GB754053A - Splitting up of hydroperoxides of aromatic hydrocarbons by means of an acid catalyst - Google Patents

Splitting up of hydroperoxides of aromatic hydrocarbons by means of an acid catalyst

Info

Publication number
GB754053A
GB754053A GB21805/54A GB2180554A GB754053A GB 754053 A GB754053 A GB 754053A GB 21805/54 A GB21805/54 A GB 21805/54A GB 2180554 A GB2180554 A GB 2180554A GB 754053 A GB754053 A GB 754053A
Authority
GB
United Kingdom
Prior art keywords
hydroperoxide
tolyl
hydrogen chloride
ethane
gas
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
GB21805/54A
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 GB754053A publication Critical patent/GB754053A/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
    • 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
    • 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
    • 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

Landscapes

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

Abstract

Phenols and aldehydes or ketones are formed by the cleavage of aromatic hydroperoxides by passing a gas containing 1-5 per cent by volume of hydrogen chloride through a solution of the hydroperoxide in a hydrocarbon. The solution may be of the hydroperoxide in its parent hydrocarbon prepared by partial oxidation of that hydrocarbon. Hydroperoxides specified are those of isopropyl benzene, p-methyl isopropyl benzene, ethyl benzene, diphenyl methane, 1:1 diphenyl ethane, di-p-tolyl methane, 1:1 di-p-tolyl ethane, and cyclohexyl benzene, which are converted according to the process of the invention to phenols, such as phenol or p-cresol, and aldehydes such as acetaldehyde, benzaldehyde or p-tolualdehyde, or ketones such as acetone, acetophenone, p-methyl-acetophenone or cyclohexanone. The gas catalyst, consisting of an inert gas such as air, carbon dioxide or nitrogen containing hydrogen chloride, is passed continuously or intermittently through the stirred solution of the hydroperoxide maintained at below 50 DEG C. The catalyst may be recycled. On completion of the reaction, the gas catalyst may be removed by passing the inert gas alone through the reaction mixture which may then be neutralized with dry ammonia gas, alkali metal hydroxides, soda, calcium oxide, or calcium carbonate, and the products isolated by distillation, or the phenols may be extracted with an alkali metal hydroxide solution. In an example, air containing hydrogen chloride is passed through a stirred solution of 1:1 di-p-tolyl ethane hydroperoxide in 1:1 di-p-tolyl ethane with cooling to form p-cresol and p-methyl acetophenone. Other examples include the cleavage of cumene hydroperoxide under similar conditions to form phenol and acetone and the cleavage of di-tolyl methane with hydrogen chloride in nitrogen to form cresols and tolualdehydes.
GB21805/54A 1953-07-30 1954-07-26 Splitting up of hydroperoxides of aromatic hydrocarbons by means of an acid catalyst Expired GB754053A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL754053X 1953-07-30

Publications (1)

Publication Number Publication Date
GB754053A true GB754053A (en) 1956-08-01

Family

ID=19825219

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21805/54A Expired GB754053A (en) 1953-07-30 1954-07-26 Splitting up of hydroperoxides of aromatic hydrocarbons by means of an acid catalyst

Country Status (1)

Country Link
GB (1) GB754053A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2881222A (en) * 1956-03-15 1959-04-07 Allied Chem Removal of acidic impurities from crude phenolic products
JPS4945854B1 (en) * 1969-06-18 1974-12-06

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2881222A (en) * 1956-03-15 1959-04-07 Allied Chem Removal of acidic impurities from crude phenolic products
JPS4945854B1 (en) * 1969-06-18 1974-12-06

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