GB1591540A - Catalyst systems - Google Patents

Catalyst systems Download PDF

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Publication number
GB1591540A
GB1591540A GB23366/79A GB2336679A GB1591540A GB 1591540 A GB1591540 A GB 1591540A GB 23366/79 A GB23366/79 A GB 23366/79A GB 2336679 A GB2336679 A GB 2336679A GB 1591540 A GB1591540 A GB 1591540A
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Prior art keywords
material according
catalyst material
catalyst
cerium compound
ceria
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GB23366/79A
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Diamond Shamrock Corp
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Diamond Shamrock Corp
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Publication date
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Publication of GB1591540A publication Critical patent/GB1591540A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
    • 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
    • C07C45/673—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 change of size of the carbon skeleton
    • 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
    • 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
    • C07C45/70—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 with functional groups containing oxygen only in singly bound form
    • C07C45/71—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 with functional groups containing oxygen only in singly bound form being hydroxy groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • 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

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

Description

PATENT SPECIFICATION ( 11) 1 591 540
O ( 21) Application No 23366/79 ( 22) Filed 19 Aug 1977 ( 19), itg ( 62) Divided Out of No 1591538 ( 31) Convention Application No 716142 ( 32) Filed 20 Aug 1976 in E ó> ( 33) United States of America (US) U ( 44) Complete Specification Published 24 Jun 1981 ( 51) INT CL B 01 J 23/10 CO 7 C 45/00 ( 52) Index at Acceptance Bl E 1134 1135 1197 1207 1260 1363 1634 1701 1738 CB ( 72) Inventors: RICHARD LEE CRYBERG RUSSELL MORROW BIMBER ( 54) IMPROVEMENTS IN OR RELATING TO CATALYST SYSTEMS ( 71) We, DIAMOND SHAMROCK CORPORATION, of 1100 Superior Avenue, Cleveland, Ohio 44114, United States of America, a Corporation organised and existing under the laws of the State of Delaware, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: 5
The present invention relates generally to the production of ketones or aldehydes from other ketones, optionally in the presence of other organic compounds, and is concerned in particular with catalyst systems which are particularly useful for such production methods.
Our co-pending Application No 34938/77 (Specification No 1591538), from which the present application has been divided, discloses and claims methods for the production of 10 ketones, which comprise subjecting a starting compound consisting of another ketone, optionally in admixture with at least one other compound containing a -CO group and/or an -OH group and selected from carboxylic acids, carboxylic acid esters, additional ketones, aldehydes and alcohols, to a disproportionation reaction, by passing such starting compound or mixture over or through a catalytically-active material at a temperature in the 15 range from 3000 to 550 'C and recovering the desired ketone from the resultant reaction products, the reaction being carried out in the absence of a diluent gas and the catalytically-active material being selected from iron filings, alumina, manganese oxides, thorium compounds and cerium compounds.
The method of the aforesaid co-pending application is particularly suitable for the 20 manufacture of pinacolone by the reaction of acetone with pivalic acid Many other reactions are described and our co-pending Application No 7923365 (Serial No 1591539) of even date herewith, which also has been divided from the aforesaid Application No.
34938/77, (Serial No 1591538) discloses an analogous method for the production of aldehydes from mixtures of formic acid and symmetrical ketones 25 The present invention is concerned particularly with a preferred catalyst system for use in the method of production of ketones according to the aforesaid co-pending application or the production of aldehydes according to the aforementioned co-pending divisional application.
In accordance with the present invention, a catalytically-active material is provided, 30 which comprises a cerium compound on an unhydrated alumina support having a specific surface area of approximately 190 square metres per gram Preferably, the cerium compound has a concentration calculated as ceria in the range from 1 % to 10 % by weight, most preferably in the range from 5 % to 10 % by weight It is also preferable for the cerium compound in the catalyst system to be derived from cerium acetate 35 It has been found that good activity, particularly for the ketone and aldehyde production methods of the aforementioned co-pending cases, can be obtained with a catalyst derived by converting cerium acetate to ceria on an alumina support, particularly if the ceria concentration is within the range of 1 % to 10 % calculated as Ce O 2 to total weight As already indicated, the catalyst concentration in terms of ceria is preferably in the range from 40 1 591 540 % to 10 % by weight The most preferred kind of alumina used as the support for the ceria-alumina catalyst of the present invention is that available from Harshaw Chemical Company under the trade mark HARSHAW Al 1404 T-1/8, having a specific surface area of approximately 190 square metres per gram It has been found that in use no treatment prior to the chemical reaction in question is necessary in order for the catalyst to be 5 effective, though as is usual with such catalyst systems a slight ageing of the catalyst has been found to occur during initial use Thereafter, the catalyst system provides good activity of a steady nature for periods in excess of 1,000 hours of use The ceria-alumina catalysts preferred in carrying out the inventions of the aforesaid copending applications and forming the subject of the present invention have a distinct advantage over thoria 10 catalysts Because ceria is not radioactive, the catalyst of the present invention eliminates the hazard which is presented by the radioactivity of thoria and therefore the inconvenience (which is involved when a thoria catalyst is used) of having to comply with regulations covering the use of radioactive materials.
It is believed that the above-described acetone and pivalic acid reaction to obtain 15 pinacolone proceeds as follows:
2 (CH 3)3 C-COOH + CH 3 COCH 3 ceria-alumina> 4700 C 20 2 CH 3-COC(CH 3)3 + CO 2 + H 20 It will be noticed that 2 moles of pivalic acid combine with 1 mole of acetone to provide 2 moles of pinacolone It is believed that the pivalic acid forms a complex with the 25 ceria-alumina catalyst system by losing its acidic hydrogen atom Thereafter, the carbon to oxygen double bond is attacked by the methylene anion of the acetone to provide a shift of electrons to the oxygen atom and the loss of an oxygen atom with the coupling of the acetone to it by its methyl group This results in a probable intermediate of the formula (CH 3)3-CCOCH 2 COCH 3 It is believed that this intermediate is then hydrolyzed, causing a 30 cleavage which results in the formation of pinacolone and an acetic acid group, which Q)thereafter reacts with a second complexed pivalic acid group to form more pinacolone In this process, carbon dioxide and water are also formed.
Further examples of the reaction of ketones and carboxylic acids or carboxylic acid esters to produce other ketones include: acetone and benzoic acid to obtain acetophenone; 35 acetone and propionic acid to obtain methyl ethyl ketone and diethyl ketone; acetone and dimethyl succinate to obtain 2,5-hexandione; acetone and phenylacetic acid to obtain phenylacetone; diethyl ketone and acetic acid to obtain acetone and methyl ethyl ketone; diethyl ketone and benzoic acid to obtain propiophenone; benzophenone and acetic acid to obtain acetophenone; benzoic acid and methylethyl ketone to obtain acetophenone and 40 propiophenone; and acetone and dimethyl terephthalate to obtain pdiacetylbenzene.
In some cases, alcohols or aldehydes may be substituted for the carboxylic acid or ester to produce ketones by the method of the invention It has been found that benzyl alcohol or benzaldehyde may be substituted for benzoic acid in the reaction with acetone to obtain acetophenone It is believed that reactions using an aldehyde or alcohol as a starting 45 material proceed by an oxidation-reduction disproportionation of the feedstocks It is also possible that the ketonic products are formed through carboxylic acid intermediates.
It has also been found that the ceria-alumina catalyst provides good activity for rearrangements of ketones by themselves, such as methyl ethyl ketone alone to obtain acetone and diethyl ketone and acetone and diethyl ketone to obtain methyl ethyl ketone 50 The ceria-alumina catalyst provides good activity for numerous other chemical reactions besides the ketone reactions described above This catalyst would be useful in reactions like: benzophenone and pivalic acid to obtain t-butyl phenyl ketone; 1,3dichloroacetone and pivalic acid to obtain monochloropinacolone; and cyclopentanone and acetic acid to obtain 2,7-octanedione 55 3 1 591 540 3 The ceria-alumina catalyst also provides good activity for many other reactions For example, the following general reaction can be carried out.
RCH 2 X + CH 3 COCH 3 to yield RCH 2 CH 2 COCH 3 + HX, 5 where R is an activating group such as a hydrogen atom or an alkyl or aryl group and X is a good leaving group such as a halogen.
RCH 3 + R 1 CO 2 H to yield RCH 2 COR 1, 10 where R is an electron-withdrawing group such as 2 or 4-pyridyl and R' is alkyl or aryl.
The reaction of a symmetrical ketone of the formula RCH 2 COCH 2 R where R is a hydrogen atom or an alkyl or aryl group, with formic acid to yield an aldehyde of the formula RCH 2 CHO forms the subject of our co-pending Application No 7923365 Serial No 1591539 15 In order that those more skilled in the art may more readily understand the present invention and certain preferred aspects of it, the following Example is offered.
Example
A ceria catalyst was prepared from 100 grams of cerium acetate hydrate (Ce(O Ac)3 XH 2 O) 20 and 400 ml of water at room temperature with agitation to dissolve nearly all of the material The solution was filtered and rinsed with several portions of water to result in approximately 460 ml of filtrate The solution was then combined with 1050 grams of Harshaw Alumina catalyst Al 1404 T 1/8 and tumbled in a gallon jug The solution was absorbed to leave no freely pourable liquid and thus wetting the alumina The mixture was 25 dried in a porcelain dish at approximately 200 'C for 15 hours and then installed in the apparatus according to Example 1 of our co-pending Application No 34938/77 Serial No.
1591538.
The system was flushed out according to Example 1 and the feed reservoir charged with a 2:1 molar ratio of acetone: pivalic acid Pinacolone product was recovered from the 30 condensate in yields up to 90 % of theoretical as evidenced by gas chromatographic studies.

