US2361339A - Metal deactivators - Google Patents

Metal deactivators Download PDF

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Publication number
US2361339A
US2361339A US339508A US33950840A US2361339A US 2361339 A US2361339 A US 2361339A US 339508 A US339508 A US 339508A US 33950840 A US33950840 A US 33950840A US 2361339 A US2361339 A US 2361339A
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Prior art keywords
oxidation
amino
copper
compounds
deactivators
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Expired - Lifetime
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US339508A
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English (en)
Inventor
Ellis R White
Ernest L Walters
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SHEIL DEV Co
SHEIL DEVELOPMENT Co
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SHEIL DEV Co
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Priority to NL66835D priority Critical patent/NL66835C/xx
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Priority to US339508A priority patent/US2361339A/en
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Publication of US2361339A publication Critical patent/US2361339A/en
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    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • 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
    • C10M133/22—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms containing a carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers
    • G03C5/3053—Tensio-active agents or sequestering agents, e.g. water-softening or wetting agents
    • 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
    • C10M2207/40—Fatty vegetable or animal oils
    • 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
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • 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
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
    • 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
    • C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
    • 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
    • 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
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • 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
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms 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
    • 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
    • C10M2219/089—Overbased salts
    • 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
    • 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/17—Electric or magnetic purposes for electric contacts

Definitions

  • This invention relates to a method for the stabilization of organic substances and particularly to the protection or organic substances against deterioration by oxidation which is catalyzed by the presence of or by contact with certain oxidation promoters.
  • An important application of this invention resides in the reduction of the amount of gum formed in gasoline during storage due to the presence or small amounts of certain metals, their compounds or both.
  • deactivators appear to be specific for certain metals and their compounds. Diflerent types of organic substances may be protected from the catalytic effect of metal oxidation promoters.
  • the deactivators must be at least slightly soluble in the organic substance by itself or in the presence of a mutual solvent. Neutral and basic substances are in general more susceptible to the action of the deactivators than acids.
  • Aldehydes suitable to form deactivators with said aliphatic alcohols are, for example, salicylaldehyde, the homo-salicyclaldehydes, trimethyl salicylaldehyde, isobutyl salicylaldehyde, ortho hydroxy naphthyl aldehyde, corresponding aldehydes of anthracene, etc.
  • the aldehydes may contain substitution radicals, such as alkyl, halogen, amino, imino, hydrazine, ether, thioether, etc. radicals.
  • Aliphatic compounds of not more than 12 carbon atoms having one primary radical amine capable of forming deactivators with the salicylaldehydes mentioned previously are for example.
  • R is an aliphatic radical of 2 to 12 carbon atoms and which may contain the elements oxygen, sulfur or nitrogen such as mono ethanolamine, mono butanolamine, mono dodecanolamine, 1 amino 2 pentan'ol, 4 amino 2 pentanol,
  • hydroxy ethyl amino ethyl ether hydroxy propyl amino ethyl ether, hydroxy propyl amino butyl ether, hydroxy propyl amino propyl ether, 1 hydroxy 2 methyl butyl amino propyl ether, the corresponding thio and imino ethera, suli'oxides and suli'ones, such as hydroxy ethyl amino ethyl sulfoxidcs, hydroxy butyl amino ethyl sulfone, ketones and thioketones such as amino methyl isopropyl ketone, 1 hydroxy 5 amino pentanone 3, 1' hydroxy 5 amino pentathlonone 3, hydroxy activators is well known and may be illustrated by the following equation:
  • the aliphatic chain of the amine should contain not more than 12 carbon atoms to produce relatively low molecular weight compounds, because the reaction between deactivator compounds and the metal is apparently one in which two molecules of deactivator are capable oi capturing and deactivating not more than one atom of the metal. It is not therefore desirable to add too great an amount of dead load to the molecule of the deactivator.
  • the value of compounds as deactivator-s and suppressors of oxidation due to catalytic activity of the metals may be estimated by measuring the activities under at least two conditions, namely, before and after oxidation.
  • a gasoline one may measure first, the extent to which it overcomes the adverse eifect of the metal in lowering the induction period, second, the extent to which it reduces the initial copper dish gum value 01 the gasoline; and third, the extent to which it maintains low copper dish gum alter accelerated oxidation.
  • the deactivators of this invention suppress the catalytic activity for example of copper
  • the deactivators were tested in gasoline containing 1 part per million of dissolved
  • Table 11 the deactivation elects e1 mono salicylal beta beta mono amino hydroxy dietbyliminoetheronthecopperdishgumand tarding their eil'ectiveness.
  • the deactivator retained its ability to suppress the copper dish gum to the original low concentration even after exposure to oxidation conditions.
  • the eflect of the deactivator-s in contact with lubricating oil is illustrated by the attached drawing representing a graph wherein is plotted the length of time in hours of oxidation against the amount of oxygen absorbed in the presence 01 metallic iron.
  • Our deactivators also suppress the catalytic oxidation which may be caused by a combination of the various metal oxidation promote'rs.
  • gasoline containing dissolved copper is stored in an iron drum, our compounds deactivate both the dissolved copper and metallic iron.
  • antioxidants and other compounds in the substance to be desensitized which compounds have the property 01' modifying the susceptibility of these substances toward non-catalytic oxidation such as ordinary oxidation inhibitors as used in gasoline, lubricating oil, rubber, tats, maps, etc. may have an influence on the activity of deactivators, promoting or re-
  • this invention may be used in conjunction with other addition agents for example, in gasoline, together with anti-knock compounds and anti-oxidants or in lubricating oils together with anti-oxidants, blooming agents, anti-corrosive, extreme pressure compounds, detergents, etc., or in Diesel fuels together with knock suppressors, anti-oxidants, etc. It is, however, desirable that the addition agent shall not raise the acidity of the substance to be desensitized to the point of greatly diminishing the activity of the deactivators.
  • the metal deactivators may be added to the organic substances to be stabilized in any desired form. They may be added in solid or liquid form, mixed with other addition agents or dissolved in a solvent.
  • An organic substance subject to deterioration through oxidation which substance during its useful life comes in contact with an oxidation promoter selected .from the group consisting of metallic iron, copper, chromium, lead, cobalt and the compounds of copper, chromium, lead and cobalt, containing a small amount of a deactivator having the general formula wherein x represents an aromatic nucleus and Y represents an aliphatic radical having from 2 to 12 carbon atoms inclusive,'and containing a linkage between two carbon atoms of an element selected from the group consisting of oxygen, sulfur and nitrogen other than the nitrogen and oxygen atoms to which said if is attached.
  • An organic substance subject to deterioration through oxidation which substance during its useful life comes in contact with an oxidation promoter selected from the group consisting of metallic iron, copper, chromium, lead, cobalt and the compounds of copper, chromium, lead and cobait, containing a small amount of ortho salicylai beta beta hydroxy amino di-ethyl imino ether.
  • the substance of claim 1 which contains 4.
  • An organic substance subject to deterioration through oxidation which substance during its useful life comes in contact with an oxidation promoter selected from the group consisting of metallic iron, copper, chromium, lead, cobalt and the compounds of copper, chromium, lead and cobalt, containing a small amount of a deactivator having the general formula wherein X represents a mono-nuclear aromatic radical and Y represents an aliphatic radical having from 2 to 12 carbon atoms inclusive, and containing a linkage between two carbon atoms of an element selected from the group consisting of oxygen, sulfur and nitrogen other than the nitrogen and oxygen atoms to which said Y is attached.
  • Y represents an aliphatic radical having from 2 to 12 carbon atoms inclusive, and containing a linkage between two carbon atoms of an element selected from the group consisting of oxygen, sulfur and nitrogen other than the nitrogen and.
  • the method of increasing the stability of organic substances subject to deterioration through oxidation in contact with oxidation promoters selected from the group consisting of metallic iron, copper, chromium, lead, cobalt and the compounds of copper, chromium, lead and cobalt which comprises incorporating in said organic substance a small amount of a metallic deactivator having the general formula wherein X represents an aromatic nucleus and Y wherein x represents an aromatic nucleus and Y represents an aliphatic radical having i'rom '2 to 12 carbon atoms inclusive, and containing a linkage between two carbon atoms of an element selected from the group consisting of orwgen, sulfur and nitrogen other than thenitrogen and oxygen atoms to which said Y is attached.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Catalysts (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
US339508A 1940-06-08 1940-06-08 Metal deactivators Expired - Lifetime US2361339A (en)

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NL66835D NL66835C (en, 2012) 1940-06-08
US339508A US2361339A (en) 1940-06-08 1940-06-08 Metal deactivators

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2422566A (en) * 1944-03-27 1947-06-17 Standard Oil Co Hydrocarbon fuels
US2463836A (en) * 1945-01-17 1949-03-08 Standard Oil Co Oxidation resistant organic substances
US2558030A (en) * 1948-09-23 1951-06-26 William A Zisman Noninflammable hydraulic fluids and lubricants
US2580005A (en) * 1947-12-31 1951-12-25 Standard Oil Dev Co Extreme pressure lubricating compositions
US2580881A (en) * 1949-05-21 1952-01-01 Du Pont Stabilized petroleum products and stabilizing compositions
US2641539A (en) * 1950-04-12 1953-06-09 Universal Oil Prod Co Preventing discoloration of fuel oil
US2707705A (en) * 1953-07-03 1955-05-03 Ashland Oil Inc Light stable petrolatum
US2729992A (en) * 1952-07-19 1956-01-10 Universal Oil Prod Co Rolling of metals
US2849301A (en) * 1956-07-18 1958-08-26 Socony Mobil Oil Co Inc Fuel oil composition
US2967824A (en) * 1956-06-18 1961-01-10 Raffinage Cie Francaise Process of deodorizing hydrocarbons of petroleum
US3138571A (en) * 1960-04-05 1964-06-23 Pennsalt Chemicals Corp Antioxidants and antiozonants
US3288713A (en) * 1963-11-14 1966-11-29 Sinclair Research Inc Synthetic ester lubricants containing antioxidants
US3457053A (en) * 1965-06-14 1969-07-22 Universal Oil Prod Co Stabilization of hydrocarbon oils and novel additive therefor
US4165292A (en) * 1975-05-23 1979-08-21 Edwin Cooper And Company Limited Lubricant corrosion inhibitor
US4867890A (en) * 1979-08-13 1989-09-19 Terence Colclough Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound
US5100532A (en) * 1990-12-05 1992-03-31 Betz Laboratories, Inc. Selected hydroxy-oximes as iron deactivators
US20050103686A1 (en) * 2002-04-26 2005-05-19 Taylor Spencer E. Method and apparatus for improving the oxidative thermal stability of distillate fuel

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2422566A (en) * 1944-03-27 1947-06-17 Standard Oil Co Hydrocarbon fuels
US2463836A (en) * 1945-01-17 1949-03-08 Standard Oil Co Oxidation resistant organic substances
US2580005A (en) * 1947-12-31 1951-12-25 Standard Oil Dev Co Extreme pressure lubricating compositions
US2558030A (en) * 1948-09-23 1951-06-26 William A Zisman Noninflammable hydraulic fluids and lubricants
US2580881A (en) * 1949-05-21 1952-01-01 Du Pont Stabilized petroleum products and stabilizing compositions
US2641539A (en) * 1950-04-12 1953-06-09 Universal Oil Prod Co Preventing discoloration of fuel oil
US2729992A (en) * 1952-07-19 1956-01-10 Universal Oil Prod Co Rolling of metals
US2707705A (en) * 1953-07-03 1955-05-03 Ashland Oil Inc Light stable petrolatum
US2967824A (en) * 1956-06-18 1961-01-10 Raffinage Cie Francaise Process of deodorizing hydrocarbons of petroleum
US2849301A (en) * 1956-07-18 1958-08-26 Socony Mobil Oil Co Inc Fuel oil composition
US3138571A (en) * 1960-04-05 1964-06-23 Pennsalt Chemicals Corp Antioxidants and antiozonants
US3288713A (en) * 1963-11-14 1966-11-29 Sinclair Research Inc Synthetic ester lubricants containing antioxidants
US3457053A (en) * 1965-06-14 1969-07-22 Universal Oil Prod Co Stabilization of hydrocarbon oils and novel additive therefor
US4165292A (en) * 1975-05-23 1979-08-21 Edwin Cooper And Company Limited Lubricant corrosion inhibitor
US4867890A (en) * 1979-08-13 1989-09-19 Terence Colclough Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound
US5100532A (en) * 1990-12-05 1992-03-31 Betz Laboratories, Inc. Selected hydroxy-oximes as iron deactivators
US20050103686A1 (en) * 2002-04-26 2005-05-19 Taylor Spencer E. Method and apparatus for improving the oxidative thermal stability of distillate fuel
US20080067110A1 (en) * 2002-04-26 2008-03-20 Bp Oil International Limited Method and apparatus for improving the oxidative thermal stability of distillate fuel

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