GB1227419A - - Google Patents

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Publication number
GB1227419A
GB1227419A GB1227419DA GB1227419A GB 1227419 A GB1227419 A GB 1227419A GB 1227419D A GB1227419D A GB 1227419DA GB 1227419 A GB1227419 A GB 1227419A
Authority
GB
United Kingdom
Prior art keywords
dialkyl
butyl
formula
alkyl group
benzene
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
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 filed Critical
Publication of GB1227419A publication Critical patent/GB1227419A/en
Expired legal-status Critical Current

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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
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of SO3H groups or a derivative thereof
    • 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
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
    • 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
    • C07C37/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by exchange of hydrocarbon groups, which may be substituted, from the same of other compounds, e.g. transalkylation

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

Abstract

1,227,419. Dialkyl phenols. JAPAN GAS CHEMICAL CO. Inc. 16 April, 1968 [14 April, 1967; 21 April, 1967], No. 17848/68. Heading C2C. [Also in Division C5] A process for the production of a 2,6-dialkyl phenol comprises reacting a 2,6-dialkyl-4-talkyi phenol of the Formula I with an aromatic hydrocarbon of the Formula II in the presence of a Friedel-Crafts catalyst at a temperature of from - 20‹ to 100‹ C. to transfer the + -alkyl group to said aromatic hydrocarbon, wherein R 1 denotes a C 4-7 t-alkyl group, R 2 and R 3 each denotes a C 1-4 normal alkyl group and R 4 and R 5 each denotes either hydrogen or a C 1-4 normal alkyl group located mutually in the o- or m-position when neither R 4 nor R 5 is hydrogen. In a preferred embodiment the compound of Formula I is formed from the corresponding 1,3-dialkyl-5-t-alkyl benzene by sulphonation followed by alkali fusion or by chlorination followed by hydrolysis, and is then reacted with a 1,3-dialkyl benzene having the formula wherein R 2 and R 3 are as defined above in the presence of a Friedel-Crafts catalyst at a temperature of -20‹ to 100‹ C. to form the 2,6- dialkylphenol and the 1,3-dialkyl-5-t-alkyl benzene and circulating the latter to the first stage of the reaction for re-use. 2 - Chioro - 5 - t - butyl - m - xylene is prepared by chlorinating 5-t-butyl-m-xylene using molecular chlorine. 2,6 - Dimethyl - 4 - t - butyl benzene sulphonate was prepared by reacting 5-t-butyl-m-xylene with conc. sulphuric acid followed by sodium chloride. 2,6 - Dimethyl - 4 - t - butyl phenol was prepared by alkali fusion of the corresponding sulphonate or by hydrolysis of the corresponding chloride.
GB1227419D 1967-04-14 1968-04-16 Expired GB1227419A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2374067 1967-04-14
JP2547767 1967-04-21

Publications (1)

Publication Number Publication Date
GB1227419A true GB1227419A (en) 1971-04-07

Family

ID=26361146

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1227419D Expired GB1227419A (en) 1967-04-14 1968-04-16

Country Status (1)

Country Link
GB (1) GB1227419A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2499067A1 (en) * 1980-03-14 1982-08-06 Ugine Kuhlmann PROCESS FOR THE PREPARATION OF PRACTICALLY PURE META-ISOPROPYLPHENOL
US6939998B2 (en) 2002-09-06 2005-09-06 The University Of Southern Mississippi Research Foundation Preparation of 5-tert-butyl-metaxylene using a solid active clay catalyst

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2499067A1 (en) * 1980-03-14 1982-08-06 Ugine Kuhlmann PROCESS FOR THE PREPARATION OF PRACTICALLY PURE META-ISOPROPYLPHENOL
US6939998B2 (en) 2002-09-06 2005-09-06 The University Of Southern Mississippi Research Foundation Preparation of 5-tert-butyl-metaxylene using a solid active clay catalyst

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee