US2496508A - Stabilized organic sulfur-containing compounds - Google Patents

Stabilized organic sulfur-containing compounds Download PDF

Info

Publication number
US2496508A
US2496508A US679556A US67955646A US2496508A US 2496508 A US2496508 A US 2496508A US 679556 A US679556 A US 679556A US 67955646 A US67955646 A US 67955646A US 2496508 A US2496508 A US 2496508A
Authority
US
United States
Prior art keywords
organic sulfur
hydrogen sulfide
containing compounds
organic
compounds
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 - Lifetime
Application number
US679556A
Inventor
Roger W Watson
Lawson W Mixon
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.)
Standard Oil Co
Original Assignee
Standard Oil Co
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 Standard Oil Co filed Critical Standard Oil Co
Priority to US679556A priority Critical patent/US2496508A/en
Application granted granted Critical
Publication of US2496508A publication Critical patent/US2496508A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/042—Epoxides
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated 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
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • 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
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • C10M2225/041—Hydrocarbon polymers

Definitions

  • organic compounds are sulfurized terpenes, sulfurized olefins and olefin polymers, sulfurized fatty oils of animal and vegetable origin, suliurized sperm oil, sulfurized mineral oils and the like.
  • sulfurized terpenes sulfurized olefins and olefin polymers
  • sulfurized fatty oils of animal and vegetable origin sulfurized fatty oils of animal and vegetable origin
  • suliurized sperm oil sulfurized mineral oils and the like.
  • lubricants such as hydrocarbon lubricating oils frequently contain sulfurized materials to impart thereto various desired properties such as extreme pressure properties, anticorrosion properties and the like.
  • organic epoxides in small but sufiicient quantities to substantially inhibit the evolution of hydrogen sulfide; suitabLv in concentrations of from about 0.001% to about 5.0% and preferably from about 0.01% to about 3;0% by weight based upon the sulfur-containing compound.
  • organic epoxide as used herein and in the appended Ethylene oxide claims means a compound containing an olefin oxide group such as the structural grouping
  • Chloroprene oxide Isoprene oxide Decene oxide Styrene oxide Cyclohexylene oxide Cyclopentene oxide Pinene oxide Epichlorohydrin Glycide Propylene oxide 2,3-epoxybutane 1,2-epoxybutane Isobutylene oxide Butadiene oxide and epoxide compounds formed by the oxidation of hydrocarbons, especially olefinic hydrocarbons.
  • the effectiveness of organic epoxides of the type described herein in inhibiting the evolution of hydrogen sulfide from organic sulfur-containing compounds is illustrated by the data in the following table. These data were obtained by placing the control or the control and the various inhibitors in a container and maintaining the same at the desired temperature, namely 250 F. or 200 F., while passing nitrogen therethrough at a rate of one liter per hour. After one-half hour to remove preformed hydrogen sulfide, the exit tube from the container was connected to a flask of lead acetate solution. The rate of hydrogen sulfide evolved was determined by the amount of lead sulfide formed.
  • the control was a mineral lubricating oil additive composition containing a sulfurized mineral oil, a sulfurized terpene, and a KOH neutralized reaction product of Past and an isobutylene polymer.
  • the above tabulated data show the effectiveness of organic epoxides in inhibiting hydrogen sulfide evolution from organic sulfur-containing compounds. While these data were obtained with aaoaeoe a specific lubricant composition using a particular oil-soluble detergent, namely the KOH neutralized reaction product of P285 and an isobutylene polymer, and particular organic sulfur-containing compounds, namely a sulfurized mineral oil and a sulfurlzed terpene, other oil-soluble detergenttype additives and other organic sulfur-containing materials can be used.
  • the oilsoluble detergent may be a neutralized reaction product of a phosphorous sulfide and a hydro-- carbon as described in U. S. 2,316,082,
  • lubricant compositions contain from about 0.001% to about by weight of an oilsoluble detergent-type additive and an organic sulfur-containing additive, the former to impart varnish inhibiting or removing properties to the lubricant, and the latter to impart lubrieating and/or corrosion inhibiting properties.
  • the oil-soluble detergent-type additive is frequently responsible for an increased rate of hydrogen sulfide evolution from the organic sulfurcontaining additive. Under these conditions the addition of the herein-disclosed epoxides effectively inhibitsthe evolution of hydrogen sulfide from such compositions.
  • oil-soluble detergent-type additive means an organic compound having the property of substantially inhibiting the formation of varnish in internal combustion engines and/or the property of removing varnish formed in such engines.
  • a sultm'ized oleaginous compound which normally evolves hydrogen sulfide on storage 40 2.
  • a lubricant composition consisting essentially or a. major proportion of a hydrocarbon 011,
  • an organic sulfur-containing compound which evolves hydrogen sulfide which evolves hydrogen sulfide, and from about 0.001% to about 5%, by weight, based on the sulfur-containing compound, of an aliphatic epoxide.
  • a lubricant composition consisting essentially of a major proportion of a hydrocarbon oil, an organic sulfur-containing compound which normally evolves hydrogen" sulfide, an oil-soluble phosphorusand sulfur-containing detergent type additive, and from about 0.001% to about 5%, by weight, based on the sulfur-containing compound, of an aliphatic epoxide.

