EP1526167A2 - Kaltfliessverbesserer für Brennstofföle pflanzlichen oder tierischen Ursprungs - Google Patents
Kaltfliessverbesserer für Brennstofföle pflanzlichen oder tierischen Ursprungs Download PDFInfo
- Publication number
- EP1526167A2 EP1526167A2 EP04024234A EP04024234A EP1526167A2 EP 1526167 A2 EP1526167 A2 EP 1526167A2 EP 04024234 A EP04024234 A EP 04024234A EP 04024234 A EP04024234 A EP 04024234A EP 1526167 A2 EP1526167 A2 EP 1526167A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- additive according
- monomer
- mol
- acid
- fuel oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000295 fuel oil Substances 0.000 title claims abstract description 25
- 241001465754 Metazoa Species 0.000 title claims abstract description 18
- 235000013311 vegetables Nutrition 0.000 title claims abstract description 14
- 239000000654 additive Substances 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 47
- 229920001577 copolymer Polymers 0.000 claims abstract description 45
- 230000000996 additive effect Effects 0.000 claims abstract description 34
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- 150000001336 alkenes Chemical class 0.000 claims abstract description 21
- 239000005977 Ethylene Substances 0.000 claims abstract description 18
- 150000001408 amides Chemical group 0.000 claims abstract description 18
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 150000003949 imides Chemical class 0.000 claims abstract description 12
- 125000005462 imide group Chemical group 0.000 claims abstract description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 21
- 239000004711 α-olefin Substances 0.000 claims description 18
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 16
- 239000012188 paraffin wax Substances 0.000 claims description 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
- TVFJAZCVMOXQRK-UHFFFAOYSA-N ethenyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OC=C TVFJAZCVMOXQRK-UHFFFAOYSA-N 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 3
- WBZPMFHFKXZDRZ-UHFFFAOYSA-N ethenyl 6,6-dimethylheptanoate Chemical compound CC(C)(C)CCCCC(=O)OC=C WBZPMFHFKXZDRZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 2
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 2
- RAJLHYZMTYVILB-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]propanal Chemical compound FC(F)(F)C1=CC=C(CCC=O)C=C1 RAJLHYZMTYVILB-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 abstract description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 49
- 235000019198 oils Nutrition 0.000 description 49
- -1 aliphatic radical Chemical group 0.000 description 34
- 235000014113 dietary fatty acids Nutrition 0.000 description 24
- 229930195729 fatty acid Natural products 0.000 description 24
- 239000000194 fatty acid Substances 0.000 description 24
- 150000004665 fatty acids Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229920001897 terpolymer Polymers 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920001038 ethylene copolymer Polymers 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 235000019484 Rapeseed oil Nutrition 0.000 description 10
- 239000002551 biofuel Substances 0.000 description 10
- 239000002270 dispersing agent Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 9
- 150000004702 methyl esters Chemical class 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- 235000019486 Sunflower oil Nutrition 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000005907 alkyl ester group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002600 sunflower oil Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 239000003225 biodiesel Substances 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000003222 Helianthus annuus Nutrition 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000012662 bulk polymerization Methods 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000005038 ethylene vinyl acetate Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 241000208818 Helianthus Species 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 235000012343 cottonseed oil Nutrition 0.000 description 3
- 239000002385 cottonseed oil Substances 0.000 description 3
- 230000000994 depressogenic effect Effects 0.000 description 3
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
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- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 2
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- 244000020551 Helianthus annuus Species 0.000 description 2
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- 239000004165 Methyl ester of fatty acids Substances 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 239000002283 diesel fuel Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
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- 230000007704 transition Effects 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N tridecaene Natural products CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
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- 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
-
- 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
- C10L1/1955—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds 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 an alcohol, ether, aldehyde, ketonic, ketal, acetal radical
-
- 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
- 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
- C10L1/197—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
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
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- 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
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- 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
- C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
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- 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
- the present invention relates to an additive, its use as Cold flow improver for vegetable or animal fuel oils and accordingly additized fuel oils.
- renewable raw materials include, in particular, natural oils and fats of plant or animal origin. These are typically triglycerides of fatty acids with 10 to 24 C atoms, which have a calorific value comparable to conventional fuels, but at the same time are considered less harmful to the environment.
- Biofuels ie fuels derived from animal or plant material, are obtained from renewable sources and thus produce only as much CO 2 as was previously converted into biomass. It has been reported that combustion produces less carbon dioxide than equivalent amount of petroleum distillate fuel, eg, diesel fuel, and that very little sulfur dioxide is produced. In addition, they are biodegradable.
- Oils obtained from animal or vegetable material are mainly metabolites comprising triglycerides of monocarboxylic acids, eg acids having 10 to 25 carbon atoms, and the formula in which R is an aliphatic radical of 10 to 25 carbon atoms, which may be saturated or unsaturated.
- oils contain glycerides of a number of acids whose Number and variety varies with the source of the oil, and they may additionally Contain phosphoglycerides.
- Such oils can be used in the prior art known methods are obtained.
- Triglycerides Due to the partially unsatisfactory physical properties of the Triglycerides, the technique has gone over to the naturally occurring Triglycerides in fatty acid esters of lower alcohols such as methanol or ethanol convict.
- EP-B-0 665 873 discloses a fuel oil composition
- a fuel oil composition comprising a A biofuel comprising a petroleum-based fuel oil and an additive which comprises (a) an oil-soluble ethylene copolymer or (b) a comb polymer or (c) a polar Nitrogen compound or (d) a compound in which at least one in the Substantially linear alkyl group having 10 to 30 carbon atoms with one not polymeric organic radical is connected to at least one linear chain of To provide atoms containing the carbon atoms of the alkyl groups and one or more includes non-terminal oxygen atoms, or (e) one or more of Components (a), (b), (c) and (d).
- EP-B-0 153 176 discloses the use of polymers based on unsaturated C 4 -C 8 dicarboxylic acid di-alkyl esters having average alkyl chain lengths of 12 to 14 as cold flow improvers for certain petroleum distillate fuel oils.
- Suitable comonomers are unsaturated esters, in particular vinyl acetate, but also ⁇ -olefins.
- WO 95/22300 discloses comb polymers in which the alkyl radicals have on average less than 12 C atoms. These additives are especially suitable for oils with cloud points of less than -10 ° C, where it is oils may also be native hydrocarbon oils (page 21, Line 16 ff.). However, native oils have cloud points from about -2 ° C upwards.
- Another object of the invention is a fuel oil composition, containing a fuel oil of animal or vegetable origin and the above defined additive.
- Another object of the invention is the use of the above defined Additive to improve the cold flow properties of animal fuel oil or of vegetable origin.
- Another object of the invention is a method for improving the Cold flow properties of fuel oils of animal or vegetable origin, by giving fuel oils of animal or vegetable origin the above Adds defined additive.
- Q has values from 24 to 26.
- Under side chain length of olefins here is the outgoing from the polymer backbone Understood alkyl radical, ie the chain length of the monomeric olefin minus the both olefinically bound C atoms.
- Understood alkyl radical ie the chain length of the monomeric olefin minus the both olefinically bound C atoms.
- Olefins with vinylidene grouping is the corresponding Total chain length of the olefin minus the transition into the polymer backbone To consider double bond.
- Suitable ethylene copolymers A) are those which contain from 8 to 21 mol% of one or more a plurality of vinyl and / or (meth) acrylic esters and 79 to 92 wt .-% ethylene. Particularly preferred are ethylene copolymers with 10 to 18 mol% and especially 12 to 16 mol% of at least one vinyl ester.
- Suitable vinyl esters are derived from Fatty acids with linear or branched alkyl groups having 1 to 18 C atoms and preferably from 1 to 12 carbon atoms.
- Examples include vinyl acetate, Vinyl propionate, vinyl butyrate, vinyl hexanoate, vinyl heptanoate, vinyl octanoate, Vinyl laurate and vinyl stearate and branched fatty acid based esters of Vinyl alcohol such as vinyl isobutyrate, vinyl pivalate, vinyl 2-ethylhexanoate, iso-nonanoic acid vinyl ester, Vinyl neononanoate, vinyl neodecanoate and Neoundecanklavinylester. Particularly preferred is vinyl acetate.
- esters of acrylic and methacrylic acid having 1 to 20 carbon atoms in the alkyl radical such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n- and iso-butyl (meth) acrylate, hexyl, octyl, 2-ethylhexyl, decyl, dodecyl, tetradecyl, Hexadecyl, octadecyl (meth) acrylate and mixtures of two, three, four or also several of these comonomers.
- Particularly preferred terpolymers of 2-Ethylhexankladlesters, the Neononanoic or vinyl neodecanoate contain except Ethylene preferably 3.5 to 20 mol%, in particular 8 to 15 mol% of vinyl acetate and 0.1 to 12 mol%, in particular 0.2 to 5 mol% of at least one long-chain Vinylester, wherein the total comonomer content between 8 and 21 mol%, preferably between 12 and 18 mol%.
- copolymers contain, in addition to ethylene and 8 to 18 mol% vinyl esters, 0.5 to 10 mol% Olefins such as propene, butene, isobutylene, hexene, 4-methylpentene, octene, diisobutylene and / or norbornene.
- Olefins such as propene, butene, isobutylene, hexene, 4-methylpentene, octene, diisobutylene and / or norbornene.
- the copolymers A preferably have molecular weights which correspond to melt viscosities at 140 ° C. of from 20 to 10,000 mPas, in particular from 30 to 5,000 mPas and especially from 50 to 1,000 mPas.
- the determined by 1 H NMR spectroscopy degrees of branching are preferably between 1 and 9 CH 3/100 CH 2 groups, especially between 2 and 6 CH 3/100 CH 2 groups, such as 2.5 to 5 CH 3/100 CH 2 groups not derived from the comonomers.
- the copolymers (A) are prepared by the usual copolymerization methods such as for example suspension polymerization, solvent polymerization, Gas phase polymerization or high-pressure mass polymerization produced. Preference is given to high pressure bulk polymerization at pressures of 50 to 400 MPa, preferably 100 to 300 MPa and temperatures of 100 to 300 ° C, preferably 150 to 220 ° C performed. In a particularly preferred production variant the polymerization takes place in a multizone reactor, wherein the Temperature difference between the Peroxiddostechniken along the tube reactor is kept as low as possible, i. ⁇ 50 ° C, preferably ⁇ 30 ° C, in particular ⁇ 15 ° C. Preferably, the temperature maxima differ in the individual reaction zones less than 30 ° C, more preferably less than 20 ° C and especially around less than 10 ° C.
- the reaction of the monomers is by free-radical initiators (Radical chain starter) initiated.
- This class of substance includes e.g. Oxygen, Hydroperoxides, peroxides and azo compounds such as cumene hydroperoxide, t-butyl hydroperoxide, dilauroyl peroxide, dibenzoyl peroxide, bis (2-ethylhexyl) peroxide carbonate, t-butyl perpivalate, t-butyl per-maleate, t-butyl perbenzoate, dicumyl peroxide, t-butyl cumyl peroxide, di- (t-butyl) peroxide, 2,2'-azobis (2-methylpropanonitrile), 2,2'-azobis (2-methylbutyronitrile).
- the initiators are used individually or as a mixture of two or more substances in amounts of 0.01 to 20 wt .-%, preferably 0.05 to 10 wt .-
- High pressure bulk polymerization is used in known high pressure reactors, e.g. Autoclaves or tube reactors, discontinuous or continuous, Tube reactors have proven particularly useful.
- Solvents such as aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures, benzene or toluene, may be included in the reaction mixture.
- the polymerization is the mixture of the monomers, the initiator and, if used, the moderator, a tubular reactor via the reactor inlet and above supplied to one or more side branches.
- Preferred moderators are for example, hydrogen, saturated and unsaturated hydrocarbons such as for example, propane or propene, aldehydes such as propionaldehyde, n-butyraldehyde or iso-butyraldehyde, ketones such as acetone, Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and alcohols such for example, butanol.
- the comonomers as well as the moderators can do it both together with ethylene and separated via side streams in the reactor be dosed.
- the monomer streams can be different be composed (EP-A-0 271 738 and EP-A-0 922 716).
- the mixtures differ based on the mixtures lying polymers in at least one characteristic.
- the Mixing ratio of the different ethylene copolymers is preferred between 20: 1 and 1:20, preferably 10: 1 to 1:10, in particular 5: 1 to 1: 5.
- the copolymers B are preferably derived from ethylenically unsaturated Dicarboxylic acids and their derivatives such as esters and anhydrides. Preferred are Maleic acid, fumaric acid, itaconic acid and their esters with lower alcohols with 1 to 6 carbon atoms and their anhydrides such as maleic anhydride.
- Comonomers are monoolefins with 10 to 20, in particular with 12 to 18 C-atoms particularly suitable. These are preferably linear and the double bond is preferably terminal such as dodecene, tridecene, tetradecene, Pentadecene, hexadecene, heptadecene and octadecene.
- the ratio of Dicarboxylic acid or dicarboxylic acid derivative to olefin or olefins in the polymer preferably in the range 1: 1.5 to 1.5: 1, especially it is equimolar.
- copolymer B which are copolymerizable with ethylenically unsaturated dicarboxylic acids and the olefins mentioned, such as, for example, and longer-chain olefins, allyl polyglycol ethers, C 1 -C 30 -alkyl (meth) acrylates, vinylaromatics or C 1 -C 20 -alkyl vinyl ethers.
- the preparation of the copolymers B) according to the invention is preferably carried out at Temperatures between 50 and 220 ° C, in particular 100 to 190 ° C, especially 130 to 170 ° C.
- the preferred manufacturing process is the solvent-free Bulk polymerization, but it is also possible, the polymerization in the presence aprotic solvents such as benzene, toluene, xylene or higher-boiling aromatic, aliphatic or isoaliphatic solvents or Solvent mixtures such as kerosene or solvent naphtha perform.
- aprotic solvents such as benzene, toluene, xylene or higher-boiling aromatic, aliphatic or isoaliphatic solvents or Solvent mixtures such as kerosene or solvent naphtha perform.
- Especially the polymerization is preferably in moderately moderating, aliphatic or isoaliphatic solvents.
- the solvent content in the polymerization mixture is
- the average molecular weight of the copolymers B according to the invention is in the general between 1,200 and 200,000 g / mol, in particular between 2,000 and 100,000 g / mol, measured by gel permeation chromatography (GPC) against Polystyrene standards in THF.
- GPC gel permeation chromatography
- Inventive copolymers B must be in practice-relevant Dosiermengen be oil-soluble, that is, they must be in the zu dissolve additivating oil at 50 ° C residue-free.
- the reaction of the monomers is by free-radical initiators (Radical chain starter) initiated.
- This class of substance includes e.g. Oxygen, Hydroperoxides and peroxides such as e.g. Cumene hydroperoxide, t-butyl hydroperoxide, Dilauroyl peroxide, dibenzoyl peroxide, bis (2-ethylhexyl) peroxide carbonate, t-butyl perpivalate, t-butyl per-maleate, t-butyl perbenzoate, dicumyl peroxide, t-butyl cumyl peroxide, di- (t-butyl) peroxide, and azo compounds such as e.g.
- the initiators be used individually or as a mixture of two or more substances in quantities of 0.01 to 20 wt .-%, preferably 0.05 to 10 wt .-%, based on the Monomer mixture used.
- the copolymers can be prepared either by reaction of maleic, fumaric and / or Itaconic acid or its derivatives with the corresponding amine and subsequent Copolymerization or by copolymerization of olefin or olefins with at least one unsaturated dicarboxylic acid or its derivative such as for example, itaconic and / or maleic anhydride and subsequent reaction be prepared with amines. Preference is given to copolymerization with Anhydrides performed and the resulting copolymer after preparation in converted an amide and / or an imide.
- reaction with amines takes place in both cases, for example by reaction with 0.8 to 2.5 moles of amine per mole of anhydride, preferably with 1.0 to 2.0 moles of amine per mol anhydride at 50 to 300 ° C.
- 0.8 to 2.5 moles of amine per mole of anhydride preferably with 1.0 to 2.0 moles of amine per mol anhydride at 50 to 300 ° C.
- reaction temperatures of about 50 to 100 ° C preferably hemi-amides, which additionally carry one carboxyl group per amide group.
- Reaction temperatures of about 100 to 250 ° C arise from primary amines below Dehydration prefers imides.
- Suitable amines are primary and secondary amines having one or two C 8 -C 16 alkyl radicals. They can carry one, two or three amino groups which are linked via alkylene radicals having two or three carbon atoms. Preference is given to monoamines. In particular, they carry linear alkyl radicals, but they can also minor amounts, eg. B. up to 30 wt .-%, preferably up to 20 wt .-% and especially up to 10 wt .-% (in 1- or 2-position) contain branched amines. Shorter as well as longer-chain amines can be used, but their proportion is preferably less than 20 mol% and especially less than 10 mol%, for example between 1 and 5 mol%, based on the total amount of amines used.
- primary amines are octylamine, 2-ethylhexylamine, Decylamine, undecylamine, dodecylamine, n-tridecylamine, iso-tridecylamine, Tetradecylamine, pentadecylamine, hexadecylamine and mixtures thereof.
- Preferred secondary amines are dioctylamine, dinonylamine, didecylamine, didodecylamine, ditetradecylamine, dihexadecylamine, and amines having different alkyl chain lengths such as N-octyl-N-decylamine, N-decyl-N-dodecylamine, N-decyl-N-tetradecylamine, N-decyl N-hexadecylamine, N-dodecyl-N-tetradecylamine, N-dodecyl-N-hexadecylamine, N-tetradecyl-N-hexadecylamine.
- Secondary amines which, in addition to a C 8 -C 16 -alkyl radical, bear shorter side chains having 1 to 5 C atoms, for example methyl or ethyl groups, are suitable according to the invention.
- the alkyl chain length n is taken into account as the mean value of the alkyl chain lengths of C 8 to C 16 for the calculation of the Q factor. Shorter and longer alkyl radicals, if present, are not included in the calculation because they do not contribute to the effectiveness of the additives.
- Particularly preferred copolymers B are hemiamides and imides primary Monoamines.
- the additives may also contain polymers and copolymers based on C 10 -C 24 -alkyl acrylates or methacrylates (component C).
- These poly (alkyl acrylates) and methacrylates have molecular weights of 800 to 1,000,000 g / mol, and are preferably derived from caprylic, capric, undecyl, lauryl, myristyl, cetyl, palmitoleyl, stearyl alcohol or the like Mixtures such as coconut, palm, tallow or behenyl from.
- mixtures of the invention Copolymers B are used, provided that the mean of the Q values of the Mixture components again have values from 23 to 27 and preferably values of 24 to 26.
- the mixing ratio of the additives A and B according to the invention is (in Parts by weight) 20: 1 to 1:20, preferably 10: 1 to 1:10, in particular 5: 1 to 1: 2.
- the proportion of component C in the formulations of A, B and C can be up to 40 wt .-% amount; it is preferably less than 20% by weight, in particular between 1 and 10% by weight.
- the additives according to the invention are oils in amounts of from 0.001 to 5% by weight, preferably 0.005 to 1 wt .-% and especially added 0.01 to 0.5 wt .-%. there they may be dissolved as such or dissolved in solvents, e.g. aliphatic and / or aromatic hydrocarbons or Hydrocarbon mixtures such.
- they are based on fuel oil of animal or vegetable origin dissolved by fatty acid alkyl esters.
- the inventive Additives 1 - 80%, especially 10 - 70%, in particular 25 - 60% solvents.
- the fuel oil is the often referred to as "biodiesel” or “biofuel” to Fatty acid alkyl esters of fatty acids having 12 to 24 carbon atoms and alcohols having 1 to 4 C-atoms. Usually a major part of the fatty acids contains one, two or three Double bonds.
- oils derived from animal or vegetable material examples include rapeseed oil, Coriander oil, soybean oil, cottonseed oil, sunflower oil, castor oil, olive oil, Peanut oil, corn oil, almond oil, palm kernel oil, coconut oil, mustard seed oil, beef tallow, Bone oil, fish oils and used cooking oils.
- the fatty acid alkyl esters also referred to as biodiesel
- biodiesel can be made from these oils be derived by methods known in the art.
- Rapeseed oil that is a mixture of glycerol partially esterified fatty acids, is preferred because it is available in large quantities and in a simple manner by pressing out of Rapeseed is available.
- the also widely used oils of Sunflowers and soybeans and their mixtures with rapeseed oil preferred.
- Particularly suitable as biofuels are lower alkyl esters of fatty acids.
- commercial mixtures of ethyl, propyl, butyl and in particular methyl esters of fatty acids having 14 to 22 carbon atoms for example, lauric acid, myristic acid, palmitic acid, palmitoleic acid, Stearic acid, oleic acid, elaidic acid, petroselinic acid, ricinoleic acid, Elaeostearic acid, linoleic acid, linolenic acid, eicosanoic acid, gadoleic acid, Docosanic acid or erucic acid, preferably having an iodine value of 50 to 150, especially 90 to 125 have.
- Mixtures with particularly advantageous Properties are those that are mainly, i. H. at least 50% by weight, Methyl esters of fatty acids having 16 to 22 carbon atoms and 1, 2 or 3 Double bonds included.
- the preferred lower alkyl esters of fatty acids are the methyl esters of oleic acid, linoleic acid, linolenic acid and erucic acid.
- a biofuel is an oil derived from vegetable or animal material or is obtained or a derivative thereof, which as fuel and especially as diesel or heating oil can be used.
- oils can be used as biofuels are vegetable oil derivatives with particularly preferred biofuels alkyl ester derivatives of rapeseed oil, Cottonseed oil, soybean oil, sunflower oil, olive oil or palm oil are, being Rapsölchuremethylester, sunflower oil and Sojaölchuremethylester are very particularly preferred.
- biofuel or as a component in biofuel are also Altfettester such as Altfettmethylester.
- the additive may be added to the oil to be treated according to art known in the art Procedures are introduced. If more than one additive component or Coadditive component should be used, such components be introduced together or separately in any combination in the oil.
- the CFPP value of biodiesel can be determined Set values below -20 ° C and sometimes to values below -25 ° C, as they do be required for marketing for use especially in winter. Of the same is the pour point of biodiesel by the addition of the invention Additives are minimized.
- the additives of the invention are particularly advantageous in problematic oils containing a high proportion of esters of saturated fatty acids of more than 4% in particular more than 5% and especially with 7 to 25% like For example, with 8 to 20%, as for example in oils from sunflowers and Soy included. Such oils are characterized by cloud points of over -5 ° C and especially above -3 ° C.
- the additives according to the invention also together with one or more oil-soluble Co-additives are used, which already by themselves the cold flow properties of crude oils, lubricating oils or fuel oils.
- oil-soluble Co-additives are polar compounds that cause paraffin dispersion (Paraffin dispersants) and oil-soluble amphiphiles, with the proviso that they themselves differ from the comb polymers B.
- the additives according to the invention can be mixed with paraffin dispersants be used.
- Paraffin dispersants reduce the size of the paraffin crystals and cause the paraffin particles do not settle, but colloid with significantly reduced tendency to sediment, remain dispersed.
- Paraffin dispersants have both low molecular weight and polymeric, oil-soluble compounds having ionic or polar groups, e.g. amine salts and / or amides proven.
- Particularly preferred paraffin dispersants contain Reaction products of secondary fatty amines having 20 to 44 carbon atoms, in particular Dicocosamine, ditallow fatty amine, distearylamine and dibehenylamine with carboxylic acids and their derivatives.
- Paraffin dispersants which have proven particularly suitable are by reaction of aliphatic or aromatic amines, preferably long-chain aliphatic amines, with aliphatic or aromatic mono-, di-, tri- or Tetracarboxylic acids or their anhydrides are obtained (see US 4 211 534). Of are amides and ammonium salts of aminoalkylenepolycarboxylic such as Nitrilotriacetic acid or ethylenediaminetetraacetic acid with secondary amines as Paraffin dispersants are suitable (compare EP 0 398 101).
- paraffin dispersants are copolymers of maleic anhydride and ⁇ , ⁇ -unsaturated compounds, optionally with primary monoalkylamines and / or aliphatic alcohols can be implemented (see EP 0 154 177) and the reaction products of Alkenylspirobislactones with amines (see EP 0 413 279 B1) and after EP-A-0 606 055 A2 Reaction products of terpolymers based on ⁇ , ⁇ -unsaturated dicarboxylic anhydrides, ⁇ , ⁇ -unsaturated compounds and Polyoxyalkylene ethers of lower unsaturated alcohols.
- Paraffin dispersants are 1:10 to 20: 1, preferably 1: 1 to 10: 1.
- the additives can be used alone or together with other additives be, e.g. with other pour point depressants or dewaxing aids, with Antioxidants, cetane improvers, dehazers, demulsifiers, detergents, Dispersants, defoamers, dyes, corrosion inhibitors, Conductivity improvers, sludge inhibitors, odorants and / or additives to Humiliation of the cloud point.
- other pour point depressants or dewaxing aids with Antioxidants, cetane improvers, dehazers, demulsifiers, detergents, Dispersants, defoamers, dyes, corrosion inhibitors, Conductivity improvers, sludge inhibitors, odorants and / or additives to Humiliation of the cloud point.
- the CFPP value is determined in accordance with EN 116 and the determination of the cloud point in accordance with ISO 3015. Characterization of the used test oils Oil no. CP CFPP E 1 Rapsölklaremethylester -2.3 -14 ° C E 2 80% rapeseed oil methyl ester + 20% sunflower oil methyl ester -1.6 -10 ° C E 3 90% rapeseed oil methyl ester + 10% of soybean oil methyl ester -2.0 -8 ° C C chain distribution of the fatty acid methyl esters used for the preparation of the test oils (main constituents, FI .-% according to GC): C 16 C 16 ' C 18 C 18 ' C 18 " C 18 "' C 20 C 20 ' C 22 ⁇ saturated RME 4.4 0.4 1.6 57.8 21.6 8.8 1.5 0.7 0.2 7.7 SBME 6.0 0.1 3.8 28.7 58.7 0.1 0.3 0.3 0.7 10.8 SojaME 10.4 0.1 4.1 24.8 51.3 6.9 0.5
- the ethylene copolymers used are commercial products having the characteristics given in Table 2. The products were used as 65% and 50% (A3) settings in kerosene, respectively. Characterization of the ethylene copolymers used example Comonomer (s) V140 CH 3 / 100CH 2 A1 13.6 mole% vinyl acetate 130 mPas 3.7 A2 13.7 mole percent vinyl acetate and 1.4 mole percent vinyl neodecanoate 105 mPas 5.3 A3 9.4 mol% vinyl acetate 220 mPas 6.2 A4 Mixture of EVA copolymer with 16 mol% vinyl acetate and EVA with 95 mPas 3.2 5 mol% vinyl acetate in the ratio 13: 1 350 mPas 5.7
- the polymerization of maleic anhydride (MSA) with ⁇ -olefins takes place in one higher boiling aromatic hydrocarbon mixture at 160 ° C in the presence a mixture of equal parts of tert-butyl peroxybenzoate and tert-butyl peroxy-2-ethylhexanoate as a radical chain starter.
- Table 3 shows various examples Copolymers and the molar fractions used for their preparation Monomers and chain length (R) and molar amount (relative to MSA) of the Derivatization of amine used and the factor Q calculated therefrom.
- the amines used are, unless otherwise stated, to monoalkylamines.
- the reactions with amines are carried out in the presence of solvent naphtha (50 wt .-%) at 50 to 100 ° C to the half-amide or amide ammonium salt and at 160 to 200 ° C with azeotropic culling of water of reaction to imide or diamide.
- solvent naphtha 50 wt .-%
- the degree of amidation is inversely proportional to the acid number.
- poly (alkyl (meth) acrylate As poly (alkyl (meth) acrylate), the compounds listed in the table were used as 50% settings in higher-boiling solvent. The K values are determined according to Ubbelohde at 25 ° C. in 5% strength toluene solution. Characterization of the poly (acrylates) used C1 Poly (octadecyl acrylate), K value 32 C2 Poly (dodecyl acrylate), K value 35.6 C3 Poly (phenyl acrylate), K value 22.4
- CFPP value (according to EN 116, in ° C) of various biofuels according to the above table was determined after addition of 1200 ppm, 1500 ppm and 2000 ppm of additive mixture. Percentages refer to parts by weight in the respective mixtures.
- Tables 5 to 7 show that comb polymers with the factor Q according to the invention achieve excellent CFPP reductions even at low dosing rates and offer additional potential at higher dosing rates.
- the CFPP value is used to determine the resistance to cold corrosion of an oil according to DIN EN 116 before and after a standardized cold change treatment compared.
- the additiviere oil sample is reheated to room temperature without shaking. From each of the upper, middle and lower sections of the cylinder a sample of 50 ml is drawn for CFPP measurements. A difference between the mean values of the CFPP values after storage to the CFPP value before storage and between the individual phases of less than 3 K shows a good resistance to cold flashes.
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Abstract
Description
- w1
- der molare Anteil der einzelnen Kettenlängen in den Alkylresten von Monomer 1,
- w2
- der molare Anteil der einzelnen Kettenlängen in den Alkylresten der Amid- und/oder Imidgruppen von Monomer 2,
- n1
- die einzelnen Kettenlängen in den Alkylresten von Monomer 1,
- n2
- die einzelnen Kettenlängen in den Alkylresten der Amid und/oder Imidgruppen von Monomer 2,
- i
- die Laufvariable für die einzelnen Kettenlängen in den Alkylresten von Monomer 1, und
- j
- die Laufvariable für die einzelnen Kettenlängen in den Alkylresten der Amid und/oder Imidgruppen von Monomer 2 sind.
- R1
- Wasserstoff oder Methyl,
- R2
- Wasserstoff oder C1-C4-Alkyl,
- m
- eine Zahl von 1 bis 100,
- R3
- C1-C24-Alkyl, C5-C20-Cycloalkyl, C6-C18-Aryl oder -C(O)-R4,
- R4
- C1-C40-Alkyl, C5-C10-Cycloalkyl oder C6-C18-Aryl, bedeuten.
Charakterisierung der eingesetzten Testöle | |||
Öl Nr. | CP | CFPP | |
E 1 | Rapsölsäuremethylester | -2,3 | -14°C |
E 2 | 80% Rapsölsäuremethylester + 20 % Sonnenblumenölsäuremethylester | -1,6 | -10°C |
E 3 | 90% Rapsölsäuremethylester + 10 % Sojaölsäuremethylester | -2,0 | -8°C |
C-Kettenverteilung der zur Herstellung der Testöle eingesetzten Fettsäuremethylester (Hauptbestandteile; FI.-% gemäß GC): | ||||||||||
C16 | C16' | C18 | C18' | C18" | C18"' | C20 | C20' | C22 | Σ gesättigt | |
RME | 4,4 | 0,4 | 1,6 | 57,8 | 21,6 | 8,8 | 1,5 | 0,7 | 0,2 | 7,7 |
SBME | 6,0 | 0,1 | 3,8 | 28,7 | 58,7 | 0,1 | 0,3 | 0,3 | 0,7 | 10,8 |
SojaME | 10,4 | 0,1 | 4,1 | 24,8 | 51,3 | 6,9 | 0,5 | 0,4 | 0,4 | 15,4 |
RME = Rapsölsäuremethylester; SBME = Sonnenblumenölsäuremethylester; SojaME = Sojaölsäuremethylester |
Charakterisierung der eingesetzten Ethylen-Copolymere | |||
Beispiel | Comonomer(e) | V140 | CH3/100CH2 |
A1 | 13,6 Mol-% Vinylacetat | 130 mPas | 3,7 |
A2 | 13,7 Mol-% Vinylacetat und 1,4 Mol-% Neodecansäurevinylester | 105 mPas | 5,3 |
A3 | 9,4 Mol-% Vinylacetat | 220 mPas | 6,2 |
A4 | Mischung aus EVA-Copolymer mit | ||
16 mol-% Vinylacetat und EVA mit | 95 mPas | 3,2 | |
5 mol-% Vinylacetat im Verhältnis 13:1 | 350 mPas | 5,7 |
Charakterisierung der eingesetzten Kammpolymere | |||||
Beispiel | Comonomere | Amin | Q | Säurezahl [mg KOH/g] | |
R | Mol | ||||
B1 | MSA-co-C14/16-α-Olefin (1 : 0,5 : 0,5) | C10 | 1 | 23,0 | 60 |
B2 | MSA-co-C14/16-α-Olefin (1 : 0,5 : 0,5) | C12 | 1 | 25,0 | 58 |
B3 | MSA-co-C14/16-α-Olefin (1 : 0,5 : 0,5) | C14 | 1 | 27,0 | 56 |
B4 (V) | MSA-co-C14/16-α-Olefin (1 : 0,5 : 0,5) | C16 | 1 | 29,0 | 55 |
B5 | MSA-co-C12/14-α-Olefin (1 : 0,5 : 0,5) | C14 | 1 | 25,0 | 57 |
B6 | MSA-co-C12/14-α-Olefin (1 : 0,5 : 0,5) | C12 | 1 | 23,0 | 55 |
B7 | MSA-co-C16-α-Olefin (1 : 1) | C12 | 1 | 26,0 | 56 |
B8 | MSA-co-C14-α-Olefin (1 : 1 ) | C14 | 1 | 26,0 | 58 |
B9 | MSA-co-C10-α-Olefin (1 : 1 ) | C16 | 0,5 | 25,0 | 59 |
C18 | 0,5 | ||||
B10 | MSA-co-C14/16-α-Olefin-co-Allylmethylpolyglykol (1 :0,45 : 0,45:0,1) | C12 | 1 | 25,0 | 56 |
B11 (V) | MSA-co-C10-α-Olefin (1 : 1) | C12 | 1 | 20,0 | 57 |
B12 | MSA-co-C14/16-α-Olefin (1 : 0,5 : 0,5) | C12 | 2 | 25,0 | 0,32 |
B13 | MSA-co-C14/16-α-Olefin (1 : 0,5 : 0,5) | C12 | 1 | 25,0 | 1,5 |
B14 | MSA-co-C14/16-α-Olefin (1 : 0,5 : 0,5) | di-C12 | 1 | 25,0 | 50 |
B15 (V) | Fumarat-Vinylacetat (1 : 1 ) | C14 | 2 | n.a. | 0,4 |
n.a. = nicht anwendbar (V) = Vergleichsbeispiel |
Charakterisierung der eingesetzten Poly(acrylate) | |
C1 | Poly(octadecylacrylat), K-Wert 32 |
C2 | Poly(dodecylacrylat), K-Wert 35,6 |
C3 | Poly(behenylacrylat), K-Wert 22,4 |
CFPP-Austestung in Testöl E1 | ||||||
Bsp. | Kammpolymer | Ethylen-Copolymer | Polyacrylat | CFPP in Testöl 1 | ||
1200 ppm | 1500 ppm | 2000 ppm | ||||
1 | 20 % B1 | 80 %A2 | - | -19 | -21 | -23 |
2 | 20 % B2 | 80 %A2 | - | -24 | -24 | -24 |
3 | 20 % B3 | 80 % A2 | - | -19 | -20 | -23 |
4 (V) | 20 % B4 | 80 % A2 | - | -15 | -16 | -17 |
5 | 20 % B7 | 80 % A2 | - | -21 | -22 | -24 |
6 | 20 % B9 | 80 % A2 | - | -23 | -23 | -24 |
7 | 20%B10 | 80 % A2 | - | -23 | -23 | -25 |
8 | 20%B10 | 80 % A3 | - | -18 | -20 | -21 |
9 | 10 % B10 | 90 % A1 | - | -21 | -22 | -23 |
10 (V) | 20%B11 | 80 % A2 | - | -17 | -19 | -18 |
11 | 20 % B12 | 80 % A2 | - | -19 | -22 | -21 |
12 | 20 % B13 | 80 % A2 | - | -23 | -24 | -24 |
13 | 20 % B14 | 80 % A2 | - | -21 | -23 | -24 |
14 (V) | 20 % B15 | 80 % A2 | - | -18 | -17 | -17 |
15 | 19%B2 | 76 % A2 | 5% C1 | -20 | -24 | -26 |
16 | 19%B2 | 76 % A2 | 5% C2 | -21 | -23 | -25 |
17 | 19%B2 | 76 % A2 | 5% C3 | -22 | -23 | -24 |
18 (V) | - | A2 | - | -15 | -18 | -17 |
19 (V) | - | - | C1 | -9 | -11 | -12 |
20 (V) | - | - | C3 | -18 | -17 |
CFPP-Austestung in Testöl E2 | ||||
Bsp. | Kammpolymer | Ethylen-Copolymer | CFPP in Testöl 2 | |
1500 ppm | 2000 ppm | |||
22 | 25 % B2 | 75 %A4 | -20 | -24 |
23 | 25 % B3 | 75 % A4 | -21 | -22 |
24 (V) | 25 % B4 | 75 % A4 | -13 | -15 |
25 | 25 % B5 | 75 % A4 | -21 | -23 |
21 | 25 % B6 | 75 %A4 | -19 | -22 |
26 | 25 % B7 | 75 % A4 | -21 | -24 |
27 | 25 % B8 | 75 % A4 | -20 | -23 |
28 | 30 % B9 | 70 % A2 | -21 | -24 |
29 | 20 % B10 | 80 % A3 | -20 | -22 |
30 (V) | 25 % B11 | 75 % A2 | -15 | -16 |
31 | 25 % B12 | 75 % A4 | -20 | -22 |
32 | 25 % B13 | 75 % A4 | -22 | -25 |
33 | 25 % B14 | 75 % A4 | -18 | -20 |
34 (V) | 25 % B15 | 75 % A4 | -15 | -17 |
37 (V) | - | 100 % A4 | -12 | -12 |
CFPP-Austestung in Testöl E3 | ||||||
Bsp. | Kammpolymer | Ethylen-Copolymer | Polyacrylat | CFPP in Testöl 3 | ||
1200 ppm | 1500 ppm | 2000 ppm | ||||
21 | 20 % B1 | 80 %A1 | - | -18 | -20 | -21 |
22 | 20 % B2 | 80%A1 | - | -20 | -21 | -23 |
23 | 20 % B3 | 80 % A1 | - | -20 | -22 | -21 |
24 (V) | 20 % B4 | 80 % A1 | - | -11 | -15 | -16 |
25 | 20 % B5 | 80 % A1 | - | -20 | -20 | -22 |
26 | 20 % B7 | 80%A1 | - | -20 | -21 | -23 |
27 | 20 % B8 | 80 % A1 | - | -19 | -21 | -22 |
28 | 25 % B9 | 75 % A2 | - | -20 | -21 | -23 |
29 | 15 % B10 | 85 % A3 | - | -18 | -18 | -20 |
30 (V) | 20 % B11 | 80 % A2 | - | -15 | -17 | -17 |
31 | 20 % B12 | 80 % A1 | - | -19 | -20 | -20 |
32 | 20 % B13 | 80 % A1 | - | -21 | -22 | -23 |
33 | 20 % B14 | 80 % A1 | - | -19 | -20 | -20 |
34 (V) | 20 % B15 | 80 % A1 | - | -15 | -17 | -18 |
35 | 19 % B2 | 76 % A1 | 5% C1 | -19 | -21 | -22 |
36 | 19 % B2 | 76 % A1 | 5% C3 | -20 | -21 | -23 |
37 (V) | - | A1 | - | -13 | -13 | -11 |
38 (V) | - | - | C3 | -14 | -16 | -16 |
Kühlprogramm zur Bestimmung der Kältewechselbeständigkeit: | ||||
Abschnitt | Start | Ende | Dauer | Beschreibung |
A → B | +5°C | -3°C | 8 h | Vorkühlung auf Zyklus-Start-Temperatur |
B → C | -3°C | -3°C | 2 h | stationäre Temperatur, Zyklusbeginn |
C → D | -3°C | -13°C . | 14 h | Temperaturabsenkung, beginnende Kristallbildung |
D → E | -13°C | - 13°C | 2 h | Stationäre Temperatur, Kristallwachstum |
E → F | -13°C | -3°C | 6 h | Temperaturerhöhung, Aufschmelzen der Kristalle |
F → B | Es werden weitere 6 Zyklen B → F durchgeführt. |
Eine Abweichung zwischen den Mittelwerten der CFPP-Werte nach der Lagerung zum CFPP-Wert vor Lagerung sowie zwischen den einzelnen Phasen von weniger als 3 K zeigt eine gute Kältewechselbeständigkeit.
Claims (19)
- Additiv, enthaltendA) ein Copolymer aus Ethylen und 8 bis 21 Mol-% mindestens eines Acryl- oder Vinylesters mit einem C1-C18-Alkylrest undB) ein Kammpolymer, enthaltend Struktureinheiten ausB1 ) mindestens einem Olefin als Monomer 1, welches an der olefinischen Doppelbindung wenigstens einen C8-C18-Alkylrest trägt, und
- W1
- der molare Anteil der einzelnen Kettenlängen in den Alkylresten von Monomer 1,
- w2
- der molare Anteil der einzelnen Kettenlängen in den Alkylresten der Amid- und/oder Imidgruppen von Monomer 2,
- n1
- die einzelnen Kettenlängen in den Alkylresten von Monomer 1,
- n2
- die einzelnen Kettenlängen in den Alkylresten der Amid und/oder Imidgruppen von Monomer 2,
- i
- die Laufvariable für die einzelnen Kettenlängen in den Alkylresten von Monomer 1, und
- j
- die Laufvariable für die einzelnen Kettenlängen in den Alkylresten der Amid und/oder Imidgruppen von Monomer 2 sind.
- Additiv nach Anspruch 1, worin Q von 24 bis 26 beträgt.
- Additiv nach Anspruch 1 und/oder 2, worin in Bestandteil A außer Ethylen 3,5 bis 20 Mol-% Vinylacetat und 0,1 bis 12 Mol-% 2-Ethylhexansäurevinylester, Neononansäurevinylester und/oder Neodecansäurevinylester enthalten sind, wobei der gesamte Comonomergehalt zwischen 8 und 21 Mol-% liegt.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 3, worin in Bestandteil A neben Ethylen und 8 bis 18 Mol-% Vinylestern noch 0,5 bis 10 Mol-% Olefine, ausgewählt aus Propen, Buten, Isobutylen, Hexen, 4-Methylpenten, Octen, Diisobutylen oder Norbornen enthalten sind.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 4, worin die Copolymere, die Bestandteil A ausmachen, Schmelzviskositäten zwischen 20 und 10.000 mPas aufweisen.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 5, worin die Copolymere, die Bestandteil A ausmachen, Verzweigungsgrade zwischen 1 und 9 CH3/100 CH2-Gruppen, die nicht aus den Comonomeren stammen, aufweisen.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 6, worin die Copolymere, die Bestandteil B ausmachen, Comonomere enthalten, welche von Amiden und/oder Imiden der Maleinsäure, Fumarsäure und/oder Itaconsäure abgeleitet sind.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 7, worin die Amide und/oder Imide des Bestandteils B von primären Aminen abgeleitet sind.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 8, worin die Amide und/oder Imide des Bestandteils B von Aminen mit linearen Alkylresten abgeleitet sind.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 9, worin die Amide und/oder Imide des Bestandteils B von Monoaminen abgeleitet sind.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 10, worin die mittlere Molekülmasse der erfindungsgemäßen Copolymere B zwischen 1.200 und 200.000 g/mol beträgt.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 11, worin die Copolymere, die Bestandteil B ausmachen, Comonomere enthalten, welche von α-Olefinen abgeleitet sind.
- Additiv nach einem oder mehreren der Ansprüche 1 bis 12, worin neben den Bestandteilen A und B als Bestandteil C ein Polymer oder Copolymer, welches (C10-C24-Alkyl)acrylateinheiten oder -methacrylateinheiten umfasst, mit einem Molekulargewicht von 800 bis 1.000.000 g/mol in einer Menge von bis zu 40 Gew.-% bezogen auf das Gesamtgewicht von A, B und C enthalten ist.
- Additiv nach einem der Ansprüche 1 bis 13, enthaltend polare stickstoffhaltige Paraffindispergatoren.
- Brennstoffölzusammensetzung, enthaltend ein Brennstofföl tierischen oder pflanzlichen Ursprungs und ein Additiv gemäß einem oder mehreren der Ansprüche 1 bis 14.
- Brennstoffölzusammensetzung gemäß Anspruch 15, dadurch gekennzeichnet, dass das Brennstofföl tierischen oder pflanzlichen Ursprungs einen oder mehrere Ester aus Monocarbonsäure mit 14 bis 24 C-Atomen und Alkohol mit 1 bis 4 C-Atomen enthält.
- Brennstoffölzusammensetzung nach Anspruch 16, dadurch gekennzeichnet, dass der Alkohol Methanol oder Ethanol ist.
- Brennstoffölzusammensetzung nach einem oder mehreren der Ansprüche 15 bis 17, dadurch gekennzeichnet, dass das Brennstofföl tierischen oder pflanzlichen Ursprungs mehr als 5 Gew.-% an Estern gesättigter Fettsäuren enthält.
- Verwendung eines Additivs gemäß einem oder mehreren der Ansprüche 1 bis 14 zur Verbesserung der Kaltfließeigenschaften von Brennstoffölen tierischen oder pflanzlichen Ursprungs.
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Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005097953A1 (en) * | 2004-04-06 | 2005-10-20 | Akzo Nobel N.V. | Pour point depressant additives for oil compositions |
EP1717296A1 (de) * | 2005-04-30 | 2006-11-02 | Clariant Produkte (Deutschland) GmbH | Additive für schwefelarme Mineralöldestillate, umfassend Aromaten, welche eine Hydroxygruppe, eine Methoxygruppe und eine Säurefunktion tragen |
EP1857529A1 (de) * | 2006-05-16 | 2007-11-21 | Clariant International Ltd. | Kaltfliessverbesserer für pflanzliche oder tierische Brennstofföle |
EP1857528A1 (de) * | 2006-05-16 | 2007-11-21 | Clariant International Ltd. | Kaltfliessverbesserer für pflanzliche oder tierische Brennstofföle |
WO2007147753A2 (de) * | 2006-06-22 | 2007-12-27 | Basf Se | Mischung aus polaren öllöslichen stickstoffverbindungen und säureamiden als paraffindispergator für kraftstoffe |
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WO2016083130A1 (de) | 2014-11-27 | 2016-06-02 | Basf Se | Copolymerisat und seine verwendung zur verminderung der kristallisation von paraffinkristallen in kraftstoffen |
US10557096B2 (en) | 2014-11-27 | 2020-02-11 | Basf Se | Copolymer and use thereof for reducing crystallization of paraffin crystals in fuels |
WO2017202642A1 (de) | 2016-05-24 | 2017-11-30 | Basf Se | Copolymerisat und seine verwendung zur verminderung der kristallisation von paraffinkristallen in kraftstoffen |
US11060044B2 (en) | 2016-05-24 | 2021-07-13 | Basf Se | Copolymer and use thereof for reducing crystallization of paraffin crystals in fuels |
WO2018054892A1 (de) | 2016-09-21 | 2018-03-29 | Basf Se | TERPOLYMERE AUS MALEINSÄUREANHYDRID, ACRYLATEN UND ALPHA-OLEFINEN, INSBESONDERE ZUR VERWENDUNG ALS FLIEßVERBESSERER FÜR ERDÖL |
EP3913035A1 (de) | 2020-05-20 | 2021-11-24 | Basf Se | Neue zusammensetzungen zur verminderung der kristallisation von paraffinkristallen in kraftstoffen |
WO2024037904A1 (de) | 2022-08-16 | 2024-02-22 | Basf Se | Zusammensetzung zur verminderung der kristallisation von paraffinkristallen in kraftstoffen |
WO2024115211A1 (en) | 2022-11-30 | 2024-06-06 | Basf Se | Homo- and copolymers of vinyl ethers for reducing crystallization of paraffin crystals in fuels |
Also Published As
Publication number | Publication date |
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KR101139274B1 (ko) | 2012-04-26 |
DE10349851A1 (de) | 2005-06-16 |
US20050113266A1 (en) | 2005-05-26 |
JP2005126720A (ja) | 2005-05-19 |
DE10349851B4 (de) | 2008-06-19 |
US7500996B2 (en) | 2009-03-10 |
JP4859361B2 (ja) | 2012-01-25 |
HUE025057T2 (en) | 2016-01-28 |
CA2486035A1 (en) | 2005-04-25 |
CA2486035C (en) | 2012-03-13 |
PL1526167T3 (pl) | 2015-10-30 |
KR20050039682A (ko) | 2005-04-29 |
PL1526167T5 (pl) | 2019-09-30 |
EP1526167B2 (de) | 2019-01-30 |
EP1526167A3 (de) | 2005-05-11 |
EP1526167B1 (de) | 2015-05-20 |
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