JP4995522B2 - 有機酸からのヨウ素化合物除去方法 - Google Patents
有機酸からのヨウ素化合物除去方法 Download PDFInfo
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- JP4995522B2 JP4995522B2 JP2006258437A JP2006258437A JP4995522B2 JP 4995522 B2 JP4995522 B2 JP 4995522B2 JP 2006258437 A JP2006258437 A JP 2006258437A JP 2006258437 A JP2006258437 A JP 2006258437A JP 4995522 B2 JP4995522 B2 JP 4995522B2
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- silver
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- resin
- cation exchange
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- 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.)
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- 150000002497 iodine compounds Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 23
- 150000007524 organic acids Chemical class 0.000 title claims description 17
- 235000005985 organic acids Nutrition 0.000 title description 3
- 229910052709 silver Inorganic materials 0.000 claims description 50
- 239000004332 silver Substances 0.000 claims description 50
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
- 239000002245 particle Substances 0.000 claims description 36
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 25
- 239000003729 cation exchange resin Substances 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 22
- 239000011148 porous material Substances 0.000 claims description 19
- 239000012535 impurity Substances 0.000 claims description 5
- 150000001351 alkyl iodides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 51
- 238000001179 sorption measurement Methods 0.000 description 24
- 239000003463 adsorbent Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 230000006315 carbonylation Effects 0.000 description 4
- 238000005810 carbonylation reaction Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021612 Silver iodide Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003284 rhodium compounds Chemical class 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005264 electron capture Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Catalysts (AREA)
Description
d=(4×103/S)×(1/da−1/ds)
d :平均細孔径(nm)
S :BET比表面積(m2/g)
da:見かけ密度(g/mL)
ds:真密度(g/mL)
以下に示す陽イオン交換樹脂A〜Fを用意し、吸着材を調製するためのベース樹脂として用いた。
A.ロームアンドハース社製の陽イオン交換樹脂アンバーリスト15(平均粒径0.68mm、平均細孔径24nm)、
B.上記アンバーリスト15を篩分けして平均粒径を0.55mmとしたもの、
C.本発明者が新たに合成した粒状陽イオン交換樹脂(平均粒径0.42mm、平均細孔径24nm)、
D.本発明者が新たに合成した粒状陽イオン交換樹脂(平均粒径0.36mm、平均細孔径24nm)、
E.三菱化学社製の陽イオン交換樹脂ダイヤイオンRCP160M(平均細孔径10nm)を篩分けして平均粒径を0.52mmとしたもの、
F.ロームアンドハース社製のアンバーリストXH2071(平均細孔径30nm)を篩分けして平均粒径を0.52nmとしたもの。
上記A〜Fの樹脂の総イオン交換容量に対し所定の銀交換率(30〜90%)になるように銀を担持させて吸着材を調製した。
各通液試験においては、上記(1)で調製した吸着材5mLをカラム(10mmΦ×100mmH)に充填し、これにヨウ化デシル(C10H21I)を25ppm含有した酢酸を60mL/時(LHSV=12)の速度で通液した。このとき、吸着塔の外部に温水を循環することにより、所定の温度に調整した。吸着塔出口のヨウ化デシル濃度を電子捕獲型検出器付ガスクロマトグラフィ(ECD−GC)で測定し、10ppbに達するまでの時間を破過時間とした。また、破過するまでに通液した液量からヨウ化デシル吸着量(モル数)を求め、銀担持量(モル数)に対する割合を求めて銀利用率(%)とした。
Claims (2)
- 不純物として炭素数10〜12の低級ヨウ化アルキルを含む有機酸を、銀を担持した陽イオン交換樹脂の充填層に50℃以下で通液することにより、該有機酸からヨウ素化合物を吸着除去する方法であって、該陽イオン交換樹脂が、平均粒径0.3〜0.6mm、平均細孔径15〜28nmのマクロポーラス型樹脂であって、その活性部位の40〜60%が銀に置換されたものであることを特徴とする方法。
- 該有機酸が酢酸である請求項1記載の方法。
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006258437A JP4995522B2 (ja) | 2006-09-25 | 2006-09-25 | 有機酸からのヨウ素化合物除去方法 |
CN2007800344572A CN101516822B (zh) | 2006-09-25 | 2007-06-29 | 从有机酸除去碘化合物的方法 |
KR1020097005147A KR101067233B1 (ko) | 2006-09-25 | 2007-06-29 | 유기산으로부터의 요오드화 화합물의 제거 방법 |
PCT/JP2007/063513 WO2008038446A1 (en) | 2006-09-25 | 2007-06-29 | Method for removing iodide compound from organic acid |
RU2009115647/04A RU2440968C2 (ru) | 2006-09-25 | 2007-06-29 | Способ удаления йодидного соединения из органической кислоты |
