EP0255345A1 - Compositions de combustibles liquides - Google Patents
Compositions de combustibles liquides Download PDFInfo
- Publication number
- EP0255345A1 EP0255345A1 EP87306670A EP87306670A EP0255345A1 EP 0255345 A1 EP0255345 A1 EP 0255345A1 EP 87306670 A EP87306670 A EP 87306670A EP 87306670 A EP87306670 A EP 87306670A EP 0255345 A1 EP0255345 A1 EP 0255345A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fuel
- alkanes
- wax
- gas oil
- weight
- 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 82
- 239000000203 mixture Substances 0.000 title claims description 33
- 239000007788 liquid Substances 0.000 title claims description 4
- JXTPJDDICSTXJX-UHFFFAOYSA-N triacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 12
- 229920001577 copolymer Polymers 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 12
- 238000009826 distribution Methods 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000001993 wax Substances 0.000 description 49
- 239000000654 additive Substances 0.000 description 24
- 239000003921 oil Substances 0.000 description 20
- 230000000996 additive effect Effects 0.000 description 15
- -1 palmityl alcohol ester Chemical class 0.000 description 12
- 239000007789 gas Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 7
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000005673 monoalkenes Chemical class 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000005038 ethylene vinyl acetate Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000295 fuel oil Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004435 Oxo alcohol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- KUPLEGDPSCCPJI-UHFFFAOYSA-N tetracontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC KUPLEGDPSCCPJI-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- QKUNKVYPGIOQNP-UHFFFAOYSA-N 4,8,11,14,17,21-hexachlorotetracosane Chemical compound CCCC(Cl)CCCC(Cl)CCC(Cl)CCC(Cl)CCC(Cl)CCCC(Cl)CCC QKUNKVYPGIOQNP-UHFFFAOYSA-N 0.000 description 1
- JDOZUYVDIAKODH-SNAWJCMRSA-N 4-o-ethyl 1-o-methyl (e)-but-2-enedioate Chemical compound CCOC(=O)\C=C\C(=O)OC JDOZUYVDIAKODH-SNAWJCMRSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical class OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000193603 Percalates novemaculeata Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- HEJZJSIRBLOWPD-WCWDXBQESA-N didodecyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCCCC HEJZJSIRBLOWPD-WCWDXBQESA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FNMTVMWFISHPEV-WAYWQWQTSA-N dipropan-2-yl (z)-but-2-enedioate Chemical compound CC(C)OC(=O)\C=C/C(=O)OC(C)C FNMTVMWFISHPEV-WAYWQWQTSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- WNMORWGTPVWAIB-UHFFFAOYSA-N ethenyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC=C WNMORWGTPVWAIB-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- ZQZUENMXBZVXIZ-UHFFFAOYSA-N ethenyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC=C ZQZUENMXBZVXIZ-UHFFFAOYSA-N 0.000 description 1
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000004442 gravimetric analysis Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
-
- 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
- C10L1/16—Hydrocarbons
- C10L1/1691—Hydrocarbons petroleum waxes, mineral waxes; paraffines; alkylation products; Friedel-Crafts condensation products; petroleum resins; modified waxes (oxidised)
-
- 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
- C10L1/16—Hydrocarbons
- C10L1/1625—Hydrocarbons macromolecular compounds
- C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
- C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
-
- 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
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
- C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
-
- 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
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
- C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
-
- 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
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
- C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
Definitions
- This invention relates to distillate fuel compositions containing a flow improver.
- Heating oils and other distillate petroleum fuels e.g. diesel fuels
- the lowest temperature at which the fuel will still flow is generally known as the pour point.
- Effective wax crystal modification (as measured by CFPP and other operability tests, as well as simulated and field performance) can be achieved by flow improvers, mostly ethylene-vinyl acetate copolymer (EVA) based, in distillates containing up to 4 wt%-n-alkanes at l0°C below cloud point, as determined by gravimetric or DSC methods. Additive response in these distillates is normally stimulated by the refiner adjusting ASTM D-86 distillation characteristics of the distillates to increase the tail 90% to Final Boiling Point to deltas between 20°C and 25°C.
- EVA ethylene-vinyl acetate copolymer
- United States Patent 304069l proposes that the response of the same types of middle distillate to similar additives may be improved by the addition of a paraffinic distillate fraction containing normal alkanes higher than n-nexacosane and as high as n-tetracontane to provide from 0.l to 2 wt.% of normal alkanes of C24 and higher.
- a paraffinic distillate fraction containing normal alkanes higher than n-nexacosane and as high as n-tetracontane to provide from 0.l to 2 wt.% of normal alkanes of C24 and higher.
- a paraffinic distillate fraction containing normal alkanes higher than n-nexacosane and as high as n-tetracontane to provide from 0.l to 2 wt.% of normal alkanes of C24 and higher.
- the most difficult to treat are those fuels obtained from high wax crudes such as those from the crudes in Australia and the Far East where the total n alkane content of the distillate can be greater than 20%, the total content being C12 and higher n-alkanes as measured by Gas Liquid Chromatography.
- a middle distillate responsive to flow improvers may be obtained by adjusting the total wax content of the fuel to between 5.5 and l2 wt.%, preferably by blending of high and low wax content fuels.
- the wax content being that precipitated with methyl ethyl ketone from a l gram of the fuel at -20°C.
- a typical hard to treat distillate fuel containing 5 to l0 wt.% wax at l0°C below its cloud point and/or greater than 20 wt.% n-alkanes C 12+ has the following ASTM D-86 characteristics: Initial Boiling Point 2l2°C 5% 234°C l0% 243°C 20% 255°C 30% 263°C 40% 279°C 50% 288°C 60% 298°C 70% 303°C 80% 32l°C 90% 334°C 95% 343°C Final Boiling Point 36l°C
- a liquid fuel composition comprises a major proportion by weight of a distillate fuel containing between 4 and l0 wt.% wax at l0°C below cloud point and having a narrow n-alkane distribution, i.e. containing substantially no paraffins longer than n-triacontane (C30), a low temperature flow improver at 0.00l to 2.0 wt.% based on the weight of the distillate fuel and 0.00l to 2.0 wt.% of added n-alkanes where C24 and higher is greater than 0.35 wt.% of the fuel.
- Also according to this invention is the use as a cold flow improver for a distillate fuel containing between 4 and l0 wt.% of wax at l0°C below cloud point and having a narrow carbon distribution, i.e. containing substantially no paraffins longer than n-triacontane (C30) of mixture of a distillate fuel flow improver and added n-alkanes whose C24 and higher is greater than .35 wt.% of the weight of the fuel.
- n-triacontane C30
- the flow improvers that are employed in this invention may be any of those generally available although we prefer to use the type comprising copolymers of ethylene and at least one second unsaturated monomer.
- the second unsaturated monomer can be another monoolefin, e.g. a C3 to C18 alpha-monoolefin or it can be an unsaturated ester, as for example, vinyl acetate, vinyl butyrate, vinyl propionate, lauryl methacrylate, ethyl acrylate or the like.
- the second monomer can also be a mixture of an unsaturated mono or diester and a branched or straight chain alpha monoolefin.
- copolymers can also be used, as for example mixtures of a copolymer of ethylene and vinyl acetate with an alkylated polystyrene or with an acylated polystyrene.
- Alternative materials are the amino succinic acid derivatives, esters such as polyacrylates and esterified maleic anhydride copolymers, polyalpha olefins, etc.
- the preferred distillate fuel flow improver useful in this invention consists of l to 40, and preferably l to 20, more preferably 3 to 20 molar proportions of ethylene per molar proportion of the ethylenically unsaturated monomer, which latter monomer can be a single monomer or a mixture of such monomers in any proportion, said polymer being oil soluble and having a number average molecular weight in the range of about l,000 to 50,000, preferably about l,000 to about 5,000.
- Molecular weights can be measured by cryoscopic methods or by vapor phase osmometry, for example by using a Mechrolab Vapor Phase OsmometerModel 3l0A.
- the unsaturated monomers which may be homopolymerised or copolymerised with ethylene or with each other include unsaturated acids, acid anhydrides, and mono and diesters of the general formula: wherein R1 is hydrogen or methyl; R3 is a -OOCR4 or -COOR4 group wherein R4 is hydrogen or a C1 to C16, preferably C1 to C4 straight or branched chain alkyl group and R3 is hydrogen or -COOR4.
- the monomer, when R1 to R3 are hydrogen and R2 is -OOCR4 includes vinyl alcohol esters of C2 to C17 monocarboxylic acids.
- esters examples include vinyl acetate, vinyl isobutyrate, vinyl laurate, vinyl myristate, vinyl palmitate, etc.
- R2 is -COOR4
- esters include C8 oxo alcohol acrylate, methyl-acrylate, methyl methacrylate, lauryl acrylate, isobutyl methacrylate, palmityl alcohol ester of alpha-methacylic acid, C13 oxo alcohol esters of methacrylic acid, etc.
- Examples of monomers wherein R1 is hydrogen and R2 and R3 are-OOCR4 groups include mono C12 oxo alcohol fumarate, di-isopropyl maleate; di-lauryl fumarate; ethyl methyl fumarate; fumaric acid, maleic acid, etc.
- R2 is H and R1 is COOR4 and R3 is CG2 COOR4 such as the itaconates.
- unsaturated monomers copolymerizable with ethylene to prepare pour point depressants or flow improvers useful in this invention include C3 to C16 branched chain or straight-chain alpha monoolefins, as for example, propylene, n-octene-l, 2-ethyl decene-l, n-decene-l, etc.
- a copolymers of 3 to 40 moles of ethylene with one mole of a mixture of 30 to 99 mole percent of unsaturated ester and 70 to l mole percent of olefin could be used.
- copolymers that are formed are random copolymers consisting primarily of an ethylene polymer backbone along which are distributed side chains of hydrocarbon or oxy-substituted hydrocarbon.
- the alcohols used in preparing the esters mentioned above are isomeric mixtures of branched chain aliphatic primary alcohols prepared from olefins, such as polymers and copolymers of C3 to C4 monoolefins, reacted with carbon monoxide and hydrogen in the presence of a cobalt-containing catalyst such as cobalt carbonyl, at temperatures of about 300°F to 400°F, under pressures of about l,000 to 3,000 p.s.i. to form aldehydes.
- the resulting aldehyde product is then hydrogenated to form the alcohol, the latter being recovered by distillation from the hydrogenated product.
- the copolymers have a low degree of side chain branching; particularly they contain less than l0 preferably less than 8 methyl terminating side chains (other than the ester groups) per l00 methyl groups as measured by nuclear magnetic resonance, particularly 500 megaherz proton NMR analysis.
- the flow improver is used in a concentration in the range of from about 0.00l to about 2 wt.%, preferably from about 0.005 to about 0.2 percent by weight, based on the weight of the distillate fuel being treated.
- the second additive provides the n-alkanes greater than C24 and is preferably a wax having a carbon number distribution from about 20 to about 40.
- the wax consist predominantly of linear alkanes although it may also contain a small amount of branched hydrocarbons.
- the wax may be added as a pure wax or as a refinery stream such as a heavy atmospheric gas oil, vacuum gas oil or heavy cracked gas oil which contains the defined amount of waxes having carbon numbers in the required range. It is believed that the wax nucleates the crystallisation of the n-alkanes in the fuel and also co-crystallises with the first n-alkanes to precipitate from the fuel.
- the preferred n-alkane distribution of the added wax therefore depends upon the particular fuel. Whilst the C24 and higher n alkane component should be greater than 0.35 wt.% based on the fuel we prefer that it be greater than 0.5 wt.%.
- additives may also be used to give further improvements in low temperature properties, for example a diamide or preferably a half amide, half amine salt of a dicarboxylic acid or anhydride such as phthalic anhydride, and a secondary amine, the alkyl groups preferably containing l2 to 20 carbon atoms may be added.
- a particularly preferred compound is the half amide, half amine salt of phthalic acid and dihydrogenated tallow amine - Armeen 2HT (approx. 4 wt.% n-C14 alkyl, 30 wt.% n-C16 alkyl, 60 wt.% n-C18 alkyl, the remainder being unsaturated).
- the amount of diamide or half amide, half amine salt which is added is usually 0.00l to 2 wt.%, preferably 0.005 to 0.2 wt.%, based on the weight of distillate fuel.
- glycol esters such as those defined in our European Patent 0 06l 895B the esters and amines of maleic anhydide copolymers such as those defined in European Publication No 02l4786.
- the cold flow properties of the distillate fuel can be further improved by adding thereto a wax-naphthalene condensate.
- a typical condensate is prepared by chlorinating a wax containing n- and branched C18 to C39 paraffins (C26 average) to obtain a chlorinated wax containing about l5 weight % chlorine.
- the chlorowax thus obtained is polymerised with naphthalene via an alkylation reaction to give a condensate using containing alternating wax and naphthalene units.
- the amount of condensate added is usually 0.00005 to 0.l wt.% based on the weight of the distillate fuel.
- the additives of the present invention are frequently supplied as concentrates for incorporation into the bulk fuel and this invention further provides a concentrate comprising a solution containing from 30 to 70 wt.% preferably, 40 to 60 wt.% of a mixture of copolymer of ethylene and an other ethylenically unsaturated monomer and a hydrocarbon wax.
- Additive l 63 wt.% solution of a mixture of two ethylene vinyl acetate copolymers, marketed by Exxon Chemicals as ECA 8400.
- Additive 2 Additive l plus l0 wt.% of a wax naphthalene condensate.
- Additive 3 a mixture of (l) an ethylene-vinyl acetate copolymer (2 parts by weight), (2) a wax-napthalene condensate and (3) l part by weight of a half amide-half amine salt of phthalic acid and dihydrogenated tallow amine (Armeen 2HT).
- the amount of wax-napthalene condensate was 5 weight per cent of the total weight of copolymer (l) and half amide-half amine salt (2).
- Additive 4 A 45 wt.% solution of a high branched ethylene vinyl acetate copolymer of molecular weight about 2000 and vinyl acetate content about 30 wt.% prepared according to French Patent l46l008.
- Additive 5 A blend of ethylene vinyl acetate copolymers and fumarate vinyl acetate copolymers marketed by Exxon as Paraflow 206.
- Additive 6 A concentrate in an aromatic diluent of about 50 wt.% of a mixture of two ethylene-vinyl acetate copolymers in a ratio of about 75 wt.% of wax growth arrestor and about 25 wt.% of nucleator.
- the wax growth arrestor consists of ethylene and about 38 wt.% vinyl acetate, and has a number average molecular weight of about 25-35.
- the nucleator consists of ethylene and about l6 wt.% vinyl acetate and has a number average molecular weight of about 3000 (VPO). It is identified in UK Patent l37405l as copolymer H.
- CFPPT cold filter plugging point test
- Stretched across the mouth of the funnel is a 350 mesh screen having an area of about 0.45 square inches.
- the periodic tests are each initiated by applying a vacuum to the upper end of the pipette whereby oil is drawn through the screen up into the pipette to a mark indicating 20 ml. of oil.
- the test is repeated with each one degree drop in temperature until the oil fails to fill the pipette to a mark indicating 20 ml. of oil
- the test is repeated with each one degree drop in temperature until the oil fails to fill the pipette within 60 seconds.
- the temperature at which the last filtration commenced is recorded and reported as the cold filter plugging point.
- the value for the untreated fuel and the fuel containing l500 ppm of the ethylene/vinyl acetate copolymer solution as sole additive was -l°C.
- Varying amounts of the following commercially available waxes were then added to the fuel containing the ethylene/vinyl acetate copolymer.
- the n-alkane distributions of the fuel and the vacuum gas oil were
- the base fuel contained 23.40 wt.% of n-alkanes of C12 and higher.
- VGO vacuum gas oil
- n-alkane 33 a Heavy Cracked Distillate of cloud point +35°C, (max n-alkane 33)
- base fuel of cloud point + 3°C produced from Australian Bass Strait crude, having a 8.8 wt.% wax content as measured by wax precipation to a temperature l0°C below the cloud point.
- composition of the components was:
- the base fuel contained 27.3 wt.% of alkanes C12 and higher.
- the components were as follows:
- the base fuel contained 32 wt.% of alkanes C12 and higher.
- This example illustrates the improvement in response to flow improvers by replacing heavy atmospheric gas oil (HGO) with heavy cracked gas oil (HCO), Base Fuel l had a cloud point of -l°C and Base Fuel 2 of -2°C.
- HGO heavy atmospheric gas oil
- HCO heavy cracked gas oil
- the Components used were as follows:
- the Base Fuel l contained 22.8 wt.% n-alkanes C12 and higher and Base Fuel 2 27.6 wt.%.
- This example shows the effects of the addition of wax to a base of cloud point +5°C distillate fuel obtained from a chinese crude .
- the D-86 distillation of the distillate was:.
- the n-alkane distribution of the fuel and the added waxes were as follows:
- the base fuel contained 30.l wt.% n-alkanes of C12 and higher.
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- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8618397 | 1986-07-29 | ||
GB868618397A GB8618397D0 (en) | 1986-07-29 | 1986-07-29 | Liquid fuel compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0255345A1 true EP0255345A1 (fr) | 1988-02-03 |
EP0255345B1 EP0255345B1 (fr) | 1992-11-25 |
Family
ID=10601825
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP87306670A Expired - Lifetime EP0255345B1 (fr) | 1986-07-29 | 1987-07-28 | Compositions de combustibles liquides |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0255345B1 (fr) |
JP (1) | JP2541993B2 (fr) |
KR (1) | KR950014389B1 (fr) |
CN (1) | CN1020631C (fr) |
DE (1) | DE3782773T2 (fr) |
ES (1) | ES2052569T3 (fr) |
GB (1) | GB8618397D0 (fr) |
IN (1) | IN168378B (fr) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994017159A1 (fr) * | 1993-01-29 | 1994-08-04 | Exxon Chemical Patents Inc. | Compositions de petrole et de mazout |
WO1999028418A1 (fr) * | 1997-12-03 | 1999-06-10 | Infineum Usa L.P. | Additifs et compositions d'huiles |
WO1999028417A1 (fr) * | 1997-12-03 | 1999-06-10 | Infineum Usa L.P. | Additifs et compositions de gasoils |
WO1999028416A1 (fr) * | 1997-12-03 | 1999-06-10 | Infineum Usa L.P. | Additifs et compositions d'huiles |
WO1999028419A1 (fr) * | 1997-12-03 | 1999-06-10 | Infineum Usa L.P. | Additifs et compositions d'huiles |
EP0960930A1 (fr) * | 1998-05-15 | 1999-12-01 | Tonen Corporation | composition d huile diesel |
WO2000044857A2 (fr) * | 1998-12-11 | 2000-08-03 | Infineum Usa Lp | Materiaux macromoleculaires |
EP1690919A1 (fr) * | 2005-02-11 | 2006-08-16 | Infineum International Limited | Compositions d'huile combustible. |
EP2078743A1 (fr) | 2008-01-10 | 2009-07-15 | Shell Internationale Researchmaatschappij B.V. | Composition de carburant |
CN1818040B (zh) * | 2005-02-11 | 2012-02-29 | 英菲诺姆国际有限公司 | 燃料油组合物 |
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GB1264684A (fr) * | 1968-09-17 | 1972-02-23 | ||
GB1264638A (fr) * | 1968-09-17 | 1972-02-23 | ||
GB1266037A (fr) * | 1968-09-17 | 1972-03-08 | ||
US3733184A (en) * | 1971-02-09 | 1973-05-15 | Exxon Co | Composition for improving air-fuel ratio distribution in internal combustion engines |
FR2305492A1 (fr) * | 1975-03-28 | 1976-10-22 | Exxon Research Engineering Co | Fuel-oil comportant un additif compose pour en ameliorer l'ecoulement a froid |
EP0239320A2 (fr) * | 1986-03-18 | 1987-09-30 | Exxon Chemical Patents Inc. | Compositions combustibles liquides |
Family Cites Families (10)
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AR208270A1 (es) * | 1972-05-08 | 1976-12-20 | Texaco Development Corp | Un poli(acrilato de n-alquilo)interpolimerico |
DE2837341C2 (de) * | 1978-08-26 | 1983-02-17 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von organischen Mono- und Polyisocyanaten durch thermische Spaltung der Hydrochloride trisubstituierter Harnstoffe |
US4464182A (en) * | 1981-03-31 | 1984-08-07 | Exxon Research & Engineering Co. | Glycol ester flow improver additive for distillate fuels |
JPS57207696A (en) * | 1981-06-17 | 1982-12-20 | Nippon Sekiyu Seisei Kk | Diesel gas oil composition |
JPS5839472A (ja) * | 1981-09-03 | 1983-03-08 | Mitsubishi Electric Corp | プリンタ装置 |
JPS5880386A (ja) * | 1981-11-06 | 1983-05-14 | Nippon Cooper Kk | 燃料油添加剤 |
JPS597757A (ja) * | 1982-07-05 | 1984-01-14 | Diesel Kiki Co Ltd | 内燃スタ−リング機関 |
JPS602355A (ja) * | 1983-06-21 | 1985-01-08 | 第一工業製薬株式会社 | 金属塗装物 |
JPS6017320A (ja) * | 1983-07-08 | 1985-01-29 | Tsuneo Hirai | 粉粒体分配供給方法 |
JPS6035396A (ja) * | 1984-06-15 | 1985-02-23 | Nec Corp | 半導体メモリ装置の駆動方法 |
-
1986
- 1986-07-29 GB GB868618397A patent/GB8618397D0/en active Pending
-
1987
- 1987-07-24 IN IN630/DEL/87A patent/IN168378B/en unknown
- 1987-07-25 KR KR1019870008117A patent/KR950014389B1/ko not_active IP Right Cessation
- 1987-07-28 ES ES87306670T patent/ES2052569T3/es not_active Expired - Lifetime
- 1987-07-28 DE DE8787306670T patent/DE3782773T2/de not_active Expired - Fee Related
- 1987-07-28 EP EP87306670A patent/EP0255345B1/fr not_active Expired - Lifetime
- 1987-07-29 CN CN87106411A patent/CN1020631C/zh not_active Expired - Fee Related
- 1987-07-29 JP JP62189970A patent/JP2541993B2/ja not_active Expired - Fee Related
Patent Citations (6)
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GB1264684A (fr) * | 1968-09-17 | 1972-02-23 | ||
GB1264638A (fr) * | 1968-09-17 | 1972-02-23 | ||
GB1266037A (fr) * | 1968-09-17 | 1972-03-08 | ||
US3733184A (en) * | 1971-02-09 | 1973-05-15 | Exxon Co | Composition for improving air-fuel ratio distribution in internal combustion engines |
FR2305492A1 (fr) * | 1975-03-28 | 1976-10-22 | Exxon Research Engineering Co | Fuel-oil comportant un additif compose pour en ameliorer l'ecoulement a froid |
EP0239320A2 (fr) * | 1986-03-18 | 1987-09-30 | Exxon Chemical Patents Inc. | Compositions combustibles liquides |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994017159A1 (fr) * | 1993-01-29 | 1994-08-04 | Exxon Chemical Patents Inc. | Compositions de petrole et de mazout |
US6254650B1 (en) | 1997-12-03 | 2001-07-03 | Exxon Chemical Patents Inc | Fuel oil additives and compostions |
WO1999028418A1 (fr) * | 1997-12-03 | 1999-06-10 | Infineum Usa L.P. | Additifs et compositions d'huiles |
WO1999028417A1 (fr) * | 1997-12-03 | 1999-06-10 | Infineum Usa L.P. | Additifs et compositions de gasoils |
WO1999028416A1 (fr) * | 1997-12-03 | 1999-06-10 | Infineum Usa L.P. | Additifs et compositions d'huiles |
WO1999028419A1 (fr) * | 1997-12-03 | 1999-06-10 | Infineum Usa L.P. | Additifs et compositions d'huiles |
US6458175B1 (en) | 1997-12-03 | 2002-10-01 | Exxon Chemical Patents Inc. | Oil additives and compositions |
US6251146B1 (en) | 1997-12-03 | 2001-06-26 | Exxon Chemical Patents Inc. | Fuel oil composition containing mixture of wax additives |
EP0960930A1 (fr) * | 1998-05-15 | 1999-12-01 | Tonen Corporation | composition d huile diesel |
US6136049A (en) * | 1998-05-15 | 2000-10-24 | Tonen Corporation | Diesel fuel oil composition |
WO2000044857A3 (fr) * | 1998-12-11 | 2000-11-30 | Infineum Usa Lp | Materiaux macromoleculaires |
WO2000044857A2 (fr) * | 1998-12-11 | 2000-08-03 | Infineum Usa Lp | Materiaux macromoleculaires |
EP1690919A1 (fr) * | 2005-02-11 | 2006-08-16 | Infineum International Limited | Compositions d'huile combustible. |
CN1818040B (zh) * | 2005-02-11 | 2012-02-29 | 英菲诺姆国际有限公司 | 燃料油组合物 |
EP2078743A1 (fr) | 2008-01-10 | 2009-07-15 | Shell Internationale Researchmaatschappij B.V. | Composition de carburant |
WO2009087202A2 (fr) * | 2008-01-10 | 2009-07-16 | Shell Internationale Research Maatschappij B.V. | Composition de carburant |
WO2009087202A3 (fr) * | 2008-01-10 | 2009-12-10 | Shell Internationale Research Maatschappij B.V. | Composition de carburant |
US8273137B2 (en) | 2008-01-10 | 2012-09-25 | Shell Oil Company | Fuel composition |
Also Published As
Publication number | Publication date |
---|---|
CN87106411A (zh) | 1988-04-13 |
GB8618397D0 (en) | 1986-09-03 |
KR880001795A (ko) | 1988-04-26 |
ES2052569T3 (es) | 1994-07-16 |
DE3782773T2 (de) | 1993-04-01 |
JPS63108096A (ja) | 1988-05-12 |
CN1020631C (zh) | 1993-05-12 |
KR950014389B1 (ko) | 1995-11-27 |
DE3782773D1 (de) | 1993-01-07 |
JP2541993B2 (ja) | 1996-10-09 |
IN168378B (fr) | 1991-03-23 |
EP0255345B1 (fr) | 1992-11-25 |
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