NO318504B1 - Fremgangsmate for a forhindre oksydativ nedbrytning eller gummilignende rester i bensin, stabilisert sammensetning samt anvendelse av blanding for stabilisering av bensin - Google Patents
Fremgangsmate for a forhindre oksydativ nedbrytning eller gummilignende rester i bensin, stabilisert sammensetning samt anvendelse av blanding for stabilisering av bensin Download PDFInfo
- Publication number
- NO318504B1 NO318504B1 NO19973218A NO973218A NO318504B1 NO 318504 B1 NO318504 B1 NO 318504B1 NO 19973218 A NO19973218 A NO 19973218A NO 973218 A NO973218 A NO 973218A NO 318504 B1 NO318504 B1 NO 318504B1
- Authority
- NO
- Norway
- Prior art keywords
- tert
- oxyl
- butyl
- tetramethylpiperidin
- phenylenediamine
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 24
- 230000000087 stabilizing effect Effects 0.000 title claims description 12
- 238000010525 oxidative degradation reaction Methods 0.000 title claims description 9
- -1 aliphatic nitroxide compound Chemical class 0.000 claims description 49
- 239000002530 phenolic antioxidant Substances 0.000 claims description 40
- 150000004982 aromatic amines Chemical class 0.000 claims description 32
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 150000004986 phenylenediamines Chemical class 0.000 claims description 14
- 230000002195 synergetic effect Effects 0.000 claims description 14
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 12
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000000197 pyrolysis Methods 0.000 claims description 8
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 6
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 6
- DIPUOCQXXYYIJO-UHFFFAOYSA-N 1-n,2-n-bis(5-methylhexan-2-yl)benzene-1,2-diamine Chemical compound CC(C)CCC(C)NC1=CC=CC=C1NC(C)CCC(C)C DIPUOCQXXYYIJO-UHFFFAOYSA-N 0.000 claims description 5
- PXMJCECEFTYEKE-UHFFFAOYSA-N Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester Chemical compound COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PXMJCECEFTYEKE-UHFFFAOYSA-N 0.000 claims description 5
- CFXCGWWYIDZIMU-UHFFFAOYSA-N Octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate Chemical compound CCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 CFXCGWWYIDZIMU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 claims description 4
- DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 4
- SXPLGYBFGPYAHS-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SXPLGYBFGPYAHS-UHFFFAOYSA-N 0.000 claims description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 4
- FLZYQMOKBVFXJS-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoic acid Chemical compound CC1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O FLZYQMOKBVFXJS-UHFFFAOYSA-N 0.000 claims description 3
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 claims description 3
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- JURKUHPHNMPLCP-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) 4-tert-butylbenzoate Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)OC1CC(C)(C)N(O)C(C)(C)C1 JURKUHPHNMPLCP-UHFFFAOYSA-N 0.000 claims description 2
- CRGBPDJWOLULDY-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) acetate Chemical compound CC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 CRGBPDJWOLULDY-UHFFFAOYSA-N 0.000 claims description 2
- DRFYZAIGLPMIOS-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC=C1 DRFYZAIGLPMIOS-UHFFFAOYSA-N 0.000 claims description 2
- DSSWUSNSRXWFBO-UHFFFAOYSA-N 1-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)azepan-2-one Chemical compound C1C(C)(C)N(O)C(C)(C)CC1N1C(=O)CCCCC1 DSSWUSNSRXWFBO-UHFFFAOYSA-N 0.000 claims description 2
- WZLXKEPEPXWCBR-UHFFFAOYSA-N 1-[12-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)dodecyl]pyrrolidine-2,5-dione Chemical compound C1C(C)(C)N(O)C(C)(C)CC1CCCCCCCCCCCCN1C(=O)CCC1=O WZLXKEPEPXWCBR-UHFFFAOYSA-N 0.000 claims description 2
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 claims description 2
- ZGDGVGVOFIGJIE-UHFFFAOYSA-N 1-n,2-n-di(butan-2-yl)benzene-1,2-diamine Chemical compound CCC(C)NC1=CC=CC=C1NC(C)CC ZGDGVGVOFIGJIE-UHFFFAOYSA-N 0.000 claims description 2
- JUHXTONDLXIGGK-UHFFFAOYSA-N 1-n,4-n-bis(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(NC(CC)CC(C)CC)C=C1 JUHXTONDLXIGGK-UHFFFAOYSA-N 0.000 claims description 2
- BJLNXEQCTFMBTH-UHFFFAOYSA-N 1-n,4-n-di(butan-2-yl)-1-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CCC(C)N(C)C1=CC=C(N(C)C(C)CC)C=C1 BJLNXEQCTFMBTH-UHFFFAOYSA-N 0.000 claims description 2
- APTGHASZJUAUCP-UHFFFAOYSA-N 1-n,4-n-di(octan-2-yl)benzene-1,4-diamine Chemical compound CCCCCCC(C)NC1=CC=C(NC(C)CCCCCC)C=C1 APTGHASZJUAUCP-UHFFFAOYSA-N 0.000 claims description 2
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 claims description 2
- WICNVDWKCYMTQT-UHFFFAOYSA-N 2-N-butan-2-yl-2-N-phenylbenzene-1,2-diamine Chemical compound C1(=CC=CC=C1)N(C1=C(C=CC=C1)N)C(C)CC WICNVDWKCYMTQT-UHFFFAOYSA-N 0.000 claims description 2
- XILVRJJRCJMOAB-UHFFFAOYSA-N 2-[4,4-bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl]propanedioic acid Chemical compound C1C(C)(C)N(O)C(C)(C)CC1C(CCCC(C(O)=O)C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 XILVRJJRCJMOAB-UHFFFAOYSA-N 0.000 claims description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical group CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims description 2
- GQBHYWDCHSZDQU-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)-n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 GQBHYWDCHSZDQU-UHFFFAOYSA-N 0.000 claims description 2
- BGLKXHNUOPUFCL-UHFFFAOYSA-N 4-hydroxy-1-[2-(4-hydroxy-3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]-3,3,5,5-tetramethylpiperazin-2-one Chemical compound O=C1C(C)(C)N(O)C(C)(C)CN1CCN1C(=O)C(C)(C)N(O)C(C)(C)C1 BGLKXHNUOPUFCL-UHFFFAOYSA-N 0.000 claims description 2
- VCOONNWIINSFBA-UHFFFAOYSA-N 4-methoxy-n-(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(OC)C=C1 VCOONNWIINSFBA-UHFFFAOYSA-N 0.000 claims description 2
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 claims description 2
- JQTYAZKTBXWQOM-UHFFFAOYSA-N 4-n-octan-2-yl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CCCCCC)=CC=C1NC1=CC=CC=C1 JQTYAZKTBXWQOM-UHFFFAOYSA-N 0.000 claims description 2
- MZFCDWPEDQCRJM-UHFFFAOYSA-N 4-propan-2-yloxy-n-(4-propan-2-yloxyphenyl)aniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=C(OC(C)C)C=C1 MZFCDWPEDQCRJM-UHFFFAOYSA-N 0.000 claims description 2
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 claims description 2
- WJZRRMYMGWLZDY-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,2-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC=C1C(=O)OC1CC(C)(C)N(O)C(C)(C)C1 WJZRRMYMGWLZDY-UHFFFAOYSA-N 0.000 claims description 2
- YJLOZVIELWKSNE-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,3-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)=C1 YJLOZVIELWKSNE-UHFFFAOYSA-N 0.000 claims description 2
- ZXDIQRGIYADNBI-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) butanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 ZXDIQRGIYADNBI-UHFFFAOYSA-N 0.000 claims description 2
- GITLFISGTYWQIU-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) cyclohexane-1,4-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1CCC(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)CC1 GITLFISGTYWQIU-UHFFFAOYSA-N 0.000 claims description 2
- SIXHNVLZVKYFOR-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) hexanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SIXHNVLZVKYFOR-UHFFFAOYSA-N 0.000 claims description 2
- CKJMHSMEPSUICM-UHFFFAOYSA-N di-tert-butyl nitroxide Chemical group CC(C)(C)N([O])C(C)(C)C CKJMHSMEPSUICM-UHFFFAOYSA-N 0.000 claims description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 2
- KXQXILJJTWHMRW-UHFFFAOYSA-N n,n'-bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)hexanediamide Chemical compound C1C(C)(C)N(O)C(C)(C)CC1NC(=O)CCCCC(=O)NC1CC(C)(C)N(O)C(C)(C)C1 KXQXILJJTWHMRW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- NYLGUNUDTDWXQE-UHFFFAOYSA-N n-phenyl-n-prop-2-enylaniline Chemical compound C=1C=CC=CC=1N(CC=C)C1=CC=CC=C1 NYLGUNUDTDWXQE-UHFFFAOYSA-N 0.000 claims description 2
- RVWJIVLFXACVCQ-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC1CC(C)(C)N(O)C(C)(C)C1 RVWJIVLFXACVCQ-UHFFFAOYSA-N 0.000 claims 1
- PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical group CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 claims 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims 1
- KZNDXCVEWRZEEU-UHFFFAOYSA-N 4-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1CCCCC1 KZNDXCVEWRZEEU-UHFFFAOYSA-N 0.000 claims 1
- MYKPPUUOBUFFML-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,4-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=C(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)C=C1 MYKPPUUOBUFFML-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 description 15
- 239000000446 fuel Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- 238000011105 stabilization Methods 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 2
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- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 239000010771 distillate fuel oil Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 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
- 239000012184 mineral wax Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
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- 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
- C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
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- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
- C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
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- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
- C10L1/1835—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom having at least two hydroxy substituted non condensed benzene rings
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Description
Foreliggende oppfinnelse vedrører en fremgangsmåte for å forhindre oksydativ nedbrytning eller gummilignende rester i bensin, stabilisert sammensetning samt anvendelse av blanding for stabilisering av bensin.
Bensin, som anvendes omfattende som et drivstoff for forbrenningsmotorer med indre forbrenning, er en blanding av forskjellige hydrokarboner. Bensin fremstilles ved en rekke forskjellige prosesser. Den virkelige sammensetningen av en bensin bestemmes delvis ved fremstillingsrfemgangsmåtene som anvendes for å formulere den, og kan også variere med den ønskede sluttanvendelsen for drivstoffet. Blant produksjons-fremgangsmåtene er: fraksjonert destillasjon av råolje for å fremstille direkte destillert drivstoff; krakking av hydrokarboner med høy molekylvekt enten termisk for å fremstille "coker" bensin eller katalytisk i en FCC (fluidisert katalytisk krakker); kobling av propyl- og butylfraksjoner med lav molekylvekt for å danne "dimate" bensin; reformering kan katalytisk fremstille høyoktanbensin fra råstoff med lavere oktantall; og som et biprodukt ved lavere olefin (etylen, propylen, osv.) produksjon for å danne pyrolysebensin eller "pygas".
Helt uavhengig av fremgangsmåten anvendt for å fremstille bensinen er stabilitet, spesielt mot oksydativ nedbrytning, et alvorlig problem. Bensin, så vel som andre hydrokarbondrivstoffer, er kjent for å danne avsetninger eller gummier både ved lagring og under reelle anvendelsesbetingelser. Disse restene kan forårsake alvorlige problemer: f.eks. kan de forårsake at ventiler kleber og slike utfellinger kan forårsake at filtere går tette. Disse problemene kan i negativ retning påvirke både håndterings- og forbren-ningsytelsen av drivstoffet. Blant de forskjellige typene bensin er pygas og krakket bensin (både "coker" og FCC) de som er mest utsatt for oksydasjon og avsetningsdannelse.
Arbeid innenfor området bensinstabilisering har vært utført over flere år. En vanlig klasse av stabiliseringsmidler for dette formålet er fenylendiaminene (PDA) anvendt alene eller i blanding med andre materialer. U.S. patent nr. 3,322,520 og 3,556,748 lærer at fenylendiaminet vanligvis er N,N'-disubstituert med substituenter som enten er alifatiske eller aromatiske. U.S. patent nr. 5,509,944 lærer at blandinger av PDA, hindrede fenoler og dimetylsulfoksyd (DMSO) virker bedre enn PDA alene. Fenylendiaminer fungerer ikke like godt som stabiliseringsmidler når bensinen har et høyt syretall (større enn 0,1 mg KOH/g bensin). U.S. patent nr. 5,169,410 lærer at anvendelsen av et sterkt basisk organisk amin kan øke stabiliseringsvirkningen av fenylendiamin, ved preferensiell reaksjon med syreenheter.
U.S. patent nr. 2,305,676 og 2,333,294 demonstrerer at anvendelsen av N-substituerte p-aminofenolderivater og visse polyaminer er effektive ved stabilisering av en rekke bensiner. U.S. patent nr. 4,648,885 beskriver at en blanding av polyaminer og N,N-dietylhydroksylamin er en effektiv stabilisator for destillatdrivstoffoljer.
GB 1 316 342 foreslår diarylnitroksyder som verdifulle forbindelser for å forhindre uønsket oksydasjon av hydrokarboner så som bensin, smøreoljer, mineraloljer eller vokser.
US-A-5,290,888 og fransk patentpublikasjon 2256157 beskriver anvendelsen av N-oksylpiperidiner for å forhindre polymerisasjon av umettede monomerer som fører til dannelsen av gummier og avsetninger i bensiner.
På tross av disse bestrebelsene består det imidlertid fortsatt et behov for å stabilisere bensin mer effektivt. Dette behovet er størst i området med mindre stabile pyrolyse- og "coker"-bensiner på grunn av deres høye nivå av umettethet og bensiner som har et høyt nivå av syreforurensninger.
Formålet med foreliggende oppfinnelse er å tilveiebringe en fremgangsmåte hvorved bensin, spesielt bensin fremstilt ved krakking eller som et biprodukt av olefinsyntese (pygas), kan stabiliseres mot oksydativ nedbrytning og avsetningsdannelse.
Foreliggende oppfinnelse bygger på anvendelsen av en synergistisk blanding av en alifatisk nitroksydforbindelse og et aromatisk amin eller en fenolisk antioksydant, eller blanding av aromatisk amin og fenolisk antioksydant, som et additiv for bensin-blandinger som vil inhibere deres oksydasjon og forhindre dannelsen av gummiaktige avsetninger eller andre avsetninger når bensin bearbeides og lagres. Bensinblandingen kan inneholde, men er ikke begrenset til, en eller flere av de tidligere omtalte direkte destillerte, "coker", FCC, dimat, reformerte eller pyrolysebensinene. Spesielt de meget ustabile pyrolyse- og "coker" bensinene stabiliseres effektivt ved anvendelsen av de alifatiske nitroksydstabiliseringsmidlene.
Foreliggende fremgangsmåte for å forhindre oksydativ nedbrytning og dannelse av gummiaktige rester eller avsetning er kjennetegnet ved at den innbefatter tilsetning til bensin av en effektiv stabiliserende mengde av en synergistisk blanding av en alifatisk nitroksydforbindelse og et aromatisk amin eller en fenolisk antioksydant
eller blanding av aromatisk amin og fenolisk antioksydant.
Fortrinnsvis er det alifatiske nitroksydet et hindret amin alifatisk nitroksyd.
Det alifatiske nitroksydet kan være av flere forskjellige klasser. Alifatiske (ofte hindret amin) alifatiske nitroksyder har vist seg å være effektive i foreliggende prosess. Spesielt foretrukket er de hindrede aminnitroksylrestene generelt, dvs. forbindelser som har minst en NO<*->gruppe, hvor <*>asterisken angir et uparet elektron og nitrogenatomet videre er flankert av to karbonatomer, hvortil ingen av hydrogenatomene er knyttet. Disse flankerende karbonatomene kan videre være forbundet med forskjellige brodannende grupper for ådanne cykliske strukturer, så som f.eks. 6-leddede piperidi-ner, piperaziner, 5-leddede pyrrolidiner og lignende, som eksemplifisert ved listen nedenfor:
di-tert-butylnitroksyl,
l-oksyl-2,2,6,6-tetrametylpiperidin,
l-oksyl-2,2,6,6-tetrametylpiperidin-4-oI,
l-oksyl-2,2,6,6-tetrametylpiperidin-4-on,
1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl acetat, 1 -oksyl-2,2,6,6-tetrametylpipeirdin-4-yl 2-etylheksanoat, l -oksyl-2,2,6,6-tetrametylpiperidin-4-yl stearat, 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl benzoat, 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl 4-tert-butylbenzoat,
bis( 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)suksinat,
bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)adipat,
bis( 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)sebakat,
bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)n-butylmalonat,
bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)ftalat,
bis( 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)isoftalat,
bis(l-oksyl-2,2,6,6-terametylpiperidin-4-yl)tereftalat,
bis( 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)heksahydrotereftalat, N,N'-bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)adipamid,
N-( 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)kaprolaktam,
N-(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)dodecylsuksinimid, 2,4,6-tris-( 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)cyanurat,
2,4,6-tris-[N-butyl-N-(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl]-s-triazin, l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl 3,5-di-tetr-butyl-4-hydroksyhydrocinnamat
eller
4,4'-etylenbis(l-oksyl-2,2,6,6-tetrametylpiperazin-3-on).
Spesielt foretrukket er det hindrede aminoalifatiske nitroksydet bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)sebakat.
Foretrukket er også l-oksyl-2,2,6,6-tetrametylpipeirdin-4-ol.
Eksempler og preferanser vedrørende det alifatiske nitroksydet er beskrevet ovenfor.
Fortrinnsvis er det aromatiske aminet et substituert fenylendiamin.
Spesielt foretrukne aromatiske aminer er:
N,NMi-isopropyl-p-fenylendiamin,
N,N'-di-sek.-butyl-p-fenylendiamin,
N,N'-di-sek.-butyl-o-fenylendiamin,
N,N'-bis( 1,4-dimetylpentyl)-p-fenylendiamin,
N,N'-bis(l-etyl-3-metylpentyl)-p-fenylendiamin,
N,N'-bis(l-metyhlheptyl)-p-fenylendiamin,
N^-dicykloheksyl-p-fenylendiamin,
N^-difenyl-p-fenylendiamin,
N,N'-di-(2-naftyl)-p-fenylendiamin,
N-isopropyl-N'-fenyl-p-fenylendiamin,
N-sek.-butyl-N-fenyl-o-fenylendiamin,
N-( 1,3-dimetylbutyl)-N'-fenyl-p-fenylendiamin,
N-( 1 -metylheptyl)-N'-fenyl-p-fenylendiamin,
N-cykloheksyl-N'-fenyl-p-fenylendiamin,
N,N'-dimetyl-N,N'-di-sek.-butyl-p-fenylendiamin,
N,N'-di( 1,4-dimetylpentyl)-o-fenylendiamin,
difenylamin,
N-allyldifenylamin,
di-(4-isopropoksyfenyl)amin,
N-fenyl-1 -naftylamin,
N-fenyl-2-naftylamin,
oktylert difenylamin,
p-p'-di-tert-oktyldifenylamin,
di-(4-metoksy-fenyl)amin,
tert-oktylert N-fenyl-1-naftylamin, eller
en blanding av mono- og dialkylerte tert-butyl-/tert-oktyldifenylaminer.
Spesielt foretrukne aminer er N-fenyl-1-naftylamin, N-fenyl-2-naftylamin, oktylert difenylamin, p,p'-di-tert-oktyldifenylamin, en blanding av mono- og dialkylert tert-butyl-/tert-oktyldifenylaminer, eller N,N'-di(l ,4-dimetylpentyl)-p-fenylendiamin.
Noen fenoliske antioksydanter av interesse er angitt nedenfor:
Alkylerte monofenoler
2,6-di-tert-butyl-4-metylfenol, 2,6-di-tert-butylfenol, 2-tert-butyl-4,6-dimetyl-fenol, 2,6-di-tert-butyl-4-etyl-fenol, 2,6-di-tert-butyl-4-n-butylfenol, 2,6-di-tert-butyl-4-i-butyl-fenol, 2,6-di-cyklopentyl-4-metylfenol, 2-(B-metylcykloheksyl)-4,6-dimetylfenol, 2,6-di-okta-decyl-4-metylfenol, 2,4,6-tri-cykloheksylfenol, 2,6-di-tert-butyl-4-metoksy-metylfenol, o-tert-butylfenol.
Alkyliden- bisfenoler
2,2'-metylen-bis-(6-tert-butyl-4-metylfenol), 2,2'-metylen-bis-(6-tert-butyl-4-etylfenol), 2,2,-metylen-bis-(4-metyl-6-(a-metyl-cykloheksyl)-fenol), 2,2'-metylen-bis-(4-metyl-6-cykloheksylfenol), 2,2'-metylen-bis-(6-nonyl-4-metylfenol), 2,2'-metylen-bis-(4,6-di-tert-butylfenol), 2,2'-etyliden-bis-(4,6-di-tert-butylfenol), 2,2'-etyliden-bis-(6-tert-butyl-4-eller -5-isobutylfenol), 2,2'-metylen-bis-(6-(a-metylbenzyl-4-nonylfenol), 2,2'-metylen-bis-(6-(a,a-di-metylbenzyl)-4-nonylfenol), 4,<4>'-metylen-bis-(2,6-di-tert-butyl-fenol), 4,4'-metylen-bis-(6-tert-butyl-2-metylfenol), 1,1 -bis-(5-tert-butyl-4-hydroksy-2-metyl-fenol)-butan, 2,6-di-(3-tert-butyl-5-metyl-2-hydroksy-benzyl)-4-metyl-fenol, 1,1,3-tris-(5-tert-butyl-4-hydroksy-2-metylfenyl)-3-n-dodecyl)-merkaptobutan, etylenglykol-bis-[3,3-bis-(3'-tert-butyl-4'-hydroksyfenyl)-butyrat], bis-(3-tert-butyl-4-hydroksy-5-metylfenyl)-dicyklopentadien, bis-[2-(3,-tert-butyl-2,-hydroksy-5'-metyl-benzyl)-6-tert-butyl-4-metyl-fenyl]-tereftalat.
Den fenoliske antioksydanten av spesiell interesse er valgt fra gruppen bestående av n-oktadecyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat, neopentantetrayl tetrakis(3,5-di-tert-butyl-4-hydroksyhydrocinnamat), di-noktadecyl 3,5-di-tert-butyl-4-hydroksy-benzylfosfonat, tiodietylen bis(3,5-di-tert-butyl-4-hydroksyhydrocinnamat), 1,3,5-trimetyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroksybenzyl)benzen, 3,6-dioksaoktametylen bis(3-metyl-5-tert-butyl-4-hydroksyhydrocinnamat), 2,6-di-tert-butyl-p-kresol, 2,2'-etyliden-bis(4,6-di-tert-butylfenol), 1,1,3-tris(2-metyl-4-hydroksy-5-tert-butylfenyl)-butan, 3,5-di-(3,5-di-tert-butyl-4-hydroksybenzyl)mesitol, heksametylen bis(3,5-di-tert-butyl-4-hydroksy-hydrocinnamat), l-(3,5-di-tert-butyl-4-hydroksyanilino)-3,5-di-(oktyltio)-s-triazin, N,N,-heksametylen-bis(3,5-di-tert-butyl-4-hydroksyhydro-cinnamamid), etylen bis[3,3-di(3-tert-butyl-4-hydroksyfenyl)butyrat], oktyl 3,5-di-tert-butyl-4-hydroksybenzylmerkaptoacetat, bis(3,5-di-tert-butyl-4-hydroksyhydro-cinnamoyOh<y>drazid, N,N'-bis[2-(3,5-di-tert-butyl-4-hydroksyhydrocinnamoyloksy)-etyl]-oksamid, 2,6-di-tert-butylfenol, oktyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat og metyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat.
