US2522512A - Preparation of synthetic lubricant - Google Patents

Preparation of synthetic lubricant Download PDF

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Publication number
US2522512A
US2522512A US701412A US70141246A US2522512A US 2522512 A US2522512 A US 2522512A US 701412 A US701412 A US 701412A US 70141246 A US70141246 A US 70141246A US 2522512 A US2522512 A US 2522512A
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ether
unsaturated
adducts
peroxide
adduct
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Harman Denham
William E Vaughan
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Shell Development Co
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Shell Development Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • 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
    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
    • 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
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • 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 relates to novel lubricating compositions. More particularly, it pertains to the use of certain fractions of non-mineral oil base sulfur-containing compounds, especially for low temperature and/or extreme pressure lubrication.
  • the lubricant adducts of unsaturated organic compounds especially those containing olefinic linkages, with such sulfurbearing substances as hydrogen sulfide or mercaptans, may be produced in yields substantially higher than by previously known methods, by using a peroxide to catalyze the formation of the adduct.
  • the unsaturated organic compounds from which the lubricant may be prepared possess at least one unsaturated linkage between two alipliatic carbon atoms regardless of the character of the compound embracing such a linkage.
  • the unsaturated hydrocarbons such as the oleflns, which term is intended to include poly-olefins and olefin polymers, are particularly contemplated. Examples of unsaturated hydrocarbons include substituents such as alkoxy, alkenoxy, aryloxy, alkaryloxy, aralkyloxy, alkylimido, etc.
  • methylacrylate methyl-methacrylate
  • divinyl ether diallyl ether
  • dimethallyl ether dimethallyl ether
  • the lubricants prepared according to the present invention are especially versatile if the unsaturated compound has terminal aliphatic unsaturated linkages.
  • the unsaturated ethers such as diallyl ether and divinyl ether meet this latter requirement and are a. preferred class of substances useful in the preparation of the lubricants of the present invention.
  • One group of such unsaturated ethers comprises the aliphatic oxyethers in which only one of the aliphatic radicals attached to the ether oxygen atom contains an unsaturated linkage.
  • ethers examples include ethyl vinyl ether, ethyl propenyl ether, methyl isopropenyl ether, ethyl isopropenyl ether, methyl allyl ether, ethyl allyl ether, n-propyl allyl ether, isopropyl allyl ether, 4-ethoxybutene-l, G-ethoXy-hexene-I, gamma-ethoxyalpha-butylene, methyl propargyl ether, ethyl propargyl ether, etc., and their homologs and analogs.
  • the above unsaturated ethers and their homologs may be substituted by straight-chain, cyclic and/or heterocyclic radicals, as well as by as halogens.
  • bon atoms include divinyl sulfide, .chlorovinyl) thioether, diallyl sulfide, dicrotyl
  • suitable unsaturated ethers which may be employed as a startingmaterial in one oi' the radicals attached to the thioether sul-- fur atom contains an unsaturated linkage. Examples of this group are ethyl vinyl sulfide, ethyl isopropenyl sulfide, and the like.
  • Suitable lubricants may be prepared from the above types of unsaturated ethers, it is preferred that both radicals attached to the ether oxygen or thioether sulfur groups contain unsaturated (preferably olefinic) linkages, since'the adducts formed therefrom usually contain a relatively large fraction having superior lubricating properties.
  • poly-unsaturated ethers divinyl ether, diisopropenyl ether, diallyl ether, dicrotyl ether, dimethallyl ether, di(alpha-methyl-allyl) ether, (butene-1-yl-3) (butene-2-yl-4) ether, dihexenyl ethers, allyl(2-methyl-pentene-1-yl-2) .ether, allyl linalyl ether, etc., as well as the haloin which each radical attached to the sulfur atom contains an unsaturated linkage between two cardi(betasulfide, dimethallyl sulfide, dihexenyl sulfides, and the like, and their homologs and analogs.
  • the ethers employed as the starting material for the preparation of the present lubricants may also contain more than one ether oxygen atom and/or thioether sulfur atom, this group of unsaturated ethers being represented by compounds of the type 'of 1,2-bis(vinyloxy) ethane, 1,3-bis- (vinyloxy) propane, 1,2-bis(allyloxy) ethane, and the like, as well as by the unsaturated disulfides,
  • lubricants may be prepared from adducts, involving a halogenated unsaturated organic compound.
  • halogenated unsaturated compounds may contain one or more oleflnic linkages, preferably of olefinic character.
  • halogen i.e. chlorine, bromine, iodine land/or fluorine
  • halogenated hydrocarbons examples include: vinyl halides, allyl halides, z-halo-propylene, crotyl halides, isocrotyl halides, 4-halo-butene-1 methallyl halides, 2-halo-butene-2, monohalogenated acetylenes, propargyl halides, 1,1-dihaloethylenes, trihalo-ethylenes, 2-halo-pentene-1, 3-halo-cyclohexane, 2 halo-1,4 diphenyl butene-2,3-halo-pentadiene-l,4, and their homologs.
  • halogenated compounds may be further substituted in the nucleus and/or in the substituents in various degrees by straightchain, branched chain, carbocyclic, and/or heterocyclic radicals, and by such substitutents as alkoxy, alkenoxy, arylow, alkylimido, and the like.
  • the organic compounds of the'above class may contain two or more halogen atoms which may be attached to saturated and/or unthe present lubricants are derived are formed by reaction of one or more of the above unsaturated organic compounds with hydrogen sulfide or a Any sufliciently stable aliphatic haercaptan is suitable as a reactant for the formation of such adducts.
  • a suitable aliphatic mercaptan may contain one or more sulfhydryl groups or radicals, preferably dior polymercaptans. In the majority of cases it is preferable to employ mercaptans of primary, secondary or tertiary character, particularly those contained or derived from petroleum or petroleum products.
  • mercaptans of primary, secondary or tertiary character, particularly those contained or derived from petroleum or petroleum products. The methyl, ethyl,
  • the reaction is carried out by heating the unsaturated organic compound and hydrogen sulfide or a mercaptan in the presence of an organic peroxide, preferably in a closed vessel.
  • the peroxides preferably are organic peroxides such as the alkyl hydroperoxides, dialkyl peroxides, and alkvlperoxy hydrocarbon derivatives.
  • the alkyl hydroperoxides form a preferred group of catalysts, and of these the tertiary-alkyl hydroperoxides are the most active. These include tertiary-butyl hydroperoxide, tertiary-amyl hydroperoxide, tertiary-hexyl hydroperoxide, etc.
  • An especially preferred class of peroxides are the dialkyl peroxides, and of these, the di-tertiaryalkyl peroxides are the most satisfactory. This group is exemplified by di-tertiary-butyl peroxide, di-tertiaryamyl-peroxide, di-tert-hexyl peroxide, etc.
  • peroxides which act as catalysts include alkyl peroxy alkanes, such as 2,2-bis(tertiarY- butylperoxy) butane, as well as peroxides such as benzoyl peroxide, aeetyl peroxide, benzoyl acetyl peroxide, and lauroyl peroxide, and hydroxyalkyl peroxides, such as hydroxy methyl tertiary butyl peroxide.
  • alkyl peroxy alkanes such as 2,2-bis(tertiarY- butylperoxy) butane
  • peroxides such as benzoyl peroxide, aeetyl peroxide, benzoyl acetyl peroxide, and lauroyl peroxide
  • hydroxyalkyl peroxides such as hydroxy methyl tertiary butyl peroxide.
  • the peroxide catalyst may be used in a wide range of concentration, but preferably is present in amounts from about 1 mol per cent to about 10 mol per cent, based on the total mols of reactants present. Optimum results are obtained when the catalyst concentration is from about 2 to about 5 mol per cent.
  • the ratio of unsaturate to hydrogen sulfide or mercaptan may vary within relatively wide limits, but preferably is between 0.5 and 2 mols unsat urate to 1 mol hydrogen sulfide or mercaptan.
  • the temperature at which the reaction is conducted will depend to a certain extent on the concentration, activity and stability of the peroxide mercaptan in the presence of an organic peroxide, 7; If temperatures above C. are used when the catalyst concentration is as high as mol per cent, the reaction may become violent even to the point of explosion, However, if an active peroxide is present, even inamounts as low as about one mole per cent, the reaction will proceed at a, satisfactory rate at temperatures as low as about 40 C. It is preferable, from an economic and control standpoint, and when using about 2% mol per cent of a catalyst of the activity of di-tertiary-butyl peroxide, to maintain the temperature within the range from about 100 C. to about 140 C.
  • the time for which the adduct reaction is allowed to proceed willvary with the activity of the catalyst and the temperature being employed. Usually the reaction will be completed when the other conditions are as stated hereinbefore, in from about 1 to about 48 hours, and close control of the reaction is obtained when conditions are such that the reaction time is from about 2 toabout 10 hours.
  • Diluents may or may not be used, as desired. While they are not essential, their use at times may be preferable in order to reduce the viscosity of the reaction mixture, to act as a mutual solvent i'or the reactants and catalyst, or to reduce the concentration of the reactants, thus allow- 8 close control oLthe course of the reaction.
  • the diluent is substantially inert with respect to the reactants or catalysts.
  • ra active diluents may be used for the purpose of initiating or terminating polymer chains, sons to give adducts having modified propertiesfa's, more particularly pointed out hereinafter, v,
  • the reaction proceeds at its optimum rate when retardants such as hydroquinor'ie,Lpiperi-w dine, and certain metal salts are absent.
  • the product is further treated to eliminate that fraction of the product which is too volatile, or other- I wise unsuitable, for use as a lubricant.
  • Thistreatment may vary with ,-the product and the type of lubricant desired, but usually comprises selective solvent extraction for the removal of catalyst and undesirable fractions, or partial distillation, usually under diminished pressure, or a combination of these two steps.
  • An essential feature a of" the I present invention is the substantially complete removal "of the volatile components ofthe adduct. Since the adduct reaction usually results in the formation of a mixture of products of continuously varying molecular weight, this relatively volatile fraction will vary in'amount,dependentupon'the conditions under which the adduct is;formed. The sensitizer employed and" its amount will havea great effectupon the prjportion "of relatively volatile components in the "product.
  • the lubricant so obtained may be further treated in order to improve color, alter terminal" groups, etc, if desired.
  • -th polymer when the adduct is formed from hydrogen sulfide and an oxyether having unsaturated linkages inbothradicals attached to the ether oxygen atom; -th polymer has the general formula e or, different dijoriunsubstitutedihydrocar ntradicals, mv is an integer,.
  • th'e polymer corresponds" to that above, except that the oxygen'ato'm's are' all replacedby sulfur. atoms, wthus'g; giving, a. I polymer having a high sulfur, content; especially useful for extreme pressure, lubrication. 2,: An out-v standing member of this groupis the adduct of diallylsulfide and hydrogen sulfide.
  • the adducts so formed are. stable to oxidation in anti-oxidants; Such;
  • EXAIMPLE V.-THERMAL STABILITY OF THE HaS-DIALLYL EI'HER ADDUCT The adduct prepared as described in Emmple I was heated for 24 hours at 150 C. in a carbon dioxide atmosphere in order to determine what changes occur in its properties in the absence of oxidizing influences.
  • Table 3 presents the data 5
  • EXAMPLE ill-OXIDATION STABILITY OF HaS-DIALLYL ETHER ADDUCT Seventy-five grams of the adduct of diallyl ether and hydrogen sulfide, prepared as described in Example I were heated at 140 C. in the presence of 1 sq. cm. copper per gram oil under an initial oxygen pressure of 50 p. s. i. It ree quired 11.5 hours heating under these conditions for the oxygen pressure to drop 10 p. s. 1., and 26 hours for the pressure to drop 20 p. s. 1.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
US701412A 1946-10-05 1946-10-05 Preparation of synthetic lubricant Expired - Lifetime US2522512A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2799657A (en) * 1954-09-16 1957-07-16 Texas Co Lubricating oil additives
US2865965A (en) * 1957-02-26 1958-12-23 American Oil Co Chemical process
US3025327A (en) * 1959-03-30 1962-03-13 Standard Oil Co Mercapto-7, 3alpha, 4, 7, 7alpha-pentahydro-4, 7-methanoindenes
US3051695A (en) * 1959-10-12 1962-08-28 Phillips Petroleum Co Production of polymeric mercaptans
US3248403A (en) * 1962-03-27 1966-04-26 Du Pont Alpha, omega-bifunctional polythiomethylene compounds
US3322669A (en) * 1965-02-03 1967-05-30 Chevron Res Sulfur substituents of propene/butene copolymers as v.i. improvers
US5185090A (en) * 1988-06-24 1993-02-09 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing same
US5242612A (en) * 1988-06-24 1993-09-07 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions
US5314633A (en) * 1988-06-24 1994-05-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions and process for preparing same
US5326487A (en) * 1988-06-24 1994-07-05 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions
US5534170A (en) * 1988-06-24 1996-07-09 Exxon Chemical Patents Inc. Mixed phosphorus- and sulfur-containing reaction products useful in power transmitting compositions
US5741884A (en) * 1994-01-11 1998-04-21 Arco Chemical Technology, L.P. Process for making poly(thioether ether)s from diallyl ether and dithiols
WO2020058880A1 (en) 2018-09-19 2020-03-26 3M Innovative Properties Company Composition including a polythiol, an unsaturated compound, and a filler and a two-part composition made therefrom
USRE48464E1 (en) 2012-06-08 2021-03-16 Celanese Sales Germany Gmbh Process for producing acesulfame potassium

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE926680C (de) * 1952-08-25 1955-04-21 Huels Chemische Werke Ag Zusaetze fuer Schmiermittel

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2197781A (en) * 1937-12-03 1940-04-23 Socony Vacuum Oil Co Inc Extreme pressure lubricant
US2319183A (en) * 1940-01-16 1943-05-11 Socony Vacuum Oil Co Inc Perchloromethyl mercaptan reaction product
US2352435A (en) * 1939-06-29 1944-06-27 Shell Dev Organic sulphur compound and a process for its preparation
US2373343A (en) * 1941-05-31 1945-04-10 Hercules Powder Co Ltd Terpene derivatives
US2392295A (en) * 1941-06-28 1946-01-01 Shell Dev Photochemical production of halogenated thio-ethers

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2197781A (en) * 1937-12-03 1940-04-23 Socony Vacuum Oil Co Inc Extreme pressure lubricant
US2352435A (en) * 1939-06-29 1944-06-27 Shell Dev Organic sulphur compound and a process for its preparation
US2319183A (en) * 1940-01-16 1943-05-11 Socony Vacuum Oil Co Inc Perchloromethyl mercaptan reaction product
US2373343A (en) * 1941-05-31 1945-04-10 Hercules Powder Co Ltd Terpene derivatives
US2392295A (en) * 1941-06-28 1946-01-01 Shell Dev Photochemical production of halogenated thio-ethers

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2799657A (en) * 1954-09-16 1957-07-16 Texas Co Lubricating oil additives
US2865965A (en) * 1957-02-26 1958-12-23 American Oil Co Chemical process
US3025327A (en) * 1959-03-30 1962-03-13 Standard Oil Co Mercapto-7, 3alpha, 4, 7, 7alpha-pentahydro-4, 7-methanoindenes
US3051695A (en) * 1959-10-12 1962-08-28 Phillips Petroleum Co Production of polymeric mercaptans
US3248403A (en) * 1962-03-27 1966-04-26 Du Pont Alpha, omega-bifunctional polythiomethylene compounds
US3322669A (en) * 1965-02-03 1967-05-30 Chevron Res Sulfur substituents of propene/butene copolymers as v.i. improvers
US5314633A (en) * 1988-06-24 1994-05-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions and process for preparing same
US5242612A (en) * 1988-06-24 1993-09-07 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions
US5185090A (en) * 1988-06-24 1993-02-09 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing same
US5326487A (en) * 1988-06-24 1994-07-05 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions
US5534170A (en) * 1988-06-24 1996-07-09 Exxon Chemical Patents Inc. Mixed phosphorus- and sulfur-containing reaction products useful in power transmitting compositions
EP0611818A1 (en) 1990-07-31 1994-08-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing the same
US5741884A (en) * 1994-01-11 1998-04-21 Arco Chemical Technology, L.P. Process for making poly(thioether ether)s from diallyl ether and dithiols
US5801290A (en) * 1994-01-11 1998-09-01 Arco Chemical Technology, L.P. Process for making poly(thioether ether)s from diallyl ether and dithiols
USRE48464E1 (en) 2012-06-08 2021-03-16 Celanese Sales Germany Gmbh Process for producing acesulfame potassium
WO2020058880A1 (en) 2018-09-19 2020-03-26 3M Innovative Properties Company Composition including a polythiol, an unsaturated compound, and a filler and a two-part composition made therefrom

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