US2680123A - Zinc salt of mixed ester thiophosphates - Google Patents

Zinc salt of mixed ester thiophosphates Download PDF

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Publication number
US2680123A
US2680123A US218281A US21828151A US2680123A US 2680123 A US2680123 A US 2680123A US 218281 A US218281 A US 218281A US 21828151 A US21828151 A US 21828151A US 2680123 A US2680123 A US 2680123A
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Prior art keywords
alcohol
alcohols
zinc
oil
molecular weight
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US218281A
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Paul K Mulvany
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California Research LLC
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California Research LLC
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Priority to NL85589D priority Critical patent/NL85589C/xx
Priority to BE510012D priority patent/BE510012A/xx
Application filed by California Research LLC filed Critical California Research LLC
Priority to US218282A priority patent/US2689220A/en
Priority to US218281A priority patent/US2680123A/en
Priority to GB5686/52A priority patent/GB716343A/en
Priority to DEC5529A priority patent/DE1097606B/de
Priority to FR1057074D priority patent/FR1057074A/fr
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
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    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
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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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention pertains to a new composition of matter prepared by reacting a mixture of two different alcohols with phosphorus pentasulfide (P285).
  • this invention pertains to the zinc salts of a reaction product containing mixed diesters of dithiophosphoric acids pre pared by reacting phosphorus pentasulfide with a mixture or" two different alcohols (one alcohol containing not more than 4 carbon atoms, and the other alcohol containing from 6 to 18 carbon atoms).
  • compositions set forth herein are useful in additives in lubricating oil compositions; particularly useful in inhibiting oxidation of lubricating oil compositions. These new compounds are remarkably efiective in increasing the useful life of a lubricating oil composition which is susceptible to oxidation.
  • zinc salts of dialkyldithiophosphoric acids inhibit oxidation of lubricating oil compositions.
  • the alkyl groups of these zinc dialkyldithiophosphates may be or" high molecular weight or low molecular weight.
  • Zinc dialkyldithiophosphates, wherein the alkyl groups are the same and each contain less thanil carbon atoms (e. g, 4 carbon atoms) are considerably less expensive than the zinc dialkyldithiophosphates containing alkyl groups which are the same and derived from higher molecular weight alcohols.
  • dialkyldithiophosphoric acids using two unlike low molecular weight alcohols as the source of the ester groups, and the zinc salts thereof.
  • a further object of this invention is to prepare relatively low cost mixed diesters of dithiophosphoric acids.
  • One of the alcohols used in the reaction contains less than 4 carbon atoms.
  • These alcohols include methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, butyl alcohol, sec-butyl alcohol and tertiary outyl alcohol.
  • this group of alcohols will hereinafter be called the R1 alcohols.
  • the other alcohol used to form the reaction product of this invention contains from 6 to 18 carbon atoms. These include the following alcohols: hexyl, methylisobutylcarbin-ol, ethylisopropropylcarbinol, heptyl, iso-heptyl, Z-ethyl amyl, octyl, iso-octyl, 3-ethyl hexyl, Z-propyl amyl, decyl, undecyl, dodecyl, hexadecyl, octadecyl, etc.
  • this group of alcohols will hereinafter be known as the R 2 alcohols.
  • R1 and R: alcohols need not be present in the reaction mixture in equal molar amounts.
  • the mole ratio of R1 aloe-- hols to R2 alcohols be from 1 to 5. It is particularly preferred to use a mole ratio of R1 alcohols to R2 alcohols from 2 to 4.
  • the reaction products of this invention are normally prepared by mixing two different alcohols, and causing the mixture of alcohols to react with phosphorus pentasulfide (PzSs) at temperatures ranging from about 120 15. to 200 F.
  • PzSs phosphorus pentasulfide
  • l moles of the desired alcohols e. g., 3 moles of methyl alcohol and 1 mole of hexyl alcohol, wherein the mole ratio of methyl alcohol to hexyl alcohol is 3
  • the zinc salts of the reaction mixtures are prepared by reacting the dialkyl dithiophosphoric acid preparation with Zinc oxide or zinc hydroxide at temperatures ranging from F. to 1'70 F.
  • the acid intermediate thus obtained was added to 130 parts by weight of a petroleum oil having a viscosity of 300 SSU at 100 F. (used as a diluent), then 122 parts by weight of zinc oxide was gradually added at 130 F. The whole mixture was then agitated for 3 hours at 130 F., after which the water of neutralization was removed with calcium sulfate.
  • the oil solution of the zinc salt had a pH of 6.? (after filtration), and contained 9.96% zinc, 9.43% phosphorus and 19.42% sulfur.
  • Example 2 --Reaction product of but'yl alcohol, methyiisobutylcarbinol and PzSs
  • a mixture of 237 parts by Weight (7'? mole percent) or" sec-butyl alcohol and 98 parts by weight (23 mole percent) of methylisobutylcarbinol and 222 parts by weight or P285 was charged to a reaction vessel and agitated at 170 F. for a period of 2 hours.
