EP1088880A1 - Composition de combustible - Google Patents
Composition de combustible Download PDFInfo
- Publication number
- EP1088880A1 EP1088880A1 EP99117853A EP99117853A EP1088880A1 EP 1088880 A1 EP1088880 A1 EP 1088880A1 EP 99117853 A EP99117853 A EP 99117853A EP 99117853 A EP99117853 A EP 99117853A EP 1088880 A1 EP1088880 A1 EP 1088880A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- linear
- use according
- branched chain
- acid
- fuel oil
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 239000000446 fuel Substances 0.000 title description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 29
- 239000002283 diesel fuel Substances 0.000 claims abstract description 23
- 239000003921 oil Substances 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000000539 dimer Substances 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 5
- 238000009833 condensation Methods 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract description 5
- 239000013638 trimer Substances 0.000 claims abstract description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 16
- 239000000194 fatty acid Substances 0.000 claims description 16
- 229930195729 fatty acid Natural products 0.000 claims description 16
- 150000004665 fatty acids Chemical class 0.000 claims description 16
- 239000000295 fuel oil Substances 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 150000005690 diesters Chemical class 0.000 claims description 5
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 6
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract description 8
- 235000019198 oils Nutrition 0.000 description 19
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 10
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000003784 tall oil Substances 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 231100000241 scar Toxicity 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- AMOKUAKXKXBFIW-WJDWOHSUSA-N 9-[(z)-non-3-enyl]-10-octylnonadecanedioic acid Chemical compound OC(=O)CCCCCCCCC(CCCCCCCC)C(CCCCCCCC(O)=O)CC\C=C/CCCCC AMOKUAKXKXBFIW-WJDWOHSUSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- HDIFHQMREAYYJW-XGXNLDPDSA-N Glyceryl Ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-XGXNLDPDSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YKGYQYOQRGPFTO-UHFFFAOYSA-N bis(8-methylnonyl) hexanedioate Chemical class CC(C)CCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC(C)C YKGYQYOQRGPFTO-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000010771 distillate fuel oil Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
- -1 hydroxy-substituted carboxylic acid Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 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
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
Definitions
- the present invention relates to a fuel oil composition comprising a diesel fuel oil and a fuel oil lubricity improver.
- the invention further relates to the use of a composition as a diesel fuel oil lubricity improver.
- ester additives are known for addition to hydrocarbon compositions for various purposes.
- US 2993773 describes esters of alkenyl succinnic acid with a large variety of different alcohols. These esters are used to inhibit or prevent deposit-forming in hydrocarbon fuels.
- GB 1065398 describes how the lubricity of aviation turbojet fuels might be improved using partial esters of a number of different polyhydric alcohols, especially an ester of a C36 dimer acid and sorbitan monooleate.
- GB 1047493 is concerned with the addition of a lubricity additive to a lubricating oil in which the lubricity additive is a partial or mono ester of a dicarboxylic acid and an oil insoluble glycol such as the monoester of the C36 linoleic dimer acid and glycol.
- Diesel fuel oils generally comprise petroleum middle distillate fuel oils which boil within the range of about 100°C to about 400°C. There has recently been a drive to reduce the sulphur content of such diesel fuels so as to reduce sulphur dioxide emissions for environmental reasons. As of October 1996, the EU imposed a maximum sulphur content for diesel fuel oil of 0.05% by weight. As a result of this, a problem has arisen in that preparation of low sulphur content fuel oils also reduces the content in the fuels of other components such as polyaromatics. The problem is that the lubricity of the fuel is reduced and this can lead to engine failure.
- WO 94/17160 In order to overcome this problem, it has been proposed in WO 94/17160 to provide diesel fuel oil compositions with a lubricity improver additive.
- Particular examples of such an additive disclosed in WO 94/17160 are glycerol monooleate esters and di-isodecyl adipate esters.
- Glycerol monooleate esters are in commercial use as diesel fuel oil additives to enhance the lubricity of the diesel fuel oils.
- EP-A-0773278 also addresses this problem, providing as a lubricity improver additive a hydroxy-substituted carboxylic acid or acid derivative such as ricinoleic acid or glycerol monoricinoleate.
- the present invention is concerned with a new problem which arises with diesel fuel oil lubricity improvers such as glycerol monooleate.
- diesel fuel oil lubricity improvers such as glycerol monooleate.
- manufacturers recommend that the product be stored above 10°C. This is necessary because, at lower temperatures, the known diesel fuel oil lubricity improvers become unstable with a tendency to cloud or even freeze. The requirement to store at above 10°C to prevent these drawbacks is inconvenient and costly for customers who have to provide specialised storage facilities.
- the present invention aims to overcome the drawbacks of the prior art.
- the present invention provides use of a composition comprising an ester of a monocarboxylic acid and a polyhydric alcohol as a diesel fuel oil lubricity improver, wherein the monocarboxylic acid comprises a C 8 -C 24 linear or branched chain, saturated or unsaturated acid or a mixture thereof, and the polyhydric alcohol comprises an alcohol of the general formula: CR 1 R 2 R 3 R 4 , or a dimer, trimer or tetramer of the alcohol which is obtainable by condensation thereof, wherein R 1 , R 2 and R 3 are each independently a C 1 -C 12 linear or branched chain alkylol and R 4 is a linear or branched chain C 1 -C 12 alkyl or a linear or branched chain C 1 -C 12 alkylol.
- the monocarboxylic acid comprises a C 8 -C 24 linear or branched chain, saturated or unsaturated acid or a mixture thereof
- the polyhydric alcohol comprises an alcohol of the general
- the present invention provides a fuel oil composition
- a fuel oil composition comprising a diesel fuel oil having a sulphur content of no more than 0.05% by weight and a fuel oil lubricity improver comprising an ester of a monocarboxylic acid and a polyhydric alcohol as a diesel fuel oil lubricity improver
- the monocarboxylic acid comprises a C 8 -C 24 linear or branched chain, saturated or unsaturated acid or a mixture thereof
- the polyhydric alcohol comprises an alcohol of the general formula: CR 1 R 2 R 3 R 4 , or a dimer, trimer or tetramer of the alcohol which is obtainable by condensation thereof wherein R 1 , R 2 and R 3 are each independently a C 1 -C 12 linear or branched chain alkylol and R 4 is a linear or branched chain C 1 -C 12 alkyl or a linear or branched chain C 1 -C 12 alkylol.
- esters of the present invention as a diesel fuel oil lubricity improver enables the product to be storable as a liquid at a temperature below 20°C, even at a temperature below -10°C.
- the esters of the present invention possess ability comparable to the products currently on the market to improve the lubricity of diesel fuel oils. Accordingly, the need to use specialist storage facilities for the lubricity improvers is obviated.
- the ester of the present invention preferably comprises a diester, which may be part of a mixture comprising a monoester and a diester, and optionally including higher esters such as a triester and a tetraester.
- R 1 , R 2 and R 3 are preferably each independently a C 1 -C 4 linear or branched chain alkylol, more preferably CH 2 OH.
- R 4 is preferably a C 1 -C 4 linear or branched chain alkyl or alkylol, such as CH 3 , CH 2 OH or CH 2 CH 3 . More preferably R 4 is an alkylol so as to increase the number of free -OH groups in the ester.
- a particularly preferred alcohol component of the ester is pentaerythritol, although other alcohols such as trimethylolpropane (TMP) and trimethylolethane (TME)may be used. It is preferred that the ester has at least two free -OH groups.
- the carboxylic acid component of the ester may be a linear or branched chain carboxylic acid which may be saturated or unsaturated and is preferably a C 12 -C 22 monocarboxylic acid.
- the carboxylic acid has an iodine value of 40 to 180, preferably an iodine value above 60, more preferably above 70, as measured in accordance with the AOCS (American Oil Chemists Society) Official Method cd-1-25. It is preferred to use an unsaturated carboxylic acid, particularly as these are readily available and are often naturally-occurring.
- Particularly useful unsaturated carboxylic acids include oleic acid, linoleic acid, linolenic acid, palmoleic acid, gadoleic acid, erucic acid and other unsaturated acids with 22 carbon atoms, and mixtures thereof.
