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 PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- biodiesel
- bht
- tert
- increasing
- butylhydroxytoluene
- 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.)
- Abandoned
Links
- 239000003225 biodiesel Substances 0.000 title claims abstract description 79
- 238000003860 storage Methods 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 17
- ZRDUANIDHBCCAO-UHFFFAOYSA-N (2,4-ditert-butylphenyl)methanol Chemical compound CC(C)(C)C1=CC=C(CO)C(C(C)(C)C)=C1 ZRDUANIDHBCCAO-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000011550 stock solution Substances 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims abstract description 10
- 235000015073 liquid stocks Nutrition 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- 235000019482 Palm oil Nutrition 0.000 claims description 3
- 239000008162 cooking oil Substances 0.000 claims description 3
- 239000002540 palm oil Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 235000019737 Animal fat Nutrition 0.000 claims 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 46
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 46
- 229920000642 polymer Polymers 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000007792 addition Methods 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 5
- -1 unsaturated fatty acid methyl esters Chemical class 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001382 dynamic differential scanning calorimetry Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
Images
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
-
- 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)
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 |
---|---|---|---|
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 |
DE10252715.6 | 2002-11-13 | ||
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 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
Publications (1)
Publication Number | Publication Date |
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US20040139649A1 true US20040139649A1 (en) | 2004-07-22 |
Family
ID=32313557
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
Country Status (13)
Country | Link |
---|---|
US (2) | US20040139649A1 (pl) |
EP (2) | EP1563041B1 (pl) |
AT (1) | ATE399834T1 (pl) |
AU (1) | AU2003257439A1 (pl) |
DE (1) | DE50310078D1 (pl) |
DK (1) | DK1563041T3 (pl) |
ES (2) | ES2629089T3 (pl) |
PL (1) | PL203138B1 (pl) |
PT (1) | PT1563041E (pl) |
RU (2) | RU2340655C2 (pl) |
SI (1) | SI1563041T1 (pl) |
UA (1) | UA86007C2 (pl) |
WO (1) | WO2004044104A1 (pl) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
EP1847583A2 (en) * | 2006-04-21 | 2007-10-24 | Infineum International Limited | Improvements in Biofuel |
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 |
WO2008065015A1 (en) * | 2006-11-27 | 2008-06-05 | Ciba Holding Inc. | Stabilised 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 (en) * | 2006-07-11 | 2009-04-29 | Innospec Fuel Specialties LLC | Stabilizer compositions for blends of petroleum and renewable fuels |
US20090158644A1 (en) * | 2006-04-10 | 2009-06-25 | Oxiris Chemicals S.A. | Method of increasing the oxidation stability of biodiesel |
EP2174554A2 (en) | 2008-10-09 | 2010-04-14 | Infineum International Limited | Improvements in oils |
WO2012130535A1 (en) | 2011-03-25 | 2012-10-04 | Evonik Rohmax Additives Gmbh | A composition to improve oxidation stability of fuel oils |
WO2014040919A1 (en) | 2012-09-13 | 2014-03-20 | Evonik Oil Additives Gmbh | A composition to improve low temperature properties and oxidation stability of vegetable oils and animal fats |
KR101502643B1 (ko) * | 2007-07-28 | 2015-03-13 | 이노스펙 리미티드 | 연료 오일 조성물 및 그를 위한 첨가제 |
WO2017054921A1 (en) * | 2015-09-30 | 2017-04-06 | Inachem Gmbh | Storage -stable compositions of antioxidants containing ascorbic acid |
Families Citing this family (8)
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 (de) * | 2005-12-30 | 2007-07-19 | Clean Oil Ag | Pflanzenöl-dieselkraftstoff |
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) |
CN103842487A (zh) | 2011-03-29 | 2014-06-04 | 富林纳技术有限公司 | 混合燃料及其制备方法 |
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) |
EA037733B1 (ru) | 2014-12-03 | 2021-05-14 | Дрексел Юниверсити | Прямое включение природного газа в жидкие углеводородные топлива |
EP3053992A1 (de) * | 2015-02-09 | 2016-08-10 | LANXESS Deutschland GmbH | Biodiesel |
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-
2003
- 2003-07-08 RU RU2005118759/04A patent/RU2340655C2/ru active
- 2003-07-08 DK DK03810944T patent/DK1563041T3/da active
- 2003-07-08 AU AU2003257439A patent/AU2003257439A1/en not_active Abandoned
- 2003-07-08 SI SI200331324T patent/SI1563041T1/sl unknown
- 2003-07-08 AT AT03810944T patent/ATE399834T1/de active
- 2003-07-08 ES ES08158423.7T patent/ES2629089T3/es not_active Expired - Lifetime
- 2003-07-08 EP EP03810944A patent/EP1563041B1/de not_active Expired - Lifetime
- 2003-07-08 PL PL376777A patent/PL203138B1/pl unknown
- 2003-07-08 WO PCT/EP2003/007310 patent/WO2004044104A1/de active IP Right Grant
- 2003-07-08 PT PT03810944T patent/PT1563041E/pt unknown
- 2003-07-08 ES ES03810944T patent/ES2308038T3/es not_active Expired - Lifetime
- 2003-07-08 RU RU2008126167/05A patent/RU2475520C2/ru active
- 2003-07-08 DE DE50310078T patent/DE50310078D1/de not_active Expired - Lifetime
- 2003-07-08 EP EP08158423.7A patent/EP1972679B1/de not_active Expired - Lifetime
- 2003-08-07 UA UAA200505604A patent/UA86007C2/uk unknown
- 2003-11-07 US US10/703,263 patent/US20040139649A1/en not_active Abandoned
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2008
- 2008-06-12 US US12/157,692 patent/US20080313956A1/en not_active Abandoned
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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 |
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 (en) * | 2006-04-21 | 2007-10-24 | Infineum International Limited | Improvements in Biofuel |
JP2007291391A (ja) * | 2006-04-21 | 2007-11-08 | Infineum Internatl Ltd | バイオ燃料における改善 |
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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 |
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US20080022584A1 (en) * | 2006-07-26 | 2008-01-31 | Mark Schomann | Alternative organic fuel formulations including vegetable oil |
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US20080127550A1 (en) * | 2006-11-27 | 2008-06-05 | Natalie Li | Stabilized biodiesel fuel compositions |
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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 (en) * | 2008-10-09 | 2011-01-12 | Infineum International Limited | Improving the oxidation stability of oils of vegetable or animal origin |
EP2174554A2 (en) | 2008-10-09 | 2010-04-14 | Infineum International Limited | Improvements in oils |
WO2012130535A1 (en) | 2011-03-25 | 2012-10-04 | Evonik Rohmax Additives Gmbh | A composition to improve oxidation stability of fuel oils |
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 (en) | 2012-09-13 | 2014-03-20 | Evonik Oil Additives Gmbh | A composition to improve low temperature properties and oxidation stability of vegetable oils and animal fats |
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 (en) * | 2015-09-30 | 2017-04-06 | Inachem Gmbh | Storage -stable compositions of antioxidants containing ascorbic acid |
Also Published As
Publication number | Publication date |
---|---|
DK1563041T3 (da) | 2008-10-20 |
PT1563041E (pt) | 2008-09-25 |
RU2475520C2 (ru) | 2013-02-20 |
RU2340655C2 (ru) | 2008-12-10 |
DE50310078D1 (de) | 2008-08-14 |
PL376777A1 (pl) | 2006-01-09 |
ATE399834T1 (de) | 2008-07-15 |
RU2005118759A (ru) | 2006-01-10 |
AU2003257439A1 (en) | 2004-06-03 |
ES2629089T3 (es) | 2017-08-07 |
PL203138B1 (pl) | 2009-08-31 |
EP1563041B1 (de) | 2008-07-02 |
EP1972679B1 (de) | 2017-05-10 |
RU2008126167A (ru) | 2010-01-10 |
SI1563041T1 (sl) | 2009-02-28 |
WO2004044104A1 (de) | 2004-05-27 |
EP1563041A1 (de) | 2005-08-17 |
UA86007C2 (uk) | 2009-03-25 |
ES2308038T3 (es) | 2008-12-01 |
US20080313956A1 (en) | 2008-12-25 |
EP1972679A1 (de) | 2008-09-24 |
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