Description

Patented Feb. 7, 1950 UNITED STATES PATENT OFFICE STABILIZED ORGANIC SULFUR-CONTAIN- 4 ING COMPOUNDS Roger W. Watson, Chicago, Ill., and Lawson W. Mixon, Hammond, Ind., assignors to Standard Oil Company, Chicago, Ill., a corporation of Indiana No Drawing. Application June 26, 1946, Serial No. 679,556
6 Claims. (Cl. 25248.2)
- hydrogen sulfide from such organic compounds is very objectionable. Examples of such organic compounds are sulfurized terpenes, sulfurized olefins and olefin polymers, sulfurized fatty oils of animal and vegetable origin, suliurized sperm oil, sulfurized mineral oils and the like. Not only is the use of such organic compounds restricted because of the obnoxious odor of the evolved hydrogen sulfide, but the use of compounds containing various amounts of such organic sulfur compounds is often restricted because of this nuisance. For example, lubricants such as hydrocarbon lubricating oils frequently contain sulfurized materials to impart thereto various desired properties such as extreme pressure properties, anticorrosion properties and the like. However, such lubricants in storage or during service evolve hydrogen sulfide which is considered to be highly objectionable by the users of such lubricants. It is, therefore, an object of the present invention to provide an improved method of inhibiting the evolution of hydrogen sulfide from organic sulfur-containing compounds which normally evolve hydrogen sulfide durin service or storage. Another object of the present invention is to provide a method whereby-organic sulfur-containing compounds which evolve obnoxious hydrogen sulfide odors are rendered inofiensive. Another object of the invention is to provide organic sulfur-containing compounds stabilized against hydrogen sulfide evolution. Other objects and advantages of the invention will become apparent from the following description thereof.
We have discovered that the evolution of hydrogen sulfide from organic sulfur-containing compounds can be substantially inhibited by adding to such sulfur-containing compounds, organic epoxides in small but sufiicient quantities to substantially inhibit the evolution of hydrogen sulfide; suitabLv in concentrations of from about 0.001% to about 5.0% and preferably from about 0.01% to about 3;0% by weight based upon the sulfur-containing compound. The term organic epoxide as used herein and in the appended Ethylene oxide claims means a compound containing an olefin oxide group such as the structural grouping The following specific compounds are representative of the classes named above:
Chloroprene oxide Isoprene oxide Decene oxide Styrene oxide Cyclohexylene oxide Cyclopentene oxide Pinene oxide Epichlorohydrin Glycide Propylene oxide 2,3-epoxybutane 1,2-epoxybutane Isobutylene oxide Butadiene oxide and epoxide compounds formed by the oxidation of hydrocarbons, especially olefinic hydrocarbons.
While the foregoing compounds are all effective in inhibiting the evolution of hydrogen sulfide from organic sulfur-containing compounds, it is not to be implied that all are equivalents, since the specific activity of the various epoxides varies to some extent.
