KR890014436A - 이부프로펜의 제조방법 - Google Patents
이부프로펜의 제조방법 Download PDFInfo
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- KR890014436A KR890014436A KR1019880002988A KR880002988A KR890014436A KR 890014436 A KR890014436 A KR 890014436A KR 1019880002988 A KR1019880002988 A KR 1019880002988A KR 880002988 A KR880002988 A KR 880002988A KR 890014436 A KR890014436 A KR 890014436A
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- KR
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- Prior art keywords
- hydrogen
- palladium
- ibpe
- molar ratio
- ions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음.
Description
내용없음
Claims (18)
- 최소한 약 500 psig의 일산화탄소 압력과 최소한 약 10℃의 온도에서 하기 (1) - (3)이 존재하는 가운데 산성 수성 매체내에서 1-(4' 이소부틸페닐)에탄올(IBPE)을 일산화탄소로써 카르보닐화 시키는 것으로 구성되는 이부프로펜의 제조방법. (1) 팔라듐 원자가 0-2 이고 팔라듐이 반응매체의 유기상과 혼화할 수 있는 최소한 하나의 산 안정성, 한자리 포스핀 리간드와 착물을 이루는 팔라듐화합물로 근본적으로 구성되는 촉매(팔라듐 대 IBPE의 몰비율이 약 1 : 10,000 미만일때, 팔라듐 화합물 및 리간드내의 인/팔라듐 몰비율은 최소한 약 2 : 1 임) ; (2) 반응 지대에 첨가된 수소이온대 IBPE의 몰비율이 최소한 약 0.15이고 수소이온대 물의 몰비율이 최소한 약 0.026이 되도록, 묽은 수성 용액내에서 본질적으로 완전히 이온화할 수 있는 산에서 해리된 수소 이온 ; 및 (3) 반응 지대에 첨가된 할로겐화 이온 대 IBPE의 몰비율이 최소한 약 0.15가 되도록 해리된 할로겐화 이온.
- 제1항에 있어서, 상기한 리간드가 트리(오르가도)포스핀인 방법.
- 제2항에 있어서, 상기간 리간드가 트리페닐 포스핀인 방법.
- 제3항에 있어서, 상기한 촉매가 팔라듐 비스(트리페닐 포스핀) 디클로로 착물인 방법.
- 제1항에 있어서, 상기한 수소 이온 및 할로겐화 이온의 공급원이 수소 할로겐화물인 방법.
- 제5항에 있어서, 상기한 수소 할로겐화물이 염화 수소인 방법.
- 제5항에 있어서, 상기한 수소 할로겐화물이 브롬화 수소인 방법.
- 제1항에 있어서, 유기용매가 상기한 카르보닐화 반응도중에 존재하고, 상기한 팔라듐이 제로원자가 상태로 시스템에 첨가되는 경우에는 그 용매가 비-탄화수소인 방법.
- 제8항에 있어서, 상기한 유기 용매가 케톤인 방법.
- 제9항에 있어서, 상기한 케톤 메틸 에틸 케톤인 방법.
- 이소부틸벤젠을 프리델-크래프트 촉매의 존재하에서 아세틸화제가 반응시켜, 4' 이소부틸아세토페놀(IBAP)을 제조하고, 상기한 IBAP를 수소화 촉매가 존재하는 가운데 수소로써, 또는 이용가능한 수소를 함유하는 환원제로써 환원시켜, 1-(4' 이소부틸페닐)에탄올(IBPE)을 얻고, 최소한 약 500psig의 일산화탄소 압력과 최소한 약 10℃의 온도에서 하기 (1) -(3)이 존재하는 가운데 산성 수성 매체내에서 상기한 IBPE를 일산화탄소로써 카르보닐화시키는 것으로 구성된 이부프로펜의 제조방법 : (1) 팔라듐의 원자가가 0-2이고 팔라듐이 반응매체의 유기상과 혼화할 수 있는 최소한 하나의 산 안정성, 한자리 포스핀 리간드와 착물을 이루는 팔라듐 화합물로 근본적으로 구성되는 촉매(팔라듐대 IBPE의 몰비율이 약 1 : 10000 미만일때, 상기한 팔라듐 화합물 및 리간드내에 있는 인/팔라듐 몰비율은 최소한 2 : 1임) ; (2) 반응지대에 첨가된 수소이온대 IBPE의 몰비율이 최소한 약 0.15이고 수소이온대 물의 몰비율이 최소한 약 0.026이 되도록 묽은 수성 용액내에서 본질적으로 완전히 이온화 가능한 산에서 해리된 수소이온 ; 및 (3) 반응지대에 첨가된 할로겐화 이온대 IBPE의 몰비율이 최소한 약 0.15가 되도록 해리된 할로겐화 이온.
- 제11항에 있어서, 상기한 촉매가 팔라듐 비스(트리페닐)포스핀 디클로로 착물인 방법.
- 제11항에 있어서, 상기한 수소이온 및 할로겐화 이온의 공급원이 수소 할로겐화물인 방법.
- 제13항에 있어서, 상기한 공급원이 염화수소인 방법.
- 제13항에 있어서, 상기한 공급원이 브롬화수소인 방법.
- 제11항에 있어서, 유기용매가 상기한 카르보닐화 반응 도중에 존재하고, 상기한 팔라듐이 제로원자가 상태로 시스템에 첨가되는 경우에는 그 용매가 비-탄화수소인 방법.
- 제16항에 있어서, 상기한 유기용매가 메틸 에틸 케톤인 방법.
- 최소한 약 500 psig의 일산화탄소 압력과 최소한 약 10℃의 온도에서, 근본적으로 팔라듐 비스(트리페닐포스핀)디클로로 착물로 구성된 촉매, 수소 및 염소화 이온대 첨가된 IBPE의 각 몰비율이 최소한 약 0.2가 되도록, 염화수소로부터 해리된 수소 및 염소화이온, 그리고 용매대 IBPE의 중량비가 최소한 약 1.5가 되게하는 양인 유기용매가 존재하는 가운데, 산성 수성 매체내에서 1-(4' 이소부틸페닐)에탄올(IBPE)을 일산화탄소로써 카르보닐화시키는 것으로 구성되는 이부프로펜 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2851487A | 1987-03-20 | 1987-03-20 | |
US28514 | 1987-03-20 | ||
US028,514 | 1987-03-20 | ||
US15814188A | 1988-03-04 | 1988-03-04 | |
US158141 | 1988-03-04 | ||
US158,141 | 1988-03-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR890014436A true KR890014436A (ko) | 1989-10-23 |
KR960007822B1 KR960007822B1 (ko) | 1996-06-12 |
Family
ID=26703780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019880002988A KR960007822B1 (ko) | 1987-03-20 | 1988-03-19 | 이부프로펜의 제조방법 |
Country Status (22)
Country | Link |
---|---|
EP (1) | EP0284310B1 (ko) |
JP (1) | JPH0686403B2 (ko) |
KR (1) | KR960007822B1 (ko) |
CN (1) | CN1029679C (ko) |
AU (1) | AU620322B2 (ko) |
BR (1) | BR8801238A (ko) |
CA (1) | CA1329396C (ko) |
DE (1) | DE3864713D1 (ko) |
DK (1) | DK148488A (ko) |
ES (1) | ES2026251T3 (ko) |
FI (1) | FI90861C (ko) |
GR (1) | GR3002693T3 (ko) |
HU (1) | HU200983B (ko) |
IE (1) | IE60502B1 (ko) |
IL (1) | IL85736A (ko) |
MX (1) | MX168833B (ko) |
NO (1) | NO169890C (ko) |
NZ (1) | NZ223950A (ko) |
PL (1) | PL153826B1 (ko) |
PT (1) | PT87014B (ko) |
SG (1) | SG22892G (ko) |
YU (1) | YU46539B (ko) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4981995A (en) * | 1987-03-20 | 1991-01-01 | Varadaraj Elango | Method for producing ibuprofen |
EP0337803A1 (en) * | 1988-04-15 | 1989-10-18 | Hoechst Celanese Corporation | Catalyst recycle in the carbonylation of isobutylphenylethanol to ibuprofen |
JP2782080B2 (ja) * | 1989-03-06 | 1998-07-30 | 日本石油化学株式会社 | α―(3―ベンゾイルフェニル)プロピオン酸誘導体の製造方法 |
HU209123B (en) * | 1990-06-04 | 1994-03-28 | Hoechst Celanese Corp | Process for producing 2-(4'-isobutylphenyl)-propionic acid |
US5166418A (en) * | 1990-06-04 | 1992-11-24 | Hoechst Celanese Corporation | Method for producing ibuprofen |
US5179229A (en) * | 1992-04-24 | 1993-01-12 | Hoechst Celanese Corporation | Preparation of 2,2-diorgano-3-arylpropionic acids and esters thereof |
US5315030A (en) * | 1993-09-29 | 1994-05-24 | Ethyl Corporation | Catalytic carbonylation of ethers and thioethers |
US5482596A (en) * | 1994-01-27 | 1996-01-09 | Albemarle Corporation | Mixed ligand catalyst for preparing aryl-substituted aliphatic carboxylic esters |
EP0701987A1 (de) | 1994-09-16 | 1996-03-20 | Cu Chemie Uetikon Ag | Verfahren zur Herstellung von aromatischen Ketonen |
US6268526B1 (en) | 1998-12-16 | 2001-07-31 | Albemarle Corporation | Palladium catalyzed carbonylation process utilizing aromatic substituted alcohols and/or aromatic substituted alkyl halides |
CN1309700C (zh) * | 2005-05-27 | 2007-04-11 | 中国科学院上海有机化学研究所 | 一种制备2-芳基乳酸酯及萘普生、布洛芬的方法 |
CN102329194A (zh) * | 2011-07-15 | 2012-01-25 | 浙江工业大学 | 一种布洛芬中间体对异丁基苯乙醇的制备方法 |
CN103254070B (zh) * | 2013-02-03 | 2014-11-05 | 青岛科技大学 | 一种由1-(4-异丁基苯基)乙醇制备2-(4-异丁基苯基)丙酸酯的方法 |
US20220041533A1 (en) * | 2018-12-03 | 2022-02-10 | Basf Se | Process for producing 1-(4-isobutylphenyl)ethanol by hydrogenation of 1-(4-isobutyl-phenyl)ethanone in the presence of a catalyst composition comprising copper |
CN111689847B (zh) * | 2020-06-12 | 2022-05-17 | 浙江新和成股份有限公司 | 芳基丙酸类化合物的制备方法 |
WO2023073080A1 (en) * | 2021-10-28 | 2023-05-04 | Centre National De La Recherche Scientifique | Process for preparing acyl derivatives |
CN114195633A (zh) * | 2021-12-24 | 2022-03-18 | 浙江新和成股份有限公司 | 一种布洛芬杂质f的合成方法 |
CN116392986B (zh) * | 2023-06-09 | 2023-08-04 | 北京思达流体科技有限公司 | 1-(4-异丁基苯基)乙醇羰基化的连续化生产系统及操作方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL6702884A (ko) * | 1966-03-22 | 1967-09-25 | ||
SE364254B (ko) * | 1967-04-05 | 1974-02-18 | Monsanto Co | |
JPS5995238A (ja) * | 1982-11-19 | 1984-06-01 | Mitsubishi Petrochem Co Ltd | フエニル酢酸誘導体の製造法 |
EP0124160B1 (en) * | 1983-05-02 | 1986-09-17 | Shell Internationale Researchmaatschappij B.V. | A process for the preparation of carboxylic acids and/or esters |
-
1988
- 1988-03-14 CA CA000561404A patent/CA1329396C/en not_active Expired - Fee Related
- 1988-03-14 IL IL85736A patent/IL85736A/xx unknown
- 1988-03-18 ES ES198888302410T patent/ES2026251T3/es not_active Expired - Lifetime
- 1988-03-18 BR BR8801238A patent/BR8801238A/pt not_active IP Right Cessation
- 1988-03-18 EP EP88302410A patent/EP0284310B1/en not_active Expired - Lifetime
- 1988-03-18 PL PL1988271283A patent/PL153826B1/pl unknown
- 1988-03-18 MX MX010825A patent/MX168833B/es unknown
- 1988-03-18 DK DK148488A patent/DK148488A/da not_active Application Discontinuation
- 1988-03-18 PT PT87014A patent/PT87014B/pt not_active IP Right Cessation
- 1988-03-18 DE DE8888302410T patent/DE3864713D1/de not_active Expired - Lifetime
- 1988-03-18 YU YU55188A patent/YU46539B/sh unknown
- 1988-03-18 JP JP63063787A patent/JPH0686403B2/ja not_active Expired - Lifetime
- 1988-03-18 NZ NZ223950A patent/NZ223950A/xx unknown
- 1988-03-18 AU AU13284/88A patent/AU620322B2/en not_active Ceased
- 1988-03-18 NO NO881213A patent/NO169890C/no not_active IP Right Cessation
- 1988-03-18 HU HU881366A patent/HU200983B/hu unknown
- 1988-03-18 FI FI881303A patent/FI90861C/fi not_active IP Right Cessation
- 1988-03-18 IE IE80088A patent/IE60502B1/en not_active IP Right Cessation
- 1988-03-19 KR KR1019880002988A patent/KR960007822B1/ko not_active IP Right Cessation
- 1988-03-19 CN CN88102150A patent/CN1029679C/zh not_active Expired - Lifetime
-
1991
- 1991-09-12 GR GR91400719T patent/GR3002693T3/el unknown
-
1992
- 1992-03-06 SG SG228/92A patent/SG22892G/en unknown
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