GB727247A - Improvements in and relating to the preparation of inhibitors of oxidation and of related undesirable reactions - Google Patents

Improvements in and relating to the preparation of inhibitors of oxidation and of related undesirable reactions

Info

Publication number
GB727247A
GB727247A GB614552A GB614552A GB727247A GB 727247 A GB727247 A GB 727247A GB 614552 A GB614552 A GB 614552A GB 614552 A GB614552 A GB 614552A GB 727247 A GB727247 A GB 727247A
Authority
GB
United Kingdom
Prior art keywords
alkyl group
phenylene diamine
dimethyl
methyl
ketone
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
GB614552A
Inventor
David Gwyn Jones
George Robert Fulton
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB614552A priority Critical patent/GB727247A/en
Publication of GB727247A publication Critical patent/GB727247A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
    • C11B5/005—Amines or imines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/16—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen
    • C09K15/18—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen containing an amine or imine moiety
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C10M2207/28—Esters
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Abstract

A process for the production of compounds having a structural formula <FORM:0727247/IV (b)/1> in which R is either hydrogen or an alkyl group, R1 is an alkyl group and R2 is a secondary alkyl group which may contain an aryl substituent, comprises reductively alkylating the corresponding amines having a structure <FORM:0727247/IV (b)/2> by hydrogenation in the presence of the appropriate ketone, under conditions which do not lead to the occurrence of a substantial amount of nuclear hydrogenation. The reaction is effected catalytically using a catalyst comprising copper (which may be in foraminate form or on a support such as zinc oxide, alumina, kieselguhr or pumice) or a metal of Group VIII of the periodic system such as nickel (foraminate or Raney form) or platinum (finely divided or on a support). The reduction is effected in liquid phase, conveniently in a medium of excess ketone, a ketone/amine ratio of 10 : 1 being suitable. Temperatures of 120 DEG to 200 DEG C. and pressures of 25 to 100 atmospheres may be used. In an example N-dimethyl-p-phenylene diamine (obtained by the catalytic reduction of N-dimethyl-p-nitroso-aniline) is reacted with methyl ethyl ketone and hydrogen at 50 atmospheres and 160 DEG C. to give N-dimethyl-N1-sec.-butyl-p-phenylene diamine. N-Methyl-N1-(diphenylmethyl)-p-phenylene diamine may be produced similarly by hydrogenating a mixture of N - methyl - p - phenylene diamine and benzophenone. The products are suitable for the stabilization of organic compounds liable to deterioration arising from free-radical chain reactions propagated by oxidation or polymerization, and may be added for that purpose to aldehydes, ethers, petrols, fatty oils and lubricating oils comprising esters or hydrocarbons, suitably in amounts of 0.0002 to 3 per cent by weight. Specification 508,129 is referred to. According to the Provisional Specification, R1 and R2 may also represent aryl radicals.ALSO:Amine derivatives of the formula <FORM:0727247/III/1> in which R is either hydrogen or an alkyl group, R1 is an alkyl group and R2 is a secondary alkyl group which may contain an aryl substituent are suitable for the stabilization of organic compounds liable to deterioration arising from free-radical chain reactions and for that purpose may be added to petrols, fatty oils of vegetable or animal origin comprising esters of long chain saturated or unsaturated carboxylic acids and lubricating oils comprising esters or hydrocarbons, suitably in amounts of 0.0002 to 3 per cent. by weight. Compounds of the above formula, the preparation of which is described (see Group IV (b)), include N-dimethyl-N1-sec butyl-p-phenylene diamine (shown as an antioxidant for petrol) and N-methyl-N1-(diphenylmethyl)-p-pheny. lene diamine. Specification 508,129 is referred to-According to the Provisional Specification, R1 and R2 may also represent aryl radicals.
GB614552A 1952-03-10 1952-03-10 Improvements in and relating to the preparation of inhibitors of oxidation and of related undesirable reactions Expired GB727247A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB614552A GB727247A (en) 1952-03-10 1952-03-10 Improvements in and relating to the preparation of inhibitors of oxidation and of related undesirable reactions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB614552A GB727247A (en) 1952-03-10 1952-03-10 Improvements in and relating to the preparation of inhibitors of oxidation and of related undesirable reactions

Publications (1)

Publication Number Publication Date
GB727247A true GB727247A (en) 1955-03-30

Family

ID=9809232

Family Applications (1)

Application Number Title Priority Date Filing Date
GB614552A Expired GB727247A (en) 1952-03-10 1952-03-10 Improvements in and relating to the preparation of inhibitors of oxidation and of related undesirable reactions

Country Status (1)

Country Link
GB (1) GB727247A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1156817B (en) * 1956-07-13 1963-11-07 Ici Ltd Process for the color stabilization of aromatic amines containing less than 1% by weight of primary aromatic amines
US5232614A (en) * 1989-02-23 1993-08-03 Exxon Chemical Patents Inc. Lubricating oil compositions and additives for use therein

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1156817B (en) * 1956-07-13 1963-11-07 Ici Ltd Process for the color stabilization of aromatic amines containing less than 1% by weight of primary aromatic amines
US5232614A (en) * 1989-02-23 1993-08-03 Exxon Chemical Patents Inc. Lubricating oil compositions and additives for use therein

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