JPH10265434A - ヒドロキシナフタレンカルボン酸類のアルカリ金属塩の分離精製法 - Google Patents
ヒドロキシナフタレンカルボン酸類のアルカリ金属塩の分離精製法Info
- Publication number
- JPH10265434A JPH10265434A JP9067823A JP6782397A JPH10265434A JP H10265434 A JPH10265434 A JP H10265434A JP 9067823 A JP9067823 A JP 9067823A JP 6782397 A JP6782397 A JP 6782397A JP H10265434 A JPH10265434 A JP H10265434A
- Authority
- JP
- Japan
- Prior art keywords
- water
- salt
- bon3
- alkali metal
- bon6
- 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- Withdrawn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
- 150000003839 salts Chemical class 0.000 title claims abstract description 87
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000000926 separation method Methods 0.000 title claims description 8
- 238000000746 purification Methods 0.000 title claims description 6
- 239000003513 alkali Substances 0.000 title abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000003463 adsorbent Substances 0.000 claims abstract description 43
- 239000003960 organic solvent Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920001577 copolymer Polymers 0.000 claims abstract description 8
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 39
- -1 alkali metal salt Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 34
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 51
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 abstract description 15
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract description 15
- 239000000126 substance Substances 0.000 abstract description 12
- 239000011148 porous material Substances 0.000 abstract description 9
- 230000003472 neutralizing effect Effects 0.000 abstract description 4
- 239000012046 mixed solvent Substances 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- 239000000243 solution Substances 0.000 description 33
- 101100218966 Arabidopsis thaliana BON3 gene Proteins 0.000 description 30
- 238000011084 recovery Methods 0.000 description 30
- 230000000052 comparative effect Effects 0.000 description 19
- 239000011734 sodium Substances 0.000 description 10
- 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 6
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 239000003729 cation exchange resin Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229950011260 betanaphthol Drugs 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- TVBXXOVRWRDFMB-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-dicarboxylic acid Chemical compound C1=C(O)C(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 TVBXXOVRWRDFMB-UHFFFAOYSA-N 0.000 description 1
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101001055216 Homo sapiens Interleukin-9 Proteins 0.000 description 1
- 102100026871 Interleukin-9 Human genes 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 238000006085 Schmidt reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- VGDWQWYWJNWOMT-UHFFFAOYSA-L dipotassium;7-carboxy-6-oxidonaphthalene-2-carboxylate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=C2C=C([O-])C(C(=O)O)=CC2=C1 VGDWQWYWJNWOMT-UHFFFAOYSA-L 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- WFJDQCKENFCMKN-UHFFFAOYSA-M potassium;3-hydroxynaphthalene-2-carboxylate Chemical compound [K+].C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 WFJDQCKENFCMKN-UHFFFAOYSA-M 0.000 description 1
- OBNIFGYZZBTPPR-UHFFFAOYSA-M potassium;6-hydroxynaphthalene-2-carboxylate Chemical compound [K+].C1=C(C([O-])=O)C=CC2=CC(O)=CC=C21 OBNIFGYZZBTPPR-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 239000003643 water by type Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9067823A JPH10265434A (ja) | 1997-03-21 | 1997-03-21 | ヒドロキシナフタレンカルボン酸類のアルカリ金属塩の分離精製法 |
| PCT/JP1998/001167 WO1998042651A1 (en) | 1997-03-21 | 1998-03-19 | Process for separating and purifying alkali metal salts of hydroxynaphthalenecarboxylic acids |
| US09/194,019 US6194608B1 (en) | 1997-03-21 | 1998-03-19 | Process for separating and purifying alkali metal salts of hydroxynaphthalenecarboxylic acids |
| CN98800671A CN1226883A (zh) | 1997-03-21 | 1998-03-19 | 羟基萘羧酸类的碱金属盐分离纯化法 |
| DE69815019T DE69815019T2 (de) | 1997-03-21 | 1998-03-19 | Verfahren zur abtrennung und reinigung von alkalimetallsalzen von hydroxynaphthalincarbonsäuren |
| AT98909752T ATE241586T1 (de) | 1997-03-21 | 1998-03-19 | Verfahren zur abtrennung und reinigung von alkalimetallsalzen von hydroxynaphthalincarbonsäuren |
| CA002255621A CA2255621A1 (en) | 1997-03-21 | 1998-03-19 | Process for separating and purifying alkali metal salts of hydroxynaphthalenecarboxylic acids |
| EP98909752A EP0913386B1 (en) | 1997-03-21 | 1998-03-19 | Process for separating and purifying alkali metal salts of hydroxynaphthalenecarboxylic acids |
| TW087104146A TW458966B (en) | 1997-03-21 | 1998-03-20 | A method for seperating and purifying hydroxynaphthalene carboxylic acids alkali metal salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9067823A JPH10265434A (ja) | 1997-03-21 | 1997-03-21 | ヒドロキシナフタレンカルボン酸類のアルカリ金属塩の分離精製法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10265434A true JPH10265434A (ja) | 1998-10-06 |
Family
ID=13356061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9067823A Withdrawn JPH10265434A (ja) | 1997-03-21 | 1997-03-21 | ヒドロキシナフタレンカルボン酸類のアルカリ金属塩の分離精製法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6194608B1 (enExample) |
| EP (1) | EP0913386B1 (enExample) |
| JP (1) | JPH10265434A (enExample) |
| CN (1) | CN1226883A (enExample) |
| AT (1) | ATE241586T1 (enExample) |
| CA (1) | CA2255621A1 (enExample) |
| DE (1) | DE69815019T2 (enExample) |
| TW (1) | TW458966B (enExample) |
| WO (1) | WO1998042651A1 (enExample) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH599096A5 (enExample) * | 1974-06-04 | 1978-05-12 | Hoechst Ag | |
| DE2449779A1 (de) * | 1974-10-19 | 1976-04-29 | Basf Ag | Verfahren zur herstellung von 2-hydroxy-naphthalin-3-carbonsaeure |
| JPS5479257A (en) * | 1977-10-26 | 1979-06-25 | Ueno Seiyaku Oyo Kenkyujo Kk | Manufacture of 22hydroxy naphthalenee33 carboxylic acid |
| JPS5535042A (en) * | 1978-09-06 | 1980-03-11 | Ueno Seiyaku Oyo Kenkyusho:Kk | Preparation of 2-hydroxynaphthalene-3-carboxylic acid |
| DE2911667A1 (de) * | 1979-03-24 | 1980-10-02 | Hoechst Ag | Verfahren zur gewinnung von 2-hydroxynaphthalin-3-carbonsaeure aus den umsetzungsgemischen der alkalisalze des 2-hydroxynaphthalins mit kohlendioxid |
| JPS5692245A (en) * | 1979-12-25 | 1981-07-25 | Sumitomo Chem Co Ltd | Production of 2-hydroxynaphthalene-3-carboxylic acid |
| JPS5795939A (en) * | 1980-12-08 | 1982-06-15 | Ueno Seiyaku Oyo Kenkyusho:Kk | Preparation of 2-hydroxynaphthalene-6-carboxylic acid |
| JPS57197244A (en) * | 1981-05-28 | 1982-12-03 | Ueno Seiyaku Oyo Kenkyusho:Kk | Preparation of 2-hydroxynaphthalene-3-carboxylic acid |
| JPS61129566A (ja) * | 1984-11-28 | 1986-06-17 | Wako Pure Chem Ind Ltd | メチル化シクロデキストリン固定相及びこれを用いる液体クロマトグラフイ− |
| DE3800989A1 (de) * | 1988-01-15 | 1989-07-27 | Hoechst Ag | Verfahren zur reinigung von 2-hydroxy-naphthalin-6-carbonsaeure |
| DE3842712A1 (de) * | 1988-12-19 | 1990-07-05 | Hoechst Ag | Dioxan-addukte aromatischer meta- oder para-hydroxycarbonsaeuren und verfahren zu ihrer herstellung |
| JP2866711B2 (ja) * | 1990-06-22 | 1999-03-08 | 三井化学株式会社 | フェノール化合物の分離方法 |
| DE69619100T2 (de) * | 1995-11-13 | 2002-11-14 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo, Osaka | Verfahren zur trennung und reinigung von hydroxynaphthalincarbonsäuren |
-
1997
- 1997-03-21 JP JP9067823A patent/JPH10265434A/ja not_active Withdrawn
-
1998
- 1998-03-19 AT AT98909752T patent/ATE241586T1/de not_active IP Right Cessation
- 1998-03-19 EP EP98909752A patent/EP0913386B1/en not_active Expired - Lifetime
- 1998-03-19 DE DE69815019T patent/DE69815019T2/de not_active Expired - Fee Related
- 1998-03-19 US US09/194,019 patent/US6194608B1/en not_active Expired - Fee Related
- 1998-03-19 WO PCT/JP1998/001167 patent/WO1998042651A1/ja not_active Ceased
- 1998-03-19 CN CN98800671A patent/CN1226883A/zh active Pending
- 1998-03-19 CA CA002255621A patent/CA2255621A1/en not_active Abandoned
- 1998-03-20 TW TW087104146A patent/TW458966B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1226883A (zh) | 1999-08-25 |
| DE69815019D1 (de) | 2003-07-03 |
| ATE241586T1 (de) | 2003-06-15 |
| WO1998042651A1 (en) | 1998-10-01 |
| EP0913386A4 (enExample) | 1999-06-16 |
| DE69815019T2 (de) | 2004-03-25 |
| TW458966B (en) | 2001-10-11 |
| CA2255621A1 (en) | 1998-10-01 |
| EP0913386B1 (en) | 2003-05-28 |
| US6194608B1 (en) | 2001-02-27 |
| EP0913386A1 (en) | 1999-05-06 |
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