GB741865A - Improvements in and relating to the production of aromatic ketones - Google Patents

Improvements in and relating to the production of aromatic ketones

Info

Publication number
GB741865A
GB741865A GB1970152A GB1970152A GB741865A GB 741865 A GB741865 A GB 741865A GB 1970152 A GB1970152 A GB 1970152A GB 1970152 A GB1970152 A GB 1970152A GB 741865 A GB741865 A GB 741865A
Authority
GB
United Kingdom
Prior art keywords
catalyst
ketone
zinc
chromite
aromatic
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
GB1970152A
Inventor
Peter Smith
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1970152A priority Critical patent/GB741865A/en
Publication of GB741865A publication Critical patent/GB741865A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/48Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/002Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation

Landscapes

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

Abstract

Aromatic ketones are produced by reacting an aromatic carboxylic acid, in which a carboxyl group is attached directly to an aryl group, with an aldehyde or ketone at elevated temperature in the presence of a decarboxylation catalyst which comprises either (a) chromic oxide, e.g. cadmium chromite, zinc chromite, zinc iron chromite and zinc cadmium chromite; or (b) cadmium oxide, e.g. supported on zinc oxide; or (c) copper, e.g. reduced copper-zinc oxide mixture; or (d) a hydrogenating metal of Group VIII of the Periodic System, e.g. nickel, alone or supported on kieselguhr. Preferably the process is effected in vapour phase at temperatures in the range 260 DEG to 500 DEG C. and using excess of carbonyl compound. A solvent such as toluene may be employed. A phenyl carbinol is presumed to be formed as an intermediate which is dehydrogenated to a ketone. Suitable aromatic acids include unsubstituted and alkyl, halogen or nitro-substituted benzoic acids and substituted or unsubstituted naphthoic acids. Suitable carbonyl reactants include formaldehyde, acetaldehyde, propionaldehyde, benzaldehyde and acetone. The aldehyde or ketone may also be produced in situ from an alcohol when the catalyst is capable of catalysing dehydrogenation reactions; e.g. ethyl alcohol may replace acetaldehyde when using a reduced copper-zinc oxide catalyst. By-products include the hydrocarbon formed by decarboxylating the aromatic acid, and carbinols or ketones formed from the aromatic acid and dimers or polymers of the carbonyl compound, e.g. propenyl phenyl carbinol or ketone. In examples (1) a solution of acetaldehyde and benzoic acid in toluene is passed over a reduced copper-zinc oxide catalyst contained in a cylindrical converter at 400 DEG C., through which nitrogen is also passed, to yield acetophenone, with benzene and phenyl propenyl ketone by-products; the process is repeated using (2) acetone and (3) benzaldehyde, the latter giving benzophenone as product; (4) a solution of benzoic acid in ethanol is passed over cadmium oxide to yield acetophenone; (5) zinc iron chromite catalyst is used in the process of example 1. The Provisional Specification refers also to the production of styrene by dehydration of the phenyl methyl carbinol intermediate formed from benzoic acid and acetaldehyde when the catalyst also catalyses dehydration reactions.
GB1970152A 1952-08-05 1952-08-05 Improvements in and relating to the production of aromatic ketones Expired GB741865A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1970152A GB741865A (en) 1952-08-05 1952-08-05 Improvements in and relating to the production of aromatic ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1970152A GB741865A (en) 1952-08-05 1952-08-05 Improvements in and relating to the production of aromatic ketones

Publications (1)

Publication Number Publication Date
GB741865A true GB741865A (en) 1955-12-14

Family

ID=10133756

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1970152A Expired GB741865A (en) 1952-08-05 1952-08-05 Improvements in and relating to the production of aromatic ketones

Country Status (1)

Country Link
GB (1) GB741865A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2375182A1 (en) * 1976-08-20 1978-07-21 Diamond Shamrock Corp PROCESS FOR PREPARING KETONES FROM CARBOXYLIC ACIDS

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2375182A1 (en) * 1976-08-20 1978-07-21 Diamond Shamrock Corp PROCESS FOR PREPARING KETONES FROM CARBOXYLIC ACIDS

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