WO1996011182A1 - Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor - Google Patents

Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor Download PDF

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Publication number
WO1996011182A1
WO1996011182A1 PCT/US1995/012214 US9512214W WO9611182A1 WO 1996011182 A1 WO1996011182 A1 WO 1996011182A1 US 9512214 W US9512214 W US 9512214W WO 9611182 A1 WO9611182 A1 WO 9611182A1
Authority
WO
WIPO (PCT)
Prior art keywords
ligand
alkyl
adn
zncl
independently
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
Application number
PCT/US1995/012214
Other languages
English (en)
French (fr)
Inventor
Kristina Ann Kreutzer
Wilson Tam
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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
Priority claimed from US08/505,137 external-priority patent/US5512696A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to EP95935101A priority Critical patent/EP0784610B1/en
Priority to BR9509494A priority patent/BR9509494A/pt
Priority to KR1019970702236A priority patent/KR100257363B1/ko
Priority to DE69507819T priority patent/DE69507819T2/de
Priority to CA002200303A priority patent/CA2200303C/en
Priority to JP51259296A priority patent/JP3535172B2/ja
Publication of WO1996011182A1 publication Critical patent/WO1996011182A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
    • C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
    • 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
    • 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
    • B01J31/1845—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 phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • 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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • 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
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
    • 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
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
    • B01J2531/84—Metals of the iron group
    • B01J2531/847—Nickel

Definitions

  • the Lewis acid is considered to be a promoter.
  • x is an integer of 1 to 12 when R 4 is CN;

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/US1995/012214 1994-10-07 1995-09-29 Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor Ceased WO1996011182A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP95935101A EP0784610B1 (en) 1994-10-07 1995-09-29 Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor
BR9509494A BR9509494A (pt) 1994-10-07 1995-09-29 Processo de hidrocianação e composição de catalisador
KR1019970702236A KR100257363B1 (ko) 1994-10-07 1995-09-29 하이드로시안화 공정 및 이의 다좌 아인산염 및니켈 촉매 조성물
DE69507819T DE69507819T2 (de) 1994-10-07 1995-09-29 Hydrocyanierungsverfahren und darin verwendbare katalysatorzusammensetzungen aus nickel und mehrzähnigen phosphiten
CA002200303A CA2200303C (en) 1994-10-07 1995-09-29 Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor
JP51259296A JP3535172B2 (ja) 1994-10-07 1995-09-29 ヒドロシアン化方法およびそれ用の多座ホスファイトとニッケルの触媒組成物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US32002594A 1994-10-07 1994-10-07
US08/320,025 1994-10-07
US08/505,137 US5512696A (en) 1995-07-21 1995-07-21 Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor
US08/505,137 1995-07-21

Publications (1)

Publication Number Publication Date
WO1996011182A1 true WO1996011182A1 (en) 1996-04-18

Family

ID=26982258

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/012214 Ceased WO1996011182A1 (en) 1994-10-07 1995-09-29 Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor

Country Status (13)

Country Link
US (1) US5663369A (OSRAM)
EP (1) EP0784610B1 (OSRAM)
JP (1) JP3535172B2 (OSRAM)
KR (1) KR100257363B1 (OSRAM)
CN (1) CN1047163C (OSRAM)
AT (1) ATE176665T1 (OSRAM)
BR (1) BR9509494A (OSRAM)
CA (1) CA2200303C (OSRAM)
DE (1) DE69507819T2 (OSRAM)
ES (1) ES2129234T3 (OSRAM)
MY (1) MY112815A (OSRAM)
TW (1) TW315370B (OSRAM)
WO (1) WO1996011182A1 (OSRAM)

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997033892A1 (en) * 1996-03-15 1997-09-18 Dsm N.V. Process to prepare a multidentate phosphite compound
WO1997033854A1 (en) * 1996-03-15 1997-09-18 Dsm N.V. Process to prepare a terminal aldehyde
EP0839787A1 (en) * 1996-11-04 1998-05-06 Dsm N.V. Process for the preparation of an aldehyde
WO1999006355A1 (en) * 1997-07-29 1999-02-11 E.I. Du Pont De Nemours And Company Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles
WO1999006345A1 (en) * 1997-07-29 1999-02-11 E.I. Du Pont De Nemours And Company Improved process of preparation of linear aldehydes
WO1999006359A1 (en) * 1997-07-29 1999-02-11 E.I. Du Pont De Nemours And Company Improved hydrocyanation process
WO1999006356A1 (en) * 1997-07-29 1999-02-11 E.I. Du Pont De Nemours And Company Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions therefor
WO1999006358A1 (en) * 1997-07-29 1999-02-11 E.I. Du Pont De Nemours And Company Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions therefor
US5910600A (en) * 1996-04-30 1999-06-08 Mitsubishi Chemical Corporation Bisphosphite compound, process for its production and hydroformylation process employing the bisphosphite compound
US6197992B1 (en) 1996-12-16 2001-03-06 Basf Aktiengesellschaft Monoolefinic C5 mononitriles, method for the production and the use thereof
WO2001021684A1 (en) * 1999-09-20 2001-03-29 E.I. Du Pont De Nemours And Company Polymeric phosphite composition and hydrocyanation of unsaturated organic compounds and the isomerization of unsaturated nitriles
WO2001021579A1 (en) * 1999-09-20 2001-03-29 E.I. Du Pont De Nemours And Company Multidentate phosphite ligands, catalytic compositions containing such ligands and catalytic processes utilizing such catalytic compositions
US6242633B1 (en) 1997-09-12 2001-06-05 Basf Aktiengesellschaft Catalyst comprising at least one phosphonite ligand based nickel (O) complex and method for the production of nitriles
JP2002509550A (ja) * 1997-07-29 2002-03-26 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ジオレフィンのヒドロシアノ化および非共役２−アルキル−３−モノアルケンニトリル類の異性化
US6486359B1 (en) 1998-06-18 2002-11-26 Basf Aktiengesellschaft Catalyst comprising a complex of a metal of subgroup viii based on a phosphinite ligand, and a method for hydroformylation
US6521778B1 (en) 1998-06-05 2003-02-18 Basf Aktiengesellschaft Catalyst comprising a complex of a metal from subgroup VIII based on a bidentate phosphonite ligand, and method for producing nitriles
FR2842197A1 (fr) * 2002-07-15 2004-01-16 Rhodia Polyamide Intermediates Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique
EP1571172A1 (en) * 2001-11-26 2005-09-07 E.I. du Pont de Nemours and Company Polymeric, phosphorus-containing compositions and their use in hydrocyanation, isomerization and hydroformylation reactions
WO2010042313A1 (en) * 2008-10-08 2010-04-15 Dow Technology Investments Llc Slurry process for synthesis of bisphosphites
US7880028B2 (en) 2006-07-14 2011-02-01 Invista North America S.A R.L. Process for making 3-pentenenitrile by hydrocyanation of butadiene
US7919646B2 (en) 2006-07-14 2011-04-05 Invista North America S.A R.L. Hydrocyanation of 2-pentenenitrile
US7973174B2 (en) 2005-10-18 2011-07-05 Invista North America S.A.R.L. Process of making 3-aminopentanenitrile
US7977502B2 (en) 2008-01-15 2011-07-12 Invista North America S.A R.L. Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile
US8088943B2 (en) 2008-01-15 2012-01-03 Invista North America S.A R.L. Hydrocyanation of pentenenitriles
US8101790B2 (en) 2007-06-13 2012-01-24 Invista North America S.A.R.L. Process for improving adiponitrile quality
US8178711B2 (en) 2006-03-17 2012-05-15 Invista North America S.A R.L. Method for the purification of triorganophosphites by treatment with a basic additive
US8247621B2 (en) 2008-10-14 2012-08-21 Invista North America S.A.R.L. Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols
US8338636B2 (en) 2009-08-07 2012-12-25 Invista North America S.A R.L. Hydrogenation and esterification to form diesters
US8373001B2 (en) 2003-02-10 2013-02-12 Invista North America S.A R.L. Method of producing dinitrile compounds
US8471066B2 (en) 2008-03-28 2013-06-25 Union Carbide Chemicals & Plastics Technology Llc Slurry process for phosphoromonochloridite synthesis
EP3318569A1 (de) * 2016-11-08 2018-05-09 Evonik Degussa GmbH Bisphosphite mit 2,4-tert.-butylphenyl-einheiten und deren verwendung als liganden in der hydroformylierung

Families Citing this family (40)

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US6069267A (en) * 1997-07-29 2000-05-30 E. I. Du Pont De Nemours And Company Selective synthesis of organodiphosphite compounds
JP3812095B2 (ja) 1997-10-28 2006-08-23 三菱化学株式会社 アルデヒド類の製造方法及びこれに用いるビスホスファイト
DE60031697T2 (de) 1999-09-20 2007-10-25 Invista Technologies S.A.R.L., Wilmington Multidentat-Phosphit-Liganden, und sie enthaltende katalytische Zusammensetzungen
US6515161B1 (en) 1999-09-20 2003-02-04 E. I. Du Pont De Nemours And Company Hydroformylation process utilizing multidentate phosphite ligands
US6420611B1 (en) * 1999-09-20 2002-07-16 E. I. Du Pont De Nemours And Company Composition comprising polymeric phosphite
US6893996B2 (en) 2001-11-26 2005-05-17 Invista North America S.A.R.L. Process for the preparation of a nickel/phosphorous ligand catalyst for olefin hydrocyanation
FR2842196B1 (fr) * 2002-07-15 2006-01-13 Rhodia Polyamide Intermediates Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique
US6906218B2 (en) 2002-12-18 2005-06-14 Invista North America S.A.R.L. Cyclohexane derivatives and methods for their preparation
FR2849027B1 (fr) * 2002-12-23 2005-01-21 Rhodia Polyamide Intermediates Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques
US6936171B2 (en) * 2003-01-08 2005-08-30 Invista North America S.A.R.L. Process for catalyst recovery from hydrocyanation product mixtures
US6897329B2 (en) 2003-01-14 2005-05-24 Invista North America S.A.R.L. Process for the preparation of nickel/phosphorous ligand catalyst for olefin hydrocyanation
US6844289B2 (en) * 2003-04-08 2005-01-18 Invista North America S.A.R.L. Process for the preparation of a nickel/phosphorous ligand catalyst
FR2854891B1 (fr) 2003-05-12 2006-07-07 Rhodia Polyamide Intermediates Procede de preparation de dinitriles
FR2854892B1 (fr) 2003-05-12 2005-06-24 Rhodia Polyamide Intermediates Procede de fabrication de dinitriles
WO2005026106A1 (en) 2003-09-11 2005-03-24 Invista Technologies S.A R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
US7740861B2 (en) 2004-06-16 2010-06-22 University Of Massachusetts Drug delivery product and methods
US8119829B2 (en) * 2004-09-08 2012-02-21 Invista North America S.A.R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
US7709673B2 (en) * 2006-07-14 2010-05-04 Invista North America S.A R.L. Process for making 3-pentenenitrile by hydrocyanation of butadiene
US7709674B2 (en) 2006-07-14 2010-05-04 Invista North America S.A R.L Hydrocyanation process with reduced yield losses
WO2009075692A2 (en) 2007-05-14 2009-06-18 Invista Technologies S.A.R.L. High efficiency reactor and process
EP2222283A2 (en) * 2007-10-29 2010-09-01 University of Massachusetts Yeast cell wall protein (ycwp) encapsulated multilayered nanoparticles for nucleic acid delivery (sirna)
US8097749B2 (en) * 2008-03-28 2012-01-17 Union Carbide Chemical and Plastics Technology Technology Isothermal process for phosphoromonochloridite synthesis
SG175257A1 (en) * 2009-04-21 2011-12-29 Invista Tech Sarl Highly selective process for producing organodiphosphites
KR20150035479A (ko) 2011-12-21 2015-04-06 인비스타 테크놀러지스 에스.에이 알.엘. 안정한 에멀젼을 감소시키기 위한 추출 용매 제어
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EP2794046B1 (en) 2011-12-21 2016-02-03 Invista Technologies S.A R.L. Extraction solvent control for reducing stable emulsions
US9133223B2 (en) 2011-12-21 2015-09-15 Invista North America S.A.R.L. Extraction solvent control for reducing stable emulsions
US9458185B2 (en) 2012-02-10 2016-10-04 The Regents Of The University Of California First row metal-based catalysts for hydosilylation
WO2015200630A1 (en) 2014-06-27 2015-12-30 Invista North America S.A R.L. Integrated process for nitrile manufacture with enhanced liquid-liquid extraction
WO2015200597A1 (en) 2014-06-27 2015-12-30 Invista North America S.A R.L. Enhanced extraction of impurities from mixture comprising nitriles
CN110997608B (zh) * 2017-08-24 2023-07-25 三菱化学株式会社 二羟基联苯化合物、双亚磷酸酯化合物、催化剂、醛类的制造方法以及醇的制造方法
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WO2024028718A1 (en) 2022-08-02 2024-02-08 Inv Nylon Chemicals Americas, Llc Bidfntate phosphite ligands. catalytic compositions containing such ligands. and catalytic processes utilizing such catalytic compositions

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EP0784610A1 (en) 1997-07-23
JP3535172B2 (ja) 2004-06-07
TW315370B (OSRAM) 1997-09-11
CN1159799A (zh) 1997-09-17
JPH10506911A (ja) 1998-07-07
US5663369A (en) 1997-09-02
CA2200303A1 (en) 1996-04-18
EP0784610B1 (en) 1999-02-10
KR100257363B1 (ko) 2000-05-15
BR9509494A (pt) 1997-10-14
CN1047163C (zh) 1999-12-08
DE69507819T2 (de) 1999-08-12
ES2129234T3 (es) 1999-06-01
CA2200303C (en) 2007-01-09
DE69507819D1 (de) 1999-03-25

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