EP1294667A1 - Method for producing aldehydes - Google Patents

Method for producing aldehydes

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Publication number
EP1294667A1
EP1294667A1 EP01953986A EP01953986A EP1294667A1 EP 1294667 A1 EP1294667 A1 EP 1294667A1 EP 01953986 A EP01953986 A EP 01953986A EP 01953986 A EP01953986 A EP 01953986A EP 1294667 A1 EP1294667 A1 EP 1294667A1
Authority
EP
European Patent Office
Prior art keywords
range
dehydrogenation
alcohol
aldehydes
fatty alcohols
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.)
Withdrawn
Application number
EP01953986A
Other languages
German (de)
French (fr)
Inventor
Albrecht Schwerin
Gerrit Pelzer
Lothar Friesenhagen
Bernhard Gutsche
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.)
Cognis IP Management GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
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 Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1294667A1 publication Critical patent/EP1294667A1/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation

Definitions

  • the invention is in the field of fragrances and relates to a new process for the production of fatty aldehydes.
  • Lower aldehydes such as 1-octanal or 1-decanal, are renowned raw materials for the fragrance industry.
  • Their production based on fatty alcohols is known from the prior art, for example by oxidation with hypochlorite in the presence of 4-ethoxy-2,2,6,6 -tetramethylpiperidin-l-yloxyl ("Tempo") is known.
  • the air oxidation of the alcohols can take place in the presence of ruthenium or platinum catalysts.
  • unsaturated alcohols can be isomerized to aldehydes under the influence of one-pentacarbonyl.
  • the fatty acids are obtained from fatty acids Aldehydes by hydrogenation on oxidic copper catalysts of the Adkins type or by reaction with peracids in the presence of titanium (IV) oxide
  • oxidic copper catalysts of the Adkins type or by reaction with peracids in the presence of titanium (IV) oxide
  • EP 0320074 AI Engelhard proposes copper catalysts doped with iron for the same purpose
  • Rosenmund reaction in which acid chlorides are hydrogenated on Lindlar catalysts to the corresponding aldehydes.
  • the known processes have the disadvantage that they are technically complex, produce low yields and / or are characterized by unsatisfactory selectivities. Accordingly, the object of the present invention was to provide a new method which reliably avoids the disadvantages of the prior art mentioned. Description of the invention
  • the invention relates to a process for the preparation of aldehydes, in which fatty alcohols are continuously dehydrogenated in the presence of oxidic copper / zinc catalysts at temperatures in the range from 200 to 280 ° C. and pressures in the range from 10 mbar to 1 bar.
  • Suitable starting materials for the process according to the invention are linear or branched, saturated or unsaturated primary alcohols, which for the sake of simplicity are summarized under the name fatty alcohols and preferably follow the formula (I) in which
  • R 1 represents a linear or branched saturated or unsaturated alkyl and / or alkenyl radical having 6 to 22, preferably 8 to 12 and in particular 8 to 10 carbon atoms.
  • Typical examples are caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, Caprinalko- alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl rylalkohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl, ünolylalkohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, Eru - Cyl alcohol and brassidyl alcohol and their technical mixtures, which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldeh
  • the fatty aldehydes are preferably produced in a shaft reactor with a fixed catalyst bed.
  • the oxidic copper / zinc catalysts are commercial Adkins contacts, ie solids with a spinel structure, which preferably contain chromium, cadmium, cerium, barium, silicon and / or aluminum as further metal components. Basic copper / zinc / aluminum oxides are particularly preferred.
  • the reaction usually takes place at temperatures in the range from 200 to 280, preferably 240 to 260 ° C.
  • the dehydrogenation is carried out either without pressure or at a reduced pressure in the range of preferably 20 to 40 mbar.
  • the liquid hour space velocity (LHSV) can be in the range from 1 to 3, preferably 1.1 to 2.6 h "1.
  • the yield of fatty aldehydes is in the range of at least 60 and preferably 65 to 70% of theory, while the selectivity is at least 90 and preferably 95 to 98% It is advisable to carry out the dehydrogenation in the presence of nitrogen as the carrier gas.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention relates to a method for producing aldehydes. Said method consists of continuously dehydrating fatty alcohols in the presence of oxidic copper/zinc catalysts, at temperatures ranging between 200 and 280 °C and pressures ranging between 10 mbar and 1 bar.

