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EP1736528A3 - Process for increasing the oxidative stability of biodiesel. - Google Patents

Process for increasing the oxidative stability of biodiesel. Download PDF

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Publication number
EP1736528A3
EP1736528A3 EP06101504A EP06101504A EP1736528A3 EP 1736528 A3 EP1736528 A3 EP 1736528A3 EP 06101504 A EP06101504 A EP 06101504A EP 06101504 A EP06101504 A EP 06101504A EP 1736528 A3 EP1736528 A3 EP 1736528A3
Authority
EP
European Patent Office
Prior art keywords
biodiesel
increasing
hydrogen
alkyl group
linear alkyl
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.)
Withdrawn
Application number
EP06101504A
Other languages
German (de)
French (fr)
Other versions
EP1736528A2 (en
Inventor
Hark-Oluf Asbahr
Thomas Bomba
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Degussa GmbH filed Critical Degussa GmbH
Publication of EP1736528A2 publication Critical patent/EP1736528A2/en
Publication of EP1736528A3 publication Critical patent/EP1736528A3/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—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
    • 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
    • C10L1/192—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)

Abstract

Die Erfindung betrifft ein Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel, das sich dadurch auszeichnet, dass ein primäres Antioxidants mit einem Schmelzpunkt kleiner gleich 40°C zu dem zu stabilisierenden Biodiesel in einer Menge von 10 bis 20000 ppm (w/w) zugegeben wird, wobei das primäre Antioxidants zumindest eine Verbindung gemäß der Struktur

Figure imga0001
mit:
R1, R2 = Wasserstoff, lineare Alkylgruppe mit einer Kohlenstoffanzahl von 1 bis 20
oder
Figure imga0002
 wobei * für ein Kohlenstoffatom des aromatischen Ringssystems steht,
R3, R5 = Wasserstoff, lineare Alkylgruppe mit einer Kohlenstoffanzahl von 1 bis 20,
R4 = Wasserstoff, lineare Alkylgruppe mit einer Kohlenstoffanzahl von 1 bis 40,
wobei sowohl die Substituenten vom Typ R1 und R2 als auch vom Typ R3 und R5 gleich oder verschieden sind, aufweist.The invention relates to a process for increasing the oxidation stability of biodiesel, which is characterized in that a primary antioxidant having a melting point of less than or equal to 40 ° C. is added to the biodiesel to be stabilized in an amount of 10 to 20,000 ppm (w / w), wherein the primary antioxidant comprises at least one compound according to the structure
Figure imga0001
 With:
R 1 , R 2 = hydrogen, linear alkyl group having a carbon number of 1 to 20
or
Figure imga0002
 where * is a carbon atom of the aromatic ring system,
R 3 , R 5 = hydrogen, linear alkyl group having a carbon number of 1 to 20,
R 4 = hydrogen, linear alkyl group with a carbon number of 1 to 40,
wherein both the substituents of the type R 1 and R 2 and of the type R 3 and R 5 are identical or different.

EP06101504A 2005-04-04 2006-02-10 Process for increasing the oxidative stability of biodiesel. Withdrawn EP1736528A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102005015474A DE102005015474A1 (en) 2005-04-04 2005-04-04 Method for increasing oxidation stability of biodiesel, comprises adding a phenyl compound as primary antioxidant to the biodiesel

Publications (2)

Publication Number Publication Date
EP1736528A2 EP1736528A2 (en) 2006-12-27
EP1736528A3 true EP1736528A3 (en) 2007-01-10

Family

ID=36645651

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06101504A Withdrawn EP1736528A3 (en) 2005-04-04 2006-02-10 Process for increasing the oxidative stability of biodiesel.

Country Status (12)

Country Link
US (1) US20060218855A1 (en)
EP (1) EP1736528A3 (en)
JP (1) JP2006283028A (en)
KR (1) KR20060106903A (en)
CN (1) CN1847369A (en)
AR (1) AR054335A1 (en)
AU (1) AU2006201342A1 (en)
BR (1) BRPI0601216A (en)
CA (1) CA2541591A1 (en)
DE (1) DE102005015474A1 (en)
NZ (1) NZ546249A (en)
SG (1) SG126070A1 (en)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2670065A1 (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
CN101688137A (en) * 2007-03-28 2010-03-31 雅宝公司 The antioxidant blends of fatty acid methyl ester (biofuel)
AU2008237487B2 (en) * 2007-04-04 2012-04-05 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 (en) * 2007-07-05 2010-05-19 中国农业科学院油料作物研究所 A kind of biodiesel improver and preparation method thereof
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 (en) * 2008-06-30 2013-11-06 中国石油化工股份有限公司 Diesel composition and application of phenolic amide and/or phenolic ester as antioxidant
CN101314730B (en) * 2008-07-15 2013-02-27 中国林业科学研究院林产化学工业研究所 Ultrasonic-assisted preparation and application method of antioxidant preformed liquid for biodiesel
US20110146139A1 (en) * 2008-09-17 2011-06-23 Marc-Andre Poirier Method for improving the oxidation stability of biodiesel as measured by the rancimat test
CN101768483B (en) * 2008-12-29 2013-03-06 中国石油化工股份有限公司 Diesel composition
CN101768481B (en) * 2008-12-29 2012-11-14 中国石油化工股份有限公司 Diesel composition
CN101768482B (en) * 2008-12-29 2012-11-14 中国石油化工股份有限公司 Diesel composition
GR1006805B (en) 2009-02-26 2010-06-16 Dorivale Holdings Limited, Biodiesel containing non-phenolic additives and thereby possesing enhanced oxidative stability and low acid number.
CN101899331B (en) * 2009-05-27 2015-01-14 中国石油化工股份有限公司 Diesel composition and method for improving oxidation stability of biodiesel
CN101928614B (en) * 2009-06-26 2013-06-26 中国石油化工股份有限公司 Diesel composite and method for improving oxidation stability of biodiesel
ES2749879T3 (en) 2009-06-26 2020-03-24 China Petroleum & Chem Corp Diesel composition and process to improve oxidation stability of biodiesel
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 (en) 2011-11-24 2013-05-29 LANXESS Deutschland GmbH Oxidation stabilised biodiesel
WO2013076266A1 (en) 2011-11-24 2013-05-30 Lanxess Deutschland Gmbh Method for producing oxidation-stabilised biodiesel
EP2896682A1 (en) 2014-01-17 2015-07-22 LANXESS Deutschland GmbH Biodiesel stabilised against oxidation
CN112755585A (en) * 2020-12-22 2021-05-07 北京元泰达环保科技有限公司 Antioxidant production method

Citations (9)

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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
GB796603A (en) * 1955-05-18 1958-06-18 Ici Ltd Improvements in and relating to inhibitors of oxidation, peroxidation and polymerisation
FR1530056A (en) * 1967-06-30 1968-06-21 Ethyl Corp Jet engine fuels
EP0626442A1 (en) * 1993-05-24 1994-11-30 The Lubrizol Corporation Pour point depressant treated fatty acid esters as biodegradable, combustion engine fuels
US6475252B1 (en) * 1998-09-17 2002-11-05 University Of Dayton Stabilizing additive for the prevention of oxidation and peroxide formation
WO2003091365A1 (en) * 2002-04-23 2003-11-06 The Lubrizol Corporation Method of operating internal combustion engine by introducing antioxidant into combustion chamber
DE10252714A1 (en) * 2002-11-13 2004-05-27 Bayer Ag Process for improving the storage stability of biodiesel comprises addition of a mono- or di-alkylhydroxy toluene
WO2004069964A2 (en) * 2003-01-31 2004-08-19 Chevron U.S.A. Inc. Stable olefinic, low sulfur diesel fuels

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US3166509A (en) * 1963-01-09 1965-01-19 Ethyl Corp Antioxidant composition
DE3500938A1 (en) 1985-01-14 1986-07-17 Henkel KGaA, 4000 Düsseldorf STABILIZATION OF PALM CORE OIL AND PALM CORE FATTY ACID ALKYL ESTERS FOR THEIR PROCESSING TO COLOR-NEUTRAL REACTION PRODUCTS
TW276260B (en) * 1992-07-15 1996-05-21 Ciba Geigy Ag
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
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
EP1567621A2 (en) * 2002-05-23 2005-08-31 Paul H. Maubert Fuel additive composition and method for treatment of middle distillate fuels and gasoline
EP1563041B1 (en) * 2002-11-13 2008-07-02 LANXESS Deutschland GmbH Use of 2,6-di-tert.-butyl-p-cresol for increasing the storage stability of biodiesel
DE10252715A1 (en) 2002-11-13 2004-05-27 Bayer Ag Process for the improving the storage stability of biodiesel comprises addition of 2,4-di-tert-butylhydroxy toluene

Patent Citations (9)

* Cited by examiner, † Cited by third party
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
GB796603A (en) * 1955-05-18 1958-06-18 Ici Ltd Improvements in and relating to inhibitors of oxidation, peroxidation and polymerisation
FR1530056A (en) * 1967-06-30 1968-06-21 Ethyl Corp Jet engine fuels
EP0626442A1 (en) * 1993-05-24 1994-11-30 The Lubrizol Corporation Pour point depressant treated fatty acid esters as biodegradable, combustion engine fuels
US6475252B1 (en) * 1998-09-17 2002-11-05 University Of Dayton Stabilizing additive for the prevention of oxidation and peroxide formation
WO2003091365A1 (en) * 2002-04-23 2003-11-06 The Lubrizol Corporation Method of operating internal combustion engine by introducing antioxidant into combustion chamber
DE10252714A1 (en) * 2002-11-13 2004-05-27 Bayer Ag Process for improving the storage stability of biodiesel comprises addition of a mono- or di-alkylhydroxy toluene
WO2004069964A2 (en) * 2003-01-31 2004-08-19 Chevron U.S.A. Inc. Stable olefinic, low sulfur diesel fuels

Also Published As

Publication number Publication date
JP2006283028A (en) 2006-10-19
AU2006201342A1 (en) 2006-10-19
US20060218855A1 (en) 2006-10-05
EP1736528A2 (en) 2006-12-27
DE102005015474A1 (en) 2006-10-05
CN1847369A (en) 2006-10-18
CA2541591A1 (en) 2006-10-04
BRPI0601216A (en) 2006-12-05
KR20060106903A (en) 2006-10-12
AR054335A1 (en) 2007-06-20
NZ546249A (en) 2007-08-31
SG126070A1 (en) 2006-10-30

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