CA2698642A1 - Production of fatty acid and fatty acid ester - Google Patents
Production of fatty acid and fatty acid ester Download PDFInfo
- Publication number
- CA2698642A1 CA2698642A1 CA2698642A CA2698642A CA2698642A1 CA 2698642 A1 CA2698642 A1 CA 2698642A1 CA 2698642 A CA2698642 A CA 2698642A CA 2698642 A CA2698642 A CA 2698642A CA 2698642 A1 CA2698642 A1 CA 2698642A1
- Authority
- CA
- Canada
- Prior art keywords
- fatty acid
- process according
- acid
- mixture
- phase
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 89
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 89
- 239000000194 fatty acid Substances 0.000 title claims abstract description 89
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 57
- -1 fatty acid ester Chemical class 0.000 title claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- 238000000034 method Methods 0.000 claims abstract description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 38
- 239000012071 phase Substances 0.000 claims abstract description 30
- 239000007858 starting material Substances 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 239000007791 liquid phase Substances 0.000 claims abstract description 12
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 11
- 239000012074 organic phase Substances 0.000 claims abstract description 11
- 239000003377 acid catalyst Substances 0.000 claims abstract description 9
- 239000008346 aqueous phase Substances 0.000 claims abstract description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 49
- 239000000344 soap Substances 0.000 claims description 47
- 239000002244 precipitate Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 239000003225 biodiesel Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 5
- 239000001110 calcium chloride Substances 0.000 claims description 5
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000001117 sulphuric acid Substances 0.000 claims description 4
- 235000011149 sulphuric acid Nutrition 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- 239000005416 organic matter Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000003925 fat Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000010306 acid treatment Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000002551 biofuel Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000001131 transforming effect Effects 0.000 description 3
- 238000010977 unit operation Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 239000004165 Methyl ester of fatty acids Substances 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002313 glycerolipids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
- C11B13/02—Recovery of fats, fatty oils or fatty acids from waste materials from soap stock
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D13/00—Making of soap or soap solutions in general; Apparatus therefor
- C11D13/30—Recovery of soap, e.g. from spent solutions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
-
- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
-
- 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
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99301407P | 2007-09-07 | 2007-09-07 | |
| US60/993,014 | 2007-09-07 | ||
| FI20075619 | 2007-09-07 | ||
| FI20075619A FI20075619L (fi) | 2007-09-07 | 2007-09-07 | Rasvahapon ja rasvahappoesterin tuottaminen |
| PCT/FI2008/050495 WO2009030820A1 (en) | 2007-09-07 | 2008-09-05 | Production of fatty acid and fatty acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2698642A1 true CA2698642A1 (en) | 2009-03-12 |
Family
ID=38572953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2698642A Abandoned CA2698642A1 (en) | 2007-09-07 | 2008-09-05 | Production of fatty acid and fatty acid ester |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP2188356A1 (enExample) |
