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  • Existen Principalmente Dos Métodos: El Método Clorohidrin y La Oxidación Indirecta

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    Stefano D'Amico
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    Oxido de Propileno

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    Oxido de Propileno

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    Oxido de Propileno

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    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
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    14 views4 pages

    Existen Principalmente Dos Métodos: El Método Clorohidrin y La Oxidación Indirecta

    Uploaded by

    Stefano D'Amico
    Oxido de Propileno

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Flag for inappropriate content
    of 4

    1.

    Propiedades químicas y físicas


    Tabla 1
    Chemical Name or Material (±)-Propylene oxide
    Additional Information Vapor Pressure: 590mbar at 20°C
    Infrared Spectrum Authentic
    Refractive Index 1.3650 to 1.3670
    Specific Gravity 0.83
    Assay Percent Range 99%
    Water 0.02% max
    Boiling Point 34.0°C
    Color Undesignated
    Melting Point -112.0°C
    Flash Point −37°C
    Formula Weight 58.08
    Purity Grade Pure
    Assay 99%
    Molecular Formula C3H6O
    Molecular Weight (g/mol) 58.08
    Density 0.8300g/mL
    Physical Form Liquid
    Flammable limits 2 - 37% by volume in air
    Odour Ethereal
    From: Jacobson et al. (1956) and Hellman & Small (1974).

    2. Métodos de obtención industrial.


    Método de producción
    Existen principalmente dos métodos: el método clorohidrin y la oxidación indirecta

    There are mainly chlorohydrin method and indirect oxidation.

    1. Chlorohydrin method; aplica propileno, cloro y agua para acidificar por hipocloruros a 60°C
    a presión normal para generar cloroporpanol, acto seguido por procesos de
    saponificación, condensación y destilación
    2. oxidación indirecta: Se deriva de la oxidación de etilbenceno para formar hydrogen
    peroxide ethylbenzene, que luego tiene epoxidation with propylene in the catalysis of
    naphthenic acid molybdenum. 3)

    Electrochemical Chlorohydrin Method: this method is based on the principle that the aqueous
    solution of sodium chloride (or potassium chloride, sodium bromide, sodium iodide) for
    electrolysis to generate chlorine and so dium hydroxide. Send the propylene in the anode area to
    generate chlorine alcohol, which further reacts with sodium hydroxide to generate propylene
    oxide in the cathode area.
    The preparation method is as follows.
    (1) Chlorohydrin method
    Take propylene as raw materials, followed by hypochlorous acidification, saponification, and then
    enrichment and distillation to derive the products.
    The reaction of propylene with hypochlorous acid is carried out in an aqueous solution, and the
    chlorine gas is mixed with hypochlorous acid and hydrochloric acid in water. The reaction
    temperature is 30-50 DEG C, and the produced aqueous chloropropanol and 10% lime milk are
    saponified in a saponification reactor for saponification; the saponification kettle is sent into the
    water vapor, steaming out the propylene oxide, and then subject to condensed distillation derived
    products.

    𝐶𝐻3 𝐶𝐻 → 𝐶𝐻2 + 𝐻𝑂𝐶𝑙 → 𝐶𝐻3 𝐶𝐻𝑂𝐻𝐶𝐻2 𝐶𝑙 + 𝐶𝐻3 𝐶𝐻𝐶𝑙𝐶𝐻2𝑂𝐻

    This method requires a low purity of propylene, and the yield is high, but it consuming large
    amounts of chlorine and lime milk, equipment with serious corrosion on the device, resulting in
    environmental pollution problems. It is mainly adopted in China to produce propylene oxide.

    (2) Peroxide method


    The main process is the manufacture of organic hydrogen peroxide. Apply peroxide for oxidation
    of propylene. This reaction is always liquid phase reaction either in the production of organic
    hydrogen peroxide or in the presence of a catalyst for the transfer of oxygen from the peroxide to
    the propylene molecule. In addition to produce the propylene oxide as the main product, there
    are also co-products.
    Current ways that has realized industrialization include ethyl benzene Haakon method and
    isobutane Haakon method.
    Ethylbenzene Haakon mainly adopts ethylbenzene as raw material for production of ethylbenzene
    hydroperoxide by oxidation. Under the catalyst of copper naphthenate, it is subject to propylene
    epoxidation reaction, generating propylene oxide as well as alpha-phenylethanol simultaneously,
    followed by dehydration to give the styrene.
    The reaction temperature of ethylbenzene oxidation is 130-150 ℃, the pressure is 0.07-0.14 MPa,
    the selectivity of generating ethylbenzene hydroperoxide is 90%; the temperature of epoxidation
    is 50-120 ℃; The pressure is between atmospheric pressure to 0.864 MPa. For example, a mixture
    of 14% of ethylbenzene hydroperoxide, 35% of propylene, 50% of ethylbenzene and 1% of α-
    phenylethanol is added to 0.4% of naphthenic acid manganese naphthenate (nMo/nNa = 2 , Molar
    ratio) to be as the catalyst for reaction at 1.5 h at 100 ℃, resulting conversion rate of ethylbenzene
    hydroperoxide, 99% and selectivity of propylene oxide as 78%. The reaction product can be
    obtained by distillation of propylene oxide to obtain the finished product. The α-phenylethanol, in
    the dehydration reactor, is subject to dehydration at 250-280 ℃ using TiO3-Al2O3 as catalyst,
    resulting a conversion rate to styrene of 100% with a selectivity of 92%.
    The features of the method: low cost, being economic and reasonable, less waste, with co-
    production of styrene.
    Isobutane Haakon method uses isobutane as raw material, via oxidant tert-butyl hydroperoxide,
    further being reacted with propylene to generate propylene oxide and tert-butyl alcohol. The
    whole process is similar to ethylbenzene Haakon method. Manufacturing of tert-butyl
    hydroperoxide was carried out at 100~110 °C without catalyst, usually using tert-butyl
    hydroperoxide as initiator. Epoxidation of propylene was carried out under the conditions of
    reaction temperature 121 °C and pressure of 4.1 MPa to be carried out in the presence of
    molybdenum catalyst. The reaction time is 0.5 h with the yield of propylene oxide 88% (peroxides),
    selectivity of 81%.

    (𝐶𝐻3 ) 2𝐶𝐻𝐶𝐻3 + 𝑂2 → (𝐶𝐻3 ) 3𝐶𝑂𝑂𝐻 + (𝐶𝐻3 ) 3𝐶𝑂𝐻 (𝐶𝐻3 ) 3𝐶𝑂𝑂𝐻

    Mercado
    The propylene feedstock for PO has been experiencing recent production issues. US-
    based Petrologistics' 544,000 tonne/year propylene plant in Houston, Texas, US, went off line
    during the week ended March 18, following an outage on March 13. The unit went down for
    equipment repairs, and Petrologistics confirmed that the shutdown was expected to last for one
    week.US propylene inventories fell by 2.2% in the second week of March despite increased
    operating rates at US refineries, according to the Energy Information Administration (EIA).
    Refinery-sourced propylene stockpiles stood at 2.468m bbl in the week ended March 11, down
    from 2.524m bbl a week earlier.

    Global demand for PO had been growing by 4-5%/year, with growth in the US and Europe,
    estimated at 3-4%/year, but this stopped abruptly when markets collapsed in the second half of
    2008.

    PRICES

    US PO prices rose early in the year from approximately 91.75 cents/lb ($2,023/tonne,
    €1,416/tonne) to 98 cents/lb. In the week ending March 11, prices fell to 94 cents/lb, as
    assessed by ICIS.

    Meanwhile, upstream feedstock propylene prices in the US rose during the week ended March
    18, lifted by firming demand and support from a recent jump in energy prices. Refinery-grade
    propylene for March traded at 71.50-72.00 cents/lb in the week ending March 18, up from
    69.75-70.25 cents/lb a week earlier. Polymer-grade propylene traded at 76 cents/lb early in the
    week ending March 18, as assesed by ICIS.

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