EP0098791B1 - 2-methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents - Google Patents

2-methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents Download PDF

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Publication number
EP0098791B1
EP0098791B1 EP83710043A EP83710043A EP0098791B1 EP 0098791 B1 EP0098791 B1 EP 0098791B1 EP 83710043 A EP83710043 A EP 83710043A EP 83710043 A EP83710043 A EP 83710043A EP 0098791 B1 EP0098791 B1 EP 0098791B1
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EP
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Prior art keywords
branched
acid esters
methylpentanoic acid
methylpentanoic
following formula
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EP83710043A
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German (de)
French (fr)
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EP0098791A1 (en
Inventor
Ulf Armin Dr. Schaper
Klaus Prof. Dr. Bruns
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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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

  • the compounds are prepared by esterification of 2-methylpentanoic acid with a branched or carbocyclic alcohol according to the general formula above.
  • the esterification reaction takes place according to known methods of organic chemistry.
  • the following compounds are particularly suitable as alcoholic components: 2-pentanol, 2-methylbutanol, 2-methylpentanol, 2-ethylbutanol, 2,3-dimethylbutanol, 2-ethylhexanol, cyclopentanol, cyclohexanol.
  • the 2-methylpentanoic acid-2-methylpentyl ester can be prepared particularly advantageously from 2-methylpentanal by reaction according to Claisen-Tischtschenko with aluminum alcoholate as a catalyst with disproportionation of the aldehyde to acid and alcohol, the components immediately reacting further to the desired ester.
  • the claimed 2-methylpentanoic acid esters are characterized by interesting floral, fruity, spicy, woody scents. They have an exceptional adhesive strength and can be combined very well with common perfume ingredients and other fragrances to create new compositions, which they also give a high adhesive strength.
  • the proportion of 2-methylpentanoic acid esters in the fragrance compositions is generally 1-50 percent by weight.
  • compositions can be used for the perfuming of cosmetic preparations, such as creams, lotions, scented water, aerosols, toilet soaps, and oral hygiene products, and in 1% perfumery. They can also be used to improve the smell of technical products such as washing and cleaning agents, fabric softeners. About 0.05-2 percent by weight of composition, based on the entire product, is used.
  • the claimed 2-methylpentanoic acid esters are new compounds, with the exception of the 2-methylpentanoic acid 2-methylpentyl ester.
  • the latter is described in Beilstein's Handbook of Organic Chemistry, Vol. 2, E II, page 943. However, no statement is made about the quality of the smell or perfume suitability.
  • DE-OS 25 30 227 discloses lower alkyl esters of 2-methylpentenic acid, optionally in a mixture with lower alkyl esters of 2-methylpentanoic acid, which serve as a seasoning essence for liquid and solid foods and the like or as a perfume for cosmetic and hygienic preparations.
  • 2-methylpentanoic acid esters with branched or carbocyclic alcohol components are mentioned according to their special properties.
  • reaction temperature was kept below 40 ° C. by cooling the flask with ice water. After a total of 3 g of the alcoholate mixture had been added, the reaction temperature was kept at 30 ° C. without external cooling.
  • the clear, colorless reaction mixture was mixed with cooling with 16 g of 10% sulfuric acid and taken up in 500 ml of ether.
  • the aqueous phase was separated off, the organic phase was washed neutral with water, dried and concentrated.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Beans For Foods Or Fodder (AREA)

Abstract

1. Claims (for the Contracting States : BE, CH, DE, FR, GB, IT, LI, NL) The use of 2-methylpentanoic acid esters corresponding to the following formula see diagramm : EP0098791,P6,F3 in which R is a branched or carbocyclic radical corresponding to the formula see diagramm : EP0098791,P6,F4 wherein R**1 = H, CH3 R**2 = H, CH3 , C2 H5 R**3 = C2 H5 , n-C3 H7 , CH(CH3 )2 , n-C4 H9 with the proviso that only one of the radicals R**1 , R**2 can represent H, or wherein R**1 , R**2 = (CH2 )n , n = 3 or 4 R**3 = H as perfumes. 1. Claims (for the Contracting State AT) The use of 2-methylpentanoic acid esters corresponding to the following formula see diagramm : EP0098791,P7,F3 in which R is a branched or carbocyclic radical corresponding to the following formula see diagramm : EP0098791,P7,F4 wherein R**1 = H, CH3 R**2 = H, CH3 , C2 H5 R**3 = C2 H5 , n-C3 H7 , CH(CH3 )2 , n-C4 H9 with the proviso that only one of the radicals R**1 , R**2 can represent H, or wherein R**1 , R**2 = (CH2 )n , n = 3 or 4 R**3 = H as perfumes.

