CA2688830A1 - Separation of citric acid from gluconic acid in fermentation broth using a weakly or strongly basic anionic exchange resin adsorbent - Google Patents
Separation of citric acid from gluconic acid in fermentation broth using a weakly or strongly basic anionic exchange resin adsorbent Download PDFInfo
- Publication number
- CA2688830A1 CA2688830A1 CA2688830A CA2688830A CA2688830A1 CA 2688830 A1 CA2688830 A1 CA 2688830A1 CA 2688830 A CA2688830 A CA 2688830A CA 2688830 A CA2688830 A CA 2688830A CA 2688830 A1 CA2688830 A1 CA 2688830A1
- Authority
- CA
- Canada
- Prior art keywords
- zone
- citric acid
- adsorbent
- resin
- desorbent
- 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title claims abstract description 273
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 title claims abstract description 39
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000000174 gluconic acid Substances 0.000 title claims abstract description 27
- 235000012208 gluconic acid Nutrition 0.000 title claims abstract description 27
- 238000000855 fermentation Methods 0.000 title claims abstract description 26
- 230000004151 fermentation Effects 0.000 title claims abstract description 26
- 239000003957 anion exchange resin Substances 0.000 title claims abstract description 20
- 238000000926 separation method Methods 0.000 title claims description 42
- 239000003463 adsorbent Substances 0.000 title abstract description 132
- 229920005989 resin Polymers 0.000 claims abstract description 36
- 239000011347 resin Substances 0.000 claims abstract description 36
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000011159 matrix material Substances 0.000 claims abstract description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910001868 water Inorganic materials 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 65
- 230000008569 process Effects 0.000 claims description 55
- 238000001179 sorption measurement Methods 0.000 claims description 39
- 238000003795 desorption Methods 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000011144 upstream manufacturing Methods 0.000 claims description 18
- 150000001720 carbohydrates Chemical class 0.000 claims description 17
- 235000014633 carbohydrates Nutrition 0.000 claims description 17
- 239000012530 fluid Substances 0.000 claims description 17
- 238000000746 purification Methods 0.000 claims description 15
- 230000000274 adsorptive effect Effects 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- 229920000178 Acrylic resin Polymers 0.000 claims description 6
- 239000004925 Acrylic resin Substances 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 238000006073 displacement reaction Methods 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims 2
- 235000015165 citric acid Nutrition 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 1
- 229920005990 polystyrene resin Polymers 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 46
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 18
- 229940091181 aconitic acid Drugs 0.000 description 18
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 18
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 17
- 239000011148 porous material Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 229920001429 chelating resin Polymers 0.000 description 13
- 239000011800 void material Substances 0.000 description 13
- 239000004793 Polystyrene Substances 0.000 description 12
- 235000010633 broth Nutrition 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- 239000003456 ion exchange resin Substances 0.000 description 10
- 229920003303 ion-exchange polymer Polymers 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 230000014759 maintenance of location Effects 0.000 description 10
- 108090000623 proteins and genes Proteins 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- -1 aconitic acid carbohydrates Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001962 electrophoresis Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 description 6
- 239000000700 radioactive tracer Substances 0.000 description 6
- 239000001257 hydrogen Chemical group 0.000 description 5
- 229910052739 hydrogen Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical group [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 231100000647 material safety data sheet Toxicity 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 235000013379 molasses Nutrition 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 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 description 1
- WBHAUHHMPXBZCQ-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound COC1=CC=CC(C)=C1O WBHAUHHMPXBZCQ-UHFFFAOYSA-N 0.000 description 1
- APCLRHPWFCQIMG-UHFFFAOYSA-N 4-(5,6-dimethoxy-1-benzothiophen-2-yl)-4-oxobutanoic acid Chemical compound C1=C(OC)C(OC)=CC2=C1SC(C(=O)CCC(O)=O)=C2 APCLRHPWFCQIMG-UHFFFAOYSA-N 0.000 description 1
- 108091006522 Anion exchangers Proteins 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229940125791 MSA-2 Drugs 0.000 description 1
- 108010057081 Merozoite Surface Protein 1 Proteins 0.000 description 1
- 101710162106 Merozoite surface antigen 2 Proteins 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000010919 dye waste Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2007/070731 WO2008150298A1 (en) | 2007-06-08 | 2007-06-08 | Separation of citric acid from gluconic acid in fermentation broth using a weakly or strongly basic anionic exchange resin adsorbent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2688830A1 true CA2688830A1 (en) | 2008-12-11 |
Family
ID=40093962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2688830A Abandoned CA2688830A1 (en) | 2007-06-08 | 2007-06-08 | Separation of citric acid from gluconic acid in fermentation broth using a weakly or strongly basic anionic exchange resin adsorbent |
Country Status (4)
| Country | Link |
|---|---|
| CN (1) | CN101679190A (de) |
| AT (1) | AT509134A1 (de) |
| CA (1) | CA2688830A1 (de) |
| WO (1) | WO2008150298A1 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249897A (zh) * | 2011-05-10 | 2011-11-23 | 安徽丰原生物化学股份有限公司 | 一种柠檬酸母液的处理方法 |
| CN103058848B (zh) * | 2012-11-01 | 2016-04-13 | 南京工业大学 | 一种拟均相弱碱性阴离子交换树脂分离有机酸的方法 |
| CN103008026B (zh) * | 2012-11-27 | 2015-12-23 | 安徽皖东化工有限公司 | 强碱性丙烯酸系阴离子交换树脂的制备方法 |
| CN104744241A (zh) * | 2013-12-30 | 2015-07-01 | 中粮营养健康研究院有限公司 | 一种从柠檬酸发酵液中提纯柠檬酸的方法 |
| WO2017103654A1 (en) * | 2015-12-16 | 2017-06-22 | The Petroleum Institute | Calcium alginate adsorbents |
| CN107445249B (zh) * | 2017-09-04 | 2020-03-20 | 南京大学盐城环保技术与工程研究院 | 一种两级树脂互相强化去除废水中有机物和硝态氮的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068419A (en) * | 1986-12-18 | 1991-11-26 | Uop | Separation of an organic acid from a fermentation broth with an anionic polymeric adsorbent |
| FI942403A (fi) * | 1994-05-24 | 1995-11-25 | Cultor Oy | Menetelmä orgaanisen hapon tai sen suolan valmistamiseksi |
-
2007
- 2007-06-08 AT AT0955807A patent/AT509134A1/de not_active Application Discontinuation
- 2007-06-08 CA CA2688830A patent/CA2688830A1/en not_active Abandoned
- 2007-06-08 WO PCT/US2007/070731 patent/WO2008150298A1/en active Application Filing
- 2007-06-08 CN CN200780053275A patent/CN101679190A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008150298A1 (en) | 2008-12-11 |
| CN101679190A (zh) | 2010-03-24 |
| AT509134A1 (de) | 2011-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |