Feasibility Study of Reactive Distillation for the Production of Propylene Glycol Monomethyl Ether Acetate through Transesterification

Wang, Xiaoda; Wang, Qinglian; Ye, Changshen; Dong, Xiaolian; Qiu, Ting

doi:10.1021/acs.iecr.7b01462

Cited by 29 publications

(31 citation statements)

References 33 publications

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“…The esterification reaction of MPA from MP and HAC was reversible, which was generally regarded as a second‐order reaction . The kinetic model for the esterification reaction of MPA could be expressed by the following equation:

d C_{normalMPA} / d t = k_{1} C_{normalMP} C_{normalHAC} - k_{- 1} C_{normalMPA} C_{H 2 O}

Here C MPA , C MP , C HAC and C H2O represent the molarities of MPA, MP, HAC and H 2 O respectively and k 1 and k −1 are the rate constants of the forward and reverse reactions respectively:

k_{1} = A_{1} \exp (- E_{a1} / RT)

k_{- 1} = A_{2} \exp (- E_{a2} / RT)

where A 1 and A 2 are the pre‐exponential factors and E a1 and E a2 are the apparent activation energies of the forward and reverse reactions respectively.…”

