CN101528896A - Oligo- or polyamines as oxidation stabilizers for biofuel oils - Google Patents
Oligo- or polyamines as oxidation stabilizers for biofuel oils Download PDFInfo
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- CN101528896A CN101528896A CNA2007800398619A CN200780039861A CN101528896A CN 101528896 A CN101528896 A CN 101528896A CN A2007800398619 A CNA2007800398619 A CN A2007800398619A CN 200780039861 A CN200780039861 A CN 200780039861A CN 101528896 A CN101528896 A CN 101528896A
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- Prior art keywords
- alkyl
- radicals
- polyamine
- oil
- situation
- 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.)
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- 239000002551 biofuel Substances 0.000 title claims abstract description 49
- 229920000768 polyamine Polymers 0.000 title claims abstract description 49
- 239000003921 oil Substances 0.000 title abstract description 59
- 230000003647 oxidation Effects 0.000 title abstract description 5
- 238000007254 oxidation reaction Methods 0.000 title abstract description 5
- 239000003381 stabilizer Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 17
- 229930195729 fatty acid Natural products 0.000 claims abstract description 17
- 239000000194 fatty acid Substances 0.000 claims abstract description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 8
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 8
- 241001465754 Metazoa Species 0.000 claims abstract description 5
- -1 fatty acid ester Chemical class 0.000 claims description 55
- 150000001412 amines Chemical class 0.000 claims description 53
- 239000000446 fuel Substances 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 230000009183 running Effects 0.000 claims description 21
- 150000001721 carbon Chemical group 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
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- 239000003963 antioxidant agent Substances 0.000 description 13
- 230000003078 antioxidant effect Effects 0.000 description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 239000005864 Sulphur Substances 0.000 description 9
- 125000005907 alkyl ester group Chemical group 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 8
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
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- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000002283 diesel fuel Substances 0.000 description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 239000010775 animal oil Substances 0.000 description 4
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000010773 plant oil Substances 0.000 description 4
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003225 biodiesel Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
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- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 3
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 3
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 3
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
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- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 150000003868 ammonium compounds Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
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- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 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
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
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- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 2
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005908 glyceryl ester group Chemical group 0.000 description 2
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- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 2
- UKNVXIMLHBKVAE-UHFFFAOYSA-N n'-hexadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCNCCCN UKNVXIMLHBKVAE-UHFFFAOYSA-N 0.000 description 2
- 125000001402 nonanoyl group Chemical group O=C([*])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
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- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([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])[H] 0.000 description 2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000003074 decanoyl 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(*)=O 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000010771 distillate fuel oil Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 238000004980 dosimetry Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])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 1
- 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 1
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
- DXYUWQFEDOQSQY-UHFFFAOYSA-N n'-octadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCCN DXYUWQFEDOQSQY-UHFFFAOYSA-N 0.000 description 1
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 1
- BEPGHZIEOVULBU-UHFFFAOYSA-N n,n'-diethylpropane-1,3-diamine Chemical compound CCNCCCNCC BEPGHZIEOVULBU-UHFFFAOYSA-N 0.000 description 1
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 206010036596 premature ejaculation Diseases 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—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
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
-
- 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
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- 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
-
- 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
- C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
- C10L1/2286—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen triple bonds, e.g. nitriles
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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
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
-
- 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
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
- C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
- C10L1/2335—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles morpholino, and derivatives thereof
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10L10/00—Use of additives to fuels or fires for particular purposes
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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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
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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)
- Lubricants (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Use of oligo- or polyamines having a number-average molecular weight of 46 to 70 000 which are free from phenolic hydroxyl groups for increasing the oxidation stability of biofuel oils which are based on esters of fatty acids, or of mixtures of such biofuel oils with medium distillates of fossil origin and/or of plant and/or animal origin, which are essentially hydrocarbon mixtures and are free of esters of fatty acids.
Description
The present invention relates to number-average molecular weight and be 46-70000 and the few amine of phenolic hydroxy group or polyamine are not improving based on the purposes in the oxidative stability of the mixture of the biofuel oil of fatty acid ester or this biofuel oil and fossil origin and/or plant and/or zoogenous middle runnings (it is essentially hydrocarbon mixture and not fatty acid esters).
Concrete representative that the invention further relates to this widow's amine or polyamine and mixture based on the biofuel oil of fatty acid ester.
The invention further relates to comprise most of should widow's amine or the fuel of the concrete representative of polyamine by (A) and the oil fuel of (B) forming and small portion:
(A) 0.1-75 weight % at least a based on fatty acid ester biofuel oil and
(B) fossil origin of 25-99.9 weight % and/or plant and/or zoogenous middle runnings, it is essentially hydrocarbon mixture and not fatty acid esters.
Biofuel oil also is called " biofuel " usually and comprises a high proportion of unsaturated fatty acid ester usually; because the cause of himself chemical structure and be easier to oxygenolysis under the effect of atmosphericoxygen, thereby in its storage process, improve its oxidative stability usually by mixing small amount of antioxidant than the oil fuel of fossil origin.The antioxidant that typically is used for this purpose is a sterically hindered phenol, for example 2,6-di-tert-butyl-4-methy phenol (" BHT "), 3-butylhydroxy anisole (" BHA ") and tertiary butylated hydroquinone (" TBHQ "), as Mittelbach and Schober at JAOCS, 80 volumes, the document in 8 (2003) the 817-823 pages or leaves is described.Specific sulfide ester class, trivalent phosphorous compound, dithiocarbamic acid metal-salt and phosphorodithioic acid metal-salt also are used for this purpose.
Can also learn the technical information document in November, 1997 from BASF Aktiengesellschaft,
BPD, a kind of N, the N '-aromatic secondary amine of di-sec-butyl-p-phenyl enediamine's structure is suitable as the antioxidant of gasoline and rocket engine fuel.
WO03/095593 has introduced can be by making C
4-C
29Alkyl-or the succinimide that obtains of alkenyl succinic anhydride and primary amine (also can be polyamine) reaction as the additive of the thermostability that improves aviation fuel and biofuel such as vegetables oil and vegetable oil esters.
Document WO 02/102942 and EP-A1568756 disclose polyisobutenyl succinimide suitability as washing agent in biofuel oil.
WO94/19430 has described polyamine and acylating agent, especially with the reaction product of lipid acid, as the antifoams of the mixture of biofuel oil and fossil origin middle runnings.
DE10 2,004 024 532A1 disclose and have comprised that thereby most of intermediate distillate fuel oil and biofuel oil mixt and small portion are oil-soluble to have the widow of ether oxygen functional group-or the oil fuel of polymine with oxyethane or propylene oxide alkoxylate.Yet, these alkoxylates widow-or polymine at this as the emulsion splitter of fuel/water mixture.
Yet above-mentioned antioxidant such as the sterically hindered phenol stabilization in biofuel oil is still not enough usually.Particularly required dosage is too high.Therefore, the purpose of this invention is to provide more effective biofuel oil antioxidant.
This purpose is by using number-average molecular weight as 46-70 000 and the few amine of phenolic hydroxy group or polyamine improve oxidative stability and do not realize.
Cationic structural, especially ammonium compound or substituted ammonium compound are preferably got rid of outside the present invention few amine or polyamine to be used.
The number-average molecular weight of few amine or polyamine be 46 (diamino methane as may the representing of minimum time) to 70000, but this upper limit is inessential.The preferable range of number-average molecular weight be 58 (for example 1) to 40000, especially 116 to 10000, particularly 130 to 5000, most preferably 200 to 2000.
Described few amine or polyamine preferably contain 2-10 in molecule, especially 2-6 is individual, particularly 2-5 nitrogen-atoms.
In preferred embodiments, the present invention relates to the few amine of general formula I or the purposes of polyamine:
Radicals R wherein
1-R
6Be hydrogen, C independently of one another
1-C
30Alkyl, C
5-C
8Cycloalkyl, C
1-C
29Alkyl-carbonyl or C
2-C
8Cyano group alkyl, wherein radicals R
1With R
2And/or R
5With R
6Also can form with the nitrogen-atoms that is connected with it under every kind of situation and also can contain other heteroatoms (typically being nitrogen and/or oxygen and/or sulphur) and/or carbonylic carbon atom and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, perhaps also forming together under every kind of situation can be by C
1-C
30Alkyl and/or C
6-C
12The methylene radical structure division that aryl replaces,
Bridging unit A
1-A
3Be C independently of one another
1-C
12Alkylidene group and/or C
6-C
12Arylidene, wherein radicals R
1And/or R
5Under every kind of situation also can with nitrogen-atoms that is connected with it and alkylene group A
1Or A
3Carbon atom form together and also can contain other heteroatoms (typically being nitrogen and/or oxygen and/or sulphur) and/or carbonylic carbon atom and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, and
Respectively the do for oneself integer of 0-30 of variable n and m.
Described optional substituting group on five yuan or hexa-atomic saturated or unsaturated ring for example can be the long-chain or the alkyl of short chain relatively relatively, especially suitable straight chain or branched-alkyl.This moment, useful group was at first for containing 1-30, and the alkyl of preferred 1-20 carbon atom is secondly individual for containing 30-200, the preferred long chain hydrocarbon groups of 40-100 carbon atom, for example suitable polyisobutenyl.
Few amine to be used or polyamine preferably comprise at least one and contain 1-30 carbon atom in the context of the invention, especially contain 2-30 carbon atom, more preferably contain 3-30 carbon atom, and the alkyl that particularly contains 5-30 carbon atom is as radicals R
1-R
6This relative long chain hydrocarbon groups is guaranteed sufficient fuel-soluble.Thereby in an especially preferred embodiment, the present invention relates to a kind of small portion that comprises and contain at least one and contain 5-30, especially 10-22, the particularly few amine of this alkyl of 12-18 carbon atom or the fuel of polyamine.
The example of this relative long chain hydrocarbon groups comprises pure aliphatic straight chain or branched hydrocarbyl radical, and it can be a synthetic or natural.The example is a methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, the 2-butyl, isobutyl-, the tertiary butyl, amyl group, the 1-methyl butyl, the 2-methyl butyl, the 3-methyl butyl, 2, the 2-dimethyl propyl, the 1-ethyl propyl, n-hexyl, 1, the 1-dimethyl propyl, 1, the 2-dimethyl propyl, the 1-methyl amyl, the 2-methyl amyl, the 3-methyl amyl, the 4-methyl amyl, 1, the 1-dimethylbutyl, 1, the 2-dimethylbutyl, 1, the 3-dimethylbutyl, 2, the 2-dimethylbutyl, 2, the 3-dimethylbutyl, 3, the 3-dimethylbutyl, the 1-ethyl-butyl, the 2-ethyl-butyl, 1,1,2-trimethylammonium propyl group, 1,2,2-trimethylammonium propyl group, 1-ethyl-1-methyl-propyl, 1-ethyl-2-methyl-propyl, n-heptyl, n-octyl, n-nonyl, different nonyl, the 2-ethylhexyl, the 2-propylheptyl, positive decyl, the n-undecane base, dodecyl (lauryl), the n-tridecane base, isotridecyl, n-tetradecane base (myristyl), positive pentadecyl, n-hexadecyl (palmityl), the n-heptadecane base, Octadecane base (stearyl), NSC 77136 base and NSC 62789 base.These relative long chain hydrocarbon groups also can be unsaturated character, for example oil base, inferior oil base or flax base.
