US2250545A - Lubricating composition - Google Patents

Lubricating composition Download PDF

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Publication number
US2250545A
US2250545A US235778A US23577838A US2250545A US 2250545 A US2250545 A US 2250545A US 235778 A US235778 A US 235778A US 23577838 A US23577838 A US 23577838A US 2250545 A US2250545 A US 2250545A
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US
United States
Prior art keywords
xanthogen
oil
oils
lubricating
sulfur
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
US235778A
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English (en)
Inventor
Louis A Mikeska
Lieber Eugene
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 Development Co
Original Assignee
Standard Oil Development Co
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Filing date
Publication date
Priority to NL51053D priority Critical patent/NL51053C/xx
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to US235778A priority patent/US2250545A/en
Priority to GB13059/39A priority patent/GB522189A/en
Priority to FR855166D priority patent/FR855166A/fr
Priority to DEST59124D priority patent/DE710095C/de
Application granted granted Critical
Publication of US2250545A publication Critical patent/US2250545A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/17—Fisher Tropsch reaction products
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/16—Naphthenic acids
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/20—Rosin acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/082—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type monocarboxylic
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
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    • C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
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    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • 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
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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    • 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
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/245—Soft metals, e.g. aluminum
    • 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
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • 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
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • This invention deals with lubricating composl-1 tions. More specifically, it relates to the use in such compositions of small amounts of soluble organic xanthogen tetrasulfldes which are believed to possess a structure corresponding to the following formula:
  • Rand R represent alkyl, cyclic, or-cycloalkyl organic groups.
  • Potassium hydroxide is dissolved in absolute a1coho1'(fair excess over that required for reaction) and the required amount of carbon disulflde is added with cooling and mechanical agitation. Potassium xanthate precipitates out. The amount of xanthate is further increased by the addition of ether. excess alcohol being saturated with xanthate could be used again, avoiding the use of ether as a precipitant.) The solid product is recovered by filtration and dried.
  • the potassium xanthate is suspended in benzene (other inert solvents such as light naphtha could be used), stirred and a benzene solution of sulfur monochloride added with cooling. After the sulfur chloride has been added, the reaction mixture is refluxed for 2 hours to complete the condensation, and then poured into water. The benzene layer is removed and dried. After stripping off the benzene, the xanthogen tetrasulflde remains as a residue.
  • benzene other inert solvents such as light naphtha could be used
  • 'I'hese compounds are also compatible with soap, fatty oils and other ingredients normally employed in soluble oils, cutting oils, greases, motor oils, compounded, and industrial lubricants, without causing precipitation. or settling out of sulfur or sulfur compounds.
  • the xanthogen tetrasulfides e. g. ethyl xanthogen tetrasulflde
  • 3% of this material will carry the full load (580 lbs.) on the S. A. E. machine at 1000 R. P. M., and in addition, it meets the requirements of the Packard Stability Test.
  • This test involves the heating of the blend in an oven at 200 F. for 64 hrs. and running the thus-treated oil on the S. A. E. machine at 1000 R. P. M. and 83.6 lbs/sec. loading rate, the rubbing ratio being 14.6:1.
  • the blend must carry a full load of 550 lbs. scale pull.
  • Blends containing these xanthogen tetrasulxanthate salt prior to condensation Since these products pick up some of the mercaptan odor which is dimcult to remove, they are not as desirable as the corresponding alcohol derivatives.
  • compositions which are the subject of this invention are in the field of cutting oils.
  • a high E. P. eflect is desired without any detrimental odor or discoloration oi! the base stock, so as to give clean work pieces without need for further handling or processing.
  • Soluble cut ting oils are prepared by the addition of emulsihere such as sodium naphthenate, mahogany 1 in which the tetrasuliide is an alkyl xanthogen tetrasulilde.
  • a cutting oil comprising a mineral lubricating oil and about 2 to% oia soluble xanthogen tetrasulfide having the probable structure:
  • R and R are alkyl, cyclic or cyclo-alkyl groups, and the oxygen atoms may be replaced by sulfur.
  • the lubricating oil base stocks are generally crude or refined mineral oils of about 70 viscosity at 100 F. (Saybolt) to about 5000 viscosity at 100 F.
  • compositions may be employed i conjunction with linear polymer V.
  • linear polymer V. I. improvers, pour inhibitors, dyes, resins, voltolized'iats and/ or mineral oils or waxes, ester and other oiliness agents, phenolic or amino oxidation inhibitors, soaps, such as calcium stearate, lead oleate, lead naphthenate, aluminum naphthenate, and the like, dyes, halogenated compounds, such aschlorinated esters, chlorinated parailin waxes, etc., wetting agents, insecticides, germicides, fungicides, and the like.
  • composition of matter comprising any oil selected from the group consisting oi mineral oils and fatty oils, and a small amount of organic xanthogen tetrasulfide.
  • a lubricating composition comprising a lubricating oil base stock and at least about .01% of a soluble xanthogen sulfide having the general formula:
  • n-x-ti-(s)l-ii-x a where R and R are like or unlike alkyl, cyclic hydrocarbon, or mixed cyclo-alkyl radicals,'and X is either oxygen or sulfur.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US235778A 1938-10-19 1938-10-19 Lubricating composition Expired - Lifetime US2250545A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL51053D NL51053C (cs) 1938-10-19
US235778A US2250545A (en) 1938-10-19 1938-10-19 Lubricating composition
GB13059/39A GB522189A (en) 1938-10-19 1939-05-02 Improved lubricating compositions
FR855166D FR855166A (fr) 1938-10-19 1939-05-23 Produit lubrifiant
DEST59124D DE710095C (de) 1938-10-19 1939-09-27 Mineralschmieroele

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US235778A US2250545A (en) 1938-10-19 1938-10-19 Lubricating composition

Publications (1)

Publication Number Publication Date
US2250545A true US2250545A (en) 1941-07-29

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Application Number Title Priority Date Filing Date
US235778A Expired - Lifetime US2250545A (en) 1938-10-19 1938-10-19 Lubricating composition

Country Status (5)

Country Link
US (1) US2250545A (cs)
DE (1) DE710095C (cs)
FR (1) FR855166A (cs)
GB (1) GB522189A (cs)
NL (1) NL51053C (cs)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2431010A (en) * 1941-07-19 1947-11-18 Standard Oil Dev Co Soluble cutting oil
US2498863A (en) * 1945-08-30 1950-02-28 Socony Vacuum Oil Co Inc Lubricating oil composition
US2574457A (en) * 1947-08-05 1951-11-13 Phillips Petroleum Co Manufacture of alkyl sulfenyl trithiocarbonates
US2615804A (en) * 1947-05-08 1952-10-28 Goodrich Co B F Herbicidal composition
US2615802A (en) * 1948-10-23 1952-10-28 Monsanto Chemicals Herbicidal composition and method
US2743209A (en) * 1952-12-24 1956-04-24 Robert H Jones Xanthyl and trithiocarbonyl, sulfides, sulfoxides, and sulfones as pesticides
US2743210A (en) * 1952-12-24 1956-04-24 Stauffer Chemical Co Xanthogen and dtthiocarbonyl tetrasulfides as pesticides
US2813890A (en) * 1954-10-15 1957-11-19 Exxon Research Engineering Co Manufacture of alkyl xanthogen sulfides
US2925386A (en) * 1952-08-25 1960-02-16 Huels Chemische Werke Ag Mineral oil base lubricant
US3864374A (en) * 1973-11-19 1975-02-04 Canadian Ind Manufacture of alkali metal xanthates
CN116926558A (zh) * 2023-07-24 2023-10-24 湖南新文锋智能装备有限公司 一种氧醚基黄原酸酯类金属缓蚀剂及其制备方法与应用

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2431010A (en) * 1941-07-19 1947-11-18 Standard Oil Dev Co Soluble cutting oil
US2498863A (en) * 1945-08-30 1950-02-28 Socony Vacuum Oil Co Inc Lubricating oil composition
US2615804A (en) * 1947-05-08 1952-10-28 Goodrich Co B F Herbicidal composition
US2574457A (en) * 1947-08-05 1951-11-13 Phillips Petroleum Co Manufacture of alkyl sulfenyl trithiocarbonates
US2615802A (en) * 1948-10-23 1952-10-28 Monsanto Chemicals Herbicidal composition and method
US2925386A (en) * 1952-08-25 1960-02-16 Huels Chemische Werke Ag Mineral oil base lubricant
US2743209A (en) * 1952-12-24 1956-04-24 Robert H Jones Xanthyl and trithiocarbonyl, sulfides, sulfoxides, and sulfones as pesticides
US2743210A (en) * 1952-12-24 1956-04-24 Stauffer Chemical Co Xanthogen and dtthiocarbonyl tetrasulfides as pesticides
US2813890A (en) * 1954-10-15 1957-11-19 Exxon Research Engineering Co Manufacture of alkyl xanthogen sulfides
US3864374A (en) * 1973-11-19 1975-02-04 Canadian Ind Manufacture of alkali metal xanthates
CN116926558A (zh) * 2023-07-24 2023-10-24 湖南新文锋智能装备有限公司 一种氧醚基黄原酸酯类金属缓蚀剂及其制备方法与应用

Also Published As

Publication number Publication date
GB522189A (en) 1940-06-11
NL51053C (cs)
FR855166A (fr) 1940-05-04
DE710095C (de) 1941-09-03

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