GB944440A - Production of 1,5-cyclo-octadiene from butadiene - Google Patents

Production of 1,5-cyclo-octadiene from butadiene

Info

Publication number
GB944440A
GB944440A GB24430/61A GB2443061A GB944440A GB 944440 A GB944440 A GB 944440A GB 24430/61 A GB24430/61 A GB 24430/61A GB 2443061 A GB2443061 A GB 2443061A GB 944440 A GB944440 A GB 944440A
Authority
GB
United Kingdom
Prior art keywords
nitrile
butadiene
complex
nickel
solvent
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
GB24430/61A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB944440A publication Critical patent/GB944440A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
    • C07C2/44—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion of conjugated dienes only
    • C07C2/46—Catalytic processes
    • C07C2/465—Catalytic processes with hydrides or organic compounds
    • 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
    • B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

A complex compound of zero-valent nickel and an ester of phosphorous acid free from carbon monoxide, is used as catalyst in the cyclising polymerization of butadiene. The complex is formed from a complex of nickel with an a , b -unsaturated aldehyde or nitrile, e.g. acrolein, g -bromocrotonaldehyde, acrylonitrile, crotonyl nitrile, cinnamyl nitrile or fumaronitrile, and a phosphite ester of an alkanol, naphthol or phenol which latter may contain alkyl, alkoxy, aryl or chlorine substituents. The mol ratio of nickel complex to phosphite may be 1:0 5 to 1:5 and each is added in amounts of 1 to 10% by weight to the solvent in which the polymerization is to be effected, such solvent being a hydrocarbon, including cyclooctadiene-1,5 or excess butadiene, a cyclic or acyclic amide, ether, or ketone or a nitrile. Specification 943,697 is referred to.ALSO:Cyclooctadiene-1,5 is formed by polymerizing butadiene at 20 DEG C. or more in a solvent or diluent in the presence of a catalyst formed by reacting in the absence of oxygen but in the presence of butadiene an organic complex compound of zero-valent nickel free from carbon monoxide and an ester of phosphorous acid. The solvent or diluent may be a hydrocarbon, including cyclooctadiene- 1,5, or excess liquid butadiene, a cyclic or acyclic amide, ether or ketone or a nitrile. The catalyst is formed from a complex of nickel with an a ,b -unsaturated aldehyde or nitrile including acrolein, g -bromocrotonaldehyde, acrylonitrile, crotonyl nitrile, cinnamyl nitrile and fumaronitrile. The phosphite ester may be of an alkanol, naphthol or phenol which latter may contain alkyl, alkoxy, aryl or chlorine substituents. The mole ratio of nickel complex to phosphite may be 1 : 0.5 to 1 : 5 and each is present in amounts of 1-10% by weight of solvent. Temperatures of ambient to 250 DEG C. and pressures of 3-20 atmospheres gauge may be used, higher pressures being obtained by the use of an inert gas if necessary. A polymerization inhibitor, e.g. of the phenol or amine type, may be present. The butadiene may be reacted in the liquid or vapour phase. Some 4-vinylcyclohexene-1 is also formed. Specification 943,697 is referred to.
GB24430/61A 1960-09-17 1961-07-06 Production of 1,5-cyclo-octadiene from butadiene Expired GB944440A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB59415A DE1298525B (en) 1960-09-17 1960-09-17 Process for the preparation of cyclooctadiene (1, 5) from butadiene in the presence of a complex nickel catalyst

Publications (1)

Publication Number Publication Date
GB944440A true GB944440A (en) 1963-12-11

Family

ID=6972460

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24430/61A Expired GB944440A (en) 1960-09-17 1961-07-06 Production of 1,5-cyclo-octadiene from butadiene

Country Status (3)

Country Link
DE (1) DE1298525B (en)
GB (1) GB944440A (en)
NL (2) NL269313A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE881511C (en) * 1950-09-12 1953-06-29 Ici Ltd Process for the preparation of cycloolefins with at least 8 carbon atoms in the ring
DE951213C (en) * 1951-11-19 1956-10-25 Ici Ltd Process for the production of cycloocta-1, 5-diene by dimerizing butadiene

Also Published As

Publication number Publication date
NL129844C (en) 1900-01-01
DE1298525B (en) 1969-07-03
NL269313A (en) 1900-01-01

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