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Definitions

• This invention is directed to novel fuel compositions for internal combustion engines and to methods for using such fuel compositions.
• fuels used in internal combustion engines have contained various kinds of additives to improve performance of the fuel or to alleviate problems arising during the use and combustion of fuels in internal combustion engines.
• engine designers generally focused their efforts towards the development of high-performance engines, with little concern about fuel economy or exhaust emissions.
• the fuel delivery system for engines of this era involved the use of carburetors to deliver an air-fuel mixture, via a manifold, to the cylinders for combustion.
• Primary concerns at this time were carburetor icing, adequate octane value, deposit formation on carburetor surfaces, and fuel stability.
• Additives for fuels such as anti-icing agents, lead-containing fuel additives, detergents, and various antioxidants generally resulted in adequate performance.
• US-A-4,663,063 discloses a composition for use as an additive in a two-cycle engine which comprises an amino compound which is not an amino phenol optionally in combination with a further amino compound which may be an amino phenol. However, it is an essential feature of this composition that an alkyl phenol is present.
• a motor fuel composition comprising a normally liquid fuel in the gasoline boiling range
• components (A) and (B) are present in amounts sufficient to provide total intake system cleanliness. In another embodiment, components (A) and (B) are present in amounts sufficient to prevent or to reduce the formation of intake valve deposits or to remove same where they have formed.
• an additional component (C) a fluidizer oil, has been found to be helpful in providing enhanced detergency and in reducing valve-sticking. Methods for providing total intake system cleanliness and preventing or reducing the formation of intake valve deposits or removing same, are disclosed.
• the aromatic moiety, Ar, of Formula I can be a single aromatic nucleus such as a benzene nucleus, a pyridine nucleus, a thiophene nucleus, or a 1,2,3,4-tetrahydronaphthalene nucleus, or a polynuclear aromatic moiety.
• Such polynuclear moieties can be of the fused type; that is, wherein at least one aromatic nucleus is fused at two points to another nucleus such as is found in naphthalene, anthracene or the azanaphthalenes.
• such polynuclear aromatic moieties can be of the linked type wherein at least two nuclei (either mono- or polynuclear) are linked through bridging linkages to each other.
• bridging linkages can be chosen from carbon-to-carbon single bonds, ether linkages, keto linkages, sulfide linkages, polysulfide linkages of 2 to 6 sulfur atoms, sulfinyl linkages, sulfonyl linkages, methylene linkages, alkylene linkages, di-(lower alkyl)methylene linkages, lower alkylene ether linkages, alkylene keto linkages, lower alkylene sulfur linkages, lower alkylene polysulfide linkages of 2 to 6 carbon atoms, amino linkages, polyamino linkages and mixtures of such divalent bridging linkages.
• more than one bridging linkage can be present in Ar between aromatic nuclei.
• a fluorene nucleus has two benzene nuclei linked by both a methylene linkage and a covalent bond.
• Such a nucleus may be considered to have 3 nuclei but only two of them are aromatic.
• Ar will contain only carbon atoms in the aromatic nuclei per se (plus any lower alkyl or alkoxy substituent present).
• the number of aromatic nuclei, single, fused, linked or both, in Ar can play a role in determining the integer values of a, b and c in Formula I.
• a, b and c are each independently 1 to 4.
• a, b and c can each be an integer of 1 to 8.
• a, b and c can each be an integer of 1 to 12.
• Ar is a biphenyl or a naphthyl moiety
• a, b and c can each independently be an integer of 1 to 8.
• the values of a, b and c are obviously limited by the fact that their sum cannot exceed the total unsatisfied valences of Ar.
• the single ring aromatic nucleus which can be the Ar moiety can be represented by the general formula ar(Q) m wherein ar represents a single ring aromatic nucleus (e.g., benzene) of 4 to 10 carbons, each Q independently represents a lower alkyl group, lower alkoxy group, nitro group, nitroso group, carboxy lower alkyl group or halogen atom, and m is 0 to 3.
• ar represents a single ring aromatic nucleus (e.g., benzene) of 4 to 10 carbons
• each Q independently represents a lower alkyl group, lower alkoxy group, nitro group, nitroso group, carboxy lower alkyl group or halogen atom
• m is 0 to 3.
• "lower” refers to groups having 7 or less carbon atoms such as lower alkyl and lower alkoxyl groups.
• Halogen atoms include fluorine, chlorine, bromine and iodine atoms; usually, the hal
• single ring Ar moieties are the following: etc., wherein Me is methyl, Et is ethyl, Pr is n-propyl, and Nit is nitro.
• Ar is a polynuclear fused-ring aromatic moiety, it can be represented by the general formula wherein ar, Q and m are as defined hereinabove, m' is 1 to 4 and represents a pair of fusing bonds fusing two rings so as to make two carbon atoms part of the rings of each of two adjacent rings.
• fused ring aromatic moieties Ar are: etc.
• Ar is a linked polynuclear aromatic moiety
• w is an integer of 1 to 20
• ar is as described above with the proviso that there are at least 3 unsatisfied (i.e., free) valences in the total of ar groups
• Q and m are as defined hereinbefore
• each Lng is a bridging linkage individually chosen from carbon-to-carbon single bonds, ether linkages (e.g.
• keto linkages e.g., sulfide linkages (e.g., -S-), polysulfide linkages of 2 to 6 sulfur atoms (e.g., -S2-6-), sulfinyl linkages (e.g., -S(O)-), sulfonyl linkages (e.g., -S(O)2-), lower alkylene linkages (e.g., -CH2-, -CH2-CH2-, etc.), di(lower alkyl)-methylene linkages (e.g., CR°2-), lower alkylene ether linkages (e.g., -CH2O-, -CH2O-CH2-, -CH2-CH2O-, -CH2CH2OCH2CH2-, etc.), lower alkylene sulfide linkages (e.g., wherein one or more -O-'s in the lower alkylene ether linkages is replaced with an -
• linked moieties are: etc.
• the Ar moiety is normally a benzene nucleus, lower alkylene bridged benzene nucleus, or a naphthalene nucleus.
• a typical Ar moiety is a benzene or naphthalene nucleus having 3 to 5 unsatisfied valences, so that one or two of said valences may be satisfied by a hydroxyl group with the remaining unsatisfied valences being, insofar as possible, either ortho or para to a hydroxyl group.
• Ar is a benzene nucleus having at least 3 unsatisfied valences so that one can be satisfied by a hydroxyl group with the remaining 2 or 3 being either ortho or para to the hydroxyl group.
• the aminophenols of the present invention contain, directly bonded to the aromatic moiety Ar, at least one group A, which, independently, may be H or a hydrocarbyl group.
• each group A is independently H or an alkyl or alkenyl group having up to about 18 carbon atoms.
• at least one A is a hydrocarbyl group. More than one hydrocarbyl group can be present, but usually no more than two or three hydrocarbyl groups are present for each aromatic nucleus in the aromatic moiety Ar.
• at least one A group is a hydrocarbyl group containing from 9 to 750 carbons.
• the hydrocarbyl group A has at least 30 to 400 carbon atoms, more typically, at least 50 carbon atoms and up to 750, more typically, up to 300 carbon atoms.
• each non-hydrogen A is an aliphatic hydrocarbyl group.
• the group A is an alkyl or alkenyl group having from 2 to 28 carbon atoms, it is typically derived from the corresponding olefin; for example, a butyl group is derived from butene, an octyl group is derived from octene, etc.
• A when A is a hydrocarbyl group having at least about 30 carbon atoms, it is frequently an aliphatic group made from homo- or interpolymers (e.g., copolymers, terpolymers) of mono- and di-olefins having 2 to 10 carbon atoms, such as ethylene, propylene, butene-1, isobutene, butadiene, isoprene, 1-hexene or 1-octene. Typically, these olefins are 1-mono olefins such as homopolymers of ethylene.
• aliphatic hydrocarbyl groups may also be derived from halogenated (e.g., chlorinated or brominated) analogs of such homo- or interpolymers.
• a groups which are hydrocarbyl can, however, be derived from other sources, such as monomeric high molecular weight alkenes (e.g., 1-tetracontene) and chlorinated analogs and hydrochlorinated analogs thereof, aliphatic petroleum fractions, particularly paraffin waxes and cracked and chlorinated analogs and hydrochlorinated analogs thereof, white oils, synthetic alkenes such as those produced by the Ziegler-Natta process (e.g., poly(ethylene) greases) and other sources known to those skilled in the art. Any unsaturation in the A groups may be reduced or eliminated by hydrogenation according to procedures known in the art before the nitration step described hereinafter.
• hydrocarbyl group denotes a group having a carbon atom directly attached to the remainder of the molecule and having a predominantly hydrocarbon character within the context of this invention.
• hydrocarbyl includes hydrocarbon, as well as substantially hydrocarbon, groups.
• substantially hydrocarbon describes groups, including hydrocarbon based groups, which contain non-hydrocarbon substituents, or non-carbon atoms in a ring or chain, which do not alter the predominately hydrocarbon nature of the group.
• Hydrocarbyl groups can contain up to three, preferably up to one, non-hydrocarbon substituent, or non-carbon heteroatom in a ring or chain, for every ten carbon atoms provided this non-hydrocarbon substituent or non-carbon heteroatom does not significantly alter the predominantly hydrocarbon character of the group.
• heteroatoms such as oxygen, sulfur and nitrogen, or substituents, which include, for example, hydroxyl, halo (especially chloro and fluoro), alkoxyl, alkyl mercapto or alkyl sulfoxy.
• hydrocarbyl groups include, but are not necessarily limited to, the following:
• hydrocarbyl groups A are substantially saturated.
• substantially saturated it is meant that the group contains no more than one carbon-to-carbon unsaturated bond for every ten carbon-to-carbon single bonds present. Usually, they contain no more than one carbon-to-carbon non-aromatic unsaturated bond for every 50 carbon-to-carbon bonds present.
• hydrocarbyl groups A of the aminophenols of this invention are also substantially aliphatic in nature, that is, they contain no more than one non-aliphatic moiety (cycloalkyl, cycloalkenyl or aromatic) group of six or less carbon atoms for every ten carbon atoms in the A group.
• the A groups contain no more than one such non-aliphatic group for every fifty carbon atoms, and in many cases, they contain no such non-aliphatic groups at all; that is, the typical A group is purely aliphatic.
• these purely aliphatic A groups are alkyl or alkenyl groups.
• substantially saturated hydrocarbyl A groups are: methyl, tetra (propylene), nonyl, triisobutyl, oleyl, tetracontanyl, henpentacontanyl, a mixture of poly(ethylene/propylene) groups of 35 to 70 carbon atoms, a mixture of the oxidatively or mechanically degraded poly(ethylene/propylene) groups of about 35 to about 70 carbon atoms, a mixture of poly(propylene/1-hexene) groups of 80 to 150 carbon atoms, a mixture of poly(isobutene) groups having between 20 and 32 carbon atoms, and a mixture of poly(isobutene) groups having an average of 50 to 75 carbon atoms.
• a preferred source of hydrocarbyl groups A are polybutenes obtained by polymerization of a C4 refinery stream having a butene content of 35 to 75 weight percent and isobutene content of 15 to 60 weight percent in the presence of a Lewis acid catalyst such as aluminum trichloride or boron trifluoride. These polybutenes contain predominantly (greater than 80% of total repeating units) isobutene repeating units of the configuration
• the attachment of a hydrocarbyl group A to the aromatic moiety Ar of the aminophenols of this invention can be accomplished by a number of techniques well known to those skilled in the art.
• One particularly suitable technique is the Friedel-Crafts reaction, wherein an olefin (e.g., a polymer containing an olefinic bond), or halogenated or hydrohalogenated analog thereof, is reacted with a phenol in the presence of a Lewis acid catalyst.
• Methods and conditions for carrying out such reactions are well known to those skilled in the art. See, for example, the discussion in the article entitled, "Alkylation of Phenols" in "Kirk-Othmer Encyclopedia of Chemical Technology", Third Edition, Vol. 2, pages 65-66, Interscience Publishers, a division of John Wiley and Company, N.Y., and U.S. Patents 4,379,065; 4,663,063; and 4,708,809.
• Other equally appropriate and convenient techniques for attaching the hydrocarbon-based group R to the aromatic moiety Ar will occur readily to those skilled in the art.
• the aminophenols of this invention contain at least one of each of the following substituents: a hydroxyl group, an A group as defined above, and an amino group, -NT2.
• substituents a hydroxyl group, an A group as defined above, and an amino group, -NT2.
• Each of the foregoing groups must be attached to a carbon atom which is a part of an aromatic nucleus in the Ar moiety. They need not, however, each be attached to the same aromatic ring if more than one aromatic nucleus is present in the Ar moiety.
• the aminophenol of the instant invention contains at least one substituent of the formula -NT2.
• Each T is independently H or a hydrocarbyl group having up to about 28 carbon atoms.
• each T is independently H or an alkyl or alkenyl group.
• the alkyl or alkenyl groups contain from 1 to 28 carbon atoms, more often from 1 to 18 carbon atoms.
• at least one T is H with the other T being H or alkyl or alkenyl. In a most preferred embodiment, both T are H.
• the subscript c indicates the number of amino groups that may be present as substituents on the Ar group. There will be at least one such amino group substituent, and there may be more, depending on the values of the subscripts a and b. Preferably, c is a number ranging from 1 to 5. In a preferred embodiment, c is one.
• the subscript b indicates the number of -OH groups appearing as substituents on the aromatic moiety Ar.
• the subscript b must be at least one; however, it may be a number greater than 1 as defined hereinabove.
• the maximum number of -OH groups that may appear on the aromatic moiety Ar depends upon the values for subscripts a and b. Preferably, there will be from 1 to 5 -OH groups as substituents on Ar. In an especially preferred embodiment, there will be but one OH substituent on Ar, that is, the subscript b equals one.
• the aminophenols of this invention contain one each of the foregoing substituents -OH and -NT2 (i.e., b and c are each 1), one A is an aliphatic hydrocarbon-based group with the remaining A groups being H, and but a single aromatic ring, most preferably benzene.
• An especially preferred class of aminophenols can be represented by the general formula wherein the R' group is a substantially saturated hydrocarbyl group of 30 to 400 aliphatic carbon atoms located ortho or para to the hydroxyl group, R'' is a lower alkyl, carboxy lower alkyl, lower alkoxyl, nitro group or halo group and p is 0 or 1.
• R' is a substantially saturated, purely hydrocarbon aliphatic group. Often it is an alkyl or alkenyl group para to the -OH substituent. Often there is but one amino group, -NH2 in these preferred aminophenols but there can be two.
• the aminophenol is of the general formula wherein R' is derived from homopolymerized or interpolymerized C2 ⁇ 10 1-olefins and has an average of from 30 to 400 aliphatic carbon atoms and R'' and p are as defined above.
• R' is derived from polymerized ethylene, propylene, butylenes and mixtures thereof. Typically, it is derived from polymerized butenes. Often R' has at least about 50 aliphatic carbon atoms and p is 0.
• the aminophenols of the present invention can be prepared by a number of synthetic routes. These routes can vary in the type of reactions used and the sequence in which they are employed. For example, an aromatic hydrocarbon, such as benzene, can be alkylated with an alkylating agent such as a polymeric olefin to form an alkylated aromatic intermediate. This intermediate can then be nitrated, for example, to form a polynitro intermediate. The polynitro intermediate can in turn be reduced to a diamine, which can then be diazotized and reacted with water to convert one of the amino groups into a hydroxyl group and provide the desired aminophenol. Alternatively, one of the nitro groups in the polynitro intermediate can be converted to a hydroxyl group through fusion with caustic to provide a hydroxy-nitro alkylated aromatic which can then be reduced to provide the desired aminophenol.
• an aromatic hydrocarbon such as benzene
• an alkylating agent such as a polymeric olefin
• This intermediate can then be n
• Another useful route to the aminophenols of this invention involves the alkylation of a phenol with an olefinic alkylating agent to form an alkylated phenol.
• This alkylated phenol can then be nitrated to form an intermediate nitro phenol which can be converted to the desired aminophenol by reducing at least some of the nitro groups to amino groups.
• Aromatic hydroxy compounds can be nitrated with nitric acid, mixtures of nitric acid with acids such as sulfuric acid or boron trifluoride, nitrogen tetraoxide, nitronium tetrafluoroborates and acyl nitrates.
• nitric acid of a concentration of, for example, 30-90% is a convenient nitrating reagent.
• Substantially inert liquid diluents and solvents such as acetic or butyric acid can aid in carrying out the reaction by improving reagent contact.
• reaction can be carried out at temperatures of -15°C to 150°C, usually between 25-75°C, for a period of time sufficient to attain the desired degree of nitration.
• nitrating agent 0.5-4 moles of nitrating agent is used for every mole of aromatic nucleus present in the hydroxy aromatic intermediate to be nitrated. If more than one aromatic nucleus is present in the Ar moiety, the amount of nitrating agent may be increased proportionally according to the number of such nuclei present. Up to about a 5-molar excess of nitrating agent (per "single ring" aromatic nucleus) may be used when it is desired to drive the reaction forward or carry it out rapidly.
• Reduction of aromatic nitro compounds to the corresponding amines is also well known. See, for example, the article entitled “Amines by Reduction” in Kirk-Othmer “Encyclopedia of Chemical Technology", Third Edition, Vol. 3, pages 335-376.
• reductions can be carried out with, for example, hydrogen, carbon monoxide or hydrazine, (or mixtures of same) in the presence of metallic catalysts, when needed or useful, such as palladium, platinum and its oxides, nickel or copper chromite.
• Co-catalysts such as alkali or alkaline earth metal hydroxides or amines (including aminophenols) can be used in these catalyzed reductions.
• Reduction can also be accomplished through the use of reducing metals in the presence of acids, such as hydrochloric acid.
• Typical reducing metals are zinc, iron and tin or salts thereof.
• Nitro groups can also be reduced in the Zinin reaction, which is discussed in "Organic Reactions", Vol. 20, John Wiley & Sons, N.Y., 1973, page 455 et seq.
• the Zinin reaction involves reduction of a nitro group with divalent negative sulfur compounds, such as alkali metal sulfides, polysulfides and hydrosulfides.
• nitro groups can be reduced by electrolytic action; see, for example, the "Amines by Reduction” article, referred to above.
• One preferred method for obtaining the aminophenols of this invention is the reduction of nitro phenols with hydrogen in the presence of a metallic catalyst such as discussed above. This reduction is generally carried out at temperatures of about 15°C-250°C, and hydrogen pressures of 0-2000 psig (101-13,881 kPa). The reaction time for reduction usually varies between 0.5-50 hours.
• the aminophenol product is obtained by well-known techniques such as distillation, filtration, extraction, and so forth.
• Another preferred method for obtaining the aminophenols of this invention is the reduction of nitro phenols with at least one hydrazine source, optionally in the presence of at least one metal-containing hydrazine decomposition catalyst.
• the hydrazine source used in the present invention is hydrazine, a hydrazine compound or mixture of compounds which are capable of producing hydrazine in sufficient quantities to react with the nitro phenol.
• Hydrazine, hydrazine compounds and many hydrazine sources are known to those of skill in the art. See, for example, the book entitled “Hydrazine” by Charles C. Clark, published by the Mathieson Chemical Corporation of Baltimore, Maryland (1953), particularly pages 31 through 71 and 120 through 124; and the book entitled "The Chemistry of Hydrazine” by L. F. Audrieth and B. A. Ogg, published by John Wiley and Son, New York (1951), especially pages 209 through 223.
• hydrazine and particularly its solutions with water and other solvent/diluents is preferred.
• the reaction of the nitro phenol with the hydrazine source takes place in the absence of a metal-containing hydrazine decomposition catalyst.
• Metals may be present in pure, alloyed or chemically combined form as parts of metallic equipment such as stirrers, pipes, vessels, probes, etc., and in such form they may be in contact with the reaction mass without significantly affecting the course or rate of the decomposition or reaction of the hydrazine source present in the mass. In such cases, for the purpose of the present description, the reaction is said to take place in the absence of a metal-containing hydrazine decomposition catalyst.
• each A is independently H or a hydrocarbyl group
• a, b and c are each independently an integer of at least 1 with the proviso that the sum of a, b and c does not exceed the unsatisfied valences of Ar
• Ar is an aromatic moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, carboxy lower alkyl, halo, or combinations of two or more of said optional substituents; with the proviso that when Ar is a benzene nucleus having only one hydroxyl and only one A which is hydrocarbyl, the hydrocarbyl A group is ortho or para to said hydroxyl substituent.
• An alkylated phenol is prepared by reacting phenol with polybutene having a number average molecular weight of about 1,000 (vapor phase osmometry) in the presence of a boron trifluoride/phenol catalyst. The catalyst is neutralized and removed by filtration. Stripping of the product filtrate first to 230°/760 torr (101 kPa) (vapor temperature), then to 205°/50 torr (6.6 kPa) (vapor temperature), provides purified alkylated phenol as a residue.
• a mixture of 1500 parts of the above intermediate, 642 parts of isopropanol and 7.5 parts of a nickel on Kieselguhr catalyst is charged to an autoclave under a nitrogen atmosphere. After purging and evacuation with nitrogen three times, the autoclave is pressured to 100 psig. (790 kPa) with hydrogen and stirring is begun. The reaction mixture is held at 96° for a total of 14.5 hours while a total of 1.66 moles of hydrogen is fed to it. After purging with nitrogen three times, the reaction mixture is filtered and the filtrate stripped to 120°/18 torr (2.3 kPa). Filtration provides the desired aminophenol product as an oil solution.
• a mineral oil solution (1900 parts) of an alkylated, nitrated phenol as described in Example 1 containing 43% mineral oil is heated under a nitrogen atmosphere to 145°. Then, 70 parts of hydrazine hydrate is slowly added to the mixture over 5 hours while its temperature is held at about 145°. The mixture is then heated to 160° for one hour while 56 parts of aqueous distillate is collected. An additional 7 parts of hydrazine hydrate is added and the mixture is held at 140° for an additional hour. Filtration at 130° provides an oil solution of the desired product containing 0.5% nitrogen.
• Amines useful as Component (B) of the fuel compositions of this invention are amines as defined hereinabove by the general formula (II). They include mono- and polyamines, and may be substantially hydrocarbon-based amines, hydroxy amines, ether amines, amines containing one or more alkoxy groups and others.
• each of x, y and z of general formula (II) is zero.
• Such amines are substantially hydrocarbon amines including primary hydrocarbon amines wherein R1 is alkyl or alkenyl having from 8 to 24 carbon atoms, preferably from 14 to 18 carbon atoms, and R2 and R3 are each H.
• primary alkyl amines are those known as aliphatic primary fatty amines and commercially known as "Armeen” primary amines (products available from Armak Chemicals, Chicago, Ill.).
• Typical fatty amines include alkyl amines such as N-hexylamine, N-octylamine, N-decylamine, N-dodecylamine, N-tetradecylamine, N-pentadecylamine, N-hexadecylamine or N-octadecylamine(stearyl amine).
• These Armeen primary amines are available in both distilled and technical grades. These amines are also available under the tradename "Adogen" available from Sherex.
• Primary alkenyl amines comprise olefinic unsaturation in the hydrocarbon group.
• the R1 group may contain one or more olefinic unsaturated sites depending on the length of the chain, usually no more than one double bond per 10 carbon atoms.
• Representative amines are dodecenylamine, myristoleyamine, palmitoleylamine, oleylamine and linoleylamine. Such unsaturated amines also are available under the Armeen and Adogen tradenames.
• mixed fatty primary amines such as soya amine, coco amine, tallow amines, C20 ⁇ 22 amines, and others. These amines are also available under the Armeen and Adogen tradenames, such as Armeen S, Armeen-T, Adogen 101, Adogen 160 and others.
• Another class of useful primary hydrocarbon amines are the tertiary alkyl amines.
• the carbon atom directly attached to the amino nitrogen is a tertiary carbon atom.
• Each substituent on this carbon atom is a hydrocarbyl group, preferably an alkyl or alkenyl group.
• one of the substituents is an alkyl group having from 5 to 25 carbon atoms, and the other two substituents are lower alkyl, that is, having from 1 to 7 carbons, preferably 1 to 3.
• one of the substituents is alkyl having from about 5 to about 19 carbons and the other two substituents are methyl groups.
• tertiary alkyl primary amines include t-octyl amine and mixtures of isomeric amines in the C12 ⁇ 14 and C18 ⁇ 22 range and are commercially available under the tradename "Primene” (available from Rohm & Haas, Philadelphia, PA).
• hydrocarbon amines also include secondary amines, where one of R2 or R3 is not H, and tertiary amines where neither R2 nor R3 is H.
• Secondary amines include dialkyl amines, for example, where R1 is a hydrocarbyl group having from 8 to 24 carbon atoms, preferably from 14 to 18 carbon atoms, and more preferably alkyl or alkenyl, and one of R2 and R3 is a hydrocarbyl group of 1 to 24 carbon atoms. In one embodiment R1 and one of R2 or R3 are independently alkyl or alkenyl groups having from 8 to 18 carbon atoms.
• R1 is alkyl or alkenyl of 8 to 18 carbons and one of R2 or R3 is alkyl or alkenyl from 1 to 9 carbon atoms, such as methyl, butyl, propyl, isopropyl, octyl, etc.
• Secondary hydrocarbon amines also include those where one of R2 or R3 is a group of general formula (III), wherein y and z are both zero and R5 and R2 and R3 are as defined hereinabove.
• These amines include fatty diamines such as fatty polyamine diamines (including mono- or dialkyl, symmetrical or asymmetrical ethylene diamines, propane diamines (1,2, or 1,3), and polyamine analogs of the above.
• Suitable commercial fatty polyamines are "Duomeen C” (N-coco-1,3-diaminopropane), “Duomeen S” (N-soya-1,3-diaminopropane), “Duomeen T” (N-tallow-1,3-diaminopropane), or “Duomeen O” (N-oleyl-1,3-diaminopropane).
• Duomeens are commercially available diamines described in Product Data Bulletin No. 7-10R1 of Armak Chemical Co., Chicago, Ill.).
• Suitable hydrocarbon based amines also include tertiary amines. These amines are those where R1 and both R2 and R3 are hydrocarbyl groups as defined hereinabove, and x, y and z are all zero.
• R1 is alkyl or alkenyl, especially containing from 14 to 18 carbon atoms
• both R2 and R3 are fatty groups containing from 8 to 24 carbons, preferably up to about 18 carbons.
• Representative tertiary amines are tri(C8 ⁇ 10)amine, tri-hydrogenated tallow amine, di-stearyl methyl amine, tri-tridecyl amine and others, all available under the Adogen tradename.
• Suitable tertiary hydrocarbon amines also include those where neither R2 nor R3 is H, and at least one of these is a group of general formula (III) wherein y and z are each Zero.
• at least one of the amine groups is a tertiary amine group, and there may be other amine groups which are primary, secondary or tertiary, depending upon the definition of the various substituent groups in formula III.
• Ether amines are also useful in the fuel compositions of this invention.
• Ether amines are those where x in general formula (II) is equal to one.
• Ether amines may be primary, secondary or tertiary and may be alkoxylated amines, that is, y and z may be greater than zero and R2 and R3 may be other than H.
• the ether amines are primary or secondary amines or diamines.
• Exemplary ether amines are those where R1 is from 8 to 24 carbons, preferably from 8 to 15 carbons and R4 is an alkylene group having from 2 to 8 carbons, preferably from 3 to 8 carbons. Most preferably, R1 ranges from 12 to 15 carbon atoms and R4 contains 3 carbon atoms.
• Ether amines are commercially available, for example, under the tradename Adogen (Sherex Chemical Co.) or Surfam (Mars Chemical Co., Atlanta, GA).
• exemplary are C13 ether amine (Adogen 183), Adogen 184 (C14 ether amine), Surfam P14AB (branched C14 ether amine), all of which are propane amines, or Adogen 583 (N-(tridecylether propyl) propane diamine) which is a propane diamine.
• At least one of y and z is not zero, and x may be zero or up to 20, preferably zero.
• These amines, depending on the values of R2 and R3 may be secondary or tertiary amines.
• the group R1 is alkyl or alkenyl, having preferably at least 12, more preferably from 14 to 18 carbon atoms, and x equals zero.
• the amine is a monoalkoxylated amine.
• the amine will have the general formula wherein R1 and R4 are as defined hereinabove, n is an integer of from 1 up to 20, Y is a hydrocarbyl group, preferably alkyl or alkenyl, having from 1 to 24 carbon atoms, preferably from 8 to 18 carbon atoms, and Z has the same meaning as R2 or R3 given above.
• Representative examples include dioleylethanolamine or N-methyl,N-octyl-propanolamine.
• both y and z are integers greater than zero.
• These amines may be monoamine or polyamines. These amines may be prepared by reacting a primary amine or a diamine containing one primary and one secondary amine group with an epoxide, such as ethylene oxide or propylene oxide.
• these are ethoxylated or propoxylated fatty amines, that is, R4 is an ethyl or propyl group.
• x equals zero and y and z are integers from 1 to about 20, and each of R2 and R3 is H or hydrocarbyl, preferably alkyl or alkenyl. More often both R2 and R3 are H, and y and z are integers from 1 to 10, and especially from 1 to 5. Most often y and z are both 1.
• R1 is preferably alkyl or alkenyl ranging from 8 to 18 carbons, preferably at least from 12, more often from 14 up to 18 carbon atoms.
• Examples of these amines include alkoxylated, preferably ethoxylated or propoxylated fatty amines, such as alkoxylated octyl amine, dodecyl amine, pentadecenyl amine, oleyl amine or tallow amine.
• R2 and R3 is a group of general formula (III) wherein R5 is alkylene containing from 2 to 8 carbon atoms, preferably 2 or 3 carbon atoms, y and z are integers as defined hereinabove, preferably zero, and R2 and R3 are as defined hereinabove, preferably H.
• amines examples include alkoxylated, preferably ethoxylated or propoxylated fatty diamines, such as N-oleyl, N',N'-dihydroxyethyl propane diamine, and soya, coco, tallow and stearyl analogues thereof.
• the especially preferred amines are the "Ethomeens” and "Ethoduomeens," a series of commercial mixtures of ethyoxylated fatty amines available from Armak Company.
• Suitable “Ethomeens” include “Ethomeen C/12,” “Ethomeen S/12,” “Ethomeen T/12,” “Ethomeen 0/12” and “Ethomeen 18/12.”
• R1 is a mixture of alkyl and alkenyl groups derived respectively from coconut oil, soybean oil and tallow, and in “Ethomeen 0/12" and “18/12", it is, respectively, oleyl and stearyl.
• R1 is as defined for the Ethomeens described hereinabove.
• Fluidizer oils may be used in the fuel compositions of the instant invention.
• Useful fluidizer oils may be natural oils or synthetic oils, or mixtures thereof.
• Natural oils include mineral oils, vegetable oils, animal oils, and oils derived from coal or shale.
• Synthetic oils include hydrocarbon oils such as alkylated aromatic oils, olefin oligomers, esters, including esters of polycarboxylic acids and polyols. For reasons of cost and availability, mineral oils are preferred.
• paraffinic oils containing no more than about 20% unsaturation that is, no more than 20% of the carbon to carbon bonds are olefinic.
• the fluidizer oils have a kinematic viscosity ranging from 10 to 20 centistokes (1-2 x 10 ⁇ 5 m2/s) at 100°C, preferably from 11 to 16 centistokes (1.1-1.6 x 10 ⁇ 5 m2/s), and most preferably from 11 to 14 centistokes (1.1-1.4 x 10 ⁇ 5 m2/s). If the viscosity of the fluidizer oil is too high, a problem that may arise is the development of octane requirement increase (ORI) wherein the octane value demands of the engine tend to increase with time of operation.
• ORI octane requirement increase
• fluidizer oils when used within the ranges specified herein, together with the aminophenols and amines of this invention, improve detergency and reduce the tendency toward valve sticking. Amounts of the various additives, including individual amounts to be used in the fuel composition, and relative amounts of additives are given hereinafter.
• the fuel is a normally liquid fuel in the gasoline boiling range. These fuels are well known to those skilled in the art and are those defined by ASTM Specification D-439.
• the fuels useful in the compositions of this invention usually contain a major portion of normally liquid fuel such as hydrocarbonaceous petroleum distillate fuel. Fuels useful in the compositions of this invention may also contain non-hydrocarbonaceous material such as alcohols, ethers, organo-nitro compounds and the like (e.g., methanol, ethanol, diethylether, methylethyl ether, nitromethane). These fuels may be derived from vegetable or mineral sources, including, for example, crude petroleum oil, coal, corn, shale and other sources.
• suitable fuel mixtures are combinations of gasoline and ethanol, gasoline and nitromethane, etc.
• Preferred fuels are gasoline, oxygenates, and gasoline-oxygenate blends, all as defined in the aforementioned ASTM D-439 Specification for automotive gasoline. Most preferred is gasoline.
• the fuel compositions of the present invention may contain other additives which are well known to those of skill in the art. These can include anti-knock agents such as tetra-alkyl lead compounds, lead scavengers such as halo-alkanes, dyes, antioxidants such as hindered phenols, rust inhibitors such as alkylated succinic acids and anhydrides and derivatives thereof, bacteriostatic agents, gum inhibitors, metal deactivators, demulsifiers and anti-icing agents.
• the fuel compositions of this inventions may be lead-containing and lead-free fuels. Preferred are lead-free fuels.
• the motor fuel compositions contain a sufficient amount of additives to provide total intake system cleanliness. In another embodiment, they are used in amounts sufficient to prevent or reduce the formation of intake valve deposits or to remove them where they have formed.
• the relative amounts of the aminophenol (A) and the amine (B) range from 150:1 to 1:100 parts by weight.
• the aminophenol is present from 10 to 150 parts by weight, per thousand barrels of fuel (0.0285-0.4281 kg/m3), and the amine is present at from 1 to 100 pounds by weight, per thousand barrels of fuel (0.0029-0.2854 kg/m3).
• the fuel may contain (C) a fluidizer oil.
• the relative amounts of (A) to (C) ranges from 1:20 to 3:1 by weight.
• the fuel compositions may contain from about 30 to about 150 pounds by weight, per thousand barrels of fuel of the fluidizer oil (0.0856-0.4281 kg/m3).
• PTB pounds per thousand barrels
• Table I illustrates several fuel compositions of the instant invention comprising unleaded gasoline and the indicated amounts of additive in kg/m3 of gasoline.
• a fuel composition is prepared employing 1600 PTB (4.5664 kg/m3) (approx. 6400 ppm) of the above concentrate. This treatment is intended to provide "one-tank" cleanup of a dirty fuel delivery system including port fuel injectors and intake valves.
• a gasoline fuel containing from about 200 to about 1000 (0.5708-2.8540 kg/m3), preferably to about 700 PTB (1.9978 kg/m3) of an aminophenol (A) and from 20 to 100 PTB (0.0571-0.2854 kg/m3), preferably to 70 PTB (0.1998 kg/m3) of amine (B) can be used to clean a dirty fuel delivery system which system comprises port fuel injectors and intake valves.
• the fuel evaluation procedure is based on 10,000 miles (16,090 km) of driving in the BMW model 318i vehicle equipped with 1.8L 4-cylinder engine and automatic transmission.
• the testing is initiated with new, carefully weighed intake valves. This is followed by 16090 km (10,000 miles) of operation with the candidate fuel, and then disassembly of the cylinder head to reweigh the intake valves.
• the primary data consists of intake valve deposit ratings and weights, and photographs of the intake valves.
• the significant data is the actual deposit weight on the intake valves at 16090 km (10,000 miles). Fuels are then classified in one of the three categories based on the following criteria established for the average of the four intake valves:
• a gasoline fuel composition was prepared comprising 44 PTB (0.1256 kg/m3) of a polybutene substituted aminoethylethanolamine and 82.5 PTB (0.2355 kg/m3) of a fluidizer oil comprising a residue bright stock.
• BMW testing resulted in valve deposits ranging from 19.2 mg to 171.5 mg with an average of 94.5 mg.
• Two gasoline fuel compositions were prepared comprising 75 PTB (0.2140 kg/m3) (45 PTB (0.1284 kg/m3) on oil-free basis) of an aminophenol as described in Example 1 of this application and 112.5 PTB (0.3211 kg/m3) of a fluidizer oil comprising a residue bright stock.
• BMW testing resulted in valve deposits ranging from 35.3 to 100.6 mg with an average of 67 mg.
• Three gasoline fuel compositions were prepared comprising 80 PTB (0.2283 kg/m3) (48 PTB (0.1370 kg/m3) on oil-free basis) of the amonophenol of Example 1, 120 PTB (0.3425 kg/m3) of fluidizer oil comprising bright stock and each containing an amount of one of the amines falling within the description of component (B).
• BMW testing of these fuels resulted in an average of about 45 mg valve deposits.

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• 1992
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• 1996
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