GB781405A - Hydrogenation of unsaturated carbonyl compounds - Google Patents

Hydrogenation of unsaturated carbonyl compounds

Info

Publication number
GB781405A
GB781405A GB27880/55A GB2788055A GB781405A GB 781405 A GB781405 A GB 781405A GB 27880/55 A GB27880/55 A GB 27880/55A GB 2788055 A GB2788055 A GB 2788055A GB 781405 A GB781405 A GB 781405A
Authority
GB
United Kingdom
Prior art keywords
copper
oxide
catalyst
hydrogenated
carbonyl compounds
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
GB27880/55A
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.)
Celanese Corp
Original Assignee
Celanese Corp
Celanese Corp of America
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 Celanese Corp, Celanese Corp of America filed Critical Celanese Corp
Publication of GB781405A publication Critical patent/GB781405A/en
Expired legal-status Critical Current

Links

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
    • C07C45/61—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
    • 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
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
    • 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
    • C07C29/175—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 with simultaneous reduction of an oxo group
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00—Fermentation processes for beer
    • C12C11/02—Pitching yeast
    • 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
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/00106—Controlling the temperature by indirect heat exchange
    • B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
    • B01J2208/00176—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles outside the reactor
    • 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
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/00106—Controlling the temperature by indirect heat exchange
    • B01J2208/00265—Part of all of the reactants being heated or cooled outside the reactor while recycling
    • B01J2208/00274—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant vapours
    • 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
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/0053—Controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
    • 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
    • Y02P20/582—Recycling of unreacted starting or intermediate materials
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Mycology (AREA)
  • Food Science & Technology (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

Catalysts for use in the hydrogenation of unsaturated carbonyl compounds comprise copper with or without an oxide of an element such as chromium, barium or zinc which acts as a promoter and stabilizer. Such catalysts may be prepared by the reduction of pellets of copper oxide or hydroxide mixed with one or more of the other oxides or the corresponding hydroxides. Alternatively the catalyst may be prepared by reducing with hydrogen a coating, comprising a mixture of the oxide or hydroxide of copper and of one of the metals specified above, previously deposited on an inactive carrier, such as inert alumina or kieselguhr. Other copper catalysts may be used, e.g. the product obtained by reducing with hydrogen mixtures of copper oxide and sodium silicate containing, for example, 10-20 per cent of sodium silicate. In an example unsaturated carbonyl compounds are hydrogenated using as catalyst porous inert alumina tablets coated with a mixture of freshly reduced copper and chromium oxide.ALSO:Ethylenically unsaturated carbonyl compounds are hydrogenated to saturated carbonyl compounds or alcohols or both by a process comprising continuously passing a feed of hydrogen and the unsaturated compound into contact with a hydrogenation catalyst, recycling part of the reacted mixture which has left the catalyst by mixing it with the feed and withdrawing the remainder of the mixture from the system. Suitable unsaturated carbonyl compounds are, for example, aliphatic aldehydes such as crotonaldehyde, acrolein, methacrolein and 2-ethylhex-2-enal; aromatic aldehydes such as cinnamaldehyde; and ketones such as mesityl oxide, methyl vinyl ketone and methyl isopropenyl ketone. Preferably a copper base catalyst is used, e.g. a copper catalyst which contains an oxide of an element such as chromium, barium or zinc, which acts as a promoter and stabilizer. In the examples: (a) crotonaldehyde is hydrogenated in the presence of a catalyst consisting of alumina coated with freshly-reduced copper and chromic oxide, some of the product being recycled, to give a mixture of butyraldehyde and butanol; (b) mesityl oxide is similarly hydrogenated to methyl isobutyl ketone; (c) crotonaldehyde is hydrogenated in the presence of a copper catalyst to give butyraldehyde and butanol, all of the butyraldehyde being recycled to the feed; and (d) crotonaldehyde is similarly hydrogenated to give butyraldehyde and butanol, all of the butanol being recycled to the feed.
GB27880/55A 1954-10-01 1955-09-30 Hydrogenation of unsaturated carbonyl compounds Expired GB781405A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US781405XA 1954-10-01 1954-10-01

Publications (1)

Publication Number Publication Date
GB781405A true GB781405A (en) 1957-08-21

Family

ID=22142161

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27880/55A Expired GB781405A (en) 1954-10-01 1955-09-30 Hydrogenation of unsaturated carbonyl compounds

Country Status (1)

Country Link
GB (1) GB781405A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2982789A (en) * 1957-12-13 1961-05-02 Allied Chem Manufacture of trifluoroethanol
DE1152398B (en) * 1958-08-06 1963-08-08 Engelhard Ind Inc Process for the selective catalytic hydrogenation of the olefin bond of ª ‡, ª ‰ -unsaturated ketones with hydrogen in the presence of a noble metal catalyst
DE1196632B (en) * 1963-04-27 1965-07-15 Scholven Chemie Ag Process for the production of saturated ketones
FR2489304A1 (en) * 1980-09-03 1982-03-05 Alexeeva Klavdia 2-Ethyl:hexanol prodn. from 2-ethyl-hexenal - by hydrogenation over zinc, copper and chromium contg. catalyst (CS 31.3.81)
EP0073129A1 (en) * 1981-08-20 1983-03-02 DAVY McKEE (LONDON) LIMITED Hydrogenation process
US4451677A (en) * 1981-08-20 1984-05-29 Davy Mckee (London) Limited Multistage aldehyde hydrogenation
US4762817A (en) * 1986-11-03 1988-08-09 Union Carbide Corporation Aldehyde hydrogenation catalyst
US4876402A (en) * 1986-11-03 1989-10-24 Union Carbide Chemicals And Plastics Company Inc. Improved aldehyde hydrogenation process
EP0753496A2 (en) * 1995-07-08 1997-01-15 Hüls Aktiengesellschaft Process for the catalytic selective hydrogenation of multiple unsaturated organic substances
US5728891A (en) * 1990-07-08 1998-03-17 Huels Aktiengesellschaft Process for the preparation of 3,3,5-trimethylcyclohexanone
US5756856A (en) * 1995-07-08 1998-05-26 Huels Aktiengesellschaft Process for the preparation of 2-ethylhexanal

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2982789A (en) * 1957-12-13 1961-05-02 Allied Chem Manufacture of trifluoroethanol
DE1152398B (en) * 1958-08-06 1963-08-08 Engelhard Ind Inc Process for the selective catalytic hydrogenation of the olefin bond of ª ‡, ª ‰ -unsaturated ketones with hydrogen in the presence of a noble metal catalyst
DE1196632B (en) * 1963-04-27 1965-07-15 Scholven Chemie Ag Process for the production of saturated ketones
FR2489304A1 (en) * 1980-09-03 1982-03-05 Alexeeva Klavdia 2-Ethyl:hexanol prodn. from 2-ethyl-hexenal - by hydrogenation over zinc, copper and chromium contg. catalyst (CS 31.3.81)
EP0073129A1 (en) * 1981-08-20 1983-03-02 DAVY McKEE (LONDON) LIMITED Hydrogenation process
US4451677A (en) * 1981-08-20 1984-05-29 Davy Mckee (London) Limited Multistage aldehyde hydrogenation
US4762817A (en) * 1986-11-03 1988-08-09 Union Carbide Corporation Aldehyde hydrogenation catalyst
US4876402A (en) * 1986-11-03 1989-10-24 Union Carbide Chemicals And Plastics Company Inc. Improved aldehyde hydrogenation process
US5728891A (en) * 1990-07-08 1998-03-17 Huels Aktiengesellschaft Process for the preparation of 3,3,5-trimethylcyclohexanone
EP0753496A2 (en) * 1995-07-08 1997-01-15 Hüls Aktiengesellschaft Process for the catalytic selective hydrogenation of multiple unsaturated organic substances
EP0753496A3 (en) * 1995-07-08 1997-04-02 Huels Chemische Werke Ag Process for the catalytic selective hydrogenation of multiple unsaturated organic substances
US5756856A (en) * 1995-07-08 1998-05-26 Huels Aktiengesellschaft Process for the preparation of 2-ethylhexanal
US5831135A (en) * 1995-07-08 1998-11-03 Huels Aktiengesellschaft Process for the catalytic selective hydrogenation of polyunsaturated organic substances

Similar Documents

Publication Publication Date Title
EP2180947B1 (en) Hydrogenation catalyst and method for the production of alcohols by hydrogenating carbonyl compounds
GB781405A (en) Hydrogenation of unsaturated carbonyl compounds
US4212825A (en) Aldol condensation and hydrogenation process using a catalyst of nickel and cobalt together with zinc oxide and another metal of groups VIII, IIb, IIIa, IVa and Va of the periodic table
US4001344A (en) Catalyst for partial hydrogenation
GB1158269A (en) Catalytic Process for the Production of Saturated Alcohols.
US3267157A (en) Hydrogenation of fatty acids and lower alkyl esters thereof and activation of copper catalysts therefor
US4273945A (en) Preparation of saturated aliphatic, cycloaliphatic and araliphatic aldehydes
US6706928B2 (en) Aldol condensation reaction and catalyst therefor
US2050788A (en) Process for the production of higher alcohols from a mixture of ethyl alcohol and methyl alcohol
US2446132A (en) Silver catalysts
US2794053A (en) Catalytic dehydrogenation of secondary alcohols to ketones
GB790824A (en) Improvements in the compound di-(2,2,2-trifluoroethyl) acetal of acetaldehyde, process for producing the compound, and process for producing 2,2,2-trifluoroethyl vinyl ether
DE1568657C3 (en)
GB1269167A (en) Improved process for the preparation of aldehydes and ketones and catalysts used therein
EP0013385B1 (en) Process for the preparation of aliphatic carbonyl compounds
US2092449A (en) Manufacture of condensation products from aliphatic organic compounds
Manassen et al. Organic polymers: Correlation between their structure and catalytic activity in heterogeneous systems: IV. Oxidative dehydrogenation: A comparison between the catalytic activity of an organic polymer and that of some molybdate catalysts
US3991127A (en) Production of saturated aliphatic alcohols
US4471141A (en) Preparation of aldehydes
US3527817A (en) Hydrogenation of halogenated aromatic carbonyl compounds
GB1097819A (en) Catalysts and preparation thereof
US2338805A (en) Production of organic compounds
GB1289571A (en)
US2094297A (en) Manufacture of condensation products from aliphatic organic compounds
GB1591540A (en) Catalyst systems