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    4.1- Chemistry of Thermal Cracking

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    4.1- Chemistry of Thermal Cracking

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    4.1- Chemistry of Thermal Cracking

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    Chemistry of Thermal Cracking

    • Free radicals (reactive species with • The three steps of free radical chain
    unpaired electrons, but no reactions as: initiation, propagation, and
    termination.
    electronic charge) are the active
    • In the figure, R-H represents a paraffin chain
    species that govern thermal cracking which can be expanded such as (H3-(CH2)n –
    reactions. H) where n represents the number of carbon
    • Because of the free radical atoms in the alkane.
    chemistry, thermal cracking of gas oil • In other words, R represents a radical with an
    would produce gasoline with unpaired electron that becomes an alkane (R-
    H) when combined with a hydrogen atom.
    relatively low octane numbers, as
    will be discussed later in this section. • A Hydrogen atom with one proton and one
    electron is the simplest radical.
    Chemistry of Thermal Cracking

    The free radical chain reaction starts with breaking the weakest C-C
    bond in the reactant alkane (R-H) to form two free radicals R1 and R2,
    each with one unpaired electron resulting from the homolysis of the
    C-C bond (initiation).
    Once formed by the initiation step, each free radical can go through
    two different propagation reactions:

    1.Hydrogen abstraction
    2.Beta (β) scission
    Chemistry of Thermal Cracking

    In a hydrogen abstraction reaction,:


    for example, the radical R1 removes (abstracts) a hydrogen atom from an alkane (R-
    H) to produce a shorter chain alkane product (R1-H) and a new radical R (hydrogen
    abstraction), thus propagating the free radical chain.

    Alternatively, the radical R1, (or R2) can go through a β scission reaction to produce
    an olefin (ethylene) as a product, and a radical R to propagate the chain.
    The β scission refers to the breaking of the covalent bond in the β position relative
    to the position of the unpaired electron, as shown below:
    Chemistry of Thermal Cracking
    Note that the initiation step produces two free radicals, the propagation step produces a reaction product and
    one radical to continue the chain. The last step in the chain reaction, the termination step, removes two
    radicals to produce one or two stable compounds depending on the termination reaction, as seen in the Figure.

    The principal end result of the free radical chain reactions in thermal cracking is to produce from long chain
    alkanes shorter-chain alkanes, light olefins, and some aromatic compounds.

    One important feature of free radical reactions is that isomerization reactions, e.g., shifting of the unpaired
    electron site from an edge atom of a molecule to the interior atoms, are not favored reactions. In other words,
    isomerization reactions take place at a slower rate than other propagation reactions, e.g., β scission reaction.

    The critical importance of this observation is that the thermal cracking reactions produce shorter straight-chain
    alkanes and olefins without any significant formation of branched-chain (or iso-alkanes). This is the reason why
    catalytic cracking processes have virtually replaced thermal cracking processes to produce high octane number
    gasoline, as will be discussed in the next section on catalytic cracking.

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