US3576846A - Sulfinyl-containing alkenylsuccinates - Google Patents

Sulfinyl-containing alkenylsuccinates Download PDF

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US3576846A
US3576846A US645869A US3576846DA US3576846A US 3576846 A US3576846 A US 3576846A US 645869 A US645869 A US 645869A US 3576846D A US3576846D A US 3576846DA US 3576846 A US3576846 A US 3576846A
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radical
carbon atoms
oil
sulfinyl
anhydride
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Norman A Leister
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • 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—Semi-solids; greasy

Definitions

  • novel sulfinyl compounds are prepared by reacting 1) an alkenylsuccinic anhydride, an alkenylsuccinic acid or an alkenylsuccinamic acid and (2) at least one sulfinyl-containing hydroxy compound having the formulas:
  • y is an integer from 1 to about 50 or more and n is an integer from 1 to 40,
  • R is selected from the group consisting of (a) an alkyl radical containing from 1 to 24 carbon atoms, (b) an aryl radical (c) an aralkyl radical wherein the alkyl portion of the radical contains from 1 to 4 carbon atoms and (d) an alkaryl radical wherein the alkyl portion contains from 1 to 24 carbon atoms,
  • R is an alkylene radical having 2 to carbon atoms
  • R and R are alkylene radicals having 2 to 5 carbon atoms, a phenylene; radical or a (C -C alkyl substituted phenylene radical with the proviso that n is 1 when R and R are phenylene or (C -C alkyl substituted phenylene.
  • the combustion products of the fuel may cause excessive wear, especially when the engine is operating under relatively cold conditions which results in an accumulation of moisture and acid products on the engine surfaces. This accumulation promotes wear on various engine parts.
  • novel compounds of this invention are prepared by reacting an alkenylsuccinic anhydride, alkenylsuccinic DETAILED DESCRIPTION OF THE INVENTION
  • novel sulfinyl-containing alkenylsuccinates are prepared by reacting 1) an alkenylsuccinic anhydride, an alkenylsuccinic acid or an alkenylsuccinamic acid and (2) a: least one sulfinyl-containing hydroxy compound of the following formulas:
  • y is an integer from 1 to about 50 or more and n is an integer from 1 to 40 or more and preferably from 1 to 10,
  • R is selected from the group consisting of (a) an alkyl hydrocarbon radical containing from 1 to 24 carbon atoms, (b) an aryl hydrocarbon radical (c) an aralkyl hydrocarbon radical wherein the alkyl portion of the radical contains from 1 to 4 carbon atoms and (d) an alkaryl hydrocarbon radical wherein the alkyl portion contains from 1 to 24 carbon atoms.
  • R is an alkylene radical having 2 to 5 carbon atoms and having at least 2 carbon atoms extending in a chain between the adjoined S and O atoms,
  • R and R are alkylene radicals having 2 to 5 carbon atoms and having at least 2 carbon atoms extending in a chain between the adjoined S and O atoms, a phenylene radical or lower alkyl substituted phenylene radical with the proviso that n is 1 when R and -R are phenylene or lower alkyl substituted phenylene.
  • the alkenylsuccinic compound may also be reacted with a mixture of various proportions of the Sulfinyl-containing hydroxy compounds described in formulas A, B and C.
  • Sulfinyl containing hydroxy compounds within the scope of formulas A and B, when employed concurrently with one or more formula C alcohols, will act as chain terminators in the polyester reaction.
  • R groups are selected from straight chain and branched aliphatic hydrocarbon radicals such as methyl, ethyl, propyl, t-butyl, amyl, isohexyl, octyl, isooctyl, tertiary octyl, nonyl, decyl, dodecyl, t-dodecyl, ttetradecyl, hexadecyl, t-hexadecyl, eicosyl, tetracosyl, phenyl, napthyl, tolyl, t-butylphenyl, t-octylphenyl, t-dodecylphenyl, octadecylphenyl, tetracosylphenyl, benzyl, and phenylethyl.
  • Typical R alkylene groups are ethylene, propylene and butylene.
  • R and R groups are ethylene, propylene, butylene, phenyl, 3,5 dimethylphenyl and 3,5 ditertiarybutylphenyl.
  • Formula A compounds are well known.
  • the R radical of Formula A may represent a mixture of different alkylene groups and these groups may be provided by employing as reactants, in the preparation of the Formula A compound, mixtures of alkylene oxides such as ethylene oxide, propylene oxide and 1,2-butylene oxide.
  • Formula C type compounds are also described in the literature.
  • the sulfides corresponding to the compounds of Formula C are disclosed in US. Pat. 2,582,605 and these sulfides may be oxidized to sulfoxides by employing such conventional oxidation agents as hydrogen peroxide and peracids.
  • Representative peracids include peracetic acid, persulphuric acid and perbenzoic acid.
  • Formula B compounds are prepared by the co-condensation of a Formula A and Formula C compound.
  • the condensation reaction is accelerated by employing a condensation catalyst such as a strong mineral acid, i.e. sulfuric acid.
  • the alkenylsuccinic anhydride reactant is of the formua RCHC O CHr-hl
  • the alkenylsuccinamic acid is prepared by reacting an alkenylsuccinic anhydride with a compound having the formula:
  • a HN ⁇ wherein A is alkyl of 1 to 24 carbon atoms, phenyl, naphthyl, benzyl or -alkyl-substitu-ted phenyl, naphthyl or benzyl in which the total alkyl substituents contain up to 24 carbon atoms, and B is hydrogen or :alkyl of 1 to 24 carbon atoms.
  • a groups are methyl, ethyl, butyl, tbutyl, octyl, t-octyl, dodecyl, t-octadecyl, tetracosyl, phenyl, napthyl, benzyl, butylphenyl, octylphenyl, dodecylphenyl, dioctylphenyl, butylnapthyl, butylbenzyl, and octylbenzyl.
  • B may be hydrogen, methyl, butyl, octyl, dodecyl, octadecyl, eicosyl and tetracosyl.
  • a or B represents a t-alkyl radical with the remaining substituent being hydrogen.
  • Each of A and B may represent a single alkyl group or a mixture of alkyl groups.
  • either A or B may represent a mixture of t-alkyl groups containing 12 to 15 carbon atoms averaging 13 carbon atoms or a mixture of 18 to 24 carbon atoms.
  • Another preferred embodiment is when either A or B is a t-butyl radical and the remaining substituent is hydrogen.
  • the reaction between the formula D and formula E compounds to produce alkenylsuccinamic acids is conducted at a temperature of about 0 C. to 200 C., and preferably from 60 C. to 120 C.
  • the R group of Formula D is derived by polymerizing an olefin containing 2 to 18 carbon atoms, preferably 2 to 8 carbon atoms, by addition polymerization from substantially pure olefins.
  • These olefins may be either gaseous or liquid under normal conditions and frequently are obtained from the cracking of petroleum and other hydrocarbons.
  • Fractions containing olefinically unsaturated open-chain hydrocarbons are readily available over a wide range of molecular weights and derived from olefins of 2 to 18 carbon atoms.
  • the preferred olefins are those from 2 to 8 carbon atoms with particular emphasis on the olefin embodiments containing 4 carbon atoms. It is, of course, preferred to employ relatively pure olefins from which sulfur, cyclic compounds and other impurities have been removed.
  • Mixtures of various olefins, from ethylene to octadecene, may be used or individual embodiments, as desired. Mixtures of specific olefins, from ethylene to pentene, may be advantageously employed. Particularly advantageous for the present purposes are mixtures of the various butenes.
  • Butenes most commonly used comprise both straight and branched chain members. It is also possible, and frequently desirable, to employ a particular isomer, such as isobutylene, but for the purposes of this invention, separation or isolation of particular isomers is not essential. Thus, the mixtures readily available to the chemical industry are especially useful for the purposes of the present invention.
  • the olefinic polymers employed as starting materials vary from rather fluid liquids to rather viscous liquids at normal temperatures.
  • Typical olefinic polymers are those prepared from ethylene, propylene, isobutene, l-butene, 2-butene, l-pentene, 2-pentene, l-hexene, l-octene, 2-octene, l-decene, l-dodecene, 2-dodecene and l-octadecene.
  • R has been structurally presented as attached to a specific carbon atom with respect to Formula D, it will be understood by those skilled in the art that the R group may be positioned on the other carbon atom that is alpha to the other carbonyl group.
  • the R group enters the molecule concerned by a reaction involving maleic anhydride and, therefore, could be attached to either of the carbon atoms alpha to the carboxyl group. This invention encompasses fully this aspect.
  • the polyolefin is first reacted with maleic anhydride at temperatures of about 200 to 250 C. for a period of about 6 to 16 hours, as desired.
  • the maleic anhydride is used in excess, preferably about 1.5 to 3 times the stoichiometric amount. The use of excess maleic anhydride tends to maximize yields.
  • the polyolefin reacts with maleic anhydride to form a succinic anhydride derivative which can be separated from the excess maleic anhydride by vacuum distillation or similar treatment.
  • the product can be diluted with xylene or similar solvent and filtered.
  • the alkenylsuccinates of this invention are prepared by reacting an alkenylsuccinic anhydride, acid or amic acid with either a sulfinyl-containing monohydric alcohol (defined in Formulas A or B), a sulfinyl-containing dihydric compound (defined in Formula C) or mixtures of both.
  • a sulfinyl-containing monohydric alcohol defined in Formulas A or B
  • a sulfinyl-containing dihydric compound defined in Formula C
  • the resultant monoester and diester products may be represented by the following formulas:
  • R, R R and y represent the groups defined above.
  • The' acid group in Formula F may be esterified by reaction with any alkanol or phenol according to standard techniques and as described in U.S. application Ser. No. 412,237, filed Nov. 18, 1964.
  • Formula F and G esters may be prepared by reacting the alkenylsuccinic anhydride, acid or alkenylsuccinamic acid with the desired Formula A or B monohydroxy compoundat temperatures of from 25 to 220 C., and preferably from to 150 C. until esterification proceeds to the desired extent.
  • Employing an inert organic solvent in this reaction is discretionary.
  • the resultant product is a polyester which may be represented generally by the following formula:
  • R, R R and n represent the groups defined above and z represents the repeating unit of the polyester and may be an integer from 1 to 50 or more.
  • I reactants of this product may be heated at a temperature range of from to 220 C. and preferably from to C.
  • An inert organic solvent is necessary to azeotrope water from the reaction.
  • Suitable solvents are selected from aromatic hydrocarbons, aliphatic hydrocarbons and halogenated hydrocarbons.
  • the esterification reactions may be conducted in a mineral oil solution or dispersion or in combination with the inert organic solvent.
  • Preferred solvents include benzene, toluene and xylene. Cessation of the evolution of water indicated substantial completion of the reaction.
  • Another type of product within the scope of this invention is obtained by reacting one equivalent by weight of a dihydric compound as described in Formula C and two equivalents by weight of an alkenylsuccinic anhydride or acid.
  • This reaction product may be represented by the following formula:
  • the mole ratio of the alkenylsuccinic anhydride, acid or amic acid to the sulfinyl hydroxy compound may vary from about 110.5 to 1:2 or more. Therefore about one-half equivalent to about two moles of sulfinyl hydroxy compound per mole of acid compound is employed.
  • the compounds of this invention are useful as dispersants in lubricating oil and fuel systems. They may be used in the range of about 0.005 to 15% by weight of the oil or fuel composition and may be incorporated therein according to standard techniques. In fuels, the range is 0.005 to 5%, preferably 0.01 to 2%, by weight of the fuel composition. In lubricants, the range is 0.1 to 15 preferably 0.1 to by weight of the lubricant composition.
  • the compounds of the present invention as evaluated according to several known tests, exhibit outstanding activity as dispersants.
  • a single cylinder oil test engine is operated under conditions described in ASTM Special Technical Publication No. 315, published by the American Society for Testing and Materials, 191-6 Race Street, Philadelphia, Pa. 19103.
  • the engine may be rated at any time during the course of the test.
  • the 7 parts for sludge (CRC Merit, 10-clean) are the rocker arm assembly, rocker arm cover plate, valve deck, timing gear cover, push rod cover plate, push rod chamber and oil pan.
  • Panel Coker Test This test is described in the record of the Fifth World Petroleum Congress (1959) in an article by R. N. Jolie, Laboratory Screening Test for Lubricating Oil Detergents and Dispersants.
  • a sample of a compound under test is dissolved in a 170 SUS Mid- Continent Solvent Extracted Neutral containing 1% of a thermally unstable zinc dialkyldithiophosphate.
  • the blend is placed in a heated sump and is splashed against a heated panel held at 570 F. for 2 hours. Gain in weight of the panel is determined and compared with oil without the test compound.
  • the fuels contemplated are distillate fuels that boil from 75 to 750 F. which includes gasolines, along with jet and diesel fuels and furnace oils.
  • the present compounds are particularly useful in fuels that boil up to about 600 F., that is, the normal gasolines and jet fuels and similar liquid hydrocarbon fuels.
  • Lubricating compositions of this invention may be based on mineral oils or on synthetic lubricants.
  • the mineral oils may vary over a wide range of viscosity, such as l to 25 cs. at 210 F. These oils may be of naphthenic or parafiinic nature or may be of various mixtures. They may be distillates or mixtures of neutral oils and bright stocks.
  • the lubricants may be bodied or gelled and used as greases, if desired.
  • the oils may 8 vary from spindle oils or hydraulic oils to oils for reciprocating aircraft engines. They include oils for sparking combustion and compression ignition engines, varying from grades identified as S.A.E. 5 to S.A.E. 50. Other types of lubricants are also included, such as hydraulic and automatic transmission fluids.
  • the synthetic lubricants include esters, such as dioctyl, dinonyl or diisodecyl adipates, azelates or sebacates, polyethers and silicones. When use as hydraulic fluids is contemplated, phosphate esters are included as a base.
  • compositions there may also be used as a base, a transmission fluid, hydraulic fluid, gear oil or grease.
  • compositions of this invention there may be used one or more other additives, such as anti-oxidants, anti-foam agents, anti-rust agents, anti-wear agents, heavy duty detergents, pour-point depressants, viscosity index improvers, or other type of additive.
  • additives such as anti-oxidants, anti-foam agents, anti-rust agents, anti-wear agents, heavy duty detergents, pour-point depressants, viscosity index improvers, or other type of additive.
  • dithiophosphates such as zinc, barium or nickel dialkyldithiophosphate
  • sulfurized oils such as sulfurized sperm oil and sulfurized terpenes
  • polymers and copolymers from alkyl acrylates, methacrylate, itacouates or fumarates or vinyl carboxylates and mixtures thereof copolymers of acrylic esters and polar monoethylenically unsaturated compounds, such as N-vinyl-Z-pyrrolidinone, vinyl-pyridines, aminoalkyl acrylates or methacrylates or polyethyleneglycol acrylic esters, polybutenes, alkylphenolalkylene oxide condensates, alkenylsuccinic anhydrides, various silicones and alkyl
  • a turbo prop lubricant may be prepared by blending the compounds of this invention with di-2-ethylhexyl sebacate and a mixture of polyesters formed by condensing 2-ethyl- 1,3-hexane-diol and sebacic acid into the polyesters with 2-ethyl-hexanol, there being an average of about 3 glycol units per molecule.
  • This composition may also contain anti-oxidant, stabilizer or ether usefiul additives.
  • EXAMPLE 2 A mixture of 447 parts of the polybutenylsuccinic anhydride described in Example 1 and 59.2 parts of ethyl sulfinyl polyethoxyethanol (containing an average of 3.2 ethoxy units) was heated with stirring at 7090 for six hours. At the end of this time the infrared spectrum of the reaction solution showed no anhydride band indicating the reaction to the desired half-acid ester was complete. The final product after filtration contained 1.35% S (theory:
  • EXAMPLE 4 A mixture of 139 parts of polybutenylsuccinic anhydride with an anhydride content of 0.72 millimole/g. (prepared from maleic anhydride and polybutene of molecularsweight 950), 36.8 parts of benzylsulfinyl ethanol and 400 parts of xylene was heated at reflux (about 150 C.) until the theoretical amount of water of reaction was collected in an attached separator. The final product was obtained by vacuum stripping and filtration. Its acidity was 0.02 millimole/g., indicating essentially complete conversion to the diester.
  • EXAMPLE 5 A mixture of 362 parts of polybutenylsuccinic anhydride with an anhydride content of 0.276 millimole/ gm. (prepared from maleic anhydride and polybutene of molecular weight 2200), 70.2 parts of n-dodecylsulfinylpolyethoxyethanol (containing an average of ten ethoxy units) and 150 parts of toluene was stirred and heated at 90- 100 C. for twelve hours. At the end of this time, complete reaction to the half-acid ester had been effected as indicated by the complete disappearance of the anhydride band in the infrared spectrum. The final product was obtained by vacuum stripping of the volatile components at 100 C. and filtering.
  • EXAMPLE 12 A mixture of 1390 grams of a 90% solution in xylene of polybutenylsuccinic anhydride (prepared from maleic anhydride and polybutene of molecular weight 950), with an anhydride content of 0.720 millimole/ gram, and 130 grams of t-octylamine is stirred and heated at 100 C. for 10 hours. Vacuum stripping of the solvents and unreacted t-octylamine produce the intermediate amic acid (percent N: 0.90). Equimolar quantities of the amic acid 12 and ethylsulfinyl ethanol are reacted according to the procedure in Example 2 and the final product was vacuum stripped and filtered.
  • reaction product of (1) a compound selected from the group consisting of an alkenylsuccinic anhydride and an alkenylsuccinic acid and (2) at least one sulfinyl-containing hydroxy compound selected from those of the following formulas:
  • R is selected from the group consisting of (a) an alkyl hydrocarbon radical containing from 1 to 24 car- 'bon atoms, (b) an aryl hydrocarbon radical, (c) an aralkyl hydrocarbon radical wherein the alkyl portion of the radical contains from 1 to 4 carbon atoms and (d) an alkaryl hydrocarbon radical wherein the alkyl portion contains from 1 to 24 carbon atoms,
  • R is an alkylene radical having 2 to 5 carbon atoms and having at least 2 carbon atoms extending in a chain between the adjoined S and O atoms, and
  • R and R are alkylene radicals having 2 to 5 carbon atoms and having at least 2 carbon atoms extending in a chain between the adjoined S and O atoms, a phenylene radical or lower alkyl substituted phenylene radical with the proviso that n is 1 when R and R are phenylene or lower alkyl substituted phenylene,
  • reaction product being prepared at a temperature in the range of from 25 to 220 C. when the sulfinylcontaining hydroxy compound is a monohydroxy compound, and said reaction product 'being prepared at a temperature in the range of from to 220 C. when the hydroxy compound is a dihydric compound, and the ratio of the sulfinyl hydroxy compound per mole of acid compound being in the molar range of about one-half to about two,
  • alkenylsuccinic anhydride or alkenylsuccinic acid being a polybutenylsuccinic anhydride or acid.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4344853A (en) * 1980-10-06 1982-08-17 Exxon Research & Engineering Co. Functional fluid containing metal salts of esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols as antioxidants
US4702850A (en) * 1980-10-06 1987-10-27 Exxon Research & Engineering Co. Power transmitting fluids containing esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4122021A (en) * 1977-05-16 1978-10-24 Uniroyal, Inc. Antioxidant stabilized lubricating oils
US4760170A (en) * 1985-07-01 1988-07-26 Exxon Research & Engineering Co. Solution process for preparing metal salt esters of hydrocarbyl substituted succinic acid or anhydride and alkanols
US4776969A (en) * 1986-03-31 1988-10-11 Exxon Chemical Patents Inc. Cyclic phosphate additives and their use in oleaginous compositions
US4729839A (en) * 1986-05-29 1988-03-08 Phillips Petroleum Company Water soluble lubricating additives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4344853A (en) * 1980-10-06 1982-08-17 Exxon Research & Engineering Co. Functional fluid containing metal salts of esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols as antioxidants
US4702850A (en) * 1980-10-06 1987-10-27 Exxon Research & Engineering Co. Power transmitting fluids containing esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols

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