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
  • C10L1/224—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
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal
• • 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
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
  • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
• • 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
  • C10L1/1985—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 polyethers, e.g. di- polygylcols and derivatives; ethers - esters
• • 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
  • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
  • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
• • 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 gas oil additive and a gas oil composition which can be effective in reducing wear of metal surfaces contacting the composition in a system using a low-sulfur gas oil, and effective in deterging a fuel injection nozzle.
• stains of the fuel injection nozzle for the diesel engines mainly cokes, cause significant mal-affects to its performance.
• the cokes When the cokes are formed, the contents of black smoke in the exhaust gas, sulfates derived from sulfur in the fuel, and hydrocarbons formed by partial combustion of fuels and lubricating oils (those hydrocarbons are collectively referred to "particulate matters") are increased.
• Japanese Patent Examined Publication No. 63-32837 discloses a nitrogen-containing polyoxyethylene compound as a gas oil additive for decreasing particulate matters in the exhaust gas for diesel engines.
• this publication is completely silent on the low-sulfur gas oil having a sulfur content of 0.2% by weight or less in the gas oil. It rather mentions the application to a gas oil according to JIS K 2204 (level required at the time of 1988).
• JIS K 2204 level required at the time of 1988.
• JIS K 2204 level required at the time of 1988.
• the JIS standard of the sulfur content in the gas oil of those days is 0. 5% by weight or less, and the average sulfur content of the commercially available gas oil of those days is 0.4% by weight on average (see Nisseki Review , 30 , 6).
• W0941760 discloses the use of an ester obtained from a carboxylic acid having 2 to 50 carbon atoms and an alcohol as an agent for reducing wear in low-sulfur diesel gas oils.
• its performance in wear resistance cannot be said to be satisfactory.
• fuel additives there has been disclosed a composition comprising cyclopentyl ester of formic acid, a condensate obtained from triethanolamine and oleic acid, and a spindle oil as an additive for diesel fuels for the purpose of improving exhaust gas (Japanese Patent Laid-Open No. 50-161504).
• Japanese Patent Laid-Open No. 50-161504 Japanese Patent Laid-Open No.
• this publication is completely silent with regard to wear caused by the low-sulfur gas oil.
• the sulfur content in the gas oil subjected to use is high, the necessity for countermeasure for preventing wear caused by the decreased sulfur content is presumably not particularly considered.
• Japanese Patent Laid-Open Nos. 55-082191 and 55-00780 and W09307238 each discloses the use of an alkanolamide as an emulsifier for emulsion fuels.
• U.S. Patent No. 4204481 discloses the use of an oleic acid amide of diethanolamine as a wear inhibitor for alcohol fuels.
• these publications are silent with regard to the use in the low-sulfur gas oil.
• an object of the present invention is to provide a gas oil additive and a gas oil composition which are effective in reducing a wear amount of metal surfaces contacting the composition in a system using a low-sulfur gas oil; effective in deterging a fuel injection nozzle for the diesel engines; and effective in the improvement in the storage stability of the low-sulfur gas oil.
• the present inventors have found that the gas oil composition for diesel engines having an excellent effect of reducing wear amounts, an excellent detergency effect of a fuel injection nozzle, and an excellent effect for storage stability can be obtained by including a particular compound as a gas oil additive in a gas oil having a sulfur content of 0.2% by weight or less.
• the present invention has been completed based on these findings.
• the gist of the present invention pertains to the following:
• the gas oil additive of the present invention comprises Compound A described below, or it may further comprise Compound B in addition to Compound A.
• Compound A is a compound containing a hydrocarbon group having 10 to 22 carbon atoms, amide group, and hydroxyl group on a carbon atom in ⁇ -position to nitrogen atom of the amide group in a molecule.
• the compounds include condensates obtained from one or more fatty acids and one or more compounds selected from monoethanolamine, diethanolamine, mono-2-propanolamine, and di-2-propanolamine.
• fatty acid refers to a linear or branched, monovalent fatty acid having 10 to 22 carbon atoms, which may be a saturated fatty acid or an unsaturated fatty acid, respectively.
• the fatty acids include monovalent fatty acids containing a linear or branched, saturated alkyl group having 10 to 22 carbon atoms, including decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachic acid, behenic acid, or the like; and unsaturated fatty acids having 10 to 22 carbon atoms, including oleic acid, erucic acid, linoelaidic acid, linoleic acid, or the like.
• fatty acid esters corresponding to the fatty acids mentioned above may be used instead of, or together with, these fatty acids.
• the fatty acid esters include esters obtained from the fatty acids mentioned above and alcohols having 1 to 3 carbon atoms.