Description

Verfahren zur Herstellung von AldehydenProcess for the preparation of aldehydes
Gebiet der ErfindungField of the Invention
Die Erfindung befindet sich auf dem Gebiet der Riechstoffe und betrifft ein neues Verfahren zur Herstellung von Fettaldehyden.The invention is in the field of fragrances and relates to a new process for the production of fatty aldehydes.
Stand der TechnikState of the art
Niedere Aldehyde, wie beispielsweise 1-Octanal oder 1-Decanal stellen begehrte Rohstoffe für die Riechstoffindustrie dar. Ihre Herstellung ausgehend von Fettalkoholen ist aus dem Stand der Technik beispielsweise durch Oxidation mit Hypochlorit in Gegenwart von 4- ethoxy-2,2,6,6-tetramethylpiperidin-l-yloxyl („Tempo") bekannt. Die Luftoxidation der Alkohole kann in Gegenwart von Ruthen- oder Platin-Katalysatoren erfolgen. Des weiteren lassen sich ungesättigte Alkohole unter dem Einfluß von Einsenpentacarbonyl zu Aldehyden isomerisieren. Ausgehend von Fettsäuren erhält man die Aldehyde durch Hydrierung an oxidischen Kupferkatalysatoren vom Adkins-Typ oder durch Umsetzung mit Persäuren in Gegenwart von Titan(IV)oxid. Über den Einsatz von heterogenen oxidischen Kupferkatalysatoren zur Dehydrierung von Fettalkoholen wird in RO 0111820 (Comb.Chim.Rimnicu Vilcea) berichtet. In der EP 0320074 AI (Engelhard) werden für den gleichen Zweck mit Eisen dotierte Kupferkatalysatoren vorgeschlagen. Eine klassische Methode stellt die Rosenmund- Reaktion dar, bei der man Säurechloride an Lindlar-Katalysatoren zu den entsprechenden Aldehyden hydriert. In diesem Zusammenhang sei auf die Übersichtsartikel in J.Am.Chem.Soc. 109, 3786 (1987), J.Org.Chem. 52, 2259 (1987) und Tetrahedron Lett. 28, 4575 (1987) hingewiesen.Lower aldehydes, such as 1-octanal or 1-decanal, are coveted raw materials for the fragrance industry. Their production based on fatty alcohols is known from the prior art, for example by oxidation with hypochlorite in the presence of 4-ethoxy-2,2,6,6 -tetramethylpiperidin-l-yloxyl ("Tempo") is known. The air oxidation of the alcohols can take place in the presence of ruthenium or platinum catalysts. Furthermore, unsaturated alcohols can be isomerized to aldehydes under the influence of one-pentacarbonyl. The fatty acids are obtained from fatty acids Aldehydes by hydrogenation on oxidic copper catalysts of the Adkins type or by reaction with peracids in the presence of titanium (IV) oxide The use of heterogeneous oxidic copper catalysts for the dehydrogenation of fatty alcohols is reported in RO 0111820 (Comb.Chim.Rimnicu Vilcea) EP 0320074 AI (Engelhard) proposes copper catalysts doped with iron for the same purpose A classic method is the Rosenmund reaction, in which acid chlorides are hydrogenated on Lindlar catalysts to the corresponding aldehydes. In this context, reference is made to the review articles in J.Am.Chem.Soc. 109, 3786 (1987), J.Org.Chem. 52, 2259 (1987) and Tetrahedron Lett. 28, 4575 (1987).
