Kinetics of mixed ethanol/n-butanol esterification of butyric acid with amberlyst 70 and p-toluene sulfonic acid

Arati Santhanakrishnan, Abigail Shannon, Lars Peereboom, Carl T. Lira, Dennis J. Miller

    Research output: Contribution to journalArticle

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    Abstract

    Esterification of butyric acid with ethanol, n-butanol, and ethanol/n-butanol mixtures was studied using Amberlyst 70 cation-exchange resin and homogeneous p-toluene sulfonic acid as catalysts. The kinetics of individual alcohol esterification were first examined in batch reactions at different temperatures and catalyst loadings, and then esterification in ethanol/n-butanol mixtures of varying concentration ratios was characterized. Both nonideal solution and ideal solution kinetic models were developed. These models accurately predict the esterification of butyric acid by the individual alcohols; a simple additive combination of the individual alcohol esterification kinetics properly describes mixed alcohol esterification, indicating that the alcohols do not compete with each other or inhibit esterification when present together. When solution density is included in the kinetic rate expression to account for the actual concentration of -OH groups in ethanol and n-butanol, butyric acid esterification kinetics with the two alcohols are described by a common rate constant. This rate constant also predicts butyric acid esterification kinetics with other alcohol combinations, suggesting a generalized esterification rate constant for simple alcohol esterification of butyric acid over Amberlyst 70 catalyst. These results provide significant predictive capabilities for simulating processes such as reactive distillation processes for mixed alcohol esterification.

    Original languageEnglish (US)
    Pages (from-to)1845-1853
    Number of pages9
    JournalIndustrial and Engineering Chemistry Research
    Volume52
    Issue number5
    DOIs
    StatePublished - Feb 6 2013

    Profile

    1-Butanol
    Butyric Acid
    Sulfonic Acids
    Esterification
    Toluene
    Ethanol
    Chronic Hepatitis
    Alcohols
    Kinetics
    Butyric acid
    Butenes
    Rate constants
    Catalysts
    Afferent Loop Syndrome
    Acids
    Anthralin
    Agglutination Tests
    Cation Exchange Resins
    Distillation
    Temperature

    ASJC Scopus subject areas

    • Chemical Engineering(all)
    • Chemistry(all)
    • Industrial and Manufacturing Engineering

    Cite this

    Kinetics of mixed ethanol/n-butanol esterification of butyric acid with amberlyst 70 and p-toluene sulfonic acid. / Santhanakrishnan, Arati; Shannon, Abigail; Peereboom, Lars; Lira, Carl T.; Miller, Dennis J.

    In: Industrial and Engineering Chemistry Research, Vol. 52, No. 5, 06.02.2013, p. 1845-1853.

    Research output: Contribution to journalArticle

    Santhanakrishnan, Arati; Shannon, Abigail; Peereboom, Lars; Lira, Carl T.; Miller, Dennis J. / Kinetics of mixed ethanol/n-butanol esterification of butyric acid with amberlyst 70 and p-toluene sulfonic acid.

    In: Industrial and Engineering Chemistry Research, Vol. 52, No. 5, 06.02.2013, p. 1845-1853.

    Research output: Contribution to journalArticle

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    abstract = "Esterification of butyric acid with ethanol, n-butanol, and ethanol/n-butanol mixtures was studied using Amberlyst 70 cation-exchange resin and homogeneous p-toluene sulfonic acid as catalysts. The kinetics of individual alcohol esterification were first examined in batch reactions at different temperatures and catalyst loadings, and then esterification in ethanol/n-butanol mixtures of varying concentration ratios was characterized. Both nonideal solution and ideal solution kinetic models were developed. These models accurately predict the esterification of butyric acid by the individual alcohols; a simple additive combination of the individual alcohol esterification kinetics properly describes mixed alcohol esterification, indicating that the alcohols do not compete with each other or inhibit esterification when present together. When solution density is included in the kinetic rate expression to account for the actual concentration of -OH groups in ethanol and n-butanol, butyric acid esterification kinetics with the two alcohols are described by a common rate constant. This rate constant also predicts butyric acid esterification kinetics with other alcohol combinations, suggesting a generalized esterification rate constant for simple alcohol esterification of butyric acid over Amberlyst 70 catalyst. These results provide significant predictive capabilities for simulating processes such as reactive distillation processes for mixed alcohol esterification.",
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