GB497939A - Improvements in retarding the oxidation of substances sensitive to oxidation - Google Patents

Improvements in retarding the oxidation of substances sensitive to oxidation

Info

Publication number
GB497939A
GB497939A GB1794437A GB1794437A GB497939A GB 497939 A GB497939 A GB 497939A GB 1794437 A GB1794437 A GB 1794437A GB 1794437 A GB1794437 A GB 1794437A GB 497939 A GB497939 A GB 497939A
Authority
GB
United Kingdom
Prior art keywords
thiol
ethane
anilido
oxidation
aniline
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
GB1794437A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB1794437A priority Critical patent/GB497939A/en
Publication of GB497939A publication Critical patent/GB497939A/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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
    • C10L1/2412—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides sulfur bond to an aromatic radical
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2443—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles

Landscapes

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

Abstract

The oxidation of substances sensitive to oxidation is retarded by the addition of small amounts of compounds of the general formula <FORM:0497939/III/1> In the formula, R1 and R2 are hydrogen or an aliphatic, hydroaromatic, aromatic or heterocyclic radicle, which may be substituted in any way, or R1 and R2 together with the nitrogen atom may also be members of a heterocyclic ring; R3 is an aliphatic radicle, in particular an alkylene group which may also contain acyclic substituents; R4 is hydrogen or any other radicle which can be formed by substitution or salt-formation on the mercapto group or oxidation of the same to a disulphide, e.g. it can be as described for R1 and R2, or it may correspond to the group <FORM:0497939/III/2> , or it may be a metal. The following compounds are mentioned as suitable: b -anilido-ethane-monothiol, bis-(b -mercapto-ethyl)-aniline, a (b -naphthylamino)-ethane-thiol, b -dodecyl-amino-propane-thiol, b -cyclohexylamino-b -methyl-ethane-thiol, piperidino-ethane-thiol, b -anilido-ethane-disulphide, bis-(b -anilido-ethyl)-thioether and b -anilido-ethane-lead-mercaptide. The amounts used are generally less than 5 per cent of the substance to be protected. In the examples: (1) a lubricating oil is protected by the use of b -anilido-ethane-thiol, a - or b -naphthylamino-ethane-thiol, bis-(b -methyl-b -mercapto-ethyl)-aniline, octodecylamino-isopropyl-thiol and cyclohexylamino-propane-thiol; (2) aniline is protected by anilido-ethane-thiol; (3) the oxidation of a mixture of chlorinated diphenyl and polymerized vinyl carbazole is retarded by anilido-ethane-thiol,; (4) the oxidation of the reaction product obtained by boiling an artificial resin with Chinese wood oil is inhibited by anilido-ethane-thiol; (5) anilido-ethane-thiol prevents the ageing of polymerized vinylisobutyl ether. These substances are also used to retard the oxidation of fats and fatty oils mineral coal tar, natural and synthetic rubbers, synthetic resins in general, polymerization products of olefines, lacquers and films of cellulose derivatives and cellulose artificial masses, phenols, amines and varnishes.ALSO:The oxidation of substances sensitive to oxidation is retarded by the addition of small amounts of compounds of the general formula <FORM:0497939/IV/1> In the formula R1 and R2 are hydrogen or an aliphatic, hydroaromatic, aromatic or heterocyclic radicle, which may be substituted in any way, or R1 and R2 together with the nitrogen atom may also be members of a heterocyclic ring; R3 is an aliphatic radicle, in particular an alkylene group which may also contain acyclic substituents; R4 is hydrogen or any other radicle which can be formed by substitution or salt-formation on the mercapto group or oxidation of the same to a disulphide, e.g. it can be as described for R1 and R2, or it may correspond to the group <FORM:0497939/IV/2> , or it may be a metal. The following compounds are mentioned as suitable: b -anilido-ethanemonothiol, bis-(b -mercapto-ethyl)-aniline, a (b -naphthylamino) - ethane - thiol, b - dodecylamino - propane - thiol, b - cyclohexylamino - b -methyl-ethane-thiol, piperidino-ethane-thiol, b - anilido - ethane - disulphide, bis - (b - anilidoethyl)-thioether and b -anilido-ethane-lead-mercaptide. The amounts used are generally less than 5 per cent of the substance to be protected. In the examples: (1) a lubricating oil is protected by the use of b -anilido-ethane-thiol, a -or b - naphthylamino - ethane - thiol, bis - (b -methyl-b -mercapto-ethyl)-aniline, octodecylamino - isopropyl - thiol and cyclohexylaminopropane-thiol; (2) aniline is protected by anilido-ethane-thiol; (3) the oxidation of a mixture of chlorinated diphenyl and polymerized vinyl carbazole is retarded by anilido-ethane-thiol; (4) the oxidation of the reaction product obtained by boiling an artificial resin with Chinese wood oil is inhibited by anilido-ethane-thiol; (5) anilido-ethane-thiol prevents the ageing of polymerized vinylisobutyl ether. These substances are also used to retard the oxidation of fats and fatty oils, mineral coal tar, natural and synthetic rubbers, synthetic resins in general, polymerization products of olefines, lacquers and films of cellulose derivatives and cellulose artificial masses, phenols, amines, and varnishes.ALSO:The oxidation of substances sensitive to oxidation is retarded by the addition of small amounts of compounds of the general formula <FORM:0497939/V/1> In the formula R1 and R2 are hydrogen or an aliphatic hydroaromatic, aromatic or heterocyclic radicle, which may be substituted in any way, or R1 and R2 together with the nitrogen atom may also be members of a heterocyclic ring; R3 is an aliphatic radicle, in particular an alkylene group which may also contain acyclic substituents R4 is hydrogen or any other radicle which can be formed by substitution or salt-formation on the mercapto group or oxidation of the same to a disulphide, e.g. it can be as described for R1 and R2, or it may correspond to the group <FORM:0497939/V/2> , or it may be a metal. The following compounds are mentioned as suitable: b -anilido-ethane-monothiol, bis-(b -mercapto-ethyl)-aniline, a (b -naphthylamino)-ethane-thiol, b -dodecyl-amino-propane-thiol, b -cyclohexylamino-b -methyl-ethane-thiol, piperidino-ethane-thiol, b -anilido-ethane-disulphide, bis-(b -anilido-ethyl)-thioether and b -anilido-ethane-lead-mercaptide. The amounts used are generally less than 5 per cent of the substance to be protected. In the examples: (1) a lubricating oil is protected by the use of b -anilido-ethane-thiol, a - or b -naphthyl-amino-ethane-thiol, bis-(b -methyl-b -mercapto-ethyl)-aniline, octodecylamino-isopropyl-thiol and cyclohexylamino-propane-thiol; (2) aniline is protected by anilido-ethane-thiol; (3) the oxidation of a mixture of chlorinated diphenyl and polymerized vinyl carbazole is retarded by anilido-ethane-thiol; (4) the oxidation of the reaction product obtained by boiling an artificial resin with Chinawood oil is inhibited by anilido-ethane-thiol; (5) anilido-ethane-thiol prevents the ageing of polymerized vinyl-isobutyl ether. These substances are also used to retard the oxidation of fats and fatty oils, mineral coal tar, natural and synthetic rubbers, synthetic resins in general, polymerization products of olefines, lacquers and films of cellulose derivatives and cellulose artificial masses, phenols, amines, and varnishes.
GB1794437A 1937-06-28 1937-06-28 Improvements in retarding the oxidation of substances sensitive to oxidation Expired GB497939A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1794437A GB497939A (en) 1937-06-28 1937-06-28 Improvements in retarding the oxidation of substances sensitive to oxidation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1794437A GB497939A (en) 1937-06-28 1937-06-28 Improvements in retarding the oxidation of substances sensitive to oxidation

Publications (1)

Publication Number Publication Date
GB497939A true GB497939A (en) 1938-12-28

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Family Applications (1)

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GB1794437A Expired GB497939A (en) 1937-06-28 1937-06-28 Improvements in retarding the oxidation of substances sensitive to oxidation

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GB (1) GB497939A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2689867A (en) * 1948-12-03 1954-09-21 Phillips Petroleum Co Preparation of alkyl aminosulfides
US2823515A (en) * 1954-04-09 1958-02-18 California Research Corp Auto-ignition method
US2980599A (en) * 1956-01-09 1961-04-18 Martin Co Moderator composition
US5024774A (en) * 1987-06-09 1991-06-18 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2689867A (en) * 1948-12-03 1954-09-21 Phillips Petroleum Co Preparation of alkyl aminosulfides
US2823515A (en) * 1954-04-09 1958-02-18 California Research Corp Auto-ignition method
US2980599A (en) * 1956-01-09 1961-04-18 Martin Co Moderator composition
US5024774A (en) * 1987-06-09 1991-06-18 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions

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