- the unsaturated carboxylic acid component may be selected from tall oil fatty acids, soybean fatty acids, rape seed fatty acids, sunflower seed fatty acids, fish oil and fatty acids, and cold fractionated tallow and palm oil fatty acids.
- the monocarboxylic acid may be substituted, for example, by at least one hydroxyl group.
- a suitable substituted monocarboxylic acid is ricinoleic acid.
- the esters of the present invention such as the pentaerythritol esters, have a cold stability which is independent of the molar ratio of fatty acid to alcohol.
- lubricity efficiency increases with a decrease in ratio of fatty acid to alcohol in both pentaerythritol and monoglycerides; in the monoglycerides the cold stability decreases whereas in the pentaerythritol esters it does not.
- the amount of fuel oil lubricity improver used in the fuel oil is in the range 1 to 1000ppm, preferably in the range 10 to 500ppm, most preferably in the range 10 to 200ppm.
- the ester of the present invention may be used as the diesel fuel oil lubricity improver in pure form or in mixture with other components such as the conventional diesel fuel oil lubricity improvers, such as glycerol monooleate.
- the amount of ester of the present invention in such a mixture is in the range 60 to 100%wt, preferably in the range 80 to 100%wt, most preferably in the range 90 to 95%wt, especialy around 92%.
- the properties of these mixtures are also improved over known lubricity improvers.
- the fuel oil incorporated an amount of lubricity improver as set out in Table 1 below so as to compare the effectiveness of lubricity improvers according to the present invention with those of the prior art.
- a High Frequency Reciprocating Rig (HFRR) test was carried out as described in D. Wei and H. Spikes, Wear, Vol. 111, No. 2, p. 217, 1986; and R. Caprotti, C. Bovington, W. Fowler and M. Taylor SAE paper 922183; SAE fuels and lubes. Meeting Oct. 1992; San Francisco, USA.
- the present applicants are aiming for a wear scar diameter of less than 400 microns at a dosage level of 100ppm.
- Lubricity improver A is a mixture of pentaerytritolmonooleate, pentaerytritoldioleate and pentaerytritoltrioleate including 39% diester.
- the olein fraction used for the synthesis of this pentaerytritol ester and for the glycerolmonooleate was obtained by a cold fractionation of tallow fatty acids and has cloud point between 0°C and 6°C.
- Lubricity improver B is a mixture of 92% of A and 8% of the glycerolmonooleate.
- the monoglyceride and the lubricity improver A were synthesized with tall oil fatty acids.
- Tall oil fatty acids as such are also included as comparative example.
- Dosage level monoglyceride of tall oil fatty acids (comparative) Tall oil fatty acids A 0 ppm 552 552 552 50 ppm 507 n.a. 493 100 ppm 336 339 318 200 ppm n.a. n.a. 310
- esters of the present invention have good lubricity improvement properties for diesel fuel oils and superior cold storage properties as compared with the lubricity improvers of the prior art.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99117853A EP1088880A1 (fr) | 1999-09-10 | 1999-09-10 | Composition de combustible |
EP00960644A EP1216288B1 (fr) | 1999-09-10 | 2000-09-07 | Composition de carburant |
DE60002224T DE60002224T2 (de) | 1999-09-10 | 2000-09-07 | Brennstoffzusammensetzung |
AU72864/00A AU7286400A (en) | 1999-09-10 | 2000-09-07 | Fuel composition |
PCT/EP2000/008869 WO2001019941A1 (fr) | 1999-09-10 | 2000-09-07 | Composition de carburant |
KR1020027003126A KR20020051918A (ko) | 1999-09-10 | 2000-09-07 | 연료 조성물 |
JP2001523713A JP2003509569A (ja) | 1999-09-10 | 2000-09-07 | 燃料組成物 |
AT00960644T ATE237665T1 (de) | 1999-09-10 | 2000-09-07 | Brennstoffzusammensetzung |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99117853A EP1088880A1 (fr) | 1999-09-10 | 1999-09-10 | Composition de combustible |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1088880A1 true EP1088880A1 (fr) | 2001-04-04 |
Family
ID=8238962
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99117853A Withdrawn EP1088880A1 (fr) | 1999-09-10 | 1999-09-10 | Composition de combustible |
EP00960644A Expired - Lifetime EP1216288B1 (fr) | 1999-09-10 | 2000-09-07 | Composition de carburant |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00960644A Expired - Lifetime EP1216288B1 (fr) | 1999-09-10 | 2000-09-07 | Composition de carburant |
Country Status (7)
Country | Link |
---|---|
EP (2) | EP1088880A1 (fr) |
JP (1) | JP2003509569A (fr) |
KR (1) | KR20020051918A (fr) |
AT (1) | ATE237665T1 (fr) |
AU (1) | AU7286400A (fr) |
DE (1) | DE60002224T2 (fr) |
WO (1) | WO2001019941A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004026997A2 (fr) * | 2002-09-20 | 2004-04-01 | Unichema Chemie B.V. | Composition lubrifiante |
WO2005040315A1 (fr) * | 2003-10-22 | 2005-05-06 | Leuna Polymer Gmbh | Melange d'additifs utilise comme constituant d'une formulation a base d'huile minerale |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1380635B1 (fr) | 2002-07-09 | 2013-01-23 | Clariant Produkte (Deutschland) GmbH | Agent d'amélioration de l'écoulement à froid pour huiles combustibles d'origine animale ou végétale. |
ATE370214T1 (de) * | 2002-07-09 | 2007-09-15 | Clariant Produkte Deutschland | Oxidationsstabilisierte schmieradditive für hochentschwefelte brennstofföle |
EP1408101A1 (fr) | 2002-10-04 | 2004-04-14 | Infineum International Limited | Additifs et compositions d'huile combustible |
DE102005002700A1 (de) | 2005-01-19 | 2006-07-27 | Cognis Deutschland Gmbh & Co. Kg | Zusammensetzungen verwendbar als Biotreibstoff |
DE102005002711A1 (de) * | 2005-01-19 | 2006-07-27 | Cognis Deutschland Gmbh & Co. Kg | Herstellung und Verwendung von Monoglyceriden |
PT2705125T (pt) | 2011-05-06 | 2018-02-02 | Oleon | Agente melhorador de lubrificação |
JP5850569B2 (ja) * | 2011-12-28 | 2016-02-03 | 花王株式会社 | 軽油添加剤 |
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FR1405551A (fr) * | 1963-07-16 | 1965-07-09 | Exxon Research Engineering Co | Additifs anti-usure destinés à améliorer l'onctuosité d'hydrocarbures liquides |
US3672854A (en) * | 1969-12-03 | 1972-06-27 | Universal Oil Prod Co | Middle distillate |
US5378249A (en) * | 1993-06-28 | 1995-01-03 | Pennzoil Products Company | Biodegradable lubricant |
WO1997004044A1 (fr) * | 1995-07-14 | 1997-02-06 | Exxon Chemical Patents Inc. | Additifs et compositions de carburant les contenant |
EP0773278A1 (fr) * | 1995-11-13 | 1997-05-14 | Ethyl Petroleum Additives Limited | Additif pour combustible |
DE19614722A1 (de) * | 1996-04-15 | 1997-10-16 | Henkel Kgaa | Kältestabiles Schmier- und Kraftstoffadditiv |
EP0826765A1 (fr) * | 1996-08-27 | 1998-03-04 | Institut Francais Du Petrole | Compositions d'additifs améliorant le pouvoir lubrifiant des carburants et carburants les contenant |
WO1998011178A1 (fr) * | 1996-09-13 | 1998-03-19 | Exxon Research And Engineering Company | Additif pour mazouts legers a base de polyolester |
WO1998021293A1 (fr) * | 1996-11-13 | 1998-05-22 | Henkel Corporation | Lubrifiants pour carburant diesel |
FR2772783A1 (fr) * | 1997-12-24 | 1999-06-25 | Elf Antar France | Additif d'onctuosite pour carburant |
-
1999
- 1999-09-10 EP EP99117853A patent/EP1088880A1/fr not_active Withdrawn
-
2000
- 2000-09-07 DE DE60002224T patent/DE60002224T2/de not_active Expired - Fee Related
- 2000-09-07 AU AU72864/00A patent/AU7286400A/en not_active Abandoned
- 2000-09-07 KR KR1020027003126A patent/KR20020051918A/ko not_active Application Discontinuation
- 2000-09-07 WO PCT/EP2000/008869 patent/WO2001019941A1/fr active Search and Examination
- 2000-09-07 EP EP00960644A patent/EP1216288B1/fr not_active Expired - Lifetime
- 2000-09-07 AT AT00960644T patent/ATE237665T1/de not_active IP Right Cessation
- 2000-09-07 JP JP2001523713A patent/JP2003509569A/ja active Pending
Patent Citations (10)
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FR1405551A (fr) * | 1963-07-16 | 1965-07-09 | Exxon Research Engineering Co | Additifs anti-usure destinés à améliorer l'onctuosité d'hydrocarbures liquides |
US3672854A (en) * | 1969-12-03 | 1972-06-27 | Universal Oil Prod Co | Middle distillate |
US5378249A (en) * | 1993-06-28 | 1995-01-03 | Pennzoil Products Company | Biodegradable lubricant |
WO1997004044A1 (fr) * | 1995-07-14 | 1997-02-06 | Exxon Chemical Patents Inc. | Additifs et compositions de carburant les contenant |
EP0773278A1 (fr) * | 1995-11-13 | 1997-05-14 | Ethyl Petroleum Additives Limited | Additif pour combustible |
DE19614722A1 (de) * | 1996-04-15 | 1997-10-16 | Henkel Kgaa | Kältestabiles Schmier- und Kraftstoffadditiv |
EP0826765A1 (fr) * | 1996-08-27 | 1998-03-04 | Institut Francais Du Petrole | Compositions d'additifs améliorant le pouvoir lubrifiant des carburants et carburants les contenant |
WO1998011178A1 (fr) * | 1996-09-13 | 1998-03-19 | Exxon Research And Engineering Company | Additif pour mazouts legers a base de polyolester |
WO1998021293A1 (fr) * | 1996-11-13 | 1998-05-22 | Henkel Corporation | Lubrifiants pour carburant diesel |
FR2772783A1 (fr) * | 1997-12-24 | 1999-06-25 | Elf Antar France | Additif d'onctuosite pour carburant |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004026997A2 (fr) * | 2002-09-20 | 2004-04-01 | Unichema Chemie B.V. | Composition lubrifiante |
WO2004026997A3 (fr) * | 2002-09-20 | 2004-05-21 | Unichema Chemie Bv | Composition lubrifiante |
WO2005040315A1 (fr) * | 2003-10-22 | 2005-05-06 | Leuna Polymer Gmbh | Melange d'additifs utilise comme constituant d'une formulation a base d'huile minerale |
KR100749220B1 (ko) * | 2003-10-22 | 2007-08-13 | 로이나 폴리머 게엠베하 | 미네랄 오일 조성물의 성분으로서의 첨가제 혼합물 |
EA011358B1 (ru) * | 2003-10-22 | 2009-02-27 | Лейна Полимер Гмбх | Композиция минерального нефтетоплива, содержащая смесь присадок, способ ее получения и ее применение |
US7776801B2 (en) | 2003-10-22 | 2010-08-17 | Leuna Polymer Gmbh | Additive mixture as component of a mineral oil composition |
Also Published As
Publication number | Publication date |
---|---|
JP2003509569A (ja) | 2003-03-11 |
KR20020051918A (ko) | 2002-06-29 |
AU7286400A (en) | 2001-04-17 |
EP1216288A1 (fr) | 2002-06-26 |
EP1216288B1 (fr) | 2003-04-16 |
DE60002224D1 (de) | 2003-05-22 |
ATE237665T1 (de) | 2003-05-15 |
DE60002224T2 (de) | 2004-02-19 |
WO2001019941A1 (fr) | 2001-03-22 |
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