AU2009292637A1 - Method for improving the oxidation stability of biodiesel as measured by the Rancimat Test - Google Patents
Method for improving the oxidation stability of biodiesel as measured by the Rancimat Test Download PDFInfo
- Publication number
- AU2009292637A1 AU2009292637A1 AU2009292637A AU2009292637A AU2009292637A1 AU 2009292637 A1 AU2009292637 A1 AU 2009292637A1 AU 2009292637 A AU2009292637 A AU 2009292637A AU 2009292637 A AU2009292637 A AU 2009292637A AU 2009292637 A1 AU2009292637 A1 AU 2009292637A1
- Authority
- AU
- Australia
- Prior art keywords
- fuel
- biodiesel
- stability
- additive
- biodiesel fuel
- 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 description 67
- 230000003647 oxidation Effects 0.000 title claims description 30
- 238000007254 oxidation reaction Methods 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 28
- 238000012360 testing method Methods 0.000 title claims description 15
- 239000000446 fuel Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 50
- 239000000654 additive Substances 0.000 claims description 39
- 230000000996 additive effect Effects 0.000 claims description 34
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical group CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 28
- 239000002283 diesel fuel Substances 0.000 claims description 22
- 239000003963 antioxidant agent Substances 0.000 claims description 20
- 230000003078 antioxidant effect Effects 0.000 claims description 18
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 150000004982 aromatic amines Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 230000006698 induction Effects 0.000 description 11
- 235000006708 antioxidants Nutrition 0.000 description 10
- 239000003925 fat Substances 0.000 description 9
- 235000019197 fats Nutrition 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- -1 nitrogen containing compound Chemical class 0.000 description 8
- 239000002516 radical scavenger Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- ABAMRJVWDHJBTI-UHFFFAOYSA-N 2-ethylhexyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OCC(CC)CCCC)CCC2OC21 ABAMRJVWDHJBTI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 239000002816 fuel additive Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 2
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 2
- 244000188595 Brassica sinapistrum Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 2
- 230000000153 supplemental effect Effects 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- RURPJGZXBHYNEM-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]propyliminomethyl]phenol Chemical compound C=1C=CC=C(O)C=1C=NC(C)CN=CC1=CC=CC=C1O RURPJGZXBHYNEM-UHFFFAOYSA-N 0.000 description 1
- NKRVGWFEFKCZAP-UHFFFAOYSA-N 2-ethylhexyl nitrate Chemical compound CCCCC(CC)CO[N+]([O-])=O NKRVGWFEFKCZAP-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 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 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 235000019519 canola oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000008162 cooking oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000010771 distillate fuel oil Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000010460 hemp oil Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000019508 mustard seed Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000003116 photochemical stabilizer Substances 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
-
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19232908P | 2008-09-17 | 2008-09-17 | |
| US61/192,329 | 2008-09-17 | ||
| PCT/US2009/005185 WO2010033201A1 (en) | 2008-09-17 | 2009-09-17 | Method for improving the oxidation stability of biodiesel as measured by the rancimat test |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2009292637A1 true AU2009292637A1 (en) | 2010-03-25 |
Family
ID=42039792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009292637A Abandoned AU2009292637A1 (en) | 2008-09-17 | 2009-09-17 | Method for improving the oxidation stability of biodiesel as measured by the Rancimat Test |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110146139A1 (env) |
| EP (1) | EP2342311B1 (env) |
| JP (1) | JP2012503040A (env) |
| AU (1) | AU2009292637A1 (env) |
| CA (1) | CA2734958A1 (env) |
| WO (1) | WO2010033201A1 (env) |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1036384A (en) | 1964-03-24 | 1966-07-20 | Du Pont | Stabilized petroleum distillate fuels boiling in the fuel oil range and additive compositions therefor |
| US3336124A (en) * | 1964-08-25 | 1967-08-15 | Du Pont | Stabilized distillate fuel oils and additive compositions therefor |
| US3490882A (en) * | 1966-08-11 | 1970-01-20 | Du Pont | Stabilized distillate fuel oils and additive compositions therefor |
| US3640692A (en) * | 1969-10-29 | 1972-02-08 | Cities Service Oil Co | Stabilized distillate hydrocarbon fuel oil compositions and additives therefor |
| CA2010183A1 (en) * | 1989-03-02 | 1990-09-02 | John G. Bostick | Middle distillate fuel having improved storage stability |
| DE69004692T2 (de) * | 1990-09-20 | 1994-03-10 | Ethyl Petroleum Additives Ltd | Kohlenwasserstoffzusammensetzungen und Zusätze dafür. |
| US6143702A (en) * | 1998-10-09 | 2000-11-07 | Exxon Research And Engineering Company | Lubricating oils of enhanced oxidation stability containing n-phenyl-naphthyl amines, or substituted derivatives of n-phenyl naphthyl amine and carbodiimide acid scavengers |
| US20060201056A1 (en) * | 2000-04-14 | 2006-09-14 | Oryxe Energy International, Inc. | Biodiesel fuel additive |
| US7479168B2 (en) * | 2003-01-31 | 2009-01-20 | Chevron U.S.A. Inc. | Stable low-sulfur diesel blend of an olefinic blend component, a low-sulfur blend component, and a sulfur-free antioxidant |
| AU2004200235B2 (en) * | 2003-01-31 | 2009-12-03 | Chevron U.S.A. Inc. | Stable olefinic, low sulfur diesel fuels |
| US7179311B2 (en) * | 2003-01-31 | 2007-02-20 | Chevron U.S.A. Inc. | Stable olefinic, low sulfur diesel fuels |
| DE102005015474A1 (de) * | 2005-04-04 | 2006-10-05 | Degussa Ag | Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel |
| US8287608B2 (en) * | 2005-06-27 | 2012-10-16 | Afton Chemical Corporation | Lubricity additive for fuels |
| US20070113467A1 (en) * | 2005-11-23 | 2007-05-24 | Novus International Inc. | Biodiesel fuel compositions having increased oxidative stability |
| MX2008008745A (es) * | 2006-01-04 | 2008-09-12 | Ciba Holding Inc | Composiciones estabilizadas de combustible biodiesel. |
| EP1847584A3 (en) * | 2006-04-21 | 2008-10-22 | Infineum International Limited | Improvements in Biofuel |
| US7964002B2 (en) * | 2006-06-14 | 2011-06-21 | Chemtura Corporation | Antioxidant additive for biodiesel fuels |
| EP2052061A4 (en) * | 2006-07-11 | 2012-01-25 | Innospec Fuel Specialties Llc | STABILIZER COMPOSITIONS FOR MIXTURES OF PETROLEUM FUELS AND RENEWABLE FUELS |
| BRPI0719687A2 (pt) * | 2006-11-27 | 2013-12-24 | Ciba Holding Inc | Composições estabilizadas de combustível biodiesel |
-
2009
- 2009-09-17 CA CA2734958A patent/CA2734958A1/en not_active Abandoned
- 2009-09-17 US US13/061,761 patent/US20110146139A1/en not_active Abandoned
- 2009-09-17 EP EP09814893.5A patent/EP2342311B1/en not_active Not-in-force
- 2009-09-17 AU AU2009292637A patent/AU2009292637A1/en not_active Abandoned
- 2009-09-17 JP JP2011526874A patent/JP2012503040A/ja active Pending
- 2009-09-17 WO PCT/US2009/005185 patent/WO2010033201A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| EP2342311A1 (en) | 2011-07-13 |
| CA2734958A1 (en) | 2010-03-25 |
| US20110146139A1 (en) | 2011-06-23 |
| EP2342311A4 (en) | 2012-04-18 |
| EP2342311B1 (en) | 2016-03-09 |
| WO2010033201A1 (en) | 2010-03-25 |
| JP2012503040A (ja) | 2012-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |