EP0798364A1 - Diesel fuel additives and diesel fuel composition - Google Patents
Diesel fuel additives and diesel fuel composition Download PDFInfo
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- EP0798364A1 EP0798364A1 EP97302039A EP97302039A EP0798364A1 EP 0798364 A1 EP0798364 A1 EP 0798364A1 EP 97302039 A EP97302039 A EP 97302039A EP 97302039 A EP97302039 A EP 97302039A EP 0798364 A1 EP0798364 A1 EP 0798364A1
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- Prior art keywords
- diesel fuel
- additive
- diesel
- fuel
- composition
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Classifications
-
- 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
-
- 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
- C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
-
- 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
-
- 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
- C10L1/224—Amides; Imides carboxylic acid amides, imides
-
- 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
-
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/188—Carboxylic acids; metal salts thereof
- C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
-
- 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
- C10L1/18—Organic compounds containing oxygen
- 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
-
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
-
- 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
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
Definitions
- the present invention relates to a diesel fuel additive and a diesel fuel composition, and particularly to a diesel fuel additive which is effective in reducing an amount of deposit on an injection nozzle of a compression-ignition diesel engine, increasing lubricity of the diesel fuel, and reducing wear of a fuel injection pump in the engine, and a diesel fuel composition containing the diesel fuel additive.
- a diesel fuel additive particularly for diesel fuels of low sulfur content, that can reduce the production of deposits on fuel injection nozzles of compression-ignition diesel engines, improve the lubricity of diesel fuel, and further keep the fuel injection pump from wear.
- the present invention resides in a diesel fuel additive comprising a salt of a carboxylic acid and an aliphatic amine, or an amide obtainable by dehydration-condensation between a carboxylic acid and an aliphatic amine.
- the diesel fuel additive of the invention can be employed by blending into a diesel fuel, particularly, a diesel fuel of low sulfur content, in an amount of, generally, not more than 1 weight %, preferably 30 to 300 ppm.
- the carboxylic acid is represented by the formula: R(COOH) n wherein R represents a hydrocarbyl group having 2 to 50 carbon atoms, and n represents an integer of 1 to 4.
- the carboxylic acid may be a monocarboxylic acid having 8 to 30 carbon atoms, such as oleic acid.
- the aliphatic amine may comprise a hydrocarbyl group having 2 to 50 carbon atoms and 1 to 10 amine nitrogen atoms.
- the aliphatic amine may be a mono-amine which comprises a hydrocarbyl group having 8 to 20 carbon atoms.
- the aliphatic amine may be propylene diamine to which a hydrocarbyl group having 8 to 20 carbon atoms is attached. Specific examples are of aliphatic amines which may be used in the invention are oleyl amine and oleyl propylene diamine.
- diesel fuel for which the invention is employable.
- the invention is preferably applied to diesel fuel, that is, a certain petroleum distillate, having a sulfur content of not more than 0.2 weight %, particularly not more than 0.05 weight %.
- diesel fuels to which the invention is applicable are those defined in JIS K 2204, Nos. 1 to 3, particularly, No. 3, which are treated to reduce the sulfur content to have the above content.
- the salt of a carboxylic acid and an aliphatic amine can be obtained by mixing the carboxylic acid and the aliphatic amine at a temperature of 20 to 100°C.
- the amide can be obtained by subjecting a mixture of the carboxylic acid and the aliphatic amine to dehydration reaction at a temperature of 20 to 200°C under atmospheric or reduced pressure.
- the carboxylic acid to be employed in the invention preferably is a compound which is represented by the formula: R(COOH) n wherein R represents a hydrocarbyl group having 2 to 50 carbon atoms, and n represents an integer of 1 to 4.
- the preferred hydrocarbyl groups are aliphatic groups such as an alkyl group and an alkenyl group, which may have a straight chain or a branched chain.
- preferred carboxylic acids are aliphatic acids having 8 to 30 carbon atoms and include capric acid, lauric acid, myristic acid, stearic acid, isostearic acid, arachic acid, behenic acid, lignoceric acid, cerotic acid, montanic acid, melissic acid, caproleic acid, oleic acid, eraidic acid, linolic acid, linoleic acid, fatty acid of coconut oil, fatty acid of hardened fish oil, fatty acid of hardened rapeseed oil, fatty acid of hardened tallow oil, and fatty acid of hardened palm oil.
- the examples further include dodecenyl succinic acid and its anhydride.
- the aliphatic amine preferably has a hydrocarbyl group of 2 to 50 carbon atoms in one molecule and amine nitrogen atoms of 1 to 10.
- Preferred are monoamines and diamines having a hydrocarbyl group of 8 to 20 carbon atoms. Their examples include coconut amine, capric amine, myristyl amine, stearyl amine, oleyl amine, tallow oil amine, stearyl propylene diamine, tallow oil diamine, and oleyl propylene diamine.
- polyamines having a hydrocarbyl group of 5 to 50 carbon atoms such as ethylenediamine, diethylenetriamine, triethylene-tetramine, tetraethylenepentamine, and pentaethylene-hexamine.
- the ratio of amount of the aliphatic amine to the carboxylic acid in the diesel fuel additive of the invention may be varied from 0.5 to 1.5 equivalents to one equivalent of the carboxylic acid.
- the diesel fuel additive may contain unreacted or unnuetrualized carboxylic acid or aliphatic amine within the range.
- the additive of (1) the salt of carboxylic acid and aliphatic amine, or (2) the amide produced by dehydration-condensation of the carboxylic acid and aliphatic amine can be incorporated into diesel fuel in optionally adopted manner to prepare the diesel fuel composition of the invention.
- Two or more additives can be added to a diesel fuel separately or in admixture.
- the additive can be previously diluted with a small amount of a diluent oil such as kerosine, diesel fuel, or an aromatic solvent to give a concentrated additive solution and the concentrated additive solution can be incorporated into the diesel fuel to be treated.
- the diesel fuel additive of the invention can be mixed with a diluent to give a concentrated additive solution containing 1 to 70 weight percent of the diesel additive, and the thus obtained concentrated solution can then be diluted with the diesel fuel to be treated.
- the incorporation of the additive of the invention that is, the salt of carboxylic acid and aliphatic amine or the amide obtained therefrom, into diesel fuel in an amount of the specific range reduces the friction of the diesel fuel, keeps the diesel engine from wrong rotation, and obviates wear of the fuel injection pump.
- the amount of the diesel fuel additive of the invention generally is in the range of 10 ppm to 1 weight % of the diesel fuel, preferably 30 to 300 ppm.
- the diesel fuel additive of the invention can be employed in combination with other diesel fuel additives such as low-temperature pour point depressant, cetane improver, anti-oxidants, metal deactivators, rust-inhibitors, corrosion inhibitors, demulsifiers and foam inhibitors, in the conventionally adopted amounts.
- diesel fuel additives such as low-temperature pour point depressant, cetane improver, anti-oxidants, metal deactivators, rust-inhibitors, corrosion inhibitors, demulsifiers and foam inhibitors, in the conventionally adopted amounts.
- the above mentioned diesel fuel additive was incorporated into the aforementioned diesel fuel to give the following diesel fuel composition.
- the diesel fuel compositions prepared as above were evaluated on their lubricity characteristics by the following HFRR test.
- Coordinating European Council tentatively has determined HFRR Test (High Frequency Reciprocating Rig Test) in CEC-F-06-T94 as a standard for evaluating lubricity and anti-wear characteristic of a diesel fuel and diesel fuel additive which are designed to reduce wear of the fuel injection pump of diesel engine due to poor lubrication of diesel fuel.
- HFRR Test High Frequency Reciprocating Rig Test
- test piece is mounted on an electromagnetic vibrator which vibrates within a small amplitude. This test piece is pushed against another test piece which is fixed at its bottom portion. The friction and a diameter of wear area are then measured. The test temperature, frequency, amplitude of the vibration, and weight are optionally varied.
- a flow rate through a new nozzle was measured using a flow meter set according to ISO 4010 before the following operation was started.
- Nissan SD-22 engine (indirect injection type, nozzle type: throttle type, displacement: 2,164 cc) was run at a constant rate of an engine revolution of 4,000 r.p.m., torque of 50Nm for 6 hours. After the run was complete, the flow rate through the nozzle was measured by the above described method. The measured flow rate was compared with the flow rate measured on the new nozzle to evaluate the amount of deposit on the nozzle.
- the diesel fuel additive of the invention When the diesel fuel additive of the invention is incorporated into a diesel fuel, particularly a diesel fuel containing a less amount of sulfur, the additive is effective to reduce the amount of deposit in the injection nozzle of a diesel engine of a pressure ignition type, improve lubricity of the diesel fuel, and reduce wear of the fuel injection pump.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
Abstract
Description
- The present invention relates to a diesel fuel additive and a diesel fuel composition, and particularly to a diesel fuel additive which is effective in reducing an amount of deposit on an injection nozzle of a compression-ignition diesel engine, increasing lubricity of the diesel fuel, and reducing wear of a fuel injection pump in the engine, and a diesel fuel composition containing the diesel fuel additive.
- Recently, since much attention has been paid to environmental problems on earth, various countries have pushed forward with the enhancement of regulations on exhaust gas produced by diesel engine cars and reduction of sulfur content of diesel fuel. Most regulations have a target to reduce the sulfur content to less than 0.05 weight % (less than 0.05 mass %). In Japan, the sulfur content of diesel fuel has already been regulated to be less than 0.2 weight %, since October of 1992. As from 1997, the sulfur content shall be regulated to be less than 0.05 weight %.
- The reduction of the sulfur content results in reduction of sulphuric acid particulates in exhaust gas of diesel engine cars. It is reported, however, that an amount of emitted products such as particulates are also effected, that is, increased, by formation of deposits on the fuel injection nozzle. Further reported is that deposits on the injection nozzle also causes other adverse problems such as increase of black smoke and decrease of fuel economy. Therefore, it is now required to develop a detergent for injection nozzle, from viewpoints of protection of environment and resource.
- The reduction of sulfur content in diesel fuel goes ahead in the United States of America and European countries. In these countries, it is reported that the reduction of sulfur content may cause abnormal wear of the fuel injection pump, and troublesome engine operations. These problems are considered to be caused by decrease of lubricity of the diesel fuel of low sulfur content. The decrease of lubricity of the diesel fuel is thought to be caused by removal of lubricants of natural origin when the diesel fuel is desulfurized in the hydrogenating desulfurization process.
- For the above reasons, it is required to provide an additive which is able to give to the diesel fuel of low sulfur content an anti-wear property and an improved friction property of the same level as that observed in the use of the conventionally employed diesel fuels. The improvement of anti-wear property and friction property is also of value for diesel fuels of not sufficiently desulfurized.
- Accordingly, it is required to provide a diesel fuel additive, particularly for diesel fuels of low sulfur content, that can reduce the production of deposits on fuel injection nozzles of compression-ignition diesel engines, improve the lubricity of diesel fuel, and further keep the fuel injection pump from wear.
- The present invention resides in a diesel fuel additive comprising a salt of a carboxylic acid and an aliphatic amine, or an amide obtainable by dehydration-condensation between a carboxylic acid and an aliphatic amine.
- The diesel fuel additive of the invention can be employed by blending into a diesel fuel, particularly, a diesel fuel of low sulfur content, in an amount of, generally, not more than 1 weight %, preferably 30 to 300 ppm.
- Preferably, the carboxylic acid is represented by the formula:
R(COOH)n
wherein R represents a hydrocarbyl group having 2 to 50 carbon atoms, and n represents an integer of 1 to 4. For example, the carboxylic acid may be a monocarboxylic acid having 8 to 30 carbon atoms, such as oleic acid. - The aliphatic amine may comprise a hydrocarbyl group having 2 to 50 carbon atoms and 1 to 10 amine nitrogen atoms. For example, the aliphatic amine may be a mono-amine which comprises a hydrocarbyl group having 8 to 20 carbon atoms. The aliphatic amine may be propylene diamine to which a hydrocarbyl group having 8 to 20 carbon atoms is attached. Specific examples are of aliphatic amines which may be used in the invention are oleyl amine and oleyl propylene diamine.
- There are no specific limitations with respect to diesel fuel for which the invention is employable. However, the invention is preferably applied to diesel fuel, that is, a certain petroleum distillate, having a sulfur content of not more than 0.2 weight %, particularly not more than 0.05 weight %. Examples of the diesel fuels to which the invention is applicable, are those defined in JIS K 2204, Nos. 1 to 3, particularly, No. 3, which are treated to reduce the sulfur content to have the above content.
- The salt of a carboxylic acid and an aliphatic amine and their amide which are employed as the diesel fuel additives in the invention are further described.
- The salt of a carboxylic acid and an aliphatic amine can be obtained by mixing the carboxylic acid and the aliphatic amine at a temperature of 20 to 100°C. The amide can be obtained by subjecting a mixture of the carboxylic acid and the aliphatic amine to dehydration reaction at a temperature of 20 to 200°C under atmospheric or reduced pressure.
- The carboxylic acid to be employed in the invention preferably is a compound which is represented by the formula:
R(COOH)n
wherein R represents a hydrocarbyl group having 2 to 50 carbon atoms, and n represents an integer of 1 to 4. - The preferred hydrocarbyl groups are aliphatic groups such as an alkyl group and an alkenyl group, which may have a straight chain or a branched chain. Examples of preferred carboxylic acids are aliphatic acids having 8 to 30 carbon atoms and include capric acid, lauric acid, myristic acid, stearic acid, isostearic acid, arachic acid, behenic acid, lignoceric acid, cerotic acid, montanic acid, melissic acid, caproleic acid, oleic acid, eraidic acid, linolic acid, linoleic acid, fatty acid of coconut oil, fatty acid of hardened fish oil, fatty acid of hardened rapeseed oil, fatty acid of hardened tallow oil, and fatty acid of hardened palm oil. The examples further include dodecenyl succinic acid and its anhydride.
- The aliphatic amine preferably has a hydrocarbyl group of 2 to 50 carbon atoms in one molecule and amine nitrogen atoms of 1 to 10. Preferred are monoamines and diamines having a hydrocarbyl group of 8 to 20 carbon atoms. Their examples include coconut amine, capric amine, myristyl amine, stearyl amine, oleyl amine, tallow oil amine, stearyl propylene diamine, tallow oil diamine, and oleyl propylene diamine. Also employable are polyamines having a hydrocarbyl group of 5 to 50 carbon atoms such as ethylenediamine, diethylenetriamine, triethylene-tetramine, tetraethylenepentamine, and pentaethylene-hexamine.
- The ratio of amount of the aliphatic amine to the carboxylic acid in the diesel fuel additive of the invention may be varied from 0.5 to 1.5 equivalents to one equivalent of the carboxylic acid. The diesel fuel additive may contain unreacted or unnuetrualized carboxylic acid or aliphatic amine within the range.
- The additive of (1) the salt of carboxylic acid and aliphatic amine, or (2) the amide produced by dehydration-condensation of the carboxylic acid and aliphatic amine can be incorporated into diesel fuel in optionally adopted manner to prepare the diesel fuel composition of the invention. Two or more additives can be added to a diesel fuel separately or in admixture. The additive can be previously diluted with a small amount of a diluent oil such as kerosine, diesel fuel, or an aromatic solvent to give a concentrated additive solution and the concentrated additive solution can be incorporated into the diesel fuel to be treated. For instance, the diesel fuel additive of the invention can be mixed with a diluent to give a concentrated additive solution containing 1 to 70 weight percent of the diesel additive, and the thus obtained concentrated solution can then be diluted with the diesel fuel to be treated.
- The incorporation of the additive of the invention, that is, the salt of carboxylic acid and aliphatic amine or the amide obtained therefrom, into diesel fuel in an amount of the specific range reduces the friction of the diesel fuel, keeps the diesel engine from wrong rotation, and obviates wear of the fuel injection pump. The amount of the diesel fuel additive of the invention generally is in the range of 10 ppm to 1 weight % of the diesel fuel, preferably 30 to 300 ppm.
- The diesel fuel additive of the invention can be employed in combination with other diesel fuel additives such as low-temperature pour point depressant, cetane improver, anti-oxidants, metal deactivators, rust-inhibitors, corrosion inhibitors, demulsifiers and foam inhibitors, in the conventionally adopted amounts.
- The present invention is further described by the following non-limiting examples.
- The two diesel fuels having the following characteristics were employed.
TAble 1 Diesel fuel-A Diesel fuel-B Density (g/mL, 15°C) 0.837 0.831 Sulfur content (wt.%) 0.12 0.04 Distillation test (°C) Initial boiling 159 169 50% distillation 280 282 90% distillation 349 340 End point 356 366 Pour point (°C) -12.5 -7.5 Dynamic vis. (mm2/s, 30°C) 3.99 3.75 - The following diesel fuel additives were prepared.
- Additive-1:
- A salt of oleic acid and oleylamine in neutralizing equivalent amounts
- Additive-2:
- A salt of one equivalent amount of oleylamine and 0.8 equivalent amount of oleic acid
- Additive-3:
- A salt of oleylpropylenediamine and oleic acid in neutralizing equivalent amounts
- Additive-4:
- An amide compound obtained by dehydration between oleic acid and oleylamine in neutralizing equivalent amounts under stirring at 120°C under reduced pressure
- The above mentioned diesel fuel additive was incorporated into the aforementioned diesel fuel to give the following diesel fuel composition.
- Composition-1:
- prepared by incorporation of 50 ppm of Additive-1 into Diesel Fuel-A
- Composition-2:
- prepared by incorporation of 70 ppm of Additive-1 into Diesel Fuel-A
- Composition-3:
- prepared by incorporation of 100 ppm of Additive-1 into Diesel Fuel-A
- Composition-4:
- prepared by incorporation of 150 ppm of Additive-1 into Diesel Fuel-A
- Composition-5:
- prepared by incorporation of 100 ppm of Additive-2 into Diesel Fuel-A
- Composition-6:
- prepared by incorporation of 100 ppm of Additive-3 into Diesel Fuel-A
- Composition-7:
- prepared by incorporation of 100 ppm of Additive-4 into Diesel Fuel-A
- Composition-8:
- prepared by incorporation of 100 ppm of Additive-1 into Diesel Fuel-B
- Composition-9:
- prepared by incorporation of 100 ppm of Additive-2 into Diesel Fuel-B
- Composition-10:
- prepared by incorporation of 100 ppm of Additive-3 into Diesel Fuel-B
- Composition-11:
- prepared by incorporation of 100 ppm of Additive-4 into Diesel Fuel-B
- The diesel fuel compositions prepared as above were evaluated on their lubricity characteristics by the following HFRR test.
- Coordinating European Council tentatively has determined HFRR Test (High Frequency Reciprocating Rig Test) in CEC-F-06-T94 as a standard for evaluating lubricity and anti-wear characteristic of a diesel fuel and diesel fuel additive which are designed to reduce wear of the fuel injection pump of diesel engine due to poor lubrication of diesel fuel.
- According to HFRR test, a test piece is mounted on an electromagnetic vibrator which vibrates within a small amplitude. This test piece is pushed against another test piece which is fixed at its bottom portion. The friction and a diameter of wear area are then measured. The test temperature, frequency, amplitude of the vibration, and weight are optionally varied.
- The evaluation of the diesel fuel additive of the invention was performed according to the method stipulated in CEC-F-06-T-94. The test temperature was 60°C.
Table 2 Test Sample HFRR Test Result (60°C) Wear Diameter (mm) Diesel Fuel-A (no additive) 0.54 (control) Fuel Composition-1 0.48 Fuel Composition-2 0.44 Fuel Composition-3 0.41 Fuel Composition-4 0.36 Fuel Composition-5 0.39 Fuel Composition-6 0.41 Fuel Composition-7 0.43 Diesel Fuel-B (no additive) 0.56 (control) Fuel Composition-8 0.44 Fuel Composition-9 0.40 Fuel Composition-10 0.45 Fuel Composition-11 0.45 - The results set forth in Table 2 indicate that the fuel compositions 1 to 11 all give reduced wear size and improve anti-wear characteristic.
- A flow rate through a new nozzle was measured using a flow meter set according to ISO 4010 before the following operation was started.
- Nissan SD-22 engine (indirect injection type, nozzle type: throttle type, displacement: 2,164 cc) was run at a constant rate of an engine revolution of 4,000 r.p.m., torque of 50Nm for 6 hours. After the run was complete, the flow rate through the nozzle was measured by the above described method. The measured flow rate was compared with the flow rate measured on the new nozzle to evaluate the amount of deposit on the nozzle.
- The results are set forth in Table 3.
Table 3 Test Sample Decrease of Flow Rate (%)
(at 0.1 mm lift)Diesel Fuel-A (no additive) 73.8 Fuel Composition-3 58.4 Fuel Composition-5 55.3 Fuel Composition-6 57.6 Fuel Composition-7 59.8 - The results set forth in Table 3 indicate that the diesel fuel composition containing the fuel additive of the invention is less than the diesel fuel containing no additive in the decrease of flow rate and hence improves detergency in the injection nozzle.
- When the diesel fuel additive of the invention is incorporated into a diesel fuel, particularly a diesel fuel containing a less amount of sulfur, the additive is effective to reduce the amount of deposit in the injection nozzle of a diesel engine of a pressure ignition type, improve lubricity of the diesel fuel, and reduce wear of the fuel injection pump.
Claims (12)
- A diesel fuel additive comprising a salt of a carboxylic acid and an aliphatic amine, or an amide obtainable by dehydration-condensation between a carboxylic acid and an aliphatic amine.
- The diesel fuel additive as defined in claim 1, wherein the carboxylic acid is represented by the formula:
R(COOH)n
wherein R represents a hydrocarbyl group having 2 to 50 carbon atoms, and n represents an integer of 1 to 4. - The diesel fuel additive as defined in claim 1 or 2, wherein the carboxylic acid is a monocarboxylic acid having 8 to 30 carbon atoms.
- The diesel fuel additive as defined in any one of claims 1 to 3, wherein the aliphatic amine comprises a hydrocarbyl group having 2 to 50 carbon atoms and 1 to 10 amine nitrogen atoms.
- The diesel fuel additive as defined in any one of claims 1 to 4, wherein the aliphatic amine is a mono-amine which comprises a hydrocarbyl group having 8 to 20 carbon atoms.
- The diesel fuel additive as defined in any one of claims 1 to 5, wherein the aliphatic amine is propylene diamine to which a hydrocarbyl group having 8 to 20 carbon atoms is attached.
- The diesel fuel additive as defined in any one of claims 1 to 6, wherein the carboxylic acid is oleic acid.
- The diesel fuel additive as defined in any one of claims 1 to 7, wherein the aliphatic amine is oleyl amine or oleyl propylene diamine.
- A diesel fuel composition comprising a diesel fuel and a diesel fuel additive as claimed in any one of the preceding claims dissolved in the diesel fuel.
- The diesel fuel composition as defined in claim 9, which comprises 1 to 70 weight % of the said diesel fuel additive.
- The diesel fuel composition as defined in claim 9, which comprises 10 ppm to 1 weight % of the said diesel fuel additive.
- The diesel fuel composition as defined in claim 9 or 11, wherein the diesel fuel contains not more than 0.1 weight % of sulfur.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP94827/96 | 1996-03-25 | ||
JP8094827A JPH09255973A (en) | 1996-03-25 | 1996-03-25 | Additive for gas oil and gas oil composition |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0798364A1 true EP0798364A1 (en) | 1997-10-01 |
Family
ID=14120893
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97302039A Withdrawn EP0798364A1 (en) | 1996-03-25 | 1997-03-25 | Diesel fuel additives and diesel fuel composition |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0798364A1 (en) |
JP (1) | JPH09255973A (en) |
CA (1) | CA2200796A1 (en) |
SG (1) | SG82571A1 (en) |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0926221A2 (en) * | 1997-12-22 | 1999-06-30 | Chevron Chemical Company LLC | Diesel fuel composition containing the salt of an alkyl hydroxyaromatic compound and aliphatic amine |
WO2001051592A1 (en) * | 2000-01-14 | 2001-07-19 | Exxonmobil Research And Engineering Company | Gasoline composition |
WO2001088064A2 (en) * | 2000-03-16 | 2001-11-22 | The Lubrizol Corporation | Anti-static lubricity additive for ultra-low sulfur diesel fuels |
EP1209217A2 (en) * | 2000-11-24 | 2002-05-29 | Clariant GmbH | Fuel oils with improved lubricating activity, containing reaction products of fatty acids with short-chained oil-soluble amines |
WO2002055636A1 (en) * | 2001-01-12 | 2002-07-18 | Exxonmobil Research And Engineering Company | Gasoline composition |
US6458173B1 (en) | 1998-12-04 | 2002-10-01 | Infineum International Ltd. | Fuel additive and fuel composition containing the same |
WO2003031543A2 (en) * | 2001-10-05 | 2003-04-17 | Unichema Chemie B.V. | Lubricant or fuel composition comprising an amide as friction-reducing additive |
US6589302B1 (en) | 2000-05-09 | 2003-07-08 | Texaco Inc. | Friction modifier for poor lubricity fuels |
US6610111B2 (en) | 2000-11-24 | 2003-08-26 | Clariant Gmbh | Fuel oils having improved lubricity comprising mixtures of fatty acids with paraffin dispersants, and a lubrication-improving additive |
EP1357170A2 (en) * | 2002-04-24 | 2003-10-29 | Ethyl Corporation | Friction modifier additives for fuel compositions and methods of use thereof |
US6743266B2 (en) | 2000-03-31 | 2004-06-01 | Texaco, Inc. | Fuel additive composition for improving delivery of friction modifier |
EP1431374A1 (en) | 2002-12-20 | 2004-06-23 | Chevron Oronite Company LLC | A method of reducing particulate emissions in internal combustion engines |
US6835217B1 (en) | 2000-09-20 | 2004-12-28 | Texaco, Inc. | Fuel composition containing friction modifier |
SG110063A1 (en) * | 2003-03-26 | 2005-04-28 | Ethyl Corp | Additives for fuel compositions to reduce formation of combustion chamber deposits |
DE102007022496A1 (en) | 2006-12-19 | 2008-07-03 | Afton Chemical Intangibles, Llc | A method of improving low temperature compatibility of amide friction modifiers in fuels and amide friction modifiers |
US7435272B2 (en) | 2002-04-24 | 2008-10-14 | Afton Chemical Intangibles | Friction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof |
US7566687B2 (en) | 2005-06-13 | 2009-07-28 | Jacam Chemical, LLC | Methods and compositions for removing sulfur from liquid hydrocarbons |
CN102229837A (en) * | 2011-05-19 | 2011-11-02 | 赵志明 | Antiwear agent for petroleum diesel oil and application method thereof |
WO2012076896A1 (en) * | 2010-12-09 | 2012-06-14 | Innospec Limited | Improvements in or relating to additives for fuels and lubricants |
US8287608B2 (en) | 2005-06-27 | 2012-10-16 | Afton Chemical Corporation | Lubricity additive for fuels |
US11142715B2 (en) | 2018-11-07 | 2021-10-12 | Chevron U.S.A. Inc. | Amino alkanediols and carboxylate salts as additives for improving fuel efficiency |
WO2023274335A1 (en) | 2021-06-30 | 2023-01-05 | 中国石油化工股份有限公司 | Lubricity improver composition for fuel oil and use thereof |
Families Citing this family (4)
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GB9810994D0 (en) * | 1998-05-22 | 1998-07-22 | Exxon Chemical Patents Inc | Additives and oil compositions |
US6051039A (en) * | 1998-09-14 | 2000-04-18 | The Lubrizol Corporation | Diesel fuel compositions |
FR2888248B1 (en) * | 2005-07-05 | 2010-02-12 | Total France | LUBRICATING COMPOSITION FOR HYDROCARBON MIXTURE AND PRODUCTS OBTAINED |
JP5301116B2 (en) * | 2007-06-07 | 2013-09-25 | 有限会社タービュランス・リミテッド | Fuel additive and fuel composition for diesel engine having multi-stage injection mechanism |
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Cited By (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0926221A3 (en) * | 1997-12-22 | 2000-02-23 | Chevron Chemical Company LLC | Diesel fuel composition containing the salt of an alkyl hydroxyaromatic compound and aliphatic amine |
EP0926221A2 (en) * | 1997-12-22 | 1999-06-30 | Chevron Chemical Company LLC | Diesel fuel composition containing the salt of an alkyl hydroxyaromatic compound and aliphatic amine |
US6458173B1 (en) | 1998-12-04 | 2002-10-01 | Infineum International Ltd. | Fuel additive and fuel composition containing the same |
WO2001051592A1 (en) * | 2000-01-14 | 2001-07-19 | Exxonmobil Research And Engineering Company | Gasoline composition |
WO2001088064A2 (en) * | 2000-03-16 | 2001-11-22 | The Lubrizol Corporation | Anti-static lubricity additive for ultra-low sulfur diesel fuels |
US6793695B2 (en) | 2000-03-16 | 2004-09-21 | The Lubrizol Corporation | Anti-static lubricity additive ultra-low sulfur diesel fuels |
WO2001088064A3 (en) * | 2000-03-16 | 2003-04-17 | Lubrizol Corp | Anti-static lubricity additive for ultra-low sulfur diesel fuels |
US6743266B2 (en) | 2000-03-31 | 2004-06-01 | Texaco, Inc. | Fuel additive composition for improving delivery of friction modifier |
US6589302B1 (en) | 2000-05-09 | 2003-07-08 | Texaco Inc. | Friction modifier for poor lubricity fuels |
US6835217B1 (en) | 2000-09-20 | 2004-12-28 | Texaco, Inc. | Fuel composition containing friction modifier |
EP1209217A2 (en) * | 2000-11-24 | 2002-05-29 | Clariant GmbH | Fuel oils with improved lubricating activity, containing reaction products of fatty acids with short-chained oil-soluble amines |
EP1209217A3 (en) * | 2000-11-24 | 2003-07-09 | Clariant GmbH | Fuel oils with improved lubricating activity, containing reaction products of fatty acids with short-chained oil-soluble amines |
US6610111B2 (en) | 2000-11-24 | 2003-08-26 | Clariant Gmbh | Fuel oils having improved lubricity comprising mixtures of fatty acids with paraffin dispersants, and a lubrication-improving additive |
USRE40758E1 (en) * | 2000-11-24 | 2009-06-23 | Clariant Produkte (Deutschland) Gmbh | Fuel oils having improved lubricity comprising mixtures of fatty acids with paraffin dispersants, and a lubrication-improving additive |
DE10058356B4 (en) * | 2000-11-24 | 2005-12-15 | Clariant Gmbh | Fuel oils with improved lubricity, containing reaction products of fatty acids with short-chain oil-soluble amines |
DE10058356A1 (en) * | 2000-11-24 | 2002-06-06 | Clariant Gmbh | Fuel oils with improved lubricating properties, containing reaction products from fatty acids with short-chain oil-soluble amines |
US6793696B2 (en) | 2000-11-24 | 2004-09-21 | Clariant Gmbh | Enhanced lubricity fuel oil compositions comprising salts of fatty acids with short chain oil-soluble amines |
WO2002055636A1 (en) * | 2001-01-12 | 2002-07-18 | Exxonmobil Research And Engineering Company | Gasoline composition |
WO2003031543A2 (en) * | 2001-10-05 | 2003-04-17 | Unichema Chemie B.V. | Lubricant or fuel composition comprising an amide as friction-reducing additive |
WO2003031543A3 (en) * | 2001-10-05 | 2003-08-28 | Unichema Chemie Bv | Lubricant or fuel composition comprising an amide as friction-reducing additive |
US7435272B2 (en) | 2002-04-24 | 2008-10-14 | Afton Chemical Intangibles | Friction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof |
US6866690B2 (en) | 2002-04-24 | 2005-03-15 | Ethyl Corporation | Friction modifier additives for fuel compositions and methods of use thereof |
US7846224B2 (en) | 2002-04-24 | 2010-12-07 | Afton Chemical Intangibles, Llc | Methods to improve the low temperature compatibility of amide friction modifiers in fuels and amide friction modifiers |
EP1357170A3 (en) * | 2002-04-24 | 2004-09-08 | Ethyl Corporation | Friction modifier additives for fuel compositions and methods of use thereof |
EP1357170A2 (en) * | 2002-04-24 | 2003-10-29 | Ethyl Corporation | Friction modifier additives for fuel compositions and methods of use thereof |
US7402185B2 (en) | 2002-04-24 | 2008-07-22 | Afton Chemical Intangibles, Llc | Additives for fuel compositions to reduce formation of combustion chamber deposits |
EP1431374A1 (en) | 2002-12-20 | 2004-06-23 | Chevron Oronite Company LLC | A method of reducing particulate emissions in internal combustion engines |
KR100533490B1 (en) * | 2003-03-26 | 2005-12-06 | 에틸코오포레이션 | Additives for fuel compositions to reduce formation of combustion chamber deposits |
SG110063A1 (en) * | 2003-03-26 | 2005-04-28 | Ethyl Corp | Additives for fuel compositions to reduce formation of combustion chamber deposits |
US7566687B2 (en) | 2005-06-13 | 2009-07-28 | Jacam Chemical, LLC | Methods and compositions for removing sulfur from liquid hydrocarbons |
US8287608B2 (en) | 2005-06-27 | 2012-10-16 | Afton Chemical Corporation | Lubricity additive for fuels |
DE102007022496A1 (en) | 2006-12-19 | 2008-07-03 | Afton Chemical Intangibles, Llc | A method of improving low temperature compatibility of amide friction modifiers in fuels and amide friction modifiers |
WO2012076896A1 (en) * | 2010-12-09 | 2012-06-14 | Innospec Limited | Improvements in or relating to additives for fuels and lubricants |
CN102229837A (en) * | 2011-05-19 | 2011-11-02 | 赵志明 | Antiwear agent for petroleum diesel oil and application method thereof |
US11142715B2 (en) | 2018-11-07 | 2021-10-12 | Chevron U.S.A. Inc. | Amino alkanediols and carboxylate salts as additives for improving fuel efficiency |
WO2023274335A1 (en) | 2021-06-30 | 2023-01-05 | 中国石油化工股份有限公司 | Lubricity improver composition for fuel oil and use thereof |
Also Published As
Publication number | Publication date |
---|---|
CA2200796A1 (en) | 1997-09-25 |
SG82571A1 (en) | 2001-08-21 |
JPH09255973A (en) | 1997-09-30 |
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