GB741865A - Improvements in and relating to the production of aromatic ketones - Google Patents
Improvements in and relating to the production of aromatic ketonesInfo
- 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
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
- C07C45/45—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
- C07C45/002—Preparation 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.
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)
| 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 |
-
1952
- 1952-08-05 GB GB1970152A patent/GB741865A/en not_active Expired
Cited By (1)
| 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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