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  • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
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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
  • C10L1/1883—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
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  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
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  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
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  • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
  • C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/228—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
  • 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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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
  • C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
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  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/10—Use of additives to fuels or fires for particular purposes for improving the octane number
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  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
  • C10L2200/0415—Light distillates, e.g. LPG, naphtha
  • C10L2200/0423—Gasoline
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  • C10L2270/00—Specifically adapted fuels
  • C10L2270/02—Specifically adapted fuels for internal combustion engines
  • C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines

Definitions

• This disclosure relates to fuel and lubricant compositions for spark-ignited engines and methods for preventing or reducing low speed pre-ignition events using the same.
• Turbocharged or supercharged engines may exhibit an abnormal combustion phenomenon known as stochastic pre-ignition or low-speed pre-ignition (or "LSPI").
• LSPI is an event that may include very high pressure spikes, early combustion during an inappropriate crank angle, and knock. All of these, individually and in combination, have the potential to cause degradation and/or severe damage to the engine.
• LSPI events occur only sporadically and in an uncontrolled fashion, it is difficult to identify the causes for this phenomenon and to develop solutions to suppress it.
• Pre-ignition is a form of combustion that results in ignition of the air-fuel mixture in the combustion chamber prior to the desired ignition of the air-fuel mixture by the igniter.
• Pre-ignition has typically been a problem during high load engine operation since heat from operation of the engine may heat a part of the combustion chamber to a sufficient temperature to ignite the air-fuel mixture upon contact. This type of pre-ignition is sometimes referred to as hot-spot pre-ignition.
• BMEP brake mean effective pressure
• LSPI low-speed pre-ignition
• 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 beta-amino alkanol having the structure , wherein R 1 , R 2 , R 3 , and R 4 are each independently selected from hydrogen, aromatic ring, and a C 1 -C 20 alkyl group and R 5 is hydrogen or an alcohol having the structure -(CH)R 6 -OH wherein R 6 is hydrogen, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkenyl group, or a salt thereof.
• LSPI low-speed pre-ignition
• a “minor amount” means less than 50 wt % of a composition, expressed in respect of the stated additive and in respect of the total weight of the composition, reckoned as active ingredient of the additive.
• Low Speed Pre-Ignition is most or more likely to occur in direct-injected, boosted (turbocharged or supercharged), spark-ignited (gasoline) internal combustion engines that, in operation, generate a brake mean effective pressure level of greater than 1000 kPa (10 bar) at engine speeds of from 1500 to 2500 rotations per minute (rpm), such as at engine speeds of from 1500 to 2000 rpm.
• BMEP Brain mean effective pressure
• the word “brake” denotes the actual torque or power available at the engine flywheel, as measured on a dynamometer.
• BMEP is a measure of the useful energy output of the engine.
• Primary additives that can be utilized as a fuel or lubricant additive to reduce LSPI activity.
• Primary LSPI-reducing additives can be used as standalone additives and/or with other primary additive(s) and/or with of one or more secondary LSPI-reducing additive (described later). When more than one additive is used, the additives may be in salt form. Moreover, when two or more additives are used, there may be synergy between the two or more additives. In general, these additives are fuel or oil soluble at concentrations needed to achieved a desired LSPI reduction level. Table 1 summarizes the primary additive types. Table 1 Primary Additive Types 1. Amino Additives Beta-amino alkanol Amino acid Amino ester 2.
• N C-X Motif Additives Amidine Guanidine Imidazole Benzamidine Benzamidazole Aminobenzimidazole 3. Triazole Additives 4. Benzamidium Additives 5. Benzoxazole Additives 6. Amine Additives Aromatic amine Aliphatic amine
• the fuel additive or lubricating oil additive of this disclosure may be a ⁇ -amino alkanol, a substituted ⁇ -amino alkanol, a derivative thereof or an acceptable salt thereof.
• Useful ⁇ -amino alkanols include those that can be represented by the following general formula: wherein R 1 , R 2 , R 3 , and R 4 are each independently selected from hydrogen and a C 1 -C 20 alkyl (e.g., C 1 -C 6 alkyl) group; and two or more of R 1 , R 2 , R 3 , and R 4 optionally can be bonded together to form a ring structure (e.g., a five-, six-, or seven-membered ring).
• R 1 , R 2 , R 3 , and R 4 may independently include one or more aromatic rings.
• R 5 is hydrogen or an alcohol having the structure -(CH)R 6 -OH wherein R 6 is hydrogen, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkenyl group.
• R 5 is hydrogen.
• R 5 is an alcohol having the structure -(CH)R 6 -OH wherein R 6 is hydrogen, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkenyl group.
• the ⁇ -amino alkanol is not the following:
• the fuel composition does not comprise the following:
• the fuel concentrate does not comprise the following:
• the amino alcohol is not the following:
• the ⁇ -amino alkanol is aminoheptyl propanediol (3-(heptan-2-ylamino)propane-1,2-diol) ( Formula 1T ). In certain embodiments, the ⁇ -amino alkanol is aminooctyl propanediol (3-(methyl(octyl)amino)propane-1,2-diol) ( Formula 1U ). In certain embodiments, the ⁇ -amino alkanol is aminododecyl ethanol (2-(dodecyl(methyl)amino)ethan-1-ol) ( Formula 1V ). Representative structures are shown below.
• the fuel composition does not comprise the following:
• the ⁇ -amino alkanol is or comprises aminoheptyl propanediol, with the proviso that it is not the following:
• the fuel additive or lubricating oil additive of this disclosure may be a guanidine, a substituted guanidine, or a derivative thereof, or an acceptable salt thereof.
• Useful guanidines include those that can be represented by the following general formula, wherein R 9 , R 10 , R 11 , R 12 and R 13 are each independently selected from hydrogen, monovalent organic groups, monovalent heterorganic groups (e.g., comprising nitrogen, oxygen, sulfur or phosphorus, in the form of groups or moieties that are bonded through a carbon atom and that do not contain acid functionality such as carboxylic or sulfonic), and combinations thereof; and wherein any two or more of R 9 , R 10 , R 11 , R 12 and R 13 optionally can be bonded together to form a cyclic structure (e.g., a five-, six, or seven-membered ring).
• the cyclic structures may be aromatic or non-aromatic, as well as vary from being fully saturated to fully unsatur
• the fuel additive or lubricating oil additive of this disclosure may be a benzamidinium, a substituted benzamidinium, or a derivative thereof, or an acceptable salt thereof.
• Useful benzamidinium additives include those that can be represented by the following general formula 9, wherein R 1 , R 2 , and R 3 are independently C 1 -C 20 alkyl groups.
• the fuel additive or lubricating oil additive of this disclosure may be an aromatic amine, a substituted aromatic amine, or a derivative thereof, or an acceptable salt thereof.
• Aromatic amine additives can have the generalized structure shown in Formula 11-1 or 11-2, wherein R is independently one or more H or C 1 -C 20 alkyl group and X is N (e.g., R-N-R) or O - .
• secondary LSPI-reducing additives that can be utilized as fuel or lubricating additives to reduce LSPI activity.
• a secondary LSPI-reducing additive, a substituted secondary LSPI-reducing additive, or a derivative thereof will be used in their salt form and in combination with a primary additive to reduce LSPI activity.
• ⁇ -amino alkanol (primary additive) and aliphatic acid (secondary additive) can be combined and utilized as an LSPI additive.
• Table 2 lists the secondary additive types. Some additives can act as a primary additive and/or secondary additive.
• Aliphatic acids are non-aromatic carboxylic acids. Suitable aliphatic acids include mono-carboxylic acids having the following structure wherein R is an aliphatic group having between 2 to 20 carbon atoms. The aliphatic group may be linear or branched and may contain heteroatoms.
• Suitable aliphatic acids include hexanoic acid ( Formula 13A ), heptanoic acid ( Formula 13B ), octanoic acid ( Formula 13C ), nonanoic acid ( Formula 13D ), decanoic 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 ), 3,3-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 ),
• Suitable unsaturated acids include any organic acids that contain double or triple carbon-carbon bond.
• Representative unsaturated acids include maleic acid ( Formula 14A ), fumaric acid ( Formula 14B ), as well as unsaturated fatty acids such as palmitoleic acid ( Formula 14C ) and oleic acid ( Formula 14D ). Representative structures are shown below.
• Suitable alkylaromatic acids include both mono-carboxylic acids and dicarboxylic acids.
• the alkyl carboxylic acid may 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 hydroxy, alkoxy and carbonyl (e.g., aldehydic or ketonic) groups.
• Suitable examples of alkylaromatic acid include methylbenzoic acid ( Formula 15A ) and ethylbenzoic acid ( Formula 15B ). Representative structures are shown below.
• Suitable aromatic acids include both mono-carboxylic acids and dicarboxylic acids.
• the alkyl carboxylic acid may 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 hydroxy, alkoxy and carbonyl (e.g., aldehydic or ketonic) groups.
• Suitable aromatic acids include benzoic acid ( Formula 16A ), hydroxybenzoic acid ( Formula 16B ), and tetralin carboxylic acid ( Formula 16C ). Representative structures are shown below.
• Suitable examples of hydroxy acid 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 can be utilized as primary and/or secondary additives. Suitable amino acids were previously described above.
• Suitable phenols include, thymol ( Formula 18A ), eugenol ( Formula 18B ), hydroquinone ( Formula 18C ), resorcinol ( Formula 18D ), cresol ( Formula 18E ) and 2-methylquinolin-8-ol ( Formula 18G ). Representative structures are shown below.
• 1,3 diketone compounds include acetylacetone ( Formula 19A ), , and curcumin ( Formula 19B ). Representative structures are shown below.
• Base oils for use in the lubricating oil compositions of present disclosure are any of the variety of oils corresponding to API Group I, Group II, Group III, Group IV, and Group V oils, and mixtures thereof, preferably API Group II, Group III, Group IV, and Group V oils, and mixtures thereof, more preferably the Group III to Group V base oils due to their exceptional volatility, stability, viscometric and cleanliness features.
• test compounds were blended in gasoline or lube oil and their capacity for reducing LSPI events were determined using the test method described below.
• a GM 2.0 L LHU 4-cylinder gasoline turbocharged direct-injected engine was used for LSPI testing. Each cylinder was equipped with a combustion pressure sensor.
• LSPI-impacted combustion cycles were determined by monitoring peak cylinder pressure (PP) and crank angle at 5% total heat release (AI5). LSPI-impacted combustion cycles are defined as having both (1) a PP greater than five standard deviations than the average PP for a given cylinder and truncated segment and (2) an AI5 greater than five standard deviations less than the average for a given cylinder and truncated segment.

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