Claims (4)

WHAT WE CLAIM IS:
1 A catalytically-active material which comprises a cerium compound on an unhydrated alumina support having a specific surface of approximately 190 square metres per gram 3
2 A catalyst material according to claim 1, wherein the cerium compound has a concentration in the range from 1 % to 10 % by weight calculated as ceria.
3 A catalyst material according to claim 2, wherein the cerium compound concentration is in the range from 5 % to 10 % by weight.
4 A catalyst material according to any of claims 1 to 3, wherein the cerium compound is 40 derived from cerium acetate.
A catalyst material according to claim 1, substantially as hereinbefore described.
POLLAK MERCER & TENCH, Chartered Patent Agents, 45 Eastcheap House, Central Approach, Letchworth, Hertfordshire, SG 6 3 DS.
and 50 High Holborn House, 52/54 High Holborn, London WC 1 V 6 RY, Agents for the Applicants.
Printed for Her Majesty's Stationery Office, by Croydon Printing Company Limited, Croydon, Surrey, 1981.
Published by The Patent Office, 25 Southampton Buildings, London, WC 2 A IAY, from which copies may be obtained.
GB23366/79A 1976-08-20 1977-08-19 Catalyst systems Expired GB1591540A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US71614276A 1976-08-20 1976-08-20

Publications (1)

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GB1591540A true GB1591540A (en) 1981-06-24

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ID=24876925

Family Applications (3)

Application Number Title Priority Date Filing Date
GB23365/79A Expired GB1591539A (en) 1976-08-20 1977-08-19 Preparation of aldehydes
GB34938/77A Expired GB1591538A (en) 1976-08-20 1977-08-19 Preparation of ketones
GB23366/79A Expired GB1591540A (en) 1976-08-20 1977-08-19 Catalyst systems

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB23365/79A Expired GB1591539A (en) 1976-08-20 1977-08-19 Preparation of aldehydes
GB34938/77A Expired GB1591538A (en) 1976-08-20 1977-08-19 Preparation of ketones

Country Status (6)

Country Link
JP (1) JPS5325511A (en)
BE (1) BE857956A (en)
CA (1) CA1120457A (en)
DE (1) DE2737511A1 (en)
FR (4) FR2375179A1 (en)
GB (3) GB1591539A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0101111A1 (en) * 1982-08-09 1984-02-22 Shell Internationale Researchmaatschappij B.V. Process and catalytic composition for the preparation of aldehydes, and aldehydes thus prepared

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57209819A (en) * 1981-06-19 1982-12-23 Nissan Motor Co Ltd Preparation of active alumina pellet supporting cerium uniformly
EP0085996B1 (en) * 1982-02-08 1987-03-04 Shell Internationale Researchmaatschappij B.V. Process for the preparation of unsymmetrical aliphatic ketones
FR2592039B1 (en) * 1985-12-23 1988-11-25 Centre Nat Rech Scient PROCESS FOR ACYLATION OF AROMATIC HYDROCARBONS
DE3709765A1 (en) * 1987-03-25 1988-10-06 Huels Chemische Werke Ag METHOD FOR PRODUCING UNSYMMETRIC ALIPHATIC KETONES
GB8808240D0 (en) * 1988-04-08 1988-05-11 Knowsley Contract Chem Ltd Catalyst & its use in oxidation

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2064254A (en) * 1931-08-19 1936-12-15 Fuchs Otto Production of higher ketones
US2596212A (en) * 1946-10-25 1952-05-13 Phillips Petroleum Co Synthesis of pinacolone
GB741865A (en) * 1952-08-05 1955-12-14 Ici Ltd Improvements in and relating to the production of aromatic ketones
FR1216288A (en) * 1957-08-30 1960-04-25 Unilever Nv Beta-diketones and their preparation process
FR1262951A (en) * 1960-07-20 1961-06-05 Exxon Research Engineering Co Catalytic condensation of ketones, to make higher molecular weight ketones
US3361828A (en) * 1962-01-02 1968-01-02 Exxon Research Engineering Co Preparation of higher molecular weight ketones
FR1529019A (en) * 1966-08-05 1968-06-14 Eastman Kodak Co New process for preparing ketones, especially aliphatics
CA1020173A (en) * 1972-11-24 1977-11-01 Hoechst Aktiengesellschaft Process for alkylating ketones
DE2412230A1 (en) * 1974-03-14 1975-09-18 Hoechst Ag CARRIER CATALYST

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0101111A1 (en) * 1982-08-09 1984-02-22 Shell Internationale Researchmaatschappij B.V. Process and catalytic composition for the preparation of aldehydes, and aldehydes thus prepared

Also Published As

Publication number Publication date
FR2375179A1 (en) 1978-07-21
JPS5325511A (en) 1978-03-09
DE2737511C2 (en) 1988-12-29
FR2375182A1 (en) 1978-07-21
FR2375179B1 (en) 1983-09-16
FR2375181A1 (en) 1978-07-21
JPS6256141B2 (en) 1987-11-24
GB1591539A (en) 1981-06-24
GB1591538A (en) 1981-06-24
FR2375181B1 (en) 1981-04-30
CA1120457A (en) 1982-03-23
FR2375180A1 (en) 1978-07-21
FR2375180B1 (en) 1981-04-30
FR2375182B1 (en) 1982-12-03
DE2737511A1 (en) 1978-02-23
BE857956A (en) 1978-02-20

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PS Patent sealed
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19940819