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
  • 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
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio 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
  • 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
  • C10M2205/17—Fisher Tropsch reaction products
  • C10M2205/173—Fisher Tropsch reaction products used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
• • 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
  • C10N2030/08—Resistance to extreme temperature
• • 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
  • C10N2040/12—Gas-turbines
• • 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
  • C10N2040/12—Gas-turbines
  • C10N2040/13—Aircraft turbines

Definitions

• This invention relates to a new class of compounds which have been found to be particularly suitable for use as synthetic lubricants because of their low pour points, high viscosity indices and good load-carrying characteristics. 7
• Esters represent one class of materials which have attracted unusual interest as synthetic lubricants. In general, they are characterized by higher viscosity indices and lower pour points than mineral oils of corresponding viscosity. The esters described in the present speciflcation have been found to exhibit very low pour points, high viscosity indices, and in addition unusually good load-carrying properties. Lubricantspossessing such properties are of special.
• glycol esters of sulfur-containing monocarboxylic acids The glycols may be the paraffin glycols or they may be glycols containingoxygen'or sulfur ingether or thioether linkages. I r
• R and R. are open chain aliphatic hydrocarbon radicals containing 2 to 22 carbon atoms, 0
• R and R. may be alike or different.
• R of the formula may be a saturated aliphatic hydrocarbon group, straight chain or branched, containing 2 to 18 carbon atoms, or
• the compound may be a series of saturated aliphatic hydrocarbon radicals linked by oxygen or sulfur atoms, or by both oxygen and sulfur atoms, provided there are at least two carbon atoms between each carboxyl group and the nearest oxygen or sulfur atom and at least two carbon atoms between each oxygen or sulfur atom in the chain, and provided further that the total number of carbon and oxygen or sulfur atoms in the entire R" radical is from 5 to and that there are not more than two sulfur atoms in'the chain.
• the compound should have a molecular weight of at least 300.
• sulfur-containing acids employed in preparing the esters of the present invention may be conveniently prepared by reacting an olefin, e. g., diisobutylene, with hydrogen sulfide to form an alkyl mercaptan, after which the mercaptan is reacted with acrylonitrile to form the fl-alkylmercaptopropionitrile, and the latter is in turn hydrolyzed to form the fl-alkylmercaptopropionic acid.
• olefin e. g., diisobutylene
• the mercaptans may be formed from readily obtainable olefins and olefin polymers such as propylene, isobutylene, diisobutylene, triisobutylene, propylene polymers, and the like.
• Sulfur-containing acids may also be prepared by the reaction of halo-acids with mercaptans, by the addition of mercaptans to unsaturated acids, or by the addi tion of thioglycolic acid to olefins. It is not intended that this invention be limited to the 3- alkylmercaptopropionic acids, although they are preferred from the standpoint of ease of preparation and cost.
• Acids suitable for use in accordance with the present invention are typified by compounds such as ethylmercaptoacetic acid, 8.- methylmercaptopropionic acid, e-ethylmercapto- 3 propionic acid, ,a sec. butylmercaptopropionic acid, ,B-tert.-butylmercaptopropionic acid, c-tertoctylmercaptopropionic acid, ,8 tert.
• dodecylmercaptopropionic acid ,6 cetylmercaptopropicnic acid, s-allylmercaptopropionic acid, 'yoctylmercaptobutyric acid, Y-dodecylmercaptobutyric acid, -hexadecylmercaptobutyric acid, w-octylmercaptoundecanoic acid, w-dodecylmercaptoundecanoic acid, w-hexadecylmercaptoun- 4 dodecylmercaptopropionic acid with various glycols.
• the last two of the above-named acids were prepared as follows: To a mixture of 12 cc.
• Triton B benzyltrimethylammonium hydroxide
• a,nd 2,mols,of themercaptanlprepared by reacting diisobutylene or;;t riisobutylcne with hydrogen sulfide was added dropwise 3 mols of :acrylonitrile at such a rate as to keep the temperature below 50 C.
• dried over sodium sulof the present invention include.ethyleneglYcol fate, and the 11. 1 removed O e Steam bath. and any of the paraflinic homologues of thesame '"rhere m e'was mixed with 2.1 mols of sodium containing up to 18 carbon atoms. These may "hydroxide dissolved in 600 cc. of a 50% aqueous implucle for example ethylene glycol, propylene I ethylzalcohol.
• n 1 to120 are wateptr p, tilno ,rnore water distilled lover, especially useful.
• Glycols containing suliur after .whichit .was sodiumvvraiu atoms in thioether linka s may also be em- 49 bonate.
• sgrllatas will be-givenabelow-showing-the properties ofsseven'texamples f -;esters which illustrate .the present -tinvention,ithese estersmhaving -been preparedbyzesterifyi-ng.ethylmercaptoacetic acid, -5- tertt-aoctylmercal mpropionic f acid and la-tort.-
• thefllmstr st and load-carrying capacity of mineralzciislth esters are preferably blended in proportions ranging from 1 to by weight of the mineral oil.
• the data in the last column of the table of data show the usefulness of these compounds when blended with a mineral oil.
• the unblended mineral oil employed in these tests was capable of carrying only one or two weights on the Almen machine under similar conditions of test.
• the mineral lubricating oil base stocks which may be improved in load-carrying capacity by the addition of the new compounds of the present invention may be derived from various types of crude petroleum or may consist of distillates or blends of various kinds which have been refined by any of the conventional methods. Synthetic oils may also be used such as those obtained by the polymerization of olefins or the hydrogenation of coal or its products.
• the base oils may vary considerably in viscosity and other properties depending upon the particular uses for which they are desired.
• addition agents such as thickeners, pour depressants, antioxidants, dyes, etc.
• thickeners such as thickeners, pour depressants, antioxidants, dyes, etc.
• R and R are open chain aliphatic hydrocarbon radicals containing 2 to 22 carbon atoms, at least one of the radicals containing a sulfur atom as a thioether linkage, the sulfur atom being separated from the CO0 group by at least one carbon atom, and where R" is an organic radical selected from the group consisting of (1) saturated aliphatic hydrocarbon radicals of 2 to 18 carbon atoms and (2) radicals consisting of series of saturated aliphatic hydrocarbon radicals linked through at least one non-carbon atom of the group consisting of oxygen and sulfur, not more than two sulfur atoms being in the radical, each hydrocarbon radical so linked by a non-carbon atom containing at least two carbon atoms, the sum of the carbon atoms and said non-carbon atoms in the entire radical being from 5 to 80, and the molecular weight of the entire compound being at least 300.
• composition according to claim 1 in which R and R are fl-tertiary-octylmercaptoethyl groups and R" is a saturated hydrocarbon group.
• composition according to claim 1 in which R and R are [3-tertiary-octylmercaptoethyl groups and R" is a polyethylene glycol radical.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Lubricants (AREA)

Priority Applications (2)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (2)

Cited By (12)

Citations (6)

• 1948
  • 1948-09-24 US US51112A patent/US2601063A/en not_active Expired - Lifetime
• 1949
  • 1949-07-02 FR FR990031D patent/FR990031A/fr not_active Expired

Patent Citations (6)

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