  • the reaction mixture was cooled and filtered to remove a small amount of unreacted P2S5.
  • the resulting butyl methylisobutylcarbinol dithiophosphate was a dark red green liquid having a neutralization number of 193 (mgs. KOl-l/grarn), a viscosity of 35.7 SSU at 100 F., a specific gravity of 1.04 (60/60), and contained 24.0% sulfur and 11.9% phosphorus.
  • the oil solubility of the zinc salts of this invention wherein the two different alcohols have certain mole ratios to each other is considerably greater than zinc salts having the same mole ratio of a mixture of two diester dithiophosphoric acids (wherein the ester groups in each acid are the same; that is, each acid contains only one of the ester radicals of the above mixed diester dithiophosphoric acid).
  • a 35% petroleum oil solution of a mixture of zinc di(secbutyl) dithiophosphate and zinc di- (methylisobutylcarbinol) dithiophosphate (mole ratio of 3.35) began to crystallize from solution within a period of 2 days at F.
  • the table below presents data concerning the effec 'veness oithe reaction products of this invention in reducing corrosion of metal parts due to oxidation of lubricating oils during the operation of internal combustion engines.
  • a stock Chevrolet engine was used. Instead of the normal babbitt bearings of -r in the Chevrolet engine, two of the connecting rods were modified to accommodate copper-lead bearing inserts, which were weighed before being assembled in the engine.
  • the Chevrolet engine was operated at 3150 R. P. M., the engine jacket temperature was maintained at 300 F., the crankcase oil temperature was maintained at 280 F'., and the engine was operated for a period of 38 hours before being disassembled and the bearing inserts weighed. Before weighing, the bearing inserts were carefully washed with solvents to remove the oil therefrom.
  • This reference oil was a California sovcnt-rciined parailinic base SAE 50 oil containing 0 0% weight a calcium allgyl sulfonate and 0.97% by ⁇ vei ht oi i ed aliryi-substitutcd calcium plienate Weight loss .irs.
  • zinc salts of this invention include the use as anti-oxidants in greases, antiwear agents in silicate fluids, that is, organic esters or silicic acid, e. g., ortho silicate esters such as tetraethyl silicate, tetra(nhexy1) silicate, tetra(2ethyihexyl) silicate, etc.
  • organic esters or silicic acid e. g., ortho silicate esters such as tetraethyl silicate, tetra(nhexy1) silicate, tetra(2ethyihexyl) silicate, etc.
  • the lubricating oils in which the new zinc salts of this invention may be incorporated include a wide variety of lubricating oils such as naplithenic base, parainn base, and mixed base mineral oils, other hydrocarbon lubricants, e. g., lubricating oils derived from coal products and synthetic oils, e. g., alkyiene polymers (such as polymers of propylene, butylene, etc, and mixtures thereof), alkylene oxide type polymers, dicarboxylic acid esters and liquid esters of acids of phosphorus.
  • Synthetic oils of the alkylene oxice type polymer which may be used include those exemplified by allzylene oxide polymers (e.
  • propylene oxide polymers and derivatives, including alkylene oxide polymers prepared by polymerizing alkylene oxides (e. g., propylene oxide) in the presence of water or alcohols, e. g., ethyl aicohol, and esters of alkylene oxide type polymers, e. g., acetylated propylene oxide polymers prepared by acetylating the propylene oxide polymers containing hydroxyl groups.
  • a zinc salt 0 mixed diesters of dithiophosphoric acids produced by reacting phosphorus pentasulfide with a blend of two different saturated aliphatic monohydric alcohols, one of said alcohols being a lower molecular weight alcohol and containing not more than 4 carbon atoms, the other of said alcohols being a higher molecular weight alcohol and containing from 6 to 18 carbon atoms, wherein the ratio of said lower molecular weight alcohol to said higher molecular weight alcohol has a value from 1.0 to 5.0.
  • the z nc salts of mixed diesters of dithiophosphoric acids produced by reacting phosphorus pentasulfide with a blend of two difierent saturated aliphatic monohydric alcohols at temperatures of 120 F. to 200 F., one of said alcohols being a lower molecular weight alcohol and containing not more than 4 carbon atoms, the other of said alcohols being a higher molecular weight alcohol and containing from 6 to 13 carbon atoms, the ratio of said lower molecular weight alcohol to said higher molecular weight alcohol having a value from 2 to 4.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
US218281A 1951-03-29 1951-03-29 Zinc salt of mixed ester thiophosphates Expired - Lifetime US2680123A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL85589D NL85589C (en)) 1951-03-29
BE510012D BE510012A (en)) 1951-03-29
US218282A US2689220A (en) 1951-03-29 1951-03-29 Lubricating oil compositions of mixed diester dithiophosphates
US218281A US2680123A (en) 1951-03-29 1951-03-29 Zinc salt of mixed ester thiophosphates
GB5686/52A GB716343A (en) 1951-03-29 1952-03-04 Mixed diesters of dithiophosphoric acids, zinc salts thereof and lubricating oil compositions of these zinc salts
DEC5529A DE1097606B (de) 1951-03-29 1952-03-13 Schmieroele
FR1057074D FR1057074A (fr) 1951-03-29 1952-03-14 Diesters mixtes d'acides dithiophosphoriques, leurs sels de zinc et huiles lubrifiantes contenant ces sels de zinc

