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  • C10L1/188—Carboxylic acids; metal salts thereof
  • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
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  • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
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  • 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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Definitions

• This invention is directed to novel fuel compositions for internal combustion engines and to methods for using such fuel compositions.
• Additives for fuels such as anti-icing agents, lead-containing fuel additives, detergents, and various antioxidants generally resulted in adequate performance. Deposits in other parts of the fuel delivery system were not of a major concern because such engines were generally tuned to a rich air/fuel ratio allowing for mixture malfunction. Greater power-weight ratios meant that the driver was less apt to notice changes in peak power and fuel economy, and exhaust emissions were not a serious concern at that time.
• Another object is to provide novel fuel compositions that meet at least one of the above-stated objects and do not contribute towards valve-sticking.
• a further object is to provide a method for maintaining total intake system cleanliness in a gasoline-fueled internal combustion engine.
• Still another object is to provide a method for preventing or reducing the formation of intake valve deposits in a port fuel injected engine, or for removing such deposits where they have formed.
• Another object is to provide an additive composition comprising more than one additive, wherein the additives do not interact with each other in an adverse manner, and which provide an unexpected improvement in intake system cleanliness and reduction or elimination of intake valve deposits.
• the present invention is directed to motor fuel compositions comprising a normally liquid fuel in the gasoline boiling range;
• each A is independently H or a substantially saturated hydrocarbon-based group
• each T is independently H or a hydrocarbyl group of up to about 28 carbon atoms
• a, b and c are each independently an integer of at least one with the proviso that the sum of a, b and c does not exceed the unsatisfied valences of Ar
• Ar is a single ring, a fused polynuclear ring or a linked polynuclear ring aromatic moiety having 0 to 3 optional substituents selected from the group consisting essentially of lower alkyl , lower alkoxyl , nitro, carboxy lower alkyl, nitroso, halo and combinations of two or more of said optional substituents;
• R 1 is a hydrocarbyl group containing from about 8 to about 24 carbon atoms
• R 2 and R 3 are each independently H, a hydrocarbyl group containing from 1 to about 24 carbon atoms or a group of the general formula
• R 5 is an alkylene group containing from 2 to about 8 carbon atoms
• R 2 and R 3 are as defined hereinabove
• each R 4 is independently an alkylene group containing from 2 to about 8 carbon atoms
• each of x, y and z is independently an integer from 0 to about 20.
• 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 provide total intake system cleanliness. In another embodiment, 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 provide total intake system cleanliness. In another embodiment, 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 provide total intake system cleanliness. In another embodiment, 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 provide total intake system cleanliness.
• (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.
• the presence of 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, a 1,2,3,4-tetrahydronaphthalene nucleus, etc., 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 found in naphthalene, anthracene, the azanaphthalenes, etc.
• 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 the group consisting of 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.
• 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 halogen atoms are fluorine and chlorine atoms.
• Ar is a polynuclear fused-ring aromatic moiety, it can be represented by the general formula
• aromatic moiety Ar is a linked polynuclear aromatic moiety, it can be represented by the general formula
• each Lng is a bridging linkage individually chosen from the group consisting of carbon-to-carbon single bonds, ether linkages (e.g. -O-), keto linkages sulfide linkages (e.g., -S-), polysulfide linkages of 2 to 6 sulfur atoms (e.g., -S 2 - 6 -) , sulfinyl linkages (e.g.,
• sulfonyl linkages e.g., -S(O) 2 -
• lower alkylene linkages e.g., -CH 2 -, -CH 2 -CH 2 -,
• di(lower alkyl)-methylene linkages e.g., CRo 2 -
• lower alkylene ether linkages e.g., -CH 2 O-, -CH 2 O-CH 2 -,
• lower alkylene polysulfide linkages e.g., wherein one or more
• polyamino linkages e.g., polyamino linkages
• one or more of the ar groups in the above-linked aromatic moiety can be replaced by fused nuclei such as ar .
• linked moieties are:
• 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 about 9 to about 750 carbons.
• the hydrocarbyl group A has at least about 30 to about 400 carbon atoms, more typically, at least about 50 carbon atoms and up to about 750, more typically, up to about 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 about 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 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, 1-octene, etc.
• 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, alkyl sulfoxy, etc.
• hydrocarbyl groups include, but are not necessarily limited to, the following:
• hydrocarbon substituents that is, aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, aromatic-, aliphatic- and alicyclic-substituted aromatic substituents and the like as well as cyclic substituents wherein the ring is completed through another portion of the molecule (that is, for example, any two indicated substituents may together form an alicyclic radical);
• aliphatic e.g., alkyl or alkenyl
• alicyclic e.g., cycloalkyl, cycloalkenyl
• substituted hydrocarbon substituents that is, those substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon substituent; those skilled in the art will be aware of such groups (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, sulfoxy, etc.);
• hetero substituents that is, substituents which will, while having a predominantly hydrocarbon character within the context of this invention, contain atoms other than carbon present in a ring or chain otherwise composed of carbon atoms.
• Suitable heteroatoms will be apparent to those of ordinary skill in the art and include, for example, sulfur, oxygen, nitrogen and such substituents as, e.g., pyridyl, furyl, thienyl, imidazolyl, etc.
• no more than about 2, preferably no more than one, non-hydrocarbon substituent or non-carbon atom in a ring moiety, will be present for every ten carbon atoms in the hydrocarbyl group.
• the hydrocarbyl groups are purely hydrocarbon and contain no such non-hydrocarbon groups or substituents.
• 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 about 35 to about 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 about 80 to about 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 C . 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
• 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.
• 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, -NT 2 .
• substituents a hydroxyl group, an A group as defined above, and an amino group, -NT 2 .
• 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 -NT 2 .
• 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 about 28 carbon atoms, more often from 1 to about 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 about 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 about 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 -NT 2 (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 formula
• R' group is a substantially saturated hydrocarbyl group of about 30 to about 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
• p is 0 or 1.
• p is O
• 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, -NH 2 in these preferred aminophenols but there can be two.
• the aminophenol is of the general formula
• R' is derived from homopolymerized or interpolymerized C 2-10 1-olefins and has an average of from about 30 to about 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 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 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 nitrated,
• 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 aminophenols 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, about 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 about -15oC to about 150oC, usually between about 25-75"C, for a period of time sufficient to attain the desired degree of nitration.
• nitrating agent about 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 proportionately 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, copper chromite, etc.
• 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 15oC-250oC, and hydrogen pressures of about 0-2000 psig. The reaction time for reduction usually varies between about 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 metal-containing hydrazine decomposition catalyst.
• Metals may be present in pure, alloyed or chemical 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.
• A is H or substantially saturated hydrocarbyl group
• c is an integer of at least 1 with the proviso that the sum of a 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, carboxyl lower alkyl, nitro, and halo, or combinations of two or more optional substituents, with the provisos that (a) Ar' has at least one hydrogen atom directly bonded to a carbon atom which is part of an aromatic nucleus, and (b) when Ar' is a benzene having only one hydroxyl and only one A group is hydrocarbyl, the hydrocarbyl A group is ortho or para to said hydroxyl substituent, to form a first reaction mixture containing a nitro intermediate, and (II) reducing at least about 50% of the nitro groups in said first reaction mixture to amino groups.
• 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 (vapor temperature), then to 205°/50 torr (vapor temperature), provides purified alkylated phenol as a residue.
• 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. 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. 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° prov is 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 (I). 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 Formula I is zero.
• Such amines are substantially hydrocarbon amines including primary hydrocarbon amines wherein R 1 is alkyl or alkenyl having from 8 to about 24 carbon atoms, preferably from about 14 to about 18 carbon atoms, and R 2 and R 3 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, 111.).
• Typical fatty amines include alkyl amines such as N-hexylamine, N-octylamine, N-decylamine, N-dodecylamine, N-tetradecylamine, N-pentadecylamine, N-hexadecylamine, N-octadecylamine(stearyl amine), etc.
• 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 R 1 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.
• 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 about 25 carbon atoms, and the other two substituents are lower alkyl, that is, having from 1 to about 7 carbons, preferably 1 to about
• 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 C 12-14 and C 18-22 range and are commercially available under the tradename "Primene” (available from Rohm & Haas, Philadelphia, PA).
• hydrocarbon amines also include secondary amines, where one of R 2 or R 3 is not H, and tertiary amines where neither R 2 nor R 3 is H.
• Secondary amines include dialkyl amines, for example, where R 1 is a hydrocarbyl group having from 8 to about 24 carbon atoms, preferably from about 14 to about
• R 2 and R 3 are preferably alkyl or alkenyl, and one of R 2 and R 3 is a hydrocarbyl group of 1 to about
• R 1 and one of R 2 or R 3 are independently alkyl or alkenyl groups having from
• R is alkyl or alkenyl of about 8 to about 18 carbons and one of R 2 or R 3 is alkyl or alkenyl from 1 to about 9 carbon atoms, such as methyl, butyl, propyl, isopropyl, octyl, etc.
• Secondary hydrocarbon amines also include those where one of R 2 or R 3 is a group of formula (III), wherein y and z are both zero and R 5 and R 2 and R 3 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 Arm
• Suitable hydrocarbon based amines also include tertiary amines. These amines are those where R 1 and both R 2 and R 3 are hydrocarbyl groups as defined heremabove, and x, y and z are all zero.
• R 1 is alkyl or alkenyl, especially containing from about 14 to about 18 carbon atoms
• both R 2 and R 3 are fatty groups containing from about 8 to about 24 carbons, preferably up to about 18 carbons.
• tertiary amines are tri(C 8-10 ) amine, tri-hydrogenated tallow amine, di-stearyl methyl amine, tri-tridecyl amine and others, all available under the
• Suitable tertiary hydrocarbon amines also include those where neither R 2 nor R 3 is H, and at least one of these is a group of 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 Formula (I) 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 R 2 and R 3 may be other than H.
• the ether amines are primary or secondary amines or diamines.
• Exemplary ether amines are those where R 1 is from 8 to 24 carbons, preferably from 8 to 15 carbons and R 4 is an alkylene group having from about 2 to about 8 carbons, preferably from 3 to about 8 carbons. Most preferably, R 1 ranges from about 12 to about 15 carbon atoms and R 4 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 C 13 ether amine (Adogen 183), Adogen 184 (C 14 ether amine), Surfam P14AB (branched C 14 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 about 20, preferably zero.
• These amines, depending on the values of R 2 and R 3 may be secondary or tertiary amines.
• the group R 1 is alkyl or alkenyl, having preferably at least
• the amine is a monoalkoxylated amine.
• the amine will have the general formula
• R 1 and R 4 are as defined heremabove, n is an integer of from 1 up to about 20, Y is a hydrocarbyl group, preferably alkyl or alkenyl, having from 1 to about 24 carbon atoms, preferably from 8 to about 18 carbon atoms, and Z has the same meaning as R 2 or R 3 given above.
• Representative examples include dioleylethanolamine, N-methyl,N-octyl-propanolamine, etc.
• 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, R 4 is an ethyl or propyl group.
• x equals zero and y and z are integers from 1 to about 20, and each of R 2 and R 3 is H or hydrocarbyl, preferably alkyl or alkenyl. More often both R 2 and R 3 are H, and y and z are integers from 1 to about 10, and especially from 1 to about 5. Most often y and z are both 1.
• R 1 is preferably alkyl or alkenyl ranging from 8 to about 18 carbons, preferably at least from 12, more often from 14 up to about 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, tallow amine, and the like.
• R 2 and R 3 is a group of formula III wherein R 5 is alkylene containing from 2 to about 8 carbon atoms, preferably 2 or 3 carbon atoms, y and z are integers as defined hereinabove, preferably zero, and R 2 and R 3 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.”
• R 1 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.
• R 1 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, and others. 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 about 10 to about 20 centistokes at 100°C, preferably from about 11 to about 16 centistokes, and most preferably from about 11 to about 14 centistokes. 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 which is hereby expressly incorporated by reference for its detailed description of fuels suitable for use in the compositions of this invention.
• 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).
• 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, anti-icing agents and the like.
• the fuel compositions of this inventions may be lead-containing and lead-free fuels. Preferred are lead-free fuels.
• the motor fuel compositions contain an amount of additives sufficient 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 about 150:1 to about 1:100 parts by weight.
• the aminophenol is present from about 10 to about 150 parts by weight, per thousand barrels of fuels, and the amine is present at from about 1 to about 100 pounds by weight, per thousand barrels of fuel.
• the fuel may contain (C) a fluidizer oil.
• the relative amounts of (A) to (C) ranges from about 1:20 to about 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.
• 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 pounds per thousand barrels of gasoline.
• Hydrocarbon solvent 93 93 100 100 42.5 100 100 100 100 100 100 100 120 120
• Fluidizer oil 150 120 120 120 120 120 120 120 120 120 120 120 120 120 120 120 120 120 120 150 150
• a fuel composition is prepared employing 1600 PTB (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, preferably to about 700 PTB of an aminophenol (A) and from about 20 to about 100 PTB, preferably to about 70 PTB 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 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 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 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 of a polybutene substituted aminoethylethanolamine and 82.5 PTB 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 (45 PTB on oil-free basis) of an aminophenol as described in Example 1 of this application and 112.5 PTB 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 (48 PTB on oil-free basis) of the amonophenol of Example 1, 120 PTB 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
  • 1992-01-20 TW TW081100353A patent/TW239158B/zh active
  • 1992-01-21 AU AU12576/92A patent/AU654170B2/en not_active Ceased
  • 1992-01-21 CA CA002080375A patent/CA2080375A1/en not_active Abandoned
  • 1992-01-21 JP JP92505387A patent/JPH05507313A/ja active Pending
  • 1992-01-21 BR BR9204777A patent/BR9204777A/pt not_active Application Discontinuation
  • 1992-01-21 DE DE69201538T patent/DE69201538T2/de not_active Expired - Fee Related
  • 1992-01-21 EP EP92905026A patent/EP0525157B1/en not_active Expired - Lifetime
  • 1992-01-21 RU RU9292016343A patent/RU2062781C1/ru active
  • 1992-01-21 PL PL29638692A patent/PL296386A1/xx unknown
  • 1992-01-21 AT AT92905026T patent/ATE119192T1/de active
  • 1992-01-21 WO PCT/US1992/000472 patent/WO1992014805A1/en active IP Right Grant
  • 1992-01-21 HU HU9203252A patent/HUT64100A/hu unknown
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  • 1992-02-14 ZA ZA921096A patent/ZA921096B/xx unknown
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  • 1992-10-13 NO NO1992923977A patent/NO923977D0/no unknown
  • 1992-10-14 FI FI924643A patent/FI924643A0/fi not_active Application Discontinuation
• 1996
  • 1996-03-07 HK HK39596A patent/HK39596A/en not_active IP Right Cessation

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