CN113227332A - Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines - Google Patents
Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines Download PDFInfo
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- CN113227332A CN113227332A CN201980085825.9A CN201980085825A CN113227332A CN 113227332 A CN113227332 A CN 113227332A CN 201980085825 A CN201980085825 A CN 201980085825A CN 113227332 A CN113227332 A CN 113227332A
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- 238000000034 method Methods 0.000 title claims description 19
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
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- C10L2200/00—Components of fuel compositions
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Abstract
Disclosed herein is a fuel composition comprising: (1) greater than 50 wt% of a hydrocarbon fuel boiling in the gasoline or diesel range, and (2) a minor amount of a low-speed pre-ignition (LSPI) reducing additive comprising one or more of an amidine or a β -aminoalkanol having the structure or a salt thereof, wherein R is1、R2、R3And R4Each independently selected from hydrogen, aromatic ring and C1‑C20Alkyl, and R5Is hydrogen or has the structure- (CH) R6Alcohols of-OH, R6Is hydrogen, C1‑C10Alkyl or C1‑C10An alkenyl group.
Description
Cross Reference to Related Applications
The present application is a co-pending, U.S. provisional patent application serial No.16/362,157 entitled "composite AND METHOD FOR achieving OR REDUCING LOW SPEED PRE-alignment IN space-IGNITED INTERNAL alignment ends" filed on 3, 22.2019, which claims U.S. provisional patent application No.62/647,186 entitled "composite AND METHOD FOR achieving OR REDUCING LOW SPEEDING PRE-alignment IN space-IGITED INTERNAL alignment ends" filed on 3, 23.2018 AND U.S. provisional patent application No. 62/767,686 entitled "composite AND METHOD FOR achieving OR REDUCING LOW SPEED alignment IN space-IGNITED INTERNAL alignment ends" filed on 11, 15.2018, which is incorporated by reference.
Technical Field
The present disclosure relates to fuel and lubricant compositions for spark-ignition engines and methods of using them to prevent or reduce low speed pre-ignition events.
Background
Turbocharged or supercharged engines (i.e., supercharged internal combustion engines) may experience an abnormal combustion event known as random pre-ignition or low speed pre-ignition (or "LSPI"). LSPI is an event that may include very high pressure spikes, pre-ignition that occurs during improper crankshaft angles, and knock. All of these, individually and in combination, can cause engine degradation and/or severe damage. However, because LSPI events happen only by chance in an uncontrolled manner, it is difficult to identify the cause of this phenomenon and to develop solutions to contain it.
Pre-ignition is a form of combustion that results in combustion of the air-fuel mixture within the combustion chamber prior to the desired ignition of the air-fuel mixture by the igniter. Pre-ignition is typically a problem during high load operation of the engine, as the heat generated by engine operation will heat a portion of the combustion chamber to a temperature sufficient to ignite the air-fuel mixture at contact. This type of pre-ignition is sometimes referred to as hot-spot pre-ignition.
Recently, intermittent abnormal combustion has been observed in a supercharged internal combustion engine of low speed and medium to high load. For example, during engine operation at 3,000 rpm or less, low load, at least 10bar Brake Mean Effective Pressure (BMEP), low speed pre-ignition (LSPI) may occur in a random and random manner. During low speed engine operation, the compression stroke time is longest.
Previous studies have shown that the use of turbochargers, engine design, engine coatings, piston shape, fuel selection, and/or oil additives may contribute to an increase in LSPI events. Accordingly, there is a need for fuel and engine oil additive components and/or combinations that are effective in reducing or eliminating LSPI.
Summary of the invention
In one aspect, there is provided a fuel composition comprising: (1) greater than 50 wt% of a hydrocarbon fuel boiling in the gasoline or diesel range, and (2) a minor amount of a low-speed pre-ignition (LSPI) reducing additive comprising one or more of an amidine or a β -aminoalkanol having the structure:
wherein R is1、R2、R3And R4Each independently selected from hydrogen, aromatic ring and C1-C20Alkyl, and R5Is hydrogen or has the structure- (CH) R6Alcohols of-OH, wherein R6Is hydrogen, C1-C10Alkyl, or C1-C10An alkenyl group.
In another aspect, a fuel concentrate is provided comprising: (1)90 to 30 wt% of an organic solvent having a boiling point in the range of 65 ℃ to 205 ℃, and (2)10 to 70 wt% of an additive component comprising one or more of an amidine or a β -aminoalkanol having the structure:
wherein R is1、R2、R3And R4Each independently selected from hydrogen, aromatic ring and C1-C20Alkyl, and R5Is hydrogen or has the structure- (CH) R6Alcohols of-OH, wherein R6Is hydrogen, C1-C10Alkyl, or C1-C10An alkenyl group.
In another aspect, a method of reducing low speed pre-ignition events in an engine is provided, the method comprising (1) greater than 50 wt.% of a hydrocarbon fuel boiling in the gasoline or diesel range and (2) a minor amount of a low speed pre-ignition (LSPI) reducing additive comprising one or more of a triazole, an amidine, or a beta-aminoalkanol having the structure:
wherein R is1、R2、R3And R4Each independently selected from hydrogen and C1-C20Alkyl, and R5Is hydrogen or has the structure- (CH) R6Alcohols of-OH, wherein R6Is hydrogen, C1-C10Alkyl, or C1-C10An alkenyl group.
Detailed Description
Introduction to
In the present specification, if the following words and expressions are used, they have the meanings given below.
By "gasoline" or "gasoline boiling range component" is meant comprising at least predominantly C4-C12A composition of hydrocarbons. In one embodiment, gasoline or gasoline boiling range component is further defined to mean a gasoline composition comprising at least predominantly C4-C12A composition of hydrocarbons and boiling range from about 100 ° F (37.8 ℃) to about 400 ° F (204 ℃). In an alternative embodiment, a gasoline or gasoline boiling range component is defined to mean a component containing at least predominantly C4-C12The hydrocarbon composition of (a), having a boiling range of from about 100 ° F (37.8 ℃) to about 400 ° F (204 ℃) and further defined as meeting ASTM D4814.
The term "diesel fuel" means a fuel comprising at least predominantly C10-C25A hydrocarbon middle distillate fuel. In one embodiment, diesel is further defined to mean comprising at least primarily C10-C25A composition of hydrocarbons and boiling range from about 165.6 ℃ (330 ° F) to about 371.1 ℃ (700 ° F). In an alternative embodiment, diesel fuel is as defined above and means comprising at least predominantly C10-C25A composition of hydrocarbons and boiling range from about 165.6 ℃ (330 ° F) to about 371.1 ℃ (700 ° F) and further defined in accordance with astm d 975.
The term "oil-soluble" refers to an amount required to provide a desired level of activity or performance for a given additive, which may be incorporated by dissolving, dispersing or suspending it in an oil of lubricating viscosity. Typically, this means that at least 0.001 wt.% of the additive can be incorporated into the lubricating oil composition. The term "fuel-soluble" is a similar expression for an additive dissolved, dispersed or suspended in fuel.
The term "alkyl" refers to a saturated hydrocarbon group, which may be linear, branched, cyclic or a combination of cyclic, linear and/or branched.
An "alkanol" is an alkyl group as described herein having a hydroxyl substituent (i.e., -OH group).
By "minor amount" is meant less than 50% by weight of the composition, expressed with respect to the additive and with respect to the total weight of the composition, of what is considered to be an active ingredient of the additive.
An "analog" is a compound that has a structure similar to another compound but differs from the compound in that certain components, such as one or more atoms, functional groups, substructures, are replaced with another atom, group, or substructure.
"homologues" are compounds belonging to a series of compounds that differ from each other by a repeating unit. Alkanes are examples of homologs. For example, ethane and propane are homologs in that they are only in the repeat unit (-CH)2-) differ in length. Homologues may be considered as a particular type of analogue.
A "derivative" is a compound that is derived from a similar compound via a chemical reaction (e.g., an acid-base reaction, hydrogenation, etc.). In the context of a substituent, a derivative may be a combination of one or more moieties. For example, the phenol moiety can be considered to be a derivative of the aryl moiety and the hydroxyl moiety. Those of ordinary skill in the relevant art will know the boundaries of what are to be considered derivatives. The term "substituted" refers to the substitution or replacement of one or more atoms of a compound. As an illustrative example, "substituted alkyl" refers in particular to ethanol.
An "engine" or "combustion engine" is a heat engine in which combustion of a fuel occurs within a combustion chamber. An "internal combustion engine" is a heat engine in which combustion of fuel occurs in a confined space ("combustion chamber"). A "spark ignition engine" is a heat engine whose combustion is usually ignited by a spark plug. This is in contrast to "compression ignition engines" (typically diesel engines) in which the heat generated by the compression and fuel injection together is sufficient to initiate combustion without external sparks.
Low-speed pre-ignition (LSPI)
Low speed pre-ignition (LSPI) is most likely to occur in direct injection, supercharged (turbocharged or supercharged), spark ignition (gasoline) internal combustion engines which, when operated, produce a braking mean effective pressure of greater than 1000kPa (10bar) at engine speeds of 1500 to 2500 revolutions per minute (rpm), for example at engine speeds of 1500 to 2000 rpm. "brake mean effective pressure" (BMEP) is defined as the work done during an engine cycle divided by the engine displacement by which the engine torque is normalized. The word "braking" means the actual torque or power available on the engine flywheel measured on the dynamometer. Therefore, BMEP is a measure of the useful energy output of the engine.
It has now been found that the fuel composition or lubricating oil composition of the present disclosure is particularly suitable for use in high pressure spark-ignited internal combustion engines and when used in high pressure spark-ignited internal combustion engines will prevent or minimize engine knock and pre-ignition problems.
Main additive for reducing LSPI
The following is a description of the primary additives that may be used as fuel or lubricant additives to reduce LSPI activity. The LSPI-reducing primary additive may be used as a stand-alone additive and/or with other primary additives and/or one or more LSPI-reducing secondary additives (described later). When more than one additive is used, the additive may be in the form of a salt. Further, when two or more additives are used, there may be a synergistic effect between the two or more additives. Typically, these additives are fuel or oil soluble at the concentrations required to achieve the desired level of reduction of LSPI. Table 1 summarizes the main additive types.
TABLE 1
1. Amino additive
Beta-aminoalkanols
The fuel additive or lubricating oil additive of the present disclosure may be a beta-aminoalkanol, a substituted beta-aminoalkanol, a derivative thereof, or an acceptable salt thereof. Useful beta-aminoalkanols include those which can be represented by the general formula:
wherein R is1、R2、R3And R4Each independently selected from hydrogen and C1-C20Alkyl (e.g. C)1-C6Alkyl groups); r1、R2、R3And R4Two or more of which may optionally be joined together to form a ring structure (e.g., a five-, six-, or seven-membered ring). In some embodiments, R1、R2、R3And R4May independently comprise one or more aromatic rings. R5Is hydrogen or has the structure- (CH) R6Alcohols of-OH, wherein R6Is hydrogen, C1-C10Alkyl, or C1-C10An alkenyl group. In some embodiments, R5Is hydrogen. In some embodiments, R5Is having a formula of- (CH) R6Alcohols of the structure-OH, in which R6Is hydrogen, C1-C10Alkyl, or C1-C10An alkenyl group.
In embodiments, the beta-aminoalkanols are not:
in certain embodiments, the fuel composition does not comprise:
in certain embodiments, the fuel concentrate does not comprise:
in certain embodiments, the beta-aminoalkanols used in the method of reducing low speed pre-ignition events in an engine are not:
in certain embodiments, the low speed pre-ignition (LSPI) reducing additive does not comprise:
in embodiments, the amino alcohol is not:
the beta-aminoalkanols have at least 2 carbon atoms (e.g., 4 to 30 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, 5 to 30 carbon atoms, 5 to 20 carbon atoms, 5 to 16 carbon atoms, or 5 to 12 carbon atoms).
Representative examples of suitable beta-aminoalkanols include ethanolamine (formula 1A), 1-amino-2-propanol (formula 1B), alaninol (formula 1C), 2- (methylamino) ethanol (formula 1D), 2- (ethylamino) ethanol (formula 1E), 2-amino-2-methyl-1-propanol (formula 1F), 2-amino-1-butanol (formula 1G), 2-amino-1-pentanol (formula 1H), valinol (formula 1I), 2-amino-1-hexanol (formula 1J), leucinol (formula 1K), isoleucinol (formula 1L), cycloleucinol (formula 1M), cyclohexylethanolamine (formula 1N), prolinol (formula 1O), 2- (hydroxymethyl) piperidine (formula 1P), 2-aminocyclopentanol (formula 1Q) and 2-aminocyclohexanol (formula 1R), aminoheptyl propanediol (3- (heptan-2-ylamino) propane-1, 2-diol) (formula 1T), aminooctyl propanediol (3- (methyl (octyl) amino) propane-1, 2-diol) (formula 1U), and aminododecyl ethanol (2- (methyl (dodecyl) amino) ethan-1-ol) (formula 1V). In certain embodiments, the β -aminoalkanol is aminoheptylpropanediol (3- (heptan-2-ylamino) propane-1, 2-diol) (formula 1T). In certain embodiments, the beta-aminoalkanol is aminooctylpropanediol (3- (methyl (octyl) amino) propane-1, 2-diol) (formula 1U). In certain embodiments, the beta-aminoalkanol is aminododecylethanol (2- (dodecyl (methyl) amino) ethan-1-ol) (formula 1V). Representative structures are shown below.
In certain embodiments, the beta-aminoalkanol is not:
in certain embodiments, the fuel composition does not comprise:
in certain embodiments, the fuel concentrate does not comprise:
in certain embodiments, the beta-aminoalkanols used in the method of reducing low speed pre-ignition events in an engine are not:
in certain embodiments, the low speed pre-ignition (LSPI) reducing additive does not comprise:
in certain embodiments, the amino alcohol is not:
in certain embodiments, the β -aminoalkanol is or comprises aminoheptyl propylene glycol, provided that it is not:
in certain embodiments, the fuel composition comprises aminoheptyl propylene glycol, provided that it is not:
in certain embodiments, the fuel concentrate comprises aminoheptyl propylene glycol, provided that it is not:
in certain embodiments, the beta-aminoalkanol used in the method of reducing low speed pre-ignition events in an engine is or comprises aminoheptyl propylene glycol, provided that it is not:
in certain embodiments, the low speed pre-ignition (LSPI) reducing additive is or comprises an aminoheptyl propylene glycol, provided that it is not:
in certain embodiments, the amino alcohol is or comprises an amino heptyl propylene glycol, provided that it is not:
amino acids
The fuel additive or lubricating oil additive of the present disclosure may be an aliphatic amino acid, a substituted aliphatic amino acid, or a derivative or acceptable salt thereof. Useful amino acids include those that can be represented by the general formula:
wherein R is an "aliphatic" or "aromatic" side chain. Amino acid side chains can be broadly classified as aromatic or aliphatic. The aromatic side chain includes an aromatic ring. Examples of the amino acid having an aromatic side chain include, for example, histidine (formula 2A), phenylalanine (formula 2B), tyrosine (formula 2C), tryptophan (formula 2D), and the like. The non-aromatic side chains are broadly classified as "aliphatic" and include, for example, alanine (formula 2E), glycine (formula 2F), cysteine (formula 2G), and the like.
The amino acids may be natural and/or unnatural alpha-amino acids. Natural amino acids are amino acids encoded by the genetic code, as well as amino acids derived therefrom. These include, for example, hydroxyproline (formula 2H), γ -carboxyglutamate (formula 2I), and citrulline (formula 2J). In this specification, the term "amino acid" also includes amino acid analogues and mimetics. Analogs are compounds having the same general structure as a natural amino acid, except that the R group is not one of the natural amino acids.
Representative examples of natural amino acid analogs include homoserine (formula 2K), norleucine (formula 2L), homoproline (formula 2M), and proline (formula 2N). Amino acid mimetics are compounds that have a structure that is different from the general chemical structure of an alpha-amino acid, but that functions in a similar manner. The amino acid may be an L-or D-amino acid. Representative structures are shown below.
Amino esters
The fuel additive or lubricating oil additive of the present disclosure may be an amino ester, a substituted amino ester, or a derivative thereof, or an acceptable salt thereof. The amino ester may be derived from an amino acid (as described above) and an alcohol. The amino acid ester and the amino acid can be considered as derivatives of each other. Useful amino esters include those that can be represented by the general formula:
wherein R is an aliphatic side chain, R1Is a carbon chain of 1 to 20 carbon atoms in length, preferably 1 to 4 carbon atoms, in particular methanol or ethanol, preferably methanol.
The amino ester may comprise aromatic or aliphatic side chains. Representative examples of amino esters include alanine methyl ester (formula 3A), alanine ethyl ester (formula 3B), glycine methyl ester (formula 3C), and glycine ethyl ester (formula 3D). Representative structures are shown below.
2.N=C-XModified additive
The fuel or lubricating oil additives of the present disclosure may have an N ═ C-X modification, as shown by the following general structure
Wherein R is H, a monovalent organic group or a monovalent heteroorganic group (described in more detail below), X1And X2Independently is H, C, N, O or S, and wherein X1Or X2Independently comprise one or more C1-C20Alkyl radicals (e.g. C)1-C6Alkyl) or one or more aromatic rings. In some embodiments, X1And X2May include cyclic structures (e.g., five, six, or seven membered rings). The cyclic structure may be aromatic or non-aromatic and may range from fully saturated to fully unsaturated. Suitable examples of additives compatible with formula 4 include amidines, guanidines, imidazoles, benzamidines, benzimidazoles and aminobenzimidazoles.
Amidines
The fuel additive or lubricating oil additive of the present disclosure may be an amidine, a substituted amidine or derivative thereof, or an acceptable salt thereof. Useful amidines include those which can be represented by the general formula:
wherein R is5、R6、R7And R8Each independently selected from hydrogen, monovalent organic groups, monovalent heteroorganic groups (e.g., including nitrogen, oxygen, sulfur, or phosphorus, in the form of groups or moieties bonded through a carbon atom and not containing an acid functional group such as a carboxylic acid or sulfonic acid), and combinations thereof; and wherein R5、R6、R7And R8Any two or more ofAnd may optionally be joined together to form a cyclic structure (e.g., a five-, six-, or seven-membered ring). The cyclic structure may be aromatic or non-aromatic and may range from fully saturated to fully unsaturated. The organic and heteroorganic groups can have 1 to 10 carbon atoms (e.g., 1 to 6 carbon atoms).
Representative examples of suitable amidines include 1,4,5, 6-tetrahydropyrimidine (formula 5A), 1, 2-dimethyl-1, 4,5, 6-tetrahydropyrimidine (formula 5B), 1, 2-diethyl-1, 4,5, 6-tetrahydropyrimidine (formula 5C), 1, 5-diazabicyclo [4.3.0] non-5-ene (DBN; formula 5D), 1, 8-diazabicyclo [5.4.0] -undec-7-ene (DBU; formula 5E), benzamidine (formula 5F), benzimidazole (formula 5G), and 2-phenyl-1H-benzo [ D ] imidazole (formula 5M). Representative structures are shown below.
Guanidine (guanidine)
The fuel additive or lubricating oil additive of the present disclosure may be a guanidine, substituted guanidine, or derivative or acceptable salt thereof. Useful guanidines include those that can be represented by the general formula:
wherein R is9、R10、R11、R12And R13Each independently selected from hydrogen, monovalent organic groups, monovalent heteroorganic groups (e.g., including nitrogen, oxygen, sulfur, or phosphorus, in the form of groups or moieties bonded through a carbon atom and not containing an acid functional group such as a carboxylic acid or sulfonic acid), and combinations thereof; and wherein R9、R10、R11、R12And R13Any two or more of which may optionally be joined together to form a ring structure (e.g., aSuch as five, six or seven membered rings). The cyclic structure may be aromatic or non-aromatic and may range from fully saturated to fully unsaturated. The organic and heteroorganic groups can have 1 to 10 carbon atoms (e.g., 1 to 6 carbon atoms).
Representative examples of suitable guanidines include 1,1,3, 3-tetramethylguanidine (TMG; formula 6A), 2-tert-butyl-1, 1,3, 3-tetramethylguanidine (BTMG; formula 6B), 1,5, 7-triazabicyclo [4.4.0] dodec-5-ene (TBD; formula 6C), 7-methyl-1, 5, 7-triazabicyclo [4.4.0] dodec-5-ene (MTBD; formula 6D), and 1, 2-diphenylguanidine (formula 6I). Representative structures are shown below.
Imidazole
The fuel additive or lubricating oil additive of the present disclosure may be an imidazole, a substituted imidazole or a derivative thereof or an acceptable salt thereof. Suitable imidazoles include imidazole (formula 7A), 1-methylimidazole (formula 7B), 1-ethylimidazole (formula 7D), 1-propylimidazole (formula 7E), 1-n-butylimidazole (formula 7F), 1-decylimidazole, 1-dodecylimidazole, 2-methylimidazole (formula 7G), 2-ethylimidazole, 2-isopropylimidazole (formula 7H), 4-methylimidazole (formula 7I), 1, 2-dimethylimidazole (formula 7J), 2-ethyl-4 (5) -methylimidazole (formula 7K), and 1-vinylimidazole (formula 7L). Representative structures are shown below.
3. Triazole additives
The fuel additive or lubricating oil additive of the present disclosure may be a triazole, a substituted triazole or a derivative or acceptable salt thereof. Suitable triazoles include 1,2, 3-triazole (formula 8A), 5, 6-dimethylbenzotriazole (formula 8B), 1,2, 4-triazole (formula 8C), piperidine-substituted triazoles (formula 8D) and benzotriazole analogs, for example alkyl-substituted benzotriazoles, such as methyl-substituted benzotriazoles (formula 8E). Representative structures are shown below.
4.Benzamidine onium additives
The fuel additive or lubricating oil additive of the present disclosure may be benzamidine onium, substituted benzamidine onium or its derivatives or acceptable salts thereof. Useful benzamidinium additives include those which can be represented by the following formula 9, wherein R1、R2And R3Independently is C1-C20An alkyl group.
Suitable benzamidiniums include N, N-dimethyl-N-octylbenzamidinium-2-oxide (formula 9A). Representative structures are shown below.
5. Benzoxazole additives
The fuel additive or lubricating oil additive of the present disclosure may be a benzoxazole, a substituted benzoxazole or a derivative or acceptable salt thereof. Suitable benzoxazoles include benzoxazoles (formula 10A) and 2-aminobenzoxazole (formula 10B). Representative structures are shown below.
6. Amine additives
Aromatic amines
The fuel additive or lubricating oil additive of the present disclosure may be an aromatic amine, a substituted aromatic amine, or a derivative or acceptable salt thereof. The aromatic amine additive may have a general structure shown in formula 11-1 or 11-2,
wherein R is independently one or more of H or C1-C20Alkyl, X is N (e.g. R-N-R) or O-。
Suitable aromatic amines include 2-methylquinolin-8-amine (formula 11A). Representative structures are shown below.
Aliphatic amines
Suitable aliphatic amines are shown below.
Auxiliary additive for reducing LSPI
The following is a description of LSPI-reducing supplementary additives that may be used as fuel or lubricity additives to reduce LSPI activity. Typically, the LSPI-reducing co-additive, the substituted LSPI-reducing co-additive or derivative thereof is used in the form of a salt thereof in combination with the main additive to reduce LSPI activity. For example, beta-aminoalkanols (primary additives) and fatty acids (secondary additives) can be combined and used as LSPI additives. Table 2 lists the auxiliary additive types. Some additives may act as primary additives and/or secondary additives.
TABLE 2
7. Acid additive
Fatty acids
The aliphatic acid is a non-aromatic carboxylic acid. Suitable aliphatic acids include monocarboxylic acids having the structure
Wherein R is an aliphatic group having 2 to 20 carbon atoms. Aliphatic groups may be straight or branched chain and may contain heteroatoms.
Suitable aliphatic acids include caproic acid (formula 13A), heptanoic acid (formula 13B), caprylic acid (formula 13C), nonanoic acid (formula 13D), capric acid (formula 13E), undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid (C)20) Behenic acid (C)22) 2-ethylbutyric acid (formula 13F), 3-dimethylbutyric acid, 2-methylpentanoic acid (C)6) 2-methylhexanoic acid (C)7) 4-methylhexanoic acid (C)7) 5-methylhexanoic acid (C)7) 2, 2-Dimethylpentanoic acid (C)7) 2-Propylpentanoic acid (C)8) 2-ethylhexanoic acid (formula 13G), 2-methylheptanoic acid (C)8) Isooctanoic acid (C)8) 3,5, 5-trimethylhexanoic acid (C)9) 4-Methyloctanoic acid (C)9) 4-methylnonanoic acid, (C)10) Isodecanoic acid (C)10) 2-Butyloctanoic acid (C)12) Isotridecanoic acid (C)13) 2-hexyldecanoic acid (C)16) Isopalmitic acid (C)16) Isostearic acid (formula 13H), 3-cyclohexylpropionic acid, 4-cyclohexylbutyric acid (formula 13I) and cyclohexaneproentanoic acid. Representative structures are shown below.
Unsaturated acid
Suitable unsaturated acids include any organic acid containing a double or triple carbon-carbon bond. Representative unsaturated acids include maleic acid (formula 14A), fumaric acid (formula 14B), and unsaturated fatty acids such as palmitoleic acid (formula 14C) and oleic acid (formula 14D). Representative structures are shown below.
Alkyl aromatic acid
Suitable alkyl aromatic acids include monocarboxylic acids and dicarboxylic acids. The alkyl carboxylic acid can have 6 or more carbon atoms (e.g., 6 to 24 carbon atoms, 6 to 20 carbon atoms, 8 to 24 carbon atoms, 8 to 20 carbon atoms, or even 8 to 18 carbon atoms). The alkyl moiety may be optionally substituted with one or more substituents such as hydroxyl, alkoxy, and carbonyl (e.g., aldehyde or ketone groups). Suitable examples of the alkyl aromatic acid include methyl benzoic acid (formula 15A) and ethyl benzoic acid (formula 15B). Representative structures are shown below.
Aromatic acid
Suitable aromatic acids include monocarboxylic acids and dicarboxylic acids. The alkyl carboxylic acid can have 6 or more carbon atoms (e.g., 6 to 24 carbon atoms, 6 to 20 carbon atoms, 8 to 24 carbon atoms, 8 to 20 carbon atoms, or even 8 to 18 carbon atoms). The alkyl moiety may be optionally substituted with one or more substituents such as hydroxyl, alkoxy, and carbonyl (e.g., aldehyde or ketone groups). Suitable aromatic acids include benzoic acid (formula 16A), hydroxybenzoic acid (formula 16B), and tetrahydronaphthoic acid (formula 16C). Representative structures are shown below.
Hydroxy acids
Suitable hydroxy acids include those that can be represented by the general formula:
wherein n is 1-3. Suitable examples of hydroxy acids include glycolic acid (formula 17A), lactic acid (formula 17B), malic acid (formula 17C), tartaric acid (formula 17D), and citric acid (formula 17E). Representative structures are shown below.
Amino acids
Amino acids may be used as primary and/or secondary additives. Suitable amino acids are as described previously.
8. Phenol additives
Phenol and its salts
Suitable phenols include thymol (formula 18A), eugenol (formula 18B), hydroquinone (formula 18C), resorcinol (formula 18D), cresols (formula 18E), and 2-methylquinolin-8-ol (formula 18G). Representative structures are shown below.
9.1, 3-dicarbonyl additives
1, 3-diketones
Suitable examples of the 1, 3-diketone compound include acetylacetone (formula 19A) and curcumin (formula 19B). Representative structures are shown below.
1,3 Keto-acid esters
Suitable 1, 3-keto esters are shown below.
10. Hydroxyamide additives
Hydroxyamides are hydroxy derivatives of amides. Useful hydroxyamides include those which can be represented by the general formula:
wherein R is1And R2Each independently selected from hydrogen or C1-C20(e.g. C)3-C12) An alkyl group. Suitable hydroxyamides include hydroxymethyl acetamide (formula 21A). Representative structures are shown below.
11. Antioxidant agent
Suitable antioxidants include monocarboxylic acids and dicarboxylic acids. The alkyl carboxylic acid can have 6 or more carbon atoms (e.g., 6 to 24 carbon atoms, 6 to 20 carbon atoms, 8 to 24 carbon atoms, 8 to 20 carbon atoms, or even 8 to 18 carbon atoms). The alkyl moiety may be optionally substituted with one or more substituents such as hydroxyl, alkoxy, and carbonyl (e.g., aldehyde or ketone groups). Suitable antioxidants include the following.
12. Salicylic acid additives
Salicylic acids
Suitable salicylic acids include 2-hydroxy-5- (tetracosan-1, 3,5,7,9,11,13,15,17,19,21, 23-dodecyl-1-yl) benzoic acid-dihydro (formula 23E). Suitable salicylic acids are shown below.
Salts
The salts of the present disclosure may be prepared in conventional manner, for example by mixing the main additive with suitable auxiliary additives in an aprotic solvent. The order in which one additive is added to the other is not critical. The primary and secondary additives are typically mixed together in about equimolar ratios. An excess of the primary or secondary additive components may be used. For example, the molar ratio of base to alkyl carboxylic acid can be about 1.05: 1 to 2: 1 (e.g., 1.1: 1 to 1.5: 1). Representative salts are shown below.
Fuel composition
The compounds of the present disclosure may be used as additives in hydrocarbon fuels to prevent or reduce engine knock or pre-ignition events in spark-ignited internal combustion engines.
The concentration of the compounds of the present invention in the hydrocarbon fuel may be 25 to 5000 parts per million (ppm) by weight (e.g., 50 to 1000 ppm).
The compounds of the present disclosure may be formulated into concentrates using inert stable lipophilic (i.e., soluble in hydrocarbon fuels) organic solvents that boil in the range of 65 ℃ to 205 ℃. Aliphatic or aromatic hydrocarbon solvents such as benzene, toluene, xylene or higher boiling aromatics or aromatic diluents may be used. Aliphatic alcohols having 2 to 8 carbon atoms, such as ethanol, isopropanol, methyl isobutyl carbinol, n-butanol, and the like, in combination with hydrocarbon solvents are also suitable for use with the additives of the present invention. The amount of additive in the concentrate can be 10 to 70 wt% (e.g., 20 to 40 wt%).
In gasoline fuels, other well-known additives may be used, including oxygenates (e.g., ethanol, methyl tertiary butyl ether), other antiknock agents and detergents/dispersants (e.g., hydrocarbyl amines, hydrocarbyl polyalkylene oxides) amines, succinimides, Mannich reaction products, aromatic esters of polyalkylphenoxyalkanols, or polyalkylphenoxyaminoalkanes). Additionally, friction modifiers, antioxidants, metal deactivators, and demulsifiers may be present.
In diesel fuels, other well-known additives may be used, such as pour point depressants, flow improvers, cetane number improvers, and the like.
A fuel-soluble, non-volatile carrier fluid or oil may also be used with the compounds of the present disclosure. The carrier fluid is a chemically inert hydrocarbon-soluble liquid vehicle that substantially increases the non-volatile residue (NVR) or solvent-free liquid portion of the fuel additive composition without significantly causing an increase in octane requirement. The carrier fluid may be a natural or synthetic oil, such as mineral oil, refined petroleum, synthetic polyalkanes and alkenes, including hydrogenated and unhydrogenated polyalphaolefins, synthetic polyoxyalkylene derived oils, such as those described in U.S. patent 3,756,793; 4,191,537; 5,004,478; and european patent application publication nos.356,726 and 382,159.
The carrier fluid may be used in an amount in the range of 35 to 5000ppm by weight of the hydrocarbon fuel (e.g., 50 to 3000ppm of the fuel). When used in a fuel concentrate, the carrier fluid may be present in an amount of 20 to 60 wt% (e.g., 30 to 50 wt%).
Lubricating oil composition
The compounds of the present invention are useful as additives in lubricating oils to prevent or reduce engine knock or pre-ignition events in spark-ignited internal combustion engines.
The concentration of the compounds of the present invention in the lubricating oil composition can be from 0.01 to 15 wt.% (e.g., from 0.5 to 5 wt.%), based on the total weight of the lubricating oil composition.
An oil of lubricating viscosity (sometimes referred to as a "base stock" or "base oil") is the main liquid component of a lubricant, into which additives and possibly other oils are incorporated, such as may be made into the final lubricant (or lubricant component). The base oils which may be used to prepare the concentrates and lubricating oil compositions therefrom may be selected from natural (vegetable, animal or mineral) and synthetic lubricating oils and mixtures thereof.
The definition of base stocks and base Oils in this disclosure is the same as that in American Petroleum Institute (API) publication 1509 annex E ("APIBase Oil interchange properties guides for Passenger Car Motor Oils and diesel Engine Oils," month 12 2016). Using the test methods specified in Table E-1, the saturates content of the group I base stocks is less than 90% and/or the sulfur content is greater than 0.03% and the viscosity index is greater than or equal to 80 and less than 120. Using the test methods specified in Table E-1, the saturates content of the group II base stocks was greater than or equal to 90%, the sulfur content was less than or equal to 0.03%, and the viscosity index was greater than or equal to 80 and less than 120. Using the test methods specified in Table E-1, the saturates content of the group III basestocks was greater than or equal to 90%, the sulfur content was less than or equal to 0.03%, and the viscosity index was greater than or equal to 120. Group IV basestocks are Polyalphaolefins (PAOs). Group V base stocks include all other base stocks not included in group I, II, III or IV.
Natural oils include animal oils, vegetable oils (e.g., castor oil and lard oil), and mineral oils. Animal and vegetable oils having good thermo-oxidative stability can be used. Among natural oils, mineral oils are preferred. Crude oils of mineral oils vary widely in origin, for example, they are paraffinic, naphthenic or mixed paraffinic-naphthenic. Oils derived from coal or shale are also useful. Natural oils are also produced and purified by processes such as distillation ranges and whether they are straight run or cracked, hydrofinished or solvent extracted.
Synthetic oils include hydrocarbon oils. Hydrocarbon oils include oils such as polymerized and copolymerized olefins (e.g., polybutylenes, polypropylenes, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylene-alpha-olefin copolymers). Polyalphaolefin (PAO) oil basestocks are commonly used synthetic hydrocarbon oils. For example, derivatives from C may be used8To C14PAOs of alkenes, e.g. C8、C10、C12、C14Olefins or mixtures thereof.
Other useful fluids for use as base oils include unconventional base oils that have been processed, preferably catalyzed or synthesized, to provide high performance characteristics.
Unconventional base stocks/base oils include one or more base oil blends derived from: one or more Gas To Liquids (GTL) materials and iso/iso dewaxed base oils derived from natural wax or waxy feeds, mineral and/or non-mineral oil waxy feeds (e.g. slack wax, natural wax) and waxy feedstocks such as gas oils, waxy fuel hydrocracked bottoms, waxy raffinates, hydrocrackers, thermal crackers or other minerals, mineral oils, even non-petroleum derived waxy materials such as waxy materials obtained from coal liquefaction or shale oils, and mixtures of these base stocks.
The base oils used in the lubricating oil compositions of the present disclosure are any of the various oils corresponding to API group I, group II, group III, group IV and group V, and mixtures thereof, preferably API group II, group III, group IV, group V oils, and mixtures thereof, and more preferably group III to group V base oils because of their excellent volatility, stability, viscosity and cleanliness characteristics.
Typically, the kinematic viscosity of the base oil at 100 ℃ (ASTM D445) is from 2.5 to 20mm2S (e.g. 3 to 12 mm)2S, 4 to 10mm2Or 4.5 to 8mm2/s)。
The lubricating oil compositions of the present invention may also contain conventional lubricant additives to impart ancillary functions to the finished lubricating oil composition in which these additives are dispersed or dissolved. For example, the lubricating oil composition may be mixed with antioxidants, ashless dispersants, anti-wear agents, detergents such as metal detergents, rust inhibitors, dehazing agents, demulsifying agents, friction modifiers, metal deactivating agents, pour point depressants, viscosity modifiers, antifoaming agents, co-solvents, package compatibilisers, corrosion-inhibitors, dyes, extreme pressure agents and the like and mixtures thereof. Various additives are known and commercially available. The lubricating oil composition of the present invention can be prepared by a conventional mixing method using these additives or their analogous compounds.
When used, each of the foregoing additives is used in a functionally effective amount to impart the desired properties to the lubricant. Thus, for example, if the additive is an ashless dispersant, a functionally effective amount of the ashless dispersant will be an amount sufficient to impart the desired dispersancy properties to the lubricant. Generally, unless otherwise specified, the concentration of each of these additives may range from about 0.001 to about 20 weight percent, for example from about 0.01 to about 10 weight percent.
Examples
The following illustrative examples are intended to be non-limiting.
Examples 1 to 45
Test compounds were blended in gasoline or lubricating oil and their ability to reduce LSPI events was determined using the test method described below.
The LSPI test was performed using a GM 2.0L LHU 4 cylinder gasoline turbocharged direct injection engine. Each cylinder is equipped with a combustion pressure sensor.
A six-stage test procedure was used to determine the number of LSPI events that occurred at an engine speed of 2000rpm and a load of 275 Nm. The LSPI test conditions were run for 28 minutes with an idle time interval between each segment. The first segment is used to condition the engine oil and does not count the number of LSPI events. Each segment is slightly truncated to eliminate transient portions. Each truncated segment typically has about 100,000 combustion cycles (25,000 combustion cycles per cylinder). In general, the five cutoffs for the calculated LSPI event are approximately 500,000 combustion cycles (125,000 combustion cycles per cylinder). If the engine is unable to complete all six parts, the test time may be shortened.
The LSPI-affected combustion cycle was determined by monitoring the peak cylinder pressure (PP) and crank angle at 5% total exotherm (AI 5). The combustion cycle affected by LSPI is defined as (1) PP being greater than the average PP of the given cylinder and the cutback by five standard deviations, and (2) AI5 being greater than the average of the given cylinder and the cutback by five standard deviations or less.
The LSPI frequency is reported as the number of combustion cycles affected by LSPI per million combustion cycles and is calculated as follows:
LSPI frequency ═ total number of LSPI-affected combustion cycles in five cutbacks)/(total number of combustion cycles in five cutbacks) ] × 1,000,000
Additives associated with test fuels and/or test lubricants that reduce the LSPI frequency are considered LSPI frequency mitigating additives when compared to the corresponding reference fuels and/or reference lubricants. The test results are shown in Table 2.
Claims (20)
1. A fuel composition comprising: (1) greater than 50 wt% of a hydrocarbon fuel boiling in the gasoline or diesel range, and (2) a minor amount of a low-speed pre-ignition (LSPI) reducing additive comprising one or more of an amidine or a β -aminoalkanol having the structure:
wherein R is1、R2、R3And R4Each independently selected from hydrogen,Aromatic ring and C1-C20Alkyl, and R5Is hydrogen or has the structure- (CH) R6Alcohols of-OH, wherein R6Is hydrogen, C1-C10Alkyl, or C1-C10An alkenyl group.
2. The fuel composition of claim 1, wherein R1、R2、R3And R4Two or more of which form a ring structure.
3. The fuel composition of claim 1, wherein R1、R2、R3And R4At least one of which is an aromatic ring.
4. The fuel composition of claim 1, wherein the LSPI-reducing additive is an amino alcohol.
5. The fuel composition of claim 4, wherein the amino alcohol is aminoheptyl propylene glycol, aminooctyl propylene glycol, or aminododecyl ethanol.
6. The fuel composition of claim 1, wherein the LSPI-reducing additive is 3- (heptan-2-ylamino) propane-1, 2-diol, 3- (methyl (octyl) amino) propane-1, 2-diol, or 2- (methyl (dodecyl) amino) ethan-1-ol.
7. The fuel composition of claim 1, wherein the LSPI-reducing additive is DBU 2-methylquinoline-8-oleate or DBU C24-salicylate.
8. The fuel composition of claim 1, wherein the salt comprises an auxiliary additive comprising one or more of: an acid additive, a phenol additive, a 1, 3-dicarbonyl additive, an isohydroxyamide additive, an antioxidant additive, or a salicylic acid additive.
9. A fuel concentrate, comprising: (1)90 to 30 wt% of an organic solvent having a boiling point in the range of 65 ℃ to 205 ℃, and (2)10 to 70 wt% of an additive component comprising one or more of an amidine or a β -aminoalkanol having the structure:
wherein R is1、R2、R3And R4Each independently selected from hydrogen, aromatic ring and C1-C20Alkyl, and R5Is hydrogen or has the structure- (CH) R6Alcohols of-OH, wherein R6Is hydrogen, C1-C10Alkyl, or C1-C10An alkenyl group.
10. The fuel concentrate of claim 9, wherein R1、R2、R3And R4Two or more of which form a ring structure.
11. The fuel concentrate of claim 9, wherein R1、R2、R3And R4At least one of which is an aromatic ring.
12. The fuel concentrate of claim 9, wherein the LSPI reducing additive is an amino alcohol.
13. The fuel concentrate of claim 12, wherein the amino alcohol is aminoheptyl propylene glycol, aminooctyl propylene glycol, or aminododecyl ethanol.
14. The fuel concentrate of claim 9, wherein the LSPI-reducing additive is 3- (heptan-2-ylamino) propane-1, 2-diol, 3- (methyl (octyl) amino) propane-1, 2-diol, or 2- (methyl (dodecyl) amino) ethan-1-ol.
15. The fuel concentrate of claim 9, wherein the LSPI-reducing additive is DBU 2-methylquinoline-8-oleate or DBU C24-salicylate.
16. A method of reducing low speed pre-ignition events in an engine, the method comprising
(1) Greater than 50 wt.% of a hydrocarbon fuel boiling in the gasoline or diesel range and (2) a minor amount of a low-speed pre-ignition (LSPI) reducing additive comprising one or more of a triazole, an amidine, or a beta-aminoalkanol having the structure:
wherein R is1、R2、R3And R4Each independently selected from hydrogen and C1-C20Alkyl, and R5Is hydrogen or has the structure- (CH) R6Alcohols of-OH, wherein R6Is hydrogen, C1-C10Alkyl, or C1-C10An alkenyl group.
17. The method of claim 16, wherein the triazole is benzotriazole.
18. The method of claim 16, wherein the LSPI-reducing additive is an amino alcohol.
19. The method of claim 16, wherein the amino alcohol is aminoheptyl propylene glycol, aminooctyl propylene glycol, or aminododecyl ethanol.
20. The method of claim 16, wherein the LSPI-reducing additive is 3- (heptan-2-ylamino) propane-1, 2-diol, 3- (methyl (octyl) amino) propane-1, 2-diol, or 2- (methyl (dodecyl) amino) ethan-1-ol.
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US16/362,157 US20190292473A1 (en) | 2018-03-23 | 2019-03-22 | Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines |
PCT/IB2019/058057 WO2020099953A1 (en) | 2018-11-15 | 2019-09-23 | Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines |
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US20160230115A1 (en) * | 2013-09-19 | 2016-08-11 | The Lubrizol Corporation | Lubricant compositions for direct injection engines |
CN106957698A (en) * | 2015-12-10 | 2017-07-18 | 雅富顿化学公司 | Dialkylaminoalkanols friction improver for fuel and lubricant |
WO2018041710A1 (en) * | 2016-09-01 | 2018-03-08 | Tunap Gmbh & Co. Kg | Fuel additive for cleaning an internal combustion engine |
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US20160230115A1 (en) * | 2013-09-19 | 2016-08-11 | The Lubrizol Corporation | Lubricant compositions for direct injection engines |
CN106957698A (en) * | 2015-12-10 | 2017-07-18 | 雅富顿化学公司 | Dialkylaminoalkanols friction improver for fuel and lubricant |
WO2018041710A1 (en) * | 2016-09-01 | 2018-03-08 | Tunap Gmbh & Co. Kg | Fuel additive for cleaning an internal combustion engine |
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