GB770622A - Process for the production of aromatic ketone hydroperoxides - Google Patents
Process for the production of aromatic ketone hydroperoxidesInfo
- Publication number
- GB770622A GB770622A GB660154A GB660154A GB770622A GB 770622 A GB770622 A GB 770622A GB 660154 A GB660154 A GB 660154A GB 660154 A GB660154 A GB 660154A GB 770622 A GB770622 A GB 770622A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroperoxide
- methyl
- ketone
- benzyl
- oxygen
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/14—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom belonging to a ring other than a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Ketone hydroperoxides of formula <FORM:0770622/IV(b)/1> wherein R1 is a hydrogen atom or an alkyl, aralkyl or aryl radical, R2 is an alkyl, aralkyl or aryl radical, or R1 and R2 together form part of a cycloalkyl ring, R3 is an alkyl, aryl or cycloalkyl group, or one of their substituted derivatives, and Ar is an aromatic nucleus which may be further substituted by alkyl, aryl or aralkyl groups, are prepared by contacting a ketone of formula <FORM:0770622/IV(b)/2> in liquid phase at elevated temperatures with gases containing molecular oxygen. The following groups are specified in the above formul : R1 and R2 are methyl, ethyl, propyl, butyl, phenyl, naphthyl, tolyl, or benzyl or together form a part of a cyclopentyl or cyclohexyl ring; R3 is methyl, ethyl, propyl, butyl, phenyl, naphthyl, tolyl, cyclopentyl, cyclohexyl, or benzyl; and Ar is a benzene or naphthalene ring which may be substituted by methyl, ethyl, phenyl, tolyl, or benzyl. The ketone starting material may be used alone or in the presence of an inert diluent such as water or benzene. In the case of water an emulsifying agent such as sodium ricinoleate or lauryl sulphate may be used. The molecular oxygen may be oxygen, or mixtures containing oxygen such as air, and ozone may be present. The rate of input of oxygen is preferably between 0.01 and 1.0 mols. per hour per mol. of starting material. The temperature is preferably between about 80 DEG and 120 DEG C. and the pH of the reaction mixture is between about pH4 and 10. The presence of a free-radical oxidation initiator such as acetyl peroxide, benzyl peroxide, triphenyl methyl peroxide, tert.-butyl peroxide or hydroperoxide, tert.-amyl hydroperoxide, diphenyl methyl hydroperoxide, tetrahydronaphthalene hydroperoxide, methyl cyclohexyl hydroperoxide, cyclohexene hydroperoxide, a : a - dimethyl benzylhydroperoxide, a : a -dimethyl p-methyl or -isopropyl benzyl hydroperoxide, a : a : a 1 : a 1-tetramethyl p - xylylene dihydroperoxide, a : a - dimethyl naphthyl methyl hydroperoxide, hexaphenyl ethane and 2-azo-bisisobutyronitrile in amounts of about 0.1 to 20 per cent by weight of the ketone is advantageous. The preferred initiator is the hydroperoxide formed by oxidation of the same ketone. The hydroperoxides may be separated from the oxidation mixture by fractional distillation at low pressure, by crystallization, by precipitation as its sodium hydroxide solution and neutralizing the alkaline extract with carbon dioxide. The hydroperoxides may be decomposed to give the corresponding phenol. In examples a mixture of m- or p-isopropylacetophenone, calcium hydroxide and 2-azo-bisisobutyronitrile is oxidized by heating to 90 DEG C. and passing oxygen, the oxidation mixture being subsequently extracted with sodium hydroxide solution, the extract saturated with carbon dioxide and extracted with ether, the ether being evaporated to give m- or p-acetyl-a : a -dimethylbenzyl hydroperoxide. The Provisional Specification refers to the use of heavy metal compounds as catalysts in the oxidation process. Specified metals are manganese, cobalt, lead, iron, nickel, copper, vanadium and mercury. Specification 770,623 is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB660154A GB770622A (en) | 1954-03-06 | 1954-03-06 | Process for the production of aromatic ketone hydroperoxides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB660154A GB770622A (en) | 1954-03-06 | 1954-03-06 | Process for the production of aromatic ketone hydroperoxides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB770622A true GB770622A (en) | 1957-03-20 |
Family
ID=9817462
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB660154A Expired GB770622A (en) | 1954-03-06 | 1954-03-06 | Process for the production of aromatic ketone hydroperoxides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB770622A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0149176A2 (en) * | 1983-12-20 | 1985-07-24 | Sumitomo Chemical Company, Limited | Process for producing m-hydroxyacetophenone |
FR2564460A1 (en) * | 1984-05-17 | 1985-11-22 | Kureha Chemical Ind Co Ltd | METHYL 2- (2-HYDROPEROXY-2-PROPYL) NAPHTHALENE-6-CARBOXYLATE AND PROCESS FOR PREPARING THE SAME |
-
1954
- 1954-03-06 GB GB660154A patent/GB770622A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0149176A2 (en) * | 1983-12-20 | 1985-07-24 | Sumitomo Chemical Company, Limited | Process for producing m-hydroxyacetophenone |
EP0149176A3 (en) * | 1983-12-20 | 1986-01-08 | Sumitomo Chemical Company, Limited | Process for producing m-hydroxyacetophenone |
FR2564460A1 (en) * | 1984-05-17 | 1985-11-22 | Kureha Chemical Ind Co Ltd | METHYL 2- (2-HYDROPEROXY-2-PROPYL) NAPHTHALENE-6-CARBOXYLATE AND PROCESS FOR PREPARING THE SAME |
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