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ES2121357T3 - Procedimiento para la obtencion de alcoholes y/o aldehidos. - Google Patents

Procedimiento para la obtencion de alcoholes y/o aldehidos.

Info

Publication number
ES2121357T3
ES2121357T3 ES95912212T ES95912212T ES2121357T3 ES 2121357 T3 ES2121357 T3 ES 2121357T3 ES 95912212 T ES95912212 T ES 95912212T ES 95912212 T ES95912212 T ES 95912212T ES 2121357 T3 ES2121357 T3 ES 2121357T3
Authority
ES
Spain
Prior art keywords
stage
hydroformilation
carbonilation
carboxylated
river
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 - Lifetime
Application number
ES95912212T
Other languages
English (en)
Inventor
Heinz-Josef Kneuper
Maik Aron
Frank-Michael Korgitzsch
Michael Nilles
Wolfgang Harder
Michael Roper
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Application granted granted Critical
Publication of ES2121357T3 publication Critical patent/ES2121357T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/20—Carbonyls
    • 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
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
    • B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
    • B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
    • 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
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • 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
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • B01J23/464—Rhodium
    • 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
    • B01J2531/822—Rhodium
    • 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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • 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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • 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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
    • 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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
    • B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

PROCEDIMIENTO PARA LA OBTENCION DE ALDEHIDOS POR HIDROFORMILACION DE OLEFINAS CON MAS DE 3 ATOMOS DE CARBONO, COMPRENDIENDO LA ETAPA DE LA HIDROFORMILACION MEDIANTE UN CATALIZADOR DE RODIO UNIFORMEMENTE DISUELTO EN EL MEDIO DE REACCION, LA RETIRADA DEL CATALIZADOR DE RODIO DEL PRODUCTO DE LA HIDROFORMILACION Y SU RECICLADO A LA ETAPA DE HIDROFORMILACION, CARACTERIZADO PORQUE EL CATALIZADOR DE RODIO SE EXTRAE DE LA FASE ACUOSA DEL PRODUCTO DE FORMILACION MEDIANTE UNA SOLUCION ACUOSA DE UN AGENTE COMPLEJANTE QUE CONTIENE NITROGENO DEL GRUPO DE LAS PIRIDINAS SULFONADAS, DE LAS QUINOLINAS SULFONADAS, DE LAS 2,2''-BIPIRIDINAS, 1,10-FENANTROLINAS, 2,2''-BIQUINOLINAS, 2,2'',6'',2" Y PORFINAS QUE LLEVAN SUSTITUYENTES SULFONADOS O ESTAN OPCIONALMENTE SULFONADAS, Y/O DEL GRUPO DE LAS PIRIDINAS CARBOXILADAS, QUINOLINAS CARBOXILADAS, O DE LAS 2,2''-BIPIRIDINAS, 1,10-FENANTROLINAS, 2,2''-BIQUINOLINAS, 2,2'',6'',2"-TERPIRIDINAS Y PORFINAS QUE LLEVAN SUSTITUYENTES CARBOXILADOS O ESTAN OPCIONALMENTE CARBOXILADAS,Y EL ALCOHOL Y/O ALDEHIDO SE AISLA DEL PRODUCTO EXTRAIDO DE HIDROFORMILACION, EL EXTRACTO ACUOSO QUE CONTIENE EL RODIO SE LLEVA A UNA ETAPA DE PRECARBONILACION, Y SE SOMETE A UNA PRECARBONILACION EN TAL ETAPA EN PRESENCIA DE UN LIQUIDO ORGANICO INSOLUBLE EN AGUA Y EN PRESENCIA DE MONOXIDO DE CARBONO, GAS DE SINTESIS O UNA MEZCLA DE GASES QUE CONTIENE MONOXIDO DE CARBONO A UNA PRESION DE 50 A 1000 BARES Y A UNA TEMPERATURA DE 50 A 180º C, EL PRODUCTO DE LA ETAPA DE PRECARBONILACION SE SEPARA EN UNA PARTE ORGANICA QUE CONTIENE LA MAYORIA DEL RODIO Y UNA FASE ACUOSA QUE CONTIENE EL AGENTE COMPLEJANTE Y LA FASE ORGANICA PARA LA HIDROFORMILACION DE LA OLEFINA SE AÑADE A LA ETAPA DE HIDROFORMILACION A UNA PRESION DE 50 A 1000 BARES Y A UNA TEMPERATURA DE 50 A 180º C.
ES95912212T 1994-03-16 1995-03-06 Procedimiento para la obtencion de alcoholes y/o aldehidos. Expired - Lifetime ES2121357T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE4408950A DE4408950A1 (de) 1994-03-16 1994-03-16 Verfahren zur Herstellung von Alkoholen und/oder Aldehyden

Publications (1)

Publication Number Publication Date
ES2121357T3 true ES2121357T3 (es) 1998-11-16

Family

ID=6512962

Family Applications (1)

Application Number Title Priority Date Filing Date
ES95912212T Expired - Lifetime ES2121357T3 (es) 1994-03-16 1995-03-06 Procedimiento para la obtencion de alcoholes y/o aldehidos.

Country Status (7)

Country Link
US (1) US5919987A (es)
EP (1) EP0750602B1 (es)
JP (1) JPH09510219A (es)
AU (1) AU1948795A (es)
DE (2) DE4408950A1 (es)
ES (1) ES2121357T3 (es)
WO (1) WO1995025080A1 (es)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19603201A1 (de) * 1996-01-30 1997-07-31 Basf Ag Verfahren zur Herstellung von Aldehyden durch Hydroformylierung von Olefinen
DE19605435A1 (de) 1996-02-14 1997-08-21 Basf Ag Verfahren zur Herstellung von Aldehyden durch Hydroformylierung mit einem Rhodiumkatalysator und Wiedergewinnung des Rhodiumkatalysators durch Extraktion
CZ283697A3 (cs) * 1996-09-11 1998-04-15 Mitsubishi Chemical Corporation Způsob přípravy roztoku komplexu rhodia a jeho použití
DE19801437A1 (de) 1998-01-16 1999-07-22 Basf Ag Verfahren zur Herstellung von Aldehyden
DE10045056A1 (de) * 2000-09-12 2002-03-21 Basf Ag Verfahren zur kontinuierlichen Hydroformylierung von Polyalkenen mit 30 bis 700 Kohlenstoffatomen
JP4709414B2 (ja) * 2001-04-16 2011-06-22 株式会社Ａｄｅｋａ 乳化重合用乳化剤又は懸濁重合用分散剤
FR2838431B1 (fr) * 2002-04-11 2005-05-06 Inst Francais Du Petrole Procede d'hydroformylation mettant en oeuvre un catalyseur a base de cobalt dans un liquide ionique non-aqueux avec un recyclage du catalyseur ameliore
US8083102B2 (en) * 2006-04-28 2011-12-27 Pouch Pac Innovations, Llc Flexible pouch with a tube spout fitment and flexible sleeve
BRPI0710853A2 (pt) * 2006-05-15 2011-05-17 Dow Global Technologies Inc processo de hidroformilação não aquoso
EP3191569B1 (en) 2014-09-08 2023-01-25 The Procter & Gamble Company Detergent compositions containing a branched surfactant
EP3191570B1 (en) 2014-09-08 2019-05-15 The Procter and Gamble Company Detergent compositions containing a branched surfactant
US12221404B2 (en) 2020-06-05 2025-02-11 SCION Holdings LLC Composition comprising branched aldehydes
WO2021247516A1 (en) 2020-06-05 2021-12-09 SCION Holdings LLC Branched alcohols
WO2021247177A1 (en) 2020-06-05 2021-12-09 SCION Holdings LLC Alcohols production
US12145904B2 (en) 2020-12-17 2024-11-19 SCION Holdings LLC Branched products

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL98500C (es) * 1956-01-11
US4148830A (en) * 1975-03-07 1979-04-10 Union Carbide Corporation Hydroformylation of olefins
US3984478A (en) * 1975-05-27 1976-10-05 Universal Oil Products Company Hydroformylation process
DE2604545C3 (de) * 1976-02-06 1978-08-17 Basf Ag, 6700 Ludwigshafen Verfahren zur Herstellung von Alkylcarbonsäuren
US4329521A (en) * 1980-04-09 1982-05-11 Uop Inc. Oxo alcohol synthesis with rhodium catalyst recycle
US4400547A (en) * 1981-04-10 1983-08-23 Eastman Kodak Company Hydroformylation process utilizing an unmodified rhodium catalyst and the stabilization and regeneration thereof
US4388476A (en) * 1981-05-01 1983-06-14 Eastman Kodak Company Hydroformylation process with rhodium catalyst and oxygen stabilization thereof
US4528403A (en) * 1982-10-21 1985-07-09 Mitsubishi Chemical Industries Ltd. Hydroformylation process for preparation of aldehydes and alcohols
DE3534314A1 (de) * 1985-09-26 1987-04-02 Ruhrchemie Ag Verfahren zur herstellung von aldehyden
FI85849C (fi) * 1988-03-22 1992-06-10 Neste Oy Foerfarande foer framstaellning av alkoholer och aldehyder fraon alkener och syntesgas.
US5183943A (en) * 1991-03-18 1993-02-02 Union Carbide Chemicals & Plastics Technology Corporation Reactivation of hydroformylation catalysts
DE4316180A1 (de) * 1992-09-16 1994-11-17 Basf Ag Verfahren zur Herstellung von Aldehyden

Also Published As

Publication number Publication date
JPH09510219A (ja) 1997-10-14
AU1948795A (en) 1995-10-03
EP0750602B1 (de) 1998-08-19
US5919987A (en) 1999-07-06
DE59503268D1 (de) 1998-09-24
WO1995025080A1 (de) 1995-09-21
EP0750602A1 (de) 1997-01-02
DE4408950A1 (de) 1995-09-21

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