US3574576A - Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine - Google Patents

Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine Download PDF

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US3574576A
US3574576A US488775A US3574576DA US3574576A US 3574576 A US3574576 A US 3574576A US 488775 A US488775 A US 488775A US 3574576D A US3574576D A US 3574576DA US 3574576 A US3574576 A US 3574576A
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molecular weight
percent
hydrocarbon
polyisobutenyl
engine
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Lewis R Honnen
Robert Gordon Anderson
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Chevron USA Inc
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Chevron Research and Technology Co
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/58—Heterocyclic compounds
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
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    • C08F8/00—Chemical modification by after-treatment
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
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    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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Definitions

  • This invention concerns novel high molecular weight hydrocarbon polyamines and their use as detergents in fuels and lubricating oils. More particularly, this invention concerns novel high molecular weight branched chain aliphatic hydrocarbon substituted polyamines, their use as detergents in fuels and lubricating oils and the fuel and lubricating oil compositions containing the novel polyamines.
  • compositions of this invention have molecular Weights in the range of about 450 to 10,000, more usually in the range of 450 to 5,000 and preferably in the range of 450 to 3,500.
  • compositions of this invention are described by the following formula:
  • the alkylene radical indicated as U, will have from 2 to 6 carbon atoms, the nitrogens connected by U being separated by at least 2 carbon atoms. (By alkylene is intended the normal meaning that the valences be on different carbon atoms.)
  • the alkylene group may be straight chain or branched. Various alkylene groups include ethylene, 1,2-propylene, trimethylene, pentamethylene, hexamethylene, Z-methyl 1,3-propylene, etc.
  • the hydrocarbon radical indicated by R may have a variety of structures and may be aliphatic or alicyclic, and is generally free of aromatic unsaturation.
  • the hydrocarbon radical may be a polymer of olefins of from 2 to 6 carbon atoms (if ethylene is used, the ethylene will be copolymerized with an olefin of at least 3 carbon atoms) or may be derived from naturally occurring products of relatively high molecular weight, e.g., naphthenic bright stock.
  • the alkylene polyarnines may be derived from various amino compounds such as ethylene diamine, diethylene triamine, tetraethylene pentamine, octaethylene nonamine,, nonaethylene decamine, 2-aminoethyl piperazine, 1,3-propylene diamine, 1,2-propylene diamine, tetramethylene diamine, etc.
  • compositions of this invention will generally be of the following formula:
  • a an integer of from 0 to 5 b an integer of from '0 to l a +2b -an integer in the range of from 1 to 5 c an integer or fractional number in the range of l to 3, generally per molecule there being fewer R groups than nitrogen atoms d-an integer in the range of 2 to 3 R a branched chain aliphatic radical of from about 400 to 3,000 molecular weight.
  • R is an aliphatic branched chain hydrocarbon radical.
  • R may be aliphatically saturated or have aliphatic unsaturation, e.g., olefinic.
  • R will have from 0 to 1 sites of aliphatic unsaturation.
  • branching it is intended that on the average there be at least one branch per 6 carbon atoms along the chain, preferably at least 1 branch per 4 atoms along the chain and particularly preferred that there be from 0.5 to 1 branch per carbon atom along the chain (at least one branch per two carbon atoms along the chain).
  • the branched chain aliphatic hydrocarobn radical is readily prepared by polymerizing olefins of from 2 to 6 carbon atoms (copolymerizing an olefin of from 3 to 6 carbon atoms with ethylene) and preferably polymerizing olefins of from 3 to 6 carbon atoms, particularly isobutylene.
  • a single compound will not be used as a reactant in the preparation of the compounds of this invention. That is, mixtures will be used in which one or two compounds will predominate and the average composition or molecular weight is indicated.
  • tetraethylene pentamine prepared by the polymerization of aziridine or reaction or dichloroethylene and V amine and the empirical formula of the total composition will closely approximate that of tetraethylene pentamine.
  • the molecular weight reported for the branched chain aliphatic hydrocarbon group is an average for a mixture which is sharply peaked when graphing the number average molecular weight distribution.
  • the nitrogens of the alkylene polyamines are not equivalent, substitution on different nitrogens will afford different compounds.
  • the alkylene polyamines may have only one hydrocarbon substituent or may be polysubstituted with hydrocarbon radicals.