The effectiveness of organic epoxides of the type described herein in inhibiting the evolution of hydrogen sulfide from organic sulfur-containing compounds is illustrated by the data in the following table. These data were obtained by placing the control or the control and the various inhibitors in a container and maintaining the same at the desired temperature, namely 250 F. or 200 F., while passing nitrogen therethrough at a rate of one liter per hour. After one-half hour to remove preformed hydrogen sulfide, the exit tube from the container was connected to a flask of lead acetate solution. The rate of hydrogen sulfide evolved was determined by the amount of lead sulfide formed. The control was a mineral lubricating oil additive composition containing a sulfurized mineral oil, a sulfurized terpene, and a KOH neutralized reaction product of Past and an isobutylene polymer.
The above tabulated data show the effectiveness of organic epoxides in inhibiting hydrogen sulfide evolution from organic sulfur-containing compounds. While these data were obtained with aaoaeoe a specific lubricant composition using a particular oil-soluble detergent, namely the KOH neutralized reaction product of P285 and an isobutylene polymer, and particular organic sulfur-containing compounds, namely a sulfurized mineral oil and a sulfurlzed terpene, other oil-soluble detergenttype additives and other organic sulfur-containing materials can be used. For example, the oilsoluble detergent may be a neutralized reaction product of a phosphorous sulfide and a hydro-- carbon as described in U. S. 2,316,082,
Many lubricant compositions contain from about 0.001% to about by weight of an oilsoluble detergent-type additive and an organic sulfur-containing additive, the former to impart varnish inhibiting or removing properties to the lubricant, and the latter to impart lubrieating and/or corrosion inhibiting properties. The oil-soluble detergent-type additive is frequently responsible for an increased rate of hydrogen sulfide evolution from the organic sulfurcontaining additive. Under these conditions the addition of the herein-disclosed epoxides effectively inhibitsthe evolution of hydrogen sulfide from such compositions.
The term oil-soluble detergent-type additive" as used herein and in the appended claims means an organic compound having the property of substantially inhibiting the formation of varnish in internal combustion engines and/or the property of removing varnish formed in such engines.
While we have described our invention by reference to specific embodiments thereof, these have been by way oi illustration and the invention is not to be limited thereby, but includes within its scope such modifications as come within the spirit and scope of the appended claims.
We claim:
1. A sultm'ized oleaginous compound which normally evolves hydrogen sulfide on storage 40 2. A composition as described in claim 1 in which the epoxide is epichlorohydrin.
3. A lubricant composition consisting essentially or a. major proportion of a hydrocarbon 011,
an organic sulfur-containing compound which evolves hydrogen sulfide, and from about 0.001% to about 5%, by weight, based on the sulfur-containing compound, of an aliphatic epoxide.
4. A lubricant composition as described in claim 3 in which the aliphatic epoxide is epichlorohydrin.
5. A lubricant composition consisting essentially of a major proportion of a hydrocarbon oil, an organic sulfur-containing compound which normally evolves hydrogen" sulfide, an oil-soluble phosphorusand sulfur-containing detergent type additive, and from about 0.001% to about 5%, by weight, based on the sulfur-containing compound, of an aliphatic epoxide.
6. A lubricant compositilm as described in claim 5, in which the oil-soluble detergent-type additiveis a neutralized reaction product of a phosphorous sulfide and a hydrocarbon.
ROGER W. WATSON. LAWSON W. MIXON.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS 2,249,340 Wilson et al. July 15, 1941

Claims (1)

