AU2004259773B2 - Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels - Google Patents
Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels Download PDFInfo
- Publication number
- AU2004259773B2 AU2004259773B2 AU2004259773A AU2004259773A AU2004259773B2 AU 2004259773 B2 AU2004259773 B2 AU 2004259773B2 AU 2004259773 A AU2004259773 A AU 2004259773A AU 2004259773 A AU2004259773 A AU 2004259773A AU 2004259773 B2 AU2004259773 B2 AU 2004259773B2
- Authority
- AU
- Australia
- Prior art keywords
- fatty acid
- esters
- monoalkyl esters
- acid monoalkyl
- fatty acids
- 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.)
- Ceased
Links
- 150000004665 fatty acids Chemical class 0.000 title claims description 58
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 52
- 239000000194 fatty acid Substances 0.000 title claims description 52
- 229930195729 fatty acid Natural products 0.000 title claims description 52
- 239000002283 diesel fuel Substances 0.000 title claims description 30
- 150000002148 esters Chemical class 0.000 title claims description 30
- 239000005864 Sulphur Substances 0.000 title claims 3
- 239000000314 lubricant Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 27
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 21
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 14
- 125000002346 iodo group Chemical group I* 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000005205 dihydroxybenzenes Chemical class 0.000 claims description 7
- 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 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 2
- 235000019871 vegetable fat Nutrition 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000005907 alkyl ester group Chemical group 0.000 description 11
- 239000000446 fuel Substances 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000003225 biodiesel Substances 0.000 description 9
- 235000019482 Palm oil Nutrition 0.000 description 8
- 239000002540 palm oil Substances 0.000 description 8
- 238000005299 abrasion Methods 0.000 description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
- 239000005642 Oleic acid Substances 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- 239000008157 edible vegetable oil Substances 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- -1 polycyclic aromatic compounds Chemical class 0.000 description 6
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 5
- 235000021360 Myristic acid Nutrition 0.000 description 5
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 5
- 235000021314 Palmitic acid Nutrition 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 238000001640 fractional crystallisation Methods 0.000 description 5
- 235000020778 linoleic acid Nutrition 0.000 description 5
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 5
- 230000001050 lubricating effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 239000010499 rapseed oil Substances 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- 235000019737 Animal fat Nutrition 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 2
- 239000002551 biofuel Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0119403A AT504745B1 (de) | 2003-07-28 | 2003-07-28 | Schwefelarmer dieseltreibstoff sowie verwendung von fettsäuremonoalkylestern als schmierfähigkeitsverbesserer für schwefelarme dieseltreibstoffe |
| ATA1194/2003 | 2003-07-28 | ||
| PCT/AT2004/000214 WO2005010130A1 (de) | 2003-07-28 | 2004-06-22 | Schwefelarmer dieseltreibstoff sowie verwendung von fettsäuremonoalkylestern als schmierfähigkeitsverbesserer für schwefelarme dieseltreibstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004259773A1 AU2004259773A1 (en) | 2005-02-03 |
| AU2004259773B2 true AU2004259773B2 (en) | 2010-02-11 |
Family
ID=34085018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004259773A Ceased AU2004259773B2 (en) | 2003-07-28 | 2004-06-22 | Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060213118A1 (zh) |
| EP (1) | EP1648984A1 (zh) |
| CN (1) | CN1860209B (zh) |
| AT (1) | AT504745B1 (zh) |
| AU (1) | AU2004259773B2 (zh) |
| CA (1) | CA2533657A1 (zh) |
| HK (1) | HK1097567A1 (zh) |
| NZ (1) | NZ545545A (zh) |
| WO (1) | WO2005010130A1 (zh) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1674552A1 (en) * | 2004-12-24 | 2006-06-28 | Shell Internationale Researchmaatschappij B.V. | Fuel compositions |
| MY142383A (en) * | 2005-06-10 | 2010-11-30 | Malaysian Palm Oil Board Mpob | Palm- based biodiesel formulation |
| FR2894978B1 (fr) | 2005-12-21 | 2012-06-08 | Total France | Composant ameliorant de cetane pour carburants diesels et carburants diesel le contenant |
| FR2894977A1 (fr) * | 2005-12-21 | 2007-06-22 | Total France Sa | Composant ameliorant de cetane pour carburants diesels et carburants diesel le contenant |
| FR2912932B1 (fr) | 2007-02-23 | 2011-06-10 | Total France | Solution aqueuse pour traitement des gaz d'echappement des moteurs diesel |
| EP2175010A1 (en) * | 2008-10-10 | 2010-04-14 | Eco Air S.r.l. | Use of fatty acid esters as descaling and lubricating agents |
| CN102295961B (zh) * | 2011-07-21 | 2013-09-04 | 淄博润博化工销售有限公司 | 一种低硫柴油润滑性添加剂及其制备方法 |
| CN102311838A (zh) * | 2011-08-08 | 2012-01-11 | 华东理工大学 | 一种低硫柴油润滑添加剂及其制备方法与应用 |
| CN102977945B (zh) * | 2012-11-12 | 2015-07-08 | 黄河三角洲京博化工研究院有限公司 | 一种柴油润滑性改进剂 |
| AT513799B1 (de) | 2012-12-18 | 2020-02-15 | Mag Schell Klaus | Verfahren zur Herstellung eines Bio-Diesel-Kraftstoffes mit einem speziell ausgelegten Reaktor und quasi katalytisch wirksamer nanoskalig strukturierter Materialoberfläche des Reaktors |
| RU2642080C1 (ru) * | 2016-08-12 | 2018-01-24 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Вятский государственный университет" | Топливная композиция |
| CN107177398B (zh) * | 2017-06-07 | 2020-01-31 | 上海鑫灵精细化工有限公司 | 柴油抗磨剂及其制备方法 |
| CN112779064B (zh) * | 2019-11-11 | 2022-12-13 | 中国石油化工股份有限公司 | 一种低酸型柴油抗磨剂及其制备方法和应用 |
| US11732628B1 (en) | 2020-08-12 | 2023-08-22 | Old World Industries, Llc | Diesel exhaust fluid |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920691A (en) * | 1989-05-22 | 1990-05-01 | Fainman Morton Z | Fuel additive |
| GB9301119D0 (en) * | 1993-01-21 | 1993-03-10 | Exxon Chemical Patents Inc | Fuel composition |
| IT1270954B (it) * | 1993-07-21 | 1997-05-26 | Euron Spa | Composizione di gasolio |
| US5891203A (en) * | 1998-01-20 | 1999-04-06 | Ethyl Corporation | Fuel lubricity from blends of a diethanolamine derivative and biodiesel |
| DE10111857A1 (de) * | 2001-03-08 | 2002-09-12 | Wolfram Radig | Multifunktioneller Zusatz für entschwefelte Mineraldieselkraftstoffe |
| FI111380B (fi) * | 2001-06-08 | 2003-07-15 | Forchem Oy | Menetelmä polttoaineen apuaineen valmistamiseksi ja apuaine |
| JP5129426B2 (ja) * | 2001-09-07 | 2013-01-30 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | ディーゼル燃料、その製造及び使用方法 |
| US20040231234A1 (en) * | 2003-05-19 | 2004-11-25 | May Choo Yuen | Palm diesel with low pour point for climate countries |
-
2003
- 2003-07-28 AT AT0119403A patent/AT504745B1/de not_active IP Right Cessation
-
2004
- 2004-06-22 AU AU2004259773A patent/AU2004259773B2/en not_active Ceased
- 2004-06-22 CA CA002533657A patent/CA2533657A1/en not_active Abandoned
- 2004-06-22 WO PCT/AT2004/000214 patent/WO2005010130A1/de active Search and Examination
- 2004-06-22 EP EP04737103A patent/EP1648984A1/de not_active Ceased
- 2004-06-22 NZ NZ545545A patent/NZ545545A/en unknown
- 2004-06-22 CN CN2004800281298A patent/CN1860209B/zh not_active Expired - Fee Related
-
2006
- 2006-01-27 US US11/341,259 patent/US20060213118A1/en not_active Abandoned
-
2007
- 2007-03-09 HK HK07102628.9A patent/HK1097567A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2533657A1 (en) | 2005-02-03 |
| CN1860209B (zh) | 2010-12-15 |
| AU2004259773A1 (en) | 2005-02-03 |
| HK1097567A1 (en) | 2007-06-29 |
| AT504745B1 (de) | 2010-07-15 |
| EP1648984A1 (de) | 2006-04-26 |
| AT504745A1 (de) | 2008-07-15 |
| NZ545545A (en) | 2010-06-25 |
| US20060213118A1 (en) | 2006-09-28 |
| CN1860209A (zh) | 2006-11-08 |
| WO2005010130A1 (de) | 2005-02-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC | Change of applicant's name (sec. 104) |
Owner name: BDI-BIODIESEL INTERNATIONAL AG; MITTELBACH, MARTIN Free format text: FORMER NAME: BDI ANLAGENBAU GESELLSCHAFT M.B.H; MITTELBACH, MARTIN; KONCAR, MICHAEL |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |