NL1015520C2 - Werkwijze voor het regeneren van Pd-Katalysatoren. - Google Patents

Werkwijze voor het regeneren van Pd-Katalysatoren. Download PDF

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Publication number
NL1015520C2
NL1015520C2 NL1015520A NL1015520A NL1015520C2 NL 1015520 C2 NL1015520 C2 NL 1015520C2 NL 1015520 A NL1015520 A NL 1015520A NL 1015520 A NL1015520 A NL 1015520A NL 1015520 C2 NL1015520 C2 NL 1015520C2
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NL
Netherlands
Prior art keywords
reaction
catalyst
coupling reaction
bromine
sub
Prior art date
Application number
NL1015520A
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English (en)
Dutch (nl)
Inventor
Andreas Hendrikus Maria Vries
Johannes Gerardus De Vries
Floris Jacobus Parlevliet
Original Assignee
Dsm Nv
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 Dsm Nv filed Critical Dsm Nv
Priority to NL1015520A priority Critical patent/NL1015520C2/nl
Priority to EP01943971A priority patent/EP1294483B1/fr
Priority to ES01943971T priority patent/ES2249447T3/es
Priority to US10/297,237 priority patent/US6921731B2/en
Priority to AU2001266429A priority patent/AU2001266429A1/en
Priority to AT01943971T priority patent/ATE303865T1/de
Priority to DE60113257T priority patent/DE60113257T2/de
Priority to PCT/NL2001/000460 priority patent/WO2002000340A1/fr
Priority to JP2002505113A priority patent/JP2004501744A/ja
Application granted granted Critical
Publication of NL1015520C2 publication Critical patent/NL1015520C2/nl

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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
    • B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
    • 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
    • B01J23/90—Regeneration or reactivation
    • B01J23/96—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the noble metals
    • 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
    • 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
    • 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
    • B01J38/00—Regeneration or reactivation of catalysts, in general
    • B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
    • B01J38/50—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids
    • B01J38/54—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids halogen-containing
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B01J21/04—Alumina
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/08—Silica
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18—Carbon
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4261—Heck-type, i.e. RY + C=C, in which R is aryl
    • 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
    • B01J23/44—Palladium
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213—Complexes without C-metal linkages
    • B01J2531/0222—Metal clusters, i.e. complexes comprising 3 to about 1000 metal atoms with metal-metal bonds to provide one or more all-metal (M)n rings, e.g. Rh4(CO)12
    • 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
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
    • B01J27/13—Platinum group metals
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2239—Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
NL1015520A 2000-06-26 2000-06-26 Werkwijze voor het regeneren van Pd-Katalysatoren. NL1015520C2 (nl)

Priority Applications (9)

Application Number Priority Date Filing Date Title
NL1015520A NL1015520C2 (nl) 2000-06-26 2000-06-26 Werkwijze voor het regeneren van Pd-Katalysatoren.
EP01943971A EP1294483B1 (fr) 2000-06-26 2001-06-19 Procede de regeneration de catalyseurs pd
ES01943971T ES2249447T3 (es) 2000-06-26 2001-06-19 Procedimiento para regenerar catalizadores de pd.
US10/297,237 US6921731B2 (en) 2000-06-26 2001-06-19 Process for regenerating Pd catalysts
AU2001266429A AU2001266429A1 (en) 2000-06-26 2001-06-19 Process for regenerating pd catalysts
AT01943971T ATE303865T1 (de) 2000-06-26 2001-06-19 Verfahren zur regenerierung von pd-katalysatoren
DE60113257T DE60113257T2 (de) 2000-06-26 2001-06-19 Verfahren zur regenerierung von pd-katalysatoren
PCT/NL2001/000460 WO2002000340A1 (fr) 2000-06-26 2001-06-19 Procede de regeneration de catalyseurs pd
JP2002505113A JP2004501744A (ja) 2000-06-26 2001-06-19 Ｐｄ触媒の再生のための方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1015520A NL1015520C2 (nl) 2000-06-26 2000-06-26 Werkwijze voor het regeneren van Pd-Katalysatoren.
NL1015520 2000-06-26

Publications (1)

Publication Number Publication Date
NL1015520C2 true NL1015520C2 (nl) 2001-12-28

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Family Applications (1)

Application Number Title Priority Date Filing Date
NL1015520A NL1015520C2 (nl) 2000-06-26 2000-06-26 Werkwijze voor het regeneren van Pd-Katalysatoren.

Country Status (9)

Country Link
US (1) US6921731B2 (fr)
EP (1) EP1294483B1 (fr)
JP (1) JP2004501744A (fr)
AT (1) ATE303865T1 (fr)
AU (1) AU2001266429A1 (fr)
DE (1) DE60113257T2 (fr)
ES (1) ES2249447T3 (fr)
NL (1) NL1015520C2 (fr)
WO (1) WO2002000340A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1329117C (zh) * 2003-06-12 2007-08-01 中国石油化工股份有限公司 用于选择性加氢的钯/碳催化剂的制备方法
DE102004049508A1 (de) * 2004-10-11 2006-04-13 Ludwig-Maximilians-Universität München Eisen- oder Kobalt-katalysierte Kohlenstoff-Kohlenstoff-Kupplungsreaktion von Arylen, Alkenen und Alkinen mit Kupferreagenzien
CN100355718C (zh) * 2005-09-21 2007-12-19 扬子石油化工股份有限公司 加氢精制对苯二甲酸的催化剂的再生方法
DE602006013688D1 (de) * 2005-11-16 2010-05-27 Hoffmann La Roche Neues verfahren zur herstellung von thoc
CN103028422B (zh) * 2011-09-29 2015-04-08 中国石油化工股份有限公司 粗对苯二甲酸加氢精制钯炭催化剂的再生方法
CN102942429A (zh) * 2012-11-26 2013-02-27 大连理工大学 一种钯碳催化的制备氮杂或硫杂芳基联芳化合物的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0514821A1 (fr) * 1991-05-22 1992-11-25 Bromine Compounds Ltd. Méthode de production de composés biaryle
WO1998049128A1 (fr) * 1997-04-25 1998-11-05 Dsm N.V. Procede de preparation d'une olefine (hetero)aromatique
US6005151A (en) * 1995-02-01 1999-12-21 Aventis Processs for preparing aromatic olefins using palladacycle catalysis
US6071843A (en) * 1996-05-10 2000-06-06 Bayer Aktiengesellschaft Process for reactivating catalyst systems containing a platinum group metal

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1084159A (fr) * 1965-07-09
US3700729A (en) * 1965-12-06 1972-10-24 Union Oil Co Preparation of aromatic acids
DE19512618A1 (de) * 1995-04-05 1996-10-10 Bayer Ag Platinmetall enthaltende Träger-Katalysatoren und Verfahren zur Herstellung von Diarylcarbonaten

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0514821A1 (fr) * 1991-05-22 1992-11-25 Bromine Compounds Ltd. Méthode de production de composés biaryle
US6005151A (en) * 1995-02-01 1999-12-21 Aventis Processs for preparing aromatic olefins using palladacycle catalysis
US6071843A (en) * 1996-05-10 2000-06-06 Bayer Aktiengesellschaft Process for reactivating catalyst systems containing a platinum group metal
WO1998049128A1 (fr) * 1997-04-25 1998-11-05 Dsm N.V. Procede de preparation d'une olefine (hetero)aromatique

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CORTÉS ET AL.: "Palladium(0) Complexes of a 15-Membered Macrocyclic Triolefin as a Recoverable Catalyst", EUR. J. ORG. CHEM., January 2000 (2000-01-01), pages 239 - 243, XP002161460 *
HERRMANN W A ET AL: "PALLADACYCLES AS STRUCTURALLY DEFINED CATALYSTS FOR THE HECK OLEFINATION OF CHLORO- AND BROMOARENES", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION,DE,VERLAG CHEMIE. WEINHEIM, vol. 34, no. 17, 15 September 1995 (1995-09-15), pages 1844 - 1848, XP002056984, ISSN: 0570-0833 *

Also Published As

Publication number Publication date
ES2249447T3 (es) 2006-04-01
ATE303865T1 (de) 2005-09-15
EP1294483A1 (fr) 2003-03-26
DE60113257D1 (de) 2005-10-13
DE60113257T2 (de) 2006-06-22
JP2004501744A (ja) 2004-01-22
US20040029714A1 (en) 2004-02-12
AU2001266429A1 (en) 2002-01-08
US6921731B2 (en) 2005-07-26
EP1294483B1 (fr) 2005-09-07
WO2002000340A1 (fr) 2002-01-03

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