GB760315A - Improvements in and relating to the stabilisation of organic compounds - Google Patents

Improvements in and relating to the stabilisation of organic compounds

Info

Publication number
GB760315A
GB760315A GB17511/52A GB1751152A GB760315A GB 760315 A GB760315 A GB 760315A GB 17511/52 A GB17511/52 A GB 17511/52A GB 1751152 A GB1751152 A GB 1751152A GB 760315 A GB760315 A GB 760315A
Authority
GB
United Kingdom
Prior art keywords
diphenylamine
sec
alkyl
aralkyl
amino
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
GB17511/52A
Inventor
Leslie Victor Johnson
Charles Wickham Jones
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 GB17511/52A priority Critical patent/GB760315A/en
Priority to DEI7423A priority patent/DE1005515B/en
Publication of GB760315A publication Critical patent/GB760315A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines

Abstract

The invention comprises certain diphenylamine derivatives as new compounds, namely 4 - N - isopropylaminodiphenylamine, 4 - N - sec. - butylaminodiphenylamine, 4 - N - methylisopropylaminodiphenylamine, and 2 - N - sec. - butylaminodiphenylamine, and also a method of preserving aldehydes, petrols, (see Group III), mineral oils, fatty oils, and ethers from deteriorateion by oxidation by the incorporation of up to 2 per cent, preferably 0.001-1 per cent, of an aminodiphenylamine of the formula C6H5.NH.C6H4.NRR1, in which R is hydrogen, alkyl or aralkyl, and R1 is alkyl or aralkyl. Diphenylamine other than the above which may be so incorporated are the 4-N-benzylamino- or dibenzylamino, 4-N-(3,5,5-trimethylhexyl) - amino -, 4 - N - dimethylamino -, 4 - N - methylamino-, 2- or 3-N-sec.-butylamino-, and 4 - N - diphenylmethylamino - diphenylamines. The diphenylamines are made by (1) reductive alkylation of an amino-, nitro-, or nitrosodiphenylamine by hydrogenation in presence of an aliphatic or aromatic aldehyde or ketone, or (2) reacting alkyl- or aralkyl-substituted nitrosoaniline with phenylhydrazine. In examples of (1), 4-nitroso-, 4-amino-, and 4-nitro-diphenylamine are each hydrogenated in presence of a platinum-on-charcoal catalyst and of methyl ethyl ketone to give 4-N-sec.-butylaminodiphenylamine, and 4-aminodiphenylamine is similarly hydrogenated in presence of benzaldehyde to 4-N-benzylamino- and 4-N-dibenzylamino-diphenylamine, and as an example of (2), 4 - nitroso - N - methylisopropylaniline is reacted with phenylhydrazine in alcohol and ether. Examples also describe the stabilization of nonaldehyde, gasolines, a turbine oil, and boiled linseed oil with the above diphenylamine derivatives.ALSO:Petrols, mineral oils and fatty oils are preserved from deterioration by peroxide formation by incorporation of up to 2 per cent, preferably 0.001 to 1 per cent, by weight, of an aminodiphenylamine (see Group IV(b)) of the formula C6H5NH.C6-H4NRR1 in which R is hydrogen, alkyl, or alalkyl, and R1 is alkyl or aralkyl. Examples describe (1) the effect of adding 4-N-sec-butylamino-diphenylamine, and also 4-N-dimethylamino-, 4-N-methylamino-, 4-N-isopropylamino- 4-N-benzylamino-, 4-N-dibenzylamino, 4-N-(3, 5, 5-trimethylhexyl)amino-, 4-N-methylisopropylamino-, 2-N-sec-butylamino-, 4-N-diphenylmethylamino-diphenylamines to refined gasoline, (2) the addition of 4-N-isopropylamino-diphenylamine to a turbine oil and to boiled linseed oil.
GB17511/52A 1952-07-11 1952-07-11 Improvements in and relating to the stabilisation of organic compounds Expired GB760315A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB17511/52A GB760315A (en) 1952-07-11 1952-07-11 Improvements in and relating to the stabilisation of organic compounds
DEI7423A DE1005515B (en) 1952-07-11 1953-07-03 Process to delay or prevent the formation of peroxide or the self-oxidation of organic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB17511/52A GB760315A (en) 1952-07-11 1952-07-11 Improvements in and relating to the stabilisation of organic compounds

Publications (1)

Publication Number Publication Date
GB760315A true GB760315A (en) 1956-10-31

Family

ID=10096477

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17511/52A Expired GB760315A (en) 1952-07-11 1952-07-11 Improvements in and relating to the stabilisation of organic compounds

Country Status (2)

Country Link
DE (1) DE1005515B (en)
GB (1) GB760315A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0349153A2 (en) * 1988-06-28 1990-01-03 The Clorox Company Stabilizing system for liquid hydrogen peroxide compositions and compositions so stabilized
US5180514A (en) * 1985-06-17 1993-01-19 The Clorox Company Stabilizing system for liquid hydrogen peroxide compositions
US5232614A (en) * 1989-02-23 1993-08-03 Exxon Chemical Patents Inc. Lubricating oil compositions and additives for use therein
WO2007070282A1 (en) * 2005-12-14 2007-06-21 Chemtura Corporation Alkylation of n' -phenyl-n-alkylphenylenediamines in ionic liquid, n' -phenyl-n-alkyl(alkylphenylene) diamines produced thereby, and lubricant compositions containing same
CN116589364A (en) * 2023-04-06 2023-08-15 山东阳谷华泰化工股份有限公司 N-dicyclohexylmethyl-N' -phenyl-1, 4-phenylenediamine as well as preparation method and application thereof

Families Citing this family (3)

* 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
FR2634198B1 (en) * 1988-07-13 1990-09-14 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF N-ALKYL N (PRIME) -PHENYLPARAPHENYLENEDIAMINES
EP0538195A3 (en) * 1991-10-18 1993-06-23 Ciba-Geigy Ag N-allyl/benzyl substituted phenylenediamine stabilizers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2348290A (en) * 1941-03-28 1944-05-09 Tide Water Associated Oil Comp Stabilized motor fuel

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5180514A (en) * 1985-06-17 1993-01-19 The Clorox Company Stabilizing system for liquid hydrogen peroxide compositions
EP0349153A2 (en) * 1988-06-28 1990-01-03 The Clorox Company Stabilizing system for liquid hydrogen peroxide compositions and compositions so stabilized
EP0349153A3 (en) * 1988-06-28 1990-03-14 The Clorox Company Stabilizing system for liquid hydrogen peroxide compositions and compositions so stabilized
US5232614A (en) * 1989-02-23 1993-08-03 Exxon Chemical Patents Inc. Lubricating oil compositions and additives for use therein
WO2007070282A1 (en) * 2005-12-14 2007-06-21 Chemtura Corporation Alkylation of n' -phenyl-n-alkylphenylenediamines in ionic liquid, n' -phenyl-n-alkyl(alkylphenylene) diamines produced thereby, and lubricant compositions containing same
CN116589364A (en) * 2023-04-06 2023-08-15 山东阳谷华泰化工股份有限公司 N-dicyclohexylmethyl-N' -phenyl-1, 4-phenylenediamine as well as preparation method and application thereof

Also Published As

Publication number Publication date
DE1005515B (en) 1957-04-04

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