CA2978972A1 - Recovery and/or reuse of palladium catalyst after a suzuki coupling - Google Patents

Recovery and/or reuse of palladium catalyst after a suzuki coupling

Info

Publication number
CA2978972A1
CA2978972A1 CA2978972A CA2978972A CA2978972A1 CA 2978972 A1 CA2978972 A1 CA 2978972A1 CA 2978972 A CA2978972 A CA 2978972A CA 2978972 A CA2978972 A CA 2978972A CA 2978972 A1 CA2978972 A1 CA 2978972A1
Authority
CA
Canada
Prior art keywords
suzuki coupling
palladium
palladium catalyst
coupling reaction
alkyl
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.)
Abandoned
Application number
CA2978972A
Other languages
English (en)
French (fr)
Inventor
Sanjib Biswas
Reetam Chakrabarti
Lauren M. HUFFMAN
Ronald B. Leng
Abraham D. Schuitman
Karin Spiers
Alan L. STOTTLEMYER
Jeffrey B. Epp
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 CA2978972A1 publication Critical patent/CA2978972A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • 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)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2978972A 2015-05-22 2016-05-20 Recovery and/or reuse of palladium catalyst after a suzuki coupling Abandoned CA2978972A1 (en)

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
CA2978972A1 true CA2978972A1 (en) 2016-12-01

Family

ID=57325189

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2978972A Abandoned CA2978972A1 (en) 2015-05-22 2016-05-20 Recovery and/or reuse of palladium catalyst after a suzuki coupling

Country Status (13)

Country Link
US (1) US20160340311A1 (enExample)
EP (1) EP3297436A4 (enExample)
JP (1) JP2018516843A (enExample)
KR (1) KR20180011050A (enExample)
CN (1) CN107426998A (enExample)
AR (1) AR104734A1 (enExample)
BR (1) BR112017019207A2 (enExample)
CA (1) CA2978972A1 (enExample)
CO (1) CO2017008865A2 (enExample)
IL (1) IL254346A (enExample)
MX (1) MX2017011447A (enExample)
TW (1) TW201718503A (enExample)
WO (1) WO2016191245A1 (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT3762368T (pt) 2018-03-08 2022-05-06 Incyte Corp Compostos de aminopirazina diol como inibidores de pi3k-y
WO2020010003A1 (en) 2018-07-02 2020-01-09 Incyte Corporation AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS
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
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
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

Family Cites Families (9)

* 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
AR037228A1 (es) * 2001-07-30 2004-11-03 Dow Agrosciences Llc Compuestos del acido 6-(aril o heteroaril)-4-aminopicolinico, composicion herbicida que los comprende y metodo para controlar vegetacion no deseada
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
PL2797890T3 (pl) * 2011-12-30 2017-06-30 Dow Agrosciences Llc Sposoby wytwarzania 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- metoksyfenylo)pirydyno-2-karboksylanu metylu
JP6290788B2 (ja) * 2011-12-30 2018-03-07 ダウ アグロサイエンシィズ エルエルシー ４−クロロ−２−フルオロ−３−置換−フェニルボロン酸ピナコールエステルの形成方法およびその使用方法
US8703953B2 (en) * 2012-03-09 2014-04-22 Bristol-Myers Squibb Company Aryl ether-base kinase inhibitors

Also Published As

Publication number Publication date
JP2018516843A (ja) 2018-06-28
TW201718503A (zh) 2017-06-01
US20160340311A1 (en) 2016-11-24
BR112017019207A2 (pt) 2018-04-24
KR20180011050A (ko) 2018-01-31
MX2017011447A (es) 2018-06-18
CN107426998A (zh) 2017-12-01
IL254346A (en) 2018-04-30
AR104734A1 (es) 2017-08-09
CO2017008865A2 (es) 2017-11-21
EP3297436A1 (en) 2018-03-28
EP3297436A4 (en) 2018-12-26
WO2016191245A1 (en) 2016-12-01

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Legal Events

Date Code Title Description
FZDE Discontinued

Effective date: 20200831