EP0098791B1 - Esters de l'acide 2-méthylpentanoique avec alcools ramifiés ou carbocycliques, leur préparation et leur utilisation comme produits odoriférants - Google Patents

Esters de l'acide 2-méthylpentanoique avec alcools ramifiés ou carbocycliques, leur préparation et leur utilisation comme produits odoriférants 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
Authority
EP
European Patent Office
Prior art keywords
branched
acid esters
methylpentanoic acid
methylpentanoic
following formula
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.)
Expired
Application number
EP83710043A
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German (de)
English (en)
Other versions
EP0098791A1 (fr
Inventor
Ulf Armin Dr. Schaper
Klaus Prof. Dr. Bruns
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT83710043T priority Critical patent/ATE18352T1/de
Publication of EP0098791A1 publication Critical patent/EP0098791A1/fr
Application granted granted Critical
Publication of EP0098791B1 publication Critical patent/EP0098791B1/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
    • C11B9/0007—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.

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

Claims (4)

1. Utilisation d'esters de l'acide 2-méthyl-pentanoïque de formule :
Figure imgb0029
dans laquelle R représente un radical ramifié ou carbocyclique de formule :
Figure imgb0030
où
R1 = H, CH3
R2 = H, CH3, C2H5
R3 = C2H5, n-C3H7, CH(CH3)2, n-C4H9
un seul des radicaux R1, R2 pouvant être = H ou
R1, R2 = (CH2)n, n = 3 ou 4,
R 3 = H,

comme parfums.
2. Composition de parfum, caractérisée en ce qu'elle contient des esters de l'acide 2-méthyl-pentanoïque selon la revendication 1 en une quantité de 1 à 50 % en poids, calculé sur la composition totale.
3. Nouveaux esters de l'acide 2-méthyl-pentanoïque de formule :
Figure imgb0031
dans laquelle R représente un radical ramifié ou carbocyclique de formule :
Figure imgb0032
 où
R1 = H, CH3,
R2 = H, CH3, C2H5,
R3 = C2H5, n-C3H7, CH(CH3)2, n-C4H9,
un seul des radicaux R1, R2 pouvant être = H ou
R1, R2 = (CH2)n, n = 3 ou 4,
R 3 = H,

à l'exception de l'ester 2-méthyl-pentylique de l'acide 2-méthyl-pentanoïque.
4. Procédé de préparation des esters de l'acide 2-méthyl-pentanoïque de la revendication 3 par estérification d'acide 2-méthyl-pentanoïque avec un alcool ramifié ou carbocyclique répondant à la formule générale.
EP83710043A 1982-07-07 1983-06-29 Esters de l'acide 2-méthylpentanoique avec alcools ramifiés ou carbocycliques, leur préparation et leur utilisation comme produits odoriférants Expired EP0098791B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83710043T ATE18352T1 (de) 1982-07-07 1983-06-29 2-methylpentansaeureester mit verzweigtem oder carbocyclischem alkoholrest, deren herstellung und verwendung als riechstoffe.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3225293 1982-07-07
DE19823225293 DE3225293A1 (de) 1982-07-07 1982-07-07 2-methylpentansaeureester mit verzweigtem oder carbocyclischem alkoholrest, deren herstellung und verwendung als riechstoffe

Publications (2)

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

Family

ID=6167785

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83710043A Expired EP0098791B1 (fr) 1982-07-07 1983-06-29 Esters de l'acide 2-méthylpentanoique avec alcools ramifiés ou carbocycliques, leur préparation et leur utilisation comme produits odoriférants

Country Status (5)

Country Link
EP (1) EP0098791B1 (fr)
JP (1) JPS5921645A (fr)
AT (1) ATE18352T1 (fr)
DE (2) DE3225293A1 (fr)
ES (1) ES8403851A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03294400A (ja) * 1990-04-13 1991-12-25 Takasago Internatl Corp 香料組成物
EP1889641A1 (fr) * 2006-08-18 2008-02-20 Cognis IP Management GmbH Compositions cosmétiques contenant un ester obtenu à partir du 2-ethylbutanol
EP1905419A1 (fr) * 2006-09-20 2008-04-02 Cognis IP Management GmbH Composition cosmétique et corps huileux cosmétiques
JP5080776B2 (ja) * 2006-10-06 2012-11-21 花王株式会社 エステル化合物
CN102942480B (zh) * 2012-11-12 2014-11-19 金溪县鑫润香料实业有限公司 一种母菊酯的生产工艺

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1006848B (de) * 1956-02-07 1957-04-25 Basf Ag Verfahren zur kontinuierlichen Herstellung von saeurefreien Estern niedermolekularer aliphatischer Carbonsaeuren
CH435420A (de) * 1965-06-01 1967-05-15 Bbc Brown Boveri & Cie Statorerdschluss-Schutzeinrichtung für Generatoren in Blockschaltung
NL7002359A (fr) * 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 (de) * 1971-02-26 1974-07-15 Givaudan & Cie Sa Verfahren zur herstellung eines neuen (alpha)-methyl-buttersaeureesters.
US3907718A (en) * 1974-07-22 1975-09-23 Int Flavors & Fragrances Inc 2-Methyl-4-pentenoic acid ester fragrance
DE2530227C3 (de) * 1974-07-22 1980-05-29 Int Flavors & Fragrances Inc 2-Methylsubstituierte Pentensäureester, 2-Methyl-cis-3-pentensäure, sowie deren Säure- und Estergemische, deren Herstellungsverfahren und Verwendung
DE2626142A1 (de) * 1976-06-11 1977-12-22 Henkel Kgaa Verwendung von aliphatischen 2-methyl- 2-alkyl-alkansaeureestern als riechstoffe sowie diese enthaltende riechstoffkompositionen

Non-Patent Citations (1)

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

Also Published As

Publication number Publication date
DE3225293A1 (de) 1984-01-12
ES523902A0 (es) 1984-04-01
JPS5921645A (ja) 1984-02-03
ES8403851A1 (es) 1984-04-01
DE3362425D1 (en) 1986-04-10
EP0098791A1 (fr) 1984-01-18
ATE18352T1 (de) 1986-03-15

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