Description

Es wurde gefunden, daß 2-Methylpentansäureester der Formel

Figure imgb0001
worin R ein verzweigter oder carbocyclischer Rest der Formel
Figure imgb0002
ist mit

  • R 1 = H, CH3
  • R2 = H, CH3, C2H5
  • R3 = C2H5, n-C3H7, CH(CH3)2, n-C4H9
    wobei nur einer der Reste R1, R2 = H sein kann oder mit
  • R1, R2 = (CH2)n, n = 3. oder 4
  • R3 = H
wertvolle Riechstoffe mit blumiger, fruchtiger, würziger, holziger Note mit hervorragender Haftfestigkeit sind.It has been found that 2-methylpentanoic acid ester of the formula
Figure imgb0001
 wherein R is a branched or carbocyclic radical of the formula
Figure imgb0002
 is with
  • R 1 = H, CH 3
  • R 2 = H, CH 3 , C 2 H 5
  • R 3 = C 2 H 5 , nC 3 H 7 , CH (CH 3 ) 2 , nC 4 H 9
    where only one of the radicals R 1 , R 2 = H or with
  • R 1, R 2 = (CH 2 ) n , n = 3rd or 4th
  • R 3 = H
are valuable fragrances with a floral, fruity, spicy, woody note with excellent adhesive strength.

Die Herstellung der Verbindungen erfolgt durch Veresterung von 2-Methylpentansäure mit einem verzweigten oder carbocyclischen Alkohol entsprechend der vorstehenden allgemeinen Formel. Die Veresterungsreaktion erfolgt nach bekannten Verfahren der organischen Chemie.The compounds are prepared by esterification of 2-methylpentanoic acid with a branched or carbocyclic alcohol according to the general formula above. The esterification reaction takes place according to known methods of organic chemistry.

Als alkoholische Komponente kommen vor allem folgende Verbindungen in Betracht : 2-Pentanol, 2-Methylbutanol, 2-Methylpentanol, 2-Ethylbutanol, 2,3-Dimethylbutanol, 2-Ethylhexanol, Cyclopentanol, Cyclohexanol.The following compounds are particularly suitable as alcoholic components: 2-pentanol, 2-methylbutanol, 2-methylpentanol, 2-ethylbutanol, 2,3-dimethylbutanol, 2-ethylhexanol, cyclopentanol, cyclohexanol.

Der 2-Methylpentansäure-2-Methylpentylester läßt sich besonders vorteilhaft herstellen aus 2-Methylpentanal durch Umsetzung nach Claisen-Tischtschenko mit Aluminiumalkoholat als Katalysator unter Disproportionierung des Aldehyds zu Säure und Alkohol, wobei die Komponenten unmittelbar zu dem gewünschten Ester weiterreagieren. Die beanspruchten 2-Methylpentansäureester zeichnen sich durch interessante blumige, fruchtige, würzige, holzige Geruchsnoten aus. Sie besitzen eine außergewöhnliche Haftfestigkeit und lassen sich sehr gut mit üblichen Parfüminhaltsstoffen und anderen Riechstoffen zu neuartigen Kompositionen kombinieren, denen sie ebenfalls eine hohe Haftfestigkeit verleihen. Der Anteil der 2-Methylpentansäureester in den Riechstoffkompositionen beträgt im allgemeinen 1-50 Gewichtsprozent. Derartige Kompositionen können zur Parfümierung von kosmetischen Präparaten, wie Cremes, Lotionen, Duftwässern, Aerosolen, Toiletteseifen, und Mundpflegemitteln, sowie in der Extrait-Parfümerie verwendet werden. Sie können ferner zur Geruchsverbesserung technischer Produkte, wie Wasch- und Reinigungsmittel, Weichspüler, dienen. Es werden etwa 0,05-2 Gewichtsprozent an Komposition, bezogen auf das gesamte Produkt, eingesetzt.The 2-methylpentanoic acid-2-methylpentyl ester can be prepared particularly advantageously from 2-methylpentanal by reaction according to Claisen-Tischtschenko with aluminum alcoholate as a catalyst with disproportionation of the aldehyde to acid and alcohol, the components immediately reacting further to the desired ester. The claimed 2-methylpentanoic acid esters are characterized by interesting floral, fruity, spicy, woody scents. They have an exceptional adhesive strength and can be combined very well with common perfume ingredients and other fragrances to create new compositions, which they also give a high adhesive strength. The proportion of 2-methylpentanoic acid esters in the fragrance compositions is generally 1-50 percent by weight. Such compositions can be used for the perfuming of cosmetic preparations, such as creams, lotions, scented water, aerosols, toilet soaps, and oral hygiene products, and in extrait perfumery. They can also be used to improve the smell of technical products such as washing and cleaning agents, fabric softeners. About 0.05-2 percent by weight of composition, based on the entire product, is used.

Die beanspruchten 2-Methylpentansäureester sind neue Verbindungen, mit Ausnahme des 2-Methylpentansäure-2-methylpentylesters. Letzterer ist in Beilsteins Handbuch der Organischen Chemie, Bd. 2, E II, Seite 943, beschrieben. Es wird jedoch keine Aussage über Geruchsqualität oder parfümistische Eignung gemacht.The claimed 2-methylpentanoic acid esters are new compounds, with the exception of the 2-methylpentanoic acid 2-methylpentyl ester. The latter is described in Beilstein's Handbook of Organic Chemistry, Vol. 2, E II, page 943. However, no statement is made about the quality of the smell or perfume suitability.

Aus DE-OS 25 30 227 sind niedere Alkylester der 2-Methylpentensäure, gegebenenfalls im Gemisch mit niederen Alkylestern der 2-Methylpentansäure bekannt, die als Würzessenz für flüssige und feste Lebensmittel und dergleichen bzw. als Parfüm für kosmetische und hygienische Präparate dienen. Es werden jedoch weder die beanspruchten 2-Methylpentansäureester mit verzweigter oder carbocyclischer Alkoholkomponente, nach deren besondere Eigenschaften erwähnt.DE-OS 25 30 227 discloses lower alkyl esters of 2-methylpentenic acid, optionally in a mixture with lower alkyl esters of 2-methylpentanoic acid, which serve as a seasoning essence for liquid and solid foods and the like or as a perfume for cosmetic and hygienic preparations. However, neither the claimed 2-methylpentanoic acid esters with branched or carbocyclic alcohol components are mentioned according to their special properties.

BeispieleExamples 1. Allgemeine Herstellvorschrift1. General manufacturing instructions

0,1 Mol 2-Methylpentansäure, 0,12 Mol verzweigter Alkohol, 100 ml Cyclohexan und 0,1 g Paratoluolsulfonsäure werden zum Sieden erhitzt. Das freigesetzte Wasser wird azeotrop ausgekreist. Nach beendeter Umsetzung wird das auf Raumtemperatur abgekühlte Reaktionsgemisch zunächst mit 10 %iger Natronlauge, danach mit gesättigter Natriumsulfatlösung neutral gewaschen, über Natriumsulfat getrocknet, im Vakuum eingeengt und über eine 20 cm Füllkörperkolonne destilliert.0.1 mol of 2-methylpentanoic acid, 0.12 mol of branched alcohol, 100 ml of cyclohexane and 0.1 g of paratoluenesulfonic acid are heated to boiling. The water released is removed azeotropically. When the reaction has ended, the reaction mixture, which has cooled to room temperature, is first treated with 10 % sodium hydroxide solution, then washed neutral with saturated sodium sulfate solution, dried over sodium sulfate, concentrated in vacuo and distilled over a 20 cm packed column.

Ausbeute : 70-90 % d. Th.Yield: 70-90% of theory Th.

Folgende Ester wurden nach dieser allgemeinen Herstellungsvorschrift hergestellt :

  • 1a) 2-Methylpentansäure-2-pentylester
    Figure imgb0003
    Geruch : fruchtig, nach Banane
  • 1 b) 2-Methylpentansäure-2-methylbutylester
    Figure imgb0004
    Geruch : Kamille-Note, würzig
  • 1c) 2-Methylpentansäure-2-methylpentylester
    Figure imgb0005
    Geruch : Apfelschale-Note, rosig, grün
  • ld) 2-Methylpentansäure-2-ethylbutylester
    Figure imgb0006
    Geruch : fruchtig
  • 1e) 2-Methylpentansäure-2,3-dimethylbutylester
    Figure imgb0007
    Geruch ; würzig
  • 1f) 2-Methylpentansäure-2-ethylhexylester
    Figure imgb0008
    Geruch : holzig, Guajak-Note
  • 1g) 2-Methylpentansäure-cyclopentylester
    Figure imgb0009
    Geruch : würzig
  • 1 h) 2-Methylpentansäure-cyclohexylester
    Figure imgb0010
    Geruch : Rosenoxid-Note
The following esters were produced according to this general manufacturing specification:
  • 1a) 2-pentyl 2-methylpentanoate
    Figure imgb0003
    Smell: fruity, like banana
  • 1 b) 2-methylpentanoic acid-2-methylbutyl ester
    Figure imgb0004
    Smell: Chamomile note, spicy
  • 1c) 2-methylpentanoic acid, 2-methylpentyl ester
    Figure imgb0005
    Smell: apple skin note, rosy, green
  • ld) 2-methylpentanoic acid 2-ethyl butyl ester
    Figure imgb0006
    Smell: fruity
  • 1e) 2,3-dimethylbutyl 2-methylpentanoate
    Figure imgb0007
    Smell; spicy
  • 1f) 2-methylpentanoic acid 2-ethylhexyl ester
    Figure imgb0008
    Smell: woody, guaiac note
  • 1g) Cyclopentyl 2-methylpentanoate
    Figure imgb0009
    Odor: spicy
  • 1 h) cyclohexyl 2-methylpentanoate
    Figure imgb0010
    Smell: Rose oxide note

2. Claisen-Tischtschenko-Reaktion mit 2-Methylpentanal zur Herstellung von 2-Methylpentansäure-2-methylpentylester2. Claisen-Tischchenko reaction with 2-methylpentanal to produce 2-methylpentanoic acid-2-methylpentyl ester

100 g 2-Methylpentanal wurden unter Rühren tropfenweise bei Raumtemperatur mit 5 g eines Gemisches aus zwei Teilen Aluminiumisopropylat und einem Teil Aluminiumisobutyrat versetzt.5 g of a mixture of two parts of aluminum isopropylate and one part of aluminum isobutyrate were added dropwise at room temperature to 100 g of 2-methylpentanal while stirring.

Nach Zugabe von ca. 1 g des Alkoholat-Gemisches trat eine exotherme Reaktion ein. Die Reaktionstemperatur wurde durch Kühlung des Kolbens mit Eiswasser unter 40 °C gehalten. Nach Zugabe von insgesamt 3 g des Alkoholat-Gemisches hielt sich die Reaktionstemperatur ohne äußere Kühlung bei 30 °C.After adding about 1 g of the alcoholate mixture, an exothermic reaction occurred. The reaction temperature was kept below 40 ° C. by cooling the flask with ice water. After a total of 3 g of the alcoholate mixture had been added, the reaction temperature was kept at 30 ° C. without external cooling.

Das klare, farblose Reaktionsgemisch wurde unter Kühlung mit 16 g 10 %iger Schwefelsäure versetzt und in 500 ml Ether aufgenommen. Die wäßrige Phase wurde abgetrennt, die organische Phase mit Wasser neutral gewaschen, getrocknet und eingeengt.The clear, colorless reaction mixture was mixed with cooling with 16 g of 10% sulfuric acid and taken up in 500 ml of ether. The aqueous phase was separated off, the organic phase was washed neutral with water, dried and concentrated.

104 g Rohprodukt wurden über eine 20 cm Füllkörperkolonne destilliert und ergaben 81,8 g des gewünschten Esters mit einem Siedepunkt von 104 °C bei 17 mbar.

Figure imgb0011
Figure imgb0012
 104 g of crude product were distilled through a 20 cm packed column and gave 81.8 g of the desired ester with a boiling point of 104 ° C. at 17 mbar.
Figure imgb0011
Figure imgb0012

Claims (4)

1. The use of 2-methylpentanoic acid esters corresponding to the following formula
Figure imgb0025
in which R is a branched or carbocyclic radical corresponding to the following formula
Figure imgb0026
wherein
R1 = H, CH3
R2 = H, CH3, C2H5
Rs = C2H5, n-C3H7, CH(CH3)2, n-C4H9
with the proviso that only one of the radicals R1, R2 can represent H, or wherein
R1, R2 = (CH2)n, n = 3 or 4
R3 = H

as perfumes.
2. The use of 2-methylpentanoic acid esters as claimed in Claim 1, characterized in that, in addition to other standard perfume ingredients and other perfumes, the perfume composition as a whole contains from 1 to 50 % by weight of the 2-methylpentanoic acid esters.
3. A process for producing 2-methylpentanoic acid esters corresponding to the following general formula
Figure imgb0027
 in which R is a branched or carbocyclic radical corresponding to the following formula
Figure imgb0028
wherein
R1 = H, CH3
R2 = H, CH3, C2H5
R3 = C2H5, n-C3H7, CH(CH3)2, n-C4H9
with the proviso that only one of the radicals R1, R2 can represent H, or wherein
R1, R2 = (CH2)n, n = 3 or 4
R3 = H,

by esterification of 2-methylpentanoic acid with a branched or carbocyclic alcohol corresponding to the general formula.
EP83710043A 1982-07-07 1983-06-29 2-methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents Expired EP0098791B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83710043T ATE18352T1 (en) 1982-07-07 1983-06-29 2-METHYLPENTAEUR ESTERS WITH A BRANCHED OR CARBOCYCLIC ALCOHOL REST, THEIR PRODUCTION AND USE AS FRAGRANCES.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3225293 1982-07-07
DE19823225293 DE3225293A1 (en) 1982-07-07 1982-07-07 2-METHYL PENTANIC ACID ESTER WITH BRANCHED OR CARBOCYCLIC ALCOHOL RESIDUE, THEIR PRODUCTION AND USE AS A FRAGRANCE

Publications (2)

Publication Number Publication Date
EP0098791A1 EP0098791A1 (en) 1984-01-18
EP0098791B1 true EP0098791B1 (en) 1986-03-05

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EP (1) EP0098791B1 (en)
JP (1) JPS5921645A (en)
AT (1) ATE18352T1 (en)
DE (2) DE3225293A1 (en)
ES (1) ES8403851A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03294400A (en) * 1990-04-13 1991-12-25 Takasago Internatl Corp Perfume composition
EP1889641A1 (en) * 2006-08-18 2008-02-20 Cognis IP Management GmbH Cosmetic compositions containing an ester obtained from 2-ethylbutanol
EP1905419A1 (en) * 2006-09-20 2008-04-02 Cognis IP Management GmbH Cosmetic composition and cosmetic oil substances
JP5080776B2 (en) * 2006-10-06 2012-11-21 花王株式会社 Ester compound
CN102942480B (en) * 2012-11-12 2014-11-19 金溪县鑫润香料实业有限公司 Production process of matricaria ester

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1006848B (en) * 1956-02-07 1957-04-25 Basf Ag Process for the continuous production of acid-free esters of low molecular weight aliphatic carboxylic acids
CH435420A (en) * 1965-06-01 1967-05-15 Bbc Brown Boveri & Cie Stator earth fault protection device for generators in block connection
NL7002359A (en) * 1970-02-19 1971-08-23
US3714236A (en) * 1970-08-07 1973-01-30 Eastman Kodak Co Process for producing mixed esters from aldehydes
CH551361A (en) * 1971-02-26 1974-07-15 Givaudan & Cie Sa PROCESS FOR MANUFACTURING A NEW (ALPHA) METHYL BUTTERIC ACID ESTER.
DE2530227C3 (en) * 1974-07-22 1980-05-29 Int Flavors & Fragrances Inc 2-methyl-substituted pentenoic acid esters, 2-methyl-cis-3-pentenoic acid, and their acid and ester mixtures, their production process and use
US3907718A (en) * 1974-07-22 1975-09-23 Int Flavors & Fragrances Inc 2-Methyl-4-pentenoic acid ester fragrance
DE2626142A1 (en) * 1976-06-11 1977-12-22 Henkel Kgaa USE OF ALIPHATIC 2-METHYL-2-ALKYL ALKANOIC ACID ESTERS AS FRAGRANCE SUBSTANCES AND FRAGRANCE COMPOSITIONS CONTAINING THEM

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
C.R. NOLLER "Lehrbuch der organischen Chemi" 1960 Springer, Seite 230. *

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DE3362425D1 (en) 1986-04-10
JPS5921645A (en) 1984-02-03
ES523902A0 (en) 1984-04-01
DE3225293A1 (en) 1984-01-12
ATE18352T1 (en) 1986-03-15
EP0098791A1 (en) 1984-01-18
ES8403851A1 (en) 1984-04-01

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