GB923520A - A process for the preparation of alkylated phenolic compounds - Google Patents

A process for the preparation of alkylated phenolic compounds

Info

Publication number
GB923520A
GB923520A GB26295/60A GB2629560A GB923520A GB 923520 A GB923520 A GB 923520A GB 26295/60 A GB26295/60 A GB 26295/60A GB 2629560 A GB2629560 A GB 2629560A GB 923520 A GB923520 A GB 923520A
Authority
GB
United Kingdom
Prior art keywords
tert
dialkyl
butyl
alcohol
dialkylphenol
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
GB26295/60A
Inventor
Rupert C Morris
Albert L Rocklin
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij 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
Priority claimed from US832905A external-priority patent/US3085003A/en
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB923520A publication Critical patent/GB923520A/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
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
    • 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
    • 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
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups

Landscapes

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

Abstract

One or more alkylated phenols are prepared by a process which comprises (a) condensing at a temperature below 100 DEG C. a 2,4- or 2,6-dialkylphenol with formaldehyde in the presence of a basic catalyst and a monohydric secondary or tertiary alkanol, there being at least 0.1 mol of alkanol per mol of dialkylphenol, so as to form a 3,5-dialkyl-4-or-6-hydroxybenzyl alcohol and (b) condensing in the presence of a basic catalyst and a monohydric secondary or tertiary alkanol the 3,5-dialkyl-4-or-6-hydroxybenzyl alcohol with respectively a 2,6- or 2,4-dialkylphenol to yield respectively a bis(3,5-dialkyl-4-or-6-hydroxyphenyl) methane. The product of step (a) may also be catalytically hydrogenated at a pressure in excess of 7.8 atmospheres to form a 2,4-dialkyl-6-methylphenol or 2,6-dialkyl-4-methylphenol. The alkylphenols are used as antioxidants. An apparatus for carrying out the processes is described. In an example 2,6-di-tert-butyl-phenol is condensed at 10 degrees with formadehyde in tert.-butyl alcohol containing pottassium hydroxide, the mixture neutralised with carbon dioxide and tert.-butanol is distilled off to give a residue of 3,5-di-tert.-butyl-4-hydroxy alcohol. This substituted benzyl alcohol is either reacted at 77 DEG C. with 2,6-di-tert.-buty-phenol in tert.-butanol containing potassium hydroxide and the mixture cooled to crystallise bis(3,5-di-tert.-butyl-4-hydroxyphenyl) methane or hydrogenated under pressure in isopropanol using a copper chromite catalyst to give 2,6-di-tert.-buty-4-methylphenol. Specifications 806,961, 862,261 889,321 and 893,896 are referred to.
GB26295/60A 1959-07-30 1960-07-28 A process for the preparation of alkylated phenolic compounds Expired GB923520A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US83047559A 1959-07-30 1959-07-30
US832905A US3085003A (en) 1959-07-30 1959-08-11 Compositions stabilized with 3, 5-dialkyl-4 hydroxybenzyl alcohol
US85624259A 1959-11-30 1959-11-30

Publications (1)

Publication Number Publication Date
GB923520A true GB923520A (en) 1963-04-10

Family

ID=27420219

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26295/60A Expired GB923520A (en) 1959-07-30 1960-07-28 A process for the preparation of alkylated phenolic compounds

Country Status (1)

Country Link
GB (1) GB923520A (en)

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