US20040139649A1 - Process for increasing the storgage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel - Google Patents

Process for increasing the storgage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel Download PDF

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Publication number
US20040139649A1
US20040139649A1 US10/703,263 US70326303A US2004139649A1 US 20040139649 A1 US20040139649 A1 US 20040139649A1 US 70326303 A US70326303 A US 70326303A US 2004139649 A1 US2004139649 A1 US 2004139649A1
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United States
Prior art keywords
biodiesel
bht
tert
increasing
butylhydroxytoluene
Prior art date
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Abandoned
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US10/703,263
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English (en)
Inventor
Axel Ingendoh
Christian Rother
Klaus-Peter Heise
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Lanxess Deutschland GmbH
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Individual
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32313557&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20040139649(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from DE10252715A external-priority patent/DE10252715A1/de
Priority claimed from DE10252714A external-priority patent/DE10252714B4/de
Application filed by Individual filed Critical Individual
Assigned to BAYER AKTIENGESELLSCHAFT reassignment BAYER AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEISE, KLAUS-PETER, ROTHER, CHRISTIAN, INGENDOH, AXEL
Publication of US20040139649A1 publication Critical patent/US20040139649A1/en
Assigned to LANXESS DEUTSCHLAND GMBH reassignment LANXESS DEUTSCHLAND GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYER AG
Priority to US12/157,692 priority Critical patent/US20080313956A1/en
Abandoned legal-status Critical Current

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    • 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
    • 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
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

  • the invention relates to a process for increasing the storage stability of biodiesel and more specifically, the invention relates to the use of 2,4-di-tert-butylhydroxytoluene (referred to hereinbelow as BHT) for increasing the storage stability of biodiesel.
  • BHT 2,4-di-tert-butylhydroxytoluene
  • Biodiesel which is currently being used to an increasing extent to replace petroleum diesel as a fuel for diesel engines, for combined heating and power stations, ships and boats, as well as motor vehicles.
  • Biodesel comprising of fatty acid alkyl esters, which are predominantly fatty acid methyl esters, is obtained by transesterification, in which vegetable oils such as rapeseed oil, soya oil, palm oils and other vegetable oils used in cooking oil or animal fats, are reacted with methanol in the presence of a catalyst (usually sodium hydroxide solution).
  • a catalyst usually sodium hydroxide solution
  • glycerol also obtained in addition to the fatty acid methyl esters which can be used as biodiesel.
  • biodesel is disadvantaged by its low storage stability. This is caused by the decomposition of the biodesel's high content of unsaturated fatty esters into short chain products, which reduces the energy value of this alternative fuel.
  • the decomposition leads to precipitation, which is recognizable as cloudiness of the biodiesel.
  • the resulting decomposition products are peroxides, aldehydes and short-chain free fatty acids which form soluble and insoluble polymers as precipitates.
  • the acids tend to corrode injection systems, pumps and nozzles of diesel engines.
  • the insoluble polymers when crosslinked, can block the nozzles and lead to sparingly soluble deposits. This considerably restricts the functioning of the diesel engines.
  • biodiesel In addition, soluble and insoluble polymers which are formed by oxidative degradation from the overall decomposition products cause incomplete combustion with soot formation, which can in some cases lead to engine damage. Therefore, none of these decomposition products should be present in the biodiesel. Nonetheless, the increased use of biodiesel as an alternative fuel derived from renewable raw materials makes it absolutely necessary to increase the storage stability of biodiesel.
  • BHT 2,4-di-tert-butylhydroxytoluene
  • 2,6-di-tert-butyl-p-cresol 2,6-di-tert-butyl-p-cresol
  • the present invention therefore provides a process for increasing the storage stability of biodiesel, in which a liquid stock solution, based on the stock solution, comprises 15 to 60% by weight of BHT dissolved in biodiesel is metered into the biodiesel to be stabilized up to a concentration of 0.005 to 2% by weight of BHT, based on the overall solution of biodiesel.
  • FIG. 1 is a graphical representation of the results of Rancimate test showing addition of increasing amounts of BHT and the percent content of C18 acid methyl ester in the biodiesel correlating to the ppm of BHT added.
  • FIG. 2 shows that the difference in cloudiness before (left side) and after addition of BHT (right side).
  • biodiesel refers to all saturated and unsaturated fatty acid alkyl esters, in particular fatty acid methyl esters, which can be used as biodiesel fuel, as customarily available under the name biodiesel as a fuel in automobiles for diesel engines in motor vehicles, combined heating and power plants, ships and boats, and other stationary diesel engines.
  • the fatty acid methyl esters used as biodiesel are C 14 -C 24 fatty acid methyl esters which may be pure or in a mixture.
  • the biodiesels used in the process according to the invention may additionally comprise all customary additives as used, for example, to increase the winter stability of biodiesel.
  • the biodiesels having storage stability improved by the process according to the invention are prepared by transesterification of methanol with vegetable oils such as rapeseed oil, soya oil, palm oil, used cooking oils and fats or animal fats.
  • the biodiesel which is stabilized in accordance with the invention is preferably that which has been obtained from rapeseed oil or soya oil by the transesterification mentioned above.
  • “storage stability” means reduced cloudiness of the biodiesel, said cloudiness resulting from the reaction of decomposition products formed by oxidative processes in the biodiesel, giving rise to soluble and insoluble polymers which manifest in the form of precipitation.
  • the invention further provides a process for preparing a liquid stock solution for use in increasing the storage stability of biodiesel, in which liquefied, optionally distilled, BHT is metered at a temperature in the range from 70 to 120° C., preferably 90 to 120° C., with stirring into biodiesel up to a concentration of 15 to 60% by weight of BHT, based on the stock solution.
  • BHT is a solid at room temperature and can only be metered into the biodiesel at room temperature with great difficulty.
  • the inventive stock solution comprising 15 to 60% by weight of BHT, preferably 20 to 40% by weight of BHT, is a highly concentrated solution of BHT in biodiesel which is liquid and meterable and can be very easily metered into the biodiesel to be stabilized. Even after a prolonged period, surprisingly, no precipitation of BHT out of this highly concentrated stock solution can be detected.
  • the stock solution mentioned can be metered into the biodiesel to be stabilized up to a concentration of 0.005% by weight to 2% by weight, preferably 0.1 to 1% by weight, based on the overall solution of biodiesel. It is also possible to add higher concentrations of BHT to the biodiesel. The greatest stability effects are observed up to a concentration of 2% by weight.
  • the inventively stabilized biodiesel has considerably improved storage stability, i.e., no undesired precipitation of insoluble polymers generated by oxidative degradation is detected in the inventively stabilized biodiesel.
  • BHT advantageously leads to an increase in the solidification point of the biodiesel.
  • solidification point refers to the temperature at which the biodiesel begins to crystallize out.
  • the invention further provides the use of BHT for increasing the storage stability of biodiesel by preventing the cloudiness of biodiesel as a result of the decomposition products formed by oxidation processes.
  • the cloudiness manifests itself in the form of precipitation.
  • this precipitation can now be prevented from blocking engine nozzles or generating undesired deposits in the internal engine chamber (pistons, lines) by incomplete combustion, which can lead to engine damage.
  • the invention further provides the storage-stabilized biodiesel itself which contains 0.005 to 2% by weight of dissolved BHT.
  • Biodiesel from rapeseed oil was subjected to a Rancimate test admixed with increasing amounts of BHT (trade product from Bayer AG: Baynox®).
  • the Rancimate 679 (Metrohm) consists of a control section and a wet section. In the wet section, the samples are heated and blown through by air in the presence of copper. During the oxidative ageing, short-chain, volatile organic acids are formed and are introduced into a measuring cell filled with distilled water. The conductivity is measured and recorded there continuously.
  • the end of the ageing and oxidative stability is indicated by a steep increase in the conductivity.
  • the time until the turning point is reached is referred to as the induction period and serves as a measure for the ageing stability.
  • Time 120 minutes at 70° C. while passing through 60 ml/h of air/hour.
  • FIG. 1 shows the results in graphical form.
  • a 5 l flask having a narrow neck was charged with 2 l of biodiesel, and a second flask with the same amount, but admixed with 0.05% of BHT.
  • the vessels were not sealed and left to stand at room temperature with occasional shaking (2-3 times per week). After approximately 6 weeks, the first cloudiness could be observed in the product which had not been admixed with BHT. After a further week, cloudiness as a result of insoluble polymers could be clearly seen.
  • Biodiesel was investigated using oxygen under pressure (10 bar) by the DSC method (Differential Scanning Calorimetry according to DIN No. 51007). To this end, pure biodiesel and biodiesel with increasing amounts of BHT were used in the test arrangement.
  • DSC dynamic differential scanning calorimetry
  • Comparative Example 2 biodiesel without BHT exhibited the beginning of the strongly exothermic oxidation reaction in the DSC from as low as approx. 60° C.
  • the mixture is cooled to room temperature and transferred through a filter and into a 21.5 l metal canister.
  • the 20 g/l solution exhibits no cloudiness or precipitation whatsoever even after storage at 0° C. for two weeks.
  • FIG. 2 illustrates the result

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Carbonaceous Fuels (AREA)
US10/703,263 2002-11-13 2003-11-07 Process for increasing the storgage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel Abandoned US20040139649A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/157,692 US20080313956A1 (en) 2002-11-13 2008-06-12 Process for increasing the storage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE10252715A DE10252715A1 (de) 2002-11-13 2002-11-13 Verfahren zur Erhöhung der Lagerstabilität von Biodiesel sowie die Verwendung von 2,4-Di-tert.-Butylhydroxytoluol zur Erhöhung der Lagerstabilität von Biodiesel
DE10252714.8 2002-11-13
DE10252715.6 2002-11-13
DE10252714A DE10252714B4 (de) 2002-11-13 2002-11-13 Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel sowie die Verwendung von Mono- oder Dialkylhydroxytoluol zur Erhöhung der Oxidationsstabilität von Biodiesel

Related Child Applications (1)

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US12/157,692 Continuation US20080313956A1 (en) 2002-11-13 2008-06-12 Process for increasing the storage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel

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US10/703,263 Abandoned US20040139649A1 (en) 2002-11-13 2003-11-07 Process for increasing the storgage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel
US12/157,692 Abandoned US20080313956A1 (en) 2002-11-13 2008-06-12 Process for increasing the storage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel

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US (2) US20040139649A1 (fr)
EP (2) EP1563041B1 (fr)
AT (1) ATE399834T1 (fr)
AU (1) AU2003257439A1 (fr)
DE (1) DE50310078D1 (fr)
DK (1) DK1563041T3 (fr)
ES (2) ES2629089T3 (fr)
PL (1) PL203138B1 (fr)
PT (1) PT1563041E (fr)
RU (2) RU2340655C2 (fr)
SI (1) SI1563041T1 (fr)
UA (1) UA86007C2 (fr)
WO (1) WO2004044104A1 (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060219979A1 (en) * 2005-04-04 2006-10-05 Degussa Ag Method of increasing the oxidation stability of biodiesel
US20060218855A1 (en) * 2005-04-04 2006-10-05 Degussa Ag Method of increasing the oxidation stability of biodiesel
US20070197412A1 (en) * 2006-02-03 2007-08-23 Thomas Edward Carter Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
EP1847583A2 (fr) * 2006-04-21 2007-10-24 Infineum International Limited Biocarburant amélioré
JP2007291391A (ja) * 2006-04-21 2007-11-08 Infineum Internatl Ltd バイオ燃料における改善
US20080022584A1 (en) * 2006-07-26 2008-01-31 Mark Schomann Alternative organic fuel formulations including vegetable oil
US20080127550A1 (en) * 2006-11-27 2008-06-05 Natalie Li Stabilized biodiesel fuel compositions
US20090094887A1 (en) * 2007-10-16 2009-04-16 General Electric Company Methods and compositions for improving stability of biodiesel and blended biodiesel fuel
EP2052061A2 (fr) * 2006-07-11 2009-04-29 Innospec Fuel Specialties LLC Compositions stabilisantes pour mélanges de pétrole et de carburants renouvelables
US20090158644A1 (en) * 2006-04-10 2009-06-25 Oxiris Chemicals S.A. Method of increasing the oxidation stability of biodiesel
EP2174554A2 (fr) 2008-10-09 2010-04-14 Infineum International Limited Améliorations pour huiles
WO2012130535A1 (fr) 2011-03-25 2012-10-04 Evonik Rohmax Additives Gmbh Composition pour améliorer la stabilité à l'oxydation de mazouts
WO2014040919A1 (fr) 2012-09-13 2014-03-20 Evonik Oil Additives Gmbh Composition pour améliorer les propriétés à basse température et la stabilité à l'oxydation d'huiles végétales et de graisses animales
KR101502643B1 (ko) * 2007-07-28 2015-03-13 이노스펙 리미티드 연료 오일 조성물 및 그를 위한 첨가제
WO2017054921A1 (fr) * 2015-09-30 2017-04-06 Inachem Gmbh Compositions d'antioxydants stables au stockage contenant de l'acide ascorbique

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Publication number Priority date Publication date Assignee Title
DE102005048881A1 (de) * 2005-10-12 2007-04-19 Forschungszentrum Karlsruhe Gmbh Verfahren zur Lösungskristallisation von Stoffgemischen
WO2007079765A1 (fr) * 2005-12-30 2007-07-19 Clean Oil Ag Combustible diesel-huile vegetale
KR20080089386A (ko) * 2006-01-04 2008-10-06 시바 홀딩 인코포레이티드 안정화된 바이오디젤 연료 조성물
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)
US9493709B2 (en) 2011-03-29 2016-11-15 Fuelina Technologies, Llc Hybrid fuel and method of making the same
RU2476585C1 (ru) * 2012-03-07 2013-02-27 Открытое Акционерное Общество "Стерлитамакский Нефтехимический Завод" Композиция антиокислительной присадки, ее раствор и способ повышения стабильности биодизельного топлива при хранении (варианты)
AU2015358565B2 (en) 2014-12-03 2020-11-05 Drexel University Direct incorporation of natural gas into hydrocarbon liquid fuels
EP3053992A1 (fr) * 2015-02-09 2016-08-10 LANXESS Deutschland GmbH Biodiesel

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US5354878A (en) * 1992-03-26 1994-10-11 Joosten Connemann Process for the continuous production of lower alkyl esters of higher fatty acids

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AU674052B2 (en) * 1993-05-24 1996-12-05 Lubrizol Corporation, The Pour point depressant treated fatty acid esters as biodegradable, combustion engine fuels
US5580482A (en) * 1995-01-13 1996-12-03 Ciba-Geigy Corporation Stabilized lubricant compositions
US5711767A (en) * 1996-07-11 1998-01-27 Ciba Specialty Chemicals Corporation Stabilizers for the prevention of gum formation in gasoline
US5891203A (en) * 1998-01-20 1999-04-06 Ethyl Corporation Fuel lubricity from blends of a diethanolamine derivative and biodiesel

Patent Citations (2)

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US4769178A (en) * 1985-03-19 1988-09-06 Kao Corporation Cold-rolling lube oil for metallic materials
US5354878A (en) * 1992-03-26 1994-10-11 Joosten Connemann Process for the continuous production of lower alkyl esters of higher fatty acids

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060218855A1 (en) * 2005-04-04 2006-10-05 Degussa Ag Method of increasing the oxidation stability of biodiesel
US20060219979A1 (en) * 2005-04-04 2006-10-05 Degussa Ag Method of increasing the oxidation stability of biodiesel
US20070197412A1 (en) * 2006-02-03 2007-08-23 Thomas Edward Carter Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
US9422508B2 (en) 2006-02-03 2016-08-23 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
US8075804B2 (en) 2006-02-03 2011-12-13 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
US20090158644A1 (en) * 2006-04-10 2009-06-25 Oxiris Chemicals S.A. Method of increasing the oxidation stability of biodiesel
EP1847583A2 (fr) * 2006-04-21 2007-10-24 Infineum International Limited Biocarburant amélioré
JP2007291391A (ja) * 2006-04-21 2007-11-08 Infineum Internatl Ltd バイオ燃料における改善
EP1847583A3 (fr) * 2006-04-21 2008-11-05 Infineum International Limited Biocarburant amélioré
EP2052061A4 (fr) * 2006-07-11 2012-01-25 Innospec Fuel Specialties Llc Compositions stabilisantes pour mélanges de pétrole et de carburants renouvelables
JP2009542889A (ja) * 2006-07-11 2009-12-03 インノスペック フューエル スペシャルティーズ エルエルシー 石油および再生可能燃料のブレンド用の安定剤組成物
US20090300974A1 (en) * 2006-07-11 2009-12-10 Innospec, Inc. Stabilizer compositions for blends of petroleum and renewable fuels
EP2052061A2 (fr) * 2006-07-11 2009-04-29 Innospec Fuel Specialties LLC Compositions stabilisantes pour mélanges de pétrole et de carburants renouvelables
US20080022584A1 (en) * 2006-07-26 2008-01-31 Mark Schomann Alternative organic fuel formulations including vegetable oil
US7901469B2 (en) 2006-07-26 2011-03-08 Alternative Fuels Group Inc. Alternative organic fuel formulations including vegetable oil
WO2008065015A1 (fr) * 2006-11-27 2008-06-05 Ciba Holding Inc. Compositions stabilisées de carburant biodiesel
US20080127550A1 (en) * 2006-11-27 2008-06-05 Natalie Li Stabilized biodiesel fuel compositions
KR101502643B1 (ko) * 2007-07-28 2015-03-13 이노스펙 리미티드 연료 오일 조성물 및 그를 위한 첨가제
US20090094887A1 (en) * 2007-10-16 2009-04-16 General Electric Company Methods and compositions for improving stability of biodiesel and blended biodiesel fuel
EP2174554A3 (fr) * 2008-10-09 2011-01-12 Infineum International Limited Procédé d'augmentation de la stabilité à l oxydation d'huile végetale ou animale
EP2174554A2 (fr) 2008-10-09 2010-04-14 Infineum International Limited Améliorations pour huiles
WO2012130535A1 (fr) 2011-03-25 2012-10-04 Evonik Rohmax Additives Gmbh Composition pour améliorer la stabilité à l'oxydation de mazouts
US20140033605A1 (en) * 2011-03-25 2014-02-06 Evonik Oil Additives Gmbh Composition to improve oxidation stability of fuel oils
US9284505B2 (en) * 2011-03-25 2016-03-15 Evonik Oil Additives Gmbh Composition to improve oxidation stability of fuel oils
WO2014040919A1 (fr) 2012-09-13 2014-03-20 Evonik Oil Additives Gmbh Composition pour améliorer les propriétés à basse température et la stabilité à l'oxydation d'huiles végétales et de graisses animales
US20150232783A1 (en) * 2012-09-13 2015-08-20 Evonik Oil Additives Gmbh Composition to improve low temperature properties and oxidation stability of vegetable oils and animal fats
WO2017054921A1 (fr) * 2015-09-30 2017-04-06 Inachem Gmbh Compositions d'antioxydants stables au stockage contenant de l'acide ascorbique

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PT1563041E (pt) 2008-09-25
RU2008126167A (ru) 2010-01-10
ES2308038T3 (es) 2008-12-01
RU2475520C2 (ru) 2013-02-20
WO2004044104A1 (fr) 2004-05-27
ES2629089T3 (es) 2017-08-07
ATE399834T1 (de) 2008-07-15
AU2003257439A1 (en) 2004-06-03
EP1972679A1 (fr) 2008-09-24
RU2005118759A (ru) 2006-01-10
EP1563041B1 (fr) 2008-07-02
EP1972679B1 (fr) 2017-05-10
UA86007C2 (uk) 2009-03-25
EP1563041A1 (fr) 2005-08-17
SI1563041T1 (sl) 2009-02-28
RU2340655C2 (ru) 2008-12-10
DK1563041T3 (da) 2008-10-20
PL203138B1 (pl) 2009-08-31
US20080313956A1 (en) 2008-12-25
DE50310078D1 (de) 2008-08-14
PL376777A1 (pl) 2006-01-09

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