• a linear, saturated fatty acid having 12 to 14 carbon atoms more preferably lauric acid having 12 carbon atoms; or a linear, unsaturated fatty acid having 16 to 20 carbon atoms, more preferably 9-octadecenoic acid having 18 carbon atoms.
• an embodiment wherein two or more fatty acids are used may be included in the present invention.
• a mixture of fatty acids wherein to a total amount of the fatty acids, the weight proportion of a fatty acid having one unsaturated bond is 70 to 90% by weight; the weight proportion of a fatty acid having two unsaturated bonds is 5 to 10% by weight; and the weight proportion of a saturated fatty acid is 5 to 20% by weight.
• the number of carbon atoms for these fatty acids it is more preferred that the number of carbon atoms of the fatty acid having one unsaturated bond is 14, 16 or 18; the number of carbon atoms of the fatty acid having two unsaturated bonds is 18; and the number of carbon atoms of the saturated fatty acid is 14, 16 or 18. From the viewpoint of preventing wear even more effectively, the saturated fatty acid is preferably used, and from the viewpoint of high solubility to the gas oil, the unsaturated fatty acid is preferably used.
• the gas oil additives having excellent performance satisfying all of the solubility to gas oil, the wear resistance effect and the detergency effect can be obtained by using the mixture of the fatty acids mentioned above of the saturated fatty acid and the unsaturated fatty acid.
• the additives containing 68 to 78% by weight of 9-octadecenoic acid to a total amount of the fatty acids, including fatty acid esters described below, are particularly preferably used.
• the additives containing 68 to 78% by weight of 9-octadecenoic acid ester to the total amount of the fatty acids or the fatty acid esters are preferably used.
• the amine compounds which are used for condensation include one or more compounds selected from monoethanolamine, diethanolamine, mono-2-propanolamine, and di-2-propanolamine.
• condensates obtained from fatty acids and one or more compounds selected from monoethanolamine, diethanolamine, mono-2-propanolamine, and di-2-propanolamine include the following:
• examples thereof include fatty acid amides of monoethanolamine, fatty acid esters of monoethanolamine, fatty acid amide-esters of monoethanolamine, and the like.
• the fatty acid amides of monoethanolamine are used as a component.
• the condensates are obtained from a fatty acid and diethanolamine
• examples thereof include fatty acid amides of diethanolamine, fatty acid esters of diethanolamine, fatty acid amide-esters of diethanolamine, and the like.
• the fatty acid amides of diethanolamine are used as a component.
• the condensate obtained from a fatty acid and monoethanolamine and diethanolamine is a mixture of the condensates mentioned above.
• the condensates are obtained from a fatty acid and mono-2-propanolamine
• examples thereof include fatty acid amides of mono-2-propanolamine, fatty acid esters of mono-2-propanolamine, fatty acid amide-esters of mono-2-propanolamine, and the like.
• the fatty acid amides of mono-2-propanolamine are used as a component.
• examples thereof include fatty acid amides of di-2-propanolamine, fatty acid esters of di-2-propanolamine, fatty acid amide-esters of di-2-propanolamine, and the like.
• the fatty acid amides of di-2-propanolamine are used as a component.
• Compound A used in the gas oil additives of the present invention can be prepared, for example, by following method.
• a desired condensate can be obtained by a process comprising heating a fatty acid together with one or more compounds selected from monoethanolamine, diethanolamine, mono-2-propanolamine, and di-2-propanolamine, and carrying out amidation reaction while removing water formed.
• a desired condensate can be obtained in a higher yield by a process comprising reacting a fatty acid ester such as a methyl ester of a fatty acid together with one or more compounds selected from monoethanolamine, diethanolamine, mono-2-propanolamine, and di-2-propanolamine with heating while removing methanol.
• the total content of one or more compounds selected from monoethanolamine, diethanolamine, mono-2-propanolamine, and di-2-propanolamine which are unreacted and remain in the reaction product exceeds 5% by weight, the effect for reducing wear and the detergency effect of a fuel injection nozzle are drastically declined. Therefore, it is desired that the total remaining amount of one or more compounds selected from monoethanolamine, diethanolamine, mono-2-propanolamine, and di-2-propanolamine is controlled to 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, most preferably 0.5% by weight or less.
• fatty acid esters are esters obtained from a fatty acid and a lower alcohol, such as methanol, ethanol and propanol.
• Compounds B are one or more compounds selected from the group consisting of nonionic surfactants having an HLB of 3 to 13; aliphatic amines having 8 to 28 carbon atoms; and alkylene oxide adducts of an aliphatic amine having 8 to 28 carbon atoms, of which the alkylene oxide moiety has 2 to 3 carbon atoms with molar addition of 50 mol or less.
• nonionic surfactants having an HLB of 3 to 13 include polyoxyalkylene alkyl ethers, polyoxyalkylene alkenyl ethers, polyoxyalkylene alkylphenyl ethers, sorbitan fatty acid esters, polyoxyalkylene sorbitan fatty acid esters, polyoxyalkylene sorbitol fatty acid esters, polyoxyalkylene fatty acid esters, glycerol fatty acid esters, and the like.
• the polyoxyalkylene alkyl ethers and the polyoxyalkylene alkenyl ethers are alkylene oxide adducts of which the alkylene oxide moiety has 2 to 3 carbon atoms, the adducts having a linear or branched, alkyl group or alkenyl group having 8 to 30 carbon atoms, more preferably 10 to 22 carbon atoms, and still more preferably alkylene oxide adducts having a linear alkyl group or alkenyl group having 10 to 22 carbon atoms.
• polyoxyalkylene alkyl ethers and the polyoxyalkylene alkenyl ethers include polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, and the like, and each of those listed above may have an oxypropylene group in a molecule.
• the HLB is preferably 5 to 13, more preferably 7 to 12.
• the polyoxyalkylene alkylphenyl ethers are alkylene oxide adducts of which alkylene oxide moiety has 2 to 3 carbon atoms, the adducts having an alkylphenyl group having 8 to 30 carbon atoms. More concrete examples thereof include polyoxyalkylene octylphenyl ether, polyoxyalkylene nonylphenyl ether, and the like.
• the HLB is preferably 5 to 13, more preferably 7 to 12.
• the sorbitan fatty acid esters and the polyoxyalkylene sorbitan fatty acid esters are sorbitan fatty acid esters and fatty acid esters of sorbitan alkylene oxide adducts of which the alkylene oxide moiety has 2 to 3 atoms, each of the fatty acid esters having 10 to 28 carbon atoms. It is desired that the fatty acid ester has 10 to 22 carbon atoms, and it is more desired that a linear, saturated fatty acid ester has 12 to 18 carbon atoms, or a linear, unsaturated fatty acid ester has 14 to 20 carbon atoms.
• the polyoxyalkylene sorbitol fatty acid esters are fatty acid esters of sorbitol alkylene oxide adducts of which the alkylene oxide moiety has 2 to 3 carbon atoms, each of the fatty acid esters having 10 to 28 carbon atoms. It is desired that a linear, saturated or unsaturated fatty acid ester has 10 to 20 carbon atoms, and it is more desired that a linear, saturated fatty acid ester has 12 to 18 carbon atoms, or a linear, unsaturated fatty acid ester has 14 to 20 carbon atoms.
• the polyoxyalkylene fatty acid esters are alkylene oxide adducts of which alkylene oxide moiety has 2 to 3 carbon atoms, and the fatty acid moiety has 10 to 28 carbon atoms. It is desired that a linear, saturated or unsaturated fatty acid ester has 12 to 20 carbon atoms, and it is more desired that a linear, saturated fatty acid ester has 12 to 18 carbon atoms or a linear, unsaturated fatty acid ester has 14 to 20 carbon atoms.
• the glycerol fatty acid esters are mono-, di-, triesters obtained from glycerol and fatty acids having 10 to 28 carbon atoms, preferably esters obtained from a linear, saturated or unsaturated fatty acid having 12 to 20 carbon atoms and glycerol, more preferably mono- and diesters thereof.
• Preferred examples of the fatty acids used in esterification with glycerol include lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and the like.
• a linear, unsaturated fatty acid having 14 to 20 carbon atoms is more preferably used.
• the aliphatic amines having 8 to 28 carbon atoms are aliphatic amines having an aliphatic, saturated hydrocarbon group or aliphatic, unsaturated hydrocarbon group having 8 to 28 carbon atoms.
• Concrete examples of the aliphatic amines include decylamine, laurylamine, myristylamine, cetylamine, stearylamine, oleylamine, beef tallow amine, hydrogenated beef tallow amine, and the like.
• a saturated or unsaturated, aliphatic amine having 12 to 20 carbon atoms is preferably used, and an unsaturated, aliphatic amine having 14 to 20 carbon atoms is more preferably used.
• alkylene oxide adducts of the aliphatic amines mentioned above of which the alkylene oxide moiety has 2 to 3 carbon atoms with molar addition of 50 mol or less, preferably the alkylene oxide adducts with molar addition of 20 mol or less, more preferably the alkylene oxide adducts with molar addition of 10 mol or less.
• alkylene oxide adducts in Compound B used in the present invention include ethylene oxide adducts and propylene oxide adducts.
• the alkylene oxide may be used alone or in combination.
• the monomeric units may be polymerized by block addition or random addition.
• Compound A is preferably used in combination with Compound B.
• the blending amount of Compound B is suitably determined according to the properties of the gas oil used, and the weight ratio of Compound A/Compound B is preferably from 1/0.01 to 1/0.5, more preferably from 1/0.02 to 1/0.3, particularly preferably from 1/0.03 to 1/0.2.
• the amount of the gas oil additive of the present invention is not particularly limited, and the gas oil additive can be used in an amount sufficient to suppress at least the wear of the contacting surfaces of a metal by the gas oil.
• the gas oil additive in an amount of from 0.001 to 0.1 parts by weight, preferably from 0.001 to 0.05 parts by weight, based on 100 parts by weight of the gas oil.
• the amount is less than 0.001 parts by weight, the effect for reducing wear is lessened.
• the amount exceeds 0.1 parts by weight the effect for reducing wear is not increased, thereby making it economically disadvantageous.
• the gas oil additive in an amount of from 0.001 to 0.1 parts by weight, preferably from 0.005 to 0.05 parts by weight, based on 100 parts by weight of the gas oil, from the viewpoints of the above effects and economic advantages.
• the gas oil additive in order to remove the stains, it is desired to use the gas oil additive in an amount of from 0.001 to 1.0 part by weight, desirably from 0.05 to 1.0 part by weight, based on 100 parts by weight of the gas oil.
• gas oil used in the present invention refers to a low-sulfur gas oil having a sulfur content of 0.2% by weight or less, particularly 0.05% by weight or less, is desirably used.
• the low-sulfur gas oil which can be used in the present invention include those prepared by a method comprising, using a hydrodesulfurization apparatus, subjecting a gas oil distillate resulting from distillation of a crude oil under atmospheric pressure to, for instance, (1) hydrodesulfurization at a high reaction temperature; (2) hydrodesulfurization under a high hydrogen partial pressure; (3) hydrodesulfurization using a hydrodesulfurization catalyst having high activity, or the like.
• the methods for desulfurization are not particularly limited.
• additives can be suitably used.
• additives include antioxidants, conductivity improvers, metal deactivators, freezing-controlling additives, cetane number improvers, combustion improvers (including smoke controllers), surfactants/dispersants, manifold system detergents, corrosion inhibitors, demulsifiers, top cylinder lubricants, and dyes.
• phenolic antioxidants are suitably used, and other gas oil-soluble antioxidants other than phenolic antioxidants can also be used.
• suitable antioxidants other than phenolic antioxidants include amine antioxidants and other similar substances.
• the amount of the antioxidant is preferably in range of from about 2.8 g to about 28 g per 1000 liters of the gas oil composition. However, the antioxidant can be used exceeding the upper limit of this range as occasion demands.
• the conductivity improver is an additive to be dissolved in the gas oil composition in order to elevate the conductivity of the resulting gas oil composition to an appropriate range, for example, from about 50 ps/m to about 600 ps/m, as measured according to ASTEM D-2624.
• the amount thereof is preferably in a range of from about 5 g to about 50 g per 1000 liters of the gas oil composition.
• the function mechanism of the compound of the present invention is considered to be as follows.
• the compound of the present invention adsorbs to the metal surfaces via OH group in the compound in the present invention, and the adsorbed compound forms a lubricative film, which presumably provides the effect for reducing wear. Therefore, the compound having OH group in a molecule is effective in adsorbing to the metal.
• the compound having a structure such that the OH group is located on the carbon atom at a ⁇ -position to the nitrogen atom, and having an ability of forming a chelate to the metal is effective in adsorbing to the metal surfaces.
• the compounds having two OH groups are preferably used.
• the OH group and the nitrogen atom collaborate to bind with the stains to form a chelate compound, whereby the stains are made soluble and dispersible, so that the detergency effect of a fuel injection nozzle of diesel engines is presumably exhibited.
• the hydrocarbon group of the fatty acid plays a large role in dissolving and dispersing the compound of the present invention in the gas oil.
• turbidity in the low-sulfur gas oil under exposure is formed by the fact that the components in the gas oil are subject to deterioration by light and oxygen to form polar substances and grow, which subsequently are precipitated in the gas oil as an insoluble component in the gas oil.
• Compound B mentioned above stabilizes this polar substance in dispersion and prevents the insoluble components from depositing.
• the gas oil additive of the present invention is used in the gas oil wherein the sulfur content in the gas oil is 0.2% by weight or less, particularly 0.05% by weight or less, the remarkable effect for reducing wear in a fuel injection pump and the remarkable detergency effect of a fuel injection nozzle can be obtained. Also, the gas oil with improved storage stability can be obtained.
• a two-liter four-necked flask was charged with 2.5 mol of methyl 9-octadecenoate, 2.5 mol of diethanolamine and 0.03 mol of sodium methoxide as a catalyst, and the temperature of the contents was raised while stirring the resulting mixture in a nitrogen gas atmosphere. Subsequently, the components were reacted while removing methanol under a reduced pressure of 30 mmHg at 110°C. Having confirmed that no more methanol is distilled off, the reaction was terminated, and the catalyst was adsorbed by an alkali adsorbent and removed from the reaction mixture, to give a reaction product.
• the resulting reaction product was analyzed by GPC analysis (gel permeation chromatogram), to give 85% of N,N-bis-(2-hydroxyethyl)oleamide.
• GPC analysis gel permeation chromatogram
• an amide-ester compound was obtained as a by-product.
• the amount of diethanolamine remaining in the resulting mixture was 0.2% by weight.
• Example 5 The similar procedures as in Example 5 were carried out except that methanol was not sufficiently removed, to prepare a reaction product in which diethanolamine remained in the reaction product in an amount of 1.5% by weight or more.
• Monoglyceride content 90% by weight or more (according to catalogue).
• Each of Compounds 1 to 10 usable in the present invention was added in an amount shown in Table 1, to 100 parts by weight of a low-sulfur gas oil having a sulfur content of 0.04% by weight or 0.20% by weight, to prepare a composition.
• the resulting composition was subjected to a standard test known as a ball-lubricity evaluation test using a cylinder.
• the test procedures are in accordance with ASTM D 5001-90.
• the scar diameter was measured.
• the smaller the scar diameter the more effective the additives become regarding wear prevention.
• the gas oil composition was stored at 25°C for one month under a surrounding light condition prior to carrying out the lubricity test.
• the test temperature was 25°C at start, and raised to 45° to 50°C by frictional heat during test.
• the wear amount of each of the gas oil compositions containing Compounds usable in the present invention, namely the gas oil composition of the present invention, is 13.8 mg to 27.5 mg, showing excellent wear resistance.
• the performance in preventing wear was slightly reduced as compared with Compounds of Preparation Examples 17 and 18 derived from methyl esters of fatty acids.
• the detergency performance of the cokes at the injector nozzle portion of diesel engines for each of Compounds 1 to 11 was evaluated by the following method. Specifically, a fuel oil prepared by adding 0.5% by weight of each of Compounds 1 to 11 and Comparative Product 1 to a commercially available gas oil (sulfur content: 0.2% by weight) was loaded on an automobile to carry out test runs with automobiles on city streets.
• HLB 10 ⁇ inorganic character/organic character.
• the pin held between the V-blocks was rotated for ten minutes without applying a load, and subsequently, the pin held between the V-blocks was preliminarily rotated for five minutes while applying a load of 100 lbs., and the machine was operated for three hours while applying a load of 150 lbs.
• the wear amounts of the V-blocks and the pins after operation were measured. The results are shown in Table 6. Incidentally, the test temperature was 25°C at start, and raised to 45° to 50°C by frictional heat during test.
• Each of the gas oil composition shown in Table 8 as Examples and Comparative Examples having a sulfur content of 0.04% by weight in which Compound A was added either alone or added in combination with Compound B was allowed to stand under exposure at 60°C to determine the number of days required for precipitating insoluble components in the gas oil compositions.
• the number of days required for precipitating insoluble components was about the same as the gas oil containing no additives or the gas oil compositions used in combination with Comparative Example 3 or 4.
• the number of days required for precipitating insoluble components was extended, so that excellent storage stability could be obtained.
• the gas oil composition of the present invention By using the gas oil composition of the present invention, there can be exhibited effects in reducing wear of fuel pumps in a system using a gas oil likely to cause wear in fuel pumps, the gas oil having a sulfur content of 0.2% by weight or less, particularly 0.05% by weight or less, and detergency effects of an injection nozzle of diesel engines. Further, an excellent storage ability of the gas oil can be obtained.
• the effects of the present invention are to satisfy the both the function of preventing wear of the fuel injection pumps during the use of low-sulfur gas oils and the function of detergency effects of stains on the fuel injection nozzle along with the use of the diesel engines, which could not be found in the prior arts.

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• 1996
  • 1996-11-11 EP EP96937558A patent/EP0957152A4/de not_active Withdrawn
  • 1996-11-11 WO PCT/JP1996/003312 patent/WO1997027271A1/ja not_active Application Discontinuation

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