WO2012071360A1 - Metal - catalyzed mono - hydrosilylation of polyunsaturated compounds - Google Patents
Metal - catalyzed mono - hydrosilylation of polyunsaturated compounds Download PDFInfo
- Publication number
- WO2012071360A1 WO2012071360A1 PCT/US2011/061752 US2011061752W WO2012071360A1 WO 2012071360 A1 WO2012071360 A1 WO 2012071360A1 US 2011061752 W US2011061752 W US 2011061752W WO 2012071360 A1 WO2012071360 A1 WO 2012071360A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- substituted
- independently
- group
- aryl
- 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.)
- Ceased
Links
Classifications
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- 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
Definitions
- each occurrence of Ri, R 2 , R3, R4, s, 6, R7, R»» R9, R19 and R20 is independently hydrogen, C I -C I 8 alkyl, C I -C I 8 substituted alkyl, aryl, substituted aryl, or an inert functional group, wherein Rj to R ? , R19 and R20, other than hydrogen, optionally contain at least one heteroatom;
- each occurrence of R !7 and R t 8 is independently alkyl, substituted alkyl, aryl, or substituted aryl, wherein each of Rn and R 18 optionally contains at least one heteroatom, and wherein R )7 and R[ 8 taken together may form a ring being a substituted or unsubstituted, saturated or unsaturated cyclic structure;
- each occurrence of R19 and R 2 o is independently a covalent bond that connects Si and C, an alky!, substituted alkyl, or a heteroatom, wherein R1 , and R 2 o optionally contain at least one heteroatom; wherein L t -L 2 bonds with G through unsaturated sites Sj and S 2 ;
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR112013012734A BR112013012734A2 (pt) | 2010-11-24 | 2011-11-22 | mono-hidrossililação catalisada por metal não-precioso seletivo de compostos polinsaturados |
| KR1020137016391A KR101896423B1 (ko) | 2010-11-24 | 2011-11-22 | 폴리불포화 화합물의 금속-촉매 모노-하이드로실릴화 |
| JP2013541003A JP6019034B2 (ja) | 2010-11-24 | 2011-11-22 | 多価不飽和化合物の金属触媒モノヒドロシリル化 |
| EP11794591.5A EP2643330B1 (en) | 2010-11-24 | 2011-11-22 | Metal-catalyzed mono-hydrosilylation of polyunsaturated compounds |
| CN201180065872.0A CN103732599B (zh) | 2010-11-24 | 2011-11-22 | 多不饱和化合物的金属催化的单-氢化硅烷化 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41706110P | 2010-11-24 | 2010-11-24 | |
| US61/417,061 | 2010-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2012071360A1 true WO2012071360A1 (en) | 2012-05-31 |
Family
ID=45319392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2011/061752 Ceased WO2012071360A1 (en) | 2010-11-24 | 2011-11-22 | Metal - catalyzed mono - hydrosilylation of polyunsaturated compounds |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8895770B2 (https=) |
| EP (1) | EP2643330B1 (https=) |
| JP (1) | JP6019034B2 (https=) |
| KR (1) | KR101896423B1 (https=) |
| CN (1) | CN103732599B (https=) |
| BR (1) | BR112013012734A2 (https=) |
| TW (1) | TWI457176B (https=) |
| WO (1) | WO2012071360A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10829504B2 (en) | 2016-01-22 | 2020-11-10 | Shin-Etsu Chemical Co., Ltd. | Isocyanide compound and hydrosilylation reaction catalyst |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103347889A (zh) * | 2010-11-24 | 2013-10-09 | 莫门蒂夫性能材料股份有限公司 | 氢化硅烷化催化剂 |
| JP6101695B2 (ja) | 2011-09-20 | 2017-03-22 | ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ | ニッケル含有ヒドロシリル化触媒及びその触媒を含有する組成物 |
| CN103958059B (zh) | 2011-12-01 | 2017-04-26 | 道康宁公司 | 硅氢加成反应催化剂和可固化组合物及它们的制备和使用方法 |
| US9782763B2 (en) * | 2011-12-14 | 2017-10-10 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
| US9371340B2 (en) | 2012-08-16 | 2016-06-21 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts |
| US9447125B2 (en) | 2012-08-16 | 2016-09-20 | Momentive Performance Materials Inc. | Reusable homogeneous cobalt pyridine diimine catalysts for dehydrogenative silylation and tandem dehydrogenative-silylation-hydrogenation |
| US9371339B2 (en) | 2013-05-06 | 2016-06-21 | Momentive Performance Materials Inc. | Saturated and unsaturated silahydrocarbons via iron and cobalt pyridine diimine catalyzed olefin silylation |
| WO2014182670A2 (en) | 2013-05-06 | 2014-11-13 | Momentive Performance Materials Inc. | Selective 1,2-hydrosilylation of terminally unsaturated 1,3-dienes using iron catalysts |
| WO2014186513A1 (en) | 2013-05-15 | 2014-11-20 | Momentive Performance Materials Inc. | Activation of metal salts with silylhydrides and their use in hydrosilylation reactions |
| EP3071552A1 (en) | 2013-11-19 | 2016-09-28 | The Trustees of Princeton University | Hydroboration and borylation with cobalt catalysts |
| WO2015077304A1 (en) * | 2013-11-19 | 2015-05-28 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| JP6486925B2 (ja) * | 2013-11-19 | 2019-03-20 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | コバルト触媒並びにヒドロシリル化及び脱水素シリル化のためのその使用 |
| JP2017520519A (ja) * | 2014-05-08 | 2017-07-27 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | ジアルキルコバルト触媒並びにヒドロシリル化および脱水素シリル化のためのそれらの使用 |
| JP2015231965A (ja) * | 2014-06-10 | 2015-12-24 | 国立研究開発法人産業技術総合研究所 | 有機ケイ素化合物の製造方法及び触媒組成物 |
| KR102443609B1 (ko) | 2014-08-12 | 2022-09-15 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 하이드로실릴화 반응 촉매 |
| KR20170042648A (ko) | 2014-08-12 | 2017-04-19 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 하이드로실릴화 반응 촉매 |
| JP6761997B2 (ja) | 2014-08-19 | 2020-09-30 | 国立大学法人九州大学 | ヒドロシリル化鉄触媒 |
| KR102564637B1 (ko) | 2015-07-14 | 2023-08-08 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 하이드로실릴화 반응 촉매 |
| WO2017019473A1 (en) * | 2015-07-24 | 2017-02-02 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using pyridinediimine cobalt carboxylate catalysts |
| KR101728308B1 (ko) | 2015-09-14 | 2017-04-19 | 기초과학연구원 | 비전이금속 촉매법 수소규소화 반응을 이용한 규소 고분자 제조방법 |
| CN110366449B (zh) | 2017-02-28 | 2022-10-21 | 国立大学法人九州大学 | 氢化硅烷化反应、氢化反应和氢硅烷还原反应用催化剂 |
| JP2019064950A (ja) | 2017-09-29 | 2019-04-25 | 国立大学法人九州大学 | コバルト錯体、その製造方法およびヒドロシリル化反応用触媒 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5166298A (en) | 1989-01-19 | 1992-11-24 | Essilor International (Compagnie Generale D'optique) | Oxygen-permeable transparent polymer compositions for contact lenses of the rigid type |
| US6265497B1 (en) | 1998-12-04 | 2001-07-24 | Wacker-Chemie Gmbh | Siloxane copolymers containing alkenyl groups |
| US6278011B1 (en) | 1999-08-30 | 2001-08-21 | The University Of Dayton | Polysilahydrocarbons as lubricants for aerospace application |
| WO2008085453A1 (en) * | 2006-12-28 | 2008-07-17 | Momentive Performance Materials Inc. | Silated core polysulfides, their preparation and use in filled elastomer compositions |
| US7429672B2 (en) | 2006-06-09 | 2008-09-30 | Momentive Performance Materials Inc. | Process for the direct synthesis of trialkoxysilane |
| WO2011006049A1 (en) * | 2009-07-10 | 2011-01-13 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| WO2011006044A2 (en) * | 2009-07-10 | 2011-01-13 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5691435A (en) * | 1996-01-25 | 1997-11-25 | Wacker-Chemie Gmbh | Crosslinkable compositions |
| US5756795A (en) * | 1996-12-30 | 1998-05-26 | Dow Corning Corporation | Unsaturated accelerators for hydrosilation |
| US5986022A (en) * | 1998-04-01 | 1999-11-16 | Witco Corporation | Continuous manufacture of silicone coploymers |
| GB9819847D0 (en) * | 1998-09-12 | 1998-11-04 | Bp Chem Int Ltd | Novel compounds |
| WO2012071358A2 (en) * | 2010-11-24 | 2012-05-31 | Momentive Performance Materials Inc. | In-situ activation of metal complexes containing terdentate nitrogen ligands used as hydrosilylation catalysts |
-
2011
- 2011-11-22 CN CN201180065872.0A patent/CN103732599B/zh active Active
- 2011-11-22 KR KR1020137016391A patent/KR101896423B1/ko active Active
- 2011-11-22 EP EP11794591.5A patent/EP2643330B1/en active Active
- 2011-11-22 BR BR112013012734A patent/BR112013012734A2/pt not_active Application Discontinuation
- 2011-11-22 JP JP2013541003A patent/JP6019034B2/ja active Active
- 2011-11-22 WO PCT/US2011/061752 patent/WO2012071360A1/en not_active Ceased
- 2011-11-22 US US13/302,506 patent/US8895770B2/en active Active
- 2011-11-23 TW TW100142961A patent/TWI457176B/zh active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5166298A (en) | 1989-01-19 | 1992-11-24 | Essilor International (Compagnie Generale D'optique) | Oxygen-permeable transparent polymer compositions for contact lenses of the rigid type |
| US6265497B1 (en) | 1998-12-04 | 2001-07-24 | Wacker-Chemie Gmbh | Siloxane copolymers containing alkenyl groups |
| US6278011B1 (en) | 1999-08-30 | 2001-08-21 | The University Of Dayton | Polysilahydrocarbons as lubricants for aerospace application |
| US7429672B2 (en) | 2006-06-09 | 2008-09-30 | Momentive Performance Materials Inc. | Process for the direct synthesis of trialkoxysilane |
| WO2008085453A1 (en) * | 2006-12-28 | 2008-07-17 | Momentive Performance Materials Inc. | Silated core polysulfides, their preparation and use in filled elastomer compositions |
| US7696269B2 (en) | 2006-12-28 | 2010-04-13 | Momentive Performance Materials Inc. | Silated core polysulfides, their preparation and use in filled elastomer compositions |
| WO2011006049A1 (en) * | 2009-07-10 | 2011-01-13 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| US20110009565A1 (en) | 2009-07-10 | 2011-01-13 | Delis Johannes G P | Hydrosilylation Catalysts |
| WO2011006044A2 (en) * | 2009-07-10 | 2011-01-13 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| US20110009573A1 (en) | 2009-07-10 | 2011-01-13 | Delis Johannes G P | Hydrosilylation Catalysts |
Non-Patent Citations (7)
| Title |
|---|
| ARCHER A M ET AL: "Arene coordination in bis(imino) pyridine iron complexes: identification of catalyst deactivation pathways in iron-catalyzed hydrogenation and hydrosilation", ORGANOMETALLICS, ACS, WASHINGTON, DC, US, vol. 25, 28 August 2006 (2006-08-28), pages 4269 - 4278, XP002598590, ISSN: 0276-7333, [retrieved on 20060805], DOI: 10.1021/OM060441C * |
| JOURNAL OF CHROMATOGRAPHY A, vol. 1025, 2003, pages 65 - 71 |
| KIM ET AL., JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 673, 2003, pages 77 - 83 |
| MACROMOL. CHEM. PHYS., vol. 202, no. 5, 2001, pages 645 - 653 |
| PANGBORN ET AL., J. ORGANOMETALLICS, vol. 15, 1996, pages 1518 |
| SUZANNE C. BART ET AL: "Preparation and Molecular and Electronic Structures of Iron(0) Dinitrogen and Silane Complexes and Their Application to Catalytic Hydrogenation and Hydrosilation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 126, no. 42, 1 October 2004 (2004-10-01), pages 13794 - 13807, XP055017048, ISSN: 0002-7863, DOI: 10.1021/ja046753t * |
| WU ET AL., J. AM. CHEM. SOC., vol. 132, 2010, pages 13214 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10829504B2 (en) | 2016-01-22 | 2020-11-10 | Shin-Etsu Chemical Co., Ltd. | Isocyanide compound and hydrosilylation reaction catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103732599B (zh) | 2016-09-14 |
| KR20140035318A (ko) | 2014-03-21 |
| JP2014502271A (ja) | 2014-01-30 |
| CN103732599A (zh) | 2014-04-16 |
| TWI457176B (zh) | 2014-10-21 |
| KR101896423B1 (ko) | 2018-10-04 |
| JP6019034B2 (ja) | 2016-11-02 |
| TW201235102A (en) | 2012-09-01 |
| EP2643330A1 (en) | 2013-10-02 |
| US8895770B2 (en) | 2014-11-25 |
| EP2643330B1 (en) | 2017-01-04 |
| US20120130105A1 (en) | 2012-05-24 |
| BR112013012734A2 (pt) | 2016-09-13 |
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