CN107426998A - 铃木偶联后钯催化剂的回收和/或再利用 - Google Patents

铃木偶联后钯催化剂的回收和/或再利用 Download PDF

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Publication number
CN107426998A
CN107426998A CN201680014261.6A CN201680014261A CN107426998A CN 107426998 A CN107426998 A CN 107426998A CN 201680014261 A CN201680014261 A CN 201680014261A CN 107426998 A CN107426998 A CN 107426998A
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CN
China
Prior art keywords
alkyl
palladium
suzuki coupling
palladium catalyst
coupling reaction
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.)
Pending
Application number
CN201680014261.6A
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English (en)
Chinese (zh)
Inventor
S·比斯瓦斯
R·查克拉巴蒂
L·M·哈夫曼
R·B·兰
A·D·休特曼
K·施皮尔斯
A·L·斯托特尔迈尔
J·B·埃普
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.)
Corteva Agriscience LLC
Original Assignee
Dow AgroSciences LLC
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 Dow AgroSciences LLC filed Critical Dow AgroSciences LLC
Publication of CN107426998A publication Critical patent/CN107426998A/zh
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/803—Processes of preparation
    • 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
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • B01J2231/4227—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 with Y= Cl
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • 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
    • 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
    • Y02P20/582—Recycling of unreacted starting or intermediate materials
    • 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)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
CN201680014261.6A 2015-05-22 2016-05-20 铃木偶联后钯催化剂的回收和/或再利用 Pending CN107426998A (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562165502P 2015-05-22 2015-05-22
US62/165,502 2015-05-22
PCT/US2016/033429 WO2016191245A1 (en) 2015-05-22 2016-05-20 Recovery and/or reuse of palladium catalyst after a suzuki coupling

Publications (1)

Publication Number Publication Date
CN107426998A true CN107426998A (zh) 2017-12-01

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CN201680014261.6A Pending CN107426998A (zh) 2015-05-22 2016-05-20 铃木偶联后钯催化剂的回收和/或再利用

Country Status (13)

Country Link
US (1) US20160340311A1 (cg-RX-API-DMAC7.html)
EP (1) EP3297436A4 (cg-RX-API-DMAC7.html)
JP (1) JP2018516843A (cg-RX-API-DMAC7.html)
KR (1) KR20180011050A (cg-RX-API-DMAC7.html)
CN (1) CN107426998A (cg-RX-API-DMAC7.html)
AR (1) AR104734A1 (cg-RX-API-DMAC7.html)
BR (1) BR112017019207A2 (cg-RX-API-DMAC7.html)
CA (1) CA2978972A1 (cg-RX-API-DMAC7.html)
CO (1) CO2017008865A2 (cg-RX-API-DMAC7.html)
IL (1) IL254346A (cg-RX-API-DMAC7.html)
MX (1) MX2017011447A (cg-RX-API-DMAC7.html)
TW (1) TW201718503A (cg-RX-API-DMAC7.html)
WO (1) WO2016191245A1 (cg-RX-API-DMAC7.html)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110041373A (zh) * 2019-04-29 2019-07-23 江苏万年长药业有限公司 一种雷迪帕韦中间体制备过程中贵金属催化剂的回收方法
CN114921657A (zh) * 2022-05-06 2022-08-19 浙江微通催化新材料有限公司 一种从含铯盐的废钯催化剂中回收铯和钯的方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CR20200464A (es) 2018-03-08 2021-04-14 Incyte Corp Compuestos diólicos de aminopirazina como inhibidores de pi3k-y
WO2020010003A1 (en) 2018-07-02 2020-01-09 Incyte Corporation AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS
JP2021070684A (ja) * 2019-10-30 2021-05-06 東ソー株式会社 ハロゲン化合物の製造方法
KR102419596B1 (ko) 2020-10-06 2022-07-08 김창기 팔라듐이 포함된 슬러지 회수 장치

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1551876A (zh) * 2001-07-30 2004-12-01 �ݶ�ũ�����޹�˾ 6-芳基-4-氨基吡啶甲酸酯及其作为除草剂的用途

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3641076A (en) * 1970-08-24 1972-02-08 Union Oil Co Catalyst recovery
US4791226A (en) * 1983-06-23 1988-12-13 Amoco Corporation Catalyst and process for purification of crude terephthalic acid
US20060258875A1 (en) * 2005-05-10 2006-11-16 Clementine Reyes Methods for manufacturing supported nanocatalysts and methods for using supported nanocatalysts
FR2914867B1 (fr) * 2007-04-16 2009-06-05 Univ Haute Alsace Etablissemen Procede de synthese de catalyseurs heterogenes au palladium, catalyseurs obtenus et utilisations de ces derniers.
WO2011020900A2 (en) * 2009-08-21 2011-02-24 Technische Universität Berlin A process for preparing biaryl compounds in a suzuki type reaction allowing product isolation and catalyst recycling in one step
NZ627192A (en) * 2011-12-30 2015-09-25 Dow Agrosciences Llc Methods of producing methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate
BR112014016048B8 (pt) * 2011-12-30 2022-10-11 Dow Agrosciences Llc Métodos para formação e uso de ésteres de pinacol do ácido 4-cloro-2-flúor-3-substituído-fenilborônico e de 2-(4-cloro-2-flúor-3-metoxifenil)-4,4,5,5-tetrametil1,3,2-dioxaborolano, e éster de pinacol do ácido 4cloro-2-flúor-3-substituído-fenilborônico
US8703953B2 (en) * 2012-03-09 2014-04-22 Bristol-Myers Squibb Company Aryl ether-base kinase inhibitors

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1551876A (zh) * 2001-07-30 2004-12-01 �ݶ�ũ�����޹�˾ 6-芳基-4-氨基吡啶甲酸酯及其作为除草剂的用途

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHANDAN SARMAH, ET AL: "Anchoring palladium acetate onto imine-functionalized silica gel through coordinative attachment: An effective recyclable catalyst for the Suzuki–Miyaura reaction in aqueous-isopropanol", 《CATALYSIS TODAY》 *
SABRINA M. NOBRE, ET AL: "Simple and efficient protocol for catalyst recycling and product recovery in the Pd-catalyzed homogeneous Suzuki reaction", 《TETRAHEDRON LETTERS》 *
SIEGFRIED SCHNEIDER, ET AL: "Application of the Fluorous Biphase Concept to Palladium-Catalyzed Suzuki Couplings", 《HELVETICA CHIMICA ACTA》 *
SULUR G. MANJUNATHA, ET AL: "A simple way of recycling of homogeneous catalyst in Suzuki reaction", 《 GREEN CHEMISTRY LETTERS AND REVIEWS》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110041373A (zh) * 2019-04-29 2019-07-23 江苏万年长药业有限公司 一种雷迪帕韦中间体制备过程中贵金属催化剂的回收方法
CN114921657A (zh) * 2022-05-06 2022-08-19 浙江微通催化新材料有限公司 一种从含铯盐的废钯催化剂中回收铯和钯的方法

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CO2017008865A2 (es) 2017-11-21
BR112017019207A2 (pt) 2018-04-24
EP3297436A1 (en) 2018-03-28
CA2978972A1 (en) 2016-12-01
WO2016191245A1 (en) 2016-12-01
US20160340311A1 (en) 2016-11-24
IL254346A (en) 2018-04-30
EP3297436A4 (en) 2018-12-26
MX2017011447A (es) 2018-06-18
AR104734A1 (es) 2017-08-09
JP2018516843A (ja) 2018-06-28
TW201718503A (zh) 2017-06-01
KR20180011050A (ko) 2018-01-31

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Application publication date: 20171201