GB910301A - Producing phenols from alkyl-aromatic hydroperoxides - Google Patents

Producing phenols from alkyl-aromatic hydroperoxides

Info

Publication number
GB910301A
GB910301A GB10511/60A GB1051160A GB910301A GB 910301 A GB910301 A GB 910301A GB 10511/60 A GB10511/60 A GB 10511/60A GB 1051160 A GB1051160 A GB 1051160A GB 910301 A GB910301 A GB 910301A
Authority
GB
United Kingdom
Prior art keywords
mixture
passed
temperature
cooling system
hydroperoxide
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
GB10511/60A
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.)
Ineos Phenol GmbH
Original Assignee
Phenolchemie GmbH and Co KG
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 Phenolchemie GmbH and Co KG filed Critical Phenolchemie GmbH and Co KG
Publication of GB910301A publication Critical patent/GB910301A/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
    • 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

Landscapes

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

Abstract

In a method of forming a phenol by the action of an acid on a solution of an alkylaromatic hydroperoxide in a liquid hydrocarbon, the acidified mixture is passed through a cooling system wherein the temperature of the mixture is maintained constant \sB5 DEG C. at a predetermined value within the range of 10 DEG to 80 DEG C. until the cleavage reaction is completed. In an example, a mixture comprising 6 parts of a 40% solution of cumene hydroperoxide in cumene and 24 parts of 42% sulphuric acid is passed through a centrifugal pump. The mixture is then passed at 40 DEG C. through a cooling system comprising ten heatexchangers, the cooling capacity of which are adjusted so that the fluctuations of the temperature of the mixture do not exceed 2 DEG C. Towards the end of the reaction, a slight increase in temperature, within the permitted range of fluctuation, is allowed to take place so that substantially complete cleavage of the hydroperoxide is obtained. The mixture remains in the cooling system for about 45 seconds. After distillation, a yield of 87% of phenol is obtained. The cleavage of the hydroperoxides of di-isopropylbenzene, methylisopropyl benzene and isopropylnaphthalene is mentioned.
GB10511/60A 1959-03-28 1960-03-24 Producing phenols from alkyl-aromatic hydroperoxides Expired GB910301A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP22497A DE1112527B (en) 1959-03-28 1959-03-28 Process for cleaving hydroperoxides of alkyl aromatic hydrocarbons

Publications (1)

Publication Number Publication Date
GB910301A true GB910301A (en) 1962-11-14

Family

ID=7368766

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10511/60A Expired GB910301A (en) 1959-03-28 1960-03-24 Producing phenols from alkyl-aromatic hydroperoxides

Country Status (3)

Country Link
BE (1) BE589082A (en)
DE (1) DE1112527B (en)
GB (1) GB910301A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0018159A1 (en) * 1979-04-20 1980-10-29 Imperial Chemical Industries Plc Process for the production of phenol, acetone and alpha methylstyrene

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1443329B1 (en) * 1962-01-10 1970-01-02 It Resine S P A Soc Process and device for the continuous catalytic cracking of alkylaryl hydroperoxides, especially cumene hydroperoxide, with sulfuric acid
DE1239317B (en) * 1963-01-19 1967-04-27 Scholven Chemie Ag Method and device for the cleavage of dialkylbenzene dihydroperoxides
DE19950952A1 (en) * 1999-10-22 2001-04-26 Phenolchemie Gmbh & Co Kg Preparation of phenol and acetone comprises the homogeneous acid catalyzed cleavage of cumyl hydroperoxide in a microreactor with microchannels
DE10111889A1 (en) * 2001-03-13 2002-10-02 Phenolchemie Gmbh & Co Kg Production of phenol and acetone containing low levels of cresol, comprises heating the acid cleavage product to a specified temperature upto 15 minutes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL77380C (en) * 1947-02-13

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0018159A1 (en) * 1979-04-20 1980-10-29 Imperial Chemical Industries Plc Process for the production of phenol, acetone and alpha methylstyrene

Also Published As

Publication number Publication date
BE589082A (en) 1960-07-18
DE1112527B (en) 1961-08-10

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