EP0680506A1 - Composition de fuel-oil. - Google Patents
Composition de fuel-oil.Info
- Publication number
- EP0680506A1 EP0680506A1 EP94905667A EP94905667A EP0680506A1 EP 0680506 A1 EP0680506 A1 EP 0680506A1 EP 94905667 A EP94905667 A EP 94905667A EP 94905667 A EP94905667 A EP 94905667A EP 0680506 A1 EP0680506 A1 EP 0680506A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- acid
- alcohol
- fuel
- carbon atoms
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 239000000446 fuel Substances 0.000 title claims abstract description 45
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 239000000654 additive Substances 0.000 claims abstract description 38
- 230000000996 additive effect Effects 0.000 claims abstract description 27
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000005864 Sulphur Substances 0.000 claims abstract description 16
- 239000000295 fuel oil Substances 0.000 claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- -1 polymethylene group Polymers 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000010771 distillate fuel oil Substances 0.000 claims description 3
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 description 9
- 239000002283 diesel fuel Substances 0.000 description 8
- 231100000241 scar Toxicity 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- AFSHUZFNMVJNKX-UHFFFAOYSA-N 1,2-di-(9Z-octadecenoyl)glycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCC=CCCCCCCCC AFSHUZFNMVJNKX-UHFFFAOYSA-N 0.000 description 1
- AFSHUZFNMVJNKX-LLWMBOQKSA-N 1,2-dioleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC\C=C/CCCCCCCC AFSHUZFNMVJNKX-LLWMBOQKSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000001698 Lecitin citrate Substances 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YKGYQYOQRGPFTO-UHFFFAOYSA-N bis(8-methylnonyl) hexanedioate Chemical compound CC(C)CCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC(C)C YKGYQYOQRGPFTO-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000006280 diesel fuel additive Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 239000010763 heavy fuel oil Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
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
- C10L1/18—Organic compounds containing oxygen
-
- 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
-
- 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
- C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
-
- 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
Definitions
- This invention relates to fuel compositions useful, for example, to improve lubricity and reduce wear in diesel engines.
- esters as additives for diesel engine fuel.
- US-A-2,527,889 describes polyhydroxy alcohol esters as primary anti-corrosion additives in diesel engine fuel
- GB-A-1 ,505,302 describes ester combinations including, for example, glycerol monoesters and glycerol diesters as diesel fuel additives, the combinations being described as leading to advantages including less wear of the fuel-injection equipment, piston rings and cylinder liners.
- GB-A-1 ,505,302 is, however, concerned with overcoming the operational disadvantages of corrosion and wear by acidic combustion products, residues in the combustion chamber and in the exhaust system.
- the document states that these disadvantages are due to incomplete combustion under certain operating conditions.
- Typical diesel fuels available at the date of the document contained, for example, from 0.5 to 1 % by weight of sulphur, as elemental sulphur, based on the weight of the fuel.
- the sulphur content of diesel fuels has now been or will be lowered in a number of countries for environmental reasons, i.e. to reduce sulphur dioxide emissions.
- heating oil and diesel fuel sulphur content are being harmonised by the CEC at a maximum of 0.2% by weight, and, at a second stage, the maximum content in diesel fuel will be 0.05% by weight. Complete conversion to the 0.05% maximum may be required during 1996.
- the process for preparing low sulphur content fuels in addition to reducing sulphur content, also reduces the content of other components of the fuel such as poiyaromatic components and polar components. Reducing one or more of the sulphur, poiyaromatic and polar component content of the fuel creates a new problem in use of the fuel, i.e. the ability of the fuel to lubricate the injection system of the engine is reduced such that, for example, the fuel injection pump of the engine can fail relatively early in the life of an engine, failure being, eg. in high pressure fuel injection systems such as high pressure rotary distributors, in-line pumps and unit injectors and injectors. Such severe failures are due to wear that is completely different from the corrosive wear problem described in GB-A-1 ,505,302.
