WO2019180685A1 - 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 PDF

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Publication number
WO2019180685A1
WO2019180685A1 PCT/IB2019/052366 IB2019052366W WO2019180685A1 WO 2019180685 A1 WO2019180685 A1 WO 2019180685A1 IB 2019052366 W IB2019052366 W IB 2019052366W WO 2019180685 A1 WO2019180685 A1 WO 2019180685A1
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WIPO (PCT)
Prior art keywords
additive
acid
formula
amino
fuel
Prior art date
Application number
PCT/IB2019/052366
Other languages
English (en)
French (fr)
Inventor
Richard Eugene CHERPECK
Amir Gamal MARIA
Ian G. ELLIOTT
Theresa Liang GUNAWAN
Original Assignee
Chevron Oronite Company Llc
Chevron U.S.A. Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chevron Oronite Company Llc, Chevron U.S.A. Inc. filed Critical Chevron Oronite Company Llc
Priority to CA3094919A priority Critical patent/CA3094919A1/en
Priority to MX2020009860A priority patent/MX2020009860A/es
Priority to SG11202009214RA priority patent/SG11202009214RA/en
Priority to CN201980026598.2A priority patent/CN112055742A/zh
Priority to JP2020550739A priority patent/JP2021518470A/ja
Priority to EP19721765.6A priority patent/EP3768807A1/en
Priority to KR1020207029541A priority patent/KR20200135408A/ko
Priority to AU2019240290A priority patent/AU2019240290A1/en
Publication of WO2019180685A1 publication Critical patent/WO2019180685A1/en
Priority to ZA2020/06130A priority patent/ZA202006130B/en
Priority to CONC2020/0013036A priority patent/CO2020013036A2/es

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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.
  • LSPI primary low-speed pre-ignition
  • X1 and X2 are independently H, C, N,
  • X1 or X2 independently includes one or more C1-C20 alkyl group or one or more aromatic group.
  • X1 and X2 are independently H, C, N, O, or S; and wherein
  • Xi or X2 independently includes one or more C1 -C20 alkyl group or one or more aromatic group.
  • motif additive having a structure of , wherein Xi and X 2 are independently H, C, N, O, or S; and wherein Xi or X 2 independently includes one or more Ci -C 2 o alkyl group or one or more aromatic group.
  • gasoline or gasoline boiling range components refers to a composition containing at least predominantly C 4 -Ci 2 hydrocarbons.
  • gasoline or gasoline boiling range components is further defined to refer to a composition containing at least predominantly C 4 -Ci 2 hydrocarbons and further having a boiling range of from about 100°F (37.8°C) to about 400°F (204°C).
  • gasoline or gasoline boiling range components is defined to refer to a composition containing at least predominantly C 4 -Ci 2 hydrocarbons, having a boiling range of from about 100°F (37.8°C) to about 400°F (204°C), and further defined to meet ASTM D4814.
  • diesel refers to middle distillate fuels containing at least predominantly Cio-C 2 s hydrocarbons.
  • diesel is further defined to refer to a composition containing at least predominantly Cio-C 2 s hydrocarbons, and further having a boiling range of from about 165.6°C (330°F) to about 371.1°C (700°F).
  • diesel is as defined above to refer to a composition containing at least predominantly C10-C25 hydrocarbons, having a boiling range of from about 165.6°C (330°F) to about 371.1°C (700°F), and further defined to meet ASTM D975.
  • oil soluble means that for a given additive, the amount needed to provide the desired level of activity or performance can be incorporated by being dissolved, dispersed or suspended in an oil of lubricating viscosity. Usually, this means that at least 0.001 % by weight of the additive can be incorporated in a lubricating oil composition.
  • fuel soluble is an analogous expression for additives dissolved, dispersed or suspended in fuel.
  • alkyl refers to saturated hydrocarbon groups, which can be linear, branched, cyclic, or a combination of cyclic, linear and/or branched.
  • alkanol is an alkyl group, as described herein, having a hydroxy substituent (i.e., an— OH group).
  • 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.
  • An "analog” is a compound having a structure similar to another compound but differing from it in respect to a certain component such as one or more atoms, functional groups, substructures, which are replaced with other atoms, groups, or substructures.
  • a "homolog” is a compound 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 because they differ only in the length of a repeating unit (-CH2-). A homolog may be considered a specific type of analog.
  • a “derivative” is a compound that is derived from a similar compound via a chemical reaction (e.g., acid-base reaction, hydrogenation, etc.).
  • a derivative may be a combination of one or more moiety.
  • a phenol moiety may be considered a derivative of aryl moiety and hydroxyl moiety.
  • a person of ordinary skill in the related art would know the metes and bounds of what is considered a derivative.
  • substituted refers to a substitution or replacement of an atom or atoms of a compound.
  • a “substituted alkyl group” may refer to, among other things, an ethanol.
  • An “engine” or a “combustion engine” is a heat engine where the combustion of fuel occurs in a combustion chamber.
  • An “internal combustion engine” is a heat engine where the combustion of fuel occurs in a confined space ("combustion chamber”).
  • a “spark ignition engine” is a heat engine where the combustion is ignited by a spark, usually from a spark plug. This is contrast to a “compression-ignition engine,” typically a diesel engine, where the heat generated from compression together with injection of fuel is sufficient to initiate combustion without an external spark.
  • 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.
  • the fuel additive or lubricating oil additive of this disclosure may be a b- amino alkanol, a substituted b-amino alkanol, a derivative thereof or an acceptable salt thereof.
  • Useful b-amino alkanols include those that can be represented by the following general formula:
  • Ri, R 2 , R 3 , and R4 are each independently selected from hydrogen and a C 1 - C 20 alkyl (e.g., Ci-C 6 alkyl) group; and two or more of R1, R 2 , R 3 , and R4 optionally can be bonded together to form a ring structure (e.g., a five-, six-, or seven-membered ring).
  • R1, R 2 , R 3 , and R4 may independently include one or more aromatic rings.
  • the b-amino alkanol has at least 2 carbon atoms (e.g., from 4 to 30 carbon atoms, from 4 to 20 carbon atoms, from 4 to 16 carbon atoms, from 4 to 12 carbon atoms, from 5 to 30 carbon atoms, from 5 to 20 carbon atoms, from 5 to 16 carbon atoms, or from 5 to 12 carbon atoms).
  • Suitable b-amino alkanols include ethanolamine (Formula 1A), 1 -amino-2-propanol (Formula 1 B), alaninol (Formula 1C), 2-(methylamino)ethanol (Formula 1 D), 2-(ethylamino)ethanol (Formula 1 E), 2- amino-2-methyl-1 -propanol (Formula 1 F), 2-amino-1 -butanol (Formula 1G), 2- amino-1 -pentanol (Formula 1 H), valinol (Formula 11), 2-amino-1 -hexanol (Formula U), leucinol (Formula 1 K), isoleucinol (Formula 1 L), cycloleucinol (Formula 1 M), cyclohexylglycinol (Formula 1 N), prolinol (Formula 10), 2-(hydroxymethyl)piperidine (Formula 1A), 1
  • the fuel additive or lubricating oil additive of this disclosure may be an aliphatic amino acid, a substituted aliphatic amino acid, or a derivative thereof, or an acceptable salt thereof.
  • Useful amino acids include those that can be represented by the following general formula:
  • R is an "aliphatic” or "aromatic” side chain.
  • Amino acid side chains can be broadly classified as aromatic or aliphatic.
  • An aromatic side chain includes an aromatic ring.
  • Examples of amino acids with aromatic side chains include for example, histidine (Formula 2A), phenylalanine (Formula 2B), tyrosine (Formula 2C), tryptophan (Formula 2D) and the like.
  • Non-aromatic side chains are broadly grouped as "aliphatic” and include, for example, alanine (Formula 2E), glycine (Formula 2F), cysteine (Formula 2G), and the like.
  • the amino acid(s) can be natural and/or non-natural cc-amino acids. Natural amino acids are those encoded by the genetic code, as well as amino acids derived therefrom. These include, for example, hydroxyproline (Formula 2H), g- carboxyglutamate (Formula 21), and citrulline (Formula 2J).
  • amino acid also includes amino acid analogs and mimetics. Analogs are compounds having the same general structure of a natural amino acid, except that the R group is not one found among the natural amino acids.
  • amino acid mimetic is a compound that has a structure different from the general chemical structure of an a-amino acid but functions in a manner similar to one.
  • the amino acid may be an L- or D-amino acid. Representative structures are shown below.
  • the fuel additive or lubricating oil additive of this disclosure may be an amino ester, a substituted amino ester, or a derivative thereof, or an acceptable salt thereof.
  • Amino esters can be derived from amino acids (as described above) and alcohols. Amino esters and amino acids may be considered derivatives of each other.
  • Useful amino esters include those that can be represented by the following general formula:
  • R is an aliphatic side chain and Ri is a carbon chain 1 to 20 carbon atoms in length, preferably 1 to 4 carbon atoms, in particular, methanol or ethanol, preferably methanol.
  • the amino esters may include aromatic or aliphatic side chains.
  • Representative examples of amino esters include methyl alaninate (Formula 3A), ethyl alaninate (Formula 3B), methyl glycinate (Formula 3C), and ethyl glycinate (Formula 3D). Representative structures are shown below.
  • X1 and X2 may include a cyclic structure (e.g., a five-, six-, or seven-membered ring). Cyclic structures may be aromatic or non-aromatic, as well as vary from being fully saturated to fully unsaturated. Suitable examples of additives compatible with Formula 4 include amidines, guanidines, imidazoles, benzamidines, benzimidazoles, and aminobenzimidazoles.
  • the fuel additive or lubricating oil additive of this disclosure may be an amidine, a substituted amidine, or a derivative thereof or an acceptable salt thereof.
  • Useful amidines include those that can be represented by the following general formula:
  • R 3 ⁇ 4 , R 6 , R7 and Rs 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 3 ⁇ 4 , R 6 , R7 and Rs 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 unsaturated.
  • the organic and heterorganic groups may have from 1 to 10 carbon atoms (e.g., 1 to 6 carbon atoms).
  • 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]-undeca-7- ene (DBU; Formula 5E), benzamidine (Formula 5F), benzimidazole (Formula 5G) and 2-phenyl-1 H-benzo[d]imidazole (Formula 5M). Representative structures are shown below.
  • 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,
  • Rg, R10, Rn, R12 and R13 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 Rg, R10, R11, R12 and R13 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 unsaturated.
  • the organic and heterorganic groups may have from 1 to 10 carbon atoms (e.g., 1 to 6 carbon atoms).
  • 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]dec-5-ene (TBD; Formula 6C), 7-methyl- 1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD; Formula 6D) and 1,2-diphenylguanidine (Formula 61). Representative structures shown below.
  • the fuel additive or lubricating oil additive of this disclosure may be an imidazole, a substituted imidazole, or a derivative thereof, or an acceptable salt thereof.
  • Suitable imidazoles include imidazole (Formula 7 A), 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 71), 1,2-dimethylimidazole (Formula 7J), 2-ethyl-4(5)- methylimidazole (Formula 7K), and 1 -vin
  • the fuel additive or lubricating oil additive of this disclosure may be a triazole, a substituted triazole, or a derivative thereof, or an acceptable salt thereof.
  • Suitable triazoles include 1, 2, 3-triazole (Formula 8A), 5,6-dimethylbenzotriazole (Formula 8B), and 1, 2, 4-triazole (Formula 8C). Representative structures are shown below.
  • 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 Ri, R 2 , and R 3 are independently C1-C20 alkyl groups.
  • Suitable benzamidiniums include N,N-dimethyl-N-octylbenzamidium-2- oxide (Formula 9A). Representative structures are shown below.
  • the fuel additive or lubricating oil additive of this disclosure may be a benzoxazole, a substituted benzoxazole, or a derivative thereof, or an acceptable salt thereof.
  • Suitable benzoxazoles include benzoxazole (Formula 10A) and 2- aminobenzoxazole (Formula 10B). Representative structures are shown below.
  • 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 1 1 -1 or 1 1 -2,
  • Formula 11-1 Formula 11-2 wherein R is independently one or more H or C1-C20 alkyl group and X is N (e.g., R-N- R) or O .
  • Suitable aromatic amines include 2-methylquinolin-8-amine (Formula 11 A). Representative structures are shown below.
  • 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.
  • b-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
  • 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 (C20), behenic acid (C22), 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 (Cs), 2-ethylhexanoic acid (Formula 13G), 2-methylhepta
  • 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 hydroxy acids include those that can be represented by the following general formula:
  • Formula 17 wherein n 1 to 3.
  • 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.
  • Suitable examples of 1,3 diketone compounds include acetylacetone (Formula 19A), , and curcumin (Formula 19B). Representative structures are shown below.
  • a hydroxamide is a hydroxy derivative of an amide.
  • Useful hydroxamides include those that can be represented by the following general formula:
  • Ri and R 2 are each independently selected from hydrogen or Ci-C2o (e.g., C3- C12) alkyl group.
  • Suitable hydroxamide includes hydroxy methylacetamide (Formula 21A). Representative structures are shown below.
  • Suitable antioxidants 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 antioxidants include the following.
  • Suitable salicylates include 2-hydroxy-5-(tetracosa-
  • the salts of this disclosure may be prepared by conventional means, for example, by mixing the primary additive with a suitable secondary additive in an aprotic solvent. The order in which one additive is added to the other is not important.
  • the primary additive and secondary additive are usually mixed together in an approximately equimolar ratio. An excess of the primary or secondary additive component may be used.
  • the molar ratio of base relative to the alkyl carboxylic acid may be about 1.05:1 to 2:1 (e.g., 1.1 :1 to 1.5:1). Representative salts are shown below.
  • the compounds of the present disclosure may be useful 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 disclosure in hydrocarbon fuel may range from 25 to 5000 parts per million (ppm) by weight (e.g., 50 to 1000 ppm).
  • the compounds of the present disclosure may be formulated as a concentrate using an inert stable oleophilic (i.e., soluble in hydrocarbon fuel) organic solvent boiling in a range of 65°C to 205°C.
  • An aliphatic or an aromatic hydrocarbon solvent may be used, such as benzene, toluene, xylene, or higher-boiling aromatics or aromatic thinners.
  • Aliphatic alcohols containing 2 to 8 carbon atoms, such as ethanol, isopropanol, methyl isobutyl carbinol, n-butanol and the like, in combination with the hydrocarbon solvents are also suitable for use with the present additives.
  • the amount of the additive may range from 10 to 70 wt % (e.g., 20 to 40 wt %).
  • gasoline fuels other well-known additives can be employed including oxygenates (e.g., ethanol, methyl tert- butyl ether), other anti-knock agents, and detergents/dispersants (e.g., hydrocarbyl amines, hydrocarbyl poly(oxyalkylene) amines, succinimides, Mannich reaction products, aromatic esters of polyalkylphenoxyalkanols, or polyalkylphenoxyaminoalkanes). Additionally, friction modifiers, antioxidants, metal deactivators and demulsifiers may be present.
  • oxygenates e.g., ethanol, methyl tert- butyl ether
  • detergents/dispersants e.g., hydrocarbyl amines, hydrocarbyl poly(oxyalkylene) amines, succinimides, Mannich reaction products, aromatic esters of polyalkylphenoxyalkanols, or polyalkylphenoxyaminoalkanes.
  • diesel fuels other well-known additives can be employed, such as pour point depressants, flow improvers, cetane improvers, and the like.
  • a fuel-soluble, non-volatile carrier fluid or oil may also be used with compounds of this disclosure.
  • the carrier fluid is a chemically inert hydrocarbon- soluble liquid vehicle which substantially increases the non-volatile residue (NVR), or solvent-free liquid fraction of the fuel additive composition while not overwhelmingly contributing to octane requirement increase.
  • the carrier fluid may be a natural or synthetic oil, such as mineral oil, refined petroleum oils, synthetic polyalkanes and alkenes, including hydrogenated and unhydrogenated polyalphaolefins, synthetic polyoxyalkylene-derived oils, such as those described in U.S. Patent Nos. 3,756,793; 4,191,537; and 5,004,478; and in European Patent Appl. Pub. Nos. 356,726 and 382,159.
  • the carrier fluids may be employed in amounts ranging from 35 to 5000 ppm by weight of the hydrocarbon fuel (e.g., 50 to 3000 ppm of the fuel). When employed in a fuel concentrate, carrier fluids may be present in amounts ranging from 20 to 60 wt % (e.g., 30 to 50 wt %).
  • the compounds of the present disclosure may be 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 disclosure in the lubricating oil composition may range from 0.01 to 15 wt % (e.g., 0.5 to 5 wt %), based on the total weight of the lubricating oil composition.
  • the oil of lubricating viscosity (sometimes referred to as “base stock” or “base oil”) is the primary liquid constituent of a lubricant, into which additives and possibly other oils are blended, for example to produce a final lubricant (or lubricant composition).
  • a base oil which is useful for making concentrates as well as for making lubricating oil compositions therefrom, may be selected from natural (vegetable, animal or mineral) and synthetic lubricating oils and mixtures thereof.
  • base stocks and base oils in this disclosure are the same as those found in American Petroleum Institute (API) Publication 1509 Annex E ("API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils," December 2016).
  • Group I base stocks contain less than 90% saturates and/or greater than 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
  • Group II base stocks contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
  • Group III base stocks contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 120 using the test methods specified in Table E-1.
  • Group IV base stocks are polyalphaolefins (PAO).
  • 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 possessing favorable thermal oxidative stability can be used. Of the natural oils, mineral oils are preferred. Mineral oils vary widely as to their crude source, for example, as to whether they are paraffinic, naphthenic, or mixed paraffinic-naphthenic. Oils derived from coal or shale are also useful. Natural oils vary also as to the method used for their production and purification, for example, their distillation range and whether they are straight run or cracked, hydrorefined, or solvent extracted.
  • Synthetic oils include hydrocarbon oil.
  • Hydrocarbon oils include oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylene- alphaolefin copolymers).
  • Polyalphaolefin (PAO) oil base stocks are commonly used synthetic hydrocarbon oil.
  • PAOs derived from Cs to Ci 4 olefins e.g., C 3 ⁇ 4 C10, C12, Cu olefins or mixtures thereof, may be utilized.
  • base oils include non-conventional or unconventional base stocks that have been processed, preferably catalytically, or synthesized to provide high performance characteristics.
  • Non-conventional or unconventional base stocks/base oils include one or more of a mixture of base stock(s) derived from one or more Gas-to-Liquids (GTL) materials, as well as isomerate/isodewaxate base stock(s) derived from natural wax or waxy feeds, mineral and or non-mineral oil waxy feed stocks such as slack waxes, natural waxes, and waxy stocks such as gas oils, waxy fuels hydrocracker bottoms, waxy raffinate, hydrocrackate, thermal crackates, or other mineral, mineral oil, or even non- petroleum oil derived waxy materials such as waxy materials received from coal liquefaction or shale oil, and mixtures of such base stocks.
  • GTL Gas-to-Liquids
  • 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.
  • the base oil will have a kinematic viscosity at 100°C (ASTM D445) in a range of 2.5 to 20 mm 2 /s (e.g., 3 to 12 mm 2 /s, 4 to 10 mm 2 /s, or 4.5 to 8 mm 2 /s).
  • the present lubricating oil compositions may also contain conventional lubricant additives for imparting auxiliary functions to give a finished lubricating oil composition in which these additives are dispersed or dissolved.
  • the lubricating oil compositions can be blended 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 compatibilizers, corrosion-inhibitors, dyes, extreme pressure agents and the like and mixtures thereof.
  • a variety of the additives are known and commercially available. These additives, or their analogous compounds, can be employed for the preparation of the lubricating oil compositions of the invention by the usual blending procedures.
  • each of the foregoing additives when used, is used at a functionally effective amount to impart the desired properties to the lubricant.
  • a functionally effective amount of this ashless dispersant would be an amount sufficient to impart the desired dispersancy characteristics to the lubricant.
  • the concentration of each of these additives, when used may range, unless otherwise specified, from about 0.001 to about 20 wt %, such as about 0.01 to about 10 wt %.
  • 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.
  • a six-segment test procedure was used to determine the number of LSPI events that occurred under conditions of an engine speed of 2000 rpm and a load of 275 Nm.
  • the LSPI test condition is run for 28 minutes with each segment separated by an idle period.
  • the first segment is used to condition the oil and the number of LSPI events are not counted.
  • Each segment is slightly truncated to eliminate the transient portion.
  • Each truncated segment typically has approximately 100,000 combustion cycles (25,000 combustion cycles per cylinder).
  • the five truncated segments where LSPI events are counted have approximately 500,000 combustion cycles (125,000 combustion cycles per cylinder). There may be instances of shortened tests in the event the engine cannot complete all six segments.
  • 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.
  • LSPI Frequency [(Total Number of LSPI Impacted Combustion Cycles in five Truncated Segments)/(Total Number of Combustion Cycles In five Truncated Segments )] c 1,000,000
  • An additive associated with a test fuel and/or test lubricant that reduces the LSPI frequency, when compared to the corresponding baseline fuel and/or baseline lubricant, is considered an additive that mitigates LSPI frequency.
  • the baseline fuel was a conventional 49-state premium unleaded gasoline fuel without any deposit control additives and the baseline lubricant was representative of a conventional engine oil meeting ILSAC GF-5 and API SN specifications.
  • tetralin was added to the gasoline to promote LSPI.
  • Table 2 The test results are set forth in Table 2.

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PCT/IB2019/052366 2018-03-23 2019-03-22 Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines WO2019180685A1 (en)

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Application Number Priority Date Filing Date Title
CA3094919A CA3094919A1 (en) 2018-03-23 2019-03-22 Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines
MX2020009860A MX2020009860A (es) 2018-03-23 2019-03-22 Composicion y metodo para prevenir o reducir la pre-ignicion de baja velocidad en motores de combustion interna encendidos por chispa.
SG11202009214RA SG11202009214RA (en) 2018-03-23 2019-03-22 Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines
CN201980026598.2A CN112055742A (zh) 2018-03-23 2019-03-22 在火花点火式内燃发动机中预防或减少低速早燃的组合物和方法
JP2020550739A JP2021518470A (ja) 2018-03-23 2019-03-22 火花点火内燃機関の低速予備点火を防止または低減するための組成物および方法
EP19721765.6A EP3768807A1 (en) 2018-03-23 2019-03-22 Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines
KR1020207029541A KR20200135408A (ko) 2018-03-23 2019-03-22 스파크-점화된 내연기관용 엔진에서 저속 조기-점화를 방지 또는 감소시키기 위한 조성물 및 방법
AU2019240290A AU2019240290A1 (en) 2018-03-23 2019-03-22 Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines
ZA2020/06130A ZA202006130B (en) 2018-03-23 2020-10-02 Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines
CONC2020/0013036A CO2020013036A2 (es) 2018-03-23 2020-10-19 Composición y método para prevenir o reducir el preencendido a baja velocidad en motores de combustión interna encendidos por chispa

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