WO2009113079A1 - A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol - Google Patents
A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol Download PDFInfo
- Publication number
- WO2009113079A1 WO2009113079A1 PCT/IN2008/000144 IN2008000144W WO2009113079A1 WO 2009113079 A1 WO2009113079 A1 WO 2009113079A1 IN 2008000144 W IN2008000144 W IN 2008000144W WO 2009113079 A1 WO2009113079 A1 WO 2009113079A1
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- WO
- WIPO (PCT)
- Prior art keywords
- glycerol
- process according
- range
- alcohol
- ethers
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- 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 present invention relates to a process of the preparation of biofuels or biofuel additives from glycerol. More particularly, it relates to a process for the preparation of glycerol ethers by etherification of glycerol with an alcohol using solid acid catalysts.
- Glycerol is a by-product in the manufacture of biodiesel by transesterification of triglycerides with alcohols like methanol. In this process, a large amount of glycerol is produced that is not utilized as a part of the biofuel. At present, glycerol finds applications only in very small volume products in the pharmaceutical industry. Other grade uses of glycerol include mixing with animal manure to form a fertilizer, and mixing with feed for animals. The economics of production of biodiesel can be significantly improved if new uses of the large' amount of glycerol produced are found.
- U.S. patents 6,174,501 and 6,015,440 claim a process for producing biodiesel fuel with reduced viscosity and cloud point below 32 Fahrenheit wherein triglycerides are reacted in a liquid phase reaction with methanol and a homogeneous basic catalyst, like NaOH 1 yielding methyl esters and a glycerol phase containing, mainly, glycerol and some residual methanol.
- the glycerol phase was passed through a strong cationic ion exchange to remove anions, resulting in a neutral product, which was flashed to remove methanol and then, reacted with an olefin, like isobutylene or isoamylene, in the presence of a strong acid catalyst to produce glycerol ethers.
- the glycerol ethers are then added back to the methyl esters of glycerol to provide an improved biodiesel.
- U.S. patent 5,476,971 describes reacting pure glycerol with isobutylene in the presence of an acid catalyst in a two-phase reaction to produce mono-, di- and tri-tertiary butyl ethers of glycerol.
- isobutylene is claimed as the etherifying agent. Since triglycerides are obtained from vegetable oils, like Soya bean oil, palm oil and rapeseed oil, and olefins like isobutylene and isoamylene are obtained from the catalytic cracking of petroleum fractions, it will be more desirable to use, as etherifying agents, chemicals that are available in the agro industry, like agro ethanol. Only biodiesel containing blending components that are not sourced from fossil fuels can truly be called "biofuels".
- chemical compounds containing the tertiary alkyl carbon atoms, like isobutylene and the glycerol ethers made from olefins, like isobutylene or isoamylene are less biodegradable than those containing only primary carbon atoms, like ethanol, butanol or the glyceryl ethers made from such alcohols.
- a primary alcohol which is also available from the agro industry, such as ethanol, to etherify the glycerol.
- continuous removal of the water formed during the reaction is also beneficial in driving the reaction to the product side.
- Carrying out the etherification reaction at temperatures higher than the boiling point of water (100 0 C) is also beneficial since above 100 0 C, the water formed can be continuously removed from the catalyst.
- cation exchange resins for their use in etherification reactions above 100 0 C is that these polymeric resins are structurally unstable above about 100 - 12O 0 C and, hence, undergo irreversible structural decomposition above these temperatures.
- the main objective of the present invention is to provide a process for the preparation of glycerol derived ethers and used thereof as biofuels or additive in biofuels. Another object is to provide a single-step process for the preparation of glycerol ethers from the glycerol fraction of the products in the transesterification of vegetable oils and animal fats.
- Yet another object of the present invention is to produce glycerol ethers by etherification of glycerol fraction obtained in the transesterification of vegetable oil or fat with a C1 - C8 alcohol, over a solid catalyst, at moderate conditions and shorter reaction times.
- the present invention provides a process for the preparation of primary alkyl glycerol ethers which comprises reacting a primary alcohol with glycerol, in a molar ratio of primary alcohol to glycerol in the range of 3:1 to 9:1, in the presence of a solid acid catalyst, at a temperature in the range of 60 to
- the primary alcohol used is selected from the group consisting of methanol, ethanol, butanol and octanol.
- the molar ratio of primary alcohol to glycerol is preferably in the range of 4 : 1 to 6 : 1.
- the solid acid catalyst used is selected from the group consisting of alumina, aluminosilicate, silicoaluminophosphate, solid phosphoric acid, sulphated zirconium oxide, sulphonic acid or thiol-functionalised silica and cation exchange resin.
- the aluminosilicate used is selected from the group consisting of zeolite beta, zeolite Y and mordenite.
- the cation exchange resin used is Amberlyst-
- reaction temperature used is preferably in the range of 60-150 0 C.
- the reactor used is selected from the group of consisting of continuous stirred tank reactor, reactive distillation reactor and continuous-flow fixed-bed reactor.
- the glycerol used is a glycerol obtained as byproduct in the transesterification of vegetable oil or fat with alcohol.
- the glycerol-containing feedstock contains in addition to glycerol, esters of glycerol and carboxylic acids.
- the % conversion of glycerol is in the range of 60-95% by weight.
- the yield of glycerol obtained is in the range of 50-100% by weight of glycerol used.
- the present invention describes a process for the manufacture of glycerol ethers and more particularly, to a process for the manufacture of glycerol ethers by etherifying glycerol with a primary alcohol using solid, acid catalysts.
- the process comprises contacting a mixture of a primary alcohol and a glycerol- containing feedstock with a solid catalyst in a reactor at a temperature in the range of 60 to 300 0 C and a pressure of 1 - 10 bars and separating out most of the formed glycerol ethers from the reaction mixture.
- the glycerol- containing feedstock can be conveniently obtained from the products of the transesterification of the triglycerides provided from vegetable oils.
- the tranesterification of glycerides with methanol to yield biodiesel is well- known in the prior art.
- base catalysts like NaOH or KOH are used in the liquid, homogeneous phase are used.
- the effluent from the transesterification of vegetable oils over solid catalysts described in more detail in our above mentioned co-pending Indian patent applications: 1561 /DEL/2005 and 2722/DEL/2005 contains two, non- miscible, separable liquid phases, a lighter non-polar layer containing mainly the alkyl (methyl or ethyl) esters of the fatty acids (the biodiesel fraction) and a polar, heavier liquid layer containing glycerol and un reacted alcohol (methanol or ethanol).
- the glycerol and alcohol-containing fraction obtained after removal of the biodiesel fraction, by decantation, for example, can, after addition of alcohol, if needed, constitutes a suitable feedstock for the process of the present invention.
- This glycerol and alcohol-containing feedstock after adjusting the alcohol to glycerol molar ratio to be above 4, if needed, is next contacted with a solid acid catalyst in a reaction zone maintained at reaction conditions optimized for the etherification reaction.
- a reaction zone maintained at reaction conditions optimized for the etherification reaction.
- the reaction is carried out at the autogenous pressure of the alcohol at the reaction temperature.
- the reaction zone can be constituted by a continuous stirred tank reactor (CSTR) or a continuous fixed bed reactor.
- WHSV weight hourly space velocity
- the choice idf the alcohol was determined by the end - use of the glycerol ether: If the glycerol ether is to be used as a blending component in biodiesel, then, methanol and ethanol were the preferred alcohols while octanol was the alcohol of choice )if the;glyeerol ethers were to be used as biolubricants. Primary alcohols were preferred over secondary and tertiary alcohols in view of the greater biodegradability of the former. Thus, if production of biodiesel is the target, methanol or ethanol was used both in the transesterification as well as the etherification reactions.
- the solid catalyst used in the process of the present invention can be any solid acid, which contains substantial amounts of Lewis or Br ⁇ nsted acid sites on the surface.
- solid acids include alumina, fluorided alumina, chlorided alumina, amorphous silicoalumina, solid phosphoric acid, zeolites like zeolite Y 1 ;beta, inordenite, medium pore zeolites, silicoalumino phosphates, divalent metal-containing alumino phosphates, sulfated zirconium oxide and acid-washed clays.
- the primary alcohol used in this invention is selected from methanol, ethanol, butanol, and octanol, preferably agro-ethanol obtained from the fermentation of agro products like sugarcane and containing significant amounts of water.
