US20120102825A1 - Ethylene/vinyl acetate/unsaturated esters terpolymer as an additive for improving the resistance to cold of liquid hydrocarbons such as middle distillates and fuels - Google Patents
Ethylene/vinyl acetate/unsaturated esters terpolymer as an additive for improving the resistance to cold of liquid hydrocarbons such as middle distillates and fuels Download PDFInfo
- Publication number
- US20120102825A1 US20120102825A1 US13/381,554 US201013381554A US2012102825A1 US 20120102825 A1 US20120102825 A1 US 20120102825A1 US 201013381554 A US201013381554 A US 201013381554A US 2012102825 A1 US2012102825 A1 US 2012102825A1
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- United States
- Prior art keywords
- fuels
- copolymer
- filterability
- moles
- ppm
- 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.)
- Abandoned
Links
- 239000000654 additive Substances 0.000 title claims abstract description 61
- 239000000446 fuel Substances 0.000 title claims abstract description 33
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 239000005977 Ethylene Substances 0.000 title claims abstract description 18
- 230000000996 additive effect Effects 0.000 title claims abstract description 17
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 229920001897 terpolymer Polymers 0.000 title claims description 26
- 229930195733 hydrocarbon Natural products 0.000 title claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 15
- 239000007788 liquid Substances 0.000 title description 2
- 229920001577 copolymer Polymers 0.000 claims abstract description 46
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 14
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 9
- 239000004711 α-olefin Substances 0.000 claims abstract description 7
- IJRVDOPVQJSPRP-UHFFFAOYSA-N octan-4-yl prop-2-enoate Chemical compound CCCCC(CCC)OC(=O)C=C IJRVDOPVQJSPRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 230000000903 blocking effect Effects 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 9
- 239000002283 diesel fuel Substances 0.000 claims description 5
- 238000002485 combustion reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000003350 kerosene Substances 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 238000009434 installation Methods 0.000 claims description 3
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- 239000003225 biodiesel Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- 239000004071 soot Substances 0.000 claims description 2
- 230000000593 degrading effect Effects 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 17
- -1 alkyl vinyl ethers Chemical class 0.000 description 14
- 238000000034 method Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 239000002028 Biomass Substances 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000010773 plant 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
- 239000001993 wax Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical class COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- NKRVGWFEFKCZAP-UHFFFAOYSA-N 2-ethylhexyl nitrate Chemical compound CCCCC(CC)CO[N+]([O-])=O NKRVGWFEFKCZAP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 239000003999 initiator Substances 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
- 238000005259 measurement Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 125000003367 polycyclic group Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 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
- C10L1/18—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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
- C10L10/16—Pour-point depressants
-
- 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
- C10L2200/043—Kerosene, jet fuel
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
- C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
- C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
- C10L2200/0446—Diesel
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0461—Fractions defined by their origin
- C10L2200/0469—Renewables or materials of biological origin
- C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
Definitions
- the invention relates to the use of copolymers of ⁇ -olefin, vinyl ester and ⁇ , ⁇ -unsaturated carboxylic acid ester, as additives improving cold resistance of fuels and lubricants as well as fuel oils and packages containing these copolymers.
- compositions of hydrocarbons notably based on middle distillate types containing paraffinic waxes, such as for example diesel fuels and heating oils, exhibit a significant decrease in their flow properties. It is well-known that the crystallization of paraffins is a limiting factor in the use of middle distillates. Also, it is important to prepare diesel fuels adapted to temperatures at which they will be used in motor vehicles, i.e. to the surrounding climate. Generally, cold operability of fuels at ⁇ 10° C. is sufficient in many hot or temperate countries. But in countries with a cold climate such as the Scandinavian countries, Canada and the countries of North Asia, temperatures of use of the fuels much lower than ⁇ 20° C. may be attained.
- paraffins are crystallized at the bottom of the tank, upon starting they may be driven into the fuel circuit and notably block the filters and pre-filters positioned upstream from the injection systems (pump and injectors). Also, when storing domestic oils, paraffins precipitate to the bottom of the tank and may be driven and obstruct the conduits upstream from the pump and from the supply system of the boiler (nozzle and filter). It is obvious that the presence of solids, such as paraffin crystals, prevents normal circulation of the middle distillate.
- EP 261 957 which are generally copolymers of ethylene and of an unsaturated ester, such as ethylene/vinyl acetate (EVA), ethylene/vinyl propionate (EVP), ethylene/vinyl ethanoate (EVE), ethylene/methyl methacrylate (EMMA), and ethylene/alkyl fumarate copolymers.
- EVA ethylene/vinyl acetate
- EVE ethylene/vinyl propionate
- EVE ethylene/vinyl ethanoate
- EMMA ethylene/methyl methacrylate
- alkyl fumarate copolymers such as ethylene/alkyl fumarate copolymers.
- the prior art also proposes mixtures of conventional CFI additives of the ethylene/unsaturated ester type with lubricants (mono- or poly-carboxylic acid esters of mono- or poly-alcohols (see for example EP 721 492), with anti-sedimentation agents (see for example FR 2 490 669), with ethers (see for example U.S. Pat. No. 3,999,960, EP 187 488).
- lubricants mono- or poly-carboxylic acid esters of mono- or poly-alcohols
- anti-sedimentation agents see for example FR 2 490 669
- ethers see for example U.S. Pat. No. 3,999,960, EP 187 488).
- CFI additives which are terpolymers or copolymers derived from more than 3 distinct monomers are also found.
- U.S. Pat. No. 6,509,424 describes a method for preparing terpolymers of ethylene and of at least two compounds containing ethylenic unsaturations, such as vinyl esters, (meth)acrylic esters, alkyl vinyl ethers, in a tubular reactor. These terpolymers may be used as additives improving cold flow of petroleums and petroleum distillates.
- 3,642,459 describes terpolymers comprising 40-89% by weight of ethylene, 10-40% by weight of vinyl ester derived from a short chain (C 2 -C 4 ) carboxylic acid, such as vinyl acetate, and unsaturated monoesters having a C 10 -C 22 alkyl chain; these terpolymers are used as additives for lowering the pour point of petroleum distillates and as anti-wax agents and for improving their filterability.
- U.S. Pat. No. 4,156,434 describes terpolymers of ethylene, vinyl acetate and of acrylic ester deriving from a C 12 -C 24 alcohol which lower the pour point of the fuels into which they are incorporated but nothing is said on the improvement of cold filterability of these additives.
- WO 2005/054314 describes terpolymers of ⁇ -olefin, vinyl ester and ⁇ , ⁇ -unsaturated mono carboxylic acid ester, which may be used.
- Terpolymers are exemplified, particularly preferred by the applicant, which contain more than 80% by moles of ethylene and less than 9% by moles of vinyl acetate.
- these terpolymers containing less than 9% by moles of vinyl acetate although having an effect on the decrease in LFT for middle distillates containing more than 18% of n-paraffins, are not satisfactory as regards solubility on the one hand and tendency to blocking (or room temperature filterability) on the other hand: damageable filter cloggings are reported.
- EP 1 391 498 describes additives improving low temperature fluidity of middle distillates, which are vinyl polymers (A), preferably ethylene-vinyl ester copolymers, for which the amount of hexane-insoluble materials exceeds 60% by weight at ⁇ 20° C. and is less than 30% by weight at 10° C.; the examples of EP 1 391 498 clearly show that the filterability temperature (cold filter plug point (CFPP)) is lowered for copolymers and terpolymers, for which the amount of hexane-insoluble material exceeds 60% by weight at ⁇ 20° C. and is less than 30% by weight at 10° C.
- CFPP cold filter plug point
- the exemplified copolymers are EVA copolymers and ethylene-(vinyl acetate)-(vinyl neodecanoate or 2-ethylhexanoate) terpolymers.
- the present invention relates to the use of copolymers as additives improving cold resistance of fuels (CFI additives); these copolymers contain units derived from at least one ⁇ -olefin, at least one vinyl ester and at least one ⁇ , ⁇ -unsaturated mono-carboxylic ester, and are preferably terpolymers of ethylene, of vinyl acetate and of ethyl-2-hexyl acrylate.
- the copolymers according to the invention which may be used as CFI additives comprise
- the copolymers which may be used as CFI additives are inscribed in a quadrilateral ABCD in which A, B, C and D represent the apices of said quadrilateral and correspond to the molar percentages of at least the vinyl ester and of at least the ⁇ , ⁇ -unsaturated mono-carboxylic acid ester:
- copolymers may be prepared in a known way by any polymerization method, (see for example, Ullmann's Encyclopedia of Industrial Chemistry, 5 th Edition, “Waxes”, Vol. A 28, p. 146; U.S. Pat. No. 3,627,838; EP 7 590) notably by radical polymerization, preferably under high pressure, typically of the order of 1,000 to 3,000 bars (100 to 300 MPa), preferably from 1,500 to 2,000 bars (150 to 200 MPa), the reaction temperatures generally ranging from 160 to 320° C., preferably from 200 to 280° C., and in the presence of at least one radical initiator generally selected from organic peroxides and/or oxygen- or nitrogen-containing compounds, and of a molecular weight regulator (aliphatic ketone or aldehyde, .
- a radical initiator generally selected from organic peroxides and/or oxygen- or nitrogen-containing compounds
- a molecular weight regulator aliphatic ketone or aldehyde, .
- the copolymers may for example be prepared in a tubular reactor according to the method described in U.S. Pat. No. 6,509,424.
- the compositions based on hydrocarbons into which the copolymers according to the invention are incorporated, are selected from all types of oils or fuels, such as diesel fuels, domestics oils for heating installations (DOF), kerosene, aviation fuels, heavy fuels, etc. . . . .
- the sulfur content of the hydrocarbon compositions is less than 5,000 ppm, preferably less than 500 ppm, and more preferentially less than 50 ppm, or even less than 10 ppm and advantageously without any sulfur.
- the compositions based on hydrocarbons comprise middle distillates with a boiling temperature comprised between 100 and 500° C.; their initial crystallization temperature Tcc is often greater than or equal to ⁇ 20° C., generally comprised between ⁇ 15° C. and +10° C.
- distillates may for example be selected from distillates obtained by direct distillation of crude hydrocarbons, distillates in vacuo, hydrotreated distillates, distillates from catalytic cracking and/or from hydrocracking of distillates in vacuo, distillates resulting from ARDS (atmospheric residue desulfurization) type conversion processes and/or viscoreduction processes, distillates from upgrading of Fischer Tropsch cuts, distillates resulting from BTL (biomass to liquid) conversion of plant and/or animal biomass, taken alone or as a combination, and/or esters of plant and animal oils or mixtures thereof.
- ARDS atmospheric residue desulfurization
- BTL biomass to liquid
- compositions of hydrocarbons may also contain distillates from more complex refining operations than those from direct distillation of hydrocarbons which may for example stem from cracking, hydrocracking and/or catalytic cracking processes and viscoreduction processes. They may also contain novel sources of distillates, among which mention may notably be made of:
- light middle distillates distillates for which the content in n-paraffins having 24 carbon atoms or more ranges from 0 to less than about 0.7% by weight of the total fuel composition; the C 18 -C 23 n-paraffins of which account for about 3 to about 5% of the total weight of the fuel and for which the mass ratio of C 18 -C 23 n-paraffins over the C 24 and higher paraffins generally ranges from 10 to 35.
- copolymers with Mw comprised between 5,000 and 10,000 and with Mn comprised between 1,500 and 8,000, preferably with Mw comprised between 5,000 and 8,000 and with Mn comprised between 1,500 and 5,000, are particularly effective when they are incorporated into heavy middle distillates and/or with a rather high initial crystallization temperature (which may typically range from 0 to 15° C.).
- heavy middle distillates distillates for which the content in n-paraffins with 24 carbon atoms or more ranges from about 0.7 to about 2% by weight of the total fuel composition; the C 18 -C 23 n-paraffins of which account for about 1 to about 10% of the total weight of the fuel and for which the mass ratio of C 18 -C 23 n-paraffins over C 24 + paraffins generally ranges from 1 to 10.
- the copolymers may be added as such in the compositions of hydrocarbons or preferentially as concentrated solutions, in particular solutions containing from 50 to 80%, preferably from 60 to 70% by weight of copolymer(s) in a solvent, such as aliphatic or aromatic hydrocarbons, either alone or as a mixture (naphtha, kerosene, hydrocarbon fractions such as Solvesso solvent, paraffinic hydrocarbons, such as pentane, hexane).
- a solvent such as aliphatic or aromatic hydrocarbons, either alone or as a mixture (naphtha, kerosene, hydrocarbon fractions such as Solvesso solvent, paraffinic hydrocarbons, such as pentane, hexane).
- the compositions of hydrocarbons comprise from 10 to 50,000 ppm by weight of at least one copolymer described above, optionally, preferably from 100 to 1,000 ppm and advantageously from 150 to 500 ppm.
- compositions of hydrocarbons may also contain one or more other additives different from the copolymers according to the invention, selected from detergents, anti-corrosion agents, dispersants, de-emulsifiers, antifoaming agents, biocides, reodorants, procetane additives, friction modifiers, lubricity additives or unctuousness additives, combustion aids (combustion and soot catalytic promoters), agents improving the cloud point, the pour point, the limiting filterability temperature, antisedimentation agents, antiwear agents and/or agents modifying conductivity.
- additives mention may particularly be made of:
- EVA and/or EVP copolymers are EVA and/or EVP copolymers.
- the improved cold resistance additives according to the invention may be added into the compositions of hydrocarbons inside the refinery, and/or be incorporated downstream from the refinery, optionally as a mixture with other additives, as a package or packet of additives.
- terpolymers of ethylene, vinyl acetate and ethyl-2 hexyl acrylate are synthesized by radical polymerization under high pressure (1,400 to 2,500 bars (140 to 250 MPa) and at a polymerization temperature from 200 to 280° C.
- the synthesis is carried out by using an aliphatic aldehyde (propanal) in order to control the molecular masses and by using peroxides as polymerization initiators.
- Mn and Mw of the synthesized terpolymers are indicated the Mn and Mw of the synthesized terpolymers as well as their percentages of monomers.
- the cold resistance LFT efficiency of the terpolymers incorporated in GOM 1 and GOM 2 is measured at the concentration of 210 ppm; the results are grouped in Table 4.
- the terpolymer 17 according to the invention is the most efficient on the gasoil GOM 1. Moreover, from the results obtained in Table 3, it is seen that the terpolymer 17 added in an amount of 400 ppm in GOM 1 does not degrade the blocking tendency. This is not the case of the comparative terpolymers 6; 7; 16 and 18 according to WO 2005/054314, which strongly degrade the blocking tendency measured according to IP 387 and are not as LFT-efficient as the additive 17 of the invention.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0903278 | 2009-07-03 | ||
FR0903278A FR2947558B1 (fr) | 2009-07-03 | 2009-07-03 | Terpolymere et ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles |
PCT/IB2010/052922 WO2011001352A1 (fr) | 2009-07-03 | 2010-06-25 | Terpolymere ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles |
Publications (1)
Publication Number | Publication Date |
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US20120102825A1 true US20120102825A1 (en) | 2012-05-03 |
Family
ID=41716191
Family Applications (1)
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US13/381,554 Abandoned US20120102825A1 (en) | 2009-07-03 | 2010-06-25 | Ethylene/vinyl acetate/unsaturated esters terpolymer as an additive for improving the resistance to cold of liquid hydrocarbons such as middle distillates and fuels |
Country Status (19)
Country | Link |
---|---|
US (1) | US20120102825A1 (fr) |
EP (1) | EP2449063B2 (fr) |
JP (1) | JP2012532225A (fr) |
KR (1) | KR102002887B1 (fr) |
CN (1) | CN102549120A (fr) |
AR (1) | AR077631A1 (fr) |
AU (1) | AU2010267626B2 (fr) |
BR (1) | BRPI1016080B1 (fr) |
CA (1) | CA2765245C (fr) |
CL (1) | CL2011003342A1 (fr) |
EA (1) | EA201270129A1 (fr) |
ES (1) | ES2706903T5 (fr) |
FR (1) | FR2947558B1 (fr) |
MX (1) | MX363328B (fr) |
PT (1) | PT2449063T (fr) |
SG (1) | SG177381A1 (fr) |
TW (1) | TWI496883B (fr) |
WO (1) | WO2011001352A1 (fr) |
ZA (1) | ZA201109307B (fr) |
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US20140033605A1 (en) * | 2011-03-25 | 2014-02-06 | Evonik Oil Additives Gmbh | Composition to improve oxidation stability of fuel oils |
US20170009067A1 (en) * | 2014-02-18 | 2017-01-12 | Basf Se | Copolymers comprising ethylene, vinyl esters and esters of (meth)acrylic acid, their formulations and use as pour point depressant, wax inhibitor and flow enhancer for crude oils |
US9587193B2 (en) | 2012-02-17 | 2017-03-07 | Total Marketing Services | Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels |
US20170145335A1 (en) * | 2003-12-04 | 2017-05-25 | Basf Se | Fuel oil compositions with improved cold flow properties |
US9663736B2 (en) | 2013-04-25 | 2017-05-30 | Total Marketing Services | Additive for improving the oxidation and/or storage stability of motor fuels or liquid hydrocarbon-containing fuels |
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FR2925916B1 (fr) * | 2007-12-28 | 2010-11-12 | Total France | Terpolymere ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles |
TWI576384B (zh) * | 2014-11-25 | 2017-04-01 | 鴻明環保科技股份有限公司 | 高植物源含量之乙烯-醋酸乙烯共聚物混合物發泡材料、其製造方法及應用 |
CN105733712B (zh) * | 2014-12-08 | 2017-12-05 | 中国石油天然气股份有限公司 | 用于航空生物燃料的润滑减磨添加剂 |
FR3113063B1 (fr) | 2020-07-31 | 2022-08-12 | Total Marketing Services | Utilisation de copolymères à distribution de masse molaire spécifique pour abaisser la température limite de filtrabilité de carburants ou de combustibles |
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-
2009
- 2009-07-03 FR FR0903278A patent/FR2947558B1/fr active Active
-
2010
- 2010-06-25 US US13/381,554 patent/US20120102825A1/en not_active Abandoned
- 2010-06-25 SG SG2011096435A patent/SG177381A1/en unknown
- 2010-06-25 EP EP10734559.7A patent/EP2449063B2/fr active Active
- 2010-06-25 JP JP2012518141A patent/JP2012532225A/ja active Pending
- 2010-06-25 ES ES10734559T patent/ES2706903T5/es active Active
- 2010-06-25 CN CN2010800296922A patent/CN102549120A/zh active Pending
- 2010-06-25 MX MX2012000172A patent/MX363328B/es unknown
- 2010-06-25 BR BRPI1016080A patent/BRPI1016080B1/pt active IP Right Grant
- 2010-06-25 AU AU2010267626A patent/AU2010267626B2/en active Active
- 2010-06-25 CA CA2765245A patent/CA2765245C/fr active Active
- 2010-06-25 EA EA201270129A patent/EA201270129A1/ru unknown
- 2010-06-25 PT PT10734559T patent/PT2449063T/pt unknown
- 2010-06-25 WO PCT/IB2010/052922 patent/WO2011001352A1/fr active Application Filing
- 2010-06-25 KR KR1020117031259A patent/KR102002887B1/ko active IP Right Grant
- 2010-06-29 TW TW099121257A patent/TWI496883B/zh not_active IP Right Cessation
- 2010-07-01 AR ARP100102360A patent/AR077631A1/es not_active Application Discontinuation
-
2011
- 2011-12-19 ZA ZA2011/09307A patent/ZA201109307B/en unknown
- 2011-12-29 CL CL2011003342A patent/CL2011003342A1/es unknown
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US20070094920A1 (en) * | 2004-12-03 | 2007-05-03 | Basf Aktiengesellschaft | Fuel oil compositions with improved cold flow properties |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20170145335A1 (en) * | 2003-12-04 | 2017-05-25 | Basf Se | Fuel oil compositions with improved cold flow properties |
US10047314B2 (en) * | 2003-12-04 | 2018-08-14 | Basf Se | Fuel oil compositions with improved cold flow properties |
US20140033605A1 (en) * | 2011-03-25 | 2014-02-06 | Evonik Oil Additives Gmbh | Composition to improve oxidation stability of fuel oils |
US9284505B2 (en) * | 2011-03-25 | 2016-03-15 | Evonik Oil Additives Gmbh | Composition to improve oxidation stability of fuel oils |
US9587193B2 (en) | 2012-02-17 | 2017-03-07 | Total Marketing Services | Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels |
US9663736B2 (en) | 2013-04-25 | 2017-05-30 | Total Marketing Services | Additive for improving the oxidation and/or storage stability of motor fuels or liquid hydrocarbon-containing fuels |
US20170009067A1 (en) * | 2014-02-18 | 2017-01-12 | Basf Se | Copolymers comprising ethylene, vinyl esters and esters of (meth)acrylic acid, their formulations and use as pour point depressant, wax inhibitor and flow enhancer for crude oils |
US10208192B2 (en) * | 2014-02-18 | 2019-02-19 | Basf Se | Copolymers comprising ethylene, vinyl esters and esters of (meth)acrylic acid, their formulations and use as pour point depressant, wax inhibitor and flow enhancer for crude oils |
US20190136023A1 (en) * | 2014-02-18 | 2019-05-09 | Basf Se | Copolymers comprising ethylene vinyl esters and esters of (meth)acrylic acid, their formulations and use as pour point depressant, wax inhibitor and flow enhancer for crude oils |
US10619038B2 (en) * | 2014-02-18 | 2020-04-14 | Basf Se | Copolymers comprising ethylene vinyl esters and esters of (meth)acrylic acid, their formulations and use as pour point depressant, wax inhibitor and flow enhancer for crude oils |
Also Published As
Publication number | Publication date |
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EA201270129A1 (ru) | 2012-05-30 |
PT2449063T (pt) | 2019-02-04 |
ES2706903T5 (es) | 2021-12-14 |
ES2706903T3 (es) | 2019-04-01 |
JP2012532225A (ja) | 2012-12-13 |
EP2449063B1 (fr) | 2018-11-21 |
CA2765245C (fr) | 2017-07-25 |
AU2010267626A1 (en) | 2012-02-02 |
SG177381A1 (en) | 2012-02-28 |
TW201116617A (en) | 2011-05-16 |
MX363328B (es) | 2019-03-20 |
WO2011001352A1 (fr) | 2011-01-06 |
CA2765245A1 (fr) | 2011-01-06 |
TWI496883B (zh) | 2015-08-21 |
AU2010267626B2 (en) | 2016-05-12 |
CL2011003342A1 (es) | 2012-07-06 |
KR20120040161A (ko) | 2012-04-26 |
CN102549120A (zh) | 2012-07-04 |
EP2449063A1 (fr) | 2012-05-09 |
FR2947558A1 (fr) | 2011-01-07 |
ZA201109307B (en) | 2012-09-26 |
MX2012000172A (es) | 2012-02-28 |
BRPI1016080B1 (pt) | 2018-10-16 |
EP2449063B2 (fr) | 2021-07-28 |
BRPI1016080A2 (pt) | 2016-05-10 |
AR077631A1 (es) | 2011-09-14 |
KR102002887B1 (ko) | 2019-07-23 |
FR2947558B1 (fr) | 2011-08-19 |
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