GB1108379A - Process for the preparation of dimers of bicyclo-[2,2,1]-hepta-2,5-diene and its alkyl derivatives - Google Patents

Process for the preparation of dimers of bicyclo-[2,2,1]-hepta-2,5-diene and its alkyl derivatives

Info

Publication number
GB1108379A
GB1108379A GB53095/66A GB5309566A GB1108379A GB 1108379 A GB1108379 A GB 1108379A GB 53095/66 A GB53095/66 A GB 53095/66A GB 5309566 A GB5309566 A GB 5309566A GB 1108379 A GB1108379 A GB 1108379A
Authority
GB
United Kingdom
Prior art keywords
dimers
hepta
bicyclo
diene
iron
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
GB53095/66A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB1108379A publication Critical patent/GB1108379A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/90—Ring systems containing bridged rings containing more than four rings
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The dimerization of bicyclo[2,2,1]hepta-2,5-diene or an alkyl derivative thereof boiling below 140 DEG C. is effected at atmospheric pressure and at a temperature above 140 DEG C. in the presence of a catalyst consisting of a complex compound of iron in a low oxidation state as central atom and having at least in part electron donating compounds as ligands. Suitable ligands are bicyclo[2,2,1]hepta-2,5-diene itself, its dimers, and Lewis bases, e.g. a triarylphosphine. The catalyst is preferably produced in situ by mixing a solution of a catalytically inactive iron compound such as iron (III) acetyl acetonate with a solution of a reducing agent such as aluminium triethyl, the solvent in each case being the monomer itself. The mixing of the two solutions may be conducted in the presence of a small amount of dimer. The process is preferably carried out continuously in the absence of solvents and under a blanket of inert gas, e.g. nitrogen. If a solvent is desired benzene, xylene and THF are suitable. The dimer mixture formed contains structural isomers of the following structures. <PICT:1108379/C4-C5/1> <PICT:1108379/C4-C5/2> The dimers may be hydrogenated at room temperature, at atmospheric pressure, in the absence of solvents, and in the presence of Raney nickel catalyst. The dimers are suitable as fuels for jet aircraft, and may be mixed with conventional fuels, e.g. gasoline, kerosene and JP4 fuel.
GB53095/66A 1965-11-29 1966-11-28 Process for the preparation of dimers of bicyclo-[2,2,1]-hepta-2,5-diene and its alkyl derivatives Expired GB1108379A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DES100715A DE1239304B (en) 1965-11-29 1965-11-29 Process for the preparation of the dimers of bicyclo- [2, 2, 1] -heptadiene-2, 5 and its alkyl derivatives boiling below 140

Publications (1)

Publication Number Publication Date
GB1108379A true GB1108379A (en) 1968-04-03

Family

ID=7523251

Family Applications (1)

Application Number Title Priority Date Filing Date
GB53095/66A Expired GB1108379A (en) 1965-11-29 1966-11-28 Process for the preparation of dimers of bicyclo-[2,2,1]-hepta-2,5-diene and its alkyl derivatives

Country Status (5)

Country Link
US (1) US3377398A (en)
DE (1) DE1239304B (en)
FR (1) FR1517799A (en)
GB (1) GB1108379A (en)
NL (1) NL6616689A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4031150A (en) * 1975-11-14 1977-06-21 Suntech, Inc. Catalytic dimerization of norbornadiene to Binor-S

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3440294A (en) * 1967-04-07 1969-04-22 Union Carbide Corp Oligomers of bicycloheptadiene
US3671597A (en) * 1970-07-17 1972-06-20 Exxon Research Engineering Co Isomerization process employing a novel heterogeneous catalyst
US4087257A (en) * 1977-03-21 1978-05-02 The United States Of America As Represented By The Secretary Of The Navy High density-high volumetric heating value liquid ramjet
US4401837A (en) * 1980-06-02 1983-08-30 The United States Of America As Represented By The Secretary Of The Navy Exo-tetrahydrotricyclopentadiene, a high density liquid fuel
KR101616071B1 (en) 2015-10-21 2016-04-27 국방과학연구소 Method for producing norbornadiene dimer using hetorogneous catalyst
KR101976075B1 (en) 2018-03-30 2019-08-28 국방과학연구소 Composition for manufacturing high-energy density power source, high-energy density power source composition and method for manufacturing high-energy density power source composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE626407A (en) *
DE1197083B (en) * 1961-12-27 1965-07-22 Shell Int Research Process for the preparation of dimers and trimers of bicyclo- [2, 2, 1] -heptadiene- (2, 5)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4031150A (en) * 1975-11-14 1977-06-21 Suntech, Inc. Catalytic dimerization of norbornadiene to Binor-S

Also Published As

Publication number Publication date
FR1517799A (en) 1968-03-22
US3377398A (en) 1968-04-09
DE1239304B (en) 1967-04-27
NL6616689A (en) 1967-05-30

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