EP0039032A2 - Use of 3,5,5-trimethylhexanoic acid amides as perfuming agents and compositions containing them - Google Patents

Use of 3,5,5-trimethylhexanoic acid amides as perfuming agents and compositions containing them Download PDF

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Publication number
EP0039032A2
EP0039032A2 EP81102990A EP81102990A EP0039032A2 EP 0039032 A2 EP0039032 A2 EP 0039032A2 EP 81102990 A EP81102990 A EP 81102990A EP 81102990 A EP81102990 A EP 81102990A EP 0039032 A2 EP0039032 A2 EP 0039032A2
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EP
European Patent Office
Prior art keywords
trimethylhexanoic acid
acid amides
perfuming agents
compositions containing
trimethylhexanoic
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Withdrawn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
EP81102990A
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German (de)
French (fr)
Other versions
EP0039032A3 (en
Inventor
Hinrich Dr. Möller
Ulf Armin Dr. Schaper
Klaus Dr. Bruns
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication of EP0039032A2 publication Critical patent/EP0039032A2/en
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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
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0092—Heterocyclic compounds containing only N as heteroatom

Definitions

  • 3,5,5-trimethylhexanoic acid amides have the general formula in which R 1 and R 2 independently of one another stand for hydrogen, a .Lower alkyl radical having 1 to 6 carbon atoms or together with the nitrogen atom for a heterocyclic ring, can advantageously be used as fragrances with a fruity or floral odor note.
  • the 3,5,5-trimethylhexanoic acid amides to be used according to the invention are prepared by customary organic chemistry methods by reacting the 3,5,5-trimethylhexanoic acid chloride or the lower esters of 3,5,5-trimethylhexanoic acid with the corresponding amines.
  • the 3,5,5-trimethylhexanoic acid used as starting material is obtained by hydroformylation of diisobutylene with subsequent oxidation of the intermediate product obtained.
  • the mixture of the acids produced in this way is a commercial product under the name "isononanoic acid" and generally contains about 90% of 3,5,5-trimethylhexanoic acid.
  • 3,5,5-Trimethylhexanoic acid amides to be used according to the invention include, for example, 3,5,5-trimethylhexanoic acid amide, -methylamide, -dimethylamide, -methylethylamide, -diethylamide, -dipropylamide, -pyrolidide, -piperidide.
  • 3,5,5-trimethylhexanoic acid amides to be used according to the invention are valuable fragrances with characteristic fruity fragrance notes. A great advantage is their very good ability to combine with fine fruity odor nuances. 3,5,5-Trimethylhexanoic acid dimethylamide is of particular importance here.
  • the 3,5,5-trimethylhexanoic acid amides to be used according to the invention can be mixed with other fragrances in a wide variety of proportions to give new fragrance compositions.
  • the proportion of the 3,5,5-trimethylhexanoic acid amides to be used according to the invention in the fragrance compositions will range from 1 to 50 percent by weight, based on the overall composition.
  • Such compositions can be used directly as perfume or also for perfuming cosmetics such as creams, lotions, fragrant waters, aerosols, toilet soaps, etc. However, they can also be used to improve the smell of technical products such as washing and cleaning agents, disinfectants, textile treatment agents, etc.
  • the preparation was carried out in accordance with the above information using diethylamine as the starting material.
  • the 3,5,5-trimethylhexanoic acid diethylamide obtained has a boiling point of 68 ° C. at 0 , 0 8 mbar and a refractive index 1.4499.
  • Smell Raspberry note.

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

Abstract

The perfuming agents with a fruity or flowery note conform to the formula (I) <IMAGE> where R<1> and R<2> are each independently of the other hydrogen, lower alkyl, (C1-6) or form a heterocyclic ring together with the nitrogen atom. The perfuming agent compositions contain 1-50% by weight of the compounds, preferably the N,N-dimethyl- and -diethyl-substituted 3,5,5-trimethylhexanoamide.

Description

Es wurde gefunden, daß 3,5,5-Trimethylhexansäureamide der allgemeinen Formel

Figure imgb0001
in der R1-und R2 unabhängig voneinander für Wasserstoff, einen .niederen Alkylrest mit 1 bis 6 Kohlenstoffatomen oder zusammen mit dem Stickstoffatom für einen heterocyclischen Ring stehen, in vorteilhafter Weise als Riechstoffe mit einer fruchtigen oder blumigen Geruchsnote verwendet werden können.It has been found that 3,5,5-trimethylhexanoic acid amides have the general formula
Figure imgb0001
 in which R 1 and R 2 independently of one another stand for hydrogen, a .Lower alkyl radical having 1 to 6 carbon atoms or together with the nitrogen atom for a heterocyclic ring, can advantageously be used as fragrances with a fruity or floral odor note.

Die Herstellung der erfindungsgemäß zu verwendenden 3,5,5-Trimethylhexansäureamide erfolgt nach üblichen Methoden der organischen Chemie durch Umsetzung des 3,5,5-Trimethylhexansäurechlorids oder der niederen Ester der 3,5,5-Trimethylhexansäure mit den entsprechenden Aminen. Die als Ausgangsmaterial dienende 3,5,5-Trimethylhexansäure wird durch Hydroformylierung von Diisobutylen mit nachfolgender Oxidation des erhaltenen Zwischenproduktes gewonnen. Das Gemisch der auf diese Weise hergestellten Säuren ist unter dem Namen "Isononansäure" Handelsprodukt und enthält im allgemeinen ca. 90 % an 3,5,5-Trimethylhexansäure. Es kann daher bei der Herstellung der erfindungsgemäß als Riechstoffe zu verwendenden 3,5,5-Trimethylhexansäureamide auch von der handelsüblichen Isononansäure ausgegangen werden, da sich die geringen Mengen an Nebenprodukten bei vielen Anwendungszwecken nicht nachteilig auswirken.The 3,5,5-trimethylhexanoic acid amides to be used according to the invention are prepared by customary organic chemistry methods by reacting the 3,5,5-trimethylhexanoic acid chloride or the lower esters of 3,5,5-trimethylhexanoic acid with the corresponding amines. The 3,5,5-trimethylhexanoic acid used as starting material is obtained by hydroformylation of diisobutylene with subsequent oxidation of the intermediate product obtained. The mixture of the acids produced in this way is a commercial product under the name "isononanoic acid" and generally contains about 90% of 3,5,5-trimethylhexanoic acid. It can therefore be used in the preparation of the 3,5,5-trimethylhexanoic acid amides to be used according to the invention as fragrances commercially available isononanoic acid can also be assumed, since the small amounts of by-products do not have a disadvantageous effect in many applications.

Als erfindungsgemäß zu verwendende 3,5,5-Trimethylhexansäureamide sind zum Beispiel 3,5,5-Trimethylhexansäureamid, -methylamid, -dimethylamid, -methylethylamid, -diethylamid, -dipropylamid, -pyrolidid, -piperidid zu nennen.3,5,5-Trimethylhexanoic acid amides to be used according to the invention include, for example, 3,5,5-trimethylhexanoic acid amide, -methylamide, -dimethylamide, -methylethylamide, -diethylamide, -dipropylamide, -pyrolidide, -piperidide.

Die erfindungsgemäß zu verwendenden 3,5,5-Trimethylhexansäureamide stellen wertvolle Riechstoffe mit charakteristischen fruchtigen Duftnoten dar. Ein großer Vorteil ist ihre sehr gute Kombinationsfähigkeit zu feinen fruchtigen Geruchsnuancen. Eine besondere Bedeutung kommt hierbei dem 3,5,5-Trimethylhexansäure-dimethylamid zu.The 3,5,5-trimethylhexanoic acid amides to be used according to the invention are valuable fragrances with characteristic fruity fragrance notes. A great advantage is their very good ability to combine with fine fruity odor nuances. 3,5,5-Trimethylhexanoic acid dimethylamide is of particular importance here.

Die erfindungsgemäß zu verwendenden 3,5,5-Trimethylhexansäureamide können mit anderen Riechstoffen in den verschiedensten Mengenverhältnissen zu neuen Riechstoffkompositionen gemischt werden. Im allgemeinen wird sich jedoch der Anteil der erfindungsgemäß zu verwendenden 3,5,5-Trimethylhexansäureamide in den Riechstoffkompositionen in den Mengen von 1 bis 5o Gewichtsprozent, bezogen auf die gesamte Komposition, bewegen. Derartige Kompositionen können direkt als Parfüm oder auch zur Parfümierung von Kosmetika wie Cremes, Lotionen, Duftwässern, Aerosolen, Toilettenseifen usw. dienen. Sie können aber auch zur Geruchsverbesserung technischer Produkte wie Wasch- und Reinigungsmittel, Desinfektionsmittel, Textilbehandlungsmittel usw. eingesetzt werden.The 3,5,5-trimethylhexanoic acid amides to be used according to the invention can be mixed with other fragrances in a wide variety of proportions to give new fragrance compositions. In general, however, the proportion of the 3,5,5-trimethylhexanoic acid amides to be used according to the invention in the fragrance compositions will range from 1 to 50 percent by weight, based on the overall composition. Such compositions can be used directly as perfume or also for perfuming cosmetics such as creams, lotions, fragrant waters, aerosols, toilet soaps, etc. However, they can also be used to improve the smell of technical products such as washing and cleaning agents, disinfectants, textile treatment agents, etc.

Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch hierauf zu beschränken.The following examples are intended to explain the subject matter of the invention in more detail, but without restricting it thereto.

BeispieleExamples

Zunächst wird die Herstellung der erfindungsgemäß zu verwenden 3,5,5-Trimethylhexansäureamide näher beschrieben.The preparation of the 3,5,5-trimethylhexanoic acid amides to be used according to the invention is first described in more detail.

1.) 3,5,5-Trlmethylhexansäure-dimethylamld1.) 3,5,5-Trlmethylhexanoic acid dimethylamld

Zu 128 g einer 4o %igen Lösung von Dimethylamin in Wasser wurden unter Rühren bei Raumtemperatur 4o g 3,5,5-Trimethylhexansäurechlorid getropft. Nach 2- stündigem Rühren wurde mit Wasser verdünnt, das entstandene 3,5,5-Trimethylhexansäuredimethylamid mit Ether aus der wäßrigen Lösung extrahiert, die Etherphase mit verdünnter Salzsäure, verdünnter Sodalösung und dann mit Wasser gewaschen. Nach dem Abdestillieren des Ethers wurde der Rückstand fraktioniert destilliert. Es wurden 35,7 g, das sind 85 % der Theorie, an 3,5,5-Trimethylhexansäuredimethylamid vom Siedepunkt 93° C bei o,2o mbar und dem 20 Brechungsindex nD 1,4482 erhalten.
Geruch: Erdbeer-, Himbeer-Note.4o g of 3,5,5-trimethylhexanoic acid chloride were added dropwise to 128 g of a 40% solution of dimethylamine in water while stirring at room temperature. After stirring for 2 hours, the mixture was diluted with water, the resulting 3,5,5-trimethylhexanoic acid dimethylamide was extracted from the aqueous solution with ether, the ether phase was washed with dilute hydrochloric acid, dilute sodium carbonate solution and then with water. After the ether had been distilled off, the residue was fractionally distilled. 35.7 g, which is 85% of theory, of 3,5,5-trimethylhexanoic acid dimethylamide having a boiling point of 93 ° C. at 0.2 mbar and the refractive index nD 1.4482 were obtained.
Smell: strawberry, raspberry note.

2.) 3,5,5-Trimethylhexansäure-diethylamid2.) 3,5,5-Trimethylhexanoic acid diethylamide

Die Herstellung erfolgte entsprechend vorstehenden Angaben unter Einsatz von Diethylamin als Ausgangsmaterial. Das erhaltene 3,5,5-Trimethylhexansäure-diethylamid besitzt einen Siedepunkt von 68° C bei 0,08 mbar und einen Brechungsindex

Figure imgb0002
1,4499. Geruch: Himbeer-Note.The preparation was carried out in accordance with the above information using diethylamine as the starting material. The 3,5,5-trimethylhexanoic acid diethylamide obtained has a boiling point of 68 ° C. at 0 , 0 8 mbar and a refractive index
Figure imgb0002
 1.4499. Smell: Raspberry note.

Erdbeer-KomplexStrawberry complex

Figure imgb0003
Figure imgb0003

Claims (5)

1. Verwendung von 3,5,5-Trimethylhexansäureamiden der allgemeinen Formel
Figure imgb0004
in der R1 und R2 unabhängig voneinander für Wasserstoff, einen niederen Alkylrest mit 1 bis 6 Kohlenstoffatomen oder zusammen mit dem Stickstoffatom für einen heterocyclischen Ring stehen, als Riechstoffe.1. Use of 3,5,5-trimethylhexanoic acid amides of the general formula
Figure imgb0004
 in which R 1 and R 2 independently of one another represent hydrogen, a lower alkyl radical having 1 to 6 carbon atoms or together with the nitrogen atom for a heterocyclic ring, as fragrances. 2. Riechstoffkompositionen, gekennzeichnet durch einen Gehalt an 3,5,5-Trimethylhexansäureamiden nach Anspruch 1.2. Fragrance compositions, characterized by a content of 3,5,5-trimethylhexanoic acid amides according to claim 1. 3. Riechstoffkompositionen nach Anspruch 2, dadurch gekennzeichnet, daß sie die 3;5,5-Trimethylhexansäureamide in einer Menge von 1 bis 5o Gewichtsprozent, bezogen auf die gesamte Komposition enthalten.3. Fragrance compositions according to claim 2, characterized in that they contain the 3; 5,5-trimethylhexanoic acid amides in an amount of 1 to 5o percent by weight, based on the entire composition. 4. 3,5,5-Trimethylhexansäure-dimethylamid.4. 3,5,5-trimethylhexanoic acid dimethylamide. 5. 3,5,5-Trimethylhexansäure-diethylamid.5. 3,5,5-trimethylhexanoic acid diethylamide.
EP81102990A 1980-04-28 1981-04-18 Use of 3,5,5-trimethylhexanoic acid amides as perfuming agents and compositions containing them Withdrawn EP0039032A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3016288 1980-04-28
DE19803016288 DE3016288A1 (en) 1980-04-28 1980-04-28 USE OF 3,5,5-TRIMETHYLHEXANIC ACID AMIDES AS A RICHING MATERIAL AND THESE CONTAINING RICHSTOFFPOSITIONEN

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EP0039032A2 true EP0039032A2 (en) 1981-11-04
EP0039032A3 EP0039032A3 (en) 1982-09-15

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JP (1) JPS56169661A (en)
BR (1) BR8102535A (en)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5143900A (en) * 1989-05-19 1992-09-01 Colgate-Palmolive Company Perfumes containing N-lower alkyl neoalkanamide (s)
WO2016156075A1 (en) * 2015-03-31 2016-10-06 Basf Se Composition comprising a pesticide and isononanoic acid n,n-dimethyl amide

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1572332A (en) * 1968-04-05 1969-06-27
GB2010678A (en) * 1977-12-23 1979-07-04 Henkel Kgaa Perfume ingredients and perfume compositions consisting of or containing 3,5,5-trimethylhexanoic acid esters
EP0017604A1 (en) * 1979-04-02 1980-10-15 Rhone-Poulenc Specialites Chimiques Process for producing perfuming compositions and perfumed products, and compositions and products so obtained

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1572332A (en) * 1968-04-05 1969-06-27
GB2010678A (en) * 1977-12-23 1979-07-04 Henkel Kgaa Perfume ingredients and perfume compositions consisting of or containing 3,5,5-trimethylhexanoic acid esters
EP0017604A1 (en) * 1979-04-02 1980-10-15 Rhone-Poulenc Specialites Chimiques Process for producing perfuming compositions and perfumed products, and compositions and products so obtained

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5143900A (en) * 1989-05-19 1992-09-01 Colgate-Palmolive Company Perfumes containing N-lower alkyl neoalkanamide (s)
WO2016156075A1 (en) * 2015-03-31 2016-10-06 Basf Se Composition comprising a pesticide and isononanoic acid n,n-dimethyl amide
US10463040B2 (en) 2015-03-31 2019-11-05 Basf Se Composition comprising a pesticide and isononanoic acid N,N-dimethyl amide
AU2016239537B2 (en) * 2015-03-31 2020-02-06 Basf Se Composition comprising a pesticide and isononanoic acid N,N-dimethyl amide
RU2723035C2 (en) * 2015-03-31 2020-06-08 Басф Се Composition containing pesticide and n,n-dimethylamide of isononanoic acid

Also Published As

Publication number Publication date
DE3016288A1 (en) 1981-11-12
EP0039032A3 (en) 1982-09-15
JPS56169661A (en) 1981-12-26
BR8102535A (en) 1982-01-05

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