| JP (1) | JP5620818B2 (enExample) |
| KR (1) | KR101512375B1 (enExample) |
| CN (1) | CN101896590B (enExample) |
| AP (1) | AP2831A (enExample) |
| AU (1) | AU2008294648B2 (enExample) |
| BR (1) | BRPI0816733A2 (enExample) |
| CA (1) | CA2698642A1 (enExample) |
| EA (1) | EA020085B1 (enExample) |
| FI (1) | FI20075619L (enExample) |
| MX (1) | MX2010002615A (enExample) |
| MY (1) | MY152941A (enExample) |
| WO (1) | WO2009030820A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102604851B1 (ko) * | 2015-08-31 | 2023-11-21 | 프라운호퍼 게젤샤프트 쭈르 푀르데룽 데어 안겐반텐 포르슝 에. 베. | 글리세라이드를 함유하는 윤활 혼합물 |
| CN106866370B (zh) * | 2016-12-31 | 2020-10-30 | 衡阳市晨丰生物科技有限公司 | 一种除去粗甘油中脂类的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2327569A (en) * | 1941-03-29 | 1943-08-24 | Refining Inc | Process of refining |
| JP3028282B2 (ja) * | 1996-02-28 | 2000-04-04 | 有限会社染谷商店 | 廃食用油を原資源として精製する重油バーナー用燃料および廃食用油を原資源としての再利用方法 |
| US6129945A (en) * | 1998-12-10 | 2000-10-10 | Michael E. George | Methods to reduce free fatty acids and cholesterol in anhydrous animal fat |
| US6855838B2 (en) * | 2002-01-09 | 2005-02-15 | The United States Of America, As Represented By The Secretary Of Agriculture | Lipid rich compositions, production of lipid rich compositions, production of fatty acid alkyl esters from heterogeneous lipid mixtures |
| CA2436650A1 (en) * | 2003-08-06 | 2005-02-06 | Naturia Inc. | Conjugated linolenic acid (clnatm) compositions: synthesis, purification and uses |
| ATE362506T1 (de) * | 2004-09-21 | 2007-06-15 | Linde Ag | Verfahren zur gewinnung von tallöl oder tallölbrennstoff |
| WO2006088123A1 (ja) * | 2005-02-21 | 2006-08-24 | Kagoshima University | バイオディーゼル燃料の精製方法 |
| JP2007176973A (ja) * | 2005-12-27 | 2007-07-12 | Lion Corp | 軽油代替燃料用の脂肪酸低級アルキルエステルの製造方法 |
-
2007
- 2007-09-07 FI FI20075619A patent/FI20075619L/fi not_active IP Right Cessation
-
2008
- 2008-09-05 MX MX2010002615A patent/MX2010002615A/es active IP Right Grant
- 2008-09-05 CA CA2698642A patent/CA2698642A1/en not_active Abandoned
- 2008-09-05 AU AU2008294648A patent/AU2008294648B2/en not_active Ceased
- 2008-09-05 AP AP2010005210A patent/AP2831A/xx active
- 2008-09-05 KR KR1020107007538A patent/KR101512375B1/ko not_active Expired - Fee Related
- 2008-09-05 CN CN200880114695.9A patent/CN101896590B/zh not_active Expired - Fee Related
- 2008-09-05 WO PCT/FI2008/050495 patent/WO2009030820A1/en not_active Ceased
- 2008-09-05 MY MYPI20100987 patent/MY152941A/en unknown
- 2008-09-05 EA EA201070258A patent/EA020085B1/ru not_active IP Right Cessation
- 2008-09-05 BR BRPI0816733A patent/BRPI0816733A2/pt not_active IP Right Cessation
- 2008-09-05 EP EP08805418A patent/EP2188356A1/en not_active Withdrawn
- 2008-09-05 JP JP2010523549A patent/JP5620818B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101896590B (zh) | 2014-07-30 |
| MY152941A (en) | 2014-12-15 |
| EA020085B1 (ru) | 2014-08-29 |
| KR20100074172A (ko) | 2010-07-01 |
| AU2008294648A8 (en) | 2010-04-22 |
| EA201070258A1 (ru) | 2010-10-29 |
| AP2010005210A0 (en) | 2010-04-30 |
| FI20075619A7 (fi) | 2009-03-08 |
| EP2188356A1 (en) | 2010-05-26 |
| AU2008294648B2 (en) | 2013-09-12 |
| JP2010538140A (ja) | 2010-12-09 |
| BRPI0816733A2 (pt) | 2017-06-06 |
| AU2008294648A1 (en) | 2009-03-12 |
| CN101896590A (zh) | 2010-11-24 |
| FI20075619L (fi) | 2009-03-08 |
| AP2831A (en) | 2014-01-31 |
| JP5620818B2 (ja) | 2014-11-05 |
| WO2009030820A1 (en) | 2009-03-12 |
| FI20075619A0 (fi) | 2007-09-07 |
| KR101512375B1 (ko) | 2015-04-16 |
| MX2010002615A (es) | 2010-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130821 |
|
| FZDE | Discontinued |
Effective date: 20170315 |