Foretrukne fenoliske antioksydanter er neopentantetrayl tetrakis(3,5-di-tert-butyl-4-hydroksyhydrocinnamat), n-oktadecyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat, l,3,5-trimetyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroksybenzyl)benzen, 2,6-di-tert-butyl-p-kresol, 2,2-etyliden-bis(4,6-di-tert-butylfenol), metyl 3,5-di-tert-butyl-4-hydroksy-hydrocinnamat, oktyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat, 2,6-di-tert-butylfenol eller 3,6-dioksaoktametyIen bis(3-metyl-5-tert-butyl-4-hydroksyhydrocinnamat).
Spesielt foretrukne fenoliske antioksydanter er metyl 3,5-di-tert-butyl-4-hydroksy-hydrocinnamat, oktyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat eller 2,6-di-tert-butylfenol.
Når en slik blanding av alifatisk nitroksydforbindelse og aromatisk amin, spesielt et substituert fenylendiamin, eller en fenolisk antioksydant anvendes er den effektive stabiliserende mengden fra 0,05 til 5000 ppm av alifatisk nitroksyd og 0,05 til 5000 ppm av aromatisk amin, spesielt substituert fenylendiamin, eller fenolisk antioksydant, fortrinnsvis fra 0,1 til 100 ppm av alifatisk nitroksyd pluss 0,1 til 100 ppm aromatisk amin, spesielt substituert fenylendiamin, eller fenolisk antioksydant eller blanding av aromatisk amin og fenolisk antioksydant.
Det er også mulig å kombinere funksjonalitetene representert ved den synergistiske blandingen beskrevet ovenfor i det samme molekylet. Et slikt molekyl ville være forbindelsen beskrevet av L.P. Nethsinghe og G. Scott, Rubber Chem. Technology, 57(5), 918 (1984) som l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat.
Foretrukne utførelsesformer av foreliggende oppfinnelse innbefatter en fremgangsmåte hvor den synergistiske blandingen er fra 1 til 95 vekt-% alifatisk nitroksydforbindelse og 99 til 5 vekt-% av et aromatisk amin, fenolisk antioksydant eller blanding derav hvor forholdet mellom amin og fenolisk antioksydant er 5:1 til 1:5.
En mer foretrukket utførelsesform innbefatter blandingen som dannes fra 5 til 75 vekt-% alifatisk nitroksydforbindelse og 95 til 25 vekt-% av et aromatisk amin, fenolisk antioksydant eller blanding derav, hvor forholdet mellom amin til fenolisk antioksydant er 2:1 til 1:2.
En ytterligere mer foretrukket utførelsesform innbefatter blandingen som er fra 10 til 50 vekt-% av alifatisk nitroksydforbindelse og 90 til 50 vekt-% av et aromatisk amin, fenolisk antioksydant eller blanding derav, hvor forholdet mellom amin og fenolisk antioksydant er 1:1.
En foretrukket utførelsesform er den synergistiske blandingen hvor det alifatiske nitroksydet er bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)sebakat, det aromatiske aminet er N,N'-di(l ,4-dimetyl-pentyl)fenylendiamin og den fenoliske antioksydanten er metyl 3)5-di-tert-butyl-4-hydroksy-hydrocinnamat.
Nok en utførelsesform av foreliggende oppfinnelse vedrører en sammensetning stabilisert mot oksydativ nedbrytning og mot dannelsen av gummiaktige rester eller uønskede avsetninger som innbefatter
(a) bensin, og
(b) en effektiv stabiliserende mengde av en synergistisk blanding av en alifatisk nitroksydforbindels og et aromatisk amin eller en fenolisk antioksydant eller blanding av aromatisk amin og fenolisk antioksydant.
Eksempler og preferanser innbefattende foretrukne forhold og mengder for de individuelle komponentene er nevnt tidligere og gjelder også for sammensetningene.
Fortrinnsvis er bensinen pyrolyse- eller "coker" bensin.
Sammensetningene kan fremstilles ved å oppløse det alifatiske nitroksydet, det aromatiske aminer eller den fenolisk antioksydanten direkte i bensinen. Det er imidlertid også mulig å oppløse komponentene i et egnet oppløsningsmiddel og å tilsette de foroppløste komponentene til bensinen.
Egnede oppløsningsmidler er f.eks. alifatiske hydrokarboner, aromatiske hydrokarboner så som benzen, toluen eller xylen, ketoner eller etere.
En ytterligere utførelsesform av foreliggende oppfinnelse vedrører anvendelsen av en synergistisk blanding av en alifatisk nitroksydforbindelse og et aromatisk amin eller en fenolisk antioksydant eller blanding av aromatisk amin og fenolisk antioksydant for stabilisering av bensin mot oksydativ nedbrytning og mot dannelsen av gummirest eller uønskede avsetninger.
De etterfølgende eksemplene illustrerer oppfinnelsen.
Flere standard, akselererte testmetoder er kjent for vurderingen av stabiliteten av driv-stoffer generelt, og bensin spesielt. To vanlige ASTM fremgangsmåter for bensin er (1) D 525 Test Method for Oxidation Stability of Gasoline (Induction Period Method); og (2) D 873 Standard Test Method for Oxidation Stability of Aviation Fuels (Potential Residue Method). Schrepfer og Stansky rapporterte i Gasolin Stability Testing and Inhibitor Application, Nation Fuels and Lubricants Meeting (1981), at den sistnevnte fremgangsmåten var langt bedre til å forutsi langvarig avsetningsdannelse i både stabile og ustabile bensiner. Denne fremgangsmåten er anvendt for å bedømme de foreliggende alifatiske nitroksydstabiliseringsmidlene.
Eksempel 1
Prøven av bensin anvendt i eksemplene samles fra en olefinproduksjonsenhet (pygas). Det er en 1:1 blanding av inhibitorfrie C5- og C9+-strømmer. Prøvene samles i oksygenfrie beholdere avkjølt i et isbad og lagres i en kjøleenhet under nitrogen.
Ifølge ASTM D 873-88, oppvarmes en 100 ml prøve av pyrolysebensin i en bombe i et kokende vannbad under oksygen i 4 timer. De stabiliserte bensinprøvene fremstilles ved å tilsette 2 ml av en toluenoppløsning av stabiliseringsmidlet til 98 ml pyrolysebensin idet det dannes et totalvolum på 100 ml. Etter oppvarming fjernes den eldede bensinen fra bomben og den totale mengden gummirest bestemmes.
Tabell 1 nedenfor inneholder resultatene oppnådd når det kjente bensinstabiliserings-midlet N,N'-di(l,4-dimetylpentyl)fenylendiamin, testes enten alene eller med et hindret fenolisk kostabiliseirngsmiddel. Disse formuleringene bedømmes for å virke som en målesnor for sammenligning av effektiviteten av de alifatiske nitroksydstabilisator-systemene.
Tabell 1
Effekt av substituerte fenylendiaminstabiliseringsmiddelsystemer på Pygas gummirestdannelse i ASTM D 873 Potential Gum Test
Konsentrasjon av komponenter i ppm
Kombinasjonen av et substituert fenylendiamin (A) pluss en fenolisk antioksydant (B), hver ved en konsentrasjon på 12,5 ppm gir 2,2 mg/100 ml gummirestdannelse, mens forbindelse (A) i kombinasjon med fenolisk antioksydant (C) hver ved en konsentrasjon på 25 ppm reduserer gummirestdannelse til et ønskelig lavt nivå (1,1 mg/100 ml).
Tabell 2 nedenfor demonstrerer effektiviteten av alifatiske nitroksydstabiliseringsmidler når de anvendes alene. Selv ved en konsentrasjon på 1 ppm har et alifatisk nitroksyd tilnærmet den ekvivalente virkningen av det substituerte fenylendiaminstabiliserings-midlet ved 10 ppm.
Tabell 2
Effekt av alifatiske nitroksydstabiliseringsmiddelsystemer på Pygas gummirestdannelse i ASTM D 873 Potential Gum Test
Konsentrasjon av komponenter i ppm
Alifatiske nitroksyder D og G ved 10 ppm konsentrasjon er grovt sett 10 ganger mer effektive enn fenylendiamin A ved 10 ppm ved forebyggelse av gummirestdannelse.
Selv om de alifatiske nitroksydene demonstrerer overlegen stabiliseringsvirkning
sammenlignet med den nåværende teknikkens stand, kan denne virkningen forbedres ytterligere ved å anvende synergistiske blandinger av slike alifatiske nitroksyder med forskjellige kostabiliseirngsmidler som det fremgår i tabell 3.
Tabell 3
Effekt av alifatiske nitroksydstabiliseirngsmiddelsystemer på Pygas gummirestdannelse i ASTM D 873 Potential Gum Test
Konsentrasjon av komponenter i ppm
Fra tabell 3 er det klart at kombinasjonen av et hindret amin alifatisk nitroksyd D eller G med det substituerte fenylendiaminet A eller en fenolisk antioksydant C gir synergistisk stabilisering. Selv blandinger av alifatisk nitroksyd D med diarylamin F, som i seg selv er tilnærmet inaktivt alene, gir effektiv stabilisering.
Claims (14)
1.
Fremgangsmåte for å forhindre oksydativ nedbrytning eller dannelse av gummiaktig rest eller avsetning, karakterisert ved at den innbefatter
tilsetning til bensin av en effektiv stabiliserende mengde av en synergistisk blanding av en alifatisk nitroksydforbindelse og et aromatisk amin eller en fenolisk antioksydant eller blanding av aromatisk amin og fenolisk antioksydant.
2.
Fremgangsmåte ifølge krav 1, karakterisert ved at det alifatiske nitroksydet er et hindret amin alifatisk nitroksyd.
3.
Fremgangsmåte ifølge krav 2, karakterisert ved at det alifatiske nitroksydet er di-tert-butylnitroksyl, l-oksyl-2,2,6,6-tetrametylpiperidin, l-oksyl-2,2,6,6-tetrarnetylpipeirdin-4-ol, l-oksyl-2,2,6,6-tetrametylpiperidin-4-on, l-oksyl-2,2,6,6-tetrametylpipeirdin-4-yl acetat,
1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl 2-etylheksanoat,
1 -oksyl-2,2,6,6-tetrametylpipeirdin~4-yl stearat,
1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl benzoat,
1 -oksyl-2,2,6,6-tetrametylpipeirdin-4-yl 4-tert-butylbenzoat, bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)suksinat, bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)adipat, bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)sebakat, bis( 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)n-butylmalonat, bis( 1 -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)ftalat, bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)isoftalat, bis(l-oksyl-2,2,6,6-terametylpiperidin-4-yl)tereftalat, bis(l -oksyl-2,2,6,6-tetrametyIpiperidin-4-yl)heksahydrotereftalat, N,N'-bis(l -oksyl-2,2,6,6-tetrametylpiperidin-4-yl)adipamid, N-(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)kaprolaktam, N-(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)dodecylsuksinimid, 2,4,6-tris-(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)cyanurat,
2J4,6-tris-[N-butyl-N-(l-oksyl-2,2,6,6-tetrarnetylpiperidin-4-yl]-s-triazin, l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl 3,5-di-tetr-butyl-4-hydroksyhydrocinnamat eller
4,4'-etylenbis(l-oksyl-2,2,6,6-tetrametylpiperazin-3-on).
4.
Fremgangsmåte ifølge krav 1, karakterisert ved at det aromatiske aminet er et substituert fenylendiamin.
5.
Fremgangsmåte ifølge krav 1, karakterisert ved at det aromatiske aminet er N,N'-di-isopropyl-p-fenylendiamin,
N,N'-di-sek.-butyl-p-fenylendiamin,
N,N'-di-sek.-butyl-o-fenylendiamin,
N,N'-bis(l,4-dimetylpentyl)-p-fenylendiamin, N,N'-bis(l-etyl-3-metylpentyl)-p-fenylendiamin, N,N'-bis(l-metyhlheptyl)-p-fenylendiamin,
N.N^dicykloheksyl-p-fenylendiamin,
NjN^difenyl-p-fenylendiamin,
N,N<1->di-(2-naftyl)-p-fenylendiamin,
N-isopropyl-N'-fenyl-p-fenylendiamin,
N-sek.-butyl-N-fenyl-o-fenylendiamin, N-( 1,3-dimetylbutyl)-N'-fenyl-p-fenylendiamin, N-( 1 -metylheptyl)-N'-fenyl-p-fenylendiamin,
N-cykloheksyl-N-fenyl-p-fenylendiamin, N,N'-dimetyl-N,N'-di-sek.-butyl-p-fenylendiamin, N,N'-di( 1,4-dimetylpentyl)-o-fenylendiamin,
difenylamin, N-allyldifenylamin, di-(4-isopropoksyfenyl)amin,
N-fenyl-1 -naftylamin,
N-fenyl-2-naftylamin,
oktylert difenylamin,
p-p'-di-tert-oktyldifenylamin, di-(4-metoksy-fenyl)amin,
tert-oktylert N-fenyl-1-naftylamin, eller
en blanding av mono- og dialkylerte tert-butyl-/tert-oktyldifenylaminer.
6.
Fremgangsmåte ifølge krav 4, karakterisert ved at det aromatiske aminet er N-fenyl-1-naftylamin, N-fenyl-2-naftylamin, oktylert difenylamin, p,p'-di-tert-oktyl-difenylamin, en blanding av mono- og dialkylerte tert-butyl-/tert-oktyldifenylaminer, eller N,N'-di(l ,4-dimetylpentyl)-p-fenylendiamin.
7.
Fremgangsmåte ifølge krav 1, karakterisert ved at den fenoliske antioksydanten er neopentantetrayl tetrakis(3,5-di-tert-butyl-4-hydroksyhydrocinnamat), n-oktadecyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat, 1,3,5-trimetyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroksybenzyl)benzen, 2,6-di-tert-butyl-p-kresol, 2,2'-etyliden-bis(4,6-di-tert-butylfenol), metyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat, oktyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat, 2,6-di-tert-butyl-fenol eller 3,6-dioksaoktametylen bis(3-metyl-5-tert-butyl-4-hydroksyhydrocinnamat).
8.
Fremgangsmåte ifølge krav 7, karakterisert ved at den fenoliske antioksydanten er 3,5-di-tert-butyl-4-hydroksyhydrocinnamat, oktyl 3,5-di-tetr-butyl-4-hydroksyhydrocinnamat eller 2,6-di-tert-butylfenol.
9.
Fremgangsmåte ifølge krav 1, karakterisert ved at den effektive stabiliserende synergistiske blandingen innbefatter 0,05 til 5000 ppm av alifatisk nitroksydforbindelse og 0,05 til 5000 ppm av et aromatisk amin, fenolisk antioksydant eller blanding av aromatisk amin og fenolisk antioksydant.
10.
Fremgangsmåte ifølge krav 1,karakterisert ved at den synergistiske blandingen er fra 1 til 95 vekt-% av alifatisk nitroksydforbindelse og 99 til 5 vekt-% av et aromatisk amin, fenolisk antioksydant eller blanding derav, hvor forholdet mellom amin og fenolisk antioksydant er 5:1 til 1:5.
11.
Fremgangsmåte ifølge krav 1, karakterisert ved at det alifatiske nitroksydet er bis(l-oksyl-2,2,6,6-tetrametylpiperidin-4-yl)sebakat, det aromatiske aminet er N,N'-di(l,4-dimetylpentyl)fenylendiamin og den fenoliske antioksydanten er metyl 3,5-di-tert-butyl-4-hydroksyhydrocinnamat.
12.
Sammensetning stabilisert mot oksydativ nedbrytning og mot dannelsen av gummirester eller uønskede avsetninger, karakterisert ved at den innbefatter (a) bensin, og (b) en effektiv stabiliserende mengde av en synergistisk blanding av en alifatisk nitroksydforbindelse og et aromatisk amin eller en fenolisk antioksydant eller blanding av aromatisk amin og fenolisk antioksydant.
13.
Sammensetning ifølge krav 12, karakterisert ved at bensinen er pyrolyse-eller "coker" bensin.
14.
Anvendelse av en synergistisk blanding av en alifatisk nitroksydforbindelse og et aromatisk amin eller en fenolisk antioksydant eller blanding av aromatisk amin og fenolisk antioksydant for stabilisering av bensin mot oksydativ nedbrytning og mot dannelsen av gummirest eller uønskede avsetninger.
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| US08/678,165 US5711767A (en) | 1996-07-11 | 1996-07-11 | Stabilizers for the prevention of gum formation in gasoline |
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| US1940445A (en) * | 1929-08-07 | 1933-12-19 | Du Pont | Gum inhibitor for gasoline |
| 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 |
| FR1360030A (fr) * | 1962-06-13 | 1964-04-30 | American Cyanamid Co | Procédé de préparation de nitroxydes cycliques et composés obtenus |
| FR1325521A (fr) * | 1962-06-20 | 1963-04-26 | American Cyanamid Co | Nouveaux dérivés oxygénés nu,nu-disubstitués par des groupes tertiaires et procédés pour les préparer |
| US3322520A (en) * | 1964-03-23 | 1967-05-30 | Eastman Kodak Co | Gasoline inhibitor |
| US3556748A (en) * | 1966-07-05 | 1971-01-19 | Universal Oil Prod Co | Antioxidant mixture of n-phenyl-n'-sec-alkyl-ortho-phenylene-diamine and n,n'-di-sec-alkyl-ortho-phenylenediamine,and use thereof |
| GB1316342A (en) * | 1970-03-07 | 1973-05-09 | Ciba Geigy Uk Ltd | Diaryl nitroxides |
| GB1325775A (en) * | 1970-06-10 | 1973-08-08 | Ciba Geigy Uk Ltd | Phosphorus-containing piperidine derivatives and their use as stabilisers for polymerica material |
| DE2459331A1 (de) * | 1973-12-28 | 1975-07-10 | Ciba Geigy Ag | Pyrrolidin-dicarbonsaeuren und ihre ester als lichtstabilisatoren |
| US4616051A (en) * | 1981-05-04 | 1986-10-07 | Uniroyal Chemical Company, Inc. | Combination of phenolic antioxidant and stabilizer for use in organic material |
| US4398505A (en) * | 1981-10-22 | 1983-08-16 | Standard Oil Company (Indiana) | Diesel fuel composition |
| GB8332797D0 (en) * | 1983-12-08 | 1984-01-18 | Ciba Geigy Ag | Antioxidant production |
| US4670131A (en) * | 1986-01-13 | 1987-06-02 | Exxon Chemical Patents Inc. | Method for controlling fouling of hydrocarbon compositions containing olefinic compounds |
| US4648885A (en) * | 1986-06-13 | 1987-03-10 | Betz Laboratories, Inc. | Process and composition for stabilized distillate fuel oils |
| US5246469A (en) * | 1986-07-25 | 1993-09-21 | The Commonwealth Of Australia | Fuel stabilization |
| US5290888A (en) * | 1990-07-20 | 1994-03-01 | Ciba-Geigy Corporation | Process for stabilizing ethylenically unsaturated compounds and stabilized monomer compositions |
| GB9114237D0 (en) * | 1991-07-02 | 1991-08-21 | Exxon Chemical Patents Inc | Fuel oil treatment |
| US5169410A (en) * | 1991-09-24 | 1992-12-08 | Betz Laboratories, Inc. | Methods for stabilizing gasoline mixtures |
| US5136103A (en) * | 1991-09-30 | 1992-08-04 | Shell Oil Company | Process for the preparation of ketones |
| US5169401A (en) * | 1991-12-20 | 1992-12-08 | Zimmer, Inc. | Surgical reamer assembly |
| US5254760A (en) * | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| US5322960A (en) * | 1993-04-15 | 1994-06-21 | Nippon Shokubai Co., Ltd. | Method for inhibiting polymerization of (meth) acrylic acid and esters thereof |
| IT1264946B1 (it) * | 1993-07-16 | 1996-10-17 | Ciba Geigy Spa | Derivati del 2,2,6,6-tetrametil-4-piperidinolo utili come stabilizzanti alla luce ed all'ossidazione per materiali organici. |
| US5412047A (en) * | 1994-05-13 | 1995-05-02 | Xerox Corporation | Homoacrylate polymerization processes with oxonitroxides |
| US5509944A (en) * | 1994-08-09 | 1996-04-23 | Exxon Chemical Patents Inc. | Stabilization of gasoline and gasoline mixtures |
| US5495045A (en) * | 1994-12-22 | 1996-02-27 | Shell Oil Company | Process for the preparation of alkoxyalkanoic acids |
-
1996
- 1996-07-11 US US08/678,165 patent/US5711767A/en not_active Expired - Lifetime
-
1997
- 1997-07-02 EP EP97810426A patent/EP0818526B1/en not_active Expired - Lifetime
- 1997-07-02 ES ES97810426T patent/ES2190515T3/es not_active Expired - Lifetime
- 1997-07-02 DE DE69718969T patent/DE69718969T2/de not_active Expired - Lifetime
- 1997-07-07 SG SG1997002375A patent/SG50028A1/en unknown
- 1997-07-09 RU RU97111833/04A patent/RU2174998C2/ru not_active IP Right Cessation
- 1997-07-09 CZ CZ19972177A patent/CZ295427B6/cs not_active IP Right Cessation
- 1997-07-09 SK SK940-97A patent/SK284713B6/sk not_active IP Right Cessation
- 1997-07-09 CA CA002210055A patent/CA2210055C/en not_active Expired - Fee Related
- 1997-07-10 CN CN971146608A patent/CN1064992C/zh not_active Expired - Fee Related
- 1997-07-10 NO NO19973218A patent/NO318504B1/no not_active IP Right Cessation
- 1997-07-10 JP JP20090297A patent/JP3843380B2/ja not_active Expired - Fee Related
- 1997-07-10 KR KR1019970031868A patent/KR100476032B1/ko not_active IP Right Cessation
- 1997-07-10 ZA ZA9706130A patent/ZA976130B/xx unknown
- 1997-07-11 BR BR9703956A patent/BR9703956A/pt not_active IP Right Cessation
- 1997-07-11 TW TW086109881A patent/TW399091B/zh not_active IP Right Cessation
- 1997-12-07 SA SA97180688A patent/SA97180688B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW399091B (en) | 2000-07-21 |
| ZA976130B (en) | 1998-01-12 |
| CN1172149A (zh) | 1998-02-04 |
| DE69718969D1 (de) | 2003-03-20 |
| BR9703956A (pt) | 1998-11-03 |
| CZ217797A3 (cs) | 1998-02-18 |
| SK284713B6 (sk) | 2005-09-08 |
| DE69718969T2 (de) | 2003-07-17 |
| NO973218D0 (no) | 1997-07-10 |
| SG50028A1 (en) | 1998-06-15 |
| US5711767A (en) | 1998-01-27 |
| SK94097A3 (en) | 1998-01-14 |
| KR100476032B1 (ko) | 2005-07-04 |
| NO973218L (no) | 1998-01-12 |
| CN1064992C (zh) | 2001-04-25 |
| ES2190515T3 (es) | 2003-08-01 |
| JPH1077486A (ja) | 1998-03-24 |
| JP3843380B2 (ja) | 2006-11-08 |
| EP0818526B1 (en) | 2003-02-12 |
| KR980009429A (ko) | 1998-04-30 |
| CA2210055A1 (en) | 1998-01-11 |
| RU2174998C2 (ru) | 2001-10-20 |
| SA97180688B1 (ar) | 2006-04-04 |
| CA2210055C (en) | 2001-05-01 |
| CZ295427B6 (cs) | 2005-08-17 |
| EP0818526A1 (en) | 1998-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |