US3801507A - Sulfurized metal phenates - Google Patents

Sulfurized metal phenates Download PDF

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Publication number
US3801507A
US3801507A US00281863A US3801507DA US3801507A US 3801507 A US3801507 A US 3801507A US 00281863 A US00281863 A US 00281863A US 3801507D A US3801507D A US 3801507DA US 3801507 A US3801507 A US 3801507A
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sulfurized
reaction
sulfur
alkaline earth
metal
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Y Hendrickson
J King
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Chevron USA Inc
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Chevron Research and Technology Co
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    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Definitions

  • a novel multifunctional lube oil additive comprising the reaction product of an alkyl phenol having from 8 to 35 carbons in the alkyl group, sulfur and an alkaline earth metal oxide or hydroxide.
  • the reaction is performed in a two step process in the presence of a mutual solvent whereby the sulfurized metal phenate produced has a sulfur to metal atom ratio between about 1 and 2.
  • Lubricating oils used under the severe conditions of diesel and gasoline engines are highly compounded so as to neutralize acids derived from the oxidation of sulfur in the fuel and from partial oxidation of hydrocarbons, both from the fuel and oil; to disperse sludgeand varnishforming precursors within the oil; and to inhibit oxidation and wear; as well as enhancing other lubrication properties of the oil.
  • those oils which find use in railway diesel engines have the additional factor of not being corrosive or reactive to silver. Silver bearings are used in a preponderant number of diesel railway engines today.
  • the sulfurized metal phenate mixture of this invention is prepared by a two step processing scheme. Some advantages of the two-step process over a single step method include reduced undesired side reactions of the sulfur reactant with the mutual solvent and an improved base reserve.
  • First processing step In a first step an alkylated phenol having from 8 to 35 carbons in the alkyl group is contacted with sulfur and a small amount of an alkaline earth metal oxide or bydroxide and a mutual solvent, preferably ethylene glycol.
  • the reaction of the alkyl phenol, metal base and sulfur proceeds substantially as shown in the following chemical equation:
  • R is an alkyl group having from 8 to 35 carbons
  • x is an integer from 1 to 5
  • n is an integer from 0 to 15,
  • Y is the same or difierent constituent selected from H or /2M where the ratio of H to /zM is proportional to the ratio of M to alkyl phenol reacted;
  • M is an alkaline earth metal.
  • the above equation represents a broad and simplified version of both the reaction between the alkyl phenol, sulfur and metal base and the sulfurized intermediate reaction product.
  • the intermediate is not a pure compound having only one single structure, but, rather, is a mixture of numerous sulfurized compounds where n and x have several values.
  • the above formula indicates that a metal atom is bonded to or associated with at least one phenolic group in each molecule of the intermediate. However, because the composition is a mixture of compounds, it is recognized that some molecules of sulfurized alkyl phenol may not be bonded to or associated with a metal atom. Inversely, other molecules may have all of the phenolic groups neutralized by the metal base.
  • the metal atoms may be bonded to the phenolic group through a covalent bond or ionized and exist as cations within the intermediate product mixture.
  • the above processing step may be performed by either continuous or batch processing method, however, for purposes of illustration, the following discussion is related to the preferred batch processing. Modifications to continuous processing is within the skill of the art, and, in order to be concise, an independent discussion of continuous processing is not presented.
  • the three reactants are preferably charged to a suitable reaction vessel and agitated prior to the addition of the mutual solvent.
  • the mutual solvent is introduced into the vessel the exothermic reaction occurs with astrong evolution of hydrogen sulfide gas and water vapor.
  • a means for handling the large volumes of gaseous efiluents must be provided.
  • the reaction can be conducted at a temperature from 250 to 450 F. and a pressure of from 5 to 20 p.s.i.a.
  • Preferred reaction conditions include temperatures from 275 to 400 F. and pressures from to p.s.i.a.
  • the reaction proceeds at a moderate rate at the reaction conditions and usually varies from 1 to 6 hours.
  • a reaction diluent is preferably provided so as to allow easy handling of the reaction products during the processing steps.
  • the diluent may be added to the system before, during or after the reaction although it is preferred to add the diluent whenever necessary to reduce the viscosity of the mixtures to a desired value.
  • the concentration of alkyl phenol, alkaline earth metal base, sulfur and mutual solvent within the inert reaction diluent during the reaction is not important and may vary with the selection of reactants and process conditions, etc.
  • the molar ratio of the various components is an important aspect in the practice of the claimed invention and must be followed in order to realize the critical sulfur:metal ratio in the final sulfurized metal phenate product.
  • the ratios should be maintained as follows: 1 to 5 mols and preferably 1.5 to 3 mols of sulfur, 0.03 to 1.5 mols and preferably from 0.2 to 1 mol of alkaline earth metal base and 0.1 to 4 mols and preferably 0.2 to 1 mol of mutual solvent per mol of alkyl phenol.
  • the sulfur, alkyl phenol and alkaline earth metal base are charged to a reaction vessel equipped with a vent line and vacuum pump.
  • the reactor contents are heated to 250-285" F. under atmospheric pressure and the mutual solvent is charged to the reaction over a 16-30 minute period.
  • hydrogen sulfide and water are evolved and are removed from the system through the vent line.
  • the reaction is maintained at 2'65-285 F. for a period of 1 to 2 hours and then heated to a temperature of 350-365 F. for an additional 3 to 5 hours.
  • the reactor contents are cooled and a reaction diluent is charged to the reactor.
  • the sulfurized intermediate at this point contains some elemental or polysulfide sulfur (generally 2 to'10 weight percent) and is ready for use in the second processing step, although it is recognized that it may be filtered to remove any particulate matter or subjected to other purification steps or stored for later use.
  • the sulufurized intermediate is contacted with an additional amount of alkaline earth metal base and mutual solvent.
  • This step may be performed by batch or con-tinuous processing means.
  • the sulfurized intermediate is charged to the reactor along with the reaction solvent, usually a diluent oil, and alkaline earth metal base.
  • the three components are vigorously agitated to disperse the metal base throughout the mixture.
  • the mutual solvent is thereafter introduced into the admixure and catalyzes the exothermic reaction.
  • hydrogen sulfide and water vapor begin to evolve and are immediately taken olf overhead.
  • the delayed removal of the hydrogen sulfide and water vapor encourages the oxidation of some of the mutual solvents, such as ethylene glycol to glycolic acid, oxalic acid, etc., which in turn react with the metal base and reduce the base reserve of the product.
  • the reaction conditions which can be employed in this step can comprise temperatures between about 250 and 450 F. and preferably between 275 and 400 F. and pressures between 2 and 15 p.s.i.a. and preferably between 2 and 10 p.s.i.a.
  • the time required to neutralize the sulfurized intermediate with the metal base varies depending upon the reactants and mutual solvent selected, the concentrations employed, reaction conditions, etc. Generally, however, the reaction is completed after approximately 4 to hours. At the end of the reaction or concurrent with it, the mutual solvent is preferably stripped from the product.
  • the concentration of the sulfurized intermediate, alkaline earth metal base and mutual solvent within the reaction medium is not critical to the practice of this invention except that sufficient diluent is preferably employed to accommodate mixing and pumping of the product.
  • the ratio of components is important and should be within the following ranges: from 0 to 1.45 mols and preferably from 0.2 to 0.6 mol of alkaline earth metal base and from 0.5 to 4 mols and preferably from 0.5 to 2 mols of total mutual solvent present per mol of original alkyl phenol employed.
  • Table 2 illustrates the ratios of components employed:
  • R may be a straight chain or branched-chained alkyl group having from 8 to 35 carbon atoms and preferably from 10 to 30 carbon atoms.
  • the R group or alkyl group may be present on any of the sites around the phenolic ring, i.e., ortho, meta or para.
  • the R groups will predominantly be meta or para: That is, less than 40 percent of the R groups will be in the ortho position and preferably less than 15 percent of the R groups will be in the ortho position.
  • a particularly preferred alkylated phenol is polypropylene phenol, having from 9 to carbon atoms in the polypropylene group.
  • alkyls examples include, octyl, decyl, dodecyl, ethylhexyl, triacontyl, etc.; radicals derived from petroleum hydrocarbons such as white oil, wax, olefin polymers (e.g. polypropylene, polybutylene, etc.), etc. While one specific structure is indicated by the above formula, it should be recognized that mixtures of alkylated phenols can be successfully employed in the practice of this invention.
  • Alkaline earth metal base Several of the alkaline earth metal hydroxides or oxides may be employed in this invention. Exemplary compounds include calcium hydroxide, calcium oxide, barium hydroxide, barium oxide, etc. Combinations of the oxides and hydroxides of different alkaline earth metals may also be successfully employed herein. When magnesium is the selected metal it is preferred to employ magnesium methoxide or magnesium methyl carbonate rather than the oxide or hydroxide form.
  • the calcium and barium bases are preferred and calcium bases most preferred such as calcium oxide and calcium hydroxide.
  • the presence of a mutual solvent is critical in the practice of this invention.
  • the solvent can comprise any stable organic liquid which has appreciable solubility for both the alkaline earth metal base and the alkyl phenol and sulfurized intermediate.
  • Exemplary mutual solvents include ethylene glycol, 1,4-butane diol, derivatives of ethylene glycol, such as the monomethyl ether, monoethyl ether, etc.
  • the vicinal glycols are preferred and ethylene glycol is most preferred since it serves to activate the neutralization reaction and to that extent typifies a catalyst, although the exact characteristics describing is function are unknown.
  • a minimum of 0.1 mol of mutual solvent per mol of alkyl phenol originally charged is generally required in the first reaction step and a minimum of 0.5 mol of mutual solvent per mol of alkyl phenol originally charged is required in the second reaction step.
  • a ratio of 2:1 the necessary reactor volume is unduly increased and the reclamation of the solvent becomes a problem although a ratio as high as 4:1 is operable.
  • the reaction diluent employed in the subject invention is preferably a mineral lubricating oil obtained from paraffiuic, naphthenic, asphaltic or mixed base crudes and/ or mixtures thereof having a flash point above about 350 F.
  • the reaction diluent serves to reduce the viscosity of the sulfurized intermediate and the sulfurized metal phenate product to make them readily transferable by pumping operations and the like.
  • Mineral lubricating oils are preferred since the ultimate use of the sulfurized metal phenates is in oil additives. However, any inert water-insoluble organic medium which would not react or interfere with the reaction of the process would be suitable.
  • a particularly preferred reaction diluent is refined mid-continental neutral oil having a viscosity of about SUS at 100 F.
  • the lubricant composition of this invention can be prepared by simply mixing the sulfurized metal phenates produced in the above step within a suitable lubricating oil or lubricating oil compositions.
  • concentration of sulfurized metal phenate within the lubrication oil composition to realize the superior antioxidant and base reserve properties varies depending upon the type of sulfurized metal phenate selected, the particular properties desired and the type of lubricating oil selected. Generally, however, the concentration of the sulfurized metal phenate ranges from 0.5 to 15 weight percent and more preferably from 1 to 8 weight percent.
  • the lubricating oil compositions generally have a sulfur content between about 0.03 and 3 weight percent and an alkaline earth metal content derived from the subject phenate between about 0.08 and 0.3 weight percent.
  • the lubricating oil which may be employed in the practice of this invention including a wide variety of natural and synthetic oils such as naphthenic base, paraflin base and mixed base lubricating oils.
  • the oils generally have a viscosity of 35 to 50,000 SUS at 100 F. or from 30 to SUS (Saybolt Universal Seconds) at a temperature of 210 F.
  • hydrocarbon oils include oils derived from coal products and synthetic oils, e.g., alkylene polymers, (such as polymers of propylene, butylene, etc., and mixtures thereof), alkylene oxide type polymers (e.g., alkylene oxide polymers prepared by polymerizing alkylene oxide, e.g., propylene oxide polymers, etc., in the presence of water or alcohols, e.g., ethyl alcohol, carboxylic acid esters (e.g., those which were prepared by esterifying such carboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkenyl succinic acid, fumaric acid, maleic acid, etc., with the alcohol such as butyl alcohol, hexyl alcohol, 2-ethylhexyl alcohol, pentaerythritol, etc.), liquid esters of phosphorus acids, alkyl benzenes, polyphenols (e.g., bi
  • lubricating oils may be used individually or in combinations, Whenever miscible or whenever made so by use of mutual solvents.
  • additives may be successfully employed within the lubricating composition of this invention without affecting its multi-functional properties.
  • exemplary additives include stabilizers, extreme pressure agents, tackiness agents, pour point depressants, lubricating agents, viscosity index improvers, color correctors, odor control agents, antiwear agents, antioxidants, metal deactivators, anticorrodants, etc.
  • EXAMPLE 1 In this example a representative sulfurized metal phenate is prepared by the two step processing method of this invention.
  • a 4000-gallon closed reaction vessel equipped with a stirrer, cooling coils, a thermometer, several inlet lines, a nitrogen gas inlet and a vacuum vent is charged with 18,020 pounds of tetrapropylene phenol, and 1,125 pounds of calcium oxide (98 percent purity).
  • the contents are agitated and heated to 220 F.
  • 4,160 pounds of powdered sulfur are charged to the reactor and the mixture heated to 265-275 F.
  • Ethylene glycol (880 pounds) is then charged to the reactor, and the cooling water is circulated through the cooling coils to maintain the reactor contents between 265 and 275 F. during the glycol addition.
  • the temperature is then allowed to increase 5 F. and maintained at that temperature for about 1 hour.
  • the contents are then heated to 355360 F. and maintained at that temperature for an additional 4 hours.
  • the reactor contents are cooled and charged with 500 gallons of diluent oil having a viscosity of about 100 SUS at 100 F.
  • the pressure on the system is maintained at substantially atmospheric with hydrogen sulfide and water vapor being removed overhead as they are evolved during the reaction.
  • pounds of fresh ethylene glycol is quickly charged to the reactor.
  • the temperature of the system is allowed to slowly increase to 300 F. over a 2 /2 hour period.
  • a 25-inch vacuum is applied and maintained for 30 minutes.
  • the temperature is slowly increased to 390 F. under this vacuum to strip the ethylene glycol from the crude sulfurized calcium phenate.
  • the stripping operation takes approximately 4 hours.
  • the vacuum is broken and the contents cooled to 250 F.
  • An additional gallons of diluent oil (100 neutral) are added to the final product.
  • a representative sample of the product is recovered and the sulfurized metal phenate analyzed.
  • the typical calcium content measured is found to be 4.5 weight percent (ASTM D811) and the typical sulfur content measured at 4.9 weight percent (ASTM D1552).
  • the typical molar ratios of the various reactants in the final product are found to be as follows:
  • EXAMPLE 2 In this example a series of tests are performed with oils compounded with various sulfurized metal phenates having varying sulfurzcalcium ratios and compared to the product prepared by the method of Example 1. The test is conducted in a glass cell consisting of a 100 m1. sample compartment, a stirring mechanism and a compart ment holding solid sodium or potassium hydroxide pellets which serve as a drying agent as well as absorbent for volatile acidic oxidation products. The drying agent has only vapor phase contact with the liquid in the sample compartment. The cell is only open to a 1.5-liter bell jar ifilled with 99.85% oxygen 'kept at atmospheric pressure. In each test a 25-gram sample of compounded oil and 0.2 ml.
  • the compounded oils tested consist of a mid continent SAE 30 grade neutral refined oil containing 3.5 weight percent of a succinimide dispersant and 80 millimols of calcium in the form of one of the various sulfurized metal phenates described in Table 3 below.
  • the oxidation catalyst a solution of metal naphthenates in kerosene, supplies 52 p.p.m. copper, 31 p.p.m. iron, 27 p.p.m. tin, 26 p.p.m. manganese and 603 p.p.m. lead in oil soluble form to the composition being tested.
  • EXAMPLE 3 The advantage of employing a two step process of this invention over a single step reaction scheme is illustrated by this example.
  • a 3 liter reaction vessel equipped with a stirrer, thermometer, condenser and dropping funnel is charged with 661 grams of 100 neutral oil, 747 grams of tetrapropylenephenol, 197 grams of sulfur and 144 grams of calcium hydroxide.
  • the mixture is heated to 260 F. under a vacuum of mm. of Hg and vigorously agitated. Thereafter 346 grams of ethylene glycol are added to the mixture over a 20 minute period and the temperature allowed to increase to about 300 F.
  • the temperature is maintained at 300 F. under a 10-inch Hg vacuum for a period of 2 hours. Thereafter, the temperature is increased to 386 F. over a 2 /2 hour period while simultaneously reducing the pressure to 11 mm. Hg.
  • the contents are held at a temperature of 386 F. and pressure of 11 mm. Hg for 15 minutes and thereafter cooled and filtered.
  • a sample of the crude sulfurized metal phenate is filtered through diatomaceous earth and found to contain 5.54 weight per cent sulfur and 4.44 weight percent calcium to yield a S/Ca ratio of 1.56.
  • the product had an alkalinity value of 114.3 mg. KOH/g. corresponding to a basic calcium content of 4.07%.
  • EXAMPLE 4 This example is presented to demonstrate the superiom'ty of the sulfurized metal phenates of this invention over another sulfurized metal phenate having a sulfurzmetal ratio below 1 and over a conventional sulfurized amino metal phenate.
  • six cylinder Caterpillar engines are employed and subjected to Caterpillar Tractor Company Test Procedure ET-40-l.
  • a crankcase oil formulation containing one of the sulfurized metal phenates, is prepared and employed in the Caterpillar engine. The engine is operated under severe conditions until ring sticking occurs at which time the engine is turned off, disassembled and inspected. The time required to cause the ring sticking to occur is recorded and is indicative of the dispersant and antioxidant properties of the sulfurized metal phenate employed.
  • the test engine is a six cylinder Caterpillar D353 TA (turbocharged with an aftercooler) engine having a 6.25 inch ibore, 8.0-inch stroke, 1473 cubic inch displacement and 490 brake horsepower at 1300 r.p.m.
  • the operating conditions during the test is shown in the following Table 5.
  • crankcase oil formulations consisted of RPM SAE 30 weight base of containing 2 weight percent of a conventional ashless dispersant, 20 millimols per kilogram of a conventional metallic dispersant and millimols per kilogram of the sulfurized metal phenate based on the metal content.
  • Test Oil A contains a sulfurized calcium phenate prepared by reacting calcium hydroxide with a tetrapropylene phenol and sulfur in the presence of ethylene glycol and has a sulfur to calcium weight ratio of about 0.4.
  • Test Oil B contains a sulfurized calcium phenate prepared by the method of Example 1 and having a sulfur to calcium weight ratio of about 1.1. The results of the Caterpillar engine tests are reported in the following Table 6.
  • a composition of matter prepared by reacting an alkyl phenol having from 8 to 35 carbon atoms in the alkyl group, sulfur and an alkaline earth metal base in the presence of a mutual solvent to form a sulfurized metal phenate having a sulfur to metal atom ratio between 1 and 4.
  • composition of matter comprising a major portion of an oil of lubricating viscosity and from 0.5 to 15 weight percent of a composition as defined in claim 1.
  • a process for producing a mixture of sulfurized metal phenates having a sulfur to metal atom ratio between 1 and 4 which comprises:
  • a process for producing a mixture of sulfurized metal phenates having a sulfur to metal atom ratio between 1 and 4 which comprises:
  • said contacting in the second step being maintained at a temperature of 250 to 450 F. and a pressure of 2 to 15 p.s.i.a. for a period of 2 to 10 hours to produce a sulfurized metal phenate mixture. 1 v.
  • composition defined in claim 13 wherein .said mutual solvent is 1,4-butanediol.

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US3932289A (en) * 1973-11-09 1976-01-13 Chevron Research Company Preparation of overbased carbonated sulfurized magnesium alkylphenates
US3969235A (en) * 1974-08-26 1976-07-13 Texaco Inc. Sulfurized calcium alkylphenolate compositions
US4016093A (en) * 1976-03-19 1977-04-05 Mobil Oil Corporation Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same
US4196089A (en) * 1978-06-20 1980-04-01 Witco Chemical Corporation Preparation of overbased magnesium sulfurized phenates
US4228022A (en) * 1979-06-28 1980-10-14 Chevron Research Company Sulfurized alkylphenol-olefin reaction product lubricating oil additive
US4710308A (en) * 1982-04-08 1987-12-01 Amoco Corporation Process for preparing overbased sulfurized phenates
EP0240327A2 (en) 1986-03-31 1987-10-07 Exxon Chemical Patents Inc. Cyclic phosphate additives and their use in oleaginous compositions
US5178781A (en) * 1989-06-23 1993-01-12 Cosmo Oil Co., Ltd. Process for producing over-based sulfurized alkaline earth metal phenate type detergent
US4973411A (en) * 1989-09-15 1990-11-27 Texaco Inc. Process for the preparation of sulfurized overbased phenate detergents
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BE803684A (fr) 1973-12-17
GB1445327A (en) 1976-08-11
CA1010850A (en) 1977-05-24
AU5935473A (en) 1975-02-20
JPS49108105A (xx) 1974-10-15
ZA735545B (en) 1974-09-25
BR7306325D0 (pt) 1974-07-18
IT992910B (it) 1975-09-30
USRE29661E (en) 1978-06-06
AU472573B2 (en) 1976-05-27
JPS532161B2 (xx) 1978-01-26
FR2196384B1 (xx) 1976-06-18
GB1440373A (en) 1976-06-23
FR2196384A1 (xx) 1974-03-15
DE2339120A1 (de) 1974-02-28

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