CA1337553C - Process for purifying 2-(4-isobutylphenyl)-propionic acid - Google Patents
Process for purifying 2-(4-isobutylphenyl)-propionic acidInfo
- Publication number
- CA1337553C CA1337553C CA000589392A CA589392A CA1337553C CA 1337553 C CA1337553 C CA 1337553C CA 000589392 A CA000589392 A CA 000589392A CA 589392 A CA589392 A CA 589392A CA 1337553 C CA1337553 C CA 1337553C
- Authority
- CA
- Canada
- Prior art keywords
- rectification
- acid
- isobutylphenyl
- impurities
- carried out
- 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 35
- 230000008569 process Effects 0.000 title claims abstract description 27
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 title claims description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 38
- 239000012535 impurity Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 238000000926 separation method Methods 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000012856 packing Methods 0.000 claims description 4
- VLVILBSSXMZZCB-UHFFFAOYSA-N 1-[4-(2-methylpropyl)phenyl]ethanol Chemical compound CC(C)CC1=CC=C(C(C)O)C=C1 VLVILBSSXMZZCB-UHFFFAOYSA-N 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 230000006315 carbonylation Effects 0.000 claims description 3
- 238000005810 carbonylation reaction Methods 0.000 claims description 3
- 239000011552 falling film Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 52
- 238000000354 decomposition reaction Methods 0.000 abstract description 5
- TUZRJGVLAFMQEK-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1.CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 TUZRJGVLAFMQEK-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000000746 purification Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SPBVCQUMYJRBMD-UHFFFAOYSA-N 1-(1-chloroethyl)-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(C(C)Cl)C=C1 SPBVCQUMYJRBMD-UHFFFAOYSA-N 0.000 description 1
- KEAGRYYGYWZVPC-UHFFFAOYSA-N 1-[4-(2-methylpropyl)phenyl]ethanone Chemical compound CC(C)CC1=CC=C(C(C)=O)C=C1 KEAGRYYGYWZVPC-UHFFFAOYSA-N 0.000 description 1
- VTMSSJKVUVVWNJ-UHFFFAOYSA-N 1-ethenyl-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(C=C)C=C1 VTMSSJKVUVVWNJ-UHFFFAOYSA-N 0.000 description 1
- SFVKLYXPBKITCE-UHFFFAOYSA-N 2-[3-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=CC(C(C)C(O)=O)=C1 SFVKLYXPBKITCE-UHFFFAOYSA-N 0.000 description 1
- DYNVRFFVBZVRND-UHFFFAOYSA-N 3-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(CCC(O)=O)C=C1 DYNVRFFVBZVRND-UHFFFAOYSA-N 0.000 description 1
- MAUAHKQOJAFLQH-UHFFFAOYSA-N 4-methylpentan-2-ylbenzene Chemical compound CC(C)CC(C)C1=CC=CC=C1 MAUAHKQOJAFLQH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JLNMSNDDYBZCIB-UHFFFAOYSA-N OOOOS Chemical compound OOOOS JLNMSNDDYBZCIB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 amine salts Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HXTFUVWJFLDLJP-UHFFFAOYSA-N ethyl 2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound CCOC(=O)C(C)C1=CC=C(CC(C)C)C=C1 HXTFUVWJFLDLJP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000013386 optimize process Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- 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
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
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 |
|---|---|---|---|
| DEP3802619.8 | 1988-01-29 | ||
| DE3802619A DE3802619C1 (en)van) | 1988-01-29 | 1988-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1337553C true CA1337553C (en) | 1995-11-14 |
Family
ID=6346221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000589392A Expired - Fee Related CA1337553C (en) | 1988-01-29 | 1989-01-27 | Process for purifying 2-(4-isobutylphenyl)-propionic acid |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0326027B1 (en)van) |
| JP (1) | JP2688515B2 (en)van) |
| KR (1) | KR0129753B1 (en)van) |
| CN (1) | CN1025609C (en)van) |
| AR (1) | AR244196A1 (en)van) |
| AT (1) | ATE83766T1 (en)van) |
| AU (1) | AU607837B2 (en)van) |
| CA (1) | CA1337553C (en)van) |
| DD (1) | DD278778A5 (en)van) |
| DE (2) | DE3802619C1 (en)van) |
| DK (1) | DK175685B1 (en)van) |
| ES (1) | ES2042811T3 (en)van) |
| FI (1) | FI90656C (en)van) |
| GR (1) | GR3007235T3 (en)van) |
| HU (1) | HU202172B (en)van) |
| IE (1) | IE63324B1 (en)van) |
| IL (1) | IL89094A (en)van) |
| NO (1) | NO169118C (en)van) |
| NZ (1) | NZ227756A (en)van) |
| PT (1) | PT89535B (en)van) |
| RU (1) | RU1819257C (en)van) |
| ZA (1) | ZA89619B (en)van) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3833448A1 (de) * | 1988-10-01 | 1990-04-12 | Hoechst Ag | Verfahren zur gewinnung von ibuprofen fuer die direkttablettierung |
| DE3833446A1 (de) * | 1988-10-01 | 1990-04-05 | Hoechst Ag | Verfahren zur herstellung von arzneimittelwirkstoff-partikeln mit verbesserten fliess-, lager- und formulierungseigenschaften sowie arzneimittel, die diese arzneimittelwirkstoff-partikeln enthalten |
| US5151551A (en) * | 1990-09-06 | 1992-09-29 | Hoechst Celanese Corporation | Method for purification of ibuprofen comprising mixtures |
| GB0519350D0 (en) | 2005-09-22 | 2005-11-02 | Boots Healthcare Int Ltd | Therapeutic agents |
| CN204505103U (zh) * | 2015-04-14 | 2015-07-29 | 杭州巨星科技股份有限公司 | 蜗轮夹持防松结构及防松活络扳手 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB971700A (en) * | 1961-02-02 | 1964-09-30 | Boots Pure Drug Co Ltd | Anti-Inflammatory Agents |
| US3344045A (en) * | 1964-10-23 | 1967-09-26 | Sun Oil Co | Electrolytic preparation of carboxylic acids |
| HU173576B (hu) * | 1975-06-24 | 1979-06-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija zamehhjonnykh fenil-alkil-karbonovykh kislot |
| DE2557011A1 (de) * | 1975-12-18 | 1977-06-23 | Dynamit Nobel Ag | Verfahren zur herstellung von alpha- arylsubstituierten propionsaeurealkylestern |
| US4694100A (en) * | 1984-07-14 | 1987-09-15 | Nippon Petrochemicals Company, Ltd. | Method for producing α-(p-isobutylphenyl)propionic acid or its alkyl esters |
-
1988
- 1988-01-29 DE DE3802619A patent/DE3802619C1/de not_active Expired
-
1989
- 1989-01-20 EP EP89100912A patent/EP0326027B1/de not_active Expired - Lifetime
- 1989-01-20 ES ES89100912T patent/ES2042811T3/es not_active Expired - Lifetime
- 1989-01-20 DE DE8989100912T patent/DE58903057D1/de not_active Expired - Fee Related
- 1989-01-20 AT AT89100912T patent/ATE83766T1/de not_active IP Right Cessation
- 1989-01-26 AR AR89313081A patent/AR244196A1/es active
- 1989-01-26 FI FI890386A patent/FI90656C/fi active IP Right Grant
- 1989-01-26 PT PT89535A patent/PT89535B/pt active IP Right Grant
- 1989-01-26 ZA ZA89619A patent/ZA89619B/xx unknown
- 1989-01-27 CN CN89101467A patent/CN1025609C/zh not_active Expired - Fee Related
- 1989-01-27 DK DK198900376A patent/DK175685B1/da not_active IP Right Cessation
- 1989-01-27 HU HU89418A patent/HU202172B/hu not_active IP Right Cessation
- 1989-01-27 JP JP1016525A patent/JP2688515B2/ja not_active Expired - Fee Related
- 1989-01-27 KR KR1019890000868A patent/KR0129753B1/ko not_active Expired - Fee Related
- 1989-01-27 IL IL89094A patent/IL89094A/xx not_active IP Right Cessation
- 1989-01-27 NO NO890344A patent/NO169118C/no unknown
- 1989-01-27 DD DD89325298A patent/DD278778A5/de unknown
- 1989-01-27 AU AU28857/89A patent/AU607837B2/en not_active Ceased
- 1989-01-27 NZ NZ227756A patent/NZ227756A/en unknown
- 1989-01-27 IE IE26889A patent/IE63324B1/en not_active IP Right Cessation
- 1989-01-27 CA CA000589392A patent/CA1337553C/en not_active Expired - Fee Related
- 1989-01-28 RU SU894613357A patent/RU1819257C/ru not_active IP Right Cessation
-
1993
- 1993-03-05 GR GR930400198T patent/GR3007235T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |