WO2011067386A2 - Procédé de préparation d'aldéhydes aliphatiques - Google Patents

Procédé de préparation d'aldéhydes aliphatiques Download PDF

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Publication number
WO2011067386A2
WO2011067386A2 PCT/EP2010/068865 EP2010068865W WO2011067386A2 WO 2011067386 A2 WO2011067386 A2 WO 2011067386A2 EP 2010068865 W EP2010068865 W EP 2010068865W WO 2011067386 A2 WO2011067386 A2 WO 2011067386A2
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WO
WIPO (PCT)
Prior art keywords
iii
aldehydes
weight
general formula
hydrogenation
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PCT/EP2010/068865
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German (de)
English (en)
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WO2011067386A3 (fr
Inventor
Jörg Botzem
Andreas Lanver
Klaus Ebel
Karl Beck
Ulrich Griesbach
Ralf Pelzer
Achim Sorg
Nadja Pollmer
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Basf Se
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Publication of WO2011067386A2 publication Critical patent/WO2011067386A2/fr
Publication of WO2011067386A3 publication Critical patent/WO2011067386A3/fr

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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
    • 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
    • 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

Definitions

  • the invention relates to a process for the preparation of aliphatic aldehydes of the general formula I.
  • R 1 is hydrogen or a methyl group
  • R 2 is a straight-chain or branched alkyl radical having 1 to 4 C atoms, preferably a methyl or ethyl group, and the two X are each hydrogen or together represent another CC bond, and use of the aliphatic aldehydes thus prepared as fragrances ,
  • fragrance industry Because of the generally dependent on many unpredictable factors uncertain availability of many natural fragrance components as well as the necessary adaptation to changing fashionable tastes, the fragrance industry has a constant need for new fragrances, either alone or in the form of compositions valuable fragrances with interesting fragrance notes. In addition, there is a growing trend towards the perfuming of everyday products, such as cosmetics and cosmetics technical articles such as glues, detergents and cleaners, for room sprays and other determine.
  • Object of the present invention is to provide a novel advantageous process for the preparation of aliphatic aldehydes of the general formula I.
  • R 1 is hydrogen or a methyl group
  • R 2 is a straight-chain or branched alkyl radical having 1 to 4 C atoms, preferably a methyl or ethyl group, and the two X are each hydrogen or together represent another CC bond to provide.
  • the new process should be particularly simple, inexpensive and effective and suitable for large-scale application.
  • the process is intended to enable the continuous preparation of the aliphatic aldehydes of the formula I.
  • the process according to the invention should proceed in such a way that the autoaldol reaction which normally takes place in the case of aliphatic aldehydes of the respective aldehydes is largely suppressed. The same applies to the unwanted Heteroaldolre stroke with the unwanted partners.
  • R 1 is hydrogen or a methyl group
  • R 2 is a straight-chain or branched alkyl radical having 1 to 4 C atoms and the two X are each hydrogen or together form a further CC bond,
  • room temperature means a temperature of 20 ° C. Unless indicated otherwise, temperature data are in degrees Celsius (° C.).
  • the invention relates to a process for the preparation of aliphatic aldehyde of the general formula I.
  • R 1 is hydrogen or a methyl group
  • R 2 is a straight-chain or branched alkyl radical having 1 to 4 C atoms, preferably a methyl or ethyl group, and the two X are each hydrogen or together represent a further CC bond, preferably 2,5,7,7- Tetramethyloctanal, 2,4,5,7,7-pentamethyloctanal, 2-ethyl-5,7,7-trimethyloctanal and 2,5,7,7-tetramethyl-2-octene-1-al, especially 2,5,7 , 7-tetramethyloctanal, in which one
  • aldehydes of the general formulas III and II are used in a molar ratio of 111: 11 of between 1.4: 1 and 0.6: 1 and use of the aliphatic aldehydes thus prepared as fragrances.
  • variable "X" in the general formula I it should be pointed out in the context of the present invention that these after the actual aldol reaction initially together represent a further CC bond and, after the hydrogenation carried out optionally, in each case for hydrogen According to the present invention, the continuous mode of operation in step iii) is preferred.
  • the aliphatic aldehydes of the formula I have valuable perfume properties.
  • Particularly interesting aldehydes of the formula I are those in which R 1 is hydrogen or a methyl group and R 2 is a methyl group or an ethyl group and X is hydrogen.
  • a preferred embodiment of the present invention is a process for the preparation of 2,5,7,7-tetramethyloctanal.
  • the aldehydes of the general formula I can be used advantageously as fragrances or constituents of perfume oils for cosmetic or technical applications. They can be used in compositions within a broad concentration range and blend well with common perfume ingredients and other fragrances to create novel compositions.
  • the proportion of aliphatic aldehydes in fragrance compositions can be between 1 and 50% by weight, based on the weight of the composition.
  • compositions can be used for the perfuming of cosmetic preparations, such as creams, lotions, perfumed waters, toilet soaps, mouthwashes, aerosols and in the Extrait perfumery. They can also be used to improve the odor of technical products such as detergents, detergents and softeners. Normally, 0.05 to 2 wt.% Of such a composition, based on the total product used.
  • aldehydes of the formula I prepared by the process according to the invention for imparting, improving or modifying the odor properties of perfumes or perfumed products.
  • the aldehydes of the formulas II and III are commercially available compounds.
  • the aldehydes of the formula III such as propionaldehyde, butyraldehyde, isovaleraldehyde, n-valeraldehyde and n-hexanal are important technical intermediates, and are therefore inexpensive in sufficient quantity Available.
  • propanal is used as the preferred aldehyde III.
  • the process according to the invention is based on an aldol reaction (aldol condensation) of the aldehydes of the formulas II and III and subsequent hydrogenation.
  • the hydrogenation subsequent to the aldol reaction is carried out continuously, and the product from the aldol condensation is then transferred directly or via a washing and / or distillation stage into the hydrogenation apparatus.
  • the continuous mode of operation of the process according to the invention offers significant advantages in terms of safety and cost aspects for the industrial production of the compounds mentioned.
  • the aldol reaction is carried out in a conventional manner, in the context of the present invention, however, the stated solvents, catalysts, starting materials and process conditions are essential.
  • sterically demanding organic bases are used as basic catalysts.
  • the basic catalysts used are potassium or sodium hydroxide solution, in particular sodium hydroxide solution (5.8% strength).
  • suitable solvents are aliphatic, cycloaliphatic and aromatic d-do alcohols, as well as other inert solvents than the basic catalysts used.
  • the solvents used are C 1 -C 3 -alcohols, such as methanol or ethanol, in particular methanol.
  • solvent mixtures can also be used.
  • the aldol reaction is carried out in a variant of the present invention at elevated temperature, but scarce (about 5 to 10 ° C) below the boiling point of the solvent or solvent mixture, preferably 50 to 60 ° C, and at atmospheric pressure.
  • the aldol reaction can take place at an overpressure of up to 10 bar.
  • the aldehyde of the general formula II is used in excess.
  • the aldehyde of the general formula III is used in excess.
  • the aldehydes of the general formulas III and II are used in a molar ratio of 0.7: 1 to 1: 0.7, preferably in an equimolar ratio.
  • the aldehydes of the general formulas III and II are used in a molar ratio of between 1.2: 1 and 0.8: 1, preferably in an equimolar ratio.
  • the aldehydes of the general formulas II and III are used in a molar ratio of III: II between 1.4: 1 and 0.6: 1 and the reaction at a temperature of 45 to 55 ° C. in aqueous Reaction medium carried out, in this variant is subsequently preferably adjusted to a pH of 5 to 8.
  • the basic catalyst with the solvent for example methanol
  • the solvent for example methanol
  • the aldehydes II and III can be added either in an inflow, or in separate tributaries.
  • the aldehyde III and the basic catalyst are initially charged with solvent and the aldehyde II is added in the form of one or more feeds.
  • the aldehyde II and the basic catalyst are initially charged with solvent and the aldehyde III is added in the form of one or more feeds.
  • the aldehydes II and III are initially charged in solvent and then catalyst is added with or without further solvent.
  • the octenals obtained in the aldol reaction are then hydrogenated to the corresponding saturated aldehydes of the formula I.
  • Palladium catalysts on various supports such as carbon, alumina, silica gel or bauxite, in particular palladium on activated carbon, have proved particularly suitable for this selective hydrogenation step. Again, lower alcohols are advantageous solvents.
  • EP 0 798 039 A2 column 4, line 6 to column 5, line 11, the local examples 1 and 2s, and the local figures 1 to 3 described.
  • the hydrogenation can be carried out in one variant of the present invention.
  • the hydrogenation is carried out at 10 bar overpressure.
  • the hydrogenation is carried out in a bubble column.
  • the hydrogenation is carried out on a supported palladium catalyst, preferably palladium 0.5% of activated carbon.
  • the hydrogenation is carried out at 10 bar overpressure in a bubble column on a supported palladium catalyst, preferably palladium 0.5% of activated carbon.
  • the hydrogenation catalyst may be suspended in liquid, in another variant, the hydrogenation catalyst may also be immobilized.
  • the hydrogenation can also be divided into a main hydrogenation and a posthydrogenation.
  • a preferred variant of the present invention is the following process:
  • solvent preferably methanol and / or ethanol, in particular methanol
  • basic catalyst preferably alkali metal hydroxide, particularly preferably aqueous NaOH, if appropriate together with solvent, preferably methanol and / or ethanol, in particular methanol
  • a hydrogenation apparatus preferably hydrogenation autoclave or bubble column, in particular bubble column,
  • a hydrogenation catalyst preferably palladium catalyst, in particular 0.5% palladium on activated carbon
  • R 1 , R 2 and X are each as defined above,
  • step g) is carried out continuously.
  • Methods according to the steps of separation and recycling of unconsumed aldehyde II for reuse in the inventive method.
  • the methods comprise the separation and recycling of unused aldehyde III for reuse in the methods of the invention.
  • the processes accordingly comprise the separation and recycling of unused aldehydes II and III for reuse in the processes of the invention.
  • the aldehydes prepared by the process according to the invention can advantageously be used as fragrances or constituents of fragrance compositions and perfume oils for cosmetic applications. Of importance is also that they can be easily prepared from readily available starting materials.
  • isononanal and propanal are reacted in the context of the present invention, not only the main product DH-Lyrisal but also iso-DH-Lyrisal or, after the hydrogenation, in addition to lyyrisal, iso-Lyrisal can also be formed according to the following scheme.
  • Example 1 comparative example
  • a mixture was obtained which had the following composition: 46.9% by weight of methanol; 0.1% by weight of propionaldehyde; 1% by weight of 2-methylpentenal; 9.4% by weight of isononanal; 22.6% by weight of 2,5,7,7-tetramethyl-oct-2-enal (DH-Lyrisal); 0.4% by weight 2,4,7,9,9-pentamethyl deca-2,4-dienal; 5.6% by weight of 5,7,7-trimethyl-2- (1,3,3-trimethyl-butyl) -oct-2-enal (NONADI), 12.9% by weight of water, a content of 1, 1 wt .-% accounts for other by-products.
  • the proportion of by-products (NONADI, methylpentenal, 2,4,7,9,9-pentamethyl-deca-2,4-dienal) was 0.31 kg per kg of valuable product DH-Lyrisal.
  • a mixture was obtained which had the following composition: 47.5% by weight of methanol; 0% by weight of propionaldehyde; 1.5% by weight of 2-methylpentenal; 7% by weight of isononanal; 23.1% by weight of 2,5,7,7-tetramethyl-oct-2-enal (DH-Lyrisal); 0.6% by weight 2,4,7,9,9-pentamethyl deca-2,4-dienal; 4.9 wt .-% 5,7,7-trimethyl-2- (1,3,3-trimethyl-butyl) -oct-2-enal (NONADI), 13.7 wt .-% water, a proportion of 1, 7 wt .-% accounts for other by-products.
  • the proportion of by-products (NONADI, methyl pentenal, 2,4,7,9,9-pentamethyl deca-2,4-dienal) was 0.30 kg per kg value product DH-Lyrisal.
  • a mixture was obtained which had the following composition: 47.5% by weight of methanol; 0.1% by weight of propionaldehyde; 2.1% by weight of 2-methylpentenal; 5.4% by weight of isononanal; 22.1% by weight of 2,5,7,7-tetramethyl-oct-2-enal (DH-Lyrisal); 0.4% by weight 2,4,7,9,9-pentamethyl deca-2,4-dienal; 4.2% by weight of 5,7,7-trimethyl-2- (1,3,3-trimethyl-butyl) -oct-2-enal (NONADI), a proportion of 18.2% by weight being accounted for Water and other by-products.
  • the proportion of by-products was 0.30 kg per kg value product DH-Lyrisal.
  • a mixture was obtained which had the following composition: 46.8% by weight of methanol; 0.1% by weight of propionaldehyde; 2.7% by weight of 2-methylpentenal; 4.3% by weight of isononanal; 22.4% by weight of 2,5,7,7-tetramethyl-oct-2-enal (DH-Lyrisal); 0.7% by weight 2,4,7,9,9-pentamethyl deca-2,4-dienal; 4.3 wt .-% 5,7,7-trimethyl-2- (1, 3,3-trimethyl-butyl) -oct-2-enal (NONADI), a share of 18.7 wt .-% accounts for Water and other by-products. The proportion of by-products (NONADI, methylpentenal, 2,4,7,9,9-pentamethyl deca-2,4-dienal) was 0.35 kg per kg of product value DH-Lyrisal.
  • a mixture was obtained which had the following composition: 45.8% by weight of methanol; 0.3% by weight of propionaldehyde; 4.5% by weight of 2-methylpentenal; 2.5% by weight of isononanal; 19.4% by weight of 2,5,7,7-tetramethyl-oct-2-enal (DH-Lyrisal); 0.9% by weight 2,4,7,9,9-pentamethyl deca-2,4-dienal; 3.7% by weight of 5,7,7-trimethyl-2- (1,3,3-trimethyl-butyl) -oct-2-enal (NONADI), 15.4% by weight of water, a content of 7.5% by weight is accounted for by other by-products.
  • the proportion of by-products (NONADI, methylpentenal, 2,4,7,9,9-pentamethyl deca-2,4-dienal) was 0.47 kg per kg of product DH-Lyrisal.
  • Example 1 The product of Examples 1 to 6 was passed directly into a hydrogenation plant, wherein the hydrogenation was divided into a main and a subsequent subsequent hydrogenation, wherein the discharge from the main hydrogenation directly into the post-hydrogenation, without further work-up or isolation was driven.
  • the main hydrogenation was carried out in a bubble column on a 0.5% palladium / carbon catalyst at 10 to 12 bar, 80 to 85 ° C and a significant excess amount of hydrogen and the post-hydrogenation in a bubble column on a 0.5% palladium / activated carbon catalyst at 20 to 30 bar, 150 to 200 ° C and a significant excess amount of hydrogen.
  • Example 8 The procedure was carried out as in Example 8, it was only interposed between the aldol condensation and the hydrogenation, a washing with acetic acid and distilled water and a fractional distillation.
  • Example 10 comparative example analogous to Example 1 of EP 0 252 378 A1:

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de préparation d'aldéhydes aliphatiques de formule générale (I) par réaction d'aldéhyde de formule générale (II) avec un aldéhyde de formule générale (III), formules dans lesquelles R1 représente hydrogène ou un groupe méthyle, R2 représente un radical alkyle linéaire ou ramifié ayant 1 à 4 atomes de carbone et les deux X représentent chacun hydrogène ou ensemble une autre liaison C-C, en présence d'un catalyseur de condensation aldolique pour obtenir l'octénal substitué de formule générale (I) puis éventuellement par hydrogénation continue ou discontinue pour obtenir l'octanal correspondant de formule (I), ledit procédé étant caractérisé en ce que les aldéhydes des formules générales III et Il sont utilisés dans un rapport molaire III:II compris entre 1,4:1 et 0,6:1.
PCT/EP2010/068865 2009-12-04 2010-12-03 Procédé de préparation d'aldéhydes aliphatiques WO2011067386A2 (fr)

Applications Claiming Priority (2)

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EP09178052.8 2009-12-04
EP09178052 2009-12-04

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WO2011067386A3 WO2011067386A3 (fr) 2011-10-13

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8367875B2 (en) 2010-02-11 2013-02-05 Basf Se Process for the preparation of m-substituted alkyltoluenes by isomerization with ionic liquids as catalysts
US8609903B2 (en) 2010-04-01 2013-12-17 Basf Se Process for preparing hydroxy-substituted aromatic aldehydes
US8889920B2 (en) 2010-02-12 2014-11-18 Basf Se Process for preparing 4-isopropylcyclohexylmethanol
WO2016007823A1 (fr) * 2014-07-10 2016-01-14 Mallinckrodt Llc Procédé pour préparer des phénylalcanes substitués
CN112105597A (zh) * 2018-05-11 2020-12-18 高砂香料工业株式会社 二烯醛化合物和香料组合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0252378A1 (fr) 1986-07-05 1988-01-13 BASF Aktiengesellschaft Aldéhydes aliphatiques, procédé pour leur fabrication et leur utilisation comme odoriférants
EP0798039A2 (fr) 1996-03-26 1997-10-01 Basf Aktiengesellschaft Procédé de réacteur pour la mise en oeuvre de la transformation de substances au moyen de catalyseurs en suspension dans des liquides
WO2004007414A1 (fr) 2002-07-15 2004-01-22 Basf Aktiengesellschaft Procede d'hydrogenation continue de citral permettant l'obtention de citronellal

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0252378A1 (fr) 1986-07-05 1988-01-13 BASF Aktiengesellschaft Aldéhydes aliphatiques, procédé pour leur fabrication et leur utilisation comme odoriférants
EP0798039A2 (fr) 1996-03-26 1997-10-01 Basf Aktiengesellschaft Procédé de réacteur pour la mise en oeuvre de la transformation de substances au moyen de catalyseurs en suspension dans des liquides
WO2004007414A1 (fr) 2002-07-15 2004-01-22 Basf Aktiengesellschaft Procede d'hydrogenation continue de citral permettant l'obtention de citronellal

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
W.R. GRAMLICH; H. SIEGEL: "Tetramethyloctanal und Derivate - eine neue Riechstoffklasse", LIEBIGS ANN. CHEM., 1988, pages 487 - 489

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8367875B2 (en) 2010-02-11 2013-02-05 Basf Se Process for the preparation of m-substituted alkyltoluenes by isomerization with ionic liquids as catalysts
US8889920B2 (en) 2010-02-12 2014-11-18 Basf Se Process for preparing 4-isopropylcyclohexylmethanol
US8609903B2 (en) 2010-04-01 2013-12-17 Basf Se Process for preparing hydroxy-substituted aromatic aldehydes
WO2016007823A1 (fr) * 2014-07-10 2016-01-14 Mallinckrodt Llc Procédé pour préparer des phénylalcanes substitués
US9556108B2 (en) 2014-07-10 2017-01-31 Mallinckrodt Llc Process for preparing substituted phenylalkanes
CN112105597A (zh) * 2018-05-11 2020-12-18 高砂香料工业株式会社 二烯醛化合物和香料组合物

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