EP0134613A1 - Compositions de parfum et produits parfumés contenant au moins un ou plusieurs esters de l'acide 2-éthyle-2-méthyle butanoique comme base parfumante - Google Patents

Compositions de parfum et produits parfumés contenant au moins un ou plusieurs esters de l'acide 2-éthyle-2-méthyle butanoique comme base parfumante Download PDF

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Publication number
EP0134613A1
EP0134613A1 EP84201183A EP84201183A EP0134613A1 EP 0134613 A1 EP0134613 A1 EP 0134613A1 EP 84201183 A EP84201183 A EP 84201183A EP 84201183 A EP84201183 A EP 84201183A EP 0134613 A1 EP0134613 A1 EP 0134613A1
Authority
EP
European Patent Office
Prior art keywords
ethyl
methyl
esters
butanoic acid
perfume
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP84201183A
Other languages
German (de)
English (en)
Inventor
Hermannus Boelens
Willem Brakmann
Theodorus Gerardus Maria Hesp
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Naarden International NV
Original Assignee
Naarden International NV
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 Naarden International NV filed Critical Naarden International NV
Publication of EP0134613A1 publication Critical patent/EP0134613A1/fr
Withdrawn legal-status Critical Current

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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
    • C11B9/0007—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

Definitions

  • Perfume compositions and perfumed products which contain at Least one or more esters of 2-ethyL-2-methyL-butanoic acid as the perfume base.
  • the invention relates to perfume compositions which contain at Least one or more esters of 2-ethyL-2-methyL-butanoic acid as the perfume base and to products perfumed with these compounds or with perfume compositions containing these compounds.
  • esters of 2-ethyL-2-methyl-butanoic acid having the general formula wherein R represents an alkyl, alkenyl, aLkoxyaLkyL, cycLoaLkyL, alkylcycloalkyl, cycloalkylalkyl or araLkyL group having a maximum of 8 carbon atoms are vaLuabLe fragrances.They are capable of imparting diverse desired odour notes to perfume compositions and products, namely odour notes of the green, fruity, minty, woody and fLoraL type.
  • the ethyl ester in particular, is distinguished by a natural odour character.
  • esters according to the invention are pre pared in accordance with generally known esterification methods, for example by reaction of the corresponding aLcohoL with 2-ethyL-2-methyL-butanoic acid or with a customary derivative thereof, such as the acid chloride.
  • esters according to the invention can be used successfully in perfume compositions or are used directly as odour-imparting agents in a variety of products.
  • perfume composition there is here meant a mixture of fragrances and,optionally, auxiliaries, if desired dissolved in a suitable solvent or mixed with a pulverulent substrate, which mixture is used in order to impart a desired odour to the skin and/or to a variety of products.
  • ExampLes of such products are soaps, detergents, air fresheners, room sprays, pomanders, candles and cosmetics, such as creams, ointments, toilet waters, pre-shave and after-shave Lotions, talcum powders, hair- care compositions, body deodorants and antiperspirants.
  • Fragrances and mixtures thereof which can be used, in combination with the compounds according to the invention, for the preparation of perfume compositions are, for example: natural products such as ethereal oils, absolutes, resinoids, resins, concretes and the Like, but also synthetic fragranoes such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ke- taLs, nitriles and the Like, these including saturated and unsaturated compounds and aliphatic, carbocyclic and heterocyclic compounds.
  • ExampLes of fragrances which can be used in combination with the compounds according to the invention are geranioL, geranyl acetate, Linalool, linalyl acetate, tetrahydroLinaLooL, citronellol, citro- neLLyL acetate, dihydromyrcenoL, dihydromyrcenyL acetate, tetrahydromyrcenoL, terpineol, terpinyl acetate, nopoL, nopyL acetate, 2-phenylethanol, 2-phenyLethyL acetate, benzyl aLcohoL, benzyl acetate, benzyl saLicyLate, styr- aLLyL acetate, benzyl benzoate, amyL saLicyLate, dimethyl- benzylcarbinol, trichLoromethyLphenyLcar
  • tetralin musks isochromane musks, macrocyclic ketones, macroLactone musks, ethylene brassylate and aromatic nitro musks.
  • perfume compositions which contain one or more compounds according to the invention are, for example: ethanoL, isopropanoL, diethylene gLycoL monoethyl ether, diethyl phthalate and the Like.
  • the quantities in which the compounds according to the invention can be used in perfume compositions or to perfume products can vary within wide Limits and depend, inter alia, on the nature of the product wherein the fragrance is used, on the nature and amount of the other components in the perfume composition and on the desired odour effect. Hence, it is only possible to specify very rough Limits, but these provide information sufficient for a man skiLLed in the art to be able independently to use the compounds according to the invention. In most cases an amount of only 0.1% by weight in a perfume composition wiLL already be sufficient to achieve a cLearLy perceptible odour effect. On the other hand it is possible, in order to achieve special odour effects, to use amounts of 20% by weight or even more in a composition. In products perfumed with the aid of perfume' compositions, these concentrations are correspondingly lower, depending on the quantity of perfume composition used in the product.
  • 260 g of concentrated sulphuric acid are added in 15 minutes, with efficient stirring, to a mixture of 260 g (2 moL) of 2-ethyL-2-methyL-butanoic acid and 386 g (8 mol) of ethanol. In the course thereof, the temperature rises to about 60°C. The mixture is then heated for 3 hours under reflux, with stirring. When the mixture has cooled to room temperature, the Layers are separated.
  • the Lower Layer is diluted with 200 mL of water and then extracted with cyclohexane.
  • the cyclohexane Layer is combined with the original upper Layer and the mixture washed neutral with sodium carbonate solution.
  • the cyclohexane solution is then evaporated and the residue distiLLed under reduced pressure.
  • the compound has a pleasant fruity and woody odour with aspects which are pronounced of tagetes oiL.
  • the compound has a pleasant minty and somewhat fruity odour.
  • a perfume composition of the pine type, very suitable for shampoos and shower and bath foam preparations was prepared in accordance with the following recipe:
  • a perfume composition of the floral fantasy type was prepared in accordance with the following recipe:

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)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP84201183A 1983-08-17 1984-08-14 Compositions de parfum et produits parfumés contenant au moins un ou plusieurs esters de l'acide 2-éthyle-2-méthyle butanoique comme base parfumante Withdrawn EP0134613A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL8302893 1983-08-17
NL8302893A NL8302893A (nl) 1983-08-17 1983-08-17 Parfumcomposities en geparfumeerde produkten die ten minste een of meer esters van 2-ethyl-2-methyl-butaanzuur als parfumgrondstof bevatten.

Publications (1)

Publication Number Publication Date
EP0134613A1 true EP0134613A1 (fr) 1985-03-20

Family

ID=19842279

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84201183A Withdrawn EP0134613A1 (fr) 1983-08-17 1984-08-14 Compositions de parfum et produits parfumés contenant au moins un ou plusieurs esters de l'acide 2-éthyle-2-méthyle butanoique comme base parfumante

Country Status (3)

Country Link
EP (1) EP0134613A1 (fr)
JP (1) JPS6067445A (fr)
NL (1) NL8302893A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3597626A1 (fr) * 2018-07-19 2020-01-22 Basf Se Esters d'acide carboxylique alpha, alpha-disubstitués pour une utilisation comme substances chimiques aromatiques

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5080776B2 (ja) * 2006-10-06 2012-11-21 花王株式会社 エステル化合物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1553487A (en) * 1976-06-11 1979-09-26 Henkel Kgaa Perfumes and perfume compositions

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1553487A (en) * 1976-06-11 1979-09-26 Henkel Kgaa Perfumes and perfume compositions

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 80, no. 9, March 4, 1974, page 315, no. 47419k, Columbus, Ohio, US; M.B. ORDYAN et al.: "Hydrocarbalkoxylation reactions. VII. Synthesis of esters from 1-hexene using formic acid and methanol under phosphoric acid catalysis conditions" *
CHEMICAL ABSTRACTS, vol. 85, no. 19, November 8, 1976, page 483, no. 142570q, Columbus, Ohio, US; S.D. PIROZHKOV et al.: "Synthesis of allyl esters of neo acids" & ZH. PRIKL. KHIM. (LENINGRAD) 1976, 49(7), 1646-8 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3597626A1 (fr) * 2018-07-19 2020-01-22 Basf Se Esters d'acide carboxylique alpha, alpha-disubstitués pour une utilisation comme substances chimiques aromatiques
WO2020016421A1 (fr) * 2018-07-19 2020-01-23 Basf Se ESTERS D'ACIDE CARBOXYLIQUE α, α-DISUBSTITUÉS DESTINÉS À ÊTRE UTILISÉS EN TANT QUE PRODUITS CHIMIQUES AROMATIQUES
CN112469689A (zh) * 2018-07-19 2021-03-09 巴斯夫欧洲公司 用作芳香化学品的α,α-二取代羧酸酯
US11542221B2 (en) * 2018-07-19 2023-01-03 Basf Se α, α-disubstituted carboxylic acid esters for use as aroma chemicals
CN112469689B (zh) * 2018-07-19 2024-03-26 巴斯夫欧洲公司 用作芳香化学品的α,α-二取代羧酸酯

Also Published As

Publication number Publication date
NL8302893A (nl) 1985-03-18
JPS6067445A (ja) 1985-04-17

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Legal Events

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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AK Designated contracting states

Designated state(s): CH DE FR GB LI NL

17P Request for examination filed

Effective date: 19850918

17Q First examination report despatched

Effective date: 19860724

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19861204

RIN1 Information on inventor provided before grant (corrected)

Inventor name: BRAKMANN, WILLEM

Inventor name: HESP, THEODORUS GERARDUS MARIA

Inventor name: BOELENS, HERMANNUS