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US218281A US2680123A (en) 1951-03-29 1951-03-29 Zinc salt of mixed ester thiophosphates

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US218282A Expired - Lifetime US2689220A (en) 1951-03-29 1951-03-29 Lubricating oil compositions of mixed diester dithiophosphates

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Cited By (15)

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US2838555A (en) * 1951-10-12 1958-06-10 Lubrizol Corp Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids
US2925398A (en) * 1957-02-11 1960-02-16 Monsanto Chemicals Composition comprising solid polyolefin and a hydrogenated polyphenyl
US2932614A (en) * 1958-01-07 1960-04-12 Exxon Research Engineering Co Manufacture of metal salts of dialkyl dithiophosphoric acids and concentrate in oil solution
DE1112067B (de) * 1957-04-18 1961-08-03 American Cyanamid Co Verfahren zur Herstellung von Zinksalzen gemischter Dithiophosphorsaeuredialkylester
DE1119854B (de) * 1958-01-07 1961-12-21 Exxon Research Engineering Co Verfahren zur Herstellung von Metallsalzen von O, O-Dialkyldithio-phosphorsaeuren von verbesserter Bestaendigkeit
US3341633A (en) * 1955-01-27 1967-09-12 Lubrizol Corp Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides
US4101428A (en) * 1976-02-25 1978-07-18 Chevron Research Company Composition comprising a mixture of the zinc salts of O,O-di(primary and secondary) alkyldithiophosphoric acids
EP0054804A1 (de) * 1980-12-19 1982-06-30 Bayer Ag Zinkkomplexe, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Verschleissschutz-Additive
US4377527A (en) * 1981-03-09 1983-03-22 Standard Oil Company (Indiana) Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates
US4495075A (en) * 1984-05-15 1985-01-22 Chevron Research Company Methods and compositions for preventing the precipitation of zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group
US4577037A (en) * 1984-02-10 1986-03-18 Chevron Research Methods for preventing the precipitation of mixed zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group
EP0322235A3 (en) * 1987-12-23 1990-03-28 Exxon Chemical Patents Inc. Dithiophosphates
US20050101802A1 (en) * 2003-11-06 2005-05-12 Thomson Paul M. Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties
US20100144563A1 (en) * 2008-12-09 2010-06-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
EP2287210A2 (en) 2003-01-30 2011-02-23 Chevron Oronite Company LLC Sulfurized polyisobutylene based wear and oxidation inhibitors

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US3013970A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
US3013969A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
US3013971A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
GB801151A (en) * 1955-01-27 1958-09-10 Lubrizol Corp Gear lubricant improving agents
US2837549A (en) * 1955-05-12 1958-06-03 American Cyanamid Co Zinc dialkyl dithiophosphates
US3000822A (en) * 1957-01-22 1961-09-19 Lubrizol Corp Phosphorodithioate inhibitors
US3074990A (en) * 1958-12-29 1963-01-22 Universal Oil Prod Co Alkylthiophosphoric acid salt of polymeric condensation product and use thereof
GB874877A (en) * 1959-01-22 1961-08-10 Exxon Research Engineering Co Metal salts of organic dithiophosphates and lubricating compositions containing them
US3112271A (en) * 1959-04-13 1963-11-26 Shell Oil Co Liquid hydrocarbon composition
NL262417A (en)) * 1960-03-15
US3073781A (en) * 1960-07-07 1963-01-15 Standard Oil Co Demulsifiable lubricant compositions
US3318808A (en) * 1963-10-15 1967-05-09 Standard Oil Co Extreme pressure lubricants
US3293181A (en) * 1965-10-15 1966-12-20 Chevron Res Dialkyl dithiophosphates and lubricants containing them
US3511780A (en) * 1966-02-09 1970-05-12 Exxon Research Engineering Co Oil-soluble ashless dispersant-detergent-inhibitors
US3442804A (en) * 1967-01-19 1969-05-06 Lubrizol Corp Lubricating composition containing a phosphorodithioate inhibitor
US3390082A (en) * 1967-09-19 1968-06-25 Lubrizol Corp Lubricants containing metal-free dispersants and inhibitors
GB1553583A (en) * 1976-02-27 1979-09-26 Cooper & Co Ltd Edwin Preparation of zinc dihydrocarbyldithiophosphates

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US2342432A (en) * 1941-12-22 1944-02-22 Gulf Oil Corp Mineral oil lubricating composition and an improvement agent therefor and its methodof preparation
US2343213A (en) * 1942-04-10 1944-02-29 American Cyanamid Co Preparation of barium salts of dithiophosphoric acid esters
US2361746A (en) * 1943-04-12 1944-10-31 American Cyanamid Co Crankcase lubricating oil composition
US2466408A (en) * 1946-01-26 1949-04-05 American Cyanamid Co Lubricating composition
US2540084A (en) * 1947-05-14 1951-02-06 Lubrizol Corp Metallic salt of reaction product of phosphorus sulfide and alkylated cycloaliphatic alcohol
GB626251A (en) * 1947-06-30 1949-07-12 Shell Refining & Marketing Co Improvements in or relating to mineral lubricating oil compositions
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US1939951A (en) * 1929-06-26 1933-12-19 American Cyanamid Co Seed disinfection
US2252984A (en) * 1939-05-06 1941-08-19 Standard Oil Co Compounded hydrocarbon oil
US2261047A (en) * 1941-07-28 1941-10-28 Lubri Zol Corp Lubricant
US2368000A (en) * 1941-12-04 1945-01-23 American Cyanamid Co Lubricating compositions

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2838555A (en) * 1951-10-12 1958-06-10 Lubrizol Corp Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids
US3341633A (en) * 1955-01-27 1967-09-12 Lubrizol Corp Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides
US2925398A (en) * 1957-02-11 1960-02-16 Monsanto Chemicals Composition comprising solid polyolefin and a hydrogenated polyphenyl
DE1112067B (de) * 1957-04-18 1961-08-03 American Cyanamid Co Verfahren zur Herstellung von Zinksalzen gemischter Dithiophosphorsaeuredialkylester
US2932614A (en) * 1958-01-07 1960-04-12 Exxon Research Engineering Co Manufacture of metal salts of dialkyl dithiophosphoric acids and concentrate in oil solution
DE1119854B (de) * 1958-01-07 1961-12-21 Exxon Research Engineering Co Verfahren zur Herstellung von Metallsalzen von O, O-Dialkyldithio-phosphorsaeuren von verbesserter Bestaendigkeit
US4101428A (en) * 1976-02-25 1978-07-18 Chevron Research Company Composition comprising a mixture of the zinc salts of O,O-di(primary and secondary) alkyldithiophosphoric acids
EP0054804A1 (de) * 1980-12-19 1982-06-30 Bayer Ag Zinkkomplexe, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Verschleissschutz-Additive
US4377527A (en) * 1981-03-09 1983-03-22 Standard Oil Company (Indiana) Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates
US4577037A (en) * 1984-02-10 1986-03-18 Chevron Research Methods for preventing the precipitation of mixed zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group
US4495075A (en) * 1984-05-15 1985-01-22 Chevron Research Company Methods and compositions for preventing the precipitation of zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group
EP0322235A3 (en) * 1987-12-23 1990-03-28 Exxon Chemical Patents Inc. Dithiophosphates
US5013465A (en) * 1987-12-23 1991-05-07 Exxon Chemical Patents, Inc. Dithiophosphates
EP2287210A2 (en) 2003-01-30 2011-02-23 Chevron Oronite Company LLC Sulfurized polyisobutylene based wear and oxidation inhibitors
US20050101802A1 (en) * 2003-11-06 2005-05-12 Thomson Paul M. Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties
US7368596B2 (en) 2003-11-06 2008-05-06 Afton Chemical Corporation Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties
US7592490B2 (en) 2003-11-06 2009-09-22 Afton Chemical Corporation Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties
US20100144563A1 (en) * 2008-12-09 2010-06-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US8211840B2 (en) 2008-12-09 2012-07-03 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties

Also Published As

Publication number Publication date
FR1057074A (fr) 1954-03-04
NL85589C (en))
GB716343A (en) 1954-10-06
US2689220A (en) 1954-09-14
DE1097606B (de) 1961-01-19
BE510012A (en))

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