GB676772A - Improvements in or relating to oxidation of aromatic hydrocarbons - Google Patents

Improvements in or relating to oxidation of aromatic hydrocarbons

Info

Publication number
GB676772A
GB676772A GB32604/48A GB3260448A GB676772A GB 676772 A GB676772 A GB 676772A GB 32604/48 A GB32604/48 A GB 32604/48A GB 3260448 A GB3260448 A GB 3260448A GB 676772 A GB676772 A GB 676772A
Authority
GB
United Kingdom
Prior art keywords
butyl
oxidation
peroxide
compounds
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
GB32604/48A
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
Application filed by Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Publication of GB676772A publication Critical patent/GB676772A/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
    • C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring
    • 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

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)

Abstract

Compounds of the formula Ar-CHR1R2 (Ar = aryl or alkaryl; R1 and R2 = alkyl) are oxidized to the corresponding hydroperoxides by adding a peroxidic free-radical liberating initiator and contacting the mixture in the liquid phase under anhydrous conditions with a molecular oxygen containing gas. Air or oxygen may be used, at a temperature of 50-100 DEG C. and atmospheric or higher pressure. The initiator is preferably the same peroxide as is formed by the oxidation, but any other organic peroxide is suitable, a list being given of such; the peroxide may be formed in situ, e.g. from hexaphenylethane. There may also be present an alkaline stabilizer which may be an alkali or alkaline earth hydroxide, alkoxide or salt of a weak organic or inorganic acid; a list of such compounds is given. The products may be recovered by washing with dilute alkali and vacuum distillation, or by precipitation with concentrated sodium hydroxide as the crystalline sodium salt. Examples show the oxidation of cumene, p-cymene and di-isopropyl-benzene, the latter giving a mono-hydroperoxide. Alcohols and ketones are by-products, e.g. dimethylbenzyl alcohol and acetophenone from cumene. Other specified starting materials are sec. - butylbenzene, p - ethyl - isopropylbenzene, isopropylnaphthalene and similar compounds derived from anthracene and phenanthrene, in the latter case being dissolved in benzene or other solvent. The groups R1 and R2 may be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl or tert.-butyl and may be the same or different. The process of Specification 646,102 is disclaimed. Specifications 626,095, 629,637, 630,286 and 676,770 also are referred to.
GB32604/48A 1948-06-05 1948-12-16 Improvements in or relating to oxidation of aromatic hydrocarbons Expired GB676772A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US676772XA 1948-06-05 1948-06-05

Publications (1)

Publication Number Publication Date
GB676772A true GB676772A (en) 1952-08-06

Family

ID=22077628

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32604/48A Expired GB676772A (en) 1948-06-05 1948-12-16 Improvements in or relating to oxidation of aromatic hydrocarbons

Country Status (1)

Country Link
GB (1) GB676772A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2796439A (en) * 1953-10-12 1957-06-18 Ici Ltd Oxidation of aromatic hydrocarbons
DE1041960B (en) * 1954-02-17 1958-10-30 Ruhrchemie Ag Process for the production of organic hydroperoxides
US4006191A (en) * 1968-01-13 1977-02-01 Phenolchemie Gmbh Process for the preparation of aralkyl monohydroperoxides
US4153635A (en) * 1976-12-09 1979-05-08 Gulf Research & Development Company Preparation of cumene hydroperoxide
US4217287A (en) 1971-10-06 1980-08-12 Gulf Research & Development Company Epoxidation of alpha-olefins

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2796439A (en) * 1953-10-12 1957-06-18 Ici Ltd Oxidation of aromatic hydrocarbons
DE1041960B (en) * 1954-02-17 1958-10-30 Ruhrchemie Ag Process for the production of organic hydroperoxides
US4006191A (en) * 1968-01-13 1977-02-01 Phenolchemie Gmbh Process for the preparation of aralkyl monohydroperoxides
US4217287A (en) 1971-10-06 1980-08-12 Gulf Research & Development Company Epoxidation of alpha-olefins
US4153635A (en) * 1976-12-09 1979-05-08 Gulf Research & Development Company Preparation of cumene hydroperoxide

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