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    Acetylene Dienes

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    Nitty MeYa
    Acetylene was once an important raw material but has been replaced by olefins. It is produced from calcium carbide and by cracking hydrocarbons. Acetylene is used for welding and to produce intermediates like 1,4-butanediol via the Reppe process. 1,3-Butadiene and isoprene are important 1,3-diolefins produced from acetylene or hydrocarbon cracking that are used to make various polymers and other products. Chloroprene, a synthetic rubber precursor, is synthesized from acetylene or butadiene.

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    Acetylene Dienes

    Uploaded by

    Nitty MeYa
    138 views16 pages
    Acetylene was once an important raw material but has been replaced by olefins. It is produced from calcium carbide and by cracking hydrocarbons. Acetylene is used for welding and to produce intermediates like 1,4-butanediol via the Reppe process. 1,3-Butadiene and isoprene are important 1,3-diolefins produced from acetylene or hydrocarbon cracking that are used to make various polymers and other products. Chloroprene, a synthetic rubber precursor, is synthesized from acetylene or butadiene.

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    industrial chemistry

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    Acetylene was once an important raw material but has been replaced by olefins. It is produced from calcium carbide and by cracking hydrocarbons. Acetylene is used for welding and to produce intermediates like 1,4-butanediol via the Reppe process. 1,3-Butadiene and isoprene are important 1,3-diolefins produced from acetylene or hydrocarbon cracking that are used to make various polymers and other products. Chloroprene, a synthetic rubber precursor, is synthesized from acetylene or butadiene.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    138 views16 pages

    Acetylene Dienes

    Uploaded by

    Nitty MeYa
    Acetylene was once an important raw material but has been replaced by olefins. It is produced from calcium carbide and by cracking hydrocarbons. Acetylene is used for welding and to produce intermediates like 1,4-butanediol via the Reppe process. 1,3-Butadiene and isoprene are important 1,3-diolefins produced from acetylene or hydrocarbon cracking that are used to make various polymers and other products. Chloroprene, a synthetic rubber precursor, is synthesized from acetylene or butadiene.

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    Acetylene

    Acetylene (ethyne) was one of the most important raw materials up to the 1950s, but has largely been replaced by olefins Acetylene is used for welding More intermediates are now manufactured from ethylene rather than acetylene Coal is the basis of acetylene production today, and the bulk of acetylene is derived from calcium carbide, CaC2

    Production of acetylene
    From calcium carbide CaC2 + H2O HCCH + Ca(OH)2 (H = -130 kJ/mol) Cracking of hydrocarbons. High temperatures (>14000C), short residence times (0.01 to 0.001 sec), low partial pressures of acetylene and rapid quenching of the pyrolyzed gases aer essential to facilitate this process Autothermal cracking process of BASF: feedstocks such as methane, liquid gas or light gasoline is used 2CH4 C2H2 + 3H2 (H = +377 kJ/mol)

    Uses of acetylene
    Manufacture of 1,4butanediol by the Reppe process : Reaction with formaldehyde produces 2-butyne-1,4-diol 2-butyne-1,4-diol is hydrogenated to 1,4butanediol

    1.

    2.

    the presence of the triple bond weakens this bond, making the C-H functional group very weakly acidic -H+ H C
    C H

    acetynilide ion (a nucleophile) R R H C


    C

    + R'

    HC

    O-

    R'

    Tetrahydrofuran (THF), and aprotic organic solvent (it is an ether) is be prepared by dehydrating 1.4-butanediol using phosphoric acid, sulphuric acid or acidic ion exchangers

    1,3-diolefins
    1,3-diolefins or dienes have two conjugated double bonds, and are more reactive than unconjugated dienes Industrially important dienes include: - butadiene - chloroprene - isoprene - cyclopentadiene

    Production of 1,3-butadiene
    1. From acetaldehyde. It is a 4-step process: (i) the conversion of acetylene to acetaldehyde, (ii) an aldol addition, (iii) reduction using a Ni catalyst, (iv) dehydration using a sodium polyphosphate catalyst

    2. Cracking of natural or refinery gas produces butadiene

    Uses of 1.3-butadiene
    1. Polymerization products include elastomers, thermoplasts, drying oils. (Elastomers are polymers that exhibit elastic activity upon cross-linking or vulcanization.) Synthetic rubbers include styrene butadiene rubber (developed by IG Farben, originally called Buna S) and butadiene rubber. Styrene butadiene rubber structure is shown on the right: Synthesis of intermediate products by addition, sulfone formation and selective hydrogenation

    2.

    3. Production of 1,4-butanediol, developed by Eastman Chemical

    4. Production of sulfolane (tetrahydrothiophene dioxide), an extremely stable aprotic industrial solvent

    Isoprene (2-methyl-1,3-butadiene)
    Methods of production: 1. From naphtha C5 cracking fractions, where the isoprene content may be 1423%, the other components being pentane, pentenes and cyclopentadiene 2. Isoprenes may be isolated by extractive distillation or fractional distillation

    Production of isoprene by the acetone-acetylene process: the first step reacts acetone and acetylene in liquid ammonia at 30-400C at 20 bar with KOH as the catalyst. This is followed by selective hydrogenation, then by dehydration on Al2O3

    Chloroprene
    Third in importance to butadiene and isoprene Building block for synthetic rubber (chloroprene rubber) The most used route to obtain chloroprene is synthesis from acetylene

    Synthesis of chloroprene from acetylene


    1. Dimerization of acetylene to vinylacetylene in aqueous HCl with CuCl and ammonium chloride at 800C. Addition of HCl to vinylacetylene, forming chloroprene

    2.

    Synthesis of chloroprene from butadiene


    1. Radical addition of Cl2 forming a dichlorobutene mixture

    2. Dehydrochlorination with dilute alkali solutions (this is an elimination reaction)

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