Formation and recovery of itaconic acid from aqueous solutions of citraconic acid and succinic acid

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

    Research output: Contribution to journalArticle

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    Abstract

    The formation and recovery of itaconic acid (IA) from mixed aqueous solutions of citraconic acid (CA) and succinic acid (SA) has been developed as part of an overall process to produce itaconic acid via condensation of succinates with formaldehyde. The formation and recovery described here involves four steps: (1) removal of SA via crystallization, (2) isomerization of CA to IA at elevated temperature, (3) recovery of IA via crystallization, and (4) conversion of reaction byproducts back to CA. As part of the overall process, these steps facilitate recycling of unreacted species and reuse of byproducts, thus giving high overall yields. Itaconic and succinic acids are readily crystallized because of their low solubility relative to CA; lab-scale crystallization experiments gave high purity (99.8 wt % for SA; 99.4% for IA) crystalline solids after washing. Isomerization gave a maximum IA selectivity of 87% at 170°C after 3 h reaction. The primary byproduct of isomerization, citramalic acid (CMA), and IA in the residual crystallization liquor are converted exclusively back to CA over γ-alumina at 270°C.

    Original languageEnglish (US)
    Pages (from-to)2069-2073
    Number of pages5
    JournalIndustrial and Engineering Chemistry Research
    Volume41
    Issue number9
    StatePublished - May 1 2002

    Profile

    Succinic Acid
    Acids
    acid
    Muscle Contraction
    Mandibular Condyle
    Byproducts
    Crystallization
    Bacteriophage Typing
    Recovery
    crystallization
    Succinates
    Isomerization
    Common Bile Duct Diseases
    Acetanilides
    Ergothioneine
    Dye Dilution Technique
    Butylene Glycols
    Exfoliative Dermatitis
    Leukopenia
    Recycling

    ASJC Scopus subject areas

    • Polymers and Plastics
    • Environmental Science(all)
    • Chemical Engineering (miscellaneous)

    Cite this

    Formation and recovery of itaconic acid from aqueous solutions of citraconic acid and succinic acid. / Hogle, Bryan P.; Shekhawat, Dushyant; Nagarajan, Kirthivasan; Jackson, James E.; Miller, Dennis J.

    In: Industrial and Engineering Chemistry Research, Vol. 41, No. 9, 01.05.2002, p. 2069-2073.

    Research output: Contribution to journalArticle

    Hogle, Bryan P.; Shekhawat, Dushyant; Nagarajan, Kirthivasan; Jackson, James E.; Miller, Dennis J. / Formation and recovery of itaconic acid from aqueous solutions of citraconic acid and succinic acid.

    In: Industrial and Engineering Chemistry Research, Vol. 41, No. 9, 01.05.2002, p. 2069-2073.

    Research output: Contribution to journalArticle

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    abstract = "The formation and recovery of itaconic acid (IA) from mixed aqueous solutions of citraconic acid (CA) and succinic acid (SA) has been developed as part of an overall process to produce itaconic acid via condensation of succinates with formaldehyde. The formation and recovery described here involves four steps: (1) removal of SA via crystallization, (2) isomerization of CA to IA at elevated temperature, (3) recovery of IA via crystallization, and (4) conversion of reaction byproducts back to CA. As part of the overall process, these steps facilitate recycling of unreacted species and reuse of byproducts, thus giving high overall yields. Itaconic and succinic acids are readily crystallized because of their low solubility relative to CA; lab-scale crystallization experiments gave high purity (99.8 wt % for SA; 99.4% for IA) crystalline solids after washing. Isomerization gave a maximum IA selectivity of 87% at 170°C after 3 h reaction. The primary byproduct of isomerization, citramalic acid (CMA), and IA in the residual crystallization liquor are converted exclusively back to CA over γ-alumina at 270°C.",
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    AU - Hogle,Bryan P.

    AU - Shekhawat,Dushyant

    AU - Nagarajan,Kirthivasan

    AU - Jackson,James E.

    AU - Miller,Dennis J.

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    AB - The formation and recovery of itaconic acid (IA) from mixed aqueous solutions of citraconic acid (CA) and succinic acid (SA) has been developed as part of an overall process to produce itaconic acid via condensation of succinates with formaldehyde. The formation and recovery described here involves four steps: (1) removal of SA via crystallization, (2) isomerization of CA to IA at elevated temperature, (3) recovery of IA via crystallization, and (4) conversion of reaction byproducts back to CA. As part of the overall process, these steps facilitate recycling of unreacted species and reuse of byproducts, thus giving high overall yields. Itaconic and succinic acids are readily crystallized because of their low solubility relative to CA; lab-scale crystallization experiments gave high purity (99.8 wt % for SA; 99.4% for IA) crystalline solids after washing. Isomerization gave a maximum IA selectivity of 87% at 170°C after 3 h reaction. The primary byproduct of isomerization, citramalic acid (CMA), and IA in the residual crystallization liquor are converted exclusively back to CA over γ-alumina at 270°C.

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