- the solid catalyst used in the present invention is a solid acid catalyst, preferably alumina, silicoalumina, an aluminosilicate molecular sieve, a silicoaluminophosphate molecular sieve, acid-washed clay, solid phosphoric acid , or sulfated zirconium oxide.
- This example illustrates the preparation of glycerol ethyl ethers over gamma alumina catalyst.
- ethanol and glycerol in a molar ratio of 5 : 1, were heated with gamma-alumina catalyst (5% wt of the total reaction mixture) in a closed autoclave at 100 0 C for 5 hours.
- the solid acid, catalyst - gamma alumina was procured from commercial sources.
- the solid catalyst was pre-treated and activated at 500 0 C by procedures recommended by the catalyst manufacturer and well- known to those skilled in the art.
- the solid catalyst was removed, and the glycerol ethers were separated from the unreacted glycerol, water and alcohol by a combination of extraction (with water) and distillation procedures. The products were analyzed by gas chromatography.
- ethanol and glycerol in a molar ratio of 5 : 1 , were heated with zeolite-beta (5% wt of the total reaction mixture) in a closed autoclave at 100 0 C for 5 hours.
- the solid catalyst was pre-treated activating at 450 0 C.
- the catalyst was removed, and the glycerol ethers were separated from the unreacted glycerol, water and alcohol by a combination of extraction (with water) and distillation procedures. The products were analyzed by gas chromatography.
- zeolite-Y 5% wt of the total reaction mixture
- the solid catalyst was pre-treated activating at 450 0 C.
- the catalyst was removed, and the glycerol ethers were separated from the unreacted glycerol, water and alcohol by a combination of extraction (with water) and distillation procedures. The products were analyzed by gas chromatography.
- This example illustrates the preparation of glycerol ethyl ethers over silicoalumino phosphate catalyst.
- ethanol and glycerol in a molar ratio of 5:1 , were heated with the catalyst (5% wt of the total reaction mixture) in a closed autoclave at 100 0 C for 5 hours.
- the solid catalyst was pre- treated activating at 350 0 C.
- the catalyst was removed, and the glycerol ethers were separated from the unreacted glycerol, water and alcohol by a combination of extraction (with water) and distillation procedures. The products were analyzed by gas chromatography.
- This example illustrates the preparation of glycerol ethyl ethers over Amberlyst- 15 cation exchange resin (strongly acidic, macroreticular resin with sulfonic acid functionality, Aldrich Co.).
- Amberlyst- 15 cation exchange resin strongly acidic, macroreticular resin with sulfonic acid functionality, Aldrich Co.
- ethanol and glycerol in a molar ratio of 5 : 1 , were heated with amberiyst-15 (5% wt of the total reaction mixture) in a closed autoclave at 100 0 C for 5 hours.
- the resin was pre-treated with 3 M H 2 SO 4 and then activating at 100 0 C prior to use.
- the catalyst was removed, and the glycerol ethers were separated from the unreacted glycerol, water and alcohol by a combination of extraction (with water) and distillation procedures. The products were analyzed by gas chromatography.
- Example 6 This example illustrates the preparation of glycerol ethyl ethers over solid phosphoric acid.
- ethanol and glycerol in a molar ratio of 5 : 1 , were heated with solid phosphoric acid (5% wt of the total reaction mixture) in a . closed autoclave at 100 0 C for 5 hours.
- the catalyst was removed, and the glycerol ethers were separated from the unreacted glycerol, water and alcohol by a combination of extraction (with water) and distillation procedures. The products were analyzed by gas chromatography.
- agro- ethanol (water content 5%) and glycerol, in a molar ratio of 5 : 1 were heated with zeolite-beta (5% wt of the total reaction mixture) in a closed autoclave at 100°C for * 5 hours.
- the solid catalyst was pre-treated activating at 45O 0 C.
- the catalyst was removed, and the glycerol ethers were separated from the unreacted glycerol, water and alcohol by a combination of extraction (with water) and distillation procedures. The products were analyzed by gas chromatography.
- butanol and glycerol in a molar ratio of 5 : 1, were heated with zeolite-beta (7.5% wt of the total reaction mixture) in a closed autoclave at 6O 0 C for 8 hours.
- the solid catalyst was pre-treated activating at 450°C.
- butanol and glycerol in a molar ratio of 5 : 1, were heated with zeolite-beta (7.5% wt of the total reaction mixture) in a closed autoclave at 90 0 C for 8 hours.
- the solid catalyst was pre-trea activating at 450 0 C.
- the catalyst was removed, and the glycerol ethers were separated from the unreacted glycerol, water and alcohol by a combination of extraction (with water) and distillation procedures.
- the liquid products were analyzed by gas chromatography.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
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Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08720163.8A EP2274262B1 (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
AU2008352536A AU2008352536B2 (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
RU2010141835/04A RU2478091C2 (en) | 2008-03-13 | 2008-03-13 | Method of producing primary alkyl ethers of glycerol, suitable as biofuel additive, from glycerol |
CN2008801280002A CN101970390A (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
CA2718474A CA2718474C (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
MX2010010054A MX345089B (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol. |
US12/922,042 US20110015447A1 (en) | 2008-03-13 | 2008-03-13 | Process for the Preparation of Primary Alkyl Glycerol Ethers Useful as Biofuel Additive from Glycerol |
KR1020107022198A KR20110027645A (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
JP2010550330A JP2011513478A (en) | 2008-03-13 | 2008-03-13 | Process for the preparation of primary alkyl glycerol ethers useful as biofuel additives from glycerol |
PCT/IN2008/000144 WO2009113079A1 (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
BRPI0822426-9A BRPI0822426A2 (en) | 2008-03-13 | 2008-03-13 | Process for the preparation of primary alkyl glycerol ethers useful as glycerol biofuel additive |
NZ588450A NZ588450A (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
MYPI2010004272A MY162898A (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IN2008/000144 WO2009113079A1 (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
Publications (2)
Publication Number | Publication Date |
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WO2009113079A1 true WO2009113079A1 (en) | 2009-09-17 |
WO2009113079A8 WO2009113079A8 (en) | 2009-11-12 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/IN2008/000144 WO2009113079A1 (en) | 2008-03-13 | 2008-03-13 | A process for the preparation of primary alkyl glycerol ethers useful as biofuel additive from glycerol |
Country Status (13)
Country | Link |
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US (1) | US20110015447A1 (en) |
EP (1) | EP2274262B1 (en) |
JP (1) | JP2011513478A (en) |
KR (1) | KR20110027645A (en) |
CN (1) | CN101970390A (en) |
AU (1) | AU2008352536B2 (en) |
BR (1) | BRPI0822426A2 (en) |
CA (1) | CA2718474C (en) |
MX (1) | MX345089B (en) |
MY (1) | MY162898A (en) |
NZ (1) | NZ588450A (en) |
RU (1) | RU2478091C2 (en) |
WO (1) | WO2009113079A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ302523B6 (en) * | 2009-11-05 | 2011-06-29 | Výzkumný ústav anorganické chemie, a. s. | Process for preparing glycerol ethers |
CN103611568A (en) * | 2013-12-02 | 2014-03-05 | 江南大学 | Preparation method of dual-core acidic ionic liquid immobilized SBA-15 molecular sieve catalyst used for synthesizing tert butyl glycidyl ether |
US8962873B2 (en) | 2011-03-09 | 2015-02-24 | Benefuel, Inc. | Systems and methods for making bioproducts |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010006402A1 (en) * | 2008-07-16 | 2010-01-21 | Her Majesty The Queen In Right Of Canada As Represented By The Minister Of Natural Resources Canada | Conversion of glycerol to naphtha-range oxygenates |
CN102391076A (en) * | 2011-10-08 | 2012-03-28 | 中国科学院山西煤炭化学研究所 | Method for preparing glycerol single methanol ether by utilizing glycerol and methanol |
CN102504891B (en) * | 2011-11-02 | 2014-11-05 | 南京工业大学 | Preparation method of glyceryl biological fuel additives |
EP2847155A4 (en) * | 2012-05-11 | 2015-12-16 | Rhodia Operations | Preparation of an ether compound |
Citations (1)
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US20070260078A1 (en) * | 2006-05-05 | 2007-11-08 | Bhat Ramanath N | Integrated process for the manufacture of biodiesel |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5476971A (en) * | 1995-01-13 | 1995-12-19 | Arco Chemical Technology, L.P. | Glycerine ditertiary butyl ether preparation |
US5731476A (en) * | 1995-01-13 | 1998-03-24 | Arco Chemical Technology, L.P. | Poly ether preparation |
US6015440A (en) * | 1997-10-31 | 2000-01-18 | Board Of Regents Of The University Of Nebraska | Process for producing biodiesel fuel with reduced viscosity and a cloud point below thirty-two (32) degrees fahrenheit |
DE10150728A1 (en) * | 2001-10-13 | 2003-04-17 | Cognis Deutschland Gmbh | Glycerol monoalkyl ethers, used as fat-replacement agents in surfactant-containing cosmetic or pharmaceutical compositions, optionally together with fatty alcohols |
WO2007061903A1 (en) * | 2005-11-17 | 2007-05-31 | Cps Biofuels, Inc. | Alternative fuel and fuel additive compositions |
US20070238905A1 (en) * | 2006-04-05 | 2007-10-11 | Victor Manuel Arredondo | Processes for converting glycerol to glycerol ethers |
-
2008
- 2008-03-13 CA CA2718474A patent/CA2718474C/en active Active
- 2008-03-13 JP JP2010550330A patent/JP2011513478A/en active Pending
- 2008-03-13 NZ NZ588450A patent/NZ588450A/en unknown
- 2008-03-13 AU AU2008352536A patent/AU2008352536B2/en active Active
- 2008-03-13 WO PCT/IN2008/000144 patent/WO2009113079A1/en active Application Filing
- 2008-03-13 RU RU2010141835/04A patent/RU2478091C2/en active
- 2008-03-13 EP EP08720163.8A patent/EP2274262B1/en active Active
- 2008-03-13 BR BRPI0822426-9A patent/BRPI0822426A2/en not_active Application Discontinuation
- 2008-03-13 US US12/922,042 patent/US20110015447A1/en not_active Abandoned
- 2008-03-13 KR KR1020107022198A patent/KR20110027645A/en active Search and Examination
- 2008-03-13 MY MYPI2010004272A patent/MY162898A/en unknown
- 2008-03-13 MX MX2010010054A patent/MX345089B/en active IP Right Grant
- 2008-03-13 CN CN2008801280002A patent/CN101970390A/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070260078A1 (en) * | 2006-05-05 | 2007-11-08 | Bhat Ramanath N | Integrated process for the manufacture of biodiesel |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ302523B6 (en) * | 2009-11-05 | 2011-06-29 | Výzkumný ústav anorganické chemie, a. s. | Process for preparing glycerol ethers |
US8962873B2 (en) | 2011-03-09 | 2015-02-24 | Benefuel, Inc. | Systems and methods for making bioproducts |
US10023523B2 (en) | 2011-03-09 | 2018-07-17 | Benefuel, Inc. | Systems and methods for making bioproducts |
CN103611568A (en) * | 2013-12-02 | 2014-03-05 | 江南大学 | Preparation method of dual-core acidic ionic liquid immobilized SBA-15 molecular sieve catalyst used for synthesizing tert butyl glycidyl ether |
Also Published As
Publication number | Publication date |
---|---|
CA2718474A1 (en) | 2009-09-17 |
CN101970390A (en) | 2011-02-09 |
CA2718474C (en) | 2014-07-22 |
KR20110027645A (en) | 2011-03-16 |
MX345089B (en) | 2017-01-17 |
WO2009113079A8 (en) | 2009-11-12 |
AU2008352536B2 (en) | 2013-06-13 |
AU2008352536A1 (en) | 2009-09-17 |
MY162898A (en) | 2017-07-31 |
JP2011513478A (en) | 2011-04-28 |
RU2478091C2 (en) | 2013-03-27 |
EP2274262A1 (en) | 2011-01-19 |
MX2010010054A (en) | 2010-12-21 |
BRPI0822426A2 (en) | 2015-06-16 |
NZ588450A (en) | 2012-06-29 |
US20110015447A1 (en) | 2011-01-20 |
RU2010141835A (en) | 2012-04-20 |
EP2274262B1 (en) | 2018-08-29 |
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