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Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene

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US3316177A
US3316177A US41661864A US3316177A US 3316177 A US3316177 A US 3316177A US 41661864 A US41661864 A US 41661864A US 3316177 A US3316177 A US 3316177A
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interpolymer
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Jr Casper J Dorer
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Lubrizol Corp
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/44Preparation of metal salts or ammonium salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/234Macromolecular compounds
    • C10L1/236Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2800/00Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/10Copolymer characterised by the proportions of the comonomers expressed as molar percentages
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086Imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28Amides; Imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound

Description

United States Patent Ofiice 3,3 l hi 7? Patented Apr. 25, 1967 3,316,177 FUNCTIUNAL FLUID CONTAINING A SLUDGE of Ohio No Drawing. Filed Dec. 7, 1964, Ser. No. 416,618

9 Claims. (Cl. 25251.5)

This invention relates to a novel composition of matter. In a more particular sense it relates to a nitrogen-containing composition which is useful as an additive in fuels, lubricants, petroleum fractions, etc. The nitrogencontaining composition of this invention is especially effective as an additive to inhibit the formation of harmful deposits in hydrocarbon compositions such as petroleum refinery fractions.

Most of the gasoline produced today is obtained by the thermal or catalytic cracking of heavier petroleum hydrocarbon feed stocks such as light or heavy gas oils, cycle stocks, virgin or topped crude oils, lube stocks, kerosene, and kerosene-gas oil mixtures. A number of different thermal and/or catalytic cracking processes known in the petroleum industry under designations such as Fluid Process, Thermofor, Houdry, Platforming, Thermal Reforming, Viscosity-Breaking, etc., are employed for the purpose. Although these various processes differ considerably as to the precise manner in which the heavier hydorcarbon molecules are cracked to yield gasoline, they all involve the heating of the hydrocarbon feed stock to a high temperature (370-1200- F.) and the passage of such heated stock, optionally mixed with a cracking catalyst, through heated tubes, reactors, convertors, and tower stills.

Regardless of the particular process used, the cracking operation always results in the formation of some undesirable carbonaceous material or refinery coke which adheres to the tubes, reactors, etc., of the cracking unit and lowers its efliciency, principally by impeding the flow of the feed stock therethrough and the transfer of heat to or from such stock. After enough carbonaceuos material has accumulated on the various parts of the cracking unit to lower its efficiency substantially, the unit must be dismantled, cleaned, and reassembled. Of course, such cleaning operations are not only tedious and costly, but result in a large proportion of down-time during which the unit is not functioning. Although the use of modern Platforming and catalytic creacking processes has reduced the amount of down-time as compared with older, strictly thermal cracking processes, the accumulation of refinery coke still presents a problem to the petroleum refining industry.

It is accordingly a principal object of this invention to provide novel compositions of matter.

object of this invention to provide addit1ves in fuels, lubricants, petroleum fractions and other hydrocarbon compositions.

It is another object of this invention to provide improved fuels, lubricants and hydrocarbon compositions.

It is another object of this invention to inhibit the formation of harmful deposits in refinery cracking units.

It is another object of this invention to inhibit the accumulation of harmful deposits in hydrocarbon compositions which are subjected to high temperature and pres sure.

It is another object of this invention to inhibit the formation of harmful deposits in heat exchange units.

These and other objects are attained in accordance Cleveland, Ohio, assignor to The with this invention 'by providing a nitrogen-containing composition prepared by the process comprising reacting an oxidized, degraded interpolymer of propylene and ethylene having a molecular weight of at least about 1000 with from about 1% to about 20% by weight of maleic anhydride to form an acidic intermediate and neutralizing said acidic intermediate with an alkylene polyamine.

The acidic composition, described above as the acidic intermediate, is useful as an intermediate for preparing other compositions, e.g., metal salts including those of zinc and barium, which are likewise useful as improvement agents for lubricating compositions.

The oxidized, degraded interpolymers useful in the above process are derived principally from ethylene and propylene. They may include minor amounts, i.e., up to about 10% based on the molar amounts of monomeric ethylene and propylene units in the interpolymer, of polymerized units derived from other monomers. EX- amples of such other monomers include polymeriza'ble monolefins having at least 4 carbon atoms such as lbutene, l-pentene, Z-butene, 3-hexene, 4-methyl-11pentene, l-decene, l-nonene, 2-methyl-propene and l-dodecene. They include also polyenes, i.e., those having 2 or more olefinic linkages, such as conjugated polyenes, for example, butadiene, isoprene, piperylene, 1,3-hexadiene, 1,3-octadiene, 2,4-decadiene, etc, They may further be non-conjugated polymers such as 3,3-dirnethyl- 1,5-hexadiene, 1,9-decadiene, di-cyclopentadiene, 1,19- eicosadiene, 1,4-pentadiene, 1,5-hexadiene, etc. The latter non-conjugated dienes are especially useful in the interpolymer. For the most part, such other monomers preferably contain from 4 to about 10 carbon atoms although they may contain as many as 25 carbon atoms.

The interpolymers containing from about 20% to about (molar) of polymerized propylene, from about 30% to about of polymerized ethylene, and up to about 10% of another polymerized olefin are useful and those containing from about 25% to about 50% of polymerized propylene, from about 50% to about 75 of polymerized ethylene and from about 1% to about 10% of a polymerized non-conjugated diene are preferred.

The interpolymers from which the oxidized, degraded interpolymers of the above process are derived usually have molecular weights of at least about 50,000. They may have molecular weights of as high as 800,000 or higher. The interpolymers having molecular weights ranging from about 80,000 to about 600,000 are especially useful.

The oxidized, degraded interpolymers of this invention are prepared most conveniently by heating an interpolymer illustrated above at a temperature of at least about C. in the presence of oxygen or air so as to cause the degradation of the interpolymer. Such degradation is usually characterized by a. substantial reduction of the molecular weight of the interpolymer. The mechanism by which the interpolymer is degraded is not precisely known; nor is the chemical composition of the oxidized, degraded product. It is known, however, that 'an oxidized, degraded interpolymer having a molecular weight of at least about 1000 is useful in the process of this invention and so also is one which has been oxidized and degraded to the extent that its molecular weight is at least about 5% less than the molecular weight of the interpolymer before degradation. The oxidized, degraded interpolymer having a molecular weight of from about 3000 to about 5000 or as high as about 200,000 is preferred for use in the process of this invention.

A particularly useful method of preparing the oxidized and degraded interpolymer involves heating a fluid solution of a suitable interpolymer in an inert solvent and J2 )ubbling oxygen or air through the solution at a tempera- :ure of at least about 100 C. until the desired degradation is achieved. In lieu of oxygen or air, any mixture of oxygen and inert gas such as nitrogen or carbon dioxide may be used. The inert gas thus functions as a carrier of oxygen and often provides a convenient means if introducing oxygen into the reaction mixture.

The inert solvent useful in preparing the fluid solution of the interpolymer reactant is preferably a liquid inert hydrocarbon such as naphtha, hexene, cyclohexane, dodecane, biphenyl, xylene or toluene. It may be a polar solvent such as diphenyl oxide. The amount of the solvent to be used is not critical so long as .a sufficient amount is used to result in the fluid solution of the interpolymer. Such solution usually contains from about 60 to 95% of a solvent.

The temperature at which the interpolymer is oxidized and degraded is at least about 100 0, preferably at least about 150 C. and it may be as high as 250 C., 300 C. or even higher.

The alkylene polyamine useful in the process of this invention conforms for the most part to the structural formula:

H N alkylene-NH H wherein x has a value from 1 to about 12 and the alkylene radical may contain from 2 to about 12 carbon atoms and is preferably a lower alkylene radical, i.e., one having up to about 6 carbon atoms. Thus the alkylene polyamine may be ethylene diamine, diethylene, triamine, triethylene tetramine, tetraethylene pentamine, trimethylene diamine, N,N-dimethyl(trimethylenediamine), bis(dimethy1aminopropyl)amine, propylene diamine, tetramethylene diamine, tbutylene diamine, N-aminoethyl trimethylene diamine, N-dodecyl propylene diamine, di-(trimethylene) triamine, pentaethylene hexamine, etc. It includes also higher and cyclic homologues of such amines such as piperazines. The ethylene polyamines are especially useful. They are discussed in some detail under the heading Ethylene Amines in Encyclopedia of Chemical Technology Kirk and Othmer, volume 5, pages 898-805, Interscience Publishers, New York (1950). Such compounds are prepared most conveniently by the reaction of an alkylene dihalide, e.g., ethylene dichloride, with ammonia or a primary amine. This reaction results in the production of somewhat complex mixtures of alkylene polyamines including cyclic condensation products such as piperazine, N-aminoethyl-piperazine, etc. These mixtures find use in the process of this invention. On the other hand, quite satisfactory products may be obtained also by the use of pure alkylene amines. An especially useful alkylene polyamine for reasons of economy as well as effectiveness of the products derived therefrom is a mixture of ethylene polyaniines prepared by the reaction of ethylene chloride and ammonia and having an average of from 2 to 7 amino groups per molecule.

The process by which the nitrogen-containing composition of this invention is prepared usually involves heating the oxidized, degraded interpolymer with from about 1% to about 20%, preferably from 2% to about 10% (by weight), of maleic anhydride at a temperature of at least about 80 0., preferably from about 100 C. to 250 C., to form an acidic intermediate and then neutralizing the acidic intermediate :by mixing it with the alkylene polyamine reactant at a temperature of at least about 25 0, preferably from about 80 C. to about 250 C. A higher temperature may be used in the process provided that it does not exceed the decomposition point of the reaction mixture.

The process may be carried out in the presence of a solvent such as xylene, benzene, naphtha, chlorobenzene, nitrobenzene, or diphenyl ether. Mineral oil is especially useful as the solvent. The use of a solvent is particularly advantageous in cases where one of the reactants is a viscous liquid or a solid; the solvent in such cases functions to facilitate the mixing of the reactants and the control of the reaction temperature.

The chemical composition of the acidic intermediate or the product, i.e., the nitrogen-containing composition, of the above process is not fully understood. The acidic intermediate is believed to be either a substituted maleic anhydride or a substiuted succinic anhydride or a mixture thereof. The manner in which the anhydride radical is combined with the interpolymer portion of the molecule is not known; nor is it known whether one or more anhydride radicals are combined with a particular interpolymer chain. It is known, however, that the reaction product of the interpolymer and maleic anhydride is acidic and is neutralized by the alkylene amine reactant in the above process to form the desired product. In this regard it is noted that the amount of the alkylene polyamine reactant to be used in the process depends to a large extent on the acidity of the acidic intermediate, that is, the amount of the alkylene polyamine reactant to be used in the process is chemically equivalent to the acidic intermediate. However, from about 0.8 equivalent to about 2 or more equivalents of the alkylene polyamine per equivalent of the acidic intermediate may be used. The equivalent weight of an amine depends on the number of amino groups in a molecule. has 3 equivalents per mole.

The chemical composition of the product, i.e., the nitrogen-containing composition, of the above process is not fully understood. It depends to some extent upon the temperature at which the product is formed. For instance, where the reaction of the acidic intermediate and the alkylene amine is carried out at a temperature below about C., the product will contain a substantial quantity of an amine salt whereas if such reaction is carried out at a temperature above about C., the product will contain a substantial quantity of an imide, amide or amidine. In .most instances, the product will be a complex mixture, the precise composition of which is not known. It is known, however, that the product, regardless of the relative proportions of its components, is useful for the purposes of this invention.

The following examples illustrate the preparation of the nitrogen-containing compositions of this invention.

Example 1 Tetrachloroethylene (31.) is passed through a silica gel column, sparged with nitrogen and then added under nitrogen to a dry reaction flask at 25 C. Agitation is begun and an equirnolar mixture of gaseous ethylene and propylene is introduced below the tetrachloroethylene liquid surface at a rate of .100 ml. per second until a saturated monomer solution is obtained, the excess of gas being allowed to escape through a gas outlet tube. To this saturated monomer solution there is added 8 ml. (0.0128 mole) of a 1.6 molar solution of aluminum triisobutyl in cyclohexane and 0.94 ml. (0.010 mole) of vanadyl trichloride, separately and rapidly in turn, by means of syringes, through an opening in the reactor sealed with a soft rubber cap. The tetrachloroethylene solution turns to a clear amber color and the temperature rises to about 40 C. after a minute. To the agitated reaction mixture at 35 40 C., an equimolar mixture of gaseous ethylene and propylene is introduced at a rate of 100 ml. per second over a period of 0.5 hours. To the reaction mixture there is added 5 ml. of n-butanol and the polymer separates as a rubbery swollen solid which is squeezed free of excess solvent, washed several times with fresh n-butanol, and dried. The copolymer thereby obtained has a propylene content of 20 mole percent and a molecular weight of 250,000. This copolymer is then dissolved in four times its weight of diphenyl oxide and blown with oxygen at a temperature of 150180 C. for 6 hours. The oxidized, degraded polymer is found to have a molecular weight of 5000. A portion of the oxidized, degraded polymer in diphenyl oxide is mixed with For instance, diethylene triarnine 1% (by weight of the polymer) of maleic anhydride and the mixture is heated at 200 C. for 3 hours to form an acidic product. The acidic product is then neutralized with a stoichiometric amounts of ethylene diamine at 120150 C. The reaction mixture is dissolved in SAE 20 mineral oil and is heated at 120-l50 C./1 mm. to distill off volatile components. The residue is an oil solution of the nitrogen-containing product.

Example 2 A solution of 30 grams (0.15 mole) of aluminum triisobutyl and 84 grams (0.6 mole) of decene-l in 200 ml. of tetrachloroethylene was heated at reflux under a nitrogen atmosphere for 2 hours to form aluminum tridecyl. The solution was cooled to room temperature and blended with 1800 ml. of tetrachloroethylene, presaturated with an ethylene-propylene gas mixture containing 75 mole percent of propylene. The ethylenepropylene gas mixture (75 mole percent propylene) is fed into the tetrachloroethylene solution at a rate 37.5 ml. per second. Introduction of ethylene and propylene is continued as a solution of 4.35 grams (0.025 mole) of ml. of tetrachloroethylene is added to the reaction mixture with vigorous stirring at 29 -41 C. over a period of 2 minutes. The catalyst forms a clear violet solution and rapid absorption of the gas feed commences. Thereafter, 30 ml. (0.108 mole) of a 3.6 molar solution of 1,4-hexadiene in tetrachloroethylene is added over a period of 9 minutes to the reaction mixture at 41-48 C. The feed of ethylene and propylene is continued and 53.4 ml. (0.192 mole) more of the 3.6 molar, 1,4-hexadiene solution is added to the reaction mixture over a period of 2 hours at 3840 C. Then, 6 l. of n-butanol are added to the reaction mixture causing precipitation of an interpolymer. The precipitate is slurried with acetone in a Waring Blendor and then dried on a rubber mill at 50 C. The produce (97 grams) is a soft, rubbery terpolymer which has a propylene content of 42 mole percent, a diene content of 1.2 mole per- The terpolymer has an RSV of about 2.1, corresponding to a molecular weight of 125,500 (RSV is an abbreviation of reduced specific viscosity which means the specific viscosity, corrected to shear gradient divided by the concentration of the polymer solution in grams per 100 ml. In actual measurement, the viscosity is that of a decalin solution, at 135 C., of the polymer at a concentration of 0.1 gram in 100 ml. of the solution. The molecular weight of the polymer is calculated according to the equation l'.SV=AM where M is the molecular weight, A and x are specific constants characteristic of the polymer, Kirk and Othmer, Encyclopedia of Chemical Technology, (2nd Supp. 1960 at 663) and Gaylord and Mark, Linear and Stearyl Regular Addition Polymers, page 79 (1959). A soultion of 500 grams of this interpolynier in 2000 grams of diphenyl oxide is blown with oxygen at 200225 C. for 4 hours. oxidized, degraded polymer solution (1830 grams) is mixed with maleic anhydride (41 grams) at 230 C. for 4 hours and then heated at 200 C./1 mm. to remove volatile components. The residue, 383 grams, is mixed with 383 grams of xylene and the xylene solution has an acid number of 22. A portion of this solution (100 grams) in 100 grams of mineral oil is neutralized with twice the stoichiometric amount of N,N-dimethyl trimethylenediamine at 90-170 C. whereupon water formed during the reaction is distilled off. The residue is heated to 170 C./45 mm. and filtered. The filtrate is a 65.3% oil solution of the nitrogen-containing product having a nitrogen content of 0.5.)

Example 3 A product is obtained by a procedure essentially the same as that of Example 2 from these reactants: the oxidized, degraded interpolymer of Example 2, maleic anhydride (10% by weight of the polymer), a mixture of N,N-dimethyl trimethylenediamine and a commercial polyethylene polyamine mixture having an average of 5 amino groups per molecule in a weight ratio of 9:1 (twice the stoichiometric amount. of the polymermaleic anhydride reaction product). The product is dissolved in mineral oil and a 65% oil solution of the product has a nitrogen content of 0.55%.

Example 4 dized, degraded interpolyrner of Example 2, maleic anhydride (5% by weight of the polymer), and N,N-di methyl trimethylenediamine (twice the equivalent amount of the polymer-maleic anhydride reaction product). The product is dissolved in mineral oil and a 66% oil solution of the product has a nitrogen content of 0.37%.

Example 5 (2% by weight of the polymer), and bis-(dimethylaminopropyl)amine (twice the stoichiometric amount of the polymer-maleic anhydride reaction product). The product is dissolved in mineral oil and a 62% oil solution of the product has a nitrogen content of 1.27%.

Example 6 hydride (4.4% by weight of the polymer), and a commercial polyethylene polyamine mixture having an average of 5 amino groups per molecule (1 equivalent per equivalent of the polymer-maleic anhydride reaction product).

The nitrogen-containing products of this invention are useful as additives in fuels, lubricant compositions and hydrocarbon oils. They are effective to impart sludge inhibiting properties and detergent properties to such compositions. They are especially useful as an additive in refinery streams which are subjected to high temperature cracking, distillation, reforming or similar operations.

cumulation of carbonaceous material which tend to be produced at high temperatures. Thus, the nitrogen-containing products of this invention have found particular animal, vegetable, lubricating oils are preferred of their availability, general excellence, and low cost. For certain applications, oils belonging to one of the other hree groups may be preferred. The concentration of the .itrogen-containing products of this invention in a lubrizating composition may range from about 0.1% to about more often from about 0.5% to by weight.

The liquid hydrocarbon fuels in which the nitrogen- :ontaining compositions of this invention are useful in- :lude gasoline, diesel fuels and other distillate or residual JllIIlCl" fuel oils which are derived from petroleum by such nethods as distillation, thermal cracking or catalytic cracking. For the most part the burner fuel oil and diesel fuel have a minimum flash point of 80 F, maximum pour point of 70 F., maximum point of 650 F, maximum 90% point of 900 F., minimum API gravity of 24 and a maximum viscosity value of 130 Saybolt Universal Seconds at 100 F. The concentration of the nitrogen-containin g products of this invention in such fuels may range from about 0.0001% to about 5% more often from 0.001% to about 2%, by weight.

A unique characteristic of the nitrogen-containing compositions of this invention is their effectiveness under high temperature conditions such as 300-1200 F. to impart sludge inhibiting and detergent properties to fuels, lubricants, oils and petroleum fractions. This effectiveness is directly related to the oxidized, degraded interpolymer from which the compositions are derived. The manner in which such interpolymer imparts the high temperature effectiveness to the compositions of this invention is not fully understood. it is believed, however, that the oxidation and degradation of the interpolymer results in a polymeric product which is highly resistant to further oxidative and thermal degradation and that such resistance is imparted to the nitrogen-containing compositions of this invention. A critical element of the present invention, therefore, is the use of the oxidized, degraded interpolymer in the process for preparing the nitrogencontaining compositions which are useful for the herein described purposes.

The effectiveness of the nitrogen-containing products of this invention as additives in lubricating compositions is shown by the results of an Oxidation-Dispersancy test. In this test a 350 cc. sample of a lubricant containing the additive to be tested is heated at 300 F. for 144 hours in a 2" x borosilicate tube. The lubricant base employed in the test is a Mid-Continent conventionally refined mineral oil having a viscosity of about 200 Saybolt Universal Seconds at 100 F. Air is bubbled through the lubricant at a rate of 10 l. per hour. The oxidized sample is allowed to cool to 122 F. and to stand for 15 hours at room temperature and then filtered through No. 1 Whatman paper (double thickness) under slightly reduced pressure. The sludge deposit formed during the test is collected on the filter paper, washed with naphtha to a constant weight and reported as milligrams of sludge per 100 cc. of oil. The smaller the amount of the sludge deposit the more effective the detergent additive. The results are shown in Table I below:

TABLE I.OXIDATION-DETERGENCY TEST Additive Tested (1.5% by weight of the of sludge/100 m1. of sample D 0:: Product oi Example 4...

The effectiveness of the nitrogen-containing products of this invention as an additive in fuel oils is shown by the results (Table 11) of the Fuel Oil Detergcncy test. In this test, a mixture of 4 l. of a catalytically cracked No. 2 light fuel oil and 15 grams of a synthetic sludge (prepared by homogenizing a 50/40/10, by weight, mixture of distilled Water/No. 2 uninhibited fuel oil/ carbon black) is circulated for 2 hours in a fuel oil burner pump equipped with a 100-mesh Monel strainer. The sludge retained on the strainer is washed with acetone and weighed.

(7 r.) of the additive is indicated by the perthe sludge retained on the strainer as compared to the sludge formed from the fuel oil containing no additive. A fuel whose rating is greater than 5 90% is considered to have excellent anti-clogging properties.

TABLE II.FUEL OIL DETERGENCY TEST The effectiveness cent reduction of Test Results Milligrams of Sludge Additive Tested (0.005% by f 10 weight in the test sample) With Without Percent Additive Additive Reduction Product of Example 2 111.7 689 83. 8 Product of Example 4 108. 6 746 85. 4

What is claimed is:

1. A petroleum fraction containing a minor amount, sufficient to impart sludge-inhibiting and detergent properties to said petroleum fraction, of a nitrogen-containing composition prepared by the process comprising reacting an oxidized, degraded interpolymer of propylene and ethylene, said oxidized, degraded interpolymer having a molecular weight of tained by heating said interpolymer at a temperature of at least about 100 C. in the presence of oxygen to cause a substantial reduction in the molecular weight of said interpolyrner, with from about 1% to about by weight of maleic anhydride to form an acidic intermediate and neutralizing said acidic intermediate with an alkylene polyamine.

2. A petroleum fraction containing a minor amount, sufficient to impart sludge-inhibiting and detergent properties to said petroleum fraction, of a nitrogen-containing composition prepared by the process which comprises reacting an oxidized, degraded interpolymer of propylene, ethylene, and a non-conjugated diene having from 4 to about 10 carbon atoms in proportions of from about 20 to about 70 mole percent of propylene, from about 30 to about 80 mole percent of ethylene, and from about 1 to about 10 mole percent of the diene, said oxidized, degraded interpolymer having a molecular weight of from about 1000 to about 5000 and being obtained by heating said interpolymer at a temperature of at least about 100 C. in the presence of oxygen to cause a substantial reduction in the molecular weight of said interpolymer, 'with from about 1% to about 20% by weight of maleic anhydride to form an acidic intermediate and neutralizing said acidic intermediate with from about 1 to about 2 equivalents of an alkylene polyamine having from 2 to about 7 amino groups.

3. The petroleum fraction of claim 2 wherein the alkylene polyamine is a polypropylene polyamine.

4. A hydrocarbon oil containing a minor amount, sulficient to impart sludge-inhibiting and detergent properties thereto, of a nitrogen containing composition prepared by the process comprising reacting an oxidized, degraded interpolymer of propylene and ethylene, said oxidized, degraded interpolymer having a molecular weight of at least about 1000 and being obtained by heating said interpolymer at a temperature of at least about 100 C. in the presence of oxygen to cause a substantial reduction in the molecular weight of said interpolymer, with from about 1% to about 20% by weight of maleic anhydride to form an acidic intermediate and neutralizing said acidic intermediate with an alkylene polyamine.

5. A hydrocarbon oil containing a minor amount, sufficient to impart sludge-inhibiting and detergent properties thereto, of a nitrogen-containing com-position prepared by the process which comprises reacting an oxidized, degraded interpolymer of propylene, ethylene, and a nonconjugated diene having from 4 to about 10 carbon atoms in proportions of from about 20 to about 70 mole percent of propylene, from about 30 to about 80 mole percent of ethylene, and from about 1 to about 10 mole percent of the diene, said oxidized, degraded interpolymer having a at least about 1000 and being obmolecular weight of from about 1000 to about 5000 and being obtained by heating said interpolymer at a temperature of at least about 100 C. in the presence of oxygen to cause a substantial reduction in the molecular weight of said interpolymer, with from about 1% to about 20% by weight of maleic anhydride to form an acidic intermediate and neutralizing said acidic intermediate with from about 1 to about 2 equivalents of an alkylene polyamine having from 2 to about 7 amino groups.

6. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sulficient to impart sludge-inhibiting and detergent properties thereto, of a nitrogen-containing composition prepared by the process comprising reacting an oxidized, degraded interpolymer of propylene and ethylene, said oxidized, degraded interpolymer having a molecular weight of at least about 1000 and being obtained by heating said interpolymer at a temperature of at least about 100 C. in the presence of oxygen to cause a substantial reduction in the molecular weight of said interpolymer, with from about 1% to about 20% by weight of maleic anhydride to form an acidic intermediate and neutralizing said acidic intermediate With an alkylene polyamine.

7. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufiicient to impart sludge-inhibiting and detergent properties thereto, of a nitrogen-containing composition prepared by the process which comprises reacting an oxidized, degraded interpolymer of propylene, ethylene, and a nonconjugated dicne having from 4 to about 10 carbon atoms in proportions of from about to about 70 mole percent ture of at least about 100 C. in the presence of oxygen to cause a substantial reduction in the molecular weight of said interpolymer, with from about 1% to about 20% by Weight of maleic anhydride to form an acidic intermediate and neutralizing said acidic intermediate with from about 1 to about 2 equivalents of an alkylene polyamine having from 2 to about 7 amino groups.

8. A liquid hydrocarbon fuel containing a minor amount, sufiicient to impart sludge-inhibiting and detergent properties thereto, of a nitrogen containing composition prepared by the process comprising reacting an oxidized, degraded interpolymer of propylene and ethylene, said oxidized, degraded inter-polymer having a molecular Weight of at least about 1000 and being obtained by heat ing said inter-polymer at a temperature of at least about 100 C. in the presence of oxygen to cause a substantial reduction in the molecular weight of said interpolymer, With from about 1% to about 20% by Weight of maleic anhydride to form an acidic intermediate and neutralizing said acidic intermediate with an alkylene polyamine.

9. A liquid hydrocarbon fuel containing a minor amount, sufficient to impart sludge-inhibiting and detergent properties thereto, of a nitrogen-containing composition prepared by the process which comprises reacting an oxidized, degraded interpolymer of propylene, ethylene, and a non-conjugated diene having from 4 to about 10 carbon atoms in proportions of from about 20 to about 5000 and being obtained by heating said interpolymer at a temperature of at least about C. in the presence of oxygen to cause a substantial reduction in the molecular Weight of said interpolymer, With from about 1% to about by Weight of maleic anhydride References Cited by the Examiner W. H. CANNON, Assistant Examiner.

Claims (1)

  1. 6. A LUBRICATING COMPOSITION COMPRISING A MAJOR PROPORTION OF A LUBRICATING OIL AND A MINOR PROPORTION, SUFFICIENT TO IMPART SLUDGE-INHIBITING AND DETERGENT PROPERTIES THERETO, OF A NITROGEN-CONTAINING COMPOSITION PREPARED BY THE PROCESS COMPRISING REACTING AN OXIDIZED, DEGRADED INTERPOLYMER OF PROPYLENE AND ETHYLENE, SAID OXIDIZED, DEGRADED INTERPOLYMER HAVING A MOLECULAR WEIGHT OF AT LEAST ABOUT 1000 AND BEING OBTAINED BY HEATING SAID INTERPOLYMER AT A TEMPERATURE OF AT LEAST ABOUT 100*C. IN THE PRESENCE OF OXYGEN TO CAUSE A SUBSTANTIAL REDUCTION IN THE MOLECULAR WEIGHT OF SAID INTERPOLYMER, WITH FROM ABOUT 1% TO ABOUT 20% BY WEIGHT OF MALEIC ANHYDRIDE TO FROM AN ACIDIC INTERMEDIATE AND NEUTRALIZING SAID ACIDIC INTERMEDIATE WITH AN ALKYLENE POLYAMINE.
US3316177A 1964-12-07 1964-12-07 Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene Expired - Lifetime US3316177A (en)

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