GB735229A - Improvements in the production of phenols and carbonyl compounds - Google Patents

Improvements in the production of phenols and carbonyl compounds

Info

Publication number
GB735229A
GB735229A GB11039/52A GB1103952A GB735229A GB 735229 A GB735229 A GB 735229A GB 11039/52 A GB11039/52 A GB 11039/52A GB 1103952 A GB1103952 A GB 1103952A GB 735229 A GB735229 A GB 735229A
Authority
GB
United Kingdom
Prior art keywords
phenol
cumene
hydroperoxide
perchloric acid
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
GB11039/52A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB735229A publication Critical patent/GB735229A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/04—Phenol
    • 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
    • C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. 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
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/08—Acetone

Landscapes

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

Abstract

In a process for the production of phenols and carbonyl compounds a hydroperoxide of an alkyl aromatic hydrocarbon of which at least one alkyl group contains a secondary or tertiary carbon atom and perchloric acid are brought into contact at elevated temperature in the presence of a quantity of the phenol to be formed in the reaction, the phenol being introduced before the reaction has commenced. The hydroperoxide may be previously admixed with the phenol before being reacted with the perchloric acid or preferably the perchloric acid and hydroperoxide are added simultaneously to a hot mass of the liquid phenol (which may contain up to an equimolar amount of the carbonyl compound produced in the reaction). The perchloric acid used may be e.g. 0.05 per cent up to about 1 per cent by weight of hydroperoxide and the reaction medium is homogeneous. Suitable hydroperoxides are those of cumene and its homologues, e.g. p-cymene, which yields p-cresol and acetone, isobutylbenzene which gives phenol and methyl ethyl ketone, and ethylbenzene which gives phenol and acetaldehyde. A crude hydroperoxide, e.g. cumene hydroperoxide containing 5 per cent each of cumene and water or 10 per cent cumene, may be used. Reaction temperatures below 65 DEG C. are preferred. The process may be effected continuously by adding hydroperoxide and perchloric acid to the heated phenol and simultaneously removing reaction products. In examples: (1) phenol and acetone are produced continuously by passing perchloric acid and cumene peroxide into phenol and acetone at 40 DEG to 50 DEG C.; (2) cumene hydroperoxide containing water, cumene, phenyl dimethyl carbinol and acetophenone is used in a process as in (1); (3) the decomposition of cumene is effected under partial vacuum, the acetone produced being distilled off continuously. Specification 721,700 is referred to.
GB11039/52A 1951-07-09 1952-05-01 Improvements in the production of phenols and carbonyl compounds Expired GB735229A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR735229X 1951-07-09

Publications (1)

Publication Number Publication Date
GB735229A true GB735229A (en) 1955-08-17

Family

ID=9130378

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11039/52A Expired GB735229A (en) 1951-07-09 1952-05-01 Improvements in the production of phenols and carbonyl compounds

Country Status (1)

Country Link
GB (1) GB735229A (en)

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