  • the mono-substituted alkylene polyamine compositions will have the following formula:
  • R a branched chain aliphatic hydrocarbon radical derived from polymerizing olefins of from 3 to 6 car bon atoms, preferably of from 3 to 4 carbon atoms, and particularly preferred of propylene and isobutylene and having a molecular weight in the range of 400 to 3,000, preferably 400 to 2,500.
  • N-polyisobutenyl ethylene diamine N-polypropenyl ethylene diamine, N-poly(l-butenyl) ethylene diamine, N-(alternating copolymers of ethylene and isobutylene) ethylene diamine (alternating copolymers of ethylene and isobutylene may be achieved by the cationic polymerization of 4-methylpentene-l), N-polypropenyl Z-aminoethylpiperazine, N-polyisobute'nyl 2-aminoethylpiperazine, N-polypropenyl diethylene triamine, N-polyisobutenyl diethylene triamine, N-po1y(1-pentenyl) diethylene tria mine, N-polypropenyl trimethylene diamine, N-polyisobutenyl trimethylene diamine, N-polypropenyl di(trimethylene) triamine, N-
  • N-polyisobutenyl di(1,2-propylene) triamine N-polypropenyl triethylene tetramine, N-polyisobutenyl triethylene tetramine, N-(alternating copolymer of ethylene and isobutylene) triethylene tetramine, N-polypropenyl tetraethylene pentamine, N-polyisobutenyl tetraethylene pentamine, N-polyisobutenyl pentaethylene hexamine, etc.
  • the polyhydrocarbon radical substituted alkylene polyamine compositions have the following formula:
  • a --an integer of from to 5 preferably an integer of (As indicated by the above formula, the number of hydrocarbon substituents need not be a whole number when averaged over the total composition; generally, a mixture will be obtained containing mono-, diand trior higher substituted molecules averaging out to a fractional or whole number.)
  • N,N'-di(polypropenyl) diethylene triamine N,N-di(polyis obutenyl) diethylene triamine
  • N, N-di(polyisobutenyl) triethylene tetramine N,N'-di- N-di(polyisobutenyl) triethylene tetramine
  • N,N'-di (polypropenyl) tetraethylene pentamine N,N'-di(poly isobutenyl) tetraethylene pentamine
  • N,N',N-tri(polyisobutenyl) tetraethylene pentamine N,N-di(polyisobutenyl) Z-aminoethylpiperazine, N,N'-di(poly-1-butenyl) triethylene tetramine, N,N'-di(polyisobuten
  • compositions are those having the straight chain alkylene polyamines, particularly ethylene diamine and polyethylene polyamines. These compositions have the following formula:
  • R a branched chain aliphatic hydrocarbon radical of from 40 to 3,000 molecular weight, preferably of from 400 to 2,500 molecular weight, and, particularly preferred, either polypropenyl or polyisobutenyl.
  • compositions of this invention are readily prepared by combining an aliphatic or alicyclic halide with the desired amine in the proper mole proportions.
  • the halide is prepared from the hydrocarbon by halogenation: ionically or free radically.
  • the hydrocarbon groups may be prepared by ionic or free radical polymerization of olefins of from 2 to 6 carbon atoms (ethylene must be copolymerized with another olefin) to an olefin of the desired molecular weight.
  • the olefins which find use are ethylene, propylene, isobutylene, l-butene, l-pentene, 3- methyl-l-pentene, 4-methyl-l-pentene, etc., preferably propylene and isobutylene.
  • branch per 6 carbon atoms along the chain there should be at least one branch per 6 carbon atoms along the chain and preferably at least one branch per 4 carbons alongthe chain.
  • the preferred olefins, propylene and isobutylene have from 0.5 to 1 branch per atom along the hydrocarbon chain.
  • various naturally occurring materials may be used which have the desired molecular weight and aliphatic or alicyclic character.
  • the halogen may be introduced into the hydrocarbon molecule by various means known in the art. Most readily, either chlorine or bromine (halogen of atomic number 17-35) may be introduced by the free radical catalyzed halogenation of the hydrocarbon, or ionic addition to olefinic unsaturation.
  • Various free radical catalysts may be used, such as peroxides, azo compounds, bromine, iodine, as well as light. Ionic catalysts are exemplified by ferric chloride. Methods of halogenation are well known in the art and do not require extensive exemplification or illustration here.
  • the amount of halogen introduced will depend on the particular hydrocarbon used, the desired amount of amine to be introduced into the molecule, the particular alkylene amine used, and the halogen used.
  • the amount of halogen introduced will generally be in the range from about 1 to 5 halogen atoms per molecule, depending on the reactivity of the resulting halide. On a weight percent basis, the amount of halide will generally range from about 1 to 25, more usually from about 1 to 10.
  • the halohydrocarbon and alkylene polyamine or polyalkylene polyamine may be brought together neat or in the presence of an inert solvent, particularly a hydrocarbon solvent.
  • the inert hydrocarbon solvent may be a1iphatic or aromatic.
  • aliphatic alcohols may be used by themselves or in combination with another solvent, when capable of dissolving the reactants.
  • the reaction may be carried out at room temperature (20 C.), but elevated temperatures are preferred. Usually, the temperature will be in the range of from about 100 to 225 C. Depending on the temperature of the reaction, the particular halogen used, the mole ratios and the particular amine, as well as the reactant concentrations, the time may vary from 1 to 24 hours, more usually from about 3 to 20 hours. Times greatly in excess of 24 hours do not particularly enhance the yield and may lead to undesirable degradation. It is therefore preferred to limit the reaction time to fewer than 24 hours.
  • the mole ratio of halohydrocarbon to alkylene amine will generally be in the range from about 0.2 to 10 moles of alkylene amine per mole of halohydrocarbon, more usually 0.5 to 5 moles of alkylene amine per mole of halohydrocarbon.
  • the mole ratio will depend upon the amount of halogen present in the halohydrocarbon, the particular halogen and the desired ratio of hydrocarbon to amine. If complete suppression of polysubstitution of the alkylene polyamines is desired, then large mole excesses of the amine Will be used.
  • the residual halogen as bound halogen will be in the range of 0 to weight percent of the composition.
  • Small amounts of halogen may be present as the hydrohalide salt of the hydrocarbon substituted alkylene polyamines.
  • the hydrocarbons used will have aliphatic unsaturation.
  • the amines may react in a way resulting in the elimination of hydrogen halide, introducing further aliphatic unsaturation into the hydrocarbon radical. Therefore, the hydrocarbon radicals usually will be olefinically unsaturated.
  • the olefinic unsaturation does not significantly affect the utility of the product, and when available, saturated aliphatic halide may be used.
  • reaction mixture may be extracted with a hydrocarbon medium to free the product from any low molecular weight amine salt which has formed.
  • the product may then be isolated by evaporation of the solvent. Further separation from unreacted hydrocarbon or purification may be carried out as desired, e.g., chromatography.
  • the reaction may be carried out in the medium in which it will ultimately find use and be formed at concentrations which provide a concentrate of the detergent composition.
  • the final reaction mixture may be in a form to be used directly upon dilution in lubricating oils or fuels.
  • compositions encompassed by this invention have a broad spectrum of uses as detergents and dispersants, Not only do they find use as detergents and dispersants in lubricating oils under the hot conditions of the diesel engine and the relatively cooler conditions of the automobile internal combustion engine, where wide fluctuations in temperature occur, but the detergents of this invention may also be' used in 2- cycle spark ignition engineswhere the lubricating oil containing the detergent is introduced into the fuelar1d directly in fuels, such as diesel and gasoline fuels. Because of the broad changes in conditions under which the compositions of this invention will operate, there will be to some degree, preferred subgenera for the various uses. Moreover, depending on the particular use, different additives will be used in conjunction with the detergents and the dispersants of this invention. Finally, obviously the media in which the detergents and the dispersants will be employed will vary depending on Whether a lubricating oil or a fuel is used and how the lubricating oil is to be employed.
  • the lubricating oil composition will be considered first.
  • Preferred detergents and dispersants for lubricating oils have the following formula:
  • R a -an integer of from 2 to 4 c -a number in the range of from 1 to 2, including whole and fractional numbers
  • R a branched chain aliphatic hydrocarbon radical of from about 750 to 3,000 molecular weight, more preferred of from about 750 to 1,500 molecular weight.
  • Illustrative preferred compounds are: polyisobutenyl triethylene tetramine, di(polyisobutenyl) tetraethylene pentamine, polypropenyl diethylene triamine, polyisobutenyl triethylene tetramine, etc.
  • the preferred hydrocarbon radicals are polyisobutylene and polypropylene.
  • the detergents may be prepared as concentrates having as high as weight percent of the detergent in lubricating oil. Generally, concentrates will vary from about 10 to 80 weight percent. However, when the oil is to be used in the engine, the amount of the detergent generally will vary from about 0.1 .to 15 weight percent, more usually from 0.25 to 10 weight percent. The lubricating oil compositions may therefore vary in the amount of detergent from 0.1 to 80 weight percent.
  • compositions of this invention can be used with various base oils which find use as lubricating oils.
  • Naturally occurring base oils include naphthenic base, paraflin base, asphaltic base and mixed base lubricating oils.
  • Synthetic hydrocarbon oils include alkylene polymers, such as polymers of propylene, butylene, l-octene, and mixtures thereof and alkylated aromatic hydrocarbons.
  • Nonhydrocarbon lubricating oils include: alkylene oxide type polymers; carboxylic acid esters such as octyl adipate, nonyl azelate, decyl suberate, butyl alkenylsuccinate, etc.; also, inorganic esters such as phosphates and silicates.
  • the above base oils may be used individually or in combination, whenever miscible or made so by the use of mutual solvents.
  • the detergents of this invention are used in lubricating oils with an oxidation inhibitor and extreme pressure agent.
  • the preferred inhibitors are metal dithiophosphates, particularly zinc 0,0-di(hydrocarbyl) phosphorodithioate, where the hydrocarbyl groups are generally from 4 to 36 carbon atoms.
  • Hydrocarbyl is an organic radical composed solely of carbon and hydrogen which may be aliphatic, alicyclic, aromatic or combinations thereof, e.g., aralkyl or alkaryl, and may be aliphatically saturated or unsaturated, e.g., ethylenic unsaturation.
  • the hydrocarbyl groups are alkyl or alkaryl groups.
  • S-alkyl and S-polyalkyleneoxy esters of the phosphorodithioate may be used. Usually, about 6 to 50 mM./ kg. of the phosphorodithioate is used in the oil.
  • additives may also be included in the lubricating oil. These additives include pour point depressants, viscosity index improvers, antiwear agents, rust inhibitors, corrosion inhibitors, other detergents and dispersants, etc. Generally, the total amount of additives exclusive of the detergent will be in the range of from about 0.1 to 5 weight percent of the lubricating oil composition.
  • a special situation in which the lubricating oil is employed is the 2-cycle spark ignition engine.
  • the oil With the 2- cycle engine, the oil is incorporated with the fuel and burned directly in the piston chamber.
  • the oil/ gasoline mixture first enters the crankcase Where the mixture of lubricant and unvaporized fuel contacts and lubricates the various moving parts including the bearings, pistons, piston rings and cylinders. Any lubricant that does not deposit on the surfaces in the lower part of the engine passes into the combustion chamber where it is burned along with the fuel.
  • An effective detergent solubilizes any deposit precursors and the deposit precursors are. carried into the combustion chamber and burned. While the dispersant and detergent is considered a lubricating oil additive, the detergent operates in a mixed lubricating oilfuel environment.
  • compositions for use in the 2-cycle engine have the following formula:
  • a an integer of from 1 to 4 c an integer or fractional number of from 1 to 2, preferably 1 R a branched chain aliphatic hydrocarbon radical having a molecular weight of from about 750 to 1,500, preferably a polymer of propylene or isobutylene.
  • Illustrative compounds which come within the above formula are polyisobutenyl ethylene diamine, polypropenyl ethylene diamine, as well as the previously indicated compounds which are included in the above formula.
  • hydrocarbonaceous lubricating oils will be used, particularly petroleum derived, such as the mixed base, paraffinic and naphthenic base oils.
  • phosphorodithioate inhibitors other oxidative inhibitors such as bis(phenols), etc. may be used.
  • concentrations in the oil may be as low as one mM./kg.
  • a halide scavenger for the lead will also be added, usually to enhance the halide already present in the gasoline.
  • Alkylene halide scavengers such as ethylene dibromide may be used with the detergent compositions of this invention, but aryl halides, e.g., dichlorobeuzene, are preferred.
  • aryl halides e.g., dichlorobeuzene
  • Other additives already described for the lubricating oils, may also be included.
  • R" a branched chain aliphatic hydrocarbon radical of from about 450 to 1,500 molecular weight, preferably polypropylene or polyisobutylene.
  • the detergent Will generally be employed in a hydrocarbon base fuel.
  • the detergent additive may be formulated as a concentrate, using a suitable hydrocarbon alcohol solvent boiling in the range of about 150 to 400 F.
  • a suitable hydrocarbon alcohol solvent such as benzene, toluene, xylene or higher boiling aromatics or aromatic thinners.
  • Aliphatic alcohols of about 3 to 8 carbon atoms, such as isopropanol, isobutylcarbinol, n-butanol and the like, in combination with hydrocarbon solvents are also suitable for use with the detergent additive.
  • the amount of the additive will be ordinarily at least 10 percent by weight and generally not exceed 70 percent by weight.
  • the amount of the detergent used in the fuel will generally be from about 100 to 1,000 ppm.
  • antiknock agents e.g., tetramethyl lead or tetraethyl lead.
  • lead scavengers such as aryl halides, e.g., dichlorobenzene or alkyl halides, e.g., ethylene dibromide.
  • a nonvolatile light mineral lubricating oil such as petroleum spray oil is also a suitable additive for the gasoline compositions used with the detergents of this invention and its use is preferred. These oils are believed to act as a carrier for the detergent and assist in removing and 8 preventing deposits. They are employed in amounts from about 0.05 to 0.5 percent by volume, based on the final gasoline composition.
  • EXAMPLE 3 Into a reaction flask was introduced 1,780 g. of brominated polyisobutylene (polyisobutylene of approximately 930 average molecular weight brominated to 8.6 weight percent bromine) and 350 g. of a mixture of polyethylene amines having an average composition of tetra ethylene pentamine and allowed to stand overnight at ambient temperatures. The mixture was then heated at C. for several hours (approximately 5 to 6), cooled and diluted with several volumes of n-pentane and allowed to stand. The solution was then concentrated to about one-half its original volume, about 1 liter of ethanol and about 1 liter of 10 percent aqueous sodium carbonate added.
  • brominated polyisobutylene polyisobutylene of approximately 930 average molecular weight brominated to 8.6 weight percent bromine
  • a mixture of polyethylene amines having an average composition of tetra ethylene pentamine and allowed to stand overnight at ambient temperatures.
  • the mixture was then heated
  • EXAMPLE 4 Into a reaction flask was introduced 433 g. of chlorinated polyisobutylene (polyisobutylene of approximately 950 average molecular weight chlorinated to 9.3 weight percent chlorine) and 240 g. of alkylene polyamine having an average composition of tetraethylene pentamine and 640 ml. of benzene added. The mixture was heated to reflux and the benzene distilled off. The residue was then heated at 150 C. for 4 hours. After cooling the reaction mixture and diluting with mixed hexanes, 200 ml. of ethanol was added and the organic phase extracted with 10 weight percent aqueous sodium carbonate, the phases separated and the extraction of the organic phase repeated,
  • EXAMPLE 6 Into a reaction flask was introduced 3,000 g. of a 70 weight percent solution in benzene of chloropolyisobutylene (polyisobutylene of approximately 1,300 molecular Weight chlorinated to 4.3 weight percent chlorine) and 210 g. of alkylene polyamine having an average composition of triethylene tetramine and the mixture heated to reflux, the benzene stripped off and the mixture further heated at 170 C. for 4 hours. At the end of this time, the mixture was allowed to cool, and then diluted with equal volumes of mixed hexanes and absolute ethanol, heated to reflux and then one-third volume of weight percent aqueous sodium carbonate added.
  • chloropolyisobutylene polyisobutylene of approximately 1,300 molecular Weight chlorinated to 4.3 weight percent chlorine
  • alkylene polyamine having an average composition of triethylene tetramine
  • reaction mixture was transferred to a separatory funnel with the aid of one liter of benzene, and the mixture washed repeatedly first with a dilute aqueous solution of isopropyl alcohol, then with a dilute aqueous solution of a combination of isopropyl alcohol and butanol and finally with water.
  • EXAMPLE l4 Into a reaction flask was introduced 1,000 g. of chloropolyisobutene (polyisobutene of approximately 420 molecular weight chlorinated to approximately 8 weight percent chlorine), 270 ml. of ethylene diamine and 270 ml. of n-butanol. The mixture was heated gradually to 170 C. during 1 /2 hours; distillate was collected mainly between 130 and 160 C. The mixture was then heated for about 3 hours at 170 C. At the end of this time, 1,000 ml. of toluene and 250 ml. of methyl isobutyl carbinol were added and the mixture washed with dilute aqueous isopropyl alcohol, followed by repeated washings with water.