1. A SULFURIZED OLEAGINOUS COMPOUND WHICH NORMALLY EVOLVES HYDROGEN SULFIDE ON STORAGE CONTAINING IN COMBINATION THEREWITH FROM ABOUT 0.001% TO ABOUT 5%, BY WEIGHT, BASED ON THE SULFURIZED COMPOUND, OF AN ALIPHATIC EPOXIDE.
US679556A 1946-06-26 1946-06-26 Stabilized organic sulfur-containing compounds Expired - Lifetime US2496508A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US679556A US2496508A (en) 1946-06-26 1946-06-26 Stabilized organic sulfur-containing compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US679556A US2496508A (en) 1946-06-26 1946-06-26 Stabilized organic sulfur-containing compounds

Publications (1)

Publication Number Publication Date
US2496508A true US2496508A (en) 1950-02-07

Family

ID=24727392

Family Applications (1)

Application Number Title Priority Date Filing Date
US679556A Expired - Lifetime US2496508A (en) 1946-06-26 1946-06-26 Stabilized organic sulfur-containing compounds

Country Status (1)

Country Link
US (1) US2496508A (en)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2637722A (en) * 1950-05-31 1953-05-05 Standard Oil Co Lubricant and method of making same
US2662856A (en) * 1951-01-11 1953-12-15 Tide Water Associated Oil Comp Mineral oil compositions
US2684943A (en) * 1950-11-01 1954-07-27 Continental Oil Co Lubricants
US2744068A (en) * 1952-07-29 1956-05-01 Standard Oil Co Odor stabilized lubricating oil additives
US2786829A (en) * 1952-09-12 1957-03-26 Gulf Research Development Co Sulfurization in the presence of sulfur dioxide
US2948669A (en) * 1960-08-09 Production of superior neutral oils
US2992184A (en) * 1957-11-19 1961-07-11 Exxon Standard Sa Lubricant compositions
US3001980A (en) * 1956-08-04 1961-09-26 Exxon Standard Sa Lubricating oils
US3182021A (en) * 1955-01-27 1965-05-04 Lubrizol Corp Lubricants containing phosphorus thioic derivatives
US3190833A (en) * 1961-04-14 1965-06-22 Lubrizol Corp Oxidation-resistant lubricating composition
US3210280A (en) * 1961-03-22 1965-10-05 Fmc Corp Chlorinated sulfurized esters
US3213023A (en) * 1963-03-11 1965-10-19 Lubrizol Corp Lubricants containing metal phosphorodithioate-haloepoxide reaction products
US3294499A (en) * 1962-02-07 1966-12-27 Shell Oil Co Stabilized hydrocarbon compositions
US3316237A (en) * 1963-01-21 1967-04-25 Snam Spa Additive for cutting-oils and for high-pressure oils
US3425814A (en) * 1963-05-03 1969-02-04 Exxon Research Engineering Co Stabilized oil
US3974297A (en) * 1974-07-19 1976-08-10 Monsanto Company Packaging resins
US5218147A (en) * 1992-02-10 1993-06-08 Phillips Petroleum Company Stable polysulfides and process therefor
US5858208A (en) * 1994-08-04 1999-01-12 Baker Hughes Incorporated Methods for improving conversion in fluidized catalytic cracking units
WO2001070679A1 (en) * 2000-03-21 2001-09-27 The Lubrizol Corporation H2s scavengers for polysulfide products and methods for scavenging h2s from polysulfide products

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1840269A (en) * 1930-03-18 1932-01-05 Lawrence L Reeves Method of refining distillates
US2166604A (en) * 1932-04-22 1939-07-18 Ig Farbenindustrie Ag Stable compositions comprising chlorinated substances
US2205021A (en) * 1934-11-02 1940-06-18 Ig Farbenindustrie Ag Production of condensation products
US2249340A (en) * 1938-12-03 1941-07-15 Standard Oil Dev Co Method of decreasing metal corrosion

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1840269A (en) * 1930-03-18 1932-01-05 Lawrence L Reeves Method of refining distillates
US2166604A (en) * 1932-04-22 1939-07-18 Ig Farbenindustrie Ag Stable compositions comprising chlorinated substances
US2205021A (en) * 1934-11-02 1940-06-18 Ig Farbenindustrie Ag Production of condensation products
US2249340A (en) * 1938-12-03 1941-07-15 Standard Oil Dev Co Method of decreasing metal corrosion

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2948669A (en) * 1960-08-09 Production of superior neutral oils
US2637722A (en) * 1950-05-31 1953-05-05 Standard Oil Co Lubricant and method of making same
US2684943A (en) * 1950-11-01 1954-07-27 Continental Oil Co Lubricants
US2662856A (en) * 1951-01-11 1953-12-15 Tide Water Associated Oil Comp Mineral oil compositions
US2744068A (en) * 1952-07-29 1956-05-01 Standard Oil Co Odor stabilized lubricating oil additives
US2786829A (en) * 1952-09-12 1957-03-26 Gulf Research Development Co Sulfurization in the presence of sulfur dioxide
US3182021A (en) * 1955-01-27 1965-05-04 Lubrizol Corp Lubricants containing phosphorus thioic derivatives
US3001980A (en) * 1956-08-04 1961-09-26 Exxon Standard Sa Lubricating oils
US2992184A (en) * 1957-11-19 1961-07-11 Exxon Standard Sa Lubricant compositions
US3210280A (en) * 1961-03-22 1965-10-05 Fmc Corp Chlorinated sulfurized esters
US3190833A (en) * 1961-04-14 1965-06-22 Lubrizol Corp Oxidation-resistant lubricating composition
US3294499A (en) * 1962-02-07 1966-12-27 Shell Oil Co Stabilized hydrocarbon compositions
US3316237A (en) * 1963-01-21 1967-04-25 Snam Spa Additive for cutting-oils and for high-pressure oils
US3213023A (en) * 1963-03-11 1965-10-19 Lubrizol Corp Lubricants containing metal phosphorodithioate-haloepoxide reaction products
US3425814A (en) * 1963-05-03 1969-02-04 Exxon Research Engineering Co Stabilized oil
US3974297A (en) * 1974-07-19 1976-08-10 Monsanto Company Packaging resins
US5218147A (en) * 1992-02-10 1993-06-08 Phillips Petroleum Company Stable polysulfides and process therefor
US5858208A (en) * 1994-08-04 1999-01-12 Baker Hughes Incorporated Methods for improving conversion in fluidized catalytic cracking units
WO2001070679A1 (en) * 2000-03-21 2001-09-27 The Lubrizol Corporation H2s scavengers for polysulfide products and methods for scavenging h2s from polysulfide products

Similar Documents

Publication Publication Date Title
US2496508A (en) Stabilized organic sulfur-containing compounds
US2765289A (en) Corrosion inhibitors and compositions containing the same
US2760933A (en) Lubricants
US2409687A (en) Sulfur and metal containing compound
US2910439A (en) Corrosion inhibited compositions
US2850453A (en) Corrosion inhibited oil compositions
US2749311A (en) Corrosion inhibitors and compositions containing the same
US2712528A (en) Mineral oil composition containing an improved hydrocarbon-phosphorus sulfide reaction product
US2764547A (en) Corrosion resistant lubricant composition
US3583915A (en) Load carrying additives
US2459717A (en) Organic lubricant composition
US2768999A (en) Phosphosulfurized hydrocarbons and production thereof
US2761845A (en) Foam inhibition of oils
US2636858A (en) Mineral oil additive
US2439610A (en) Stabilized organic composition
US2250545A (en) Lubricating composition
US2351657A (en) Lubricant
US2497097A (en) Method of preparing stabilized organic sulfur-containing compounds
US2799651A (en) Corrosion inhibitors and compositions containing the same
US3024193A (en) Stabilized metal-working lubricant
US2799652A (en) Corrosion resistant composition
US2419325A (en) Lubricating composition
US2684943A (en) Lubricants
US2524563A (en) Lubricant
US2703318A (en) Stabilized sulfur-containing additives for lubricants