Formation of citraconic anhydride via condensation of dialkyl succinates and formaldehyde

Dushyant Shekhawat, Kirthivasan Nagarajan, James E. Jackson, Dennis J. Miller

    Research output: Research - peer-reviewArticle

    • 8 Citations

    Abstract

    The formation of citraconic anhydride (CAN) from the condensation of succinic acid and its derivatives with formaldehyde over oxide catalysts is described. Alumina and aluminum phosphate are active catalysts that give selectivity to citraconic anhydride as high as 75% in an integral fixed bed reactor. Weakly acidic sites on the catalyst surface, particularly Lewis acid sites, are responsible for activating the desired reaction pathway. Strongly acidic sites lead to cracking and coking, while basic sites facilitate the Cannizzaro reaction of formaldehyde to carbon dioxide and methanol. Catalyst deactivation via coking occurs over the course of reaction, but activity is easily restored by regeneration in air at elevated temperatures. The reaction system under investigation is part of an overall process to produce itaconic acid from renewable resource-based succinic acid.

    LanguageEnglish (US)
    Pages261-273
    Number of pages13
    JournalApplied Catalysis A: General
    Volume223
    Issue number1-2
    DOIs
    StatePublished - 2002

    Profile

    Succinates
    Formaldehyde
    Condensation
    Catalysts
    citraconic anhydride
    Acids
    Coking
    Succinic Acid
    Lewis Acids
    Catalyst deactivation
    Catalyst selectivity
    Aluminum Oxide
    Carbon Dioxide
    Oxides
    Methanol
    Derivatives
    Air
    Temperature
    aluminum phosphate
    itaconic acid

    Keywords

    • Alumina
    • Aluminum phosphate
    • Citraconate
    • Citraconic anhydride
    • Formaldehyde
    • Itaconate
    • Itaconic acid
    • Stobbe condensation
    • Succinic acid

    ASJC Scopus subject areas

    • Catalysis
    • Process Chemistry and Technology

    Cite this

    Formation of citraconic anhydride via condensation of dialkyl succinates and formaldehyde. / Shekhawat, Dushyant; Nagarajan, Kirthivasan; Jackson, James E.; Miller, Dennis J.

    In: Applied Catalysis A: General, Vol. 223, No. 1-2, 2002, p. 261-273.

    Research output: Research - peer-reviewArticle

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    abstract = "The formation of citraconic anhydride (CAN) from the condensation of succinic acid and its derivatives with formaldehyde over oxide catalysts is described. Alumina and aluminum phosphate are active catalysts that give selectivity to citraconic anhydride as high as 75% in an integral fixed bed reactor. Weakly acidic sites on the catalyst surface, particularly Lewis acid sites, are responsible for activating the desired reaction pathway. Strongly acidic sites lead to cracking and coking, while basic sites facilitate the Cannizzaro reaction of formaldehyde to carbon dioxide and methanol. Catalyst deactivation via coking occurs over the course of reaction, but activity is easily restored by regeneration in air at elevated temperatures. The reaction system under investigation is part of an overall process to produce itaconic acid from renewable resource-based succinic acid.",
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