AR070171A1 - Compuestos de organofosfina sulfonada y su uso en procesos de hidroformilacion - Google Patents
Compuestos de organofosfina sulfonada y su uso en procesos de hidroformilacionInfo
- Publication number
- AR070171A1 AR070171A1 ARP090100114A ARP090100114A AR070171A1 AR 070171 A1 AR070171 A1 AR 070171A1 AR P090100114 A ARP090100114 A AR P090100114A AR P090100114 A ARP090100114 A AR P090100114A AR 070171 A1 AR070171 A1 AR 070171A1
- Authority
- AR
- Argentina
- Prior art keywords
- ligand
- alkyl ether
- alkyl
- sulfonated
- phosphorus atom
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 5
- 239000003446 ligand Substances 0.000 abstract 8
- 150000005215 alkyl ethers Chemical class 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000004437 phosphorous atom Chemical group 0.000 abstract 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract 4
- 125000002723 alicyclic group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001768 cations Chemical class 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- -1 alkyl radicals Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 238000007037 hydroformylation reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- 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
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- 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
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
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- 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
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- 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
- B01J31/4053—Regeneration or reactivation of catalysts containing metals with recovery of phosphorous catalyst system constituents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5004—Acyclic saturated phosphines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5018—Cycloaliphatic phosphines
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- 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
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- 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
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- 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
- B01J2531/821—Ruthenium
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- 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
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- 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
- B01J2531/827—Iridium
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- 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
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
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- 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
- B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
- B01J2531/96—Water
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- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/30—Non-coordinating groups comprising sulfur
- B01J2540/32—Sulfonic acid groups or their salts
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- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/60—Groups characterized by their function
- B01J2540/64—Solubility enhancing groups
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- 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)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
La presente se refiere a un compuesto que comprende una clase de compuestos de triorganofosfina sulfonada de la formula R1R2P-R3 [-O-(CH2)n-(SO3M)]m, en donde R1 y R2 se seleccionan individualmente de radicales alquilo, aralquilo y alicíclicos, en donde R3 representa un radical alquileno o alicíclico bivalente o polivalente, que está enlazado al átomo de fosforo y a uno o más sustituyentes sulfonato a través de un ligando alquiléter, y además en donde R3 no contiene ninguna porcion arilo; n es un numero entero que refleja un numero de grupos metileno en el ligando alquiléter; M representa un cation monovalente, y m es un numero entero que representa un numero total de sustituyentes alquiléter sulfonados. Catalizadores complejos de metal de transicion-ligando, que son capaces de catalizar la hidroformilacion de un compuesto olefínicamente insaturado, con monoxido de carbono e hidrogeno, para formar uno o más correspondientes productos aldehído. El ligando es incapaz de realizar intercambio alquilo-arilo, lo cual produce un uso reducido del ligando y una mejor recuperacion y reciclamiento del ligando y del rodio. Reivindicacion 1: Una composicion que comprende una clase de compuestos de triorganofosfina sulfonada, representados por la formula (1), en donde R1 y R2 cada uno individualmente representa un radical hidrocarbilo monovalente o hidrocarbilo sustituido, que se selecciona del grupo que consiste de radicales alquilo, aralquilo y alicíclicos; en donde R3 representa un radical alquileno o alicíclico, bivalente o polivalente, que está enlazado al átomo de fosforo y a uno o más sustituyentes sulfonato a través de un ligando alquiléter; y además en donde R3 no contiene ninguna porcion arilo; n es un numero entero que representa un numero de grupos metileno en el ligando alquiléter, que varía dentro del rango de 1 a aproximadamente 5; M representa un cation monovalente; y m es un numero entero que representa un numero total de sustituyentes alquiléter sulfonados enlazados a R3; y en donde en cada uno de R1, R2 y R3, el átomo, de carbono unido al átomo de fosforo o un átomo de carbono directamente unido al átomo de carbono unido al átomo de fosforo, adicionalmente está unido a cuando menos otros 2 átomos de carbono.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2106808P | 2008-01-15 | 2008-01-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR070171A1 true AR070171A1 (es) | 2010-03-17 |
Family
ID=40521905
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP090100114A AR070171A1 (es) | 2008-01-15 | 2009-01-14 | Compuestos de organofosfina sulfonada y su uso en procesos de hidroformilacion |
Country Status (5)
Country | Link |
---|---|
US (1) | US8461366B2 (es) |
EP (1) | EP2231683B1 (es) |
AR (1) | AR070171A1 (es) |
BR (1) | BRPI0905685A2 (es) |
WO (1) | WO2009091670A1 (es) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150017718A (ko) | 2012-05-31 | 2015-02-17 | 미쓰비시 가가꾸 가부시키가이샤 | 코폴리머, 유기 반도체 재료, 유기 전자 디바이스 및 태양 전지 모듈 |
EP2858099A4 (en) | 2012-06-01 | 2015-05-20 | Mitsubishi Chem Corp | PROCESS FOR PRODUCING SEMICONDUCTOR LAYER CONTAINING METAL OXIDE AND ELECTRONIC DEVICE |
CN104248860A (zh) | 2013-06-27 | 2014-12-31 | 陶氏技术投资有限责任公司 | 热管理方法 |
CN111533837B (zh) * | 2020-04-20 | 2022-02-11 | 浙江师范大学 | 一种酸性聚合离子液体及其制备方法与应用 |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
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US2900393A (en) | 1956-12-11 | 1959-08-18 | Rohm & Haas | Preparation of 3-methyl 1,3-propane sultone |
US3527809A (en) | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
US4148830A (en) | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
US4247486A (en) | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
US4283304A (en) | 1979-05-21 | 1981-08-11 | Union Carbide Corporation | Process for removing triorganophosphine from a liquid composition |
DE3235030A1 (de) | 1982-09-22 | 1984-03-22 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von sulfonierten arylphosphinen |
US4625068A (en) | 1985-03-20 | 1986-11-25 | Exxon Chemical Patents Inc. | Rhodium catalyzed hydroformylation of internal olefins |
US4642388A (en) | 1985-08-30 | 1987-02-10 | Exxon Chemical Patents Inc. | Rhodium catalyzed hydroformylation of alpha-substituted alpha-olefins |
US4716138A (en) | 1986-07-21 | 1987-12-29 | Union Carbide Corporation | Oligomerization to alpha-olefins |
US4689437A (en) | 1986-07-21 | 1987-08-25 | Union Carbide Corporation | Oligomerization to alpha-olefins |
US4822915A (en) | 1986-07-21 | 1989-04-18 | Union Carbide Corporation | Phosphine and sulfonate bearing ligands |
US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
US5180854A (en) | 1988-07-14 | 1993-01-19 | Union Carbide Chemicals & Plastics Technology Corporation | Process for catalyst aldehyde product separation |
KR950000633B1 (ko) * | 1988-07-14 | 1995-01-26 | 유니온 카바이드 케미칼즈 앤드 플라스틱스 캄파니 인코포레이티드 | 알콜 및 알데하이드의 제조방법 |
US5300617A (en) | 1993-01-21 | 1994-04-05 | Exxon Chemical Patents Inc. | Potassium para-diphenyl phosphino benzene sulfonate ligand |
TW248563B (es) | 1993-06-29 | 1995-06-01 | Hoechst Ag | |
DE4325816A1 (de) | 1993-07-31 | 1995-02-02 | Hoechst Ag | Sekundäre und tertiäre Phosphane und Verfahren zu ihrer Herstellung |
DE4427836A1 (de) | 1994-08-05 | 1996-02-08 | Hoechst Ag | Verbindungen aus der Reihe der Phosphane, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
US5756855A (en) | 1994-08-19 | 1998-05-26 | Union Carbide Chemicals & Plastics Technology Corporation | Stabilization of phosphite ligands in hydroformylation process |
DE4435189A1 (de) | 1994-09-30 | 1996-04-04 | Hoechst Ag | Neue sulfonierte Phosphine, Verfahren zu ihrer Herstellung und ihre Verwendung als Bestandteil von Katalysatorsystemen |
EP0805139B1 (en) | 1995-09-26 | 2000-04-26 | Kuraray Co., Ltd. | Hydroformylation method |
US5760286A (en) | 1997-04-02 | 1998-06-02 | Uop Llc | Preparation of tertiary phosphine sulfonic acids |
DE19740672A1 (de) | 1997-09-16 | 1999-03-18 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung |
DE19756945C2 (de) | 1997-12-22 | 2000-08-03 | Celanese Chem Europe Gmbh | Nichtwäßrige ionogene Ligandflüssigkeiten, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatorbestandteil |
US5932772A (en) | 1998-02-02 | 1999-08-03 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
US5952530A (en) | 1998-02-02 | 1999-09-14 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
FR2787786B1 (fr) | 1998-12-23 | 2001-02-02 | Rhone Poulenc Fibres | Procede de preparation de composes organophosphores sulfones hydrosolubles et la realisation de reactions organiques avec catalyse biphasique |
DE19918284C1 (de) | 1999-04-22 | 2000-12-14 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von sulfonierten Arylphosphinen |
WO2003042224A2 (en) * | 2001-11-15 | 2003-05-22 | Sasol Technology (Pty) Ltd | Preparation of derivatives of a group 5a element |
CA2424225C (en) | 2003-03-31 | 2008-08-05 | Cytec Canada Inc. | Tertiary phosphines and their methods of preparation |
US7615658B2 (en) | 2003-04-25 | 2009-11-10 | Dow Global Technologies, Inc. | Aldehyde and alcohol compositions derived from seed oils |
WO2007035540A2 (en) | 2005-09-15 | 2007-03-29 | Dow Global Technologies Inc. | Process for the monosulfonation of aromatic phosphines, and zwitterionic product derived therefrom |
CA2652016C (en) * | 2006-05-15 | 2015-02-03 | Dow Global Technologies Inc. | Hydroformylation process and product separation with improved recovery of rhodium |
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2009
- 2009-01-09 BR BRPI0905685-8A patent/BRPI0905685A2/pt not_active Application Discontinuation
- 2009-01-09 EP EP09703010.0A patent/EP2231683B1/en active Active
- 2009-01-09 US US12/812,981 patent/US8461366B2/en active Active
- 2009-01-09 WO PCT/US2009/030556 patent/WO2009091670A1/en active Application Filing
- 2009-01-14 AR ARP090100114A patent/AR070171A1/es not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
EP2231683A1 (en) | 2010-09-29 |
US8461366B2 (en) | 2013-06-11 |
BRPI0905685A2 (pt) | 2015-07-07 |
EP2231683B1 (en) | 2016-03-23 |
WO2009091670A1 (en) | 2009-07-23 |
US20110054204A1 (en) | 2011-03-03 |
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