EP0098791A1 - 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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EP0098791A1
EP0098791A1 EP83710043A EP83710043A EP0098791A1 EP 0098791 A1 EP0098791 A1 EP 0098791A1 EP 83710043 A EP83710043 A EP 83710043A EP 83710043 A EP83710043 A EP 83710043A EP 0098791 A1 EP0098791 A1 EP 0098791A1
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methylpentanoic acid
ppm
branched
acid esters
mult
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German (de)
French (fr)
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EP0098791B1 (en
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Ulf Armin Dr. Schaper
Klaus Prof. Dr. Bruns
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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 Claisen7 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 smell notes. 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, oral care products, etc., and in tinct 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 3o 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 component nor their special properties are mentioned.
  • 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 remained at 30 ° C. without external cooling.
  • the clear, colorless reaction mixture was mixed with cooling with 16 g lo% sulfuric acid and taken up in 5oo ml ether.
  • the aqueous phase was separated off, the organic phase washed neutral with water, dried and concentrated.

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  • 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)
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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 R1= H, CH3 R 2 =H, CH3, C2H5 R3= C2H5, n-C3H7, CN(CH3)2, n-C4H9 wobei nur einer der Reste R1, R2= H sein kann oder mit R1, R2= (CH2)n, n = 3 oder 4 R 3 = 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
 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 , CN (CH 3 ) 2 , nC 4 H 9 being only one of the residues R 1 , R 2 = H or with R 1 , R 2 = (CH 2 ) n , n = 3 or 4 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 Claisen7 Tischtschenko mit Aluminiumalkoholat als Katalysator unter Disproportionierung des Aldehyds zu Säure und Alkohol, wobei die Komponenten unmittelbar zu dem gewünschten Ester weiterreagieren.The 2-methylpentanoic acid-2-methylpentyl ester can be prepared particularly advantageously from 2-methylpentanal by reaction according to Claisen7 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.

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- 5o Gewichtsprozent. Derartige Kompositionen können zur Parfümierung von kosmetischen Präparaten, wie Cremes, Lotionen, Duftwässern, Aerosolen, Toiletteseifen, Mundpflegemitteln usw., sowie in der Extrait-Parfümerie verwendet werden. Sie können ferner zur Geruchsverbesserung technischer Produkte, wie Wasch- und Reinigungsmittel, Weichspüler,dienen. Es werden etwa o,05 - 2 Gewichtsprozent an Komposition, bezogen auf das gesamte Produkt, eingesetzt.The claimed 2-methylpentanoic acid esters are characterized by interesting floral, fruity, spicy, woody smell notes. 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, oral care products, etc., 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 3o 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 Alkoholkompnente, noch deren besondere Eigenschaften erwähnt.DE-OS 25 3o 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 component, nor their special properties are mentioned.

BeispieleExamples 1. Allgemeine Herstellvorschrift1. General manufacturing instructions

o,1 Mol 2-Methylpentansäure, o,12 Mol verzweigter Alkohol, loo ml Cyclohexan und o,1 g Paratoluolsulfonsäure werden zum Sieden erhitzt. Das freigesetzte Wasser wird azeotrop ausgekreist. Nach beendeter Umsetzung wird das auf Raumtemperatur abgekühlte Reaktionsgemisch zunächst mit lo %iger Natronlauge, danach mit gesättigter Natriumsulfatlösung neutral gewaschen, über Natriumsulfat getrocknet, im Vakuum eingeengt und über eine 2o cm Füllkörperkolonne destilliert. Ausbeute: 7o- 9o % d. Th.0.1 mol of 2-methylpentanoic acid, 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. After the reaction has ended, the reaction mixture, which has cooled to room temperature, is washed first with lo% sodium hydroxide solution, then with saturated sodium sulfate solution, dried over sodium sulfate, concentrated in vacuo and distilled over a 20 cm packed column. Yield: 7o-9o% of theory Th.

Folgende Ester wurden nach dieser allgemeinen Herstellungsvorschrift hergestellt:

  • la) 2-Methylpentansäure-2-pentylester Kp18 86 °C n20 D 1,414 NMR (CC14) δ = 4,85 ppm 1 H mult. 2,3 ppm 1 H mult. Geruch: fruchtig, nach Banane
  • 1b) 2-Metyhlpentansäure-2-methylbutylester Kp18 93 °C n20D 1,419 NMR (CC14) δ =3,85 ppm 2 H dubl. 2,3 ppm 1 H mult. Geruch: Kamille-Note, würzig
  • 1c) 2-Metyhlpentansäure-2-methylpentylester Kp28 113 °C n20 D 1,422 NMR (CDCl3) δ 3,9 ppm 2 H d.dubl. 2,45 ppm 1 H mult. Geruch: Apfelschale-Note, rosig, grün
  • 1d) 2-Methylpentansäure-2-ethylbutylester Kp16 99 °C n20 D 1,425 NMR (CDC13) δ = 4,0 ppm 2 H dubl. 2,45 ppm 1 H mult. Geruch: fruchtig
  • le) 2-Methylpentansäure-2,3-dimethylbutylester Kp21 98 °C n20 D 1,424 NMR (CDCl3) δ = 3,95 ppm 2 H d.dubl: 2,4 ppm 1 H mult. Geruch:würzig
  • lf) 2-Methylpentansäure-2-ethylhexylester Kp16 123 °C n20 D 1,430 NMR (CDCl3) δ=4,0 ppm 2 H d.dubl. 2,45 ppm 1 H mult. Geruch: holzig, Guajak-Note
  • lg) 2-Methylpentansäure-cyclopentylester Kp16 96 °C n20 D 1,438 NMR (CDCl3) δ=5,1 ppm" 1 H mult. 2,4 ppm 1 H mult. Geruch: würzig
  • 1h) 2-Methylpentansäure-cyclohexylester Kp25 120 °C n20D 1,444 NMR (CDCl3) δ=4,8 ppm 1 H mult. 2,4 ppm 1 H mult. Geruch: Rosenoxid-Note
The following esters were produced according to this general manufacturing specification:
  • la) 2-methylpentanoic acid-2-pentyl ester bp 18 86 ° C n 20 D 1.414 NMR (CC1 4 ) δ = 4.85 ppm 1 H mult. 2.3 ppm 1 H mult. Smell: fruity, like banana
  • 1b) 2-methylpentanoic acid-2-methylbutyl ester bp 18 93 ° C n 20 D 1.419 NMR (CC1 4 ) δ = 3.85 ppm 2 H doubl. 2.3 ppm 1 H mult. Smell: Chamomile note, spicy
  • 1c) 2-methylpentanoic acid-2-methylpentyl ester bp 28 113 ° C n 20 D 1.422 NMR (CDCl 3 ) δ 3.9 ppm 2 H d.dubl. 2.45 ppm 1 H mult. Smell: apple skin note, rosy, green
  • 1d) 2-methylpentanoic acid-2-ethylbutyl ester bp 16 99 ° C n 20 D 1.425 NMR (CDC1 3 ) δ = 4.0 ppm 2 H doubl. 2.45 ppm 1 H mult. Smell: fruity
  • le) 2,3-dimethylbutyl 2-methylpentanoate Kp 21 98 ° C n 20 D 1.424 NMR (CDCl 3 ) δ = 3.95 ppm 2 H d.dubl: 2.4 ppm 1 H mult. Odor: spicy
  • lf) 2-methylpentanoic acid-2-ethylhexyl ester bp 16 123 ° C n 20 D 1.430 NMR (CDCl 3 ) δ = 4.0 ppm 2 H d.dubl. 2.45 ppm 1 H mult. Smell: woody, guaiac note
  • lg) 2-methylpentanoic acid cyclopentyl ester bp 16 96 ° C n 20 D 1.438 NMR (CDCl 3 ) δ = 5.1 ppm "1 H mult. 2.4 ppm 1 H mult. Odor: spicy
  • 1h) cyclohexyl 2-methylpentanoate Kp 25 120 ° C n 20 D 1,444 NMR (CDCl 3 ) δ = 4.8 ppm 1 H mult. 2.4 ppm 1 H mult. Smell: Rose oxide note

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

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

Nach Zugabe von ca. 1 g des Alkoholat-Gemisches trat eine exotherme Reaktion ein. Die Reaktionstemperatur wurde durch Kühlung des Kolbens mit Eiswasser unter 4o°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 remained at 30 ° C. without external cooling.

Das klare, farblose Reaktionsgemisch wurde unter Kühlung mit 16 g lo %iger Schwefelsäure versetzt und in 5oo 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 lo% sulfuric acid and taken up in 5oo ml ether. The aqueous phase was separated off, the organic phase washed neutral with water, dried and concentrated.

lo4 g Rohprodukt wurden über eine 2o cm Füllkörperkolonne destilliert und ergaben 81,8 g des gewünschten Esters mit einem Siedepunkt von lo4°C bei 17 mbar.Lo4 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 lo4 ° C at 17 mbar.

3 . Apfel-Komposition Third Apple composition

Figure imgb0003
Figure imgb0003

4. Holz-Base4. Wood base

Figure imgb0004
Figure imgb0004

Claims (5)

1. Verwendung von 2-Methylpentansäureestern der Formel
Figure imgb0005
worin R ein verzweigter oder carbocyclischer Rest der Formel
Figure imgb0006
ist mit R1= H, CH3 R2 = H, CH3, C2H5 R3= C2H5, n-C3H7, CH(CH3)2, n-C 4 H 9 wobei nur einer der Reste R1, R2= H sein kann oder mit R1, R2 = (CH2)n, n = 3 oder 4 R 3 = H als Riechstoffe.1. Use of 2-methylpentanoic acid esters of the formula
Figure imgb0005
 wherein R is a branched or carbocyclic radical of the formula
Figure imgb0006
 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 being only one of the residues R 1 , R 2 = H or with R 1 , R 2 = (CH 2 ) n , n = 3 or 4 R 3 = H as fragrances. 2. Riechstoffkomposition, dadurch gekennzeichnet, daß sie 2-Methylpentansäureester gemäß Anspruch 1 in einer Menge von 1 - 5o Gewichtsprozent, bezogen auf die gesamte Komposition, enthalten.2. Fragrance composition, characterized in that they contain 2-methylpentanoic acid esters according to claim 1 in an amount of 1-5o percent by weight, based on the overall composition. 3. Verfahren zur Herstellung von 2-Methylpentansäureestern des Anspruchs 1 durch Veresterung von 2-Methylpentansäure mit einem der allgmeinen Formel entsprechenden verzweigten oder carbocyclischen Alkohol.3. A process for the preparation of 2-methylpentanoic acid esters of claim 1 by esterification of 2-methylpentanoic acid with a branched or carbocyclic alcohol corresponding to the general formula. 4. Verfahren zur Herstellung von 2-Methylpentansäure-2-methylpentyl- ester durch Umsetzung von 2-Methylpentanal nach Claisen-Tischtschenko mit Aluminiumalkoholat als Katalysator.4. Process for the preparation of 2-methylpentanoic acid-2-methylpentyl ester by reacting Claisen-Tischtschenko's 2-methylpentanal with aluminum alcoholate as catalyst. 5. Neue 2-Methylpentansäureester der Formel
Figure imgb0007
worin R ein verzweigter oder carbocyclischer Rest der Formel
Figure imgb0008
ist,mit R1= H, CH3 R2 = H, CH3, C2H5 R3 = C2H5, n-C3H7, CH(CH3)2, n-C4H9 wobei nur einer der Reste R1, R 2 = H sein kann, oder mit R1, R2 = (CH2)n, n = 3 oder 4 R 3 = H,
mit Ausnahme des 2-Methylpentansäure-2-methylpentylesters.5. New 2-methylpentanoic acid esters of the formula
Figure imgb0007
 wherein R is a branched or carbocyclic radical of the formula
Figure imgb0008
 with R 1 = H, CH3 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 being only one of the residues R 1 , R 2 = H, or with R 1 , R 2 = (CH 2 ) n , n = 3 or 4 R 3 = H ,
with the exception of the 2-methylpentanoic acid-2-methylpentyl ester.
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)

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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

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

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AT (1) ATE18352T1 (en)
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ES (1) ES523902A0 (en)

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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
CN102942480A (en) * 2012-11-12 2013-02-27 金溪县鑫润香料实业有限公司 Production process of matricaria ester

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Publication number Priority date Publication date Assignee Title
JPH03294400A (en) * 1990-04-13 1991-12-25 Takasago Internatl Corp Perfume composition
JP5080776B2 (en) * 2006-10-06 2012-11-21 花王株式会社 Ester compound

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DE2139460A1 (en) * 1970-08-07 1972-03-09 Eastman Kodak Co., Rochester, N.Y. (V.St.A.) Process for the preparation of mixed esters from aldehydes
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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
DE2108805A1 (en) * 1970-02-19 1971-08-26 N V Chemische Fabnek Naarden, Naarden (Niederlande) Process for making a fragrance composition
DE2139460A1 (en) * 1970-08-07 1972-03-09 Eastman Kodak Co., Rochester, N.Y. (V.St.A.) Process for the preparation of mixed esters from aldehydes
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EP1889641A1 (en) * 2006-08-18 2008-02-20 Cognis IP Management GmbH Cosmetic compositions containing an ester obtained from 2-ethylbutanol
WO2008019793A1 (en) * 2006-08-18 2008-02-21 Cognis Ip Management Gmbh Cosmetic compositions containing esters of 2-ethylbutanol
US9079850B2 (en) 2006-08-18 2015-07-14 Cognis Ip Management Gmbh Cosmetic compositions containing esters of 2-ethylbutanol
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CN102942480A (en) * 2012-11-12 2013-02-27 金溪县鑫润香料实业有限公司 Production process of matricaria ester

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ATE18352T1 (en) 1986-03-15
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DE3362425D1 (en) 1986-04-10
EP0098791B1 (en) 1986-03-05
DE3225293A1 (en) 1984-01-12

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