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    Intro AzoDye

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    jamm
    The document discusses azo dyes, which are compounds with the general structure of Ar-N=N-Ar. Many azo dyes are used as pH indicators due to their ability to function as acids or bases. The experiment aimed to synthesize the azo dye Sudan-1 through a two-step reaction involving diazotization and coupling of aniline and β-naphthol. A red/orange product was expected. The physical properties of the synthesized dye were measured.

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    Intro AzoDye

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    jamm
    101 views2 pages
    The document discusses azo dyes, which are compounds with the general structure of Ar-N=N-Ar. Many azo dyes are used as pH indicators due to their ability to function as acids or bases. The experiment aimed to synthesize the azo dye Sudan-1 through a two-step reaction involving diazotization and coupling of aniline and β-naphthol. A red/orange product was expected. The physical properties of the synthesized dye were measured.

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    The document discusses azo dyes, which are compounds with the general structure of Ar-N=N-Ar. Many azo dyes are used as pH indicators due to their ability to function as acids or bases. The experiment aimed to synthesize the azo dye Sudan-1 through a two-step reaction involving diazotization and coupling of aniline and β-naphthol. A red/orange product was expected. The physical properties of the synthesized dye were measured.

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    101 views2 pages

    Intro AzoDye

    Uploaded by

    jamm
    The document discusses azo dyes, which are compounds with the general structure of Ar-N=N-Ar. Many azo dyes are used as pH indicators due to their ability to function as acids or bases. The experiment aimed to synthesize the azo dye Sudan-1 through a two-step reaction involving diazotization and coupling of aniline and β-naphthol. A red/orange product was expected. The physical properties of the synthesized dye were measured.

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    One of the most important classes of dyes in the industry are azo dyes, compounds that

    have the general structure of Ar-N=N-Ar,’ in which Ar and Ar’ are two aromatic fragments
    (Solomons, 2011). Many of the dyes in this class are used typically as pH indicators because of
    their ability to function as weak or strong acids or bases. Common examples of azo dyes which
    are used as pH indicators are methyl red, methyl orange, and congo red. Aside from that, they
    also have numerous industrial uses such as artificial color source for textile, food and beverage,
    and clothing (Mcmurry, 2008).
    The color of these dyes are credited to the azo linkage, N=N, which brings two aromatic
    rings together. These aromatic compounds, also called chromopores, are responsible for the
    colors of the dyes (Al-Rubaie & Mhessn, 2012). The conjugation from an electron-donating group
    through the N=N bridge to an electron-withdrawing group on the other side results to an intense
    color. There are changes in color due to the extended system of delocalized p electron that allows
    the absorption of light in the visible region of the EM spectrum (Solomons, 2011)
    These compounds are a result of a two-step reaction involving a diazonium salt and
    coupling component. First, an aromatic diazonium ion from an aniline derivative is synthesized.
    In this diazotization reaction, the primary arylamine reacts with nitrous acid to produce the
    intermediate, an arenediazonium salt. The arenediazonium salt, a weak electrophile, is then
    coupled with aromatic substrates such as phenols and tertiary amines (McMurry, 2008). An Azo
    compound is the end product of this reaction.

    Fig 1. Coupling mechanism of an arenediazonium salt and an aromatic substrate (McMurry, 2008)

    The aim of this experiment was to synthesize 1-(phenylazo)-2-napthanol or Sudan-I dye


    through a two-step reaction, diazotization and coupling. A red/orange product was expected to
    be produced after executing the steps for the reactions. After successfully attaining a yield, the
    physical properties of the azo dye were noted.

    Al-Rubaie, L. A. A. R., & Mhessn, R. J. (2012). Synthesis and characterization of azo dye para red
    and new derivatives. Journal of Chemistry, 9(1), 465-470. Chicago
    McMurry, J. (2008). Organic Chemistry. (7th ed.). Brooks/Cole.
    Solomons, G. T. W., & Fryhle, C. (2011). Organic Chemistry. (10th ed.). USA: John Wiley & Sons
    Inc.
    Conclusion:

    Don’t mind notes lang.

    This experiment was conducted to synthesized 1-phenylazo-2-naphthol or Sudan-1, a


    powdered substance with a red-orange color, following the 2 reactions – diazotization and
    coupling reaction. Aniline and β-naphthol was used as starting reagents. The resulting product
    was purified using recrystallization and its melting point was determined. A cotton fabric was also
    dyed using the synthesized Sudan-1.

    Many synthetic dyes, also called diazo dyes, are coupling products of the reaction of
    arenediazonium salts and highly activated aromatic substrates such as phenols and anilines.
    Many of the coupling products are used as acid-base indicators and food coloring agents. For
    instance, methyl red, an indicator dye, is used on laboratories to indicate the acidic content of a
    chemical solution and butter yellow, which is used for margarine. Some diazo compounds are
    also used as biological staining agents and textile dyes. 2

    The diazonium salt reacts as an electrophile with an electron-rich coupling component, like a β-
    naphthol and naphthaline derivative through an electrophilic aromatic substitution mechanism.

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