GB578608A - Controlled oxidation of aralkyl hydrocarbons and of their partially halogenated derivatives - Google Patents

Controlled oxidation of aralkyl hydrocarbons and of their partially halogenated derivatives

Info

Publication number
GB578608A
GB578608A GB20885/43A GB2088543A GB578608A GB 578608 A GB578608 A GB 578608A GB 20885/43 A GB20885/43 A GB 20885/43A GB 2088543 A GB2088543 A GB 2088543A GB 578608 A GB578608 A GB 578608A
Authority
GB
United Kingdom
Prior art keywords
oxygen
hydrogen bromide
hydrogen
benzene
nitrogen
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
GB20885/43A
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.)
Shell Development Co
Original Assignee
Shell Development Co
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 Shell Development Co filed Critical Shell Development Co
Publication of GB578608A publication Critical patent/GB578608A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/58—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of molecular oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/04—Monocyclic monocarboxylic acids
    • C07C63/06—Benzoic acid

Landscapes

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

Abstract

Substituted phenols, aromatic carboxylic acids, aromatic ketones and/or aromatic peroxides are made by reacting one or more alkylated aromatic hydrocarbons or halogenated alkylated aromatic hydrocarbons containing at least one replaceable hydrogen atom, with oxygen in the presence of hydrogen bromide at an elevated temperature below that at which spontaneous combustion or substantial decomposition of the carbon structure occurs. The hydrogen bromide may be produced from a compound capable of yielding hydrogen bromide under the operating conditions. Specified compounds which may be oxidised by the process are toluene, xylenes, ethyl benzene, hemimellithene, mesitylene, n-propyl benzene, cymene, durene, tertiary butyl benzene, diphenylmethane, diphenylethane, and their homologues, and derivatives thereof partially halogenated in the ring or in the alkyl chain, e.g. benzyl chloride and benzyl bromide. The oxidation may be effected in presence of inert diluents such as steam, nitrogen, carbon dioxide or methane, and oxygen containing mixtures, such as air, may be used instead of oxygen. In examples: (1) toluene, oxygen, nitrogen and hydrogen bromide are heated to about 200 DEG C. at atmospheric pressure to give benzoic acid; (2) ethyl benzene, oxygen, nitrogen and hydrogen bromide are heated to about 195 DEG C. at atmospheric pressure to give acetophenone, carboxylic acids (chiefly phenylacetic acid) and a mixture of bromophenols. Rapid neutralisation of the products with sodium carbonate or hydroxide increases the yields. Aralkyl bromides formed by side reaction may be oxidised by the process of the invention and any hydrogen bromide regenerated may be re-used. The Specification as open to inspection under Sect. 91 comprises also the oxidation of non-alkylated aromatic hydrocarbons, e.g. benzene, naphthalene and phenanthrene, and their halogenated derivatives, and the use, as catalysts, of hydrogen halides in general (hydrogen chloride being additionally specified) or of chlorine or bromine. This subject-matter does not appear in the Specification as accepted.
GB20885/43A 1943-01-30 1943-12-13 Controlled oxidation of aralkyl hydrocarbons and of their partially halogenated derivatives Expired GB578608A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US578608XA 1943-01-30 1943-01-30

Publications (1)

Publication Number Publication Date
GB578608A true GB578608A (en) 1946-07-04

Family

ID=22013172

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20885/43A Expired GB578608A (en) 1943-01-30 1943-12-13 Controlled oxidation of aralkyl hydrocarbons and of their partially halogenated derivatives

Country Status (2)

Country Link
GB (1) GB578608A (en)
NL (1) NL62757C (en)

Also Published As

Publication number Publication date
NL62757C (en)

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