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DE1132909B - Process for the production of aldehydes and ketones - Google Patents

Process for the production of aldehydes and ketones

Info

Publication number
DE1132909B
DE1132909B DEC17731A DEC0017731A DE1132909B DE 1132909 B DE1132909 B DE 1132909B DE C17731 A DEC17731 A DE C17731A DE C0017731 A DEC0017731 A DE C0017731A DE 1132909 B DE1132909 B DE 1132909B
Authority
DE
Germany
Prior art keywords
ketones
aldehydes
olefins
production
bell
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.)
Pending
Application number
DEC17731A
Other languages
German (de)
Inventor
Dipl-Ing Walter Fritz
Dipl-Ing Hugo Kojer
Dr Jobst Possberg
Dr Juergen Smidt
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.)
Consortium fuer Elektrochemische Industrie GmbH
Original Assignee
Consortium fuer Elektrochemische Industrie GmbH
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 Consortium fuer Elektrochemische Industrie GmbH filed Critical Consortium fuer Elektrochemische Industrie GmbH
Priority to DEC17731A priority Critical patent/DE1132909B/en
Priority to GB36263/59A priority patent/GB930143A/en
Publication of DE1132909B publication Critical patent/DE1132909B/en
Pending legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
    • B01J31/30—Halides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
    • B01J31/403—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing iron group metals or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
    • B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Verfahren zur Herstellung von Aldehyden und Ketonen In der deutschen Patentschrift 1080 994 und in der indischen Patentschrift 65530 sind Verfahren zur Herstellung von Aldehyden und Ketonen durch Umsetzung von Olefinen mit wäßrigen Katalysatorlösungen, welche Palladiumsalze und Kupferchlorid enthalten, beschrieben. Process for the production of aldehydes and ketones In the German Patent specification 1080 994 and Indian patent specification 65530 are methods for Production of aldehydes and ketones by reacting olefins with aqueous ones Catalyst solutions which contain palladium salts and copper chloride are described.

Besonders bei Verwendung von Ausgangsolefinen, die noch Beimengungen wie z. B. Stickstoff, Wasserstoff oder gasförmige gesättigte Kohlenwasserstoffe enthalten, erfordert eine vollständige Umsetzung der Olefine bei einmaligem Durchgang durch das Reaktionsgefäß unverhältnismäßig lange Verweilzeiten. Especially when using starting olefins that still contain additives such as B. nitrogen, hydrogen or gaseous saturated hydrocarbons requires complete conversion of the olefins in a single pass due to the reaction vessel disproportionately long residence times.

Diese führen zu einer erhöhten Bildung von Nebenprodukten wie z. B. Kohlendioxyd, Methylchlorid und Athylchlorid.These lead to an increased formation of by-products such. B. Carbon dioxide, methyl chloride and ethyl chloride.

Es wurde nun ein Verfahren zur Herstellung von Aldehyden und Ketonen durch Umsetzung von Olefinen mit wäßrigen Katalysatorlösungen, welche Palladiumsalze und Kupferchlorid enthalten, gefunden, bei dem man die das Reaktionsgefäß verlassenden, noch nicht umgesetzte Olefine enthaltenden Abgase in einer eigenen Reaktionsvorrichtung, in die zweckmäßig ein oder mehrere Böden glockenbodenartig eingebaut sind, mit frischer Katalysatorlösung umsetzt. There has now been a process for making aldehydes and ketones by reacting olefins with aqueous catalyst solutions, which are palladium salts and copper chloride, found, in which one leaves the reaction vessel, off-gases containing not yet converted olefins in a separate reaction device, In the expedient one or more trays are built in like a bell-bottom, with fresher Reacts catalyst solution.

Auf diese Weise gelingt es, die Bildung von Nebenprodukten zurückzudrängen und eine praktisch vollständige Ausnutzung der Ausgangsolefine zu erreichen. In this way it is possible to suppress the formation of by-products and to achieve a practically complete utilization of the starting olefins.

Dies trifft auch für die Verwendung verhältnismäßig reiner Olefine zu.This also applies to the use of relatively pure olefins to.

Der Einbau von glockenbodenartigen Böden in die Abgasreaktionsvorrichtung vermindert die Rückdiffusion der inerten Beimengungen und gewährleistet eine besonders rationelle Umsetzung der Olefine. The incorporation of bell-bottom trays in the exhaust gas reaction device reduces the back diffusion of the inert admixtures and ensures a special one efficient implementation of olefins.

Beispiel Als Reaktionsgefäß wird ein Füllkörperturm von 5 m Höhe und 30 cm Durchmesser verwendet. Bei 8 atü und 1000 C werden in diesem Turm stündlich 17 Ncbm Frischgas (98,8o Äthylen) und 6 cbm Katalysatorlösung (0,01 Mol Palladium, 1,4 Mol Kupfer und 2,5 Mol Chlorid im Liter) im Gegenstrom geführt. Es werden 27,6 kg Acetaldehyd in der Stunde entsprechend einer Ausbeute von 84°/o, bezogen auf eingesetztes Äthylen, erzeugt. Eine Erhöhung des Turms auf 9 m bringt eine Verbesserung der Ausbeute auf nur 89 °/o bei gleichzeitigem Rückgang der Raum-Zeit-Leistung von 78 g Aldehyd je Liter und Stunde auf 46 g. Example A packed tower with a height of 5 m is used as the reaction vessel and 30 cm in diameter. At 8 atü and 1000 C are in this tower every hour 17 Ncbm fresh gas (98.8o ethylene) and 6 cbm catalyst solution (0.01 mol palladium, 1.4 mol of copper and 2.5 mol of chloride per liter) in countercurrent. It will be 27.6 kg of acetaldehyde per hour corresponding to a yield of 84%, based on used ethylene. An increase in the tower to 9 m brings an improvement the yield to only 89 ° / o with a simultaneous decrease in the Space-time performance of 78 g of aldehyde per liter and hour to 46 g.

Leitet man dagegen das Abgas des 5 m hohen Turms in eine eigene Reaktionsvorrichtung (Füllkörperturm von 8 m Höhe und 12,5 cm Durchmesser), die mit frischer Katalysatorlösung beschickt wird, so steigt die Ausbeute auf 94°/o bei einer Raum-Zeit-Leistung von 68 g Aldehyd je Liter und Stunde. If, on the other hand, the exhaust gas from the 5 m high tower is fed into its own reaction device (Packing tower 8 m high and 12.5 cm in diameter) with fresh catalyst solution is charged, the yield increases to 94% with a space-time output of 68 g of aldehyde per liter and hour.

Durch Einbau eines Glockenbodens in das obere Drittel des Abgasreaktionsturms wird eine weitere Verbesserung der Ausbeute auf 95, 2°/o erzielt und das Äthylen praktisch vollständig umgesetzt. By installing a bell bottom in the upper third of the exhaust gas reaction tower a further improvement in the yield to 95.2% is achieved and the ethylene practically fully implemented.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Aldehyden und Ketonen durch Umsetzung von Olefinen mit wäßrigen Katalysatorlösungen, welche Palladiumsalze und Kupferchlorid enthalten, dadurch gekennzeichnet, daß man die das Reaktionsgefäß verlassenden, noch nicht umgesetzte Olefine enthaltenden Abgase in einer eigenen Reaktionsvorrichtung, in die zweckmäßig ein oder mehrere Böden glockenbodenartig eingebaut sind, mit frischer Katalysatorlösung umsetzt. PATENT CLAIM: Process for the production of aldehydes and ketones by reacting olefins with aqueous catalyst solutions, which are palladium salts and contain copper chloride, characterized in that the reaction vessel leaving exhaust gases containing unreacted olefins in a separate one Reaction device in which one or more trays are expediently bell-bottomed are installed, reacted with fresh catalyst solution.
DEC17731A 1958-10-24 1958-10-24 Process for the production of aldehydes and ketones Pending DE1132909B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEC17731A DE1132909B (en) 1958-10-24 1958-10-24 Process for the production of aldehydes and ketones
GB36263/59A GB930143A (en) 1958-10-24 1959-10-26 Method of and apparatus for the manufacture of aldehydes or ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC17731A DE1132909B (en) 1958-10-24 1958-10-24 Process for the production of aldehydes and ketones

Publications (1)

Publication Number Publication Date
DE1132909B true DE1132909B (en) 1962-07-12

Family

ID=7016299

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC17731A Pending DE1132909B (en) 1958-10-24 1958-10-24 Process for the production of aldehydes and ketones

Country Status (2)

Country Link
DE (1) DE1132909B (en)
GB (1) GB930143A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4008279A (en) * 1974-08-15 1977-02-15 Celanese Corporation Process for dehalogenation and/or prevention of halogenation
US4190606A (en) * 1976-06-17 1980-02-26 Celanese Corporation Process for dehalogenation and/or prevention of halogenation

Also Published As

Publication number Publication date
GB930143A (en) 1963-07-03

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