GB758934A - Improvements in and relating to the oxidation of aromatic hydrocarbons - Google Patents

Improvements in and relating to the oxidation of aromatic hydrocarbons

Info

Publication number
GB758934A
GB758934A GB27959/53A GB2795953A GB758934A GB 758934 A GB758934 A GB 758934A GB 27959/53 A GB27959/53 A GB 27959/53A GB 2795953 A GB2795953 A GB 2795953A GB 758934 A GB758934 A GB 758934A
Authority
GB
United Kingdom
Prior art keywords
carbonate
organic acid
weak organic
benzenes
cumene
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
GB27959/53A
Inventor
Kurt Helmut Berneis
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 GB27959/53A priority Critical patent/GB758934A/en
Priority to US443955A priority patent/US2796439A/en
Priority to DEI8980A priority patent/DE1030831B/en
Priority to FR1111244D priority patent/FR1111244A/en
Publication of GB758934A publication Critical patent/GB758934A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C407/006—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
    • 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
    • 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
    • C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring

Landscapes

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

Abstract

Tertiary hydroperoxides are made by oxidizing an aromatic hydrocarbon of the formula Ar.R, where Ar is a phenyl group or a substituted derivative thereof and R is either an alkyl group having a tertiary carbon atom adjacent to the nucleus or a cyclohexyl group, in liquid phase in absence of added water with a gas containing free oxygen, in presence of a peroxide oxidation initiator capable of initiating a free radical oxidation chain, and as stabilizing agents both a carbonate and a weak organic acid salt of an alkali metal, an alkaline earth, or magnesium, the total quantity of stabilizing agents being at least 1.5 per cent of the weight of aromatic hydrocarbon employed, and the weight ratio of carbonate to weak organic acid salt being in the range 1 : 2 to 2 : 1. The weak organic acid may be any acid weaker than acetic, e.g. stearic, palmitic, lauric, or the mixture of fatty acids obtained by hydrolysis of fats. The reaction temperature may be 50-100 DEG C. Inert diluents, e.g. chlorbenzenes or tetrachlorethane, may be employed. Examples describe the oxygenation of cumene and diisopropylbenzene in presence of the corresponding hydroperoxides, of sodium carbonate and sodium stearate, and of cumene similarly, using calcium carbonate and stearate in place of the sodium salts. The cymenes, sec-butyl-benzenes, and cyclohexyl-benzenes may be similarly treated.
GB27959/53A 1953-10-12 1953-10-12 Improvements in and relating to the oxidation of aromatic hydrocarbons Expired GB758934A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB27959/53A GB758934A (en) 1953-10-12 1953-10-12 Improvements in and relating to the oxidation of aromatic hydrocarbons
US443955A US2796439A (en) 1953-10-12 1954-07-16 Oxidation of aromatic hydrocarbons
DEI8980A DE1030831B (en) 1953-10-12 1954-08-02 Process for the preparation of tertiary aromatic hydroperoxides
FR1111244D FR1111244A (en) 1953-10-12 1954-09-04 Oxidation of aromatic hydrocarbons

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB27959/53A GB758934A (en) 1953-10-12 1953-10-12 Improvements in and relating to the oxidation of aromatic hydrocarbons

Publications (1)

Publication Number Publication Date
GB758934A true GB758934A (en) 1956-10-10

Family

ID=10268023

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27959/53A Expired GB758934A (en) 1953-10-12 1953-10-12 Improvements in and relating to the oxidation of aromatic hydrocarbons

Country Status (4)

Country Link
US (1) US2796439A (en)
DE (1) DE1030831B (en)
FR (1) FR1111244A (en)
GB (1) GB758934A (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL80287C (en) * 1951-04-28
LU37885A1 (en) * 1958-12-17
DE1156411B (en) * 1960-01-11 1963-10-31 It Resine Soc Process for the production of cumene hydroperoxide
US3846499A (en) * 1970-10-22 1974-11-05 Texaco Inc Manufacture of hydrocarbyl hydroperoxide
US4152358A (en) * 1971-05-24 1979-05-01 Petro-Tex Chemical Corporation Preparation of hydroperoxides by autoxidation
JPS5146095B2 (en) * 1972-09-08 1976-12-07
US4169210A (en) * 1974-08-12 1979-09-25 Cosden Technology, Inc. Oxidation of diethylbenzenes
US4282383A (en) * 1976-05-24 1981-08-04 The Upjohn Company Process for the autoxidation of cyclohexylbenzene to form cyclohexylbenzene hydroperoxide
JPS6017783B2 (en) * 1977-10-31 1985-05-07 三井化学株式会社 Method for oxidizing m-diisopropylbenzene
US4487974A (en) * 1983-02-24 1984-12-11 Texaco Inc. Oxidation of cyclohexylbenzene to 1-phenyl cyclohexylhydroperoxide
EP0320451A3 (en) * 1987-12-09 1991-03-27 Ciba-Geigy Ag Process for preparing alkyl-substituted phenols or naphthols

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2547938A (en) * 1946-04-08 1951-04-10 Hercules Powder Co Ltd Manufacture of alkyl benzene peroxides
GB676772A (en) * 1948-06-05 1952-08-06 Distillers Co Yeast Ltd Improvements in or relating to oxidation of aromatic hydrocarbons
NL82918C (en) * 1948-06-05
DE864938C (en) * 1949-07-27 1953-01-29 Carl Corneliussen Device for the electric killing of sea animals during the catch, consisting of one to a catching electrode, e.g. B. Harpoon, connected power generating unit
US2613227A (en) * 1950-05-23 1952-10-07 Allied Chem & Dye Corp Cumene oxidation
US2681936A (en) * 1950-08-03 1954-06-22 Allied Chem & Dye Corp Sodium carbonate in cumene oxidation
BE508321A (en) * 1951-04-28

Also Published As

Publication number Publication date
US2796439A (en) 1957-06-18
DE1030831B (en) 1958-05-29
FR1111244A (en) 1956-02-23

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