US20060218855A1 - Method of increasing the oxidation stability of biodiesel - Google Patents

Method of increasing the oxidation stability of biodiesel Download PDF

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Publication number
US20060218855A1
US20060218855A1 US11/384,241 US38424106A US2006218855A1 US 20060218855 A1 US20060218855 A1 US 20060218855A1 US 38424106 A US38424106 A US 38424106A US 2006218855 A1 US2006218855 A1 US 2006218855A1
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United States
Prior art keywords
tert
butyl
biodiesel
methylphenol
butylphenol
Prior art date
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Abandoned
Application number
US11/384,241
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English (en)
Inventor
Hark-Oluf Asbahr
Thomas Bomba
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Evonik Operations GmbH
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Degussa GmbH
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Filing date
Publication date
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Assigned to DEGUSSA AG reassignment DEGUSSA AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ASBAHR, HARK-OLUF, BOMBA, THOMAS
Publication of US20060218855A1 publication Critical patent/US20060218855A1/en
Abandoned 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

Definitions

  • the invention relates to a method of increasing the oxidation stability of biodiesel.
  • the invention also includes the oxidation-stabilized produced thereby.
  • biodiesel which comprises monoalkyl esters of vegetable oils, animal fats and also used cooking fats.
  • Biodiesel is obtained by transesterification of oils, for example rapeseed oil, soybean oil or sunflower oil and also used cooking oils, with an alcohol in the presence of a catalyst.
  • Biodiesel Since the importance of biodiesel as an alternative diesel fuel for passenger cars has been continually increasing in importance in recent times, the production of biodiesel has also increased to a corresponding extent in recent years.
  • Biodiesel has a high content of unsaturated fatty acid esters which can easily be oxidized by atmospheric oxygen. The products formed (including acids, resins) can lead to corrosion and blockages in injection pumps and/or fuel lines.
  • the increasing use of the alternative biodiesel as automobile fuel has led to a need for oxidation-stabilized biodiesel. According to the prior art, preference is given to adding 2,6-di-tert-butyl-4-methylphenol (BHT) as primary antioxidant to the biodiesel in order to meet the oxidation stability requirements of the standard DIN EN 14214.
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • 2,6-di-tert-butyl-4-methylphenol as antioxidant is described in the European patent EP 0 189 049.
  • 2,6-di-tert-butyl-4-methylphenol in amounts of from 10 to 100 ppm as exclusive stabilizer in methyl esters of palm kernel oil having from 12 to 18 carbon atoms in the fatty acid is described.
  • DE 102 52 715 describes a method of increasing the storage stability of biodiesel, in which a liquid stock solution containing from 15 to 60% by weight of 2,4-di-tert-butyl-hydroxytoluene dissolved in biodiesel is added to the biodiesel to be stabilized to give a concentration of from 0.005 to 2% by weight of 2,4-di-tert-butylhydroxytoluene, based on the total solution in biodiesel.
  • the primary antioxidant used in the method of the invention has a low melting point, i.e. a melting point of less than or equal to 40° C. Owing to its low melting point, this primary antioxidant can, in the method of the invention, be mixed as liquid directly into the biodiesel without this primary antioxidant firstly having to be dissolved in a solvent, for example alcohol, or in biodiesel. Thus, the preparation of a masterbatch of this primary antioxidant in biodiesel can be dispensed with.
  • the masterbatches are generally prepared using the biodiesel for which the masterbatch is ready to be used.
  • the primary antioxidant used in the method of the invention thus leads to low production costs for the oxidation-stabilized biodiesel, since, firstly, the preparation of solutions or masterbatches comprising the active ingredient primary antioxidant can be dispensed with and, secondly, the present method shows that a product mixture from the manufacturing process of substituted alkylphenols can be used without complicated separation and purification steps.
  • a further advantage of the method of the invention is that the production of the oxidation-stabilized biodiesel can be carried out at low temperatures and within a relatively short time.
  • the method of the invention thus makes it possible to improve the economics of the production of oxidation-stabilized biodiesel.
  • the active content of the liquid primary antioxidant used according to the present invention is 100% compared to 20% of the liquid primary antioxidants according to the prior art, since the liquid generally contains only about 20% by weight of the active ingredient antioxidant.
  • the use of a liquid primary antioxidant according to the method of the invention likewise enables transport and storage costs to be saved as a result of the high active content of primary antioxidant per liter.
  • the use of a liquid primary antioxidant according to the method of the invention also leads to reduced crystallization of the primary antioxidant in the biodiesel or in plant components at low temperatures.
  • the present invention provides a method of increasing the oxidation stability of biodiesel, which comprises adding a primary antioxidant having a melting point of less than or equal to 40° C. to the biodiesel to be stabilized in an amount of from 10 to 20 000 ppm (w/w), where the primary antioxidant comprises at least one compound having the structure where:
  • the invention further provides for the use of a primary antioxidant which has a melting point of less than or equal to 40° C. and comprises at least one compound having the structure where:
  • the invention likewise provides an oxidation-stabilized biodiesel comprising from 10 to 20 000 ppm (w/w) of a primary antioxidant which has a melting point of less than or equal to 40° C. and comprises at least one compound having the structure where:
  • the inventive method of increasing the oxidation stability of biodiesel comprises adding a primary antioxidant having a melting point or less than or equal to 40° C. to the biodiesel to be stabilized in an amount of from 10 to 20 000 ppm (w/w), where the primary antioxidant comprises at least one compound having the structure where:
  • primary antioxidants are compounds or mixtures of compounds which inhibit or prevent undesirable degradation reactions in the biodiesel caused by oxygen.
  • the mode of action of these primary antioxidants in the biodiesel is described in the following reaction scheme, where R and R′ are each an organic radical and AOH is a primary antioxidant used in the method of the invention.
  • the primary antioxidant used in the method of the invention comprises neither organic solvents, for example alcohols, nor biodiesel, as is the case, for example, when a masterbatch is employed.
  • the primary antioxidant used therefore preferably comprises exclusively alkylphenols and/or substituted alkylphenols.
  • a mixture comprising various substituted and/or unsubstituted alkylphenols, preferably a mixture comprising from 0.1 to 99.9% by weight, preferably from 50 to 99% by weight and particularly preferably from 55 to 90% by weight, of one or more compounds having the structure I, is used as primary antioxidant in the method of the invention.
  • This mixture has the advantage that it comprises exclusively compounds having the structure I which all have an oxidation-stabilizing action on biodiesel.
  • a primary antioxidant comprising at least one compound having the structure II where:
  • a primary antioxidant comprising at least one compound having the structure III to the biodiesel in the method of the invention.
  • a primary antioxidant comprising at least one compound having the structure IV to the biodiesel in the method of the invention.
  • the primary antioxidant used in the method of the invention can comprise exclusively compounds selected from among
  • Pure substances or mixtures which are or comprise compounds having the structures I to IV and have a melting point of greater than 40° C. are excluded from the present invention.
  • the primary antioxidant used in the method of the invention has a melting point of ⁇ 40° C., preferably ⁇ 39° C. and particularly preferably ⁇ 38° C.
  • Secondary antioxidants which can be used in the method of the invention are alkylthiomethylphenols, preferably selected from among
  • biodiesel encompasses all the saturated and/or unsaturated alkyl esters of fatty acids, in particular methyl or ethyl esters of fatty acids, which can be used as energy carriers.
  • energy carriers include both fuels as sources of heat, for example heating material, and fuels for powering vehicles, for example automobiles, goods vehicles, ships or aircraft.
  • the biodiesel to which the method of the invention is applied is preferably a biodiesel which is usually marketed under the name biodiesel for use as automobile fuel.
  • the biodiesel to which the method of the invention is applied comprises C 12 -C 24 fatty acid alkyl esters, preferably C 12 -C 24 fatty acid methyl esters or C 12 -C 24 fatty acid ethyl esters, which can be present in pure form or as a mixture.
  • the biodiesel to which the method of the invention is applied can further comprise all customary additives such as secondary antioxidants, antifoams, low-temperature flow improvers.
  • the method of the invention is preferably applied to biodiesel produced from vegetable and/or animal oils by a process of transesterification with an alcohol, preferably methanol or ethanol, particularly preferably methanol.
  • the method of the invention is more preferably applied to biodiesel comprising transesterification products of rapeseed oil, soybean oil, sunflower oil, palm kernel oil, coconut oil, jatropha oil, cotton seed oil, peanut oil, maize oil and/or used cooking oils.
  • biodiesel which is obtained from rapeseed oil, sunflower oil or soybean oil by means of the abovementioned transesterification.
  • the method of the invention can also be applied to mixtures of the transesterification products of various vegetable and/or animal oils.
  • mixtures of saturated and/or unsaturated fatty acid alkyl esters with liquid energy carriers can be used as biodiesel.
  • liquid energy carriers for example mineral diesel fuel or heating oil
  • the oxidation-stabilized biodiesel can be added in an amount of from 0.1 to 99.9% by volume, in particular from 1 to 20% by volume, preferably from 2 to 10% by volume and more preferably from 3 to 5% by volume, to a liquid energy carrier, in particular mineral diesel fuel or heating oil.
  • a liquid energy carrier in particular mineral diesel fuel or heating oil.
  • the primary antioxidant is preferably added directly, in particular in an amount of from 10 to 20 000 ppm (w/w), preferably from 50 to 12 000 ppm (w/w) and more preferably from 100 to 8000 ppm (w/w).
  • direct addition means that no preparation of a solution or a masterbatch of the primary antioxidant has been carried out in a preceding step.
  • secondary antioxidants can also be added in an amount of from 10 to 20 000 ppm (w/w), preferably from 50 to 12 000 ppm (w/w) and preferably from 100 to 8000 ppm (w/w), to the biodiesel.
  • the primary antioxidant is preferably dissolved in the biodiesel with stirring at a temperature of from 18° C. to 60° C., more preferably from 20° C. to 40° C.
  • the invention further provides for the use of a primary antioxidant which has a melting point of less than or equal to 40° C. and comprises at least one compound having the structure I for increasing the oxidation stability of biodiesel.
  • a mixture comprising exclusively compounds having the structure I as primary antioxidant.
  • This mixture has the advantage that it comprises exclusively compounds having the structure I which all have an oxidation-stabilizing action on biodiesel.
  • Preference is given to using a primary antioxidant comprising at least one compound having the structure II.
  • a primary antioxidant comprising at least one compound having the structure III.
  • a primary antioxidant comprising at least one compound having the structure IV.
  • Pure substances or mixtures which are or comprise compounds having the structures I to IV and have a melting point of greater than 40° C. are excluded from the present invention.
  • the oxidation-stabilized biodiesel of the invention comprises from 10 to 20 000 ppm (w/w), preferably from 50 to 12 000 ppm (w/w) and more preferably from 100 to 8000 ppm (w/w), of a primary antioxidant which has a melting point of less than or equal to 40° C. and comprises at least one compound having the structure I.
  • the primary antioxidant of the oxidation-stabilized biodiesel of the invention therefore preferably comprises exclusively alkyphenols and/or substituted alkylphenols.
  • the oxidation-stabilized biodiesel of the invention comprises a mixture of various substituted and/or unsubstituted alkylphenols as primary antioxidant.
  • the biodiesel of the present invention preferably comprises a primary antioxidant comprising from 0.1 to 99.9% by weight, more preferably from 50 to 99% by weight and particularly preferably from 55 to 99% by weight, of one or more compounds having the structure I.
  • the biodiesel of the invention particularly preferably comprises a mixture comprising exclusively compounds having the structure I as primary antioxidant.
  • the biodiesel of the invention preferably comprises a primary antioxidant comprising at least one compound having the structure II.
  • the biodiesel of the invention more preferably comprises a primary antioxidant comprising at least one compound having the structure III.
  • the biodiesel of the invention particularly preferably comprises a primary antioxidant comprising at least one compound having the structure IV.
  • biodiesel of the invention can comprise a primary antioxidant comprising exclusively compounds selected from among
  • the biodiesel of the invention comprises C 12 -C 24 fatty acid alkyl esters, preferably C 12 -C 24 fatty acid methyl esters or C 12 -C 24 fatty acid ethyl esters, which can be present in pure form or as a mixture.
  • the biodiesel of the invention can further comprise all customary additives such as secondary antioxidants, antifoams.
  • the biodiesel of the invention preferably comprises transesterification products of rapeseed oil, soybean oil, sunflower oil, palm kernel oil, coconut oil, jatropha oil and/or used cooking oils.
  • the biodiesel of the invention particularly preferably comprises transesterification products obtained from rapeseed oil, sunflower oil or soybean oil by transesterification.
  • the biodiesel of the invention can also comprise mixtures of transesterification products of various vegetable and/or animal oils.
  • biodiesel of the invention can further comprise all customary additives such as secondary antioxidants, antifoams, low-temperature flow improvers.
  • Secondary antioxidants which can be present in the biodiesel of the invention are alkylthio-methylphenols, preferably selected from among
  • These secondary antioxidants can be present in an amount of from 10 to 20 000 ppm (w/w), preferably from 50 to 12 000 ppm (w/w) and more preferably from 100 to 8000 ppm (w/w), in the biodiesel of the invention.
  • the biodiesel of the invention is preferably produced using the method of the invention.
  • the primary antioxidant is dissolved in biodiesel at 20° C. with stirring, and stirring is continued until a clear solution of the primary antioxidant in the biodiesel is obtained.
  • the primary antioxidants used, the biodiesel used and the ratios are shown in Table 1.
  • the active content has been set to 20% g/l, so that 1 l of BAYNOX corresponds to 200 g of active ingredient. Analysis showed that the active ingredient in BAYNOX is 2,6-di-tert-butyl-4-hydroxytoluene.

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  • 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)
  • Water Supply & Treatment (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Public Health (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)
US11/384,241 2005-04-04 2006-03-21 Method of increasing the oxidation stability of biodiesel Abandoned US20060218855A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005015474.3 2005-04-04
DE102005015474A DE102005015474A1 (de) 2005-04-04 2005-04-04 Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel

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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)

Cited By (7)

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US20080127550A1 (en) * 2006-11-27 2008-06-05 Natalie Li Stabilized biodiesel fuel compositions
WO2008084251A1 (en) * 2007-01-11 2008-07-17 Innospec Limited Composition, method and use
WO2008144097A1 (en) 2007-05-17 2008-11-27 Baker Hughes Incorporated Method for improving biodiesel fuel
US20090139135A1 (en) * 2007-11-30 2009-06-04 Baker Hughes Incorporated Stabilization of Fatty Oils and Esters with Alkyl Phenol Amine Aldehyde Condensates
EP2302020A1 (en) 2007-07-28 2011-03-30 Innospec Limited Use of additives for improving oxidation stability of a fuel oil composition
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
EP2500402A1 (en) * 2011-03-18 2012-09-19 Otkrytoe Aktsionernoe Obschestvo "Sterlitamaxky Neftekhimichesky Zadov" Antioxidant additive composition, a solution thereof, and a method for improving the storage stability of biodiesel fuel (variants)

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CN101688137A (zh) * 2007-03-28 2010-03-31 雅宝公司 脂肪酸甲酯(生物柴油)的抗氧化剂混合物
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
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
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
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
US20120124896A1 (en) 2009-06-26 2012-05-24 Research Institute Of Petroleum Processing, Sinopec Diesel Composition and Method of Increasing Biodiesel Oxidation Stability
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
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

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