GB721700A - Process for the production of phenols and carbonyl compounds - Google Patents

Process for the production of phenols and carbonyl compounds

Info

Publication number
GB721700A
GB721700A GB11038/52A GB1103852A GB721700A GB 721700 A GB721700 A GB 721700A GB 11038/52 A GB11038/52 A GB 11038/52A GB 1103852 A GB1103852 A GB 1103852A GB 721700 A GB721700 A GB 721700A
Authority
GB
United Kingdom
Prior art keywords
phenol
hydroperoxide
per cent
cumene
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
GB11038/52A
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 GB721700A publication Critical patent/GB721700A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • C07C49/10—Methyl-ethyl ketone

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 by the decomposition by means of sulphuric acid of a hydroperoxide of an aromatic hydrocarbon substituted by one or more alkyl groups of which at least one contains a secondary or tertiary carbon atom, the hydroperoxide and the sulphuric acid are brought into contact at elevated temperature in the presence of a quantity of the phenol to be formed in the reaction, said phenol being introduced before the reaction has commenced, the initial reaction mixture being free from the carbonyl compound formed in the fission reaction or containing a proportion of such carbonyl compound less than 10 per cent of the combined weight of said phenol and said carbonyl compound. Hydroperoxides mentioned are those of cumene and its homologues, e.g. of p-cymene, isobutylbenzene, di-isopropylbenzene and ethylbenzene (which yields phenol and acetaldehyde). The hydroperoxide and phenol may be mixed before adding the acid, but preferably the acid and hydroperoxide are added simultaneously to a hot mass of liquid phenol (termed a "foot"). The sulphuric acid may be in such amounts as 1 to 5 per cent by weight in relation to the hydroperoxide and may be used at a concentration of 30 to 75 per cent, which is completely soluble in the "foot". The cumene hydroperoxide may be a crude product resulting from the partial oxidation of cumene from which the greater part of the unconverted hydrocarbon has been removed by distillation and/or steam distillation. Such a product may contain, for example, 5 per cent of cumene and 5 per cent of water, or a higher cumene content for less water. The reaction is preferably carried out at below 65 DEG C. It may be performed continuously, if desired with elimination of the carbonyl compound as it is formed. In examples (1) crude cumene hydroperoxide and 50 per cent sulphuric acid are run into phenol initially heated to 45 DEG C. to give phenol, acetone, and as by-products, methyl-styrolene and acetophenone; (2) a similar process to (1) is effected at reduced pressure with continuous distillation of the acetone produced; (3) p-cymene peroxide and 50 per cent sulphuric acid are run into p-cresol heated at 40 DEG C. Reaction is effected at 45 DEG to 50 DEG C. to give p-cresol and acetone; (4) in a similar process to (3) isobutylbenzene hydroperoxide is decomposed to give phenol and methylethyl ketone.
GB11038/52A 1951-05-17 1952-05-01 Process for the production of phenols and carbonyl compounds Expired GB721700A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR721700X 1951-05-17

Publications (1)

Publication Number Publication Date
GB721700A true GB721700A (en) 1955-01-12

Family

ID=9098415

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11038/52A Expired GB721700A (en) 1951-05-17 1952-05-01 Process for the production of phenols and carbonyl compounds

Country Status (1)

Country Link
GB (1) GB721700A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009129388A1 (en) * 2008-04-16 2009-10-22 Sabic Innovative Plastics Ip B.V Method for producing phenol and acetone
US8030525B2 (en) 2008-10-16 2011-10-04 Sabic Innovative Plastics Ip B.V. Method for producing phenol and acetone

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009129388A1 (en) * 2008-04-16 2009-10-22 Sabic Innovative Plastics Ip B.V Method for producing phenol and acetone
US8003827B2 (en) 2008-04-16 2011-08-23 Sabic Innovative Plastics Ip B.V. Method for producing phenol and acetone
CN102066298B (en) * 2008-04-16 2013-12-11 沙伯基础创新塑料知识产权有限公司 Method for producing phenol and acetone
US8030525B2 (en) 2008-10-16 2011-10-04 Sabic Innovative Plastics Ip B.V. Method for producing phenol and acetone

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