GB889116A - A process for the production of antioxidants from alkyl phenols and formaldehyde - Google Patents

A process for the production of antioxidants from alkyl phenols and formaldehyde

Info

Publication number
GB889116A
GB889116A GB17717/58A GB1771758A GB889116A GB 889116 A GB889116 A GB 889116A GB 17717/58 A GB17717/58 A GB 17717/58A GB 1771758 A GB1771758 A GB 1771758A GB 889116 A GB889116 A GB 889116A
Authority
GB
United Kingdom
Prior art keywords
acid
catalyst
formaldehyde
methyl
antioxidants
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
GB17717/58A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB889116A publication Critical patent/GB889116A/en
Expired legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C7/00—Non-inflatable or solid tyres
    • 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
    • C07C37/115—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 acetals
    • 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
    • C07C37/14—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 addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/28—Chemically modified polycondensates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Stereophonic System (AREA)

Abstract

Resinous antioxidants are produced by alkylating a p-monoalkyl phenol, the alkyl group of which contains 1-5 carbon atoms, with an olefin or an alcohol and condensing the resulting crude reaction product without any purification with formaldehyde in the presence of an acidic condensation catalyst. p-Methyl, ethyl or propyl phenol may be alkylated with ethylene, propylene, isobutylene or isopentene or with tert.-butanol, cyclohexanol, 2-methyl cyclohexanol or isopentanol in the presence of a catalyst, e.g. an acid activated bleaching earth, and the intermediate crude reaction product condensed with formaldehyde, in the form of paraformaldehyde or as an aqueous solution, in the presence of an acid catalyst, e.g. an acid activated bleaching earth, sulphuric acid or hydrochloric acid. The resinous products may be used as antioxidants for natural rubber and synthetic elastomers, e.g. polymers of conjugated diolefins; copolymers of diolefins and polymerizable vinyl compounds such as styrene, a -methyl styrene, acrylonitrile, methacrylonitrile, acrylates and methacrylates; and copolymers of iso-olefins with small amounts of conjugated dienes. Rubber mixtures exemplified include, in addition to the antioxidant (1) pale crepe, stearic acid, tetramethyl thiurammonosulphide, zinc oxide, titanium dioxide, barium sulphate and sulphur and (2) chlorobutadiene polymerizate, magnesium oxide, zinc oxide, paraffin oil, stearic acid, active silicic acid and ethylene thiourea. Specifications 677,584, 677,585 and 776,518 are referred to.ALSO:Antioxidants are produced by alkylating a p-monoalkyl phenol, the alkyl group of which contains 1-5 carbon atoms, with an olefin or an alcohol and condensing the resultant crude reaction product without any purification with formaldehyde in the presence of an acidic catalyst. p-Methyl, ethyl or propyl phenol may be alkylated with ethylene, propylene, isobutylene or isopentene or with tert-butanol, cyclohexanol, 2-methyl cyclohexanol or isopentanol in the presence of a catalyst, e.g. an acid activated bleaching earth, and the intermediate crude reaction product condensed with formaldehyde, in the form of paraformaldehyde or as an aqueous solution, in the presence of an acid catalyst, e.g. an acid activated bleaching earth, sulphuric acid, or hydrochloric acid. Specifications 677,584, 677,585 and 776,518 are referred to.
GB17717/58A 1957-06-03 1958-06-03 A process for the production of antioxidants from alkyl phenols and formaldehyde Expired GB889116A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE889116X 1957-06-03

Publications (1)

Publication Number Publication Date
GB889116A true GB889116A (en) 1962-02-07

Family

ID=6834416

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17717/58A Expired GB889116A (en) 1957-06-03 1958-06-03 A process for the production of antioxidants from alkyl phenols and formaldehyde

Country Status (2)

Country Link
FR (1) FR889116A (en)
GB (1) GB889116A (en)

Also Published As

Publication number Publication date
FR889116A (en) 1943-12-31

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