CA2541591A1 - Method of increasing the oxidation stability of biodiesel - Google Patents
Method of increasing the oxidation stability of biodiesel Download PDFInfo
- Publication number
- CA2541591A1 CA2541591A1 CA002541591A CA2541591A CA2541591A1 CA 2541591 A1 CA2541591 A1 CA 2541591A1 CA 002541591 A CA002541591 A CA 002541591A CA 2541591 A CA2541591 A CA 2541591A CA 2541591 A1 CA2541591 A1 CA 2541591A1
- Authority
- CA
- Canada
- Prior art keywords
- tert
- butyl
- butylphenol
- primary antioxidant
- dimethylphenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003225 biodiesel Substances 0.000 title claims abstract description 116
- 238000000034 method Methods 0.000 title claims abstract description 68
- 230000003647 oxidation Effects 0.000 title claims abstract description 14
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 14
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 136
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 120
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 238000002844 melting Methods 0.000 claims abstract description 19
- 230000008018 melting Effects 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract 8
- 239000000203 mixture Substances 0.000 claims description 39
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 claims description 27
- 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 21
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 claims description 20
- 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 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 16
- 239000000194 fatty acid Substances 0.000 claims description 16
- 229930195729 fatty acid Natural products 0.000 claims description 16
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 claims description 12
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 12
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- NPHAZMSHLCWTNE-UHFFFAOYSA-N 3-tert-butyl-2,5-dimethylphenol Chemical compound CC1=CC(O)=C(C)C(C(C)(C)C)=C1 NPHAZMSHLCWTNE-UHFFFAOYSA-N 0.000 claims description 11
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 10
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- RJKPEKIHHFNMGS-UHFFFAOYSA-N 2,4-ditert-butyl-3-methylphenol Chemical compound CC1=C(C(C)(C)C)C=CC(O)=C1C(C)(C)C RJKPEKIHHFNMGS-UHFFFAOYSA-N 0.000 claims description 8
- ZZZRZBIPCKQDQR-UHFFFAOYSA-N 2,4-ditert-butyl-6-methylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O ZZZRZBIPCKQDQR-UHFFFAOYSA-N 0.000 claims description 8
- KDBZVULQVCUNNA-UHFFFAOYSA-N 2,5-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(O)=C1 KDBZVULQVCUNNA-UHFFFAOYSA-N 0.000 claims description 8
- AFTBJQDQENGCPC-UHFFFAOYSA-N 2,5-ditert-butyl-4-methylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C=C1C(C)(C)C AFTBJQDQENGCPC-UHFFFAOYSA-N 0.000 claims description 8
- WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 claims description 7
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 claims description 7
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 claims description 6
- VQQLTEBUMLSLFJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-nonylphenol Chemical compound CCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VQQLTEBUMLSLFJ-UHFFFAOYSA-N 0.000 claims description 6
- BFZOTKYPSZSDEV-UHFFFAOYSA-N 4-butan-2-yl-2,6-ditert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BFZOTKYPSZSDEV-UHFFFAOYSA-N 0.000 claims description 6
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 claims description 6
- MEPYMUOZRROULQ-UHFFFAOYSA-N 4-tert-butyl-2,6-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1O MEPYMUOZRROULQ-UHFFFAOYSA-N 0.000 claims description 6
- SNKLPZOJLXDZCW-UHFFFAOYSA-N 4-tert-butyl-2-methylphenol Chemical compound CC1=CC(C(C)(C)C)=CC=C1O SNKLPZOJLXDZCW-UHFFFAOYSA-N 0.000 claims description 6
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 6
- 239000002283 diesel fuel Substances 0.000 claims description 6
- BGRKGHSKCFAPCL-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=CC=C1O BGRKGHSKCFAPCL-UHFFFAOYSA-N 0.000 claims description 5
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 claims description 5
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- JKFZLMPBXBMSPD-UHFFFAOYSA-N 2-butan-2-yl-4-tert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=CC=C1O JKFZLMPBXBMSPD-UHFFFAOYSA-N 0.000 claims description 4
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 claims description 4
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
- SDNVJMZXSOXXQN-UHFFFAOYSA-N 3,4-ditert-butyl-2-methylphenol Chemical compound CC1=C(O)C=CC(C(C)(C)C)=C1C(C)(C)C SDNVJMZXSOXXQN-UHFFFAOYSA-N 0.000 claims description 3
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 claims description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- JJULABXIXFRDCQ-UHFFFAOYSA-N 2,3,4-tritert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C JJULABXIXFRDCQ-UHFFFAOYSA-N 0.000 claims 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 claims 1
- FHTGJZOULSYEOB-UHFFFAOYSA-N 2,6-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC=CC(C(C)CC)=C1O FHTGJZOULSYEOB-UHFFFAOYSA-N 0.000 claims 1
- MIHQWNKDHBLQEZ-UHFFFAOYSA-N 3-tert-butyl-2-methylphenol Chemical compound CC1=C(O)C=CC=C1C(C)(C)C MIHQWNKDHBLQEZ-UHFFFAOYSA-N 0.000 claims 1
- OXPSEZLCVXHNQE-UHFFFAOYSA-N 4-tert-butyl-2,3-dimethylphenol Chemical compound CC1=C(C)C(C(C)(C)C)=CC=C1O OXPSEZLCVXHNQE-UHFFFAOYSA-N 0.000 claims 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 claims 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 13
- 238000005809 transesterification reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000019484 Rapeseed oil Nutrition 0.000 description 6
- 235000019486 Sunflower oil Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 239000002600 sunflower oil Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000000446 fuel Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004594 Masterbatch (MB) Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 3
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000008162 cooking oil Substances 0.000 description 3
- 239000003346 palm kernel oil Substances 0.000 description 3
- 235000019865 palm kernel oil Nutrition 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- -1 unsaturated fatty acid esters Chemical class 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- ZRDUANIDHBCCAO-UHFFFAOYSA-N (2,4-ditert-butylphenyl)methanol Chemical compound CC(C)(C)C1=CC=C(CO)C(C(C)(C)C)=C1 ZRDUANIDHBCCAO-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 241000221089 Jatropha Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 239000003490 Thiodipropionic acid Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 235000014541 cooking fats Nutrition 0.000 description 2
- RHMZKSWPMYAOAZ-UHFFFAOYSA-N diethyl peroxide Chemical class CCOOCC RHMZKSWPMYAOAZ-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
- 235000015073 liquid stocks Nutrition 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 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 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection 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
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Natural products C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03D—WATER-CLOSETS OR URINALS WITH FLUSHING DEVICES; FLUSHING VALVES THEREFOR
- E03D1/00—Water flushing devices with cisterns ; Setting up a range of flushing devices or water-closets; Combinations of several flushing devices
- E03D1/02—High-level flushing systems
- E03D1/14—Cisterns discharging variable quantities of water also cisterns with bell siphons in combination with flushing valves
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/182—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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03D—WATER-CLOSETS OR URINALS WITH FLUSHING DEVICES; FLUSHING VALVES THEREFOR
- E03D1/00—Water flushing devices with cisterns ; Setting up a range of flushing devices or water-closets; Combinations of several flushing devices
- E03D1/30—Valves for high or low level cisterns; Their arrangement ; Flushing mechanisms in the cistern, optionally with provisions for a pre-or a post- flushing and for cutting off the flushing mechanism in case of leakage
- E03D1/34—Flushing valves for outlets; Arrangement of outlet valves
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03D—WATER-CLOSETS OR URINALS WITH FLUSHING DEVICES; FLUSHING VALVES THEREFOR
- E03D5/00—Special constructions of flushing devices, e.g. closed flushing system
- E03D5/10—Special constructions of flushing devices, e.g. closed flushing system operated electrically, e.g. by a photo-cell; also combined with devices for opening or closing shutters in the bowl outlet and/or with devices for raising/or lowering seat and cover and/or for swiveling the bowl
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03D—WATER-CLOSETS OR URINALS WITH FLUSHING DEVICES; FLUSHING VALVES THEREFOR
- E03D1/00—Water flushing devices with cisterns ; Setting up a range of flushing devices or water-closets; Combinations of several flushing devices
- E03D1/02—High-level flushing systems
- E03D1/14—Cisterns discharging variable quantities of water also cisterns with bell siphons in combination with flushing valves
- E03D2001/147—Cisterns discharging variable quantities of water also cisterns with bell siphons in combination with flushing valves having provisions for active interruption of flushing
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Public Health (AREA)
- Water Supply & Treatment (AREA)
- Combustion & Propulsion (AREA)
- Aviation & Aerospace Engineering (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Lubricants (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005015474A DE102005015474A1 (de) | 2005-04-04 | 2005-04-04 | Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel |
| DE102005015474.3 | 2005-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2541591A1 true CA2541591A1 (en) | 2006-10-04 |
Family
ID=36645651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002541591A Abandoned CA2541591A1 (en) | 2005-04-04 | 2006-03-31 | Method of increasing the oxidation stability of biodiesel |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20060218855A1 (ja) |
| EP (1) | EP1736528A3 (ja) |
| JP (1) | JP2006283028A (ja) |
| KR (1) | KR20060106903A (ja) |
| CN (1) | CN1847369A (ja) |
| AR (1) | AR054335A1 (ja) |
| AU (1) | AU2006201342A1 (ja) |
| BR (1) | BRPI0601216A (ja) |
| CA (1) | CA2541591A1 (ja) |
| DE (1) | DE102005015474A1 (ja) |
| NZ (1) | NZ546249A (ja) |
