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    Croton Aldehyde

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    Sakthivel Pandian
    Crotonaldehyde is a chemical compound that is usually sold as a mixture of E- and Z-isomers. It is a lachrymatory liquid that is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis and occurs naturally in some foodstuffs like soybean oils. It is produced through the aldol condensation of acetaldehyde and exhibits reactivity as a prochiral dienophile and Michael acceptor. Crotonaldehyde is also used as a precursor to chemicals like sorbic acid and trimethylhydroquinone.

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    Croton Aldehyde

    Uploaded by

    Sakthivel Pandian
    38 views2 pages
    Crotonaldehyde is a chemical compound that is usually sold as a mixture of E- and Z-isomers. It is a lachrymatory liquid that is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis and occurs naturally in some foodstuffs like soybean oils. It is produced through the aldol condensation of acetaldehyde and exhibits reactivity as a prochiral dienophile and Michael acceptor. Crotonaldehyde is also used as a precursor to chemicals like sorbic acid and trimethylhydroquinone.

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    Crotonaldehyde is a chemical compound that is usually sold as a mixture of E- and Z-isomers. It is a lachrymatory liquid that is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis and occurs naturally in some foodstuffs like soybean oils. It is produced through the aldol condensation of acetaldehyde and exhibits reactivity as a prochiral dienophile and Michael acceptor. Crotonaldehyde is also used as a precursor to chemicals like sorbic acid and trimethylhydroquinone.

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    © All Rights Reserved
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    38 views2 pages

    Croton Aldehyde

    Uploaded by

    Sakthivel Pandian
    Crotonaldehyde is a chemical compound that is usually sold as a mixture of E- and Z-isomers. It is a lachrymatory liquid that is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis and occurs naturally in some foodstuffs like soybean oils. It is produced through the aldol condensation of acetaldehyde and exhibits reactivity as a prochiral dienophile and Michael acceptor. Crotonaldehyde is also used as a precursor to chemicals like sorbic acid and trimethylhydroquinone.

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    Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO.

    The compound is
    usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position
    of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-
    isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents.
    As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It
    occurs in a variety of foodstuffs, e.g. soybean oils.[4]

    Contents

    • 1Production and reactivity


    • 2Uses
    • 3Safety
    • 4See also
    • 5References
    • 6External links

    Production and reactivity[edit]


    Crotonaldehyde is produced by the aldol condensation of acetaldehyde:
    2 CH3CHO → CH3CH=CHCHO + H2O
    Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is
    a prochiral dienophile.[5] It is a Michael acceptor. Addition of methylmagnesium
    chloride produces 3-penten-2-ol.[6]
    Polyurethane catalyst N,N,N',N'-tetramethyl-1,4-butanediamine (also known as NIAX
    TMBDA) was obtained by hydrogenating the reaction product of crotonaldehyde
    and dimethylamine.[7]

    Uses[edit]

    Crotonylidene diurea is a specialty fertilizer.[8]

    It is a precursor to fine chemicals. Sorbic acid, a food preservative, and


    trimethylhydroquinone, a precursor to the vitamin E, are prepared from crotonaldehyde.
    Other derivatives include crotonic acid and 3-methoxybutanol. It adds two equivalents of
    urea to give the pyrimidine derivative that is employed as a controlled-release fertilizer. [4]

    Safety[edit]
    Crotonaldehyde is a potent irritant even at the ppm levels. It is not very toxic, with an LD50 of
    174 mg/kg (rats, oral).[4]

    See also[edit]
    • Crotyl
    • Crotonic acid
    • Crotyl alcohol
    • Methacrolein

    References[edit]
    1. ^ Merck Index, 11th Edition, 2599
    2. ^ Jump up to:a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0157". National
    Institute for Occupational Safety and Health (NIOSH).
    3. ^ Jump up to:a b "Crotonaldehyde". Immediately Dangerous to Life and Health
    Concentrations (IDLH). National Institute for Occupational Safety and
    Health (NIOSH).
    4. ^ Jump up to:a b c R. P. Schulz, J. Blumenstein, C. Kohlpaintner (2005).
    "Crotonaldehyde and Crotonic Acid". Ullmann's Encyclopedia of Industrial Chemistry.
    Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_083.
    5. ^ Longley Jr., R. I..; Emerson, W. S.; Blardinelli, A. J. (1954). "3,4-Dihydro-2-
    methoxy-4-methyl-2H-pyran". Org. Synth. 34: 29. doi:10.15227/orgsyn.034.0029.
    6. ^ Coburn, E. R. (1947). "3-Penten-2-ol". Org. Synth. 27:
    65. doi:10.15227/orgsyn.027.0065.
    7. ^ https://jadedman.wordpress.com/2011/01/08/catalysts/
    8. ^ Dittmar, Heinrich; Drach, Manfred; Vosskamp, Ralf; Trenkel, Martin E.; Gutser,
    Reinhold; Steffens, Günter (2009). "Fertilizers, 2. Types". Ullmann's Encyclopedia of
    Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.n10_n01.

    External links[edit]
    • Hazardous Substance Fact Sheet
    • CDC - NIOSH Pocket Guide to Chemical Hazards
    Categories:
    • Alkenals
    • Lachrymatory agents
    • Hazardous materials

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