Die bekannten Verfahren weisen jedoch den Nachteil auf, dass sie technisch aufwendig sind, niedrige Ausbeuten erbringen und/oder sich durch unbefriedigende Selektivitäten auszeichnen. Die Aufgabe der vorliegenden Erfindung hat dem entsprechend darin bestanden, ein neues Verfahren zur Verfügung zu stellen, welche die genannten Nachteile des Stands der Technik zuverlässig vermeidet. Beschreibung der ErfindungHowever, the known processes have the disadvantage that they are technically complex, produce low yields and / or are characterized by unsatisfactory selectivities. Accordingly, the object of the present invention was to provide a new method which reliably avoids the disadvantages of the prior art mentioned. Description of the invention
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Aldehyden, bei dem man Fettalkohole in Gegenwart von oxidischen Kupfer/Zink-Katalysatoren bei Temperaturen im Bereich von 200 bis 280 °C und Drücken im Bereich von 10 mbar bis 1 bar kontinuierlich dehydriert.The invention relates to a process for the preparation of aldehydes, in which fatty alcohols are continuously dehydrogenated in the presence of oxidic copper / zinc catalysts at temperatures in the range from 200 to 280 ° C. and pressures in the range from 10 mbar to 1 bar.
Überraschenderweise wurde gefunden, dass unter Einsatz der genannten Katalysatoren die kontinuierlich Dehydrierung von Fettalkoholen zu Fettaldehyden in Ausbeuten oberhalb von 60 und mit Selektivitäten oberhalb von 90 % der Theorie gelingt.Surprisingly, it was found that, using the catalysts mentioned, the continuous dehydrogenation of fatty alcohols to fatty aldehydes succeeds in yields above 60% and with selectivities above 90% of theory.
Fettalkoholefatty alcohols
Als Einsatzstoffe für das erfindungsgemäße Verfahren eignen sich lineare oder verzweigte, gesättigte oder ungesättigte primäre Alkohole, die der Einfachheit halber unter der Bezeichnung Fettalkohole zusammengefaßt werden und vorzugsweise der Formel (I) folgen, in derSuitable starting materials for the process according to the invention are linear or branched, saturated or unsaturated primary alcohols, which for the sake of simplicity are summarized under the name fatty alcohols and preferably follow the formula (I) in which
RJOH (I)R J OH (I)
in der R1 für einen linearen oder verzweigten gesättigten oder ungesättigten Alkyl- und/oder Alkenylrest mit 6 bis 22, vorzugsweise 8 bis 12 und insbesondere 8 bis 10 Kohlenstoffatomen steht. Typische Beispiele sind Capronalkohol, Caprylalkohol, 2-Ethylhexylalkohol, Caprinalko- hol, Laurylalkohol, Isotridecylalkohol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stea- rylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, ünolylalkohol, Linolenylalkohol, Elaeostearylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol, Eru- cylalkohol und Brassidylalkohol sowie deren technische Mischungen, die z.B. bei der Hochdruckhydrierung von technischen Methylestern auf Basis von Fetten und Ölen oder Aldehyden aus der Roelen'schen Oxosynthese sowie als Monomerfraktion bei der Dimerisierung von ungesättigten Fettalkoholen anfallen. Bevorzugt ist der Einsatz von Caprylalkohol (1- Octanol), 2-Ethylhexanol und Caprinalkohol (1-Decanol) sowie deren Mischungen. Synthesein which R 1 represents a linear or branched saturated or unsaturated alkyl and / or alkenyl radical having 6 to 22, preferably 8 to 12 and in particular 8 to 10 carbon atoms. Typical examples are caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, Caprinalko- alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl rylalkohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl, ünolylalkohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, Eru - Cyl alcohol and brassidyl alcohol and their technical mixtures, which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols. The use of caprylic alcohol (1-octanol), 2-ethylhexanol and capric alcohol (1-decanol) and mixtures thereof is preferred. synthesis
Die Herstellung der Fettaldehyde findet vorzugsweise in einem Schachtreaktor mit Katalysatorfestbett statt. Bei den oxidischen Kupfer/Zink-Katalysatoren handelt es sich um kommerzielle Adkins-Kontakte, d.h. Feststoffe mit Spinellstruktur, die vorzugsweise als weitere Metallkomponenten Chrom, Cadmium, Cer, Barium, Silicium und/oder Aluminium enthalten. Besonders bevorzugt sind basische Kupfer/Zink/Aluminiumoxide. Üblicherweise findet die Reaktion bei Temperaturen im Bereich von 200 bis 280, vorzugsweise 240 bis 260 °C statt. Die Dehydrierung erfolgt entweder drucklos oder aber bei einem vermindertem Druck im Bereich von vorzugsweise 20 bis 40 mbar. Dabei kann die Liquid Hour Space Velocity (LHSV) im Bereich von 1 bis 3, vorzugsweise 1,1 bis 2,6 h"1 liegen. Die Ausbeute an Fettaldehyden liegt im Bereich von mindestens 60 und vorzugsweise 65 bis 70 % der Theorie, während die Selektivität mindestens 90 und vorzugsweise 95 bis 98 % beträgt. Es empfiehlt sich die Dehydrierung in Gegenwart von Stickstoff als Trägergas durchzuführen. The fatty aldehydes are preferably produced in a shaft reactor with a fixed catalyst bed. The oxidic copper / zinc catalysts are commercial Adkins contacts, ie solids with a spinel structure, which preferably contain chromium, cadmium, cerium, barium, silicon and / or aluminum as further metal components. Basic copper / zinc / aluminum oxides are particularly preferred. The reaction usually takes place at temperatures in the range from 200 to 280, preferably 240 to 260 ° C. The dehydrogenation is carried out either without pressure or at a reduced pressure in the range of preferably 20 to 40 mbar. The liquid hour space velocity (LHSV) can be in the range from 1 to 3, preferably 1.1 to 2.6 h "1. The yield of fatty aldehydes is in the range of at least 60 and preferably 65 to 70% of theory, while the selectivity is at least 90 and preferably 95 to 98% It is advisable to carry out the dehydrogenation in the presence of nitrogen as the carrier gas.
BeispieleExamples
In einem kontinuierlichen Druckreaktor mit oxidischem Katalysatorfestbett wurden Fettalkohole bei einer Temperatur von 250 °C und Drücken im Bereich von 20 mbar bis Normaldruck zu den entsprechenden Aldehyden dehydriert. Die Versuchsergebnisse sind in Tabelle 1 zusammengefaßt. Die Aldehyde wurden in Ausbeuten von 60 bis 70 % und Selektivitäten von mehr als 90 % der Theorie erhalten.In a continuous pressure reactor with an oxidic fixed catalyst bed, fatty alcohols were dehydrogenated to the corresponding aldehydes at a temperature of 250 ° C. and pressures in the range from 20 mbar to normal pressure. The test results are summarized in Table 1. The aldehydes were obtained in yields of 60 to 70% and selectivities of more than 90% of theory.
Tabelle 1Table 1
Kontinuierliche Dehydrierung von FettalkoholenContinuous dehydration of fatty alcohols
1) Leuna-Katalysator 1962 1) Leuna catalyst 1962

Claims

Patentansprüche claims
1. Verfahren zur Herstellung von Aldehyden, bei dem man Fettalkohole in Gegenwart von oxidischen Kupfer/Zink-Katalysatoren bei Temperaturen im Bereich von 200 bis 280 °C und Drücken im Bereich von 10 mbar bis 1 bar kontinuierlich dehydriert.1. Process for the preparation of aldehydes, in which fatty alcohols are continuously dehydrogenated in the presence of oxidic copper / zinc catalysts at temperatures in the range from 200 to 280 ° C. and pressures in the range from 10 mbar to 1 bar.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man Fettalkohole der Formel (I) einsetzt,2. The method according to claim 1, characterized in that fatty alcohols of the formula (I) are used,
RxOH (I)R x OH (I)
in der R1 für einen linearen oder verzweigten gesättigten oder ungesättigten Alkyl- und/oder Alkenylrest mit 6 bis 22 Kohlenstoffatomen steht.in which R 1 represents a linear or branched saturated or unsaturated alkyl and / or alkenyl radical having 6 to 22 carbon atoms.
3. Verfahren nach den Ansprüchen 1 und/oder 2, dadurch gekennzeichnet, dass man Kupfer/Zink-Katalysatoren einsetzt, welche als weitere Metallkomponenten Chrom, Cadmium, Cer, Barium, Silicium und/oder Aluminium enthalten.3. Process according to claims 1 and / or 2, characterized in that copper / zinc catalysts are used which contain chromium, cadmium, cerium, barium, silicon and / or aluminum as further metal components.
4. Verfahren nach mindestens einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass man die Katalysatoren in einem Festbett anordnet.4. The method according to at least one of claims 1 to 3, characterized in that the catalysts are arranged in a fixed bed.
5. Verfahren nach mindestens einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass man die Dehydrierung bei Temperaturen im Bereich von 240 bis 260 °C durchführt.5. The method according to at least one of claims 1 to 4, characterized in that one carries out the dehydrogenation at temperatures in the range from 240 to 260 ° C.
6. Verfahren nach mindestens einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass man die Dehydrierung bei Drücken im Bereich von 20 bis 40 mbar durchführt.6. The method according to at least one of claims 1 to 5, characterized in that the dehydrogenation is carried out at pressures in the range from 20 to 40 mbar.
7. Verfahren nach mindestens einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass man die Dehydrierung bei einer Liquid Hourly Space Velocity (LHSV) vom 1 bis 3 h"1 durchführt.7. The method according to at least one of claims 1 to 6, characterized in that one carries out the dehydrogenation at a liquid hourly space velocity (LHSV) from 1 to 3 h "1 .
8. Verfahren nach mindestens einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass man die Dehydrierung in Gegenwart von Stickstoff als Trägergas durchführt. 8. The method according to at least one of claims 1 to 7, characterized in that one carries out the dehydrogenation in the presence of nitrogen as a carrier gas.
EP01953986A 2000-06-28 2001-06-19 Method for producing aldehydes Withdrawn EP1294667A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10044809A DE10044809A1 (en) 2000-06-28 2000-06-28 Process for the preparation of aldehydes
DE10044809 2000-06-28
PCT/EP2001/006859 WO2002000581A1 (en) 2000-06-28 2001-06-19 Method for producing aldehydes

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US (1) US6897342B2 (en)
EP (1) EP1294667A1 (en)
JP (1) JP2004501881A (en)
DE (1) DE10044809A1 (en)
IL (1) IL153607A0 (en)
WO (1) WO2002000581A1 (en)

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US7888542B2 (en) * 2005-12-12 2011-02-15 Neste Oil Oyj Process for producing a saturated hydrocarbon component
US7998339B2 (en) * 2005-12-12 2011-08-16 Neste Oil Oyj Process for producing a hydrocarbon component
US7850841B2 (en) * 2005-12-12 2010-12-14 Neste Oil Oyj Process for producing a branched hydrocarbon base oil from a feedstock containing aldehyde and/or ketone
US8053614B2 (en) * 2005-12-12 2011-11-08 Neste Oil Oyj Base oil
JP5143438B2 (en) 2007-01-31 2013-02-13 花王株式会社 Reaction device
WO2011048783A1 (en) * 2009-10-23 2011-04-28 出光興産株式会社 Process for production of ketone
JP2014009167A (en) * 2012-06-27 2014-01-20 Kao Corp Process for producing aldehyde
EP2868646B1 (en) * 2012-06-27 2019-07-24 Kao Corporation Method for producing aldehyde
JP6627219B2 (en) * 2015-01-05 2020-01-08 株式会社Ihi Olefin production method
CN106588957B (en) * 2016-12-07 2019-04-05 苏州大学 A kind of monovalence copper compound and the preparation method and application thereof based on nitrogen-containing heterocycle mercaptan ligand

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DE2358254C3 (en) * 1973-11-22 1978-10-05 Wacker-Chemie Gmbh, 8000 Muenchen Process for the production of aldehydes or ketones by the catalytic dehydrogenation of alcohols
JPS50130708A (en) * 1974-04-04 1975-10-16
SU572450A1 (en) * 1976-01-04 1977-09-15 Предприятие П/Я В-2609 Device for coiling carriers of tuna tier
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See references of WO0200581A1 *

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IL153607A0 (en) 2003-07-06
WO2002000581A1 (en) 2002-01-03
US20040002620A1 (en) 2004-01-01
DE10044809A1 (en) 2002-01-10
JP2004501881A (en) 2004-01-22
US6897342B2 (en) 2005-05-24

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