GB610293A - Improvements in or relating to the manufacture of alkyl benzene peroxides - Google Patents
Improvements in or relating to the manufacture of alkyl benzene peroxidesInfo
- Publication number
- GB610293A GB610293A GB1073846A GB1073846A GB610293A GB 610293 A GB610293 A GB 610293A GB 1073846 A GB1073846 A GB 1073846A GB 1073846 A GB1073846 A GB 1073846A GB 610293 A GB610293 A GB 610293A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrocarbon
- hydroperoxide
- aqueous
- peroxides
- reaction
- 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
- 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
- C07C409/10—Cumene hydroperoxide
-
- 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
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Peroxides of alkylbenzene hydrocarbons in which the substituents are one or more alkyl groups at least one of which has a tertiary carbon atom in the alpha position to the benzene ring are prepared by oxidising a dispersion or an emulsion in an aqueous continuous phase of such an alkyl benzene hydrocarbon, or mixtures thereof by intimate contact thereof with molecular oxygen at an elevated temperature, e.g. pure oxygen may be used, and the reaction may be effected at a temperature near to but below the boiling point of the alkylbenzene hydrocarbon-water azeotrope at the prevailing pressure. By peroxide is meant a peroxide and/or a hydroperoxide. The aqueous continuous phase may contain an emulsifying agent and may be maintained between a pH of 7 and 11, e.g. by the addition of small quantities of an alkali metal hydroxide or carbonate. The alkylbenzene hydrocarbon may be subjected to a preliminary purification process prior to the oxidation, e.g. by washing with an aqueous solution of sodium bisulphite or potassium permanganate. The reaction may be terminated when from about 1/3 to 1/5 of the said hydrocarbon is oxidized and unreacted hydrocarbon may be added to a subsequent reaction. The peroxides may be isolated by breaking the emulsion, separating the oily layer from the aqueous layer, and recovering the peroxides such as by distilling off unreacted hydrocarbon, e.g. in vacuo, or hydroperoxides are recovered in the form of their salts, from which the hydroperoxides may be obtained by the addition of acid, by treating the oily layer with a concentrated aqueous alkaline solution, or the reaction mixture may be treated with an excess of a dilute aqueous solution of an alkali metal hydroxide. The aqueous layer separated and acidified with a weak acid, e.g. carbonic acid. In examples, isopropyl benzene hydroperoxide is prepared from isopropyl benzene; cymene hydroperoxide from a mixture of cymenes; and sec: butyltoluene hydroperoxide from a mixture of secondary butyl toluenes.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE472342D BE472342A (en) | 1946-04-08 | ||
GB1073846A GB610293A (en) | 1946-04-08 | 1946-04-08 | Improvements in or relating to the manufacture of alkyl benzene peroxides |
FR944671D FR944671A (en) | 1946-04-08 | 1947-04-03 | Manufacturing process of alkylbenzene peroxides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1073846A GB610293A (en) | 1946-04-08 | 1946-04-08 | Improvements in or relating to the manufacture of alkyl benzene peroxides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB610293A true GB610293A (en) | 1948-10-13 |
Family
ID=9973378
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1073846A Expired GB610293A (en) | 1946-04-08 | 1946-04-08 | Improvements in or relating to the manufacture of alkyl benzene peroxides |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE472342A (en) |
FR (1) | FR944671A (en) |
GB (1) | GB610293A (en) |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2569480A (en) * | 1946-03-22 | 1951-10-02 | Hercules Powder Co Ltd | Emulsion polymerization of unsaturated organic compounds |
US2577768A (en) * | 1949-07-19 | 1951-12-11 | Allied Chem & Dye Corp | Oxidation of cumene |
US2610965A (en) * | 1948-12-24 | 1952-09-16 | Hercules Powder Co Ltd | Homogeneous polymerization of vinylidene compounds using a hydroperoxide catalyst and a basic nitrogen compound |
US2612490A (en) * | 1948-12-24 | 1952-09-30 | Hercules Powder Co Ltd | Homogeneous polymerization of vinylidene compounds with an alpha, alpha-dialkylarylmethyl hydroperoxide and a heavy metal compound as catalyst |
US2619509A (en) * | 1949-07-19 | 1952-11-25 | Allied Chem & Dye Corp | Pretreatment of cumene by oxidation |
US2621213A (en) * | 1949-07-19 | 1952-12-09 | Allied Chem & Dye Corp | Pretreatment of aralkyl hydrocarbons with alkali metal hydroxide |
US2626277A (en) * | 1948-10-15 | 1953-01-20 | Cities Service Res & Dev Co | Oxidation of petroleum fractions |
US2632026A (en) * | 1950-02-18 | 1953-03-17 | Hercules Powder Co Ltd | Oxidation of aromatic hydrocarbons |
US2632774A (en) * | 1949-11-18 | 1953-03-24 | Hercules Powder Co Ltd | Oxioation of aromatic hydrocarbons |
US2633476A (en) * | 1952-03-04 | 1953-03-31 | Shell Dev | Production of aromatic hydroperoxides |
US2655545A (en) * | 1950-03-03 | 1953-10-13 | Farbenfabriken Bayerk | Manufacture of alpha, alpha-dimethylbenzylhydroperoxide |
US2663740A (en) * | 1952-03-05 | 1953-12-22 | Hercules Powder Co Ltd | Oxidation of aromatic hydrocarbons |
US2680138A (en) * | 1949-11-25 | 1954-06-01 | Phillips Petroleum Co | Process for preparing tertiarybutylisopropylbenzene hydroperoxide |
DE923723C (en) * | 1950-10-09 | 1955-02-21 | Rhone Poulenc Sa | Process for the simultaneous production of phenol and acetaldehyde |
US2719864A (en) * | 1950-03-17 | 1955-10-04 | Hercules Powder Co Ltd | Halogenated aromatic hydroperoxides |
DE945506C (en) * | 1951-04-28 | 1956-07-12 | Rhone Poulenc Sa | Process for the production of hydroperoxides by catalytic oxidation of alkyl aromatic hydrocarbons |
US2772259A (en) * | 1953-08-13 | 1956-11-27 | Eastman Kodak Co | Alkali hydroperoxides as olefin polymerization catalysts |
US2776322A (en) * | 1948-10-30 | 1957-01-01 | Hercules Powder Co Ltd | Manufacture of beta-naphthol |
DE1012913B (en) * | 1952-04-11 | 1957-08-01 | Rhone Poulenc Sa | Process for the production of hydroperoxides substituted aromatic hydrocarbons |
DE969266C (en) * | 1951-04-28 | 1958-05-14 | Rhone Poulenc Sa | Process for the production of cumene hydroperoxide by the catalytic oxidation of cumene |
DE1040551B (en) * | 1954-06-18 | 1958-10-09 | Ici Ltd | Process for the preparation of tertiary aryl hydroperoxides |
EP0796833A2 (en) * | 1996-03-20 | 1997-09-24 | Rütgers Kureha Solvents GmbH | Process for the preparation of hydroxyaromatics |
-
0
- BE BE472342D patent/BE472342A/xx unknown
-
1946
- 1946-04-08 GB GB1073846A patent/GB610293A/en not_active Expired
-
1947
- 1947-04-03 FR FR944671D patent/FR944671A/en not_active Expired
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2569480A (en) * | 1946-03-22 | 1951-10-02 | Hercules Powder Co Ltd | Emulsion polymerization of unsaturated organic compounds |
US2626277A (en) * | 1948-10-15 | 1953-01-20 | Cities Service Res & Dev Co | Oxidation of petroleum fractions |
US2776322A (en) * | 1948-10-30 | 1957-01-01 | Hercules Powder Co Ltd | Manufacture of beta-naphthol |
US2610965A (en) * | 1948-12-24 | 1952-09-16 | Hercules Powder Co Ltd | Homogeneous polymerization of vinylidene compounds using a hydroperoxide catalyst and a basic nitrogen compound |
US2612490A (en) * | 1948-12-24 | 1952-09-30 | Hercules Powder Co Ltd | Homogeneous polymerization of vinylidene compounds with an alpha, alpha-dialkylarylmethyl hydroperoxide and a heavy metal compound as catalyst |
US2577768A (en) * | 1949-07-19 | 1951-12-11 | Allied Chem & Dye Corp | Oxidation of cumene |
US2619509A (en) * | 1949-07-19 | 1952-11-25 | Allied Chem & Dye Corp | Pretreatment of cumene by oxidation |
US2621213A (en) * | 1949-07-19 | 1952-12-09 | Allied Chem & Dye Corp | Pretreatment of aralkyl hydrocarbons with alkali metal hydroxide |
US2632774A (en) * | 1949-11-18 | 1953-03-24 | Hercules Powder Co Ltd | Oxioation of aromatic hydrocarbons |
US2680138A (en) * | 1949-11-25 | 1954-06-01 | Phillips Petroleum Co | Process for preparing tertiarybutylisopropylbenzene hydroperoxide |
US2632026A (en) * | 1950-02-18 | 1953-03-17 | Hercules Powder Co Ltd | Oxidation of aromatic hydrocarbons |
US2655545A (en) * | 1950-03-03 | 1953-10-13 | Farbenfabriken Bayerk | Manufacture of alpha, alpha-dimethylbenzylhydroperoxide |
US2719864A (en) * | 1950-03-17 | 1955-10-04 | Hercules Powder Co Ltd | Halogenated aromatic hydroperoxides |
DE923723C (en) * | 1950-10-09 | 1955-02-21 | Rhone Poulenc Sa | Process for the simultaneous production of phenol and acetaldehyde |
DE969266C (en) * | 1951-04-28 | 1958-05-14 | Rhone Poulenc Sa | Process for the production of cumene hydroperoxide by the catalytic oxidation of cumene |
DE945506C (en) * | 1951-04-28 | 1956-07-12 | Rhone Poulenc Sa | Process for the production of hydroperoxides by catalytic oxidation of alkyl aromatic hydrocarbons |
US2633476A (en) * | 1952-03-04 | 1953-03-31 | Shell Dev | Production of aromatic hydroperoxides |
US2663740A (en) * | 1952-03-05 | 1953-12-22 | Hercules Powder Co Ltd | Oxidation of aromatic hydrocarbons |
DE1012913B (en) * | 1952-04-11 | 1957-08-01 | Rhone Poulenc Sa | Process for the production of hydroperoxides substituted aromatic hydrocarbons |
US2772259A (en) * | 1953-08-13 | 1956-11-27 | Eastman Kodak Co | Alkali hydroperoxides as olefin polymerization catalysts |
DE1040551B (en) * | 1954-06-18 | 1958-10-09 | Ici Ltd | Process for the preparation of tertiary aryl hydroperoxides |
EP0796833A2 (en) * | 1996-03-20 | 1997-09-24 | Rütgers Kureha Solvents GmbH | Process for the preparation of hydroxyaromatics |
EP0796833A3 (en) * | 1996-03-20 | 1998-04-01 | Rütgers Kureha Solvents GmbH | Process for the preparation of hydroxyaromatics |
US6107527A (en) * | 1996-03-20 | 2000-08-22 | Rutgers Kureha Solvents Gmbh | Process for the production of hydroxy-aromatic substances |
Also Published As
Publication number | Publication date |
---|---|
BE472342A (en) | |
FR944671A (en) | 1949-04-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB610293A (en) | Improvements in or relating to the manufacture of alkyl benzene peroxides | |
US2548435A (en) | Oxidation of aromatic hydrocarbons | |
GB641250A (en) | Process for the manufacture of di-isopropyl-benzene hydro-peroxides and products resulting therefrom | |
US2547938A (en) | Manufacture of alkyl benzene peroxides | |
GB727498A (en) | The manufacture of organic hydroperoxides | |
GB792558A (en) | Manufacture of organic peroxides | |
US2829158A (en) | Hydroperoxides of alkaryl sulfonic acids and salts thereof | |
GB654035A (en) | Manufacture of beta-isopropylnaphthalene hydroperoxide and beta-naphthol | |
US2881220A (en) | Production of dimethyl phenyl carbinol | |
IT1011141B (en) | PROCEDURE FOR THE OXIDATION OF HYDROCARBONS | |
GB700546A (en) | Hydroperoxides | |
US2621213A (en) | Pretreatment of aralkyl hydrocarbons with alkali metal hydroxide | |
GB711392A (en) | Improvements in or relating to the production of the hydroperoxides of cumene and other alkyl-aromatic hydrocarbons | |
US3833664A (en) | Method for producing organic peroxides | |
GB646102A (en) | Manufacture of organic oxidation products | |
US2973310A (en) | Process for the oxidation of organic compounds | |
GB681990A (en) | Oxidation of aromatic hydrocarbons | |
GB676772A (en) | Improvements in or relating to oxidation of aromatic hydrocarbons | |
US2680139A (en) | Process for the preparation of hydroperoxides | |
US2827493A (en) | Manufacture of cumene hydroperoxide | |
GB770006A (en) | Process for the production of a hydroperoxide | |
US4230890A (en) | Method of recovering dialkylbenzene dihydroperoxide | |
GB730896A (en) | Improvements in and relating to organic hydroperoxides | |
GB786341A (en) | Manufacture of catechol | |
GB655118A (en) | Improvements in or relating to the production of aliphatic di-ketones |