DE2108805A1 - Process for making a fragrance composition - Google Patents

Process for making a fragrance composition

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Publication number
DE2108805A1
DE2108805A1 DE19712108805 DE2108805A DE2108805A1 DE 2108805 A1 DE2108805 A1 DE 2108805A1 DE 19712108805 DE19712108805 DE 19712108805 DE 2108805 A DE2108805 A DE 2108805A DE 2108805 A1 DE2108805 A1 DE 2108805A1
Authority
DE
Germany
Prior art keywords
fragrance
methylene
dimethylhexanol
fragrance composition
making
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.)
Pending
Application number
DE19712108805
Other languages
German (de)
Inventor
Auf Nichtnennung Antrag
Original Assignee
N V Chemische Fabnek Naarden, Naarden (Niederlande)
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 N V Chemische Fabnek Naarden, Naarden (Niederlande) filed Critical N V Chemische Fabnek Naarden, Naarden (Niederlande)
Publication of DE2108805A1 publication Critical patent/DE2108805A1/en
Pending legal-status Critical Current

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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
    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

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)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Fats And Perfumes (AREA)

Description

DlPL-INQ. DIETER JANDER DR.-INQ. MANFRED BÖNINQDlPL-INQ. DIETER JANDER DR.-INQ. MANFRED BÖNINQ

Patentanwälte Zustelladresse:Patent attorneys delivery address:

reply to:reply to:

8MONCHENeO(BOGENHAUSEN) 1 BERLI N 33 (D AHLEM)8MONCHENeO (BOGENHAUSEN) 1 BERLI N 33 (D AHLEM)

KOLBERGER STRASSE 21 HOTTENWEG 15KOLBERGER STRASSE 21 HOTTENWEG 15

Telefon: 08 11/48 27 04 Telefon: 03 11/76 13 03Phone: 08 11/48 27 04 Phone: 03 11/76 13 03

Telegramme: Consideration BerlinTelegrams: Consideration Berlin

12. Februar 1971 97/13 546 DEFebruary 12, 1971 97/13 546 DE

Patentanmeld u η gPatent application u η g

der Firmaof the company

N. V. CHEMISCHE FABRIEK "NAAEDEN" Naarden/NiederlandeN. V. CHEMICAL FACTORY "NAAEDEN" Naarden / Netherlands

"Verfahren zur Herstellung einer Duftstoffzusammensetzung""Process for the preparation of a fragrance composition"

Die Erfindung betrifft ein Verfahren zur Herstellung von Duftstoff zusammensetzungen und parfümierten Artikeln, die einen oder mehrere Ester von 3-Methylen-5,5-dimethylhexanol-l als Duftstoff neben anderen hierfür verwendungsfähigen Bestandteilen enthalten. jThe invention relates to a method for producing fragrance compositions and perfumed articles that contain one or more esters of 3-methylene-5,5-dimethylhexanol-1 as a fragrance in addition to other components that can be used for this purpose. j

Die Herstellung der erfindungsgemäss verwendbaren Substanzen ist literaturbekannt (vgl. britisches Patent 657.497; J.Am.Chem. Soc. J±t 4o73 (1952); J.Am.Chem.Soc. 22» 4666 (1955); U.S.-Patent 2.335.027; Chemical Reviews £1, 533 (1952) und Yakagaku 1£, 21o (1966) (vgl. Chem. Abstr. 6£, 2114e (1966)).The preparation of the substances which can be used according to the invention is known from the literature (cf. British Patent 657,497; J. Am. Chem. Soc. J ± t 4073 (1952); J. Am. Chem. Soc. 22 »4666 (1955); US Patent 2,335 .027; Chemical Reviews £ 1, 533 (1952) and Yakagaku £ 1, 21o (1966) (cf. Chem. Abstr. 6 £, 2114e (1966)).

Zur Herstellung des Formiates kann man von Diisobutylen, Paraformaldehyd und einer Mischung aus Ameisensäure und EssigsäurQii ausgehen.The formate can be prepared from diisobutylene, paraformaldehyde and a mixture of formic acid and acetic acid Qii .

«f M -2- «F M -2-

10 9 8 3 5/116910 9 8 3 5/1169

Postscheckkonto Berlin Weit 1743 84 B.rllner Bank AG., Depositenkasse 1 Postscheckkonto Berlin Weit 1743 84 B.rllner Bank AG., Depositenkasse 1

DIPL.-INg. DIETER JANDER DR.-1NQ. MANFRED BONINQ 2108 8 05DIPL.-INg. DIETER JANDER DR.-1NQ. MANFRED BONINQ 2108 8 05

PATENTANWÄLTEPATENT LAWYERS

-2--2-

Falls gewünscht, können die anderen Ester auch am 3-Methylen-5,5-dimethylhexanol-l und den entsprechenden Säuren, Säureanhydriden oder Säurechloriden hergestellt werden.If desired, the other esters can also be attached to 3-methylene-5,5-dimethylhexanol-l and the corresponding acids, acid anhydrides or acid chlorides.

In der oben genannten britischen Patentschrift Nr. 657.497 ist die Verwendung als Lösungsmittel für Lacke, Parfüme und ähnliches für eine Reihe dieser Substanzen als mögliche Verwendbarkeit sowie die Verwendung als Zwischenprodukte angegeben worden (siehe Seite 4, Zeilen 4-6). Es ist jedoch nichts über eine eigene Duftstoffwirkung der Substanzen ausgesagt. Darüber hinaus ist es offensichtlich, dass Stoffe, die einen starken eigenen Duft besitzen, sich nur sehr schlecht als Lösungsmittel für Duftstoffe eignen, wie es behauptet wurde.In the above-mentioned British Patent No. 657,497, use as a solvent for paints, perfumes and the like is disclosed for a number of these substances have been given as possible usability and use as intermediates (see page 4, lines 4-6). However, nothing is said about the substances' own fragrance effects. Furthermore It is obvious that substances that have a strong scent of their own turn out to be very bad solvents Fragrances are suitable, as has been claimed.

Überraschenderweise wurde nun gefunden, dass die oben genannten Ester sich sehr gut für die Verwendung als Duftstoffe eignen und verschiedenen Duftstoffzusammensetzungen einen blumenartigen, holzartigen oder fruchtartigen Geruch verleihen.Surprisingly, it has now been found that the abovementioned esters are very suitable for use as fragrances and various fragrance compositions a flower-like, give a woody or fruity odor.

Nachfolgend werden weitere Angaben über den Charakter einiger der Substanzen als Duftstoffe gemacht, die erfindungsgemäss verwindet werden können.In the following, further details are given about the character of some of the substances as fragrances which are twisted according to the invention can be.

Ester des 3-Methylen-5i5- Beschreibung des Duftes dime thylhexanoIs-IEster of 3-methylene-5i5- Description of the fragrance dimethylhexanoIs-I

Formiat minzartig,frisch-blumenartig, irisFormate mint-like, fresh flower-like, iris

ähnlichsimilar

Icetat blumenartig-holzartig, irisähnlichIcetat flower-like-wood-like, iris-like

Propionat frische Bergamotte, etwas kamillenPropionate fresh bergamot, some chamomile

ähnlichsimilar

Butyrat Jasmin, blumenartig-fruchtartigButyrate jasmine, flower-like-fruity

Isobutyrat fruchtartig, blumenartig, ylang-Isobutyrate fruity, flower-like, ylang-

ylang-ähnli chylang-like

ot-Methylbutyrat fruchtartig-holzartig, frischerot-methylbutyrate fruity-woody, fresher

ApfelgeruchApple smell

Benzoat schwach blumenartig, farnesolähn-Benzoate slightly flower-like, farnesol-like

lichlich

Einige physikalische Konstanten und NMR-Daten sind in der folgenden Tabelle angegeben. Some physical constants and NMR data are given in the table below.

"3" 109835/1169 " 3 " 109835/1169

Tabelle.Tabel.

I II I

ι { ι ιι { ι ι

OHOH

3i3i

Ester des 3-Methylen-5, 5-dimethylhexanols-l H-C - 0 - OH9- C -1OH9,-Ester of 3-methylene-5, 5-dimethylhexanol-1 HC - 0 - OH 9 - C - 1 OH 9 , -

OHOH

31 3 1

OH2 OH 2

!~ ι b ! ~ ι b

-G-R-G-R

ι b ι cc'|ά ι e ιι b ι cc '| ά ι e ι

CDCD COCO coco cncn

toto

S?S?

ir er»ir he »

EsterEster Siedepunkt
°c/mm Hg boiling point
° c / mm Hg « 2o
n Ώ « 2o
n Ώ NMR-SpektrumNMR spectrum aa bb cc1 cc 1 dd ee SäurerestAcid residue FormiatFormate 82,50Ao mm82.5 0 Ao mm o,9o/s/9o.9o / s / 9 1.93/S/21.93 / S / 2 439/m/l
4,9o/m/l ' 439 / m / l
4.9o / m / l ' 2,35/t/22.35 / t / 2 4,2o/t/24.2o / t / 2 7,94/S/l
I7.94 / S / l
I. Acetatacetate 94°/lo mm94 ° / lo mm 1,43971.4397 o,89/S/9o, 89 / S / 9 1.91/S/21.91 / S / 2 4,83/m/l
4,86/m/l4.83 / m / l
4.86 / m / l 2,29/t/22.29 / t / 2 4,o6/t/24, o6 / t / 2 überschnei
det sich mit
bsnow over
det yourself with
b PropionatPropionate Io4°/lo mmIo4 ° / lo mm 1,43691.4369 O.92/S/9O.92 / S / 9 1.94/S/21.94 / S / 2 4,TB/m/l
4,89/m/l4, TB / m / l
4.89 / m / l 2.33A/22.33A / 2 4,o9/t/24, o9 / t / 2 2,22/q/2; ..
l,lo/t/3 W2.22 / q / 2; ..
l, lo / t / 3 W. ButyratButyrate 1120Ao mm112 0 Ao mm 1,43821.4382 o,9l/s/9o, 9l / s / 9 l,94/s/2l, 94 / s / 2 4,78/m/l
4,9o/m/l4.78 / m / l
4.9o / m / l 2,33/t/22.33 / t / 2 4,lo/t/24, lo / t / 2 l!o7/t/3*l! o7 / t / 3 * IsobutyratIsobutyrate Io8,5°/lommIo 8.5 ° / lomm I,44o6I, 44o6 O.91/S/9O.91 / S / 9 1.93/S/21.93 / S / 2 4,77/m/l
4,89/m/l4.77 / m / l
4.89 / m / l 2,32/t/22.32 / t / 2 4,lo/t/24, lo / t / 2 ■IB *
l,12/d/6 ■ IB *
l, 12 / d / 6 ^-Methyl-
butyrat^ -Methyl-
butyrate 118°/lo mm118 ° / lo mm 1,43851.4385 O.92/S/9O.92 / S / 9 1.94/S/21.94 / S / 2 4,77/m/l
4,89/m/l4.77 / m / l
4.89 / m / l 2,33/t/22.33 / t / 2 4,lo/t/24, lo / t / 2 ; i,o7; i, o7 BenzoatBenzoate 125°/1 mm125 ° / 1 mm 1,44121.4412 o,91/S/9o, 91 / S / 9 l,97/S/2l, 97 / S / 2 4,79/m/l
4,95/m/l4.79 / m / l
4.95 / m / l 2.45A/22.45A / 2 4.35A/24.35A / 2 I,5o22I, 5o22

roro

CD OO OO OCD OO OO O cncn

DIPL..INQ. DIETERJANDER DR.-INQ. MANFRED BONINODIPL..INQ. DIETERJANDER DR.-INQ. MANFRED BONINO PATENTANWÄLTEPATENT LAWYERS

-4--4-

Die folgenden Beispiel zeigen einige Anwendungen der erfindungsgemässen Verbindungen in Parfüm-Zusammensetzungen, wodurch der blumenartige Charakter dieser Zusammensetzungen verstärkt wird:The following examples show some applications of the invention Compounds in perfume compositions, whereby the floral character of these compositions is enhanced:

Beispiel 1example 1

Parfüm-Zusammensetzung mit Veilchen-CharakterPerfume composition with a violet character

Bestandteil:Component:

Methylheptincarbonat lofo in Diäthylphthalat ot-Methyljonon jf-Me thyl j onon Ylang-Ylang-Öl I Benzylacetat oi--Hexylzimtaldehyd Zitronellal Phenyläthanol Hydroxyzitronellal Bergamottöl Heliotropin MoschusketonMethylheptine carbonate lofo in diethyl phthalate ot-methyljonon jf-methyl jonon ylang-ylang oil I benzyl acetate oi - hexylcinnamaldehyde citronellal phenylethanol hydroxycitronellal bergamot oil heliotropin musk ketone

