EP2188356A1 - Production of fatty acid and fatty acid ester - Google Patents
Production of fatty acid and fatty acid esterInfo
- Publication number
- EP2188356A1 EP2188356A1 EP08805418A EP08805418A EP2188356A1 EP 2188356 A1 EP2188356 A1 EP 2188356A1 EP 08805418 A EP08805418 A EP 08805418A EP 08805418 A EP08805418 A EP 08805418A EP 2188356 A1 EP2188356 A1 EP 2188356A1
- Authority
- EP
- European Patent Office
- 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.)
- Withdrawn
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 48
- 239000000344 soap Substances 0.000 claims description 46
- 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
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000001110 calcium chloride Substances 0.000 claims description 7
- 229910001628 calcium chloride Inorganic materials 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
- 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
- 229940044613 1-propanol Drugs 0.000 description 2
- 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
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 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
Definitions
- the present invention concerns a process for forming a fatty acid, a fatty acid ester or a mixture thereof from a starting material comprising soap, as well as use of the formed mixture.
- Fig. 1 depicts the main execution steps of the process according the invention.
- the fatty acid can be used as such or a fatty acid ester, suitable for biodiesel, can be formed therefrom using a monohydric short-chained alcohol by treating the fatty acid with said alcohol.
- a monohydric short-chained alcohol by treating the fatty acid with said alcohol.
- the acid treatment and the esterification are carried out as an acid catalyzed esterification or by gradually esterifying.
- an HCl-methanol treatment is performed on the soap precipitate at a temperature exceeding the boiling point of methanol, more preferably at over 65°C, most suitably at 80°C.
- the second phase i.e. the organic phase
- the phase containing the salt formed in the esterification into the starting material.
- the aqueous solution containing mineral salts released in the esterification can be recycled to the step of mineral salt treatment of the soap.
- Both the fatty acids and the fatty acid esters formed in the invention can be utilized for the manufacturing of biofuels. They can be used as such or they can be blended with other components, or the acid or ester structures can be degraded using methods known in the art and the double bonds can be saturated, whereby an n-paraffin product is obtained, which on the other hand can be mixed into the other components.
- Example 1 The manufacturing of fatty acid esters
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99301407P | 2007-09-07 | 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 |
|---|---|
| EP2188356A1 true EP2188356A1 (en) | 2010-05-26 |
Family
ID=38572953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP08805418A Withdrawn EP2188356A1 (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
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2009030820A1 * |
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 |
| 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 |
| CA2698642A1 (en) | 2009-03-12 |
| 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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