US20160326447A1 - Oxidation-stabilized biodiesel - Google Patents

Oxidation-stabilized biodiesel Download PDF

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US20160326447A1
US20160326447A1 US15/110,162 US201515110162A US2016326447A1 US 20160326447 A1 US20160326447 A1 US 20160326447A1 US 201515110162 A US201515110162 A US 201515110162A US 2016326447 A1 US2016326447 A1 US 2016326447A1
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weight
mixture
tert
alkylated
butyl
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Wolfgang Podesta
Axel Ingendoh
Hartwig Jordan
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Lanxess Distribution GmbH
Lanxess Deutschland GmbH
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Lanxess Distribution GmbH
Lanxess Deutschland GmbH
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Assigned to LANXESS DISTRIBUTION GMBH, LANXESS DEUTSCHLAND GMBH reassignment LANXESS DISTRIBUTION GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: INGENDOH, AXEL, JORDAN, HARTWIG, PODESTA, WOLFGANG
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/182Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1832Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/182Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1835Organic 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/185Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852Ethers; Acetals; Ketals; Orthoesters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224Amides; Imides carboxylic acid amides, imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/232Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L2200/00Components of fuel compositions
    • C10L2200/04Organic compounds
    • C10L2200/0461Fractions defined by their origin
    • C10L2200/0469Renewables or materials of biological origin
    • C10L2200/0476Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L2230/00Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/08Inhibitors
    • C10L2230/081Anti-oxidants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L2230/00Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/08Inhibitors
    • C10L2230/085Metal deactivators
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L2230/00Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/14Function and purpose of a components of a fuel or the composition as a whole for improving storage or transport of the fuel
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L2270/00Specifically adapted fuels
    • C10L2270/02Specifically adapted fuels for internal combustion engines
    • C10L2270/026Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L2290/00Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/24Mixing, stirring of fuel components

Definitions

  • the present invention relates to oxidation-stabilized biodiesel and to methods for the production thereof.
  • Biodiesel or fatty acid alkyl esters are used to an increasing extent as alternatives to conventional diesel fuel. It has become established as a regenerative and CO 2 -neutral first generation fuel.
  • the production takes place predominantly by transesterification of vegetable oils (fatty add triglycerides), such as, for example, palm oil, rapeseed oil, soybean oil or sunflower oil, with methanol or ethanol to give fatty acid methyl and ethyl esters by catalysis of bases such as NaOH, KOH, sodium methylate or potassium methylate.
  • vegetable oils fatty add triglycerides
  • methanol or ethanol to give fatty acid methyl and ethyl esters by catalysis of bases such as NaOH, KOH, sodium methylate or potassium methylate.
  • bases such as NaOH, KOH, sodium methylate or potassium methylate.
  • pure fats, mixtures thereof, as well as waste fats and animal fats of highly diverse origin and composition are also used.
  • EP-A 1736528 discloses the use of substituted alkylphenols. These are added to the biodiesel in concentrations of from 0.005 to 0.5% by weight.
  • the fatty acid oxidation is initiated and/or promoted by radical formers such as e.g. copper (I) and zinc (II). Since these metals are sometimes used in the alloys of pipelines, storage tanks and reactors of the biodiesel plants, the rate of the formation of free fatty acids is increased as a result, especially in the event of prolonged storage time and/or increased storage temperature of the fatty acid methyl esters.
  • radical formers such as copper (I) and zinc (II). Since these metals are sometimes used in the alloys of pipelines, storage tanks and reactors of the biodiesel plants, the rate of the formation of free fatty acids is increased as a result, especially in the event of prolonged storage time and/or increased storage temperature of the fatty acid methyl esters.
  • metal chelating agents such as e.g. citric acid (WO 2007/102948)
  • Standard commercial compounds are obtainable e.g. from Lanxess Distribution GmbH under the names Baynox® EU or Baynox® plus. These solids are dissolved in biodiesel, petroleum or toluene prior to application.
  • the aforementioned active ingredients are already obtainable in dissolved form on the market, such as e.g. Baynox® Solution (20% by weight BHT in biodiesel) or Baynox® plus Solution 20% by weight Baynox® plus in biodiesel) from Lanxess Distribution GmbH.
  • concentration here is limited to 20% by weight of active ingredient and below 10° C. crystallization can even start, as a result of which pipelines and sensitive instruments can be adversely affected. More highly concentrated solutions have to be heated in order to exclude a crystallization.
  • WO 2007/102948 describes more highly concentrated solutions that are stable at room temperature and consist of up to 40% by weight of the antioxidant tert-butylhydroquinone (TBHQ).
  • TBHQ tert-butylhydroquinone
  • this substance is hazardous to water and is only soluble in a comparatively expensive solvent ethylene glycol monobutyl ether.
  • these products can only be produced using a cosolvent (butyl acetate) and therefore have a comparatively low flashpoint of 40-70° C., which adversely affects safety and handling.
  • liquid formulations consist either of isomer mixtures of different phenols and therefore have fluctuating product properties, comprise phenylenediamines which make the solution dark red in color, or have other disadvantages (low flashpoint, high water hazard potential, high tendency towards crystallization, high viscosity, etc.).
  • the mono- and dialkylated hydroquinones such as e.g. 2-tert-butylhydroquinone (TBHQ) and 2,5-di-tert-butylhydroquinone are known as particularly effective antioxidants especially for polyunsaturated fatty acids, such as e.g. soybean oil (WO2009/108851).
  • TBHQ 2-tert-butylhydroquinone
  • 2,5-di-tert-butylhydroquinone are known as particularly effective antioxidants especially for polyunsaturated fatty acids, such as e.g. soybean oil (WO2009/108851).
  • TBHQ 2-tert-butylhydroquinone
  • WO2009/108851 2,5-di-tert-butylhydroquinone
  • the mixture used for this purpose should ideally have a flashpoint>60° C., preferably>7° C. and remain stable at temperatures down to ⁇ 5° C.
  • the biodiesel produced therewith should have a corrosion-inhibiting effect and protect the apparatuses used (tanks, pipelines etc.) as well as the biodiesel itself against oxidation, where even biodiesel contaminated with copper and zinc is to be stabilized effectively and without increasing the acid number.
  • oxidation-stabilized biodiesel can be produced by the addition of from 0.005 to 0.5% by weight of a mixture of:
  • C) 35-59% by weight of solvent selected from the group of aprotic amides with a chain length of C 1 -C 4 (C1) and/or cyclic ketals (C2) and/or dibasic esters with a chain length of C 4 -C 6 (C3),
  • the present invention therefore provides a method for the production of oxidation-stabilized biodiesel (fatty acid alkyl esters), according to which 0.005 to 0.5% by weight of a mixture of
  • C) 35-59% by weight of solvent selected from the group of aprotic amides with a chain length of C 2 -C 4 (C1) and/or cyclic ketals (C2) and/or dibasic esters with a chain length of C 4 -C 6 (C3),
  • biodiesel where the sum of the constituents A), B) and C) is 100% by weight, is metered into the biodiesel, and also the oxidation-stabilized biodiesel (fatty acid alkyl esters) comprising 0.005 to 0.5% by weight of a mixture of
  • C) 35-59% by weight of solvent selected from the group of the aprotic amides with a chain length of C 1 -C 4 (C1) and/or cyclic ketals (C2) and/or dibasic esters with a chain length of C 4 -C 6 (C3),
  • compositions comprising
  • C) 35-59% by weight of solvent selected from the group of the aprotic amides with a chain length of C 1 -C 4 (C1) and/or cyclic ketals (C2) and/or dibasic esters with a chain length of C 4 -C 6 (C3).
  • biodiesel is fatty acid methyl ester (FAME) and/or a fatty acid ethyl ester (FAEE).
  • FAME fatty acid methyl ester
  • FAEE fatty acid ethyl ester
  • This term encompasses the esters formed by transesterification of vegetable oils (fatty acid glycerides), such as, for example, palm oils, rapeseed oil, soybean oil or sunflower oil, and/or waste fats and/or animal fats, with methanol or ethanol to give fatty acid methyl or ethyl esters by catalysis of bases, such as NaOH, KOH, sodium methylate or potassium methylate.
  • the combination of at least one C 1 -C 4 -alkylated mono- and at least one C 1 -C 4 -alkylated bisphenol (A) is preferably a mixture comprising 2,6-di-tert-butyl-4-methylphenol (BHT) and 2,2′-methylenebis(6tert-butyl-4-methylphenol).
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • BHT 2,2′-methylenebis(6tert-butyl-4-methylphenol
  • the chelating agent is aromatic triazoles. These preferably have a pH>6 in aqueous solution. These chelating agents fulfill the task of complexing copper and zinc onto metal surfaces or in the biodiesel and of preventing an acceleration of the autoxidation chain.
  • benzotriazole or tolyltriazole is used as chelating agent.
  • the solvents used are preferably those with a flashpoint>60° C., preferably>70° C., particularly preferably>80° C., and those with a melting point ⁇ 10° C. preferably ⁇ 20° C. Furthermore, the solvents should be easy to handle and not be severely hazardous to water.
  • aprotic amides with a chain length of C 2 -C 4 and/or cyclic ketals and/or dibasic esters with a chain length of are used as solvent.
  • N,N-dimethylacetamide, N,N-dimethylpropionylamide and/or N-methylpyrrolidone are particularly preferred as aprotic amides.
  • dibasic esters with a chain length of C 4 -C 6 preferably dimethyl glutarate, dimethayl succinate and/or dimethyl adipate are.
  • preferred cyclic ketals are the reaction products of glycerol with at least one C 1 - to C 6 -aldehyde and/or the reaction products of glycerol with at least one C 3 - to C 6 -ketone, with 2,2-dimethyl-1,3-dioxolane-4-methanol being particularly preferred.
  • the ratio (weight ratio) of C 1 -C 4 -alkylated mono- to C 1 -C 4 -alkylated bisphenols is 1:10 to 2:1, particularly preferably 1:5 to 1:1.
  • the 40-60% by weight of A) additionally comprise 1.0-9% by weight, particularly preferably 3-8% by weight, of tert-butylhydroquinone.
  • the present invention likewise relates to a method for producing the mixture of the 1:0 constituents A), B) and C), and also a method for producing the composition comprising the constituents A), B) and C), according to which firstly the solvent C) is introduced, heated to at least 40° C. and then the constituents A) and optionally B) are metered in, preferably with stirring, and then the mixture is further stirred until a clear solution is formed.
  • Suitable mixing units are in principle all known stirring elements, preferably axial, radial or tangential stirring elements, as described in Wilke et al., Rhacktechnik Anlagenstechnische und apparative Kunststoffn [Stirring technology, processing and apparatus principles], Dr. Alfred Hüthig Verlag Heidelberg, 2nd edition, 1991, pages 92 to 97.
  • the present invention provides the use of the biodiesel stabilized by the method according to the invention as fuel, and also the oxidation-stabilized biodiesel comprising the constituents A), B) and C) in a fraction of from 0.005 to 0.5% by weight.
  • This oxidation-stabilized biodiesel is preferably produced by stirring in from 0.005 to 0.5% by weight of the mixture comprising the constituents A), B) and C).
  • Suitable mixing units are in principle all known stirring elements, preferably axial, radial or tangential stirring elements, as described in Wilke et al., Retztechnik Maschinenstechnische und apparative Kunststoffn [Stirring technology, processing and apparatus principles], Dr. Alfred Wilsonhig Verlag Heidelberg, 2nd edition, 1991, pages 92 to 97.
  • the Rancimat test in accordance with DIN 14112 was used (Rancimat 679 from Metrohm AG). In this, at a temperature of 110° C., air is passed through the sample, and the volatile oxidation products formed following consumption of the antioxidants present (500 or 1000 ppm) are measured via the change in conductivity. This is used to determine the induction time, i.e. the start of oxidation via the tangent method.
  • rapeseed or soybean methyl esters were provided with 1000 ppm of antioxidant (mixtures A to H) and tested as to oxidation stability by the Rancimat method (DIN 14112) at 110° C.
  • a copper strip as described in EN 2160 was hung in the bath.
  • the mixtures produced by the method according to the invention exhibit a high Rancimat value coupled with simultaneously high flashpoint, and no evident corrosion as soon as tolyltriazole was used.
  • the mixture D listed as comparison example has a comparatively low flashpoint, which considerably hinders handling and dosing.
  • the mixture F listed as comparative example likewise exhibits a low flashpoint and additionally an increased acid number on account of the chelating agent citric acid present herein. This may lead to an increase in corrosion rate.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Fats And Perfumes (AREA)
US15/110,162 2014-01-17 2015-01-07 Oxidation-stabilized biodiesel Abandoned US20160326447A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP14151687.2 2014-01-17
EP14151687.2A EP2896682A1 (de) 2014-01-17 2014-01-17 Oxidationsstabilisierter Biodiesel
PCT/EP2015/050173 WO2015106997A1 (de) 2014-01-17 2015-01-07 Oxidationsstabilisierter biodiesel

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US (1) US20160326447A1 (ru)
EP (2) EP2896682A1 (ru)
CN (1) CN106414676A (ru)
RU (1) RU2016133615A (ru)
WO (1) WO2015106997A1 (ru)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020083837A1 (fr) 2018-10-24 2020-04-30 Total Marketing Services Association d'additifs pour carburant
US20210324281A1 (en) * 2017-08-03 2021-10-21 Universität Regensburg Fuel derived from renewable resources
CN114341321A (zh) * 2019-09-10 2022-04-12 雪佛龙奥伦耐有限责任公司 通过燃料添加剂减少燃烧发动机的摩擦
US12091624B2 (en) 2021-07-06 2024-09-17 Happyfuel, Llc Fuel stabilizer

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE112016004456T5 (de) 2015-09-30 2018-07-26 Inachem Gmbh Lagerstabile Verbindungen von Antioxidantien enthaltend Ascorbinsäure

Citations (2)

* Cited by examiner, † Cited by third party
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