GB736943A - A process for the production of substituted alkanes - Google Patents

A process for the production of substituted alkanes

Info

Publication number
GB736943A
GB736943A GB32551/53A GB3255153A GB736943A GB 736943 A GB736943 A GB 736943A GB 32551/53 A GB32551/53 A GB 32551/53A GB 3255153 A GB3255153 A GB 3255153A GB 736943 A GB736943 A GB 736943A
Authority
GB
United Kingdom
Prior art keywords
hydroperoxide
mercaptan
ethyl
acid
cumene 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
GB32551/53A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB736943A publication Critical patent/GB736943A/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
    • 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

Substituted alkanes having two hydroxyaryl groups attached to a single carbon atom of the alkane radical are prepared by subjecting an aromatic hydroperoxide represented by the general formula <FORM:0736943/IV (b)/1> in which Ar represents an aryl or alkaryl group, R1 represents a hydrogen atom or an alkyl group and R2 represents an alkyl group, to the catalytic influence of a strong acid and a mercaptan. A monohydric phenol may be present, in an amount by weight at least equal to that of the hydroperoxide. Generally the reaction proceeds so that the hydroxyl groups occupy the para positions if this is possible. The quantity of mercaptan used is between 0.5 and 5.0 per cent of the hydroperoxide and methyl mercaptan or ethyl mercaptan is preferred. The acids used have a dissociation constant greater than 10-3, e.g. sulphuric or hydrochloric acid. The most advantageous weight ratio of acid to hydroperoxide lies between 2 : 15 and 2 : 1. The hydroperoxide is added to the acidic reaction medium, preferably at a temperature between 0 DEG and 10 DEG C. and reaction proceeds preferably at temperatures between 0 DEG and 60 DEG C. The presence of inert organic solvents, e.g. hydrocarbons, lower alcohols or ethers is generally desirable. The process is especially important for the preparation of 2 : 2-di-(4-hydroxyphenyl)propane using cumene hydroperoxide as the starting material. Other hydroperoxides specified include a - phenylethyl, a - ethyl-a - methylbenzyl, a ,a - dimethyl - p - methylbenzyl, and a ,a - dimethyl naphthylmethyl hydroperoxides. In examples: (1) a mixture of phenol and sulphuric acid is reacted with cumene hydroperoxide in the presence of ethyl mercaptan; (2) the processes of reacting sulphuric acid and cumene hydroperoxide with and without ethyl mercaptan are compared; (3) normal heptane is saturated with anhydrous hydrogen chloride and reacted with a mixture of cumene hydroperoxide and ethyl mercaptan. Specification 721,336 is referred to.
GB32551/53A 1952-11-24 1953-11-24 A process for the production of substituted alkanes Expired GB736943A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US736943XA 1952-11-24 1952-11-24

Publications (1)

Publication Number Publication Date
GB736943A true GB736943A (en) 1955-09-14

Family

ID=22115215

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32551/53A Expired GB736943A (en) 1952-11-24 1953-11-24 A process for the production of substituted alkanes

Country Status (1)

Country Link
GB (1) GB736943A (en)

Similar Documents

Publication Publication Date Title
Kharasch et al. The Chemistry of Hydroperoxides. VI. The thermal decomposition of α-cumyl hydroperoxide
Arnett et al. Effect of Structure on Reactivity. 1 III. Aminolysis of Esters with Primary Amines2
US3267165A (en) Preparation of mesitylene by dehydro-condensation of acetone
US2218640A (en) Production of aliphatic hydrocarbons of the diolefin series
GB711122A (en) Improvements in or relating to the production of bis(hydroxyphenyl) compounds
GB736943A (en) A process for the production of substituted alkanes
US2446145A (en) Carbonate-haloformate of glycerol and method of producing same
US2560049A (en) Alkylphenol sulfoxides
US2525672A (en) Preparation of alkynylalkenylcarbinols
US2482748A (en) 4,4&#39;-isopropylidene bis
US3187020A (en) Process for preparing diazides
US2578206A (en) Alkenylation of phenols
GB721336A (en) A process for the production of substituted alkanes and the resulting substituted alkanes
US2353282A (en) Preparation of substituted phenols
US1005217A (en) Process of producing divinyl.
US3064056A (en) Process for the production of disulphides and polysulphides containing hydroxyl groups
US2505870A (en) Secondary and tertiary alkylthiol amines and their production
US3287417A (en) Bis-(substituted thiol) dichloromethanes
US3126404A (en) Biguanide adducts of phenyl isocyanate
US2511961A (en) Beta-nitroalkyi
GB754862A (en) Process and apparatus for decomposing organic hydroperoxides
US2674628A (en) Method of making alkyl-nitroaromatic ketones
US2938930A (en) Preparation of chlormethylated alkyl aromatic hydrocarbons
US3254130A (en) Method of preparing an organic peroxide
US2658071A (en) Pentachlorophenyl ester of trichloroacetic acid