| SG (1) | SG126070A1 (ja) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008065015A1 (en) * | 2006-11-27 | 2008-06-05 | Ciba Holding Inc. | Stabilised biodiesel fuel compositions |
| GB0700534D0 (en) * | 2007-01-11 | 2007-02-21 | Innospec Ltd | Composition |
| US20100107481A1 (en) * | 2007-03-28 | 2010-05-06 | Albemarie Corporation | Antioxidant blends for fatty acid methyl esters (biodiesel) |
| EP2132285A2 (en) * | 2007-04-04 | 2009-12-16 | The Lubrizol Corporation | A synergistic combination of a hindered phenol and nitrogen containing detergent for biodiesel fuel to improve oxidative stability |
| US7918905B2 (en) | 2007-05-17 | 2011-04-05 | Baker Hughes Incorporated | Method for improving biodiesel fuel |
| CN101082004B (zh) * | 2007-07-05 | 2010-05-19 | 中国农业科学院油料作物研究所 | 一种生物柴油改良剂及其制备方法 |
| GB0714725D0 (en) | 2007-07-28 | 2007-09-05 | Innospec Ltd | Fuel oil compositions and additives therefor |
| US8430936B2 (en) | 2007-11-30 | 2013-04-30 | Baker Hughes Incorporated | Stabilization of fatty oils and esters with alkyl phenol amine aldehyde condensates |
| WO2009108747A1 (en) * | 2008-02-27 | 2009-09-03 | Wayne State University | The effect of natural and synthetic antioxidants on the oxidative stability of biodiesel |
| CN101619246B (zh) * | 2008-06-30 | 2013-11-06 | 中国石油化工股份有限公司 | 柴油组合物以及酚酰胺和/或酚酯作为抗氧剂的用途 |
| CN101314730B (zh) * | 2008-07-15 | 2013-02-27 | 中国林业科学研究院林产化学工业研究所 | 生物柴油用抗氧化剂预制液的超声波辅助制备及使用方法 |
| CA2734958A1 (en) * | 2008-09-17 | 2010-03-25 | Exxonmobil Research And Engineering Company | Method for improving the oxidation stability of biodiesel as measured by the rancimat test |
| CN101768481B (zh) * | 2008-12-29 | 2012-11-14 | 中国石油化工股份有限公司 | 一种柴油组合物 |
| CN101768482B (zh) * | 2008-12-29 | 2012-11-14 | 中国石油化工股份有限公司 | 一种柴油组合物 |
| CN101768483B (zh) * | 2008-12-29 | 2013-03-06 | 中国石油化工股份有限公司 | 一种柴油组合物 |
| GR1006805B (el) | 2009-02-26 | 2010-06-16 | Dorivale Holdings Limited, | Βιοντιζελ που περιεχει μη φαινολικα προσθετα και ως εκ τουτου διαθετει αυξημενη οξειδωτικη σταθεροτητα και χαμηλο αριθμο οξυτητος |
| CN101899331B (zh) * | 2009-05-27 | 2015-01-14 | 中国石油化工股份有限公司 | 一种柴油组合物和提高生物柴油氧化安定性的方法 |
| CN101928614B (zh) * | 2009-06-26 | 2013-06-26 | 中国石油化工股份有限公司 | 一种柴油组合物和提高生物柴油氧化安定性的方法 |
| ES2749879T3 (es) | 2009-06-26 | 2020-03-24 | China Petroleum & Chem Corp | Composición de diésel y proceso para mejorar la estabilidad a la oxidación de biodiésel |
| US20120233912A1 (en) * | 2011-03-18 | 2012-09-20 | Otkrytoe Aktsionernoe Obschestvo "Sterlitamaxky Neftekhimichesky Zavod" | Antioxidant additive composition, a solution thereof, and a method for improving the storage stability of biodiesel fuel (variants) |
| EP2597139A1 (de) | 2011-11-24 | 2013-05-29 | LANXESS Deutschland GmbH | Oxidationsstabilisierter Biodiesel |
| WO2013076266A1 (de) | 2011-11-24 | 2013-05-30 | Lanxess Deutschland Gmbh | Verfahren zur herstellung von oxidationsstabilisiertem biodiesel |
| EP2896682A1 (de) | 2014-01-17 | 2015-07-22 | LANXESS Deutschland GmbH | Oxidationsstabilisierter Biodiesel |
| CN112755585A (zh) * | 2020-12-22 | 2021-05-07 | 北京元泰达环保科技有限公司 | 抗氧化剂生产方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2275175A (en) * | 1939-11-30 | 1942-03-03 | Standard Oil Dev Co | Motor fuel |
| GB753794A (en) * | 1953-10-07 | 1956-08-01 | Universal Oil Prod Co | Improvements in or relating to antioxidant compositions and food products stabilizedtherewith |
| NL99615C (ja) * | 1955-05-18 | |||
| US3166509A (en) * | 1963-01-09 | 1965-01-19 | Ethyl Corp | Antioxidant composition |
| FR1530056A (fr) * | 1967-06-30 | 1968-06-21 | Ethyl Corp | Carburants pour moteurs à réaction |
| DE3500938A1 (de) | 1985-01-14 | 1986-07-17 | Henkel KGaA, 4000 Düsseldorf | Stabilisierung von palmkernoel und palmkernfettsaeurealkylestern fuer deren verarbeitung zu farbneutralen reaktionsfolgeprodukten |
| TW276260B (ja) * | 1992-07-15 | 1996-05-21 | Ciba Geigy Ag | |
| AU674052B2 (en) * | 1993-05-24 | 1996-12-05 | Lubrizol Corporation, The | Pour point depressant treated fatty acid esters as biodegradable, combustion engine fuels |
| US5578090A (en) * | 1995-06-07 | 1996-11-26 | Bri | Biodiesel fuel |
| US5891203A (en) * | 1998-01-20 | 1999-04-06 | Ethyl Corporation | Fuel lubricity from blends of a diethanolamine derivative and biodiesel |
| US6475252B1 (en) * | 1998-09-17 | 2002-11-05 | University Of Dayton | Stabilizing additive for the prevention of oxidation and peroxide formation |
| US6740508B2 (en) * | 1999-02-11 | 2004-05-25 | Renessen Llc | Fermentation-based products from corn and method |
| US7208022B2 (en) * | 2002-03-14 | 2007-04-24 | The Lubrizol Corporation | Ethanol-diesel fuel composition and methods thereof |
| AU2003221899B2 (en) * | 2002-04-23 | 2008-11-27 | The Lubrizol Corporation | Method of operating internal combustion engine by introducing antioxidant into combustion chamber |
| US6923838B2 (en) * | 2002-05-23 | 2005-08-02 | Advanced Combustion Technologies, Inc. | Fuel additive composition and method for treatment of middle distillate fuels and gasoline |
| DE10252714B4 (de) | 2002-11-13 | 2007-09-13 | Lanxess Deutschland Gmbh | Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel sowie die Verwendung von Mono- oder Dialkylhydroxytoluol zur Erhöhung der Oxidationsstabilität von Biodiesel |
| DE10252715A1 (de) | 2002-11-13 | 2004-05-27 | Bayer Ag | Verfahren zur Erhöhung der Lagerstabilität von Biodiesel sowie die Verwendung von 2,4-Di-tert.-Butylhydroxytoluol zur Erhöhung der Lagerstabilität von Biodiesel |
| EP1972679B1 (de) | 2002-11-13 | 2017-05-10 | LANXESS Deutschland GmbH | Verwendung von 2,6-di-tert.-butyl-p-kresol zur erhöhung der lagerstabilität von biodiesel |
| AU2004200235B2 (en) * | 2003-01-31 | 2009-12-03 | Chevron U.S.A. Inc. | Stable olefinic, low sulfur diesel fuels |
-
2005
- 2005-04-04 DE DE102005015474A patent/DE102005015474A1/de not_active Withdrawn
-
2006
- 2006-02-10 EP EP06101504A patent/EP1736528A3/de not_active Withdrawn
- 2006-03-10 SG SG200601627A patent/SG126070A1/en unknown
- 2006-03-21 US US11/384,241 patent/US20060218855A1/en not_active Abandoned
- 2006-03-29 AR ARP060101221A patent/AR054335A1/es unknown
- 2006-03-30 AU AU2006201342A patent/AU2006201342A1/en not_active Abandoned
- 2006-03-30 NZ NZ546249A patent/NZ546249A/en unknown
- 2006-03-31 CA CA002541591A patent/CA2541591A1/en not_active Abandoned
- 2006-03-31 JP JP2006098322A patent/JP2006283028A/ja not_active Withdrawn
- 2006-04-03 CN CNA2006100719299A patent/CN1847369A/zh active Pending
- 2006-04-04 BR BRPI0601216-7A patent/BRPI0601216A/pt not_active IP Right Cessation
- 2006-04-04 KR KR1020060030620A patent/KR20060106903A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1736528A2 (de) | 2006-12-27 |
| DE102005015474A1 (de) | 2006-10-05 |
| NZ546249A (en) | 2007-08-31 |
| JP2006283028A (ja) | 2006-10-19 |
| BRPI0601216A (pt) | 2006-12-05 |
| AR054335A1 (es) | 2007-06-20 |
| US20060218855A1 (en) | 2006-10-05 |
| CN1847369A (zh) | 2006-10-18 |
| AU2006201342A1 (en) | 2006-10-19 |
| SG126070A1 (en) | 2006-10-30 |
| EP1736528A3 (de) | 2007-01-10 |
| KR20060106903A (ko) | 2006-10-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |