfuming technical products 1 such as detergents and cleaning agents, fabric softeners and textile treatment agents.
  • the compositions are added to them in an olfactory effective amount, in particular in a concentration of 0.05 to 2 percent by weight, based on the entire product.
  • these values are not intended to represent any limit values, since the experienced perfumer can achieve effects with even lower concentrations or can build up new types of complexes with even higher doses.
  • Cinnamon alcohol 98% (Riedel de Haen)
  • Perfume concentrate for perfuming soap (floral-fresh fantasy composition):

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des composés carbonyles aromatiques de formule générale (I), dans laquelle les restes R1 à R3 désignent, indépendamment l'un de l'autre, l'hydrogène ou un groupe alkyle avec 1 à 4 atomes de carbone; le reste R4 désigne l'hydrogène ou un groupe alkyle avec 1 à 4 atomes de carbone, et Ph désigne un groupe phényle. Ces composés se distinguent par le fait qu'ils présentent des notes de parfums intéressantes, de grande diffusion et conviennent pour l'utilisation comme parfums, par exemple, dans des préparations cosmétiques, des produits techniques ou des parfums alcoolisés.
PCT/EP1996/002282 1995-06-06 1996-05-28 Composes carbonyles aromatiques WO1996039371A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19520556.1 1995-06-06
DE1995120556 DE19520556A1 (de) 1995-06-06 1995-06-06 Aromatische Carbonylverbindungen

Publications (1)

Publication Number Publication Date
WO1996039371A1 true WO1996039371A1 (fr) 1996-12-12

Family

ID=7763697

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/002282 WO1996039371A1 (fr) 1995-06-06 1996-05-28 Composes carbonyles aromatiques

Country Status (2)

Country Link
DE (1) DE19520556A1 (fr)
WO (1) WO1996039371A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1526791A (fr) * 1963-11-05 1968-05-31 Int Flavors & Fragrances Inc Aryl- ou cyclohexyl-alcanones, compositions contenant de telles substances, et procédés pour leur préparation
US3793376A (en) * 1970-06-04 1974-02-19 Int Flavors & Fragrances Inc Process for producing 3-phenyl pentenals
DE2340812A1 (de) * 1973-08-11 1975-02-27 Basf Ag Phenylpropanale, sowie ein verfahren zu deren herstellung
DE4415690A1 (de) * 1994-05-04 1995-11-09 Henkel Kgaa Aromatische Carbonylverbindungen

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1526791A (fr) * 1963-11-05 1968-05-31 Int Flavors & Fragrances Inc Aryl- ou cyclohexyl-alcanones, compositions contenant de telles substances, et procédés pour leur préparation
US3793376A (en) * 1970-06-04 1974-02-19 Int Flavors & Fragrances Inc Process for producing 3-phenyl pentenals
DE2340812A1 (de) * 1973-08-11 1975-02-27 Basf Ag Phenylpropanale, sowie ein verfahren zu deren herstellung
DE4415690A1 (de) * 1994-05-04 1995-11-09 Henkel Kgaa Aromatische Carbonylverbindungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
A.W. BURGSTAHLER ET AL.: "Thermal Rearrangement of Arylmethyl Vinyl Ethers", JOURNAL OF THE CHEMICAL SOCIETY, 1963, LETCHWORTH GB, pages 4986 - 4989, XP002013858 *

Also Published As

Publication number Publication date
DE19520556A1 (de) 1996-12-12

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