BRPI0716953A BRPI0716953B1 (pt) | 2006-09-25 | 2007-06-29 | método para adsorver e remover um composto de iodeto de um ácido orgânico |
CA2664293A CA2664293C (en) | 2006-09-25 | 2007-06-29 | Method for removing iodide compound from organic acid |
AU2007301397A AU2007301397B2 (en) | 2006-09-25 | 2007-06-29 | Method for removing iodide compound from organic acid |
PL07790454T PL2066614T3 (pl) | 2006-09-25 | 2007-06-29 | Sposób usuwania związku jodkowego z kwasu organicznego |
EP07790454.8A EP2066614B1 (en) | 2006-09-25 | 2007-06-29 | Method for removing iodide compound from organic acid |
US12/441,476 US7985878B2 (en) | 2006-09-25 | 2007-06-29 | Method for removing iodide compound from organic acid |
TW096126385A TWI422571B (zh) | 2006-09-25 | 2007-07-19 | 由醋酸產物移除碘化合物之方法 |
ZA2009/01512A ZA200901512B (en) | 2006-09-25 | 2009-03-03 | Method for removing iodide compound from organic acid |
MYPI20090908A MY145420A (en) | 2006-09-25 | 2009-03-05 | Method for removing iodide compound from organic acid |
NO20091108A NO342345B1 (no) | 2006-09-25 | 2009-03-13 | Fremgangsmåte for fjerning av jodidforbindelse om har 1 til 12 karbonatomer, eller en blanding derav fra eddiksyre |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006258437A JP4995522B2 (ja) | 2006-09-25 | 2006-09-25 | 有機酸からのヨウ素化合物除去方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008074808A JP2008074808A (ja) | 2008-04-03 |
JP4995522B2 true JP4995522B2 (ja) | 2012-08-08 |
Family
ID=38515731
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006258437A Active JP4995522B2 (ja) | 2006-09-25 | 2006-09-25 | 有機酸からのヨウ素化合物除去方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US7985878B2 (ja) |
EP (1) | EP2066614B1 (ja) |
JP (1) | JP4995522B2 (ja) |
KR (1) | KR101067233B1 (ja) |
CN (1) | CN101516822B (ja) |
AU (1) | AU2007301397B2 (ja) |
BR (1) | BRPI0716953B1 (ja) |
CA (1) | CA2664293C (ja) |
MY (1) | MY145420A (ja) |
NO (1) | NO342345B1 (ja) |
PL (1) | PL2066614T3 (ja) |
RU (1) | RU2440968C2 (ja) |
TW (1) | TWI422571B (ja) |
WO (1) | WO2008038446A1 (ja) |
ZA (1) | ZA200901512B (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5009478B2 (ja) * | 2000-08-25 | 2012-08-22 | 株式会社カネカ | 細菌毒素の吸着材、その吸着除去方法および該吸着材を充填してなる吸着器 |
JP4977592B2 (ja) * | 2007-12-14 | 2012-07-18 | オルガノ株式会社 | よう素含有廃液からのよう素回収方法およびよう素回収装置 |
US7588690B1 (en) * | 2009-02-10 | 2009-09-15 | The Purolite Company | Method of iodide removal |
US20110086929A1 (en) * | 2009-10-13 | 2011-04-14 | Brotech Corporation, doing business as The Purolite Company | Method of iodide removal |
MX2013007647A (es) * | 2010-12-30 | 2013-08-01 | Celanese Int Corp | Purificacion de torrentes de productos de acido acetico. |
CN104001485B (zh) * | 2014-05-22 | 2015-10-21 | 宁波工程学院 | 一种改性大孔树脂吸附剂及去除盐水中碘的处理方法 |
US9505691B2 (en) | 2014-10-02 | 2016-11-29 | Celanese International Corporation | Process for producing acetic acid |
US9487464B2 (en) | 2015-01-30 | 2016-11-08 | Celanese International Corporation | Processes for producing acetic acid |
US9561994B2 (en) | 2015-01-30 | 2017-02-07 | Celanese International Corporation | Processes for producing acetic acid |
EP3250545B1 (en) | 2015-01-30 | 2019-06-26 | Celanese International Corporation | Processes for producing acetic acid |
CN107207392B (zh) | 2015-01-30 | 2021-06-08 | 国际人造丝公司 | 生产乙酸的方法 |
US9512056B2 (en) | 2015-02-04 | 2016-12-06 | Celanese International Corporation | Process to control HI concentration in residuum stream |
US9505696B2 (en) | 2015-02-04 | 2016-11-29 | Celanese International Corporation | Process to control HI concentration in residuum stream |
US10413840B2 (en) | 2015-02-04 | 2019-09-17 | Celanese International Coporation | Process to control HI concentration in residuum stream |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4615806B1 (en) * | 1985-03-07 | 1994-05-03 | Hoechst Co American | Removal of iodide compounds from non-aqueous organic media |
JPS62153248A (ja) * | 1985-12-26 | 1987-07-08 | Kyowa Yuka Kk | 酢酸エチルの精製法 |
DE3869488D1 (de) * | 1987-06-24 | 1992-04-30 | Union Carbide Corp | Entfernung von halogeniden von karbonsaeuren. |
GB9023634D0 (en) * | 1990-10-31 | 1990-12-12 | British Petroleum Co Plc | Process for purifying acetic acid and/or acetic anhydride |
JP2548469B2 (ja) * | 1991-09-30 | 1996-10-30 | ワイケイケイ株式会社 | バックル |
US5220058A (en) * | 1991-09-30 | 1993-06-15 | Union Carbide Chemicals & Plastics Technology Corporation | Iodide removal process |
JP3306227B2 (ja) * | 1994-07-06 | 2002-07-24 | ダイセル化学工業株式会社 | 酢酸および/または無水酢酸の製造法 |
US5625095A (en) * | 1994-06-15 | 1997-04-29 | Daicel Chemical Industries, Ltd. | Process for producing high purity acetic acid |
JP3281258B2 (ja) * | 1996-04-26 | 2002-05-13 | ダイセル化学工業株式会社 | 有機媒質中に含まれるヨウ素化合物を除去する際の運転方法 |
US6211408B1 (en) * | 1999-03-24 | 2001-04-03 | Celanese International Corporation | Method of removing iodides from non-aqueous organic media utilizing silver or mercury exchanged macroporous organofunctional polysiloxane resins |
US6657078B2 (en) * | 2001-02-07 | 2003-12-02 | Celanese International Corporation | Low energy carbonylation process |
JP4502729B2 (ja) * | 2004-07-02 | 2010-07-14 | 千代田化工建設株式会社 | 有機酸からのヨウ素除去方法 |
-
2006
- 2006-09-25 JP JP2006258437A patent/JP4995522B2/ja active Active
-
2007
- 2007-06-29 BR BRPI0716953A patent/BRPI0716953B1/pt active IP Right Grant
- 2007-06-29 KR KR1020097005147A patent/KR101067233B1/ko active IP Right Grant
- 2007-06-29 EP EP07790454.8A patent/EP2066614B1/en active Active
- 2007-06-29 RU RU2009115647/04A patent/RU2440968C2/ru active
- 2007-06-29 CN CN2007800344572A patent/CN101516822B/zh active Active
- 2007-06-29 PL PL07790454T patent/PL2066614T3/pl unknown
- 2007-06-29 US US12/441,476 patent/US7985878B2/en active Active
- 2007-06-29 CA CA2664293A patent/CA2664293C/en active Active
- 2007-06-29 WO PCT/JP2007/063513 patent/WO2008038446A1/en active Search and Examination
- 2007-06-29 AU AU2007301397A patent/AU2007301397B2/en active Active
- 2007-07-19 TW TW096126385A patent/TWI422571B/zh active
-
2009
- 2009-03-03 ZA ZA2009/01512A patent/ZA200901512B/en unknown
- 2009-03-05 MY MYPI20090908A patent/MY145420A/en unknown
- 2009-03-13 NO NO20091108A patent/NO342345B1/no unknown
Also Published As
Publication number | Publication date |
---|---|
TWI422571B (zh) | 2014-01-11 |
CN101516822A (zh) | 2009-08-26 |
JP2008074808A (ja) | 2008-04-03 |
CA2664293C (en) | 2011-11-22 |
US20090259072A1 (en) | 2009-10-15 |
RU2009115647A (ru) | 2010-11-10 |
TW200815335A (en) | 2008-04-01 |
EP2066614B1 (en) | 2014-09-17 |
BRPI0716953B1 (pt) | 2016-10-11 |
WO2008038446A1 (en) | 2008-04-03 |
KR101067233B1 (ko) | 2011-09-22 |
CN101516822B (zh) | 2013-04-24 |
BRPI0716953A2 (pt) | 2013-02-19 |
US7985878B2 (en) | 2011-07-26 |
RU2440968C2 (ru) | 2012-01-27 |
ZA200901512B (en) | 2010-02-24 |
PL2066614T3 (pl) | 2015-03-31 |
AU2007301397A1 (en) | 2008-04-03 |
KR20090052352A (ko) | 2009-05-25 |
MY145420A (en) | 2012-02-15 |
AU2007301397B2 (en) | 2012-09-13 |
NO342345B1 (no) | 2018-05-07 |
EP2066614A1 (en) | 2009-06-10 |
CA2664293A1 (en) | 2008-04-03 |
NO20091108L (no) | 2009-03-13 |
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