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Background of Ester Manufacturing Processes

Background of Ester Manufacturing Processes. Auburn University Robert Kline 1/19/12. Overview. Chemistry Thermodynamics Flowsheet Development. Chemistry. O. C. R. O. R’. CH 3 COOH + CH 3 (CH 2 ) 3 OH  CH 3 COO(CH 2 ) 3 CH 3 + H 2 O. What are esters? Reactions

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Background of Ester Manufacturing Processes

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  1. Background of Ester Manufacturing Processes Auburn University Robert Kline 1/19/12

  2. Overview Chemistry Thermodynamics Flowsheet Development

  3. Chemistry O C R O R’ CH3COOH + CH3(CH2)3OH  CH3COO(CH2)3CH3 + H2O • What are esters? • Reactions Carboxylic Acid + Alcohol  Ester + Water

  4. Chemistry • Equilibrium Limited • Catalysts • Typically acid catalyzed • Homogeneous (sulfuric acid) • Heterogenous (amberlyst resins)

  5. Thermodynamics • Nonideal liquids • This is a chemical system rather than a hydrocarbon or petrochemical one • Significant liquid phase noidealities can exist • Azeotropes • Liquid-Liquid Behavior

  6. Thermodynamics Binary data from Horsely’s Azeotropic data, reprinted in Reactive Distillation Design and Control by Luyben and Yu

  7. Thermodynamics O O O C C C H H H O O O R R R C C R R O O H H O O Vapor Phase Association

  8. Thermodynamics • Vapor Phase Association • In the vapor phase carboxylic acids can form weakly bound dimers & trimers • This has an impact on vapor phase density, fugacity, and enthalpy

  9. Thermodynamics • What are your thermodynamic model choices? • Liquid phase nonideality capable of modeling 2 liquid phases • NTRL • UNIQUAC • UNIFAQ • Vapor phase dimerization • Hayden O’Connell • Nothnagel

  10. Flowsheet Development • Chemistry Issues • Equlibrium limited • Solid or homogenous catalyst • Thermodynamic Issues • Azeotropes • Liquid-Liquid Equilibria

  11. Flowsheet Development Recycles Reaction Separation Raw Materials Products Wastes Separation Section • How can raw materials be recovered? • Can LLE be exploited? (extractors/decanters/reflux decanters) • What sequence should the separation be done? Reaction Section • CSTR(s) • PFR • Feed ratios (which RM is easier to recover?) • Catalyst introduction & recovery

  12. Flowsheet Development Recycles Reaction & Separation Separation Raw Materials Products Wastes Separation Section • How can raw materials be recovered? • Can LLE be exploited? (extractors/decanters/reflux decanters) • What sequence should the separation be done? Rxn & Separation Section • Multistage reactor + separator • Reactor in a reboiler • Reactive distillation • Catalyst introduction & recovery

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