GB740022A - Improvements relating to the preparation of phenols and cycloalkanones - Google Patents

Improvements relating to the preparation of phenols and cycloalkanones

Info

Publication number
GB740022A
GB740022A GB33232/53A GB3323253A GB740022A GB 740022 A GB740022 A GB 740022A GB 33232/53 A GB33232/53 A GB 33232/53A GB 3323253 A GB3323253 A GB 3323253A GB 740022 A GB740022 A GB 740022A
Authority
GB
United Kingdom
Prior art keywords
phenyl
cyclohexane
cycloalkanones
phenols
solution
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
GB33232/53A
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.)
Stamicarbon BV
Original Assignee
Stamicarbon BV
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 Stamicarbon BV filed Critical Stamicarbon BV
Publication of GB740022A publication Critical patent/GB740022A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered 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
    • C07C37/08—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
    • 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
    • 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
    • C07C409/14—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 belonging to a ring other than a six-membered aromatic ring
    • 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
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

Phenols and cycloalkanones are prepared by oxidizing cycloalkyl derivatives of aromatic hydrocarbons with gases containing free oxygen at a temperature of 125-140 DEG C. to form hydroperoxides and splitting these hydroperoxides in an acid medium. Starting materials in the process are phenyl cyclohexane, phenyl cycloheptane, tolyl cyclohexane, 1-phenyl - 4 - methyl cyclohexane, 1 - (41 - ethyl - phenyl) - 4 - methyl - cyclohexane, dicyclohexyl benzenes and dicyclohexyl naphthalenes. Using the temperature range cited, about 20 per cent of hydroperoxide is formed in 3 hours, substantially free from by-products. The oxidation may be carried out at atmospheric or superatmospheric pressure, and in the presence of finely-divided metal catalysts such as silver, platinum, and copper, supported on kieselguhr. The resultant solution of hydroperoxide in hydrocarbon is concentrated in a film-evaporator to give a 50-60 per cent solution, which is mixed with dilute sulphuric acid (10-25 per cent) and heated by passing steam which also removes the volatile products. The phenols are separated from the reaction products by solution in alkali metal hydroxide solution and then acidified and distilled. The cycloalkanones are also purified by distillation. The process can be operated continuously. In the example phenylcyclohexane is treated by the process of the invention to given phenol and cyclohexanone. Specification 681,613 is referred to.
GB33232/53A 1952-12-02 1953-11-30 Improvements relating to the preparation of phenols and cycloalkanones Expired GB740022A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL740022X 1952-12-02

Publications (1)

Publication Number Publication Date
GB740022A true GB740022A (en) 1955-11-09

Family

ID=19820525

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33232/53A Expired GB740022A (en) 1952-12-02 1953-11-30 Improvements relating to the preparation of phenols and cycloalkanones

Country Status (1)

Country Link
GB (1) GB740022A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4147726A (en) * 1976-11-08 1979-04-03 Phillips Petroleum Company Acid-catalyzed hydrolysis of organic hydroperoxide employing a polar solvent and phenol as reaction medium
CN104250221A (en) * 2013-06-28 2014-12-31 埃克森美孚化学专利公司 Process for concentrating a mixture containing organic hydroperoxide

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4147726A (en) * 1976-11-08 1979-04-03 Phillips Petroleum Company Acid-catalyzed hydrolysis of organic hydroperoxide employing a polar solvent and phenol as reaction medium
CN104250221A (en) * 2013-06-28 2014-12-31 埃克森美孚化学专利公司 Process for concentrating a mixture containing organic hydroperoxide
WO2014209578A1 (en) * 2013-06-28 2014-12-31 Exxonmobil Chemical Patents Inc. Process for concentrating a mixture containing organic hydroperoxide
CN104250221B (en) * 2013-06-28 2016-04-27 埃克森美孚化学专利公司 The method of the concentrated mixture containing organic hydroperoxide
US9464047B2 (en) 2013-06-28 2016-10-11 Exxonmobil Chemical Patents Inc. Process for concentrating a mixture containing organic hydroperoxide
EP3327003A1 (en) * 2013-06-28 2018-05-30 ExxonMobil Chemical Patents Inc. Process for concentrating a mixture containing organic hydroperoxide

Similar Documents

Publication Publication Date Title
US3243449A (en) Oxidation of hydrocarbons to borate esters
US4209465A (en) Decomposition of cumene hydroperoxide using a stable carbonium, tropylium or oxonium salt as the catalyst
GB740022A (en) Improvements relating to the preparation of phenols and cycloalkanones
GB1432426A (en) Process for the cleavage of hydroperoxides
US4210606A (en) Decomposition of cumene hydroperoxide with a halogen-substituted thiophenol catalyst
US2911442A (en) Production of oxygenated terpenes from alpha-pinene
US5220075A (en) Initiated peroxidation of secondary carbon in alkanes and cycloalkanes
GB700546A (en) Hydroperoxides
GB743736A (en) Phenol production
US4282382A (en) Production of cyclohexylbenzene hydroperoxide
GB1323181A (en) Manufacture of maleic anhydrides
US4210607A (en) Decomposition of cumene hydroperoxide using a stable nitrosonium or nitronium salt as the catalyst
GB1313360A (en) Rearrangement of aralkyl hydroperoxides to form phenols and carbonyl compounds
US2730550A (en) Production and stabilization of aromatic hydroperoxides
GB1022605A (en) Production of aralkyl hydroperoxides
US3050561A (en) Process for preparation of 2-cyclohexenone
US4297518A (en) Decomposition of cumene hydroperoxide with a homogeneous catalyst
US3914291A (en) Process for splitting cycloaliphatic hydroperoxides
US2674628A (en) Method of making alkyl-nitroaromatic ketones
GB777501A (en) Process for the production of hydroperoxides of partly-hydrogenated polynuclear, aromatic hydrocarbons
GB721700A (en) Process for the production of phenols and carbonyl compounds
US2883430A (en) Production of phenols
GB751598A (en) Meta-substituted phenols and method for their synthesis
US2717264A (en) Process for decomposing 1-alkylcyclohexyl hydroperoxides
SU707905A1 (en) Method of preparing alkylphenols