DE408811C - Process for the catalytic hydrogenation and dehydrogenation of organic compounds - Google Patents

Process for the catalytic hydrogenation and dehydrogenation of organic compounds

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Publication number
DE408811C
DE408811C DEB109165D DEB0109165D DE408811C DE 408811 C DE408811 C DE 408811C DE B109165 D DEB109165 D DE B109165D DE B0109165 D DEB0109165 D DE B0109165D DE 408811 C DE408811 C DE 408811C
Authority
DE
Germany
Prior art keywords
dehydrogenation
organic compounds
catalytic hydrogenation
alloys
contact
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.)
Expired
Application number
DEB109165D
Other languages
German (de)
Inventor
Dr Adam Bertsch
Dr Otto Schmidt
Dr Hans Ufer
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB109165D priority Critical patent/DE408811C/en
Application granted granted Critical
Publication of DE408811C publication Critical patent/DE408811C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
    • C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • C07C29/154—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing copper, silver, gold, or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Description

Verfahren zur katalytischen Hydrierung und Dehydrierung organischer Verbindungen. Es hat sich gezeigt, daß man organische Verbindungen besonders leicht katalytisch hydrieren bzw. dehydrieren kann, wenn man Katalysatoren verwendet, die aus solchen Legierungen entstehen, die bei der Darstellung des Kontakts oder seiner Verwendung zerfallen. Unter Umständen kann während der Verwendung des Kontakts die Legierung intermediär zurückgebildet werden.Process for the catalytic hydrogenation and dehydrogenation of organic Links. It has been shown that organic compounds are particularly easy to use can catalytically hydrogenate or dehydrogenate when using catalysts that arise from such alloys that are used in the representation of the contact or his Use disintegrate. Under certain circumstances, while using the contact, the Alloy can be regressed intermediately.

Als Beispiele solcher besonders wirksamer Legierungen seien genannt die Legierungen von Alkali- :oder Erdalkalimetallen mit den katalytisch wirksamen Elementen Nickel, Kupfer usw. Trägt man z. B. gepulvertes Nickelmagnesium auf feuchten Bimsstein auf, so zerfällt die Legierung durch den Feuchtig. keitsgehalt des Kontaktträgers unter Bildung von Magnesiumoxyd oder -hydroxyd und einem außerordentlich fein verteilten, hochaktiven Nickel. Analog erhält man aus Kupfermagnesium einen sehr wirksamen Kupferkatalysator.Examples of such particularly effective alloys may be mentioned the alloys of alkali: or alkaline earth metals with the catalytically active ones Elements nickel, copper, etc. If you wear z. B. powdered nickel magnesium on damp Pumice stone, the alloy disintegrates due to the moisture. ity content of the contact carrier with the formation of magnesium oxide or hydroxide and an extraordinarily finely divided, highly active nickel. Similarly, a very effective copper catalyst is obtained from copper magnesium.

Auch andere Legierungen, die durch W asser zerfallen, wie Kupfercalcium, Platinnatrium, Kupferaluminiumzink, Chrommagnesium usw. sind verwendbar. Der katalytisch wirksame Anteil wird hierbei durchweg in außerordentlich fein verteilter und entsprechend wirksamer Form erhalten.Other alloys that disintegrate with water, such as copper calcium, Platinum sodium, copper aluminum zinc, chromium magnesium, etc. are usable. The catalytic effective portion is consistently distributed in an extraordinarily fine way and accordingly more effective form.

Auch solche Legierungen lassen sich verwenden, von denen ein Teil 'Wasserstoff in größeren Mengen aufnimmt, der andere nicht, wie z. B. Nichelbleilegierungen in fein verteilter Form. Hier zerfällt während der Verwendung die Legierung bzw. Mischung offenbar durch Voiumänderung eines der Bestandteile. Auch lassen sich Legierungen verwenden, die durch andere Mittel, wie z. B. Hitze, zerfallen, z. B. Amalgame. Die Zahl der die Legierung zusammensetzenden Metalle ist nicht beschränkt. Man kann bei der Darstellung der Kontaktmasse auch Aktivatoren verwenden.Such alloys can also be used, some of which 'Absorbs hydrogen in larger quantities, the other does not, such as. B. Nickel lead alloys in finely divided form. Here, the alloy or Mixing evidently by changing the volume of one of the components. Alloys can also be used use made by other means, such as B. heat, disintegrate, e.g. B. Amalgams. The number of metals composing the alloy is not limited. One can Also use activators when representing the contact mass.

Beispiel i.Example i.

Auf i3oo Volumteile bohnengroße Bimssteinstücke werden ioo Gewichtsteile fein gepulverte Kupfermagnesiumlegierung aufgetragen und durch Aufstäuben einer verdünnten Wasserglaslösung festgeklebt. Die Kontaktmasse wird ,48 Stunden bei 300° im Wasserstoffstrom erhitzt; sie ist alsdann gebrauchsfähig und gestattet schon bei 9o bis i oo° Ketone wie Aceton glatt zu hydrieren, während im allgemeinen Ketone durch gewöhnliche Kupferkontaktmassen nicht oder nur schlecht zu hydrieren sind. Beispiel z,. Auf erbsengroße Bimssteinstücke wird fein gepulvertes Kupfermagnesium aufgetragen und mit einer Lösung kolloidaler Kieselsäure festgeklebt. Der Katalysator wird bei 2oo° im Wasserstoffstrom 24. Stunden lang erhitzt; er gestattet, Borneol bei 2oo° in bekannter Weise durch Dehydrierung in Gasform glatt in Kampfer überzuführen.Pieces of pumice stone the size of beans for every 300 parts by volume become 100 parts by weight finely powdered copper magnesium alloy applied and by dusting a diluted water glass solution. The contact mass is 48 hours at 300 ° heated in a stream of hydrogen; it is then usable and already permits at 9o to 10o ° ketones such as acetone can be hydrogenated smoothly, while in general ketones cannot be hydrogenated or can only be hydrogenated with difficulty by ordinary copper contact masses. Example z ,. Finely powdered copper magnesium is placed on pea-sized pieces of pumice stone applied and with a solution of colloidal silica glued in place. The catalyst is heated at 2oo ° in a stream of hydrogen for 24 hours; he allows Borneol at 2oo ° in a known manner by dehydration in gaseous form into camphor convict.

Beispiel 3. ' Fein gepulvertes Kupfermagnesium wird mit Wasser zersetzt und alsdann auf Asbest aufgetragen. Der bei 200° im Wasserstoffstrom getrocknete Kontakt gestattet, bei 23o° und roo Atmosphären Kohlenoxyd glatt zu Methylalkohol zu reduzieren. Beispiel q..Example 3. Finely powdered copper magnesium is decomposed with water and then applied to asbestos. The one dried at 200 ° in a stream of hydrogen Contact allowed, at 23o ° and roo atmospheres, carbon monoxide to methyl alcohol to reduce. Example q ..

Auf bohnengroße Bimssteinstücke wird eine fein gepulverte Legierung von Nickelmagnesium aufgetragen und mit einer verdünnten, Wasserglaslösung festgeklebt. Der Kontakt cvird 72 Stunden bei 300' im Wasserstoffstrom erhitzt. Er ist sehr wirksam und reduziert Phenol bei Gegenwart von überschüssigem Wasserstoff bei 16o bis i 8o' glatt zu Cyclohexanol.A finely powdered alloy of nickel magnesium is applied to bean-sized pieces of pumice stone and glued in place with a dilute, water-glass solution. The contact is heated in a stream of hydrogen at 300 ° for 72 hours. It is very effective and, in the presence of excess hydrogen, smoothly reduces phenol to cyclohexanol at 16o to 18o '.

Analog verfährt man bei Verwendung anderer Legierungen.The same procedure is used when using other alloys.

Claims (1)

PATENT-ANSPRÜCFI: Verfahren zur katalytischen Hydrierung und D:ehydrierung organischer Verbindungen, darin bestehend, daß man 1,Z'-a.talysatoren verwendet, die aus solchen Legierungen entstehen, die bei der Darstellung des Kontakts oder seiner Verwendung zerfallen.PATENT REQUIREMENTS: Process for catalytic hydrogenation and dehydrogenation organic compounds, consisting in using 1, Z'-a.talysatoren, which arise from such alloys that are used in the representation of the contact or decay of its use.
DEB109165D 1923-04-04 1923-04-04 Process for the catalytic hydrogenation and dehydrogenation of organic compounds Expired DE408811C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB109165D DE408811C (en) 1923-04-04 1923-04-04 Process for the catalytic hydrogenation and dehydrogenation of organic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB109165D DE408811C (en) 1923-04-04 1923-04-04 Process for the catalytic hydrogenation and dehydrogenation of organic compounds

Publications (1)

Publication Number Publication Date
DE408811C true DE408811C (en) 1925-01-24

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Family Applications (1)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2421416A (en) * 1944-08-30 1947-06-03 Hoffmann La Roche Catalytic hydrogenation of sugars
US2475718A (en) * 1946-08-12 1949-07-12 Schering Corp Process for the hydrogenation of naphthalene compounds
DE974067C (en) * 1949-11-06 1960-09-01 Ici Ltd Process for the production of phenols
US2964577A (en) * 1959-02-05 1960-12-13 Socony Mobil Oil Co Inc Activation of metals for hydrocarbon dehydrogenation
FR2471963A1 (en) * 1979-12-17 1981-06-26 Unisearch Ltd PROCESS FOR PRODUCING CATALYST COMPOSITION FOR LOW TEMPERATURE METHANOL SYNTHESIS, CATALYST FOR USE, AND METHOD FOR PRODUCTION OF METHANOL

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2421416A (en) * 1944-08-30 1947-06-03 Hoffmann La Roche Catalytic hydrogenation of sugars
US2475718A (en) * 1946-08-12 1949-07-12 Schering Corp Process for the hydrogenation of naphthalene compounds
DE974067C (en) * 1949-11-06 1960-09-01 Ici Ltd Process for the production of phenols
US2964577A (en) * 1959-02-05 1960-12-13 Socony Mobil Oil Co Inc Activation of metals for hydrocarbon dehydrogenation
FR2471963A1 (en) * 1979-12-17 1981-06-26 Unisearch Ltd PROCESS FOR PRODUCING CATALYST COMPOSITION FOR LOW TEMPERATURE METHANOL SYNTHESIS, CATALYST FOR USE, AND METHOD FOR PRODUCTION OF METHANOL

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