EP1651740A1 - Compositions d'essence - Google Patents
Compositions d'essenceInfo
- Publication number
- EP1651740A1 EP1651740A1 EP04741982A EP04741982A EP1651740A1 EP 1651740 A1 EP1651740 A1 EP 1651740A1 EP 04741982 A EP04741982 A EP 04741982A EP 04741982 A EP04741982 A EP 04741982A EP 1651740 A1 EP1651740 A1 EP 1651740A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- gasoline
- nitrogen
- ppmw
- ethyl levulinate
- composition according
- 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
- 239000003502 gasoline Substances 0.000 title claims abstract description 46
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003599 detergent Substances 0.000 claims abstract description 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- -1 hydrocarbyl amine Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 238000002485 combustion reaction Methods 0.000 claims description 4
- 239000000446 fuel Substances 0.000 description 22
- 229920002367 Polyisobutene Polymers 0.000 description 11
- 239000000654 additive Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 239000012530 fluid Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- UAGJVSRUFNSIHR-UHFFFAOYSA-N Methyl levulinate Chemical compound COC(=O)CCC(C)=O UAGJVSRUFNSIHR-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229920013639 polyalphaolefin Polymers 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 229940040102 levulinic acid Drugs 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000003749 cleanliness Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 150000004730 levulinic acid derivatives Chemical class 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- WETOYPNHZMSVFZ-UHFFFAOYSA-N 2-methylpropyl 4-oxopentanoate Chemical compound CC(C)COC(=O)CCC(C)=O WETOYPNHZMSVFZ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- CKOYRRWBOKMNRG-UHFFFAOYSA-N Furfuryl acetate Chemical compound CC(=O)OCC1=CC=CO1 CKOYRRWBOKMNRG-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- 240000002426 Persea americana var. drymifolia Species 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940005460 butyl levulinate Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003254 gasoline additive Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940058352 levulinate Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- MGJRGGIHFUREHT-UHFFFAOYSA-N propan-2-yl 4-oxopentanoate Chemical compound CC(C)OC(=O)CCC(C)=O MGJRGGIHFUREHT-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- 239000013638 trimer Substances 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
- 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
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
-
- 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
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
-
- 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
- C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
-
- 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
-
- 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
- C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
-
- 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
- C10L1/192—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
Definitions
- This invention relates to gasoline compositions, more particularly to such compositions containing a levulinate ester, and to their preparation and use.
- Levulinate esters esters of levulinic acid
- Their preparation by reaction of the appropriate alcohol with furfuryl acetate are described in Zh. Prikl. Khim. (Leningrad) (1969) 42(4), 958-9, and in particular the methyl, ethyl, propyl, butyl, pentyl and hexyl esters.
- WO 9421753 discloses fuels for internal combustion engines, including both gasoline and diesel fuel, containing proportions (e.g.
- esters of C to Cg keto-carbonic acids, preferably levulinic acid with C ⁇ _ to C22 alcohols.
- Esters with C ⁇ to Cg alcohols are described as being particularly suitable for inclusion in gasolines, and esters with C9 to C22 alcohols are described as being particularly suitable for inclusion in diesel fuels.
- the examples in WO 9421753 are all of the inclusion of quantities of levulinate esters in gasolines, for improvement in octane numbers (RON and MON) .
- 10% v methyl levulinate is incorporated in different base gasolines.
- Examples 2 to 6 employ, respectively, ethyl levulinate, n-propyl levulinate, isopropyl levulinate, isobutyl levulinate and sec-butyl levulinate.
- Examples 8 and 9 employ 10% v of mixtures of methyl levulinate and methyl formate, in 1:1 and 2:1 ratios, respectively.
- Example 11 employs a range of proportions from 5% v to 90% v of methyl levulinate in unleaded Eurosuper gasoline.
- WO 03002696 (AAE Tech.
- Int. discloses a fuel composition incorporating levulinic acid, or a functional derivative thereof, with the object of providing more oxygen by volume than ethanol or traditional oxygenates such as MTBE or ETBE, giving little or no increase in fuel Reid vapour pressure and little or no effect on the flash point of the base fuel.
- the functional derivative is preferably an alkyl derivative, preferably a C ⁇ to C ⁇ Q alkyl derivative. Ethyl levulinate is said to be preferred, with methyl levulinate a preferred alternative.
- the levulinic acid or functional derivative is preferably used to form 0.1 to 5% v of the fuel.
- WO 03002696 further incorporates 0.1 to 5% v of a further additive selected from the groups consisting of: a) the optionally alkoxylated linear or branched saturated or unsaturated monoalcohols having 8 to 24 C atoms, containing zero or 1 to 20 mol of ethylene oxide and/or 1 to 5 mol of propylene oxide per mol of alcohol, or b) the polyols having 2 to 6 carbon atoms, optionally partially esterified with fatty acids having 1 to 24 carbon atoms, or c) the alkoxylated fatty acids having 12 to 24 carbon atoms and 4 to 20 mol of ethylene oxide per mol of fatty acid, or d) the ethoxylated dimeric fatty acids.
- a further additive selected from the groups consisting of: a) the optionally alkoxylated linear or branched saturated or unsaturated monoalcohols having 8 to 24 C atoms, containing zero or 1 to 20 mol of ethylene oxide and/or
- Such fuels are preferably diesel fuels (Page 7, lines 11 to 22) .
- the fuel is substantially free of alkoxylated compounds and of long chain alkyl alcohols, but it contains an additive of formula R-CO-NR ⁇ -R ⁇ , where R is a saturated or unsaturated, linear or branched, alkyl radical having 6 to 21 carbon atoms (corresponding to number average molecular weight in the range 85 to
- R 1 and R 2 each independently represent a Ci to
- a fuel composition which incorporates the levulinic acid, or functional derivative thereof, together with a nitrogen source in the form of (Page 9 lines 8 to 15) a nitrogen compound selected from the group consisting of ammonia, hydrazine, alkyl hydrazine, dialkyl hydrazine, urea, ethanolamine, monoalkyl ethanolamine, and dialkyl ethanolamine wherein alkyl is independently selected from methyl, ethyl, n- propyl or isopropyl. Urea is preferred.
- the nitrogen compound may be an anhydrous compound or a hydrous compound, e.g.
- aqueous solution an aqueous solution, and may be up to a 5% w/w aqueous solution.
- Cetane boosters, demulsifers and bio-diesel type fuels may also be present (Page 10, lines 1 to 29) .
- WO 03002696 states (Page 11, line 31) that
- compositional and test result data consists of the following sentences :- "Specification gasoline blends containing up to 5.0% ethyl levulinate, 1.0% water and 2.0% non-ionic surfactant were found to have similar RVPs to the base gasoline.”, and "Specification diesel blends containing up to 5.0% ethyl levulinate, 1.0% water and 2.0% non-ionic surfactant were found to have similar flash points to the base diesel.” It has now surprisingly been found that gasoline compositions containing ethyl levulinate together with particular nitrogen-containing detergents can give surprisingly enhanced engine cleanliness performance, and that gasoline compositions containing ethyl levulinate are surprisingly more compatible with certain elastomeric seal materials than gasoline compositions containing similar concentrations of methyl levulinate.
- a gasoline composition comprising a major amount of a gasoline suitable for use in a spark ignition engine, 1 to 15% v of ethyl levulinate, and 20 to 2000 ppmw of a nitrogen-containing detergent containing a hydrocarbyl group having a number average molecular weight in the range 750 to 6000.
- the ethyl levulinate concentration in the gasoline composition accords with one or more of the following parameters : - (i) it is at least 1.5% v, (ii) it is at least 2% v, (iii) it is at least 3% v, (iv) it is at least 4% v, (v) it is up to 12% v, (vi) it is up to 10% v, (vii) it is up to 8% v, (viii) it is up to 6% v, with ranges having features (i) and (v) , (ii) and (vi) , ( ⁇ i) and (vii) , and (v) and (viii) respectively being progressively more preferred.
- the gasoline composition preferably contains 50 to
- the nitrogen-containing detergent containing a hydrocarbyl group having a number average molecular weight (Mn) in the range 750 to 6000 may be an amine, e.g. a polyisobutylene mono-amine or polyamine, such as a polyisobutylene ethylene diamine, or N-polyisobutenyl- N' , N' -dimethyl-1, 3-diaminopropane, or amide e.g. a polyisobutenyl succinimide, and are variously described, for example, in US Patent 5,855,629 and WO 0132812.
- the nitrogen-containing detergent may be a Mannich amine detergent, for example a Mannich amine detergent as described in US Patent 5,725,612.
- a particularly preferred nitrogen-containing detergent is hydrocarbyl amine of formula RI-NH2, wherein R! represents a group R 2 or a group R2-CH2 ⁇ and R2 represents a hydrocarbyl group having a number average molecular weight in the range 750 to 6000, preferably in the range 900 to 3000, more preferably 950 to 2000, and most preferably in the range 950 to 1350, e.g. a polybutenyl or polyisobutenyl group having a number average molecular weight in the range 950 to 1050.
- the nitrogen-containing detergents are known materials and may be prepared by known methods or by methods analogous to known methods.
- US Patent 4,832,702 describes the preparation of polybutenyl and polyisobutenyl amines from an appropriate polybutene or polyisobutene by hydroformylation and subsequent amination of the resulting oxo product under hydrogenating conditions.
- Suitable hydrocarbyl amines are obtainable from BASF A.G., under the trade mark "Kerocom".
- the gasoline composition may additionally contain one or more carrier fluids, corrosion inhibitors, anti-oxidants, dyes, dehazers, metal deactivators, detergents other than a nitrogen- containing detergent containing a hydrocarbyl group as defined above (e.g. a polyether amine), friction modifiers, diluents and markers.
- carrier fluids are polyolefins, e.g. polyisobutylene and polyalphaolefins, and polyoxyalkylene compounds. Carrier fluids may conveniently be employed in total concentrations in the range 20 to 8000 ppmw, e.g. 50 to 500 ppmw.
- Polyalphaolefin carrier fluids are primarily trimers, tetramers and pentamers, and synthesis of such materials is outlined in Campen et al. "Growing use of synlubes", Hydrocarbon Processing, February 1982, Pages 75 to 82.
- the polyalphaolefin may be unhydrotreated, but it is preferably a hydrogenated oligomer.
- the polyalphaolefin is preferably derived from an alphaolefinic monomer containing from 8 to 12 carbon atoms. Furthermore, it preferably has viscosity at 100°C in the range 6xl0 ⁇ 6 to 1x10" ⁇ m 2 /s (6 to 10 centistokes) .
- Polyalphaolefins derived from decene-1 are very suitable.
- Polyalphaolefin having a viscosity at 100°C of 8xl0 ⁇ 6 m 2 /s (8 centistokes) are very suitable.
- Polyoxyalkylene carrier fluids, which are very effective, preferably have the formula II
- R ⁇ and R ⁇ independently represent hydrogen atoms or hydrocarbyl, preferably C__4fj hydrocarbyl, e.g. alkyl, cycloalkyl, phenyl or alkyl-phenyl groups, each R ⁇ > independently represents an alkylene, preferably C2_g alkylene, group, and p is such that Mn of the polyoxyalkylene compound is in the range 400 to 3000, preferably 700 to 2000, more preferably 1000 to 2000.
- R 3 represents a Cg-20 alkyl group and R 4 represents a hydrogen atom.
- R 3 preferably represents a Cg-18 alkyl group, more preferably a Cg-is alkyl group.
- R3 may conveniently be a mixture of Cg_ ⁇ 5 alkyl groups.
- the groups R ⁇ are preferably 1,2 alkylene groups.
- each group R5 independently represents a C2- alkylene group, e.g. an ethylene, 1,2- propylene or 1,2-butylene group.
- Very effective results have been obtained when each group R ⁇ represents a 1,2- propylene group.
- Number average molecular weights, e.g. of hydrocarbons such as polyalkenes, may be determined by several techniques which give closely similar results.
- Mn may be determined by vapour phase osmometry (VPO) (ASTM D 3592) or by modern gel permeation chromatography (GPC) , e.g.
- Very suitable friction modifiers are the fatty acid salt friction modifiers disclosed in DE-A-19955651 (BASF) (e.g. that described in Example 1 thereof), e.g. in an amount in the range 5 to 1000 ppmw, preferably 25 to 400 ppmw, and more preferably 50 to 200 ppmw.
- gasolines suitable for use in spark ignition engines are mixtures of hydrocarbons having boiling points in the range from 25°C to 232°C and comprising mixtures of saturated hydrocarbons, olefinic hydrocarbons and aromatic hydrocarbons.
- Preferred are gasoline blends having a saturated hydrocarbon content ranging from 40 to 80 per cent volume, an olefinic hydrocarbon content ranging from 0 to 30 per cent volume and an aromatic hydrocarbon content ranging from 10 to 60 per cent volume.
- the gasoline can be derived from straight run gasoline, polymer gasoline, natural gasoline, dimer- or trimerised olefins, synthetically produced aromatic hydrocarbon mixtures from thermally or catalytically reformed hydrocarbons, or from catalytically cracked or thermally cracked petroleum stocks, or mixtures thereof.
- the hydrocarbon composition and octane level of the gasoline are not critical.
- the octane level, (R+M)/2 will generally be above 85.
- Any conventional gasoline can be used.
- hydrocarbons can be replaced by up to substantial amounts of conventional alcohols or ethers conventionally known for use in gasoline.
- the gasoline is preferably lead-free, and this may be required by law. Where permitted, lead-free antiknock compounds and/or valve-seat recession protectant compounds (e.g. known potassium salts, sodium salts or phosphorous compounds) may be present.
- Modern gasolines are inherently low-sulphur fuels, e.g. containing less than 200 ppmw sulphur.
- the invention further provides a process for the preparation of a gasoline composition of the invention as defined above which comprises bringing into admixture the gasoline, the ethyl levulinate and the nitrogen- containing detergent.
- the fatty acid salt, the co-additive, and any additional components such as corrosion inhibitors, anti-oxidants, etc., as listed above, may be co-mixed, preferably together with suitable diluent (s), in an additive concentrate, and the additive concentrate may be dispersed into gasoline, in suitable quantity to result in a composition of the invention.
- the invention also provides a method of operating a spark-ignition engine, which comprises bringing into the combustion chambers of said engine a gasoline composition of the invention as defined above.
- the method of the invention may lead to any of a number of advantageous effects, including good engine keep-clean performance, especially in relation to inlet- system deposits, and clean-up performance can be achieved at the higher concentrations of the nitrogen-containing detergent, advantageous octane performance (RON and MON) and advantageous Reid vapour pressure.
- the invention will be further understood from the following illustrative examples in which, unless otherwise indicated, parts and percentages are by weight and temperatures are in degrees Celsius.
- base fuel used was an unleaded gasoline (95 ULG) of RON 98.9, MON 86.6, and having sulphur content (ASTM D 2622-94) of 138 ppmw, aromatics content of 50.7% v/v and olefins content 7.5% v/v (ASTM D6623-01 (procedure C) ) , Density (DIN 51757/V4) 779.1 kg/m 3 , distillation (ISO 3405/88) IBP 35.4°, 95% v/v 174.4, FBP 203°C. Fuels were blended with additives by adding additive to base fuel at ambient temperature (20°C) and homogenising.
- Ethyl levulinate (ex Avocado Chemicals, cat. No. 15001); "DP" - this was a standard commercial gasoline additive package, containing a polyisobutyleneamine detergent, a synthetic carrier oil and a conventional corrosion inhibitor, corresponding closely to additive package PI of Example 3 of DE-A-19955651.
- the polyisobutyleneamine detergent was a polyisobutylene monoamine (PIBA) ex BASF, in which the polyisobutylene (PIB) chain has a number average molecular weight of approximately 1000.
- the synthetic carrier oil was a polyether carrier being a polyoxypropylene glycol hemiether, containing 15 to 30 propylene oxide units prepared using a mixture of alkanols in the 05-15 ran g as initiators, and having Mn in the range 1000 to 2000.
- the additive package contained about 68% in non-volatile matter, about 27 %w of the package being the PIBA and 40 %w of the package being carrier fluid.
- MPI has a lambda sensor and exhaust gas recirculation.
- inlet parts and combustion chambers were cleaned and new pre-weighed inlet valves and new spark plugs fitted to the engine, a new oil filter was fitted and the engine filled with new engine oil.
- the engine was run for a period of 69 hours under a test procedure corresponding to that of CEC-F-05-A-93, except that the Toyota 3S-FE engine was used in place of the Mercedes Benz M 102 E engine specified in the CEC-F- 05-A-93 procedure, and the torque values differ from those specified in CEC-F-05-A-93 to compensate for the different BMEP (break mean effective pressure) values achieved by the Mercedes Benz M 102 E and the Toyota 3S- FE engines.
- the specific conditions of each cycle were:- Stage time (sees) rpm torque (Nm) 1 30 850 idle 2 60 1300 26 3 120 1850 28 4 60 3000 30
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- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
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Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04741982A EP1651740B1 (fr) | 2003-07-15 | 2004-07-08 | Compositions d'essence |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03254454 | 2003-07-15 | ||
PCT/EP2004/051423 WO2005014759A1 (fr) | 2003-07-15 | 2004-07-08 | Compositions d'essence |
EP04741982A EP1651740B1 (fr) | 2003-07-15 | 2004-07-08 | Compositions d'essence |
Publications (2)
Publication Number | Publication Date |
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EP1651740A1 true EP1651740A1 (fr) | 2006-05-03 |
EP1651740B1 EP1651740B1 (fr) | 2012-05-02 |
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ID=34072685
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP04741982A Expired - Lifetime EP1651740B1 (fr) | 2003-07-15 | 2004-07-08 | Compositions d'essence |
Country Status (14)
Country | Link |
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US (1) | US20050016058A1 (fr) |
EP (1) | EP1651740B1 (fr) |
JP (1) | JP5048329B2 (fr) |
CN (1) | CN100432196C (fr) |
AR (1) | AR046256A1 (fr) |
AT (1) | ATE556128T1 (fr) |
AU (1) | AU2004263662B2 (fr) |
BR (1) | BRPI0412640A (fr) |
CA (1) | CA2533001C (fr) |
MY (1) | MY137521A (fr) |
NO (1) | NO20060707L (fr) |
NZ (1) | NZ544457A (fr) |
WO (1) | WO2005014759A1 (fr) |
ZA (1) | ZA200600204B (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US6494879B2 (en) * | 1998-10-15 | 2002-12-17 | Scimed Life Systems, Inc. | Treating urinary retention |
WO2007012585A1 (fr) * | 2005-07-25 | 2007-02-01 | Shell Internationale Research Maatschappij B.V. | Compositions combustibles |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3611230A1 (de) * | 1986-04-04 | 1987-10-08 | Basf Ag | Polybutyl- und polyisobutylamine, verfahren zu deren herstellung und diese enthaltende kraft- und schmierstoffzusammensetzungen |
DE4308053C2 (de) * | 1993-03-13 | 1997-05-15 | Veba Oel Ag | Flüssige unverbleite Kraftstoffe |
TW477784B (en) * | 1996-04-26 | 2002-03-01 | Shell Int Research | Alkoxy acetic acid derivatives |
US5725612A (en) * | 1996-06-07 | 1998-03-10 | Ethyl Corporation | Additives for minimizing intake valve deposits, and their use |
US6203584B1 (en) * | 1998-03-31 | 2001-03-20 | Chevron Chemical Company Llc | Fuel composition containing an amine compound and an ester |
JP4026980B2 (ja) * | 1999-03-31 | 2007-12-26 | 株式会社ジョモテクニカルリサーチセンター | ガソリン |
US6723141B1 (en) * | 1999-11-04 | 2004-04-20 | Shell Oil Company | Additive concentration |
US20020143216A1 (en) * | 2001-01-26 | 2002-10-03 | Kazushi Tsurutani | Motor gasoline composition |
US6482243B2 (en) * | 2001-03-22 | 2002-11-19 | J.T. Granatelli Lubricants, Inc. | Fuel reformulator |
GB0111679D0 (en) * | 2001-05-12 | 2001-07-04 | Aae Tech Int Ltd | Fuel composition |
EP1737810A2 (fr) * | 2004-03-24 | 2007-01-03 | E.I.Du pont de nemours and company | Preparation d'esters d'acide levulinique a partir d'alpha-angelica lactone et d'alcools |
-
2004
- 2004-07-08 BR BRPI0412640-8A patent/BRPI0412640A/pt not_active IP Right Cessation
- 2004-07-08 AU AU2004263662A patent/AU2004263662B2/en not_active Ceased
- 2004-07-08 WO PCT/EP2004/051423 patent/WO2005014759A1/fr active Search and Examination
- 2004-07-08 AT AT04741982T patent/ATE556128T1/de active
- 2004-07-08 CA CA2533001A patent/CA2533001C/fr not_active Expired - Fee Related
- 2004-07-08 JP JP2006519923A patent/JP5048329B2/ja not_active Expired - Fee Related
- 2004-07-08 EP EP04741982A patent/EP1651740B1/fr not_active Expired - Lifetime
- 2004-07-08 CN CNB200480020221XA patent/CN100432196C/zh not_active Expired - Fee Related
- 2004-07-08 NZ NZ544457A patent/NZ544457A/en unknown
- 2004-07-13 MY MYPI20042800A patent/MY137521A/en unknown
- 2004-07-13 AR ARP040102460A patent/AR046256A1/es unknown
- 2004-07-13 US US10/889,790 patent/US20050016058A1/en not_active Abandoned
-
2006
- 2006-01-09 ZA ZA200600204A patent/ZA200600204B/en unknown
- 2006-02-14 NO NO20060707A patent/NO20060707L/no not_active Application Discontinuation
Non-Patent Citations (1)
Title |
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See references of WO2005014759A1 * |
Also Published As
Publication number | Publication date |
---|---|
ATE556128T1 (de) | 2012-05-15 |
CN1823153A (zh) | 2006-08-23 |
CA2533001C (fr) | 2013-04-30 |
NZ544457A (en) | 2009-06-26 |
JP2009513750A (ja) | 2009-04-02 |
EP1651740B1 (fr) | 2012-05-02 |
MY137521A (en) | 2009-02-27 |
ZA200600204B (en) | 2007-03-28 |
WO2005014759A1 (fr) | 2005-02-17 |
CA2533001A1 (fr) | 2005-02-17 |
NO20060707L (no) | 2006-02-14 |
BRPI0412640A (pt) | 2006-09-26 |
CN100432196C (zh) | 2008-11-12 |
AU2004263662A1 (en) | 2005-02-17 |
AR046256A1 (es) | 2005-11-30 |
US20050016058A1 (en) | 2005-01-27 |
AU2004263662B2 (en) | 2008-02-28 |
JP5048329B2 (ja) | 2012-10-17 |
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