Acetat des 3-Methylen-5,5-dimethylhexanols-1 3-methylene-5,5-dimethylhexanol-1 acetate

Beispiel 2 Jasminduftstoff für SeifeExample 2 Jasmine fragrance for soap

Bestandteil:Component:

Benzylacetat 06-Amylzimtaldehyd Methylanthramilat 1ο?έ in DiäthylphthalatBenzyl acetate 06-amylcinnamaldehyde Methyl anthramilate 1ο? Έ in diethyl phthalate

sogenannter Aldehyd C 14 lo% in Diäthylphthalatso-called aldehyde C 14 lo% in diethyl phthalate

sogenannter Aldehyd C 16 1$ in Diäthylphthalatso-called aldehyde C 16 1 $ in Diethyl phthalate

Terpineol Geraniumöl Bourbon Phenyläthanol Gewichtsteile:Terpineol Geranium Oil Bourbon Phenylethanol parts by weight:

4o 3oo 26o 3o 5o 4o 60 4o 2o 3o 3o 2o4o 3oo 26o 3o 5o 4o 60 4o 2o 3o 3o 2o

8080

10001000

Gewichtsteile: 2oo 80 4oParts by weight: 2oo 80 4o

2o2o

2o 9o 3o2o 9o 3o

15o15o

10 9 8 3 5/1169 -5-10 9 8 3 5/1169 -5-

DIPL.-INQ. DIETER JANDER DR.-I NQ. MANFRED BONINQDIPL.-INQ. DIETER JANDER DR.-I NQ. MANFRED BONINQ

PATENTANWÄLTEPATENT LAWYERS

-5--5-

HydroxycitronellalHydroxycitronellal 6o6o 'i -Me thyl j onon 'i -Me thyl j onon 3o3o HeliotropinHeliotropin 3o3o ZimtalkoholCinnamon alcohol 4o4o Tri chlorine thylphenylcarbiny lace tatTri chlorine thylphenylcarbiny lace tat IoIo 11-oxahexadecanolid11-oxahexadecanolide IoIo MoschusambretteMusk ambrette 2o2o Indol lo# in DiäthylphthalatIndole lo # in diethyl phthalate 2o2o Isojasmon lo% in DiäthylphthalatIsojasmone lo% in diethyl phthalate 3o3o Buttersäureester des 3-Methylen-5,5-
dime thylhexariDls-1Butyric acid ester of 3-methylene-5,5-
dime thylhexariDls-1 12o12o looolooo Beispiel 3Example 3 Parfümzusammenaetzung mit rosenartigemPerfume composition with rose-like Charaktercharacter Bestandteil:Component: GewichtsteileParts by weight Aldehyd C 9Aldehyde C 9 2o2o Aldehyd G 11Aldehyde G 11 55 PhenyläthanolPhenylethanol 29o29o Phenyläthylac e tatPhenyläthylac e did 6o6o GeraniolGeraniol 17o17o CitronellylacetatCitronellyl acetate 7o7o Phenylacetaldehyd-dimethylacetalPhenyl acetaldehyde dimethyl acetal IoIo Linalylac e tatLinalylac e did 3o3o Geraniumöl BourhonGeranium Oil Bourhon 8o8o HydroxycitronellalHydroxycitronellal IoIo EugenolEugenol 55 GruajakbaumholzölGruajak tree wood oil 2o2o TrichlormethylphenylcarbinylacetatTrichloromethylphenylcarbinylacetate IoIo MoschusambretteMusk ambrette IoIo MoschusketonMusk ketone IoIo Benzoesäureester des 3-Methylen-5f5-
dimethylhexanols-1Benzoic acid ester of 3-methylene-5 f 5-
dimethylhexanols-1 2oo2oo looolooo

DJ:WK:BFDJ: WK: BF

109835/1169109835/1169

Claims (3)

PatentansprücheClaims 1) Verfahren zur Herstellung von Duftstoffzusammensetzungen, dadurch gekennzeichnet, dass einer oder mehrere Ester des 3-Methylen-5,5-dimethylhexanols-l in für diesen Zweck übliche Zusammensetzungen gebracht werden.1) Process for the preparation of fragrance compositions, characterized in that one or more esters of 3-methylene-5,5-dimethylhexanol-l in for this Purpose customary compositions are brought. 2) Verfahren zur Herstellung parfümierter Artikel, dadurch gekennzeichnet, dass wenigstens ein Ester des 3-Methylen-5,5-dimethylhexanols-l als Duftstoff in die Artikel gebracht wird.2) Process for the production of perfumed articles, characterized in that at least one ester of the 3-methylene-5,5-dimethylhexanol-l is brought into the articles as a fragrance. 3) Parfümierte Artikel, erhalten gemäss Anspruch 2.3) Perfumed articles obtained according to claim 2. fiß Duftstoffzusammensetzung enthaltend einen oder mehrere Ester des 3-Methylen-5,5"dimethylhexan.ols-l als Duftstoff. A fragrance composition containing one or more esters of 3-methylene-5,5 "dimethylhexan.ol-1 as a fragrance. 109835/1169109835/1169 Postscheckkonto Berlin West 1743 84 Berliner Bank AG, Depositenkasse 1Postal checking account Berlin West 1743 84 Berliner Bank AG, Deposit kasse 1
DE19712108805 1970-02-19 1971-02-12 Process for making a fragrance composition Pending DE2108805A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL7002359A NL7002359A (en) 1970-02-19 1970-02-19

Publications (1)

Publication Number Publication Date
DE2108805A1 true DE2108805A1 (en) 1971-08-26

Family

ID=19809374

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19712108805 Pending DE2108805A1 (en) 1970-02-19 1971-02-12 Process for making a fragrance composition

Country Status (3)

Country Link
DE (1) DE2108805A1 (en)
FR (1) FR2080628A1 (en)
NL (1) NL7002359A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4384007A (en) 1981-07-06 1983-05-17 International Flavors & Fragrances Inc. Use in flavors of Prins reaction products of diisobutylene
DE3245047A1 (en) * 1981-12-07 1983-06-09 Firmenich S.A., 1211 Genève ALIPHATIC ALCOHOLS AND ESTERS AND THEIR USE AS PERFUME COMPONENTS
US4399063A (en) * 1981-07-06 1983-08-16 International Flavors & Fragrances Inc. Prins reaction products of diisobutylene, derivatives thereof, organoleptic uses thereof and processes for preparing same
US4406810A (en) 1981-07-06 1983-09-27 International Flavors & Fragrances Inc. Use of Prins reaction products of diisobutylene in augmenting or enhancing the aroma of detergents
EP0098791A1 (en) * 1982-07-07 1984-01-18 Henkel Kommanditgesellschaft auf Aktien 2-Methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents
US4437476A (en) 1981-07-06 1984-03-20 International Flavors & Fragrances Inc. Prins reaction products of diisobutylene, derivatives thereof, organoleptic uses thereof and processes for preparing same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4384007A (en) 1981-07-06 1983-05-17 International Flavors & Fragrances Inc. Use in flavors of Prins reaction products of diisobutylene
US4399063A (en) * 1981-07-06 1983-08-16 International Flavors & Fragrances Inc. Prins reaction products of diisobutylene, derivatives thereof, organoleptic uses thereof and processes for preparing same
US4406810A (en) 1981-07-06 1983-09-27 International Flavors & Fragrances Inc. Use of Prins reaction products of diisobutylene in augmenting or enhancing the aroma of detergents
US4437476A (en) 1981-07-06 1984-03-20 International Flavors & Fragrances Inc. Prins reaction products of diisobutylene, derivatives thereof, organoleptic uses thereof and processes for preparing same
DE3245047A1 (en) * 1981-12-07 1983-06-09 Firmenich S.A., 1211 Genève ALIPHATIC ALCOHOLS AND ESTERS AND THEIR USE AS PERFUME COMPONENTS
US4525298A (en) * 1981-12-07 1985-06-25 Firmenich Sa Aliphatic alcohols and esters and their use as perfuming ingredients
EP0098791A1 (en) * 1982-07-07 1984-01-18 Henkel Kommanditgesellschaft auf Aktien 2-Methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents

Also Published As

Publication number Publication date
NL7002359A (en) 1971-08-23
FR2080628A1 (en) 1971-11-19

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