DE502333C - Process for the production of fragrances - Google Patents

Process for the production of fragrances

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Publication number
DE502333C
DE502333C DEI31603D DEI0031603D DE502333C DE 502333 C DE502333 C DE 502333C DE I31603 D DEI31603 D DE I31603D DE I0031603 D DEI0031603 D DE I0031603D DE 502333 C DE502333 C DE 502333C
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Germany
Prior art keywords
parts
fragrances
oxo
compounds
pressure
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Expired
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DEI31603D
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German (de)
Inventor
Dr Angelo Knorr
Dr Albert Weissenborn
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IG Farbenindustrie AG
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IG Farbenindustrie AG
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Priority to DEI31603D priority Critical patent/DE502333C/en
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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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • 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
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • 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
    • 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
    • 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
    • C07C45/72—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 by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—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 by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/542—Alkylated benzaldehydes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/546—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Description

Verfahren zur Herstellung von Riechstoffen Viele niatürliche oder synthetisch berge- stellte Riechstoffe enthalten als wesentlichen Bestandteil die Isopropylgruppe, so z. B. :der im Römisch-Kümmel5l enthaltene 4-Isopro- pyl@benzaidehyc1 (Cumin.aldehy(1), der von Ga t t e r m a n n (vgl. Liebigs Annalen der Chemie 3q.7, Seite 38o) synthetisch dargestellt wurde. Wie gefunden wurde, bikleri aroma- tische Oxoverbindungen, deren Kern durch zwei Is@opropylgruppen siubstituiert ist, sehr wertvolle Riechstoffe. Dies war nicht vor aus- zusehen, da solche Veribind'ungen bisher we- rIer in der Natur beobachtet noch dargestellt worden ,sind und da im allgemeinen dlie Ver- größerung des Moleküls mit dem Ansteigen des Siedepunkts eine Schwächung des Ge- ruchs und seines besonderen Charakters :nach sich zieht. Man .kann die in Frage ,kommenden Verbin- dungen gewinnen, indem man nach bekann- ten Methoden in einen aromatischen Kohlen- wasserstoff, der bereits zwei Isopropy1grup- pen enthält, eine Oxogruppeeinführt oder indem man in Monoisopropyliaryl@verbind,un,- gen gleichzeitig eine zweite Islopriopylgruppe und eine Oxogruppe einführt oder indem m!an aromatische Oxoverbind-ungen, dlie keine oder niur eine Isopropylgruipp,e -enthalten, in die entsprechenden Di.is.opropylverbind@ungen um- wandelt. Bei der Aus-fübrungdieser Reak- tionen kann man :unter anderem von mono- oder triisop ropyl,s,ubstbuierten Kohlen.wasser- stoffen .ausgehen, die @durch ;Spaltungs- und gegebenenfalls Kon,densations.reaktionen die entsprechenden Dii.sopropylver indungen .ent- stehen lassen, die dann durch Aufnahme einer Oxogruppe die wertvollen Riechstoffe er- geben. Durch Einfügung,der ,zwei Isopropyl- gruppen wird .der Geruchscharakter im Ver- gleich zu den Riechstoffen mlit keiner oder mit einer Isopropylgiuppe weitgehend abge- ändlert. Beispiel i Zu i5 Teilen Diisopropyl'benzol vorn Kp. 204 bis 2o8°, io Teiilen Nl,uminiumchlorid und i Teil Kupferchlorür, wind bei gewöhn- licher oder erhöhter Temperatur .so lange Kohlen ,oxyd geleitet, bis nichts mehr au:fge- notn;men wird. Man erhält io Teile D.i.iso- propylbenzald,ohvd vom KP- 147 bis i53° bei 12 biis 13 mm .Druck .al,s,diiclcfließendie farblbse Flüssigkeit. Man kann boi gewöhnlichem oder erhöhtem Druck arbeiten mit oder ohne Mitverwen- rl,ung von gasförmiger Salzsäure. Beispiel 2 i 5 Teile Isopropyl'be:nzol (Cumol) @werden mit io Teilen Alumin:i;u,mchlorid und i Teil K:up@ferch,lorür versetzt. Zu der Mischung wird solange Kohlenoxyd geleitet, bis nichts mehr davon aufgenommen wird. Nach :d'er Aufarbeitung erhält -man -6- bis 7 Teile des im Beispiel i genannten DiisopropylbenzaIdie- hyd,s neben u.nverändertean Isopropylben,zo,l und idurch Spaltung entstandeniem Benzol. Beispiel 3 15 Teile Diisopropyltoliuol vom Kp. foo b!i.s 1o4° unter gmm Druck werden in Gegen- wart von 9 Teilen Alu:min!iiumchlorid und i Teil Kupferahlorür unter Druck mit Koh- lenoxyd behandelt. Nach dem Aufarbeiten des Reaktionsprodukts erhält miau io bis ii Tei'1e Diisopropylm@ethylbenzald!ehyd, eine un- ter 9 mm Druck bei 148 Abis 15o° siedende, nach Monschuskörneröl riieehende farblose ölige Flüssigkeit. Bedspiel 4 16 Teile i-Isopropyl-4-methylbenzol wer- den in Gegenwart von 9 Teilen Aluminium- chloriid und i Teil Kup-erchloriiir bei So bis 6o° unter Druck mit Kohlenoxyd behandelt. Bei ,der Destillation im Vakuum erhält man neben u:nveränd!ertem Isopropyltoluol, ge'biI- detem Toluol und Diisopropyltoiluol ails Hauptbestandteil des Gemisches 6 .bis 7 Teile des im Beispiel 3 genannten Dliisopropy!1- methytbenzaldehyd.s. Beispiel 5 15 Teile Diiisopropyl:xylol vom Kp. i io bis 115° :unter 8 ,mm Druckwerden in Gegen- wart von g Teilen Alumiini!umch arid und i Teil I7,jupferchlorür unter Druck mit Koh- lenoxyd behandelt. Nach. idem Aufarbeiten :les Reaktionsgemisches erhält man 9 bis io Teilte Diisoprop3#idimethyubenzaldehyd, eine unter 9 mm Druck bei 15o bis 155° s'Iedende, nach Moschuskörn:erö,l riechende farblose Qliige- Flüssigkeit. Belispi.el 6 15 Teile Diisopropyl-ar-tetrahydronaphtha- lin vom Kp. 143 Abis 148° !unter 9 mm Druck werden in Gegenwart von 9 Teilen Alumi- niumchlorid und i Teil Kupferchlorür unter Druck mit Kohlenoxyd behandelt. Nach dem AufarbaitendesReaktionsgomisches erhältr=fan 12 bis 13 Teile Dii.sopropyl@ar-tetrahydr!o- nap:h:taldehyd, eine .unter 9 mm Druck bei 182 bis 185° siedende, nach Moschuskörneröl riechende farblose, bei gewöhnlicher Tempe- ratur wachsartig feste Verbindung. Beispiel -7 Man mischt io Teile Diisopropyl!ben;zol vom Kp. 204 bis 2o8° mit 5 Teilen Acetyl- cdiIoriid, fügt bei 12 bis 15° 7 Teila Alu- miniumchlorid hinzu und erwärmt 2 bis 3 Stunden auf 5o°. Bei der Destillation nm @räkuu,m erhält man 7 Teile DiisopropyIl- acetophenon, eine ,unter 13! mm Druck bei 145 bis i50° siedende, mach Moschuskörneröl riechende farblose ölige Flüssigkeit. Als D'iisopropylverbiind,ung, iin der die Oxogruppe in der Seitenkette steht, sei i -Oxo-2-methyl-2- (isopropyll!ph,enyl) -äthan (Isopropylhydratropaa:ldehyd) gemannt. Die Dii:sopr!opyloxoarylverbiindiungen, lassen stich durch Veränderung der Oxogruppe in andere Riechstoffe umwandeln. So erhält man z. B. aus dem obergenannten Düsopropylbenz- ald'ehyd durch alkailische Kondensation müt Aceton D:iisopropyl!benzalaceton; -durch Oxy- elation des gleichen .Aldehyds gewinnt man l)iisopropylbenz.oesäure und' aus dieser die Ester; durch katalytische oder ;beliebig an- -fereRedaktion dies glorchen Aldahyds gelangt _i?un zum Diisopropylibenzylalkohol , der .das entsprechende Acretat liefert; durch Konden- sation,des Diisopropylbenzald,ehydis mit Acet- al,d'ehyd oder dessen Homologen kann man 1-0xa-3-(diisopropyIphenyl)-propen-2 (D!i- -isopropylzim@taldehyd) oder dessen Homolloge darstellen, aus dienen i-Oxo-3-(,d;iisopropyl- phenyl)-propan (Diisopropylihyd.rozimtaldie- hyd); 1-'0x0-3 @ diiiis.opropylph!enyl) -iprop,an (Di@isopropylph,enylpropyhlkohol) oder die Homologen dieser Verbindungen erhalten werd-en. Process for the production of fragrances Many natural or synthetic mountain Asked odoriferous substances included as essential Component is the isopropyl group, so z. B.: the 4-Isopro- contained in Römisch-Kümmel5l pyl @ benzaidehyc1 (Cumin.aldehy (1), published by Ga ttermann (see Liebig's annals of Chemistry 3q.7, page 38o) presented synthetically became. As was found, bikleri aroma- table oxo compounds, the core of which is through two is @propyl groups is very much valuable fragrances. This was not before watch, since such connections have not been rIer observed in nature is still shown have been, and since in general the increase in size of the molecule as it increases the boiling point of a weakening of the overall smell and its special character: after draws itself. You can use the possible connections gain new ideas by methods in an aromatic carbon hydrogen, which already contains two isopropyl groups pen, introduces an oxo group, or by connecting in monoisopropyliaryl @, un, - gen at the same time a second islopriopyl group and introduces an oxo group or by adding m! an aromatic oxo compounds, no or Only one isopropyl group, e -contained, in the appropriate di.is.opropylverbind@ungen um- transforms. In carrying out this reaction one can: among other things, from mono- or triisop ropyl, s, ubstbuierten coals. substances. going out that @through; cleavage and possibly condensation reactions the corresponding diisopropyl compounds. let that stand then by taking a Oxo group the valuable fragrances give. By inserting the, two isopropyl groups. the odor character in the same to the fragrances mlit none or with an isopropyl group largely changes. Example i To 15 parts of diisopropylbenzene bp. 204 to 208 °, 10 parts of ammonium chloride and i part copper chloride, wind at usual lighter or higher temperature. so long Coals, oxide conducted, until nothing more notn; men will. 10 parts of diiso- propylbenzald, ohvd from KP- 147 to i53 ° 12 to 13 mm. Print .al, s, diiclc flow the colorless Liquid. One can be ordinary or elevated Print work with or without using rl, ung of gaseous hydrochloric acid. Example 2 i 5 parts of isopropyl benzene (cumene) are used with 10 parts of aluminum: i; u, mchloride and i part K: up @ ferch, Lorür moved. To the mix carbon dioxide is passed until nothing more of it is absorbed. After Work-up receives -6- to 7 parts of the in example i mentioned diisopropylbenzene di- hyd, s next to and changed to isopropylbene, zo, l and benzene formed by cleavage. Example 3 15 parts of diisopropyltoluene of bp. Foo b! Is 1o4 ° under gmm pressure are counter- War of 9 parts of aluminum: min! iium chloride and i part of copper wire under pressure with carbon lenoxyd treated. After working up the reaction product receives miau io to ii Partly diisopropylm @ ethylbenzaldehyde, an un- the 9 mm pressure at 148 Abis 15o ° boiling, colorless, reminiscent of monschus oil oily liquid. Bedspiel 4 16 parts of i-isopropyl-4-methylbenzene are in the presence of 9 parts of aluminum chloride and i part of copper chlorine in So bis 60 ° treated with carbon dioxide under pressure. In the case of distillation in vacuo, one obtains in addition to modified isopropyltoluene, formed detem toluene and diisopropyltoiluene ails Main component of the mixture 6 to 7 parts of the diisopropy mentioned in example 3! 1- methytbenzaldehyd.s. Example 5 15 parts of diisopropyl: xylene with a boiling point of i io to 115 °: under 8, mm pressure are counter- waited by g parts Alumiini! umch arid and i Part I7, copper chloride under pressure with carbon lenoxyd treated. To. idem working up : les reaction mixture is obtained from 9 to io Shared diisoprop3 # idimethyubenzaldehyde, one under 9 mm pressure at 15o to 155 ° s'Iedende, of musk grain: erö, l smelling colorless Qliige- liquid. Belispi.el 6 15 parts of diisopropyl-ar-tetrahydronaphtha- lin from Kp. 143 Ab to 148 °! under 9 mm pressure are in the presence of 9 parts of aluminum nium chloride and i part of copper chloride Pressure treated with carbon dioxide. After this Building up the reaction gomic received = fan 12 to 13 parts Dii.sopropyl@ar-tetrahydr!o- nap: h: taldehyd, a .under 9 mm pressure at 182 to 185 ° boiling, like musk seed oil smelling colorless, at ordinary temperatures rature waxy solid connection. Example -7 Mix 10 parts of diisopropylbenzol from bp. 204 to 208 ° with 5 parts of acetyl cdiIoriid, inserts at 12 to 15 ° 7 parts of aluminum Add minium chloride and heat 2 to 3 hours at 5o °. At distillation nm @ räkuu, m you get 7 parts diisopropyl- acetophenone, one under 13! mm pressure at 145 Make musk seed oil that simmer up to 150 ° smelling colorless oily liquid. As a diisopropyl compound in which the Oxo group is in the side chain, be i-Oxo-2-methyl-2- (isopropyl, ph, enyl) ethane (Isopropylhydratropaa: ldehyde) man. the Dii: sopr! Opyloxoarylverbiindiungen, let go by changing the oxo group to others Convert fragrances. So you get z. B. from the above-mentioned diisopropylbenzene ald'ehyd through alkali condensation müt Acetone D: isopropylbenzalacetone; -by oxy- elation of the same aldehyde is obtained l) iisopropylbenzoic acid and from this the Ester; by catalytic or; any other -fere editorial this glorious Aldahyds arrives _i? un to the diisopropylibenzyl alcohol, the .das corresponding acetate supplies; through condensation cation, of diisopropylbenzald, ehydis with acet al, d'ehyd or its homologues can be used 1-0xa-3- (diisopropylphenyl) -propen-2 (D! I- -isopropylzim @ taldehyd) or its homologue represent, from serve i-Oxo-3 - (, d; iisopropyl- phenyl) -propane (Diisopropylihyd.rozimtaldie- hyd); 1-'0x0-3 @ diiiis.opropylph! Enyl) -iprop, an (Di @ isopropylph, enylpropyl alcohol) or the Obtain homologues of these compounds will.

Claims (1)

PATENTANSPRÜCHE: i. Verfahren .zur Herstellung von Riechstoffen, da-durch gekennzeichnet, daß man in aromatische DiiisopropyNerb,in - diungen Oxogruppen einführt. 2. Abänderung des Verfahrens nach Anspruch i, dadurch gekennz.eicbnet, daß man aromatische Oxoverbind ragen, die keine o;d-er nur eine Isopropylgruppe ent- halten, in Diisopropylverbin.dungen über- führt. 3. Abänderung des Verfahrens nach Anspruch i, dadurch gekennzeichnet, daß man in Monoisopropylarylverbindungen gleichzeitig eine Oxogruppe und eine zweite Isopropyl!gr.uppe einführt.
PATENT CLAIMS: i. Process. For the production of Fragrances, characterized in that one in aromatic DiiisopropyNerb, in - introduces oxo groups. 2. Modification of the procedure after Claim i, characterized in that one protrudes aromatic oxo compounds, the no o; d-it only contains an isopropyl group hold, in diisopropyl compounds. leads. 3. Modification of the procedure after Claim i, characterized in that one in monoisopropylaryl compounds at the same time an oxo group and a introduces second isopropyl group.
DEI31603D 1927-07-07 1927-07-08 Process for the production of fragrances Expired DE502333C (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1035123B (en) * 1954-10-08 1958-07-31 Polak Frutal Works Process for the production of artificial musk fragrances
WO2000015593A2 (en) * 1998-09-10 2000-03-23 Exxon Chemical Patents Inc. Process for making aromatic aldehydes
US6562996B2 (en) 1998-09-10 2003-05-13 Exxonmobil Chemical Patents Inc. Alkyl aromatic aldehydes

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1035123B (en) * 1954-10-08 1958-07-31 Polak Frutal Works Process for the production of artificial musk fragrances
WO2000015593A2 (en) * 1998-09-10 2000-03-23 Exxon Chemical Patents Inc. Process for making aromatic aldehydes
WO2000015593A3 (en) * 1998-09-10 2000-07-20 Exxon Chemical Patents Inc Process for making aromatic aldehydes
US6303827B1 (en) 1998-09-10 2001-10-16 Exxonmobil Chemicals Patents Inc. Process for making aromatic aldehydes
US6562996B2 (en) 1998-09-10 2003-05-13 Exxonmobil Chemical Patents Inc. Alkyl aromatic aldehydes

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