- a first aspect of the invention is a fuel oil composition
- a fuel oil composition comprising a major proportion of a liquid hydrocarbon middle distillate fuel oil having a sulphur concentration of 0.2% by weight or less, and a minor proportion of an additive comprising an ester of a carboxylic acid and an alcohol wherein the acid has from 2 to 50 carbon atoms and the alcohol has one or more carbon atoms.
- a second aspect of the invention is the use of a fuel oil composition as defined in the first aspect of the invention as the fuel in a compression-ignition (diesel) engine for controlling wear rate in the injection system of the engine in operation of the engine.
- a compression-ignition (diesel) engine for controlling wear rate in the injection system of the engine in operation of the engine.
- a third aspect of the invention is a method of operating a compression-ignition (diesel) engine comprising providing a fuel oil composition as defined in the first aspect of the invention as the fuel in the engine thereby to control wear rate in the injection system of the engine.
- a compression-ignition (diesel) engine comprising providing a fuel oil composition as defined in the first aspect of the invention as the fuel in the engine thereby to control wear rate in the injection system of the engine.
- the additive in use of the composition in a compression-ignition internal combustion engine, is capable of forming over the range of operating conditions of the engine, at least partial mono- or multi-molecular layers of the additive on surfaces of the injection system, particularly the injector pump that are in moving contact with one another, the composition being such as to give rise, when compared with a composition lacking the additive, to one or more of a reduction in wear, a reduction in friction, or an increase in electrical contact resistance in any test where two or more loaded bodies are in relative motion under non-hydrodynamic lubricating conditions.
- the additive which may be a single additive or mixture of additives, is capable of forming at least partial layers on certain surfaces of the engine.
- the layer formed is not necessarily complete on the contacting surface. Thus, it may cover only part of the area of that contacting surface, for example 10% or more, or 50% or more.
- the formation of such layers and the extent of their coverage of a contacting surface can be demonstrated by, for example, measuring electrical contact resistance or electrical capacitance.
- tests that can be used to demonstrate one or more of a reduction in wear, a reduction in friction or an increase in electrical contact resistance according to this invention are the Ball On Cylinder Lubricant Evaluator and High Frequency Reciprocating Rig tests which will be referred to hereinafter.
- the acid from which the ester is derived may be a mono or polycarboxylic acid such as aliphatic, saturated or unsaturated, straight or branched chain, mono and dicarboxylic acids being preferred.
- the acid may be generalised in the formula
- R'(COOH) x where x represents an integer and is 1 or more such as 1 to 4, and R' represents a hydrocarbyl group having from 2 to 50 carbon atoms and which is mono or polyvalent corresponding to the value of x, the -COOH groups, when more than one is present, optionally being substituent on different carbon atoms from one another.
- 'Hydrocarbyl means a group containing carbon and hydrogen which group is connected to the rest of the molecule via a carbon atom. It may be straight or branched chain which chain may be interrupted by one or more hetero atoms such as O, S, N or P, may be saturated or unsaturated, may be aliphatic or alicyclic or aromatic including heterocyclic, or may be substituted or unsubstituted.
- the hydrocarbyl group is an alkyl group or an alkenyl group having 10 (e.g. 12) to 30 carbon atoms, i.e. the acid is saturated or unsaturated.
- the alkenyl group may have one or more double bonds, such as 1 , 2 or 3.
- saturated carboxylic acids are those with 10 to 22 carbon atoms such as capric, lauric, myristic, palmitic, and behenic acids and examples of unsaturated carboxylic acids are those with 10 to 22 carbon atoms such as oleic, elaidic, palmitoleic, petroselic, riconoleic, eleostearic, linoleic, linolenic, eicosanoic, galoleic, erucic and hypogeic acids.
- the acid is polycarboxylic, having for example from 2 to 4 carboxy groups
- the hydrocarbyl group is preferably a substituted or unsubstituted polymethylene.