  • chloropolyisobutene polyisobutene of approximately 420 molecular weight chlorinated to approximately 8 weight percent chlorine
  • 270 ml. of ethylene diamine 270 ml. of ethylene diamine
  • the first test was the L-l Supp. 1 (MIL-L-2l04B, Supp. 1 Specifications).
  • the oil was formulated contain- 12 iug 0.03 weight percent nitrogen and 8 mM./kg. of 0,0- dialkyl phosphorodithioate (alkyl of from 4 to 6 carbon atoms) in a Mid-Continent SAE 30 base oil.
  • the test was carried out for 120 hours, the following table indicating the results.
  • Example 1 Example 1..- 4-0. 5-0-0 -0-75
  • Example 2 4-1-2-1 435--25
  • Base oil 3 38-18-10-10 8
  • 800-800-800 1 Measured on a rating of 0 to 100, 100 being completely filled.
  • 2 Measured on a rating of 0 to 800, 800 being completely black.
  • 3 Tested under the less severe L-l conditions (MIL-L-2104A).
  • compositions of this invention were tested under Caterpillar l-G conditions (MIL-L-45199).
  • MIL-L-45199 Caterpillar l-G conditions
  • To a Mid-Continent SAE 30 base oil was added the detergent and zinc 0 ,0- di(alkylphenyl) phosphorodithioate (the alkyl polypropylene of an average of 14 carbon atoms). The test was carried out for 60 hours. The following results were obtained.
  • the piston varnish is rated (rating of 0 to 10, no varnish being 10) and the total varnish is evaluated (rating of 0 to 50, no varnish being 50).
  • the above test was modified by increasing the time and periodically raising the oil sump temperature from F. to 205 F. and the water jacket temperature from 95 to F.
  • each candidate detergent was employed at concentrations to provide a constant weight percent of nitrogen; also included in the oil was 10 mM./kg. of zinc 0,0-di(alkyl) dithiophosphate (alkyl of from 4 to 6 carbon atoms) and 2 mM./ kg. of zinc 0,0-di(alkylphenyl) dithiophosphate (alkyl is polypropylene of from 12 to 15 carbon atoms).
  • concentrations to provide a constant weight percent of nitrogen; also included in the oil was 10 mM./kg. of zinc 0,0-di(alkyl) dithiophosphate (alkyl of from 4 to 6 carbon atoms) and 2 mM./ kg. of zinc 0,0-di(alkylphenyl) dithiophosphate (alkyl is polypropylene of from 12 to 15 carbon atoms).
  • the following table indicates the results obtained.
  • the engine is a Model 1-81 approximately 85 cc. displacement. The test is carried out for 10 hours, the engine being run at 7,000 r.p.m., at a temperature of 435 F. and with a wide open throttle. Using regular gasoline, at fuel-oil mixture in the ratio of 2021 is prepared, the oil composition being a blend of detergent in SAE 40 grade base oil, such that the finished oil contained 0.126 weight percent nitrogen.
  • the Yamaha engine test uses a 75 cc. Model YG-l motorcycle engine. The same conditions as described for the McCulloch engine are also used for the Hyundai engine.
  • port and valve deposits are rated on a scale of 0 (clean) to 10 (very heavy deposits) and valve deposit weights determined.
  • the remainder of the intake system is rated on a linear scale of 0 (clean) to 16 (deposit thick). Also, any stuck intake valves are observed and reported.
  • the harm test is carried out on a 1960 Chevrolet 6 cylinder engine. Starting with a clean cylinder head, intake system, pistons and new rings, the test is carried out for 200 hours under cyclic conditions. At the end of this time, the engine is disassembled and the parts are inspected.
  • the conditions under which the run is carried out are as follows: jacket temperature: 200 F.; oil temperature: 125 F.; cycle: idle at 600 r.p.m. of the time, low speed acceleration 20% of the time, high speed acceleration 13% of the time, and cruise at 1,400 r.p.m. 27 of TABLE IV.
  • Example 5 9. 2 360 500 250 5 8. 3 37. 0
  • Example 6. 9 7. 5 360 700 640 7 7. 8 30. 8 Base Oil 6. 4 360 580 610 10 6. 0 28. 7 Yamaha:
  • Example 5 7 8.6 360 640 620 12 6. 2 30. 2 Base 011 6. 0 360 700 750 15 l. 4 19. 6
  • compositions of this invention demonstrate the wide range of applicability of the compositions of this invention.
  • the excellent detergent and dispersant results are obtained under a wide variety of conditions in a wide variety of engines closely simulating extreme operating field conditions.
  • the compositions of this'in'vention are able to function in both lubricating oils and fuels effectively.
  • the compounds are readily available by simple synthetic methods, provide detergency without producing ash and either do not or only to an insignificant degree create deposits from their own decomposition products.
  • a gasoline composition having in an amount sufficient to provide detergency and dispersancy of from 100 to 1000 p.p.m. a composition of the formula:
  • a is an integer of from 1 to 3 and R is either polypropylene or polyisobutylene of from about 450 to 1,500 molecular weight.
  • a gasoline composition having from 100 to 1000 p.p.m. of a polyisobutenyl ethylene diamine wherein said polyisobutenyl is of from 450 to 1,500 molecular weight.
  • a fuel concentrate having from 10 to 70 weight percent of a polyisobutenyl ethylene diamine wherein said polyisobutenyl is of from about 450 to 1,500 molecular weight and the remainder is an aromatic hydrocarbon solvent, an alcohol, or mixtures thereof, boiling in the range of about 150 to 400 F.
  • a gasoline composition having from 100 to 1000 p.p.m. of a polm'sobutenyl diethylene triamine wherein said polyisobutenyl is of from 450 to 1,500 molecular weight.
  • a fuel concentrate having from 10 to Weight percent of a polyisobutenyl diethylene triamine wherein said polyisobutenyl is of from about 450 to 1,500 molecular weight and the remainder is an aromatic hydrocarbon solvent, an alcohol, or mixtures thereof, boiling in the range of about 150 to 400 F.
  • a gasoline composition having from to 1000 p.p.m. of a polyisobutenyl triethylene tetramine wherein said polyisobutenyl is of from 450 to 1,500 molecular weight.
  • a fuel concentrate having from 10 to 70 weight percent of a polyisobutenyl triethylene tetramine wherein said polyisobutenyl is of from about 450 to 1,500 molecular weight and the remainder is an aromatic hydrocarbon solvent, an alcohol, or mixtures thereof, boiling in the range of about to 400 F.
  • a gasoline composition having from 100 to 1000 p.p.m. of a polyisobutenyl tetraethylene pentamine wherein said polyisobutenyl is of from 450 to 1,500 molecular weight.
  • a fuel concentrate having from 10 to 70 weight percent of a polyisobutenyl tetraethylene pentamine wherein said polyisobutenyl is of from about 450 to 1,500 molecular weight and the remainder is an aromatic hydrocarbon solvent, an alcohol, or mixtures thereof, boiling in the range of about 150 to 400 F.

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FR2452081A1 (fr) * 1979-03-22 1980-10-17 Chevron Res Procede pour reduire l'encrassement d'un echangeur de chaleur
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US5455358A (en) * 1992-02-10 1995-10-03 Chevron U.S.A. Inc. Fuel compositions containing alkyl-substituted cyclic urea-substituted amines
US5457211A (en) * 1992-02-10 1995-10-10 Chevron U.S.A. Inc. Hydroxyalkyl-substituted cyclic urea-substituted amines
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US5489315A (en) * 1994-09-19 1996-02-06 Shell Oil Company Fuel compositions comprising hydantoin-containing polyether alcohol additives
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Publication number Publication date
DE1545487B2 (de) 1980-02-14
JPS4945685B1 (enrdf_load_stackoverflow) 1974-12-05
US3438757A (en) 1969-04-15
BE744693Q (fr) 1970-07-01
DE1545487C3 (de) 1980-10-16
DE1289355B (de) 1975-06-12
GB1083610A (en) 1967-09-20
FR1489559A (fr) 1967-07-21
FR1492000A (fr) 1967-08-11
US3565804A (en) 1971-02-23
DE1545487A1 (de) 1970-07-02
MY7000109A (en) 1970-12-31
DE1289355C2 (de) 1975-06-12
GB1094020A (en) 1967-12-06

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