EP0134613A1 - Perfume compositions and perfumed products which contain at least one or more esters of 2-ethyl-2-methyl-butanoic acid as the perfume base - Google Patents

Perfume compositions and perfumed products which contain at least one or more esters of 2-ethyl-2-methyl-butanoic acid as the perfume base 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
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Prior art keywords
ethyl
methyl
esters
butanoic acid
perfume
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EP84201183A
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German (de)
French (fr)
Inventor
Hermannus Boelens
Willem Brakmann
Theodorus Gerardus Maria Hesp
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Naarden International NV
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Naarden International NV
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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

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:

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  • 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)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Perfume compositions and perfumed products containing at least one or more 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 at most 8 carbon atoms.

Description

  • 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.
  • There is continuing interest in the preparation and use of synthetic fragrances tecause these, in contrast to natural products, can at aLL times be prepared in an amount appropriate to demand, and in constant quality.
  • It has now been found that esters of 2-ethyL-2-methyl-butanoic acid having the general formula
    Figure imgb0001
    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. This ethyl ester has been described in British Patent Specification 1,004,286 and by J.R. RoLand, J.D.C. Wilson and W.E. Hanford in J.Am. Chem. Soc. 72, 2122-24 (1950). However, in neither pubLication is there to be found any indication of the usefulness of this compound as a perfume base. As regards the upper Limit of 8 carbon atoms, we record, for the sake of completeness, that the votatility and therefore the odour intensity of esters of 2-ethyL-2-methyLbutanoic acid where R contains more than 8 carbon atoms is considered insufficient.
  • The 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.
  • The 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. By the expression "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, trichLoromethyLphenyLcarbinyL acetate, p-tert.-butyL-cycLohexyL acetate, isononyl acetate, vetiveryL acetate, vetiverol, aLpha-hexyLcinnamaLdehyde, 2-methyL-3-(p-tert.-butyLphenyL)-propanaL, 2-methyL-3-(p-isopropyLphenyL)-propanaL, 3-(p-tert.-butyLphenyL)-propanal, tricycLodecenyL acetate, tricycLodecenyL propionate, 4-(4-hydroxy-4-methyLpentyL)-cycLohex-3-ene- carbaldehyde, 4-(4-methyL-3-pentenyL)-cycLohex-3-ene- carbaldehyde, 4-acetoxy-3-pentyL-tetrahydropyran , 3-carboxymethyl-2-pentylcyclopentane, 2-n-heptyLcycLopen- tanone, 3-methyL-2-pentyL-2-cycLopentenone, n-decanal, n-dodecanal, dec-9-en-1-ot, phenoxyethyl isobutyrate, phenyLacetaLdehyde dimethylacetal, phenyLacetaLdehyde diethylacetal, geranylnitrile, citronellylnitrile, cedryl acetate, 3-isocamphyl-cyclohexanol, cedryl methyl ether, isoLongifoLanone, aubepinenitrile, aubepine, heliotropine, coumarin, eugenol, vanillin, diphenyl oxide, hydroxy- citronellal, ionones, methyLionones, isomethylionones, irones, cis-hex-3-enoL and esters thereof, indane musks,
  • tetralin musks, isochromane musks, macrocyclic ketones, macroLactone musks, ethylene brassylate and aromatic nitro musks.
  • AuxiLiaries and solvents which can be used in 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.
  • The examples which foLLow serve soLeLy to ilius- trate the preparation and use of the compounds according to the invention, but the invention is not restricted thereto.
    • ExampLe I
  • Preparation of ethyL 2-ethyL-2-methyL-butyrate.
  • 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. 258 g of the desired ethyl ester are obtained, boiling point 65°C/0.3 kPa; n20 = 1.4110; NMR (100 MHz, δ in ppm against TMS, soLvent: CCL4); 0.81 (6H,t,J = 7Hz); 1.06 (3H,s); 1.24 (3H,t,J = 7 Hz); 1.0-1.9 (4H,m); 4.08 (2H,q,J = 7Hz).
  • The compound has a pleasant fruity and woody odour with aspects which are reminiscent of tagetes oiL.
    • ExampLe II
  • Preparation of 2'-ethyLhexyL 2-ethyL-2-methyL-butyrate.
  • A mixture of 15.5 g (0.12 moL) of 2-ethyLhexanoL, 13 g (0.1 mol) of 2-ethyl-2-methyl-butanoic acid, 100 mg of p-toluenesulphonic acid and 150 mL of toluene is heated to the reflux temperature, the water formed being distiLLed off azeotropicaLLy. When the mixture has cooled to room temperature, it is washed neutral with sodium carbonate sotution. The toluene solution is then evaporated and the residue distiLLed under reduced pressure. 14.5 g of the desired ester are obtained, boiling point: 95°C/0.3 kPa; n24 = 1.4320; NMR: 0.81 (6H,t,J = 7Hz); 1.05 (3H,s); 0.6-1.9 (19H,m); 3.90 (2H,d,J = 6Hz).
  • The compound has a pleasant minty and somewhat fruity odour.
    • Example III
  • The following esters were prepared as described in ExampLe II:
    • ALLyL 2-ethyl-2-methyl-butyrate:
      • boiling point: 950C/0.3 kPa; NMR: 0.81 (6H,t,J = 7Hz), 1.08 (3H,s); 1.0-1.9 (4H,m); 4.49 (2H,d with fine structure, J = 7Hz); 5.0-5.4 (2H,m); 5.6-6.1 (1H,m).
    • Spicy green and floral odour, somewhat reminiscent of tagetes oiL.
    • IsobutyL 2-ethyL-2-methyL-butyrate:
      • boiling point: 90°C/0.3 kPa; n20 D = 1.4155; NMR: 0.81 (6H,t,J = 7Jz); 0.94 (6H,d,J = 7Hz); 1.06 (3H,s); 1.0-2.2 (5H,m); 3.78 (2H,d,J = 6Hz).
    • Woody and minty odour with floral tones.
      • CycLohexyL 2-ethyL-2-methyL-butyrate: boiling point: 90°C/0.3 kPa; n20 D = 1.4462; NMR: 0.80 (6H,t,J = 7Hz); 1.04 (3H, s); 1.0-2.0 (14H,m); 4.65 (1H,m). Fruity odour.
    • 2'-methoxyethyL 2-ethyL-2-methyL-butyrate:
      • boiling point: 750C/0.3 kPa; NMR: 0.81 (6H,t,7Hz); 1.06 (3H,s); 1.0-1.9 (4H,m); 3.30 (3H,s); 3.46 (2H,t,J = 5Hz); 4.12 (2H,t,J = 5Hz).
    • Green and somewhat woody odour.
    • BenzyL 2-ethyL-2-methyL-butyrate:
      • boiling point: 1180C/0.3 kPa; n20 D = 1.4890; NMR: 0.77 (6H,t,J = 7Hz); 1.07 (3H,s); 1.0-1.9 (4H,m); 5.00 (2H,s); 7.0-7.3 (5H, broad s).
    • Green and somewhat floral odour.
    • 2'-phenyLethyL 2-ethyL-2-methyL-butyrate: boiling point: 1250C/0.3 kPa; n20 D = 1.4830; NMR:
      • 0.73 (6H,t,J = 7Hz); 1.01 (3H,s); 1.0-1.9 (4H,m); 2.86 (2H,t,J = 7Hz); 4.20 (2H,t,J = 7Hz); 6.9-7.3 (5H, broad s).
    • FLoraL and somewhat fruity odour.
    Example IV
  • 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:
    • 345 parts by weight of bornyl acetate
    • 100 parts by weight of 2-butyl-4,4,6-trimethyt-1,3-dioxane
    • 50 parts by weight of Siberian pine-needle oiL
    • 30 parts by weight of 5-acetyl-3-isopropyl-1,1,2,6-tetramethyl-indane
    • 30 parts by weight of benzyl acetate .
    • 30 parts by weight of orange oil
    • 30 parts by weight of linalyl acetate
    • 20 parts by weight of olibanum resinoid
    • 20 parts by weight of tridecanal
    • 15 parts by weight of 4-tert.-butyLcycLohexyL acetate
    • 10 parts by weight of coumarin
    • 10 parts by weight of terpineol
    • 10 parts by weight of terpinyl acetate
    • 10 parts by weight of Lavandin oil
    • 10 parts by weight of n-decanal
    • 7 parts by weight of CitrovertaL NB 104*
    • 5 parts by weight of dodecanal
    • 5 parts by weight of styralyl acetate
    • 5 parts by weight of 3-isocamphyLcycLohexanoL
    • 3 parts by weight of α-ionone
    • 2 parts by weight of isoeugenol
    • 30 parts by weight of ethyl 2-ethyL-2-methyLbutyrate
    • 218 parts by weight of dipropylene gLycoL 1000 parts by weight
    Example V
  • A perfume composition of the floral fantasy type was prepared in accordance with the following recipe:
    • 350 parts by weight of LiLy of the valley base* 200 parts by weight of LiLac base*
      Figure imgb0002

Claims (5)

1. Perfume composition or perfumed product, characterised in that it contains one or more esters of 2-ethyL-2-methyL-butanoic acid of the formula
Figure imgb0003
wherein R represents an aLkyL, aLkenyL, aLkoxyaLkyL, cycLoaLkyL, alkylcycloalkyl, cycloalkylalkyl or araLkyL group having at most 8 carbon atoms.
2. Perfume composition or perfumed product according to CLaim 1, characterised in that it contains the ethyl ester of 2-ethyL-2-methyL-butanoic acid.
3. Perfume composition according to CLaim 1, characterised in that it contains at Least 0.1% of one or more of the esters of 2-ethyL-2-methyL-butanoic acid defined in CLaim 1.
4. Use of a perfume composition according to one or more of CLaims 1-3 or of one or more of the esters of 2-ethyl-2-methyl-butanoic acid defined in CLaim 1 for the perfuming of products.
5. Esters of 2-ethyL-2-methyL-butanoic acid of the formuLa
Figure imgb0004
wherein R represents an aLkyL, aLkenyL, alkoxyalkyl, cycloalkyl, alkytcycloalkyl, cycLoaLkyLaLkyL or araLkyL group having at most 8 carbon atoms, with the proviso that the ethyl ester of 2-ethyl-2-methyl-butanoic acid is excluded.
EP84201183A 1983-08-17 1984-08-14 Perfume compositions and perfumed products which contain at least one or more esters of 2-ethyl-2-methyl-butanoic acid as the perfume base Withdrawn EP0134613A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL8302893 1983-08-17
NL8302893A NL8302893A (en) 1983-08-17 1983-08-17 PERFUME COMPOSITIONS AND PERFUMED PRODUCTS CONTAINING AT LEAST ONE OR MORE ESTERS OF 2-ETHYL-2-METHYL-BUTANIC ACID AS PERFUME RAW.

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EP0134613A1 true EP0134613A1 (en) 1985-03-20

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3597626A1 (en) * 2018-07-19 2020-01-22 Basf Se Alpha,alpha-disubstituted carboxylic acid esters for use as aroma chemicals

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5080776B2 (en) * 2006-10-06 2012-11-21 花王株式会社 Ester compound

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 (en) * 2018-07-19 2020-01-22 Basf Se Alpha,alpha-disubstituted carboxylic acid esters for use as aroma chemicals
WO2020016421A1 (en) * 2018-07-19 2020-01-23 Basf Se α, α-DISUBSTITUTED CARBOXYLIC ACID ESTERS FOR USE AS AROMA CHEMICALS
CN112469689A (en) * 2018-07-19 2021-03-09 巴斯夫欧洲公司 Alpha, alpha-disubstituted carboxylic acid esters as fragrance chemicals
US11542221B2 (en) * 2018-07-19 2023-01-03 Basf Se α, α-disubstituted carboxylic acid esters for use as aroma chemicals
CN112469689B (en) * 2018-07-19 2024-03-26 巴斯夫欧洲公司 Alpha, alpha-disubstituted carboxylic acid esters useful as fragrance chemicals

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RIN1 Information on inventor provided before grant (corrected)

Inventor name: BRAKMANN, WILLEM

Inventor name: HESP, THEODORUS GERARDUS MARIA

Inventor name: BOELENS, HERMANNUS