CA1304402C - Process for the purification of 2-hydroxynaphthalene-6-carboxylic acid - Google Patents
Process for the purification of 2-hydroxynaphthalene-6-carboxylic acidInfo
- Publication number
- CA1304402C CA1304402C CA000588138A CA588138A CA1304402C CA 1304402 C CA1304402 C CA 1304402C CA 000588138 A CA000588138 A CA 000588138A CA 588138 A CA588138 A CA 588138A CA 1304402 C CA1304402 C CA 1304402C
- Authority
- CA
- Canada
- Prior art keywords
- strength
- acid
- crystallization
- weight aqueous
- aqueous solution
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000000746 purification Methods 0.000 title 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 title claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 40
- 239000007864 aqueous solution Substances 0.000 claims abstract description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001953 recrystallisation Methods 0.000 claims abstract description 15
- 150000002170 ethers Chemical class 0.000 claims abstract description 12
- -1 cyclic aliphatic ethers Chemical class 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 229920000570 polyether Polymers 0.000 claims abstract description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229950011260 betanaphthol Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- RGIAXNBHHDRLEV-UHFFFAOYSA-N COCCOCCOCCOCCOC.COCCOCCOCCOC Chemical compound COCCOCCOCCOCCOC.COCCOCCOCCOC RGIAXNBHHDRLEV-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000007065 Kolbe-Schmitt synthesis reaction Methods 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/02—Saturated compounds containing hydroxy or O-metal groups
- C07C62/06—Saturated compounds containing hydroxy or O-metal groups polycyclic
-
- 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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
- C07C65/11—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic with carboxyl groups on a condensed ring system containing two rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3800989.7 | 1988-01-15 | ||
| DE3800989A DE3800989A1 (de) | 1988-01-15 | 1988-01-15 | Verfahren zur reinigung von 2-hydroxy-naphthalin-6-carbonsaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1304402C true CA1304402C (en) | 1992-06-30 |
Family
ID=6345329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000588138A Expired - Fee Related CA1304402C (en) | 1988-01-15 | 1989-01-13 | Process for the purification of 2-hydroxynaphthalene-6-carboxylic acid |
Country Status (9)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3815929A1 (de) * | 1988-05-10 | 1989-11-23 | Hoechst Ag | Dioxan-addukt der 2-hydroxy-naphthalin-6-carbonsaeure und verfahren zu seiner herstellung |
| DE3842712A1 (de) * | 1988-12-19 | 1990-07-05 | Hoechst Ag | Dioxan-addukte aromatischer meta- oder para-hydroxycarbonsaeuren und verfahren zu ihrer herstellung |
| CA2209992C (en) * | 1995-11-13 | 2004-09-28 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Method of separation and purification of hydroxynaphthalenecarboxylic acids |
| JPH10120624A (ja) * | 1996-10-18 | 1998-05-12 | Sugai Kagaku Kogyo Kk | ２−ヒドロキシナフタレン−６−カルボン酸の精製方法 |
| JPH10265434A (ja) * | 1997-03-21 | 1998-10-06 | Ueno Seiyaku Oyo Kenkyusho:Kk | 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 |
| TW527451B (en) | 1999-08-24 | 2003-04-11 | Ueno Seiyaku Oyo Kenkyujo Kk | Columnar crystals of 6-hydroxy-2-naphthoic acid and process for manufacturing the same |
| CN102173988B (zh) * | 2011-03-25 | 2013-05-01 | 衢州英特高分子材料有限公司 | 一种6-羟基-2-萘甲酸的纯化方法 |
| CN102659576A (zh) * | 2012-05-02 | 2012-09-12 | 苏州思睿屹新材料股份有限公司 | 2-羟基-6-萘甲酸的精制方法 |
| US12310378B2 (en) | 2020-06-29 | 2025-05-27 | Jbt Marel Corporation | Produce processing dosing system |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1593816A (en) * | 1924-08-16 | 1926-07-27 | Grasselli Dyestuffs Corp | Making 2-hydroxy-naphthalene-6-carboxylic acid |
| DE436524C (de) * | 1924-08-17 | 1926-11-03 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von 2-Oxynaphthalin-6-carbonsaeure |
| GB257815A (en) * | 1926-01-28 | 1926-09-09 | Ig Farbenindustrie Ag | Manufacture of 2-oxynaphthalene-6-carboxylic acid |
| US2132356A (en) * | 1937-04-29 | 1938-10-04 | Calco Chemical Co Inc | Carboxylation of alkali metal salts of phenols |
| US2287864A (en) * | 1940-10-28 | 1942-06-30 | Heyden Chemical Corp | Beta oxy naphthoic acid and process for preparing the same |
| DE2332064C2 (de) * | 1973-06-23 | 1983-11-10 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 2-Hydroxy-naphthalin-3-carbonsäure |
| CH599096A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-06-04 | 1978-05-12 | Hoechst Ag | |
| FR2446450A1 (fr) * | 1979-01-09 | 1980-08-08 | Bel Hamri Bernard | Capteur solaire prismatique |
| FR2466450A1 (fr) * | 1979-10-01 | 1981-04-10 | Fabre Sa Pierre | Procede industriel de purification et d'obtention d'itanoxone de qualite pharmaceutique |
| US4287357A (en) * | 1980-03-06 | 1981-09-01 | American Cyanamid Company | Process for the production of 6-hydroxy-2-naphthoic acid |
| US4374262A (en) * | 1980-10-06 | 1983-02-15 | Celanese Corporation | Preparation of hydroxy aromatic carboxylic acids and ester derivatives thereof |
| JPS5795939A (en) * | 1980-12-08 | 1982-06-15 | Ueno Seiyaku Oyo Kenkyusho:Kk | Preparation of 2-hydroxynaphthalene-6-carboxylic acid |
| JPS5935911B2 (ja) * | 1981-12-07 | 1984-08-31 | 株式会社上野製薬応用研究所 | ２−ヒドロキシナフタリン−６−カルボン酸の選択的製法 |
| US4393191A (en) * | 1982-03-08 | 1983-07-12 | Celanese Corporation | Preparation of aromatic polyesters by direct self-condensation of aromatic hydroxy acids |
| JPS61257942A (ja) * | 1985-05-10 | 1986-11-15 | Kureha Chem Ind Co Ltd | ６−ヒドロキシ−２−ナフトエ酸の製造方法 |
-
1988
- 1988-01-15 DE DE3800989A patent/DE3800989A1/de not_active Withdrawn
- 1988-12-27 IN IN1067/CAL/88A patent/IN171007B/en unknown
-
1989
- 1989-01-07 EP EP89100236A patent/EP0325925B1/de not_active Expired - Lifetime
- 1989-01-07 DE DE8989100236T patent/DE58900223D1/de not_active Expired - Fee Related
- 1989-01-12 US US07/296,441 patent/US4916257A/en not_active Expired - Fee Related
- 1989-01-13 CA CA000588138A patent/CA1304402C/en not_active Expired - Fee Related
- 1989-01-13 BR BR898900146A patent/BR8900146A/pt unknown
- 1989-01-13 KR KR1019890000291A patent/KR970006885B1/ko not_active Expired - Fee Related
- 1989-01-13 MX MX014551A patent/MX169972B/es unknown
- 1989-01-13 JP JP1005044A patent/JP2695223B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| MX169972B (es) | 1993-08-03 |
| US4916257A (en) | 1990-04-10 |
| EP0325925A1 (de) | 1989-08-02 |
| BR8900146A (pt) | 1989-09-12 |
| IN171007B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-06-27 |
| KR890011817A (ko) | 1989-08-22 |
| DE3800989A1 (de) | 1989-07-27 |
| KR970006885B1 (ko) | 1997-04-30 |
| JPH01216955A (ja) | 1989-08-30 |
| EP0325925B1 (de) | 1991-08-21 |
| DE58900223D1 (de) | 1991-09-26 |
| JP2695223B2 (ja) | 1997-12-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |