Ethylidene Norbornene (ENB)

World leader pushing the boundaries of norbornene technology

INEOS Oxide is a leading global producer of ENB. Having been at the forefront of norbornene techno-logy
for almost thirty years, our customers have come to trust and depend on our high quality, consistent and
secure source of supply. Strategically, we are the only producer of these fine chemicals in Europe. Our stateof-the-art plant has a capacity of 20 ktpa.

Ethylidene Norbornene Production

ENB is manufactured by reacting 1,3-butadiene and dicyclopentadiene in a four-step process. In the first step, dicyclopentadiene is decoupled to cyclopentadiene and reacted with 1,3-butadiene via Diels-Alder condensation to vinylnorbornene (VNB). This is followed by distillation to obtain refined VNB, which is catalytically isomerized to ENB. Finally, the crude ENB is purified.

 

Applications

ENB is used predominantly as the diene monomer in the production of ethylene-propylene-diene rubber (EPDM); an extremely wear and weather resistant high performance rubber which is increasingly favoured for use in the automotive, white goods and construction industries.

The use of ENB is derived from the norbornene double bond which copolymerises with ethylene and propylene to produce an ethylene-propylene-terpolymer that contains the ethylidene double bond as residual unsaturation.
The ethylidene double bond is subsequently used to cure (vulcanise) the EPDM with sulphur in conventional vulcanising equipment. ENB infers fast, homogeneous vulcanisation characteristics o the rubber.

Because of its unique molecular structure, ENB is also used in the high value fragrance and flavours industry as a scent carrier. 

ENB, Acetate and Glycol Ether Esters
at a glance...
  • Annual Capacities
    ENB: 20kt
    Acetate ESters: 85kt
    Glycol Ether Esters: 25kt

  • Main Products
    ENB
    VNB
    4-Vinylcyclohexene
    Specialty Norbornenes

    n-Butyl Acetate
    iso-Butyl Acetate
    iso-Propyl Acetate
    Methoxy Propanol Acetate
    Ethoxy Propanol Acetate
    Butyl Glycol Acetate
    Butyl di Glycol Acetate

  • Key Applications
    EPDM rubbers
    Fragrances and Flavours
    Cyclic Olefin Copolymers
    Pharmaceutical intermediates
    Agrochemicals

    Coatings (paints and lacquers)
    Inks
    Sealants
    Adhesives
    Pharmaceuticals
    Textiles
Novel norbornenes, pioneered by INEOS Oxide, are also being used in a host of emerging technologies including high performance cyclic olefin copolymers for electronic and optical applications, in new types of EPDM rubbers, in agrochemicals and in pharmaceuticals. Because of the unique chemical solutions that only norbornenes can provide, INEOS Oxide developed new norbornene molecules in collaboration with partners in a wide range of industries. Laboratory and small pilot plant reaction/distillation facilities are available for the manufacture of novel bespoke norbornenes, based on the reaction of dicyclopentadiene with a host of unsaturated compounds.