DE501627C - Process for the production of fragrance mixtures - Google Patents

Process for the production of fragrance mixtures

Info

Publication number
DE501627C
DE501627C DEI38415D DEI0038415D DE501627C DE 501627 C DE501627 C DE 501627C DE I38415 D DEI38415 D DE I38415D DE I0038415 D DEI0038415 D DE I0038415D DE 501627 C DE501627 C DE 501627C
Authority
DE
Germany
Prior art keywords
parts
oxo
cyclohexane
production
oil
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
DEI38415D
Other languages
German (de)
Inventor
Dr Angelo Knorr
Dr Albert Weissenborn
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI38415D priority Critical patent/DE501627C/en
Priority to NL27877D priority patent/NL27877C/xx
Application granted granted Critical
Publication of DE501627C publication Critical patent/DE501627C/en
Expired legal-status Critical Current

Links

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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
    • C07C47/11—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings monocyclic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Description

Verfahren zur Herstellung von Riechstoffmischungen Die durch Hydrieren von jonone-n erhältlichen Tetrahydrojonone besitzen einen jenen zwar ähnlichen, aber technisch nicht wertvolleren oder gar neuartigen Geruch. Auch der einzige bekannte Aldehyd,der jononreihe, das i, i, 3: - Trimet'hyl-2-[23-oxo - 2° - methopropen-(2i)-yl-]cyclohexen-(2), ist im Geruch den Jononen ähnlich, im übrigen aber unbeständiger.Process for the production of fragrance mixtures by hydrogenation Tetrahydrojonons available from jonone-n have a similar one, but technically not more valuable or even novel odor. Also the only known one Aldehyde, the ionone series, the i, i, 3: - trimethyl-2- [23-oxo - 2 ° - methopropen- (2i) -yl-] cyclohexene (2), is similar in smell to the ionons, but otherwise less stable.

Hiernach war von gesättigten Verbindungen, die den ungesättigten Aldehyden der Jononreihe entsprechen, ein abweichendes Verhalten nicht zu erwarten.After that it was of saturated compounds, the unsaturated aldehydes correspond to the ionic series, no deviating behavior is to be expected.

Wie nun gefunden: wurde, zeichnen sich 24-Oxo-23-alkylbutylcyclohexan und seine Kernsubstitutionsprodukte durch einen überraschend neuartigen Geruch aus, der vom jonongeruch vollständig verschieden ist und eine angenehm bittere, gleichzeitig nuß- und laubartige Note besitzt. Dieser Geruchscharakter macht die Verbindungen wertvoll zur Erzielung besonderer blumiger Effekte in. Blütenölen und zum Aufbau ganz neuer Phantasiegerüche.As has now been found: 24-Oxo-23-alkylbutylcyclohexane are distinguished and its core substitution products are characterized by a surprisingly new smell that is completely different from the jonon smell and has a pleasantly bitter, at the same time nut and leafy note. This odor character makes the compounds valuable for achieving special flowery effects in flower oils and for building up completely new fantasy smells.

Beispielsweise seien genannt: [q.-0x0-3-methobutyl-]cyclohexan, farblose Flüssigkeit, K. P. 98 bis i oo°, 5 mm, i, 5 - Dimethyl - 12 - [24-oxo - 23 - methobu;tyl; ] cyclohexan, farb'_ose Flüssigkeit, K. P. i 12 bis 114', 3 mm, 3,4,6-Trimethyl -2- [24-OXO- 23 - methobutyl-] cyclohexan, farblose Flüssigkeit, K. P. 115 bis 117°, 3 mm, q.-Methyl-5-isopropyl-2-[24-oxo-z -methobutyl-]cyclohexan, farblose Flüssigkeit, K. P. 128 bis 130°, 4 mm, Die in Frage kommenden, bisher unbekannten Aldehyde lassen sich nach bekannten Verfahren zur Darstellung von Aldehyden gewinnen, z. B. aus Aden um ein Kohlenstoffatom ärmeren Ketonen durch Kondensation. mii Halogenessigsäureestern nach dem Verfahren des Patents 17q.279 und! Spaltung der so erhältlichen Glycidsäuren gemäß Patentschrift 17q.239. Beispiel i Phantasieparfüm-Grundlage: 2o Teile 1,1,3-Trimeihyl-2-[24-oxo-23- methobutyl-]cyclohexan, 5 - Jonon, i o - Methyl j onon, 8 - Ylang-Ylang-C51, 5 - künstl. Jasminöl, :1. - Heliotropin, 8 - Cumarin, i o - Phenyläthylalkohol, 15 - Bergamottöl, 5 - Pomeranzenöl, 5 - ostindisches Sandelholzöl, 5 - Moschus-Ambrette, ioo Teile. Beispiel e Blütenöl-Grundlage: 6 Teile -1,I,3-Trimethyl-2-[24-oxo-23- äthobutyl-]cyclohexan, 35 - Hydroxycitronellal, 26 - Benzylalkohol, 1 o - Benzylacetat, io - Phenyläthylalkohol, io - Zimtalkohol, 3 - Ylang-Ylang-Öl, ioo Teile. Beispiel l3. Maiglöckchen-Seifenparfüm: 7 Teile [4.-Oxo-3-methObutyl-1cYclo- hexan, 30 - Linaloeöl, 2o - Iiydroxycitronellal, I o - Canang aöl, 3 - Benzaldehyd, 2o - Terpineol, io - Benzylacetat, ioo Teile. Beispiel¢ Jasminöl: io Teile I,5-Dimethyl-2-[24--Oxo-23- methobutyl-]cyclohexan, 35 - Benzylacetat, q.o - Benzylalkohol, 5 - Linalool, 5 - Linalylacetat, 5 - Anthranilsäuremethylester, ioo Teile. Beispiels Irisöl 28 Teile 3,q.,6-Trim-ethyl-2-[24-oxo-23- methobutyl-]cyclohexan, 3o - Methyljonon, i Teil Laurinaldehyd, 7 Teile Fjugenol, 33 - Myristinsäure, i Teil Heptincarhonsäuremethylester, ioo Teile. Beispie16 Linidenbiütenöl`: _ - - g Teile 4.-Methyl=5-isopropyl-2-[24- oxo - 23 - methobtttyl-1 cyclo- hexan, 50 - Hydroxycitronellal, io - Phenyläthylalkohol, 14 - Benzylalkohol, 5 - a-Amylzimtal.dehyd, 3 - Acetophenon, i Teil Cumarin, 8 Teile Linalylacetat, ioo Teile. For example, there may be mentioned: [q.-0x0-3-methobutyl-] cyclohexane, colorless liquid, KP 98 to 10,000.5 mm, 1.5-dimethyl-12- [24-oxo-23-methobutyl; ] cyclohexane, colorless liquid, KP i 12 to 114 ', 3 mm, 3,4,6-trimethyl -2- [24-OXO- 23 - methobutyl-] cyclohexane, colorless liquid, KP 115 to 117 °, 3 mm, q.-methyl-5-isopropyl-2- [24-oxo-z-methobutyl-] cyclohexane, colorless liquid, KP 128 to 130 °, 4 mm, the hitherto unknown aldehydes in question can be prepared by known processes win for the representation of aldehydes, z. B. from adene by one carbon atom poorer ketones by condensation. mii haloacetic acid esters according to the method of patent 17q.279 and! Cleavage of the glycidic acids obtainable in this way according to patent 17q.239. Example i Fantasy perfume base: 2o parts 1,1,3-trimethyl-2- [24-oxo-23- methobutyl-] cyclohexane, 5 - Jonon, io - methyl j onon, 8 - Ylang-Ylang-C51, 5 - artificial Jasmine oil, :1. - heliotropin, 8 - coumarin, io - phenylethyl alcohol, 15 - bergamot oil, 5 - bitter orange oil, 5 - East Indian sandalwood oil, 5 - musk ambrette, ioo parts. Example e Flower oil base: 6 parts -1, I, 3-trimethyl-2- [24-oxo-23- ethobutyl-] cyclohexane, 35 - hydroxycitronellal, 26 - benzyl alcohol, 1 o - benzyl acetate, io - phenylethyl alcohol, io - cinnamon alcohol, 3 - Y long ylang oil, ioo parts. Example l3. Lily of the valley soap perfume: 7 parts [4.-Oxo-3-methObutyl-1cYclo- hexane, 30 - Linaloe Oil, 2o - hydroxycitronellal, I o - Canang aöl, 3 - benzaldehyde, 2o - terpineol, io - benzyl acetate, ioo parts. Example ¢ Jasmine oil: io parts I, 5-dimethyl-2- [24 - oxo-23- methobutyl-] cyclohexane, 35 - benzyl acetate, qo - benzyl alcohol, 5 - linalool, 5 - linalyl acetate, 5 - anthranilic acid methyl ester, ioo parts. Example Iris oil 28 parts 3, q., 6-trim-ethyl-2- [24-oxo-23- methobutyl-] cyclohexane, 3o - methyl ionone, i part of lauric aldehyde, 7 parts of fjugenol, 33 - myristic acid, i part of methyl heptinic acid, ioo parts. Example 16 Linid Blossom Oil: _ - - g parts of 4.-methyl = 5-isopropyl-2- [24- oxo - 23 - methobtttyl-1 cyclo- hexane, 50 - hydroxycitronellal, io - phenylethyl alcohol, 14 - benzyl alcohol, 5 - a-amylcinnamic aldehyde, 3 - acetophenone, i part of coumarin, 8 parts of L inalylacetate, ioo parts.

Claims (1)

PATRNTANSPRUCII: Verfahren zur Herstellung von Riech- stoffmischungen, gekennzeichnet durch die Verwendung von. 24-Oxo-23,allzy lbutyl- cyclohexan oder seinen Kernsubstitutions- prodttkten.
PATRNTANSPRUCII: Process for the production of olfactory Mixtures of substances, characterized by the Use of. 24-Oxo-23, alcylbutyl- cyclohexane or its core substitution products.
DEI38415D 1929-06-18 1929-06-18 Process for the production of fragrance mixtures Expired DE501627C (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEI38415D DE501627C (en) 1929-06-18 1929-06-18 Process for the production of fragrance mixtures
NL27877D NL27877C (en) 1929-06-18 1930-03-01

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI38415D DE501627C (en) 1929-06-18 1929-06-18 Process for the production of fragrance mixtures

Publications (1)

Publication Number Publication Date
DE501627C true DE501627C (en) 1930-07-17

Family

ID=7189773

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI38415D Expired DE501627C (en) 1929-06-18 1929-06-18 Process for the production of fragrance mixtures

Country Status (2)

Country Link
DE (1) DE501627C (en)
NL (1) NL27877C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7511001B2 (en) 2007-07-31 2009-03-31 International Flavors & Fragrances Inc. Substituted cyclohexyl propanal compounds and their use in perfume compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10022971B4 (en) * 2000-05-11 2010-12-23 Kao Corporation Use of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal as fragrance

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7511001B2 (en) 2007-07-31 2009-03-31 International Flavors & Fragrances Inc. Substituted cyclohexyl propanal compounds and their use in perfume compositions

Also Published As

Publication number Publication date
NL27877C (en) 1932-04-15

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