NL8304146A - PROCESS FOR PREPARING CIS-JASMON. - Google Patents
PROCESS FOR PREPARING CIS-JASMON. Download PDFInfo
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- NL8304146A NL8304146A NL8304146A NL8304146A NL8304146A NL 8304146 A NL8304146 A NL 8304146A NL 8304146 A NL8304146 A NL 8304146A NL 8304146 A NL8304146 A NL 8304146A NL 8304146 A NL8304146 A NL 8304146A
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/12—Chewing gum characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
- A23G4/126—Chewing gum characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins containing vitamins, antibiotics
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
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- 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
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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
- C11B9/0026—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
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0084—Antioxidants; Free-radical scavengers
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Description
i* ï c % *i * ï c% *
Werkwijze voor het bereiden van cis—jasmonMethod for preparing cis-jasmon
De uitvinding heeft "betrekking op een werkwijze voor Ziet "bereiden van cis-jasmon, een in het bijzonder voor de parfumindustrie belangrijke stof.The invention relates to "a process for Ziet" preparation of cis-jasmon, a substance which is particularly important for the perfume industry.
De uitvinding beoogt een nieuwe werkwijze 5 voor de bereiding van cis-jasmon te verschaffen. Bij deze werkwijze laat men 3-metbylcyclopentenon-2 met cis-pent-2-enyl-1 -halogeni-de reageren bij aanwezigheid van êên of meer inerte oplosmiddelen, waterige alkalihydroxiden en êên of meer "fase-overdradtsmiddelen'.'The object of the invention is to provide a new process for the preparation of cis-jasmon. In this process, 3-methylcyclopentenone-2 is reacted with cis-pent-2-enyl-1-halide in the presence of one or more inert solvents, aqueous alkali hydroxides and one or more "phase transfer agents."
De reactie wordt uitgevoerd in een 2-fase systeem en kan worden 10 toegelicht door het reactieschema A, waarin X chloor of broom en M een alkalinetaal voorstelt.The reaction is carried out in a 2-phase system and can be illustrated by the reaction scheme A, in which X represents chlorine or bromine and M represents an alkaline language.
Meer in het bijzonder heeft de uitvinding betrekking op een werkwijze voor het bereiden van cis-jasmon met de formule 1, met het kenmerk, dat men 3-methyl cyclopentenon-2 15 met de formule 2 innig mengt met een cis pentenylhalogenide met de formule 3, bij aanwezigheid van een base en een "fase-overdrachts-middel" met de algemene formule 1;, waarin tenminste êên van de groepen , Rg, Rg en R^ voorstelt Cg-C.^ aryl, 06-C10 aralkyl, Cg-C2q alkyl Cg-C.^ alkaryl of Cg-C^g alkenyl en de andere groepen 29 Rg, R^ en R^ voorstellen C^-Cg alkyl en ΊΓ een anion is, gekozen uit een halogeenanion of een hydroxylanion, terwijl X chloor of broom voorstelt waarbij de reactie wordt uitgevoerd in een vloeibaar 2—fasen systeem, de reactietemperatuur ligt in het traject van 30-200°C, de molaire verhouding van 3-methyl cyclopentenon-2 25 tot cis pent-2-enyl halogenide ligt in het traject van 0,5:1,5 tot 1,5:0,5» de concentratie aan nfase-overdrachtsmiddel" in de reac-tiemassa ligt in het traject van 0,5 g fase-overdrachtsmiddel per "\ ___ O 8304146 -2-.More particularly, the invention relates to a process for the preparation of cis-jasmon of the formula 1, characterized in that 3-methyl cyclopentenone-2 of the formula 2 is intimately mixed with a cis-pentenyl halide of the formula 3 , in the presence of a base and a "phase transfer agent" of the general formula I, wherein at least one of the groups Rg, Rg and R 1 represents C 8 -C 18 aryl, 06-C 10 aralkyl, C 8 C2q alkyl C8 -C18 alkaryl or Cg-C18g alkenyl and the other groups 29 Rg, R19 and R19 are C1 -C8 alkyl and is is an anion selected from a halo anion or a hydroxyl anion, while X is chlorine or bromine in which the reaction is carried out in a liquid 2-phase system, the reaction temperature is in the range of 30-200 ° C, the molar ratio of 3-methyl cyclopentenone-2 to cis pent-2-enyl halide is in the range from 0.5: 1.5 to 1.5: 0.5 "the concentration of nphase transfer agent" in the reaction mass is in the range from 0.5 gf ase transfer agent per "8304146 -2-.
mol 3-methyl cyclopentenon-2 tot 25 g fa® -overdrachtsmiddel per mol 3-methylcyclopentenon-2, in het voor het reactiesysteem inert oplosmiddel, gekozen uit tolueen, henzeen, o—xyleen, m—xyleen, p—xyleen, ethylbenzeen, n-hexaan en cyclohexaan, dat men het ver-5 kregen pradukt gefractioneerd destilleert, waarbij een residu en een destillaat worden gevormd en dat men het cis-jasmon uit het destillaat wint.mole 3-methyl cyclopentenone-2 to 25 g fa® transfer agent per mole 3-methylcyclopentenone-2, in the reaction system inert solvent selected from toluene, henzene, o-xylene, m-xylene, p-xylene, ethylbenzene, n-hexane and cyclohexane, that the resulting product is fractionally distilled, whereby a residue and a distillate are formed and the cis-jasmon is recovered from the distillate.
Bij de werkwijze volgens de uitvinding bevinden de reagentia voor de werkwijze en de base zich respectievelijk 10 in twee niet-mengbare fases; een organische fase en hetzij (1) een waterige base—fase of (2] een vaste base—fase, waarbij de reagentia zich nagenoeg geheel in de eerste, organische fase en de base zich nagenoeg geheel in de tweede fase beyindt.In the method of the invention, the reagents for the method and the base are in two immiscible phases, respectively; an organic phase and either (1) an aqueous base phase or (2] a solid base phase, the reagents being almost entirely in the first, organic phase and the base being almost entirely in the second phase.
Voorbeelden van geschikte fase-overdrachts— ^5 middelen zijn onder andere: trie aprylmet hylammonlumchlori de, cetyltrimethylammoniumbrcmriL.de en b enzylt rimethy lammoniumhydr oxydeExamples of suitable phase transfer agents include: triyl apryl with hylammonlumchloride, cetyltrimethylammonium bromide, and methyl ethyl ammonium hydride oxide
De tijdsduur van de reactie is omgekeerd evenredig met de reactie-20 temperatuur en kan in het algemeen variëren van 30 minuten tot 10 uur.The reaction time is inversely proportional to the reaction temperature and can generally range from 30 minutes to 10 hours.
De molaire verhouding van 3-met hyl cyclop ent er-non-2 tot cis-pent-2-enyl-t-halogenide ligt bij voorkeur in het traject van 1:1 tot 1:1,2. De molaire verhouding van base tot 25 cis-pent-2-enyl—1-halogenide kan liggen in het traject van ongeveer 0,75:1 tot ongeveer 1,5:1, waarbij een verhouding van ongeveer 1:1 tot ongeveer 1,2:1 de voorkeur verdient.De voorkeursconcentratie aan fase-overdrachtsmiddel ligt in het traject van 2,5-755 g fase-overdrachtsmiddel per mol 3-methyl cyclopentenon-2.The molar ratio of 3-with hyl cyclop graft er-non-2 to cis-pent-2-enyl-t-halide is preferably in the range of 1: 1 to 1: 1.2. The molar ratio of base to cis-pent-2-enyl-1-halide can range from about 0.75: 1 to about 1.5: 1, with a ratio of about 1: 1 to about 1, 2: 1 is preferred. The preferred concentration of phase transfer agent is in the range of 2.5-755 g of phase transfer agent per mole of 3-methyl cyclopentenone-2.
30 De werkwijze wordt bij voorkeur uitgevoerd bij atmosferische druk.. Lagere of hogere drukken beïnvloeden de uiteindelijke opbrengst echter niet in ongunstige zin. Als base wordt bij voorkeur natrium- of kaliumhydroxyde gebruikt.The process is preferably carried out at atmospheric pressure. However, lower or higher pressures do not adversely affect the final yield. Sodium or potassium hydroxide is preferably used as the base.
Φ 8304146 - 3 -30 8304146 - 3 -
De volgende voorbeelden lichten de uitvinding nader toe.The following examples further illustrate the invention.
Voorbeeld IExample I
Bereiding van cis-jasmon ^ In een reakfciekolf van 250 ml, voorzien van verwarmingsmantel, koeler, roerder, thermometer en druppeltrechter, brengt men een oplossing van 21,3 g natriumhydraxyde en 21,3 g water. Daarna wordt 20 g tolueen en 1,5 g tricaprylmethylammonium-chloride (ALIQUAT 33$ , in de handel gebracht door General Mills 10Preparation of cis-jasmon In a 250 ml reaction flask equipped with heating jacket, condenser, stirrer, thermometer and dropping funnel, a solution of 21.3 g of sodium hydroxide and 21.3 g of water is introduced. Then 20 g of toluene and 1.5 g of tricaprylmethylammonium chloride (ALIQUAT 33 $) are marketed by General Mills 10
Chemicals’ Ine.) bij het mengsel gevoegd. De reaktiemassa wordt vervolgens tot terugvloeien (102°C) verhit en in de loop van een uur wordt een mengsel van 35 g cIs-pent-2-enyl-l-chloride en 2^,5 g 3-methylcy clopentenon-2 onder terugvloeien bij de reaktiemassa gevoegd. Men laat de reaktiemassa daarna nog k uur terugvloeien, 15 waarna deze wordt gemengd met 100 ml koud water en overgebracht m een scheitrechter.Chemicals (Ine.) Added to the mixture. The reaction mass is then heated to reflux (102 ° C) and over an hour a mixture of 35 g of cIs-pent-2-enyl-1-chloride and 2.5 g of 3-methylcyclopentenone-2 is refluxed added to the reaction mass. The reaction mass is then allowed to reflux for an additional hour, after which it is mixed with 100 ml of cold water and transferred to a separatory funnel.
De organische laag wordt afgescheiden, neutraal gewassen en het oplosmiddel wordt af ge stript. De overblijvende olie wordt daarna achtergehouden en gemengd met het reaktieprodukt 20 van voorbeeld II voordat destillatie plaats heeft.The organic layer is separated, washed neutral and the solvent is stripped off. The residual oil is then held back and mixed with the reaction product of Example II before distillation takes place.
Voorbeeld II Bereiding van cis-jasmonExample II Preparation of cis-jasmon
In een reaktiekolf van 1 1, voorzien van ver- warmingsmantel, koeler, thermometer, druppeltrechter en roerder, 25 . .In a 1 L reaction flask equipped with heating jacket, cooler, thermometer, dropping funnel and stirrer, 25. .
brengt men een oplossing van 106,5 g natrrumhydroxyde in 106,5 g water. Daarna wordt 100 g tolueen en 7,5 g tricaprylmethylammonium— chloride bij het mengsel gevoegd. Het mengsel wordt tot terugvloeLen verhit en in de loop van een uur wordt een mengsel van 122,5 g 3-methylcyclopentenon-2 en 175 g eis-pent-2-enyl-l-chloride bij 30 ^ de reaktiemassa gevoegd. De reaktiemassa wordt daarna 2 uur tot * terugvloeien verhit, waarna er 250 ml water aan wordt toegevoegd en het verkregen mengsel wordt overgebracht in een scheitrechter.a solution of 106.5 g of sodium hydroxide in 106.5 g of water is introduced. 100 g of toluene and 7.5 g of tricaprylmethyl ammonium chloride are then added to the mixture. The mixture is heated to reflux and over an hour a mixture of 122.5 g of 3-methylcyclopentenone-2 and 175 g of pent-2-enyl-1-chloride is added to the reaction mass. The reaction mass is then heated to reflux for 2 hours, after which 250 ml of water is added and the resulting mixture is transferred to a separatory funnel.
• De organische laag wordt afgescheiden, neu- T 8304146The organic layer is separated, neutral 8304146
MM
- 1+ - traal genassen en het oplosmiddel -wordt afgestript.- 1+ - heal quickly and the solvent - is stripped off.
De achterblijvende olie wordt daarna gemengd met het produkt van voorbeeld I en het verkregen prodükt wordt ge- (0 combi'neerd met 17 g Primol0 , 7 g triethanolamine en overgehaald 5 om de volgende frakti.es- te verkrijgen.The residual oil is then mixed with the product of Example I and the resulting product is (0 combined with 17 g of Primol, 7 g of triethanolamine and passed over to obtain the following fraction.
Fraktie damptempera- vloeistoftempe- Vacuum Gewicht no. tuur (°CX ratuur (°Cl mm (gl 1 1+3-120 91-159 2,6 27,3 10 2 125 162 2,6 19,0 3 167 185 2,6 18,3 1+ 181+ 201 2,5 19,1+ 5 203 217 2,5 16,1+ 6 220 2l+0 2,5 26,9 15Fraction vapor temperature liquid temperature Vacuum Weight no. Temperature (° CX rature (° Cl mm (gl 1 1 + 3-120 91-159 2.6 27.3 10 2 125 162 2.6 19.0 3 167 185 2, 6 18.3 1+ 181+ 201 2.5 19.1+ 5 203 217 2.5 16.1+ 6 220 2l + 0 2.5 26.9 15
De frakties 1, 2 en 3 van het overgehaalde materiaal worden samengevoegd en gecombineerd met 2 g Primol en Ionox ® . Het verkregen materiaal wordt daarna gefraktioneerd gedestilleerd op een Vigreaux kolom met 12 schotels, waarbij men de 20 ...The fractions 1, 2 and 3 of the transferred material are combined and combined with 2 g of Primol and Ionox ®. The material obtained is then fractionally distilled on a Vigreaux column with 12 trays, the 20 ...
volgende frakti.es verkrijgt.obtain the following fractions.
Fraktie damptempera— vloeistoftem- Vacuum gewicht no. tuur peratuur(°C) mm (g) 1 2 3 4 5 6 7 8 9 (^8304146 53 107 3,5 l+,8 2 25 2 36 100 1,0 l+,5 3 72 120 0,8 3,1 4 h 80 121 0,8 l+,0 5 80 123 1,0 l+,9 6 78 122 1,2 l+,2 7 30 7 79 128 1,2 3,8 8 79 137 1,2 l+,6 9 79 1¼ 1,2 .3*9 - 5 - 30 87 353 3,2 2,3 31 97 359 3,2 U,1 32 98 371* 3,2 3,8 33 332 382 3,2 2,k 3l· 320 20k 3,2 3,9 35 325 25Ο 3,2 2,6Fraction vapor temperature - liquid temperature - Vacuum weight no. Temperature (° C) mm (g) 1 2 3 4 5 6 7 8 9 (^ 8304 146 53 107 3,5 l +, 8 2 25 2 36 100 1,0 l +, 5 3 72 120 0.8 3.1 4 h 80 121 0.8 l +, 0 5 80 123 1.0 l +, 9 6 78 122 1.2 l +, 2 7 30 7 79 128 1.2 3.8 8 79 137 1.2 l +, 6 9 79 1¼ 1.2 .3 * 9 - 5 - 30 87 353 3.2 2.3 31 97 359 3.2 U, 1 32 98 371 * 3.2 3.8 33 332 382 3.2 2, k 3l 320 20k 3.2 3.9 35 325 25Ο 3.2 2.6
De fracties 6-g worden samengevoegd, geanalyseerd en beoordeeld. Door HMR, IR en massa-spectraalanalyse 'blijkt het produkt te bestaan uit 9k% cis-jasmon net de formule 30 en voor de rest uit trans' jasmon. Eet NMR spectrum is aangegeven in fig. 3. Het IR spectrum is aangegeven in fig.2.Fractions 6-g are pooled, analyzed and evaluated. HMR, IR and mass spectral analysis show that the product consists of 9% cis-jasmon of the formula 30 and the remainder of trans-jasmon. The NMR spectrum is shown in Figure 3. The IR spectrum is shown in Figure 2.
Voorbeeld IIIExample III
JasmijnparfumJasmine perfume
Het volgende mengsel wordt bereid:The following mixture is prepared:
Bestanddelen gewicht sdelen paracresol 1 acetylmethylanthranilaat 20 famesol b cis-3-b exenylbenzoaat 30 nerolidol 30 indol 15 eugenol 20 benzylalkohol U0 methyllinoleaat U0 jasmijnlacton 20 dihydromethyljasmonaat 10 linalool 350 benzylacetaat h-00 abietylalkohol 3 50 cis jasmon (bereid volgens voor- beeld II;samengevoegde fracties 50 Λ ----- \ 8304146 - 6 - Λ η Het volgens voorbeeld IX bereide cis-jasmon vers;cbaft aan deze jasmijncompositie de groene, zoete selderij-aehtlge noot, die voor jasmijn—parfumcomposities zo belangrijk is.Components weight parts paracresol 1 acetylmethyl anthranilate 20 famesol b cis-3-b exenyl benzoate 30 nerolidol 30 indole 15 eugenol 20 benzyl alcohol U0 methyl linoleate U0 jasmine lactone 20 dihydromethyl jasmonate 10 linalol 350 benzyl acetate h-00 abietyl alcohol 2 prepared together 50 abityl alcohol 3 fractions 50 Λ ----- \ 8304146 - 6 - Λ η The cis-jasmon prepared according to Example IX freshly binds to this jasmine composition the green, sweet celery-like note, which is so important for jasmine perfume compositions.
0 π 1 8304146 9 •A Φ _________0 π 1 8304146 9 • A Φ _________
Claims (3)
Applications Claiming Priority (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/649,552 US4010207A (en) | 1976-01-15 | 1976-01-15 | Process for the alkylation of α, β-unsaturated aldehydes |
| US64955276 | 1976-01-15 | ||
| US64954476 | 1976-01-15 | ||
| US05/649,544 US4045489A (en) | 1976-01-15 | 1976-01-15 | Process for producing cis-jasmone |
| US05/713,429 US4021488A (en) | 1976-08-11 | 1976-08-11 | 1-Acetyl-3,3-dimethyl-(2-propenyl)cyclohexane |
| US05/713,357 US4062894A (en) | 1976-08-11 | 1976-08-11 | Derivatives of 1-acetyl-3,3-dimethylcyclohexane |
| US71335776 | 1976-08-11 | ||
| US71342976 | 1976-08-11 | ||
| US05/740,948 US4081481A (en) | 1976-08-11 | 1976-11-11 | 1-Butanoyl-3,3-dimethylcyclohexane |
| US74094876 | 1976-11-11 | ||
| US05/741,088 US4068012A (en) | 1976-11-11 | 1976-11-11 | Use of 1-(2-propenyl)-3-(4-methyl-3-pentenyl)-Δ3 -cyclohexene-1-carboxaldehyde and 1-(2-propenyl)-4-(4-methyl-3-pentenyl)-Δ3 -cyclohexene-1-carboxaldehyde |
| US74108876 | 1976-11-11 | ||
| US05/753,453 US4102928A (en) | 1976-08-11 | 1976-12-22 | Process for producing substituted-1-acetyl-3,3-dimethylcyclohexane |
| US75361776 | 1976-12-22 | ||
| US05/753,617 US4081479A (en) | 1976-08-11 | 1976-12-22 | Substituted-1-acetyl-3,3-dimethylcyclohexane |
| US75345376 | 1976-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8304146A true NL8304146A (en) | 1984-04-02 |
Family
ID=27575497
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NLAANVRAGE7700367,A NL176665C (en) | 1976-01-15 | 1977-01-14 | METHOD FOR PREPARING ALDEHYDES AND METHOD FOR IMPROVING, MODIFYING OR IN ANY WAY INFLUENCING TASTE AND ODOR OF FOOD, TOBACCO OR PERFUME USING THESE ALDEHYDES |
| NL8304147A NL8304147A (en) | 1976-01-15 | 1983-12-02 | PROCESS FOR PREPARING CYCLOHEXAN DERIVATIVES AND FOR AROMATIZING FOODSTUFFS USING THESE CYCLOHEXAN DERIVATIVES. |
| NL8304146A NL8304146A (en) | 1976-01-15 | 1983-12-02 | PROCESS FOR PREPARING CIS-JASMON. |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NLAANVRAGE7700367,A NL176665C (en) | 1976-01-15 | 1977-01-14 | METHOD FOR PREPARING ALDEHYDES AND METHOD FOR IMPROVING, MODIFYING OR IN ANY WAY INFLUENCING TASTE AND ODOR OF FOOD, TOBACCO OR PERFUME USING THESE ALDEHYDES |
| NL8304147A NL8304147A (en) | 1976-01-15 | 1983-12-02 | PROCESS FOR PREPARING CYCLOHEXAN DERIVATIVES AND FOR AROMATIZING FOODSTUFFS USING THESE CYCLOHEXAN DERIVATIVES. |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS52106809A (en) |
| DE (2) | DE2700688B2 (en) |
| FR (1) | FR2338240A1 (en) |
| NL (3) | NL176665C (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292447A (en) * | 1978-12-15 | 1981-09-29 | International Flavors & Fragrances Inc. | Process for hydrogenation of 2,6,6-trimethyl cyclohexene derivatives, products produced thereby and organoleptic uses of said products |
| DE3013672A1 (en) * | 1980-04-09 | 1981-10-15 | Consortium für elektrochemische Industrie GmbH, 8000 München | 2,4-DIALKYL-2.6-HEPTADIENAL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS AN ODOR AND TASTE |
| US4507225A (en) * | 1983-04-21 | 1985-03-26 | International Flavors & Fragrances Inc. | Process for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles with 1-phenylpenten-4-one-1 and methyl homologues thereof |
| CA2427983C (en) | 2000-11-06 | 2009-06-02 | Japan Tobacco Inc. | Tobacco odor deodorizing perfume compositon, tobacco odor deodorant, cigarette low in sidestream smoke odor, and tobacco package |
| DE60136090D1 (en) * | 2000-11-06 | 2008-11-20 | Japan Tobacco Inc | TOBACCO ODOR DESODORIZATION COMPOSITION, TOBACCO ODOR DESODORIZATION AND CIGARETTE AND TOBACCO PACKING WITH REDUCED SECONDARY SMOKING ODOR |
| FR2953405B1 (en) * | 2009-12-04 | 2016-08-26 | Oreal | METHOD FOR INGESTION SCRAPING OF AT LEAST TWO EDIBLE SCENIC SUBSTANCES HAVING DIFFERENT MAXIMUM DIFFUSION TIME; MULTI-COMPONENT SCARFING AGENT |
| CN107848924B (en) * | 2015-07-27 | 2021-04-02 | 奇华顿股份有限公司 | 2,4, 7-Trimethyloct-6-en-1-ol as fragrance ingredient |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4889861A (en) * | 1972-03-01 | 1973-11-24 | ||
| JPS581093B2 (en) * | 1972-10-05 | 1983-01-10 | トヨタマコウリヨウ カブシキガイシヤ | Alkylation method of 3-methyl-2-cyclopentenone |
| JPS5810368B2 (en) * | 1973-08-09 | 1983-02-25 | 株式会社クラレ | Production method of methylheptenone |
| CH586551A5 (en) * | 1974-01-29 | 1977-04-15 | Firmenich & Cie | |
| IT1034605B (en) * | 1974-04-19 | 1979-10-10 | Givaudan & Cie Sa | PERFUMES |
-
1977
- 1977-01-08 DE DE2700688A patent/DE2700688B2/en not_active Withdrawn
- 1977-01-08 DE DE2759425A patent/DE2759425C3/en not_active Expired
- 1977-01-14 JP JP348277A patent/JPS52106809A/en active Pending
- 1977-01-14 NL NLAANVRAGE7700367,A patent/NL176665C/en not_active IP Right Cessation
- 1977-01-17 FR FR7701152A patent/FR2338240A1/en active Granted
-
1983
- 1983-12-02 NL NL8304147A patent/NL8304147A/en not_active Application Discontinuation
- 1983-12-02 NL NL8304146A patent/NL8304146A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2759425C3 (en) | 1981-04-23 |
| FR2338240B1 (en) | 1983-06-10 |
| NL7700367A (en) | 1977-07-19 |
| JPS52106809A (en) | 1977-09-07 |
| DE2700688A1 (en) | 1977-07-21 |
| FR2338240A1 (en) | 1977-08-12 |
| DE2700688B2 (en) | 1979-12-06 |
| NL176665C (en) | 1985-05-17 |
| NL8304147A (en) | 1984-04-02 |
| DE2759425B1 (en) | 1980-07-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1B | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |