GB610293A - Improvements in or relating to the manufacture of alkyl benzene peroxides - Google Patents

Improvements in or relating to the manufacture of alkyl benzene peroxides

Info

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
Application number
GB1073846A
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co 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
Priority to BE472342D priority Critical patent/BE472342A/xx
Application filed by Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB1073846A priority patent/GB610293A/en
Priority to FR944671D priority patent/FR944671A/en
Publication of GB610293A publication Critical patent/GB610293A/en
Expired legal-status Critical Current

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.
GB1073846A 1946-04-08 1946-04-08 Improvements in or relating to the manufacture of alkyl benzene peroxides Expired GB610293A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (24)

* Cited by examiner, † Cited by third party
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
FR944671A (en) 1949-04-12
BE472342A (en)

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