GB1210969A - Isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles - Google Patents

Isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles

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Publication number
GB1210969A
GB1210969A GB4841768A GB4841768A GB1210969A GB 1210969 A GB1210969 A GB 1210969A GB 4841768 A GB4841768 A GB 4841768A GB 4841768 A GB4841768 A GB 4841768A GB 1210969 A GB1210969 A GB 1210969A
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GB
United Kingdom
Prior art keywords
alkyl
formula
methyl
carbon atoms
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.)
Expired
Application number
GB4841768A
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
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1210969A publication Critical patent/GB1210969A/en
Expired legal-status Critical Current

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    • 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
    • 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
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
    • 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
    • B01J31/16—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
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=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
    • B01J31/16—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
    • B01J31/1895—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 arsenic or antimony
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/52—Isomerisation reactions
    • 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

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)
  • Catalysts (AREA)

Abstract

1,210,969. Isomerization of 2-methyl-3- butene nitrile to linear pentenenitriles. E.I. DU PONT DE NEMOURS & CO. 11 Nov., 1968 [26 Oct., 1967], No. 48417/68. Heading C2C. 2 - Methyl - 3 - butenenitrile is isomerized to linear pentenenitriles by contacting it with a catalyst comprising (a) a zero-valent nickel complex which is a nickel compound of the formula Ni(PXYZ) 4 where X is OR and Y and Z are OR or R, wherein R is an alkyl or aryl group having up to 18 carbon atoms and wherein any of X, Y and Z may be cojoined, and (b) an organoboron compound of the Formula B(R) 3 , wherein R is an alkyl or aryl group containing up to 18 carbon atoms, or a salt of a metal of atomic number 13, 21-32, 39-50 or 57-82, the molar ratio of (b) to (a) being from 1 : 20 to 50 : 1. The reaction may be effected batchwise or continuously at a temperature of 10-200‹ C., preferably under an inert, atmosphere, and an inert solvent may be present. Preferred catalysts are those wherein the nickel complex is (1) a preformed complex of the formula Ni(PXYZ) 4 where any two of X, Y and Z are alkylene or alkoxylene of up to 6 carbons, the third of X, Y and Z being as defined above; or (2) the product of reaction between an alkyl or aryl phosphite with an intermediate nickel compound of the formula Ni(A<SP>1</SP>)(A<SP>2</SP>)(A<SP>3</SP>)(A<SP>4</SP>), where A<SP>1</SP>-A<SP>4</SP> are the same or different neutral ligands and are each (a) carbon monoxide or (b) M(X<SP>1</SP>Y<SP>1</SP>Z<SP>1</SP>) wherein M is P, As or Sb n and X<SP>1</SP>, Y<SP>1</SP> and Z<SP>1</SP> are the same or different and are R 1 , NR 2 , Cl or F, R being alkyl or aryl of up to 18 carbon atoms, or A<SP>1</SP> and A<SP>2</SP> are, together, a single acrylonitrile molecule and A<SP>3</SP> and A<SP>4</SP> are together a single acrylonitrile molecule or each a group M(X<SP>1</SP>Y<SP>1</SP>Z<SP>1</SP>) as defined above; both the final zero-valent nickel complex and the intermediate nickel compound may be pre-formed or formed in situ. The anions in the metal salts employed as promotors may be, for example, halides, sulphates, phosphates and aliphatic carboxylates.
GB4841768A 1967-10-26 1968-10-11 Isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles Expired GB1210969A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US67821667A 1967-10-26 1967-10-26
US75857868A 1968-09-09 1968-09-09

Publications (1)

Publication Number Publication Date
GB1210969A true GB1210969A (en) 1970-11-04

Family

ID=27101978

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4841768A Expired GB1210969A (en) 1967-10-26 1968-10-11 Isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles

Country Status (5)

Country Link
BE (1) BE722807A (en)
DE (1) DE1805278A1 (en)
FR (1) FR1589943A (en)
GB (1) GB1210969A (en)
NL (2) NL142667B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1351694A (en) * 1970-10-02 1974-05-01 Du Pont Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles
US3852328A (en) * 1973-09-26 1974-12-03 Du Pont Catalytic isomerization of 2-methyl-3-butenenitrile to a linear pentenenitrile

Also Published As

Publication number Publication date
DE1805278A1 (en) 1969-07-17
NL7405422A (en) 1974-06-25
NL6815313A (en) 1969-04-29
FR1589943A (en) 1970-04-06
NL142667B (en) 1974-07-15
BE722807A (en) 1969-04-01

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