TW201718503A - 於鈴木偶合（ｓｕｚｕｋｉ ｃｏｕｐｌｉｎｇ）後回收及／或再利用鈀催化劑之技術 - Google Patents
於鈴木偶合（ｓｕｚｕｋｉ ｃｏｕｐｌｉｎｇ）後回收及／或再利用鈀催化劑之技術 Download PDFInfo
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- TW201718503A TW201718503A TW105115960A TW105115960A TW201718503A TW 201718503 A TW201718503 A TW 201718503A TW 105115960 A TW105115960 A TW 105115960A TW 105115960 A TW105115960 A TW 105115960A TW 201718503 A TW201718503 A TW 201718503A
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- Prior art keywords
- suzuki coupling
- palladium
- palladium catalyst
- coupling reaction
- alkyl
- Prior art date
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 280
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 130
- 238000006069 Suzuki reaction reaction Methods 0.000 title claims abstract description 97
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- 238000011084 recovery Methods 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 82
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 61
- 239000000047 product Substances 0.000 claims description 43
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- 239000000203 mixture Substances 0.000 claims description 35
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- ZAYTUZJMFVYJSU-UHFFFAOYSA-N 4,5-dichloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid Chemical compound COC1=C(Cl)C=CC(C=2C(=C(Cl)C=C(N=2)C(O)=O)Cl)=C1F ZAYTUZJMFVYJSU-UHFFFAOYSA-N 0.000 description 3
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- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- CRHWEIDCXNDTMO-UHFFFAOYSA-N ditert-butylphosphane Chemical compound CC(C)(C)PC(C)(C)C CRHWEIDCXNDTMO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562165502P | 2015-05-22 | 2015-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201718503A true TW201718503A (zh) | 2017-06-01 |
Family
ID=57325189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW105115960A TW201718503A (zh) | 2015-05-22 | 2016-05-23 | 於鈴木偶合（ｓｕｚｕｋｉ ｃｏｕｐｌｉｎｇ）後回收及／或再利用鈀催化劑之技術 |
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) |
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| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
-
2016
- 2016-05-20 US US15/159,973 patent/US20160340311A1/en not_active Abandoned
- 2016-05-20 EP EP16800528.8A patent/EP3297436A4/en not_active Withdrawn
- 2016-05-20 MX MX2017011447A patent/MX2017011447A/es unknown
- 2016-05-20 BR BR112017019207A patent/BR112017019207A2/pt not_active Application Discontinuation
- 2016-05-20 KR KR1020177025293A patent/KR20180011050A/ko not_active Withdrawn
- 2016-05-20 CA CA2978972A patent/CA2978972A1/en not_active Abandoned
- 2016-05-20 CN CN201680014261.6A patent/CN107426998A/zh active Pending
- 2016-05-20 JP JP2017547544A patent/JP2018516843A/ja not_active Withdrawn
- 2016-05-20 WO PCT/US2016/033429 patent/WO2016191245A1/en not_active Ceased
- 2016-05-23 AR ARP160101498A patent/AR104734A1/es unknown
- 2016-05-23 TW TW105115960A patent/TW201718503A/zh unknown
-
2017
- 2017-08-30 CO CONC2017/0008865A patent/CO2017008865A2/es unknown
- 2017-09-06 IL IL254346A patent/IL254346A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2978972A1 (en) | 2016-12-01 |
| JP2018516843A (ja) | 2018-06-28 |
| 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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