Alicyclic alkyl also is suitable for as the substituting group on aliphatic few amine or the polyamine in the context of the invention.The example is cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, Dimethylcyclohexyl, suberyl and ring octyl group.
Suitable relative long chain hydrocarbon groups also is straight chain or branched-alkyl carbonyl, contains 5-30 especially accordingly, and especially 10-22 is individual, particularly the fatty acid group of 12-18 carbon atom.The example is a formyl radical; ethanoyl; positive propionyl; different propionyl; positive butyryl radicals; the 2-butyryl radicals; isobutyryl; uncle's butyryl radicals; pentanoyl; 1-methylbutyryl base; 2-methylbutyryl base; 3-methylbutyryl base; 2; 2-dimethyl propylene acyl group; 1-ethyl propionyl; positive caproyl; 1; 1-dimethyl propylene acyl group; 1; 2-dimethyl propylene acyl group; 1-methylpent acyl group; 2-methylpent acyl group; 3-methylpent acyl group; 4-methylpent acyl group; 1; 1-dimethyl butyrate acyl group; 1; 2-dimethyl butyrate acyl group; 1; 3-dimethyl butyrate acyl group; 2; 2-dimethyl butyrate acyl group; 2; 3-dimethyl butyrate acyl group; 3; 3-dimethyl butyrate acyl group; 1-ethyl butyryl radicals; 2-ethyl butyryl radicals; 1; 1; 2-trimethylammonium propionyl; 1; 2,2-trimethylammonium propionyl; 1-ethyl-1-methylpropionyl; 1-ethyl-2-methylpropionyl; positive oenanthyl; positive capryloyl; positive nonanoyl; different nonanoyl; 2-ethyl hexanoyl base; 2-propyl group oenanthyl; positive decanoyl; the n-undecane acyl group; n-dodecane acyl group (lauroyl); the n-tridecane acyl group; different tridecanoyl; n-tetradecane acyl group (myristoyl); the Pentadecane acyl group; n-hexadecane acyl group (palmitoyl); the n-heptadecane acyl group; Octadecane acyl group (stearyl-); NSC 77136 acyl group and NSC 62789 acyl group.The alkyl-carbonyl of these relative long-chains also can be unsaturated character, for example oleoyl, inferior oleoyl or flax acyl group.
Be used for above-mentioned relative long-chain aliphatic hydrocarbon or relatively natural matter source particularly plant or animal tallow or oil, for example Oleum Cocois, Yatall MA, plam oil, rapeseed oil, soya-bean oil or the curcas oil of chain alkyl carbonyl.In containing relative long chain hydrocarbon groups and few amine or polyamine based on these raw materials, alkyl exists as the form of mixtures of homology form of mixtures and/or saturated and unsaturated chain inevitably.
Can prepare by the few amine or the polyamine of abovementioned alkyl carbonyl substituted by the reactive derivative of amido matter and corresponding lipid acid such as lower alkyl esters, halogenide such as fat acyl chloride or acid anhydrides with plain mode well-known to those skilled in the art.
Abovementioned alkyl carbonyl in few amine of aliphatic series or polyamine can change into the relative long-chain aliphatic hydrocarbon that contains same carbon atoms number accordingly by for example common hydride process.
Suitable bridging unit A
1-A
3All be divalence straight chain or branched aliphatic hydrocarbon structure and divalence aromatic hydrocarbon structure in principle, but preferred formula-(CH
2)
m-polyalkylene, wherein m is 1-12, especially 2-6, particularly 2-4, most preferably 2 or 3.Thereby ethylene and trimethylene are particularly advantageous.For the bridging unit that contains 2 or 3 carbon atoms, remove α, suitable bridging unit also is non-linearizer bridge receipts or other documents in duplicate unit as 1 outside the ω one-tenth key hydrocarbon structure, 1-ethylidene, 1,1-propylidene, 2,2-propylidene and propylene.Divalent aromatic bridging unit A
1-A
3Example be adjacent, and to phenylene.Bridging unit A
1-A
3Can be identical or different.
Variable n and m are the integer of 0-30 independently of one another, but this upper limit is inessential.N and m preferably are 0-6, especially 0-4, particularly 0-2 independently of one another, most preferably 0 or 1.
In particularly preferred embodiments, the present invention relates to few amine or the purposes of polyamine, the wherein radicals R of general formula I
1-R
6Be hydrogen, C independently of one another
1-C
22Alkyl, C
5Or C
6Cycloalkyl or C
1-C
21Alkyl-carbonyl,
Bridging unit A
1-A
3Be C independently of one another
2Or C
3Alkylidene group and variable n and m are respectively 0 or 1,
Condition is at least one radicals R
1-R
6Be C
5-C
30Alkyl, especially C
10-C
20Alkyl, C
5Or C
6Cycloalkyl or C
4-C
29Alkyl-carbonyl, especially C
9-C
19Alkyl-carbonyl.
Can be used for of the present inventionly containing relative short chain or relatively the typical individual example of this few amine of long chain hydrocarbon groups or polyamine is as follows:
● N, N '-dimethyl-1,3-propylene diamine
● N, N '-diethyl-1,3-propylene diamine
● N-sec.-propyl-1,3-propylene diamine
● N, N '-di-sec-butyl-p-phenyl enediamine
● N-dodecyl-1,3-propylene diamine
● N-lauroyl-1,3-propylene diamine
● N-tetradecyl-1,3-propylene diamine
● N-tetradecanoyl-1,3-propylene diamine
● N-hexadecyl-1,3-propylene diamine
● N-hexadecanoyl-1,3-propylene diamine
● N-octadecyl-1,3-propylene diamine
● N-octadecanoyl-1,3-propylene diamine
● N-oil base-1,3-propylene diamine
● N-oleoyl-1,3-propylene diamine
● N-cyclohexyl-1,3-propylene diamine
● N-(3-aminopropyl) coco amine (main component: N-dodecyl-1,3-propylene diamine)
● the appropriate that of N-(3-aminopropyl) amine (main component: N-oil base-1,3-propylene diamine)
● N-(3-aminopropyl) palmitamide (main component: N-hexadecyl-1,3-propylene diamine)
In another particularly preferred embodiment, the present invention relates to few amine or the purposes of polyamine, the wherein radicals R of general formula I
1-R
6Be hydrogen.These few amine or polyamine particularly contain the not replacement widow of straight-chain alkyl-sub-bridge-and polyalkylene amine.The example is:
● 1
● 1, the 3-propylene diamine
● 1, the 4-butanediamine
● 1, the 6-hexanediamine
● 1, the 8-octamethylenediamine
● diethylenetriamine
● dipropylenetriamine
● N-(3-aminopropyl)-1,4-butanediamine
● Triethylenetetramine (TETA)
● tri propylidene tetramine
● N, N '-two (the amino propylidene of 3-)-1
● tetren
● 4 sub-propyl-5-amine
● penten
● five inferior propyl hexamine
Other example of representative that can be used for the few amine of general formula I of the present invention and polyamine is as follows:
● N-2-cyano ethyl-N ', N '-dimethyl-1, the 3-propylene diamine replaces the representative of few amine or polyamine as the cyano group alkyl
● N-(3-amino-2, the 2-dimethyl propyl) tetramethyleneimine, N-(3-aminopropyl) pyrazine (pyrazan), N-(3-aminopropyl) morpholine, N-(3-aminopropyl)-N '-methylpyrazine, N-(3-aminopropyl)-N '-(2-hydroxyethyl) pyrazine and N-(3-aminopropyl) imidazoles are as containing radicals R
1And R
2The few amine of (it forms with the nitrogen-atoms that is connected with it and also can contain other heteroatoms and can have other substituent ring) or the representative of polyamine
● can be by N-[N '-(2-the aminoethyl)-2-aminoethyl that makes corresponding polyisobutenyl succinic anhydride and diethylenetriamine or Triethylenetetramine (TETA) prepared in reaction] polyisobutenyl succinimide and N-[N "-{ N '-(2-aminoethyl)-2-aminoethyl }-2-aminoethyl] polyisobutenyl succinimide (weight-average molecular weight of polyisobutenyl is 1000 under every kind of situation), as containing radicals R
1And R
2The few amine of (it forms with the nitrogen-atoms that is connected with it and also can contain carbonylic carbon atom and can have other substituent ring) or the representative of polyamine
● formula Ph-CH=N-(CH
2)
3-NH-(CH
2)
2-NH-(CH
2)
3The N of-N=CH-Ph, N '-two [3-(phenyl azepine methyne) propyl group]-1 is as containing radicals R
1And R
2The few amine of (it forms the methylene radical structure division that can be replaced by alkyl or aryl together) or the representative of polyamine
● 4-(2-aminoethyl) imidazoles, as radicals R wherein
1With nitrogen-atoms that is connected with it and alkylene group A
1Carbon atom can form together and also can contain other heteroatomic five yuan or the few amine of six-ring or representative of polyamine.
Because up to the present more described few amine and polyamine are not described to the biofuel oil component, so it is 1 that the present invention also provides weight ratio: 100000-1: 100, preferred 1: 50000-1: 500, especially 1: 20000-1: 1000, particularly 1: 10000-1: the few amine of 2000 general formula I or polyamine and based on the mixture of the biofuel oil of fatty acid ester, wherein
Radicals R
1-R
6Be hydrogen, C independently of one another
1-C
30Alkyl, C
5-C
8Cycloalkyl or C
2-C
8Cyano group alkyl, wherein radicals R
1With R
2And/or R
5With R
6Also can form with the nitrogen-atoms that is connected with it under every kind of situation and also can contain other heteroatoms and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, perhaps also forming together under every kind of situation can be by C
1-C
30Alkyl and/or C
6-C
12The methylene radical structure division that aryl replaces,
Bridging unit A
1-A
3Be C independently of one another
1-C
12Alkylidene group and/or C
6-C
12Arylidene, wherein radicals R
1And/or R
5Under every kind of situation also can with nitrogen-atoms that is connected with it and alkylene group A
1Or A
3Carbon atom form together and also can contain other heteroatoms and/or carbonylic carbon atom and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, and
Respectively the do for oneself integer of 0-30 of variable n and m.
Because up to the present more described few amine and polyamine be not described to the composition of the oil fuel is made up of biofuel oil and conventional middle runnings,, the present invention comprises major part by (A) and the few amine of oil fuel of (B) forming and at least a general formula I of small portion or the fuel of polyamine so also providing:
(A) 0.1-75 weight % at least a based on fatty acid ester biofuel oil and
(B) fossil origin of 25-99.9 weight % and/or plant and/or zoogenous middle runnings, it is essentially hydrocarbon mixture and not fatty acid esters,
In general formula I:
Radicals R
1-R
6Be hydrogen, C independently of one another
1-C
30Alkyl, C
5-C
8Cycloalkyl or C
2-C
8Cyano group alkyl, wherein radicals R
1With R
2And/or R
5With R
6Also can form with the nitrogen-atoms that is connected with it under every kind of situation and also can contain other heteroatoms and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, perhaps also forming together under every kind of situation can be by C
1-C
30Alkyl and/or C
6-C
12The methylene radical structure division that aryl replaces,
Bridging unit A
1-A
3Be C independently of one another
1-C
12Alkylidene group and/or C
6-C
12Arylidene, wherein radicals R
1And/or R
5Under every kind of situation also can with nitrogen-atoms that is connected with it and alkylene group A
1Or A
3Carbon atom form together and also can contain other heteroatoms and/or carbonylic carbon atom and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, and
Respectively the do for oneself integer of 0-30 of variable n and m.
Fuel element (A) also is called " biofuel " usually.This biofuel oil (A) preferably mainly comprise the effective for treatment of premature ejaculation derived from plant and/or animal oil and/or fat.Alkyl ester typically is interpreted as finger lower alkyl esters, especially C
1-C
4Alkyl ester, it can be by being present in the glyceryl ester in plant and/or animal oil and/or the fat, particularly triglyceride level utilizes lower alcohol such as ethanol, n-propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, sec-butyl alcohol, the trimethyl carbinol or particularly methyl alcohol (" FAME ": fatty acid methyl ester) carry out transesterify and obtain.
Thereby the example that can be converted into corresponding alkyl ester and can be used as the vegetables oil on biofuel basis is Viscotrol C, sweet oil, peanut oil, palm-kernel oil, Oleum Cocois, tori seed oil, Oleum Gossypii semen and especially sunflower oil, plam oil, soya-bean oil and rapeseed oil.Other example comprises can be by the oil of wheat, jute, sesame and the acquisition of Butyrospermum Parkii nut; Can also use peanut oil, curcas oil and Toenol 1140.The extraction of these oil with and be that prior art is known or can derive from prior art to the conversion of alkyl ester.
If can also after used vegetables oil such as exhausted degree of depth frying oil are suitably in suitable cleaning, change into alkyl ester, thereby with they bases as biofuel.
Vegetation fat can be used as the biofuel source in principle equally, but only accounts for small portion.
Thereby be converted into corresponding alkyl ester and can be fish oil, butter, lard and as the example of the animal grease on the basis of biofuel as butchering rubbish or utilizing farming animals or similar grease that wildlife obtains.
Saturated or unsaturated fatty acids as the basis of described plant and/or animal oil and/or fat (contains 12-22 carbon atom usually and also can have other functional group such as hydroxyl, and exist with alkyl ester) form of mixtures of lauric acid, tetradecanoic acid, palmitinic acid, stearic acid, oleic acid, linolic acid, linolenic acid, elaidic acid, erucic acid and ricinolic acid, especially these lipid acid particularly.
Find that the typical lower alkyl esters based on plant and/or animal oil and/or fat as biofuel or biodiesel fuel component for example is sunflower oil methyl esters, plam oil methyl esters (" PME "), soybean oil methyl ester (" SME ") and particularly rapeseed methylester (" RME ").
Yet, can also use monoglyceride, triglyceride and especially triglyceride level itself as the mixture of Viscotrol C or this glyceryl ester as biofuel or biodiesel fuel component.
In the context of the present invention, fuel element (B) is interpreted as referring to that boiling point is 120-450 ℃ a midbarrel fuel.This midbarrel fuel is particularly useful as diesel oil fuel, heating oil or kerosene, preferred especially diesel oil fuel and heating oil.
Midbarrel fuel refers to and obtains by distilling the crude oil and boiling point is 120-450 ℃ a fuel.Preferred use low-sulfur middle runnings, promptly comprise sulphur, especially less than 200ppm sulphur, particularly less than those of 50ppm sulphur less than 350ppm.Under special circumstances, they comprise the sulphur less than 10ppm; These middle runningss are also referred to as " no sulphur ".They are the crude oil fractions of refining under hydrogenation conditions normally, therefore only comprises the polyaromatic compound and the polar compound of small proportion.They are preferably being lower than 370 ℃, particularly are lower than 350 ℃, and have the middle runnings of 95% distillation point when being lower than 330 ℃ under special circumstances.
The middle runnings of low-sulfur and no sulphur can be obtained than the heavy crude oil cut by distilled under atmospheric pressure.The typical method for transformation that is prepared middle runnings by heavier crude fractions comprises: hydrocracking, thermo-cracking, catalytic pyrolysis, coking method and/or viscosity breaking.Depend on method therefor, these middle runningss obtain perhaps refining under hydrogenation conditions with low-sulfur or the form of not having sulphur.
Middle runnings preferably contains and is lower than 28 weight %, especially is lower than the aromatic substance of 20 weight %.The content of normal paraffin is 5-50 weight %, is preferably 10-35 weight %.
Here the middle runnings that is called fuel element (B) will also be understood that into both can be indirectly also can be derived from fossil origin such as mineral oil or Sweet natural gas by the middle runnings of biomass via gasification and the preparation of hydrogenation subsequently.Indirectly the representative instance derived from the midbarrel fuel of fossil origin is GTL (" gas change the liquid ") diesel oil fuel that utilizes Fischer-Tropsch synthesis to obtain.By the middle runnings of biomass by for example BTL (" the biological liquid that becomes ") method preparation, both can be used alone as fuel element (B), also can mix as fuel element (B) with other middle runnings.This middle runnings also comprises the hydrocarbon by the hydrogenation acquisition of fat and fatty oil.They mainly comprise normal paraffin.Common described midbarrel fuel is essentially hydrocarbon mixture and not fatty acid esters.
For example in DIN 51603 and EN 590 (also referring to the Ullmann industrial chemistry encyclopaedia, the 5th edition, the A12 volume, the 617th page and page or leaf subsequently, it incorporates the present invention at this into clearly with way of reference) more detailed description the character of heating oil and diesel oil fuel.
Described fuel also comprises conventional additives usually; for example be used to improve the fluidity improver of low-temperature performance; especially low temperature flow promoter (" middle runnings fluidity improver "), nucleator, paraffin dispersant (" the anti-heavy additive of wax ") and composition thereof, and conductivity improver, anticorrosive additive, oiliness additive, antioxidant, metal passivator, antifoams, emulsion splitter, washing agent, cetane number improver, solvent or thinner, dyestuff or spices or its mixture.
Especially owing to be present in olefinic unsaturated fatty acids acid unit in the biofuel oil of fuel element (A), biofuel oil under atmosphericoxygen unstable and its with the pure substance form and with the middle runnings blended form storage process of fuel element (B) in when taking suitable preventive measures, do not decompose gradually by oxidation.Even find to add conventional antioxidant such as sterically hindered phenol such as BHT, BHA or TBHQ not enough not effectively-the high relatively dosage of interpolation.Yet above-mentioned few amine or polyamine have been realized this purpose as improved antioxidant with satisfactory way.They also have solubility preferably usually in the biofuel coil neutralization comprises the corresponding fuel of biofuel oil.
The effective ways that discovery is used to measure the oxidative stability of biofuel oil such as FAME are the so-called Rancimat methods according to European standard 14112, wherein airflow under controlled conditions by biofuel oil, is collected in the volatile acidic adduct that forms in the oxidation and analyzes with conductometry under comparatively high temps (110 ℃).The measured sensitive time (induction time) until the specific conductivity curve rises is long more, and biofuel is stable more.The expected value of sensitive time for surpassing 7 hours, especially surpasses 8 hours, particularly above 10 hours under the minimum amount of antioxidant.The sensitive time of most of biofuels was less than 7 hours as benchmark value.For the mixture of biofuel oil and biofuel oil and conventional fossil origin middle runnings, the sensitive time is because described few amine or polyamine and significant prolongation.In order to save the interactional risk of other activeconstituents in cost and restriction and biofuel oil or the fuel, be inclined to use the antioxidant of minimum dose.
Described few amine or the allocate amount of polyamine in fuel of the present invention are generally the 10-10000 ppm by weight based on the amount of biofuel (A).The preferred dosage scope is the 20-2000 ppm by weight, especially 50-1000 ppm by weight, particularly 100-500 ppm by weight.Even most of described few amine or polyamine are 500 ppm by weight or also satisfy the requirement of long sensitive time when lower at dosage in Ranzimate test.
Described few amine or polyamine and conventional antioxidant especially sterically hindered phenol such as BHT, BHA, TBHQ, Trimethylhydroquinone or dihydroxyphenyl propane are 10 with preferred weight ratio: 1-1: 10, particularly 3: 1-1: thus 3 blended mixtures can cause the further raising of oxidation-resistance and play stabilization in biofuel oil.
Because many described few amine or polyamine are solid or waxy substance, so, have been found that advantageously amine to be dissolved in advance in the solvent so that use liquid formulation to become possibility under every kind of situation for described few amine or polyamine are allocated in biofuel oil or the fuel.In this respect, the solvent that is fit to is in particular alcohol as propyl carbinol, Pentyl alcohol, n-hexyl alcohol, n-Heptyl alcohol, n-Octanol, 2-Ethylhexyl Alcohol or 2-propyl enanthol, carboxylicesters or fatty acid ester such as rapeseed methylester, or amine such as dimethylamine, Trimethylamine 99, piperidines or morpholine.
Because its simple preparation method is well known to those skilled in the art, so few amine of described aliphatic series or polyamine can use with pure fully form, promptly do not contain trace-metal such as iron, sodium or potassium substantially, especially because the trace-metal in the fuel can cause the fault in engine and the exhaust gas catalytic converter system that any downstream is connected easily.
Following embodiment is intended to that the present invention will be described but not limits.
For following few amine, according to the sensitive time of the dosimetry in the Ranzimate of foundation European standard 14 112 test in pure biofuel oil and in the mixture of biofuel oil and conventional fossil origin middle runnings [in hour] as antioxidant.
Used few amine:
" A1 "=tetren
" A2 "=diethylenetriamine
" A3 "=N-(3-aminopropyl)-1, the 4-butanediamine
" A4 "=N-(3-aminopropyl)-N '-methylpyrazine
" A5 "=N-(3-aminopropyl) coco amine
" A6 "=N-(3-aminopropyl) palmitamide
" A7 "=N-oil base-1, the 3-propylene diamine
" A8 "=N-cyclohexyl-1, the 3-propylene diamine
" A9 "=N-(3-aminopropyl) imidazoles
" A10 "=N-2-cyano ethyl-N ', N '-dimethyl-1,3-propylene diamine
" A11 "=N, N '-two [3-(phenyl azepine methyne) propyl group]-1
" A12 "=4-(2-aminoethyl) imidazoles
" A13 "=N-(3-amino-2,2-dimethylpropyl) tetramethyleneimine
Contrast used prior art antioxidant:
" BHT "=2,6-di-t-butyl-4-cresols
Fuel used oil:
" B1 "=commercial rapeseed methylester (Camp-Biodiesel, Ochsenfurt)
The mixture of " B2 "=50 volume %B1 and the commercial fossil origin diesel oil fuel of 50 volume %
Following table has shown measurement result:
Dosage is separately based on active substance; Additive is metered into the form of 10 weight % solution in 2-Ethylhexyl Alcohol.
Claims (8)
- Number-average molecular weight be 46-70000 and not the few amine of phenolic hydroxy group or polyamine improve based on the biofuel oil of fatty acid ester or this biofuel oil be essentially hydrocarbon mixture and the purposes in the oxidative stability of the mixture of the fossil origin of fatty acid esters and/or plant and/or animal source middle runnings not.
- 2. according to the few amine of the general formula I of claim 1 or the purposes of polyamine:
WhereinRadicals R 1-R 6Be hydrogen, C independently of one another 1-C 30Alkyl, C 5-C 8Cycloalkyl, C 1-C 29Alkyl-carbonyl or C 2-C 8Cyano group alkyl, wherein radicals R 1With R 2And/or R 5With R 6Also can form with the nitrogen-atoms that is connected with it under every kind of situation and also can contain other heteroatoms and/or carbonylic carbon atom and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, perhaps also forming together under every kind of situation can be by C 1-C 30Alkyl and/or C 6-C 12The methylene radical structure division that aryl replaces,Bridging unit A 1-A 3Be C independently of one another 1-C 12Alkylidene group and/or C 6-C 12Arylidene, wherein radicals R 1And/or R 5Under every kind of situation also can with nitrogen-atoms that is connected with it and alkylene group A 1Or A 3Carbon atom form together and also can contain other heteroatoms and/or carbonylic carbon atom and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, andRespectively the do for oneself integer of 0-30 of variable n and m. - 3. according to the few amine of the general formula I of claim 2 or the purposes of polyamine, it contains at least one alkyl that contains 1-30 carbon atom as radicals R 1-R 6
- 4. according to the few amine of the general formula I of claim 3 or the purposes of polyamine, whereinRadicals R 1-R 6Be hydrogen, C independently of one another 1-C 22Alkyl, C 5Or C 6Cycloalkyl or C 1-C 21Alkyl-carbonyl,Bridging unit A 1-A 3Be C independently of one another 2Or C 3Alkylidene group andVariable n and m respectively do for oneself 0 or 1,Condition is at least one radicals R 1-R 6Be C 5-C 30Alkyl, C 5Or C 6Cycloalkyl or C 4-C 29Alkyl-carbonyl.
- 5. according to few amine or the purposes of polyamine, the wherein radicals R of the general formula I of claim 2 1-R 6Be hydrogen.
- 6. according to each the few amine or the purposes of polyamine among the claim 1-5, its amount is the 10-10000 ppm by weight based on the amount of biofuel oil.
- 7. a weight ratio is 1: 100000-1: the few amine of 100 general formula I or polyamine and based on the mixture of the biofuel oil of fatty acid ester, whereinRadicals R 1-R 6Be hydrogen, C independently of one another 1-C 30Alkyl, C 5-C 8Cycloalkyl or C 2-C 8Cyano group alkyl, wherein radicals R 1With R 2And/or R 5With R 6Also can form with the nitrogen-atoms that is connected with it under every kind of situation and also can contain other heteroatoms and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, perhaps also forming together under every kind of situation can be by C 1-C 30Alkyl and/or C 6-C 12The methylene radical structure division that aryl replaces,Bridging unit A 1-A 3Be C independently of one another 1-C 12Alkylidene group and/or C 6-C 12Arylidene, wherein radicals R 1And/or R 5Under every kind of situation also can with nitrogen-atoms that is connected with it and alkylene group A 1Or A 3Carbon atom form together and also can contain other heteroatoms and/or carbonylic carbon atom and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, andRespectively the do for oneself integer of 0-30 of variable n and m.
- 8. one kind comprises most of by (A) and the few amine of oil fuel of (B) forming and at least a general formula I of small portion or the fuel of polyamine:(A) 0.1-75 weight % at least a based on fatty acid ester biofuel oil and(B) fossil origin of 25-99.9 weight % and/or plant and/or zoogenous middle runnings, it is essentially hydrocarbon mixture and not fatty acid esters,In formula IRadicals R 1-R 6Be hydrogen, C independently of one another 1-C 30Alkyl, C 5-C 8Cycloalkyl or C 2-C 8Cyano group alkyl, wherein radicals R 1With R 2And/or R 5With R 6Also can form with the nitrogen-atoms that is connected with it under every kind of situation and also can contain other heteroatoms and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, perhaps also forming together under every kind of situation can be by C 1-C 30Alkyl and/or C 6-C 12The methylene radical structure division that aryl replaces,Bridging unit A 1-A 3Be C independently of one another 1-C 12Alkylidene group and/or C 6-C 12Arylidene, wherein radicals R 1And/or R 5Under every kind of situation also can with nitrogen-atoms that is connected with it and alkylene group A 1Or A 3Carbon atom form together and also can contain other heteroatoms and/or carbonylic carbon atom and have in addition substituent five yuan or hexa-atomic saturated or unsaturated ring, andRespectively the do for oneself integer of 0-30 of variable n and m.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06123063 | 2006-10-27 | ||
| EP06123063.7 | 2006-10-27 |
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| Publication Number | Publication Date |
|---|---|
| CN101528896A true CN101528896A (en) | 2009-09-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007800398619A Pending CN101528896A (en) | 2006-10-27 | 2007-10-23 | Oligo- or polyamines as oxidation stabilizers for biofuel oils |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20100064576A1 (en) |
| EP (1) | EP2089494A2 (en) |
| KR (1) | KR20090081376A (en) |
| CN (1) | CN101528896A (en) |
| AU (1) | AU2007310941A1 (en) |
| BR (1) | BRPI0718157A2 (en) |
| CA (1) | CA2666554A1 (en) |
| RU (1) | RU2009119726A (en) |
| WO (1) | WO2008049822A2 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0714725D0 (en) * | 2007-07-28 | 2007-09-05 | Innospec Ltd | Fuel oil compositions and additives therefor |
| WO2010060818A1 (en) * | 2008-11-25 | 2010-06-03 | Basf Se | Alkoxylated oligoamines or polyamines as oxidation stabilizers |
| DE602009000639D1 (en) * | 2008-12-09 | 2011-03-03 | Infineum Int Ltd | Process for improving oil compositions |
| GR1006805B (en) | 2009-02-26 | 2010-06-16 | Dorivale Holdings Limited, | Biodiesel containing non-phenolic additives and thereby possesing enhanced oxidative stability and low acid number. |
| US20120124896A1 (en) * | 2009-06-26 | 2012-05-24 | Research Institute Of Petroleum Processing, Sinopec | Diesel Composition and Method of Increasing Biodiesel Oxidation Stability |
| US8367593B2 (en) | 2009-10-02 | 2013-02-05 | Exxonmobil Research And Engineering Company | Method for improving the resistance to one or more of corrosion, oxidation, sludge and deposit formation of lubricating oil compositions for biodiesel fueled engines |
| US20130104447A1 (en) | 2011-10-28 | 2013-05-02 | Exxonmobil Research And Engineering Company | Dye-stable biofuel blend compositions |
| US20150210931A1 (en) * | 2014-01-28 | 2015-07-30 | Cool Planet Energy Systems, Inc. | System and method for the production of jet fuel, diesel, and gasoline from lipid-containing feedstocks |
| WO2024006694A1 (en) * | 2022-06-30 | 2024-01-04 | Bl Technologies, Inc. | Diesel fuel composition and method for reducing diesel fuel filter blocking tendency from biodiesel contaminants |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2305676A (en) * | 1940-02-29 | 1942-12-22 | Universal Oil Prod Co | Treatment of gasoline |
| US2333294A (en) * | 1940-05-31 | 1943-11-02 | Universal Oil Prod Co | Treatment of gasoline |
| US3251664A (en) * | 1960-08-04 | 1966-05-17 | Petrolite Corp | Fuel compositions containing branched polyalkylenepolyamines and derivatives thereof |
| US4279621A (en) * | 1978-09-14 | 1981-07-21 | Phillips Petroleum Company | Polyamines mixture for stabilizing certain hydrocarbons against oxidation |
| US5509944A (en) * | 1994-08-09 | 1996-04-23 | Exxon Chemical Patents Inc. | Stabilization of gasoline and gasoline mixtures |
| GB0011733D0 (en) * | 2000-05-16 | 2000-07-05 | Infineum Int Ltd | Additives for improved engine operation |
| US20040068922A1 (en) * | 2002-02-13 | 2004-04-15 | Barbour Robert H. | Fuel additive composition and fuel composition and method thereof |
| FR2839315B1 (en) * | 2002-05-03 | 2006-04-28 | Totalfinaelf France | ADDITIVE FOR IMPROVING THERMAL STABILITY OF HYDROCARBON COMPOSITIONS |
| EP1568756A1 (en) * | 2004-02-24 | 2005-08-31 | Infineum International Limited | Conductivity improving additive for fuel oil compositions |
| DE102004024532B4 (en) * | 2004-05-18 | 2006-05-04 | Clariant Gmbh | Demulsifiers for mixtures of middle distillates with fuel oils of vegetable or animal origin and water |
| DE102006017105A1 (en) * | 2006-04-10 | 2007-10-11 | Degussa Gmbh | Method for increasing the oxidation stability of biodiesel |
| EP1847583A3 (en) * | 2006-04-21 | 2008-11-05 | Infineum International Limited | Improvements in Biofuel |
| US7964002B2 (en) * | 2006-06-14 | 2011-06-21 | Chemtura Corporation | Antioxidant additive for biodiesel fuels |
-
2007
- 2007-10-23 BR BRPI0718157-4A patent/BRPI0718157A2/en not_active IP Right Cessation
- 2007-10-23 CN CNA2007800398619A patent/CN101528896A/en active Pending
- 2007-10-23 KR KR1020097008720A patent/KR20090081376A/en not_active Application Discontinuation
- 2007-10-23 AU AU2007310941A patent/AU2007310941A1/en not_active Abandoned
- 2007-10-23 US US12/447,364 patent/US20100064576A1/en not_active Abandoned
- 2007-10-23 WO PCT/EP2007/061317 patent/WO2008049822A2/en active Application Filing
- 2007-10-23 EP EP07821681A patent/EP2089494A2/en not_active Withdrawn
- 2007-10-23 RU RU2009119726/05A patent/RU2009119726A/en unknown
- 2007-10-23 CA CA002666554A patent/CA2666554A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008049822A2 (en) | 2008-05-02 |
| EP2089494A2 (en) | 2009-08-19 |
| BRPI0718157A2 (en) | 2013-11-26 |
| AU2007310941A1 (en) | 2008-05-02 |
| CA2666554A1 (en) | 2008-05-02 |
| KR20090081376A (en) | 2009-07-28 |
| RU2009119726A (en) | 2010-12-10 |
| WO2008049822A3 (en) | 2008-07-17 |
| US20100064576A1 (en) | 2010-03-18 |
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Application publication date: 20090909 |