- the alcohol from which the ester is derived may be a mono or polyhydroxy alcohol such as a trihydroxy alcohol.
- the alcohol may be generalised in the formula
- y represents an integer and is 1 or more and R 2 represents a hydrocarbyl group having 1 or more carbon atoms such as up to 10 carbon atoms, and which is mono or polyvalent corresponding to the value of y, the -OH groups, when more than one is present, optionally being substituent on different carbon atoms from one another.
- 'Hydrocarbyl' has the same meaning as given above for the acid.
- the hydrocarbyl group is preferably an alkyl group or a substituted or unsubstituted polymethylene group.
- monohydric alcohols are lower alkyl alcohols having from 1 to 6 carbon atoms such as methyl, ethyl, propyl and butyl alcohols.
- polyhydric alcohols are aliphatic, saturated or unsaturated, straight chain or branched alcohols having 2 to 10, preferably 2 to 6, more preferably 2 to 4, hydroxy groups, and having 2 to 90, preferably 2 to 30, more preferably 2 to 12, most preferably 2 to 5, carbon atoms in the molecule.
- the polyhydric alcohol may be a glycol or diol, or a trihydric alcohol such as glycerol.
- the esters may be used alone or as mixtures of one ore more esters and may be composed only of carbon, hydrogen and oxygen.
- the ester has a molecular weight of 200 or greater, or has at least 10 carbon atoms, or has both.
- esters examples include lower alkyl esters, such as methyl esters, of the above exemplified saturated or unsaturated monocarboxylic acids. Such esters may, for example, be obtained by saponification and esterification of natural fats and oils of plant or animal origin or by their transesterification with lower aliphatic alcohols.
- esters of polyhydric alcohols that may be used are those where all of the hydroxy groups are esterified, those where not all of the hydroxy groups are esterified, and mixtures thereof.
- Specific examples are esters prepared from trihydric alcohols and one or more of the above- mentioned saturated or unsaturated carboxylic acids, such as glycerol monoesters and glycerol diesters, e.g. glycerol monooleate, glycerol dioleate and glycerol monostearate.
- Such polyhydric esters may be prepared by esterification as described in the art and/or may be commercially available.
- the ester may have one or more free hydroxy groups.
- the sulphur concentration is 0.05% by weight or less, such as 0.01% by weight or less, and may be as low as 0.005% by weight, or 0.0001 % by weight, or lower.
- the art describes methods for reducing the sulphur concentration of hydrocarbon distillate fuels, such methods including for example solvent extraction, sulphuric acid treatment, and hydrodesulphurisation.
- tricyclic aromatic is meant a fixed system where three aromatic rings are fused together.
- the fuel contains less than 1 % by weight of such a component.
- polar components are compounds such as those containing O, S or N; and esters; and alcohols.
- the above-mentioned wear problem is found to become progressively more acute as the polar component concentration of the fuel is decreased; for example, it may be particularly severe at concentrations below 250 ppm, such as below 200 ppm and specifically in fuels having polar component concentrations of 170 ppm and 130 ppm respectively.
- Such polar component concentrations may conveniently be measured by High Pressure Liquid Chromatography, sometimes referred to as HPLC.
- Middle distillate fuel oils to which this invention is applicable generally boil within the range of about 100 * C to about 500 * C, e.g. about 150 ° C to about 400 ° C.
- the fuel oil can comprise atmospheric distillate or vacuum distillate, or cracked gas oil or a blend in any proportion of straight run and thermally and/or catalytically cracked distillates.
- the most common petroleum distillates are kerosene, jet fuels, diesel fuels, heating oils and heavy fuel oils, diesel fuels being preferred in the practice of the present invention for the above-mentioned reasons.
- the heating oil may be a straight atmospheric distillate, or it may contain amounts, e.g. up to 35% by weight of vacuum gas oil or of cracked gas oils or of both.
- the concentration of the additive of the invention in the fuel oil may be up to 250,000 ppm, for example up to 10,000 ppm such as 1 to below 1000 ppm (active ingredient) by weight per weight of fuel, preferably 10 to 500 ppm, more preferably 10 to 200 ppm.
- the additive may be incorporated into bulk fuel oil by methods known in the art.
- the additive may be so incorporated in the form of a concentrate comprising an admixture of the additive and a liquid carrier medium compatible with the fuel oil, the additive being dispersed in the liquid medium.
- Such concentrates preferably contain from 3 to 75 wt%, more preferably 3 to 60 wt%, most preferably 10 to 50 wt% of the additive, preferably in solution in the oil.
- carrier liquid are organic solvents including hydrocarbon solvents, for example petroleum fractions such as naphtha, kerosene and heater oil; aromatic hydrocarbons; paraffinic hydrocarbons such as hexane and pentane; and alkoxyalkanols such as 2-butoxyethanol.
- the carrier liquid must of course be selected having regard to its compatibility with the additive and with the fuel.
- the additives of the invention may be used singly or as mixtures of more than one additive. They may also be used in combination with one or more co- additives such as known in the art, for example the following: detergents, antioxidants (to avoid fuel degradation), corrosion inhibitors, dehazers, demulsifiers, metal deactivators, antifoaming agents, cetane improvers, cosolvents, package compatibilisers, and middle distillate cold flow improvers.
- co- additives such as known in the art, for example the following: detergents, antioxidants (to avoid fuel degradation), corrosion inhibitors, dehazers, demulsifiers, metal deactivators, antifoaming agents, cetane improvers, cosolvents, package compatibilisers, and middle distillate cold flow improvers.
- the fuels used were diesel fuels having the following characteristics
- Aromatics content ⁇ 1% (wt/wt)
- Additives D and E were dissolved in certain of fuels I and II and the resulting composition tested using:
- Friction and wear devices 2nd Ed., p. 280, American Society of Lubrication Engineers, Park Ridge III. USA; and F. Tao and J. Appledorn, ASLE trans.,
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Fuel-Injection Apparatus (AREA)
- Lubricants (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB939301119A GB9301119D0 (en) | 1993-01-21 | 1993-01-21 | Fuel composition |
GB9301119 | 1993-01-21 | ||
PCT/EP1994/000148 WO1994017160A1 (fr) | 1993-01-21 | 1994-01-20 | Composition de fuel-oil |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0680506A1 true EP0680506A1 (fr) | 1995-11-08 |
EP0680506B1 EP0680506B1 (fr) | 1997-01-22 |
Family
ID=10729049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94905667A Revoked EP0680506B1 (fr) | 1993-01-21 | 1994-01-20 | Composition de fuel-oil |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP0680506B1 (fr) |
JP (1) | JP2634697B2 (fr) |
KR (1) | KR100286781B1 (fr) |
AT (1) | ATE148157T1 (fr) |
AU (1) | AU676713B2 (fr) |
BR (1) | BR9405814A (fr) |
CA (1) | CA2154344C (fr) |
DE (1) | DE69401576T2 (fr) |
DK (1) | DK0680506T3 (fr) |
ES (1) | ES2098125T3 (fr) |
FI (1) | FI120792B (fr) |
GB (1) | GB9301119D0 (fr) |
GR (1) | GR3022462T3 (fr) |
NO (1) | NO310567B1 (fr) |
RU (1) | RU2161640C2 (fr) |
WO (1) | WO1994017160A1 (fr) |
ZA (1) | ZA94447B (fr) |
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CN107151575A (zh) * | 2017-05-13 | 2017-09-12 | 南京万象新材料科技有限责任公司 | 一种复合酯型多效能柴油抗磨剂及其应用 |
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EP3887489A1 (fr) | 2018-11-26 | 2021-10-06 | Shell Internationale Research Maatschappij B.V. | Compositions de carburant |
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- 1994-01-20 ES ES94905667T patent/ES2098125T3/es not_active Expired - Lifetime
- 1994-01-20 EP EP94905667A patent/EP0680506B1/fr not_active Revoked
- 1994-01-20 AU AU59697/94A patent/AU676713B2/en not_active Expired
- 1994-01-20 CA CA002154344A patent/CA2154344C/fr not_active Expired - Lifetime
- 1994-01-20 DE DE69401576T patent/DE69401576T2/de not_active Revoked
- 1994-01-20 WO PCT/EP1994/000148 patent/WO1994017160A1/fr not_active Application Discontinuation
- 1994-01-20 AT AT94905667T patent/ATE148157T1/de not_active IP Right Cessation
- 1994-01-20 RU RU95122648/04A patent/RU2161640C2/ru active
- 1994-01-20 KR KR1019950702995A patent/KR100286781B1/ko not_active IP Right Cessation
- 1994-01-20 DK DK94905667.5T patent/DK0680506T3/da active
- 1994-01-20 JP JP6516655A patent/JP2634697B2/ja not_active Expired - Lifetime
- 1994-01-20 BR BR9405814A patent/BR9405814A/pt not_active IP Right Cessation
- 1994-01-21 ZA ZA94447A patent/ZA94447B/xx unknown
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1995
- 1995-07-17 NO NO19952830A patent/NO310567B1/no not_active IP Right Cessation
- 1995-07-20 FI FI953499A patent/FI120792B/fi not_active IP Right Cessation
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1997
- 1997-01-31 GR GR970400173T patent/GR3022462T3/el unknown
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US6461393B1 (en) | 2000-03-16 | 2002-10-08 | Clariant Gmbh | Mixtures of carboxylic acids, their derivatives and hydroxyl-containing polymers and their use for improving the lubricating effect of oils |
US6592638B2 (en) | 2000-03-16 | 2003-07-15 | Clariant Gmbh | Mixtures of carboxylic acids, their derivatives and hydroxyl-containing polymers and their use for improving the lubricating effect of oils |
US6743266B2 (en) | 2000-03-31 | 2004-06-01 | Texaco, Inc. | Fuel additive composition for improving delivery of friction modifier |
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US7815696B2 (en) | 2002-07-09 | 2010-10-19 | Clariant Produkte (Deutschland) Gmbh | Oxidation-stabilized lubricant additives for highly desulfurized fuel oils |
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Also Published As
Publication number | Publication date |
---|---|
AU5969794A (en) | 1994-08-15 |
RU2161640C2 (ru) | 2001-01-10 |
ATE148157T1 (de) | 1997-02-15 |
FI953499A (fi) | 1995-09-20 |
DK0680506T3 (da) | 1997-08-18 |
EP0680506B1 (fr) | 1997-01-22 |
GR3022462T3 (en) | 1997-04-30 |
BR9405814A (pt) | 1995-12-05 |
KR960700330A (ko) | 1996-01-19 |
NO310567B1 (no) | 2001-07-23 |
DE69401576D1 (de) | 1997-03-06 |
ZA94447B (en) | 1994-09-01 |
ES2098125T3 (es) | 1997-04-16 |
NO952830L (no) | 1995-09-08 |
CA2154344A1 (fr) | 1994-08-04 |
KR100286781B1 (ko) | 2001-05-02 |
JP2634697B2 (ja) | 1997-07-30 |
JPH08505893A (ja) | 1996-06-25 |
DE69401576T2 (de) | 1997-05-28 |
FI120792B (fi) | 2010-03-15 |
AU676713B2 (en) | 1997-03-20 |
GB9301119D0 (en) | 1993-03-10 |
FI953499A0 (fi) | 1995-07-20 |
WO1994017160A1 (fr) | 1994-08-04 |
CA2154344C (fr) | 2003-06-17 |
NO952830D0 (no) | 1995-07-17 |
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