GB907180A - A process for the preparation of alkenyl cycloalkanes - Google Patents

A process for the preparation of alkenyl cycloalkanes

Info

Publication number
GB907180A
GB907180A GB43572/60A GB4357260A GB907180A GB 907180 A GB907180 A GB 907180A GB 43572/60 A GB43572/60 A GB 43572/60A GB 4357260 A GB4357260 A GB 4357260A GB 907180 A GB907180 A GB 907180A
Authority
GB
United Kingdom
Prior art keywords
alkenyl
adduct
ring
anthracene
effected
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
GB43572/60A
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 GB907180A publication Critical patent/GB907180A/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
    • C07C2/50—Diels-Alder conversion
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/16—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
    • C07C13/18—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexane ring
    • C07C13/19—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexane ring substituted by unsaturated hydrocarbon groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
    • C07C13/68—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings with a bridged ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
    • C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C07C5/05—Partial hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2525/00—Catalysts of the Raney type
    • C07C2525/02—Raney nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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
    • C07C2603/86—Ring systems containing bridged rings containing four rings
    • C07C2603/88—Ethanoanthracenes; Hydrogenated ethanoanthracenes
    • 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

Abstract

Alkenyl cycloalkanes are obtained from alkenyl cycloalkenes by forming an adduct with a polycyclic fused ring hydrocarbon having two mess carbon atoms in 1 : 4 relationship in an aromatic ring, hydrogenating the olefinic link in the cycloolefinic ring and pyrolysing the adduct. The cycloolefinic group may be mono-or bi-cyclic containing 5-8 carbon atoms in each ring, the alkenyl group may contain 2-18 carbons and other C1-C5 alkyl groups may be present as ring substituents. Anthracene is the preferred polycyclic hydrocarbon, others are also specified. The adduct is formed by heating the ingredients at 150-275 DEG C. and 50-5,000 p.s.i. for 4-16, preferably with one reactant in an excess, e.g. up to a mol ratio of 2 : 1. An inert hydrocarbon solvent may be present in an amount of 1-100 parts per part of alkenyl cycloalkene. Reduction is effected at 30-150 DEG C. and a hydrogen pressure of 50-5,000 p.s.i. for 0.5-8 hours in the presence of a catalyst, e.g. Raney nickel, others also being specified. Pyrolysis is effected at 250-450 DEG C. for 2-60 minutes. 9,10-dihydro - 9,10 - (cyclohex-3-enyl)-ethano anthracene, the adduct of anthracene and 4-vinylcyclohexene is stated to be a novel compound.
GB43572/60A 1959-12-21 1960-12-19 A process for the preparation of alkenyl cycloalkanes Expired GB907180A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US860694A US3052737A (en) 1959-12-21 1959-12-21 Synthesis of alkenyl substituted cycloalkanes

Publications (1)

Publication Number Publication Date
GB907180A true GB907180A (en) 1962-10-03

Family

ID=25333809

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43572/60A Expired GB907180A (en) 1959-12-21 1960-12-19 A process for the preparation of alkenyl cycloalkanes

Country Status (3)

Country Link
US (1) US3052737A (en)
DE (1) DE1134073B (en)
GB (1) GB907180A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0559183A1 (en) * 1992-03-03 1993-09-08 Phillips Petroleum Company Selective hydrogenation of diolefins

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3356705A (en) * 1963-06-28 1967-12-05 Union Carbide Corp Trans-di (aluminoalkyl) cyclobutane polymers
US3346655A (en) * 1965-10-07 1967-10-10 Universal Oil Prod Co Preparation of unsaturated side chain cycloalkanes
US4915794A (en) * 1988-10-27 1990-04-10 Shell Oil Company Process for converting internal olefins to alpha olefins
US4946560A (en) * 1988-10-27 1990-08-07 Shell Oil Company Process for separating alpha and internal olefins
EP0366211B1 (en) * 1988-10-27 1993-02-03 Shell Internationale Researchmaatschappij B.V. Process for producing alpha olefins

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2406645A (en) * 1944-09-28 1946-08-27 Universal Oil Prod Co Synthesis of aromatic compounds
US2673886A (en) * 1951-07-18 1954-03-30 Goodrich Co B F Hydrogenation in presence of raney nickel

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0559183A1 (en) * 1992-03-03 1993-09-08 Phillips Petroleum Company Selective hydrogenation of diolefins

Also Published As

Publication number Publication date
DE1134073B (en) 1962-08-02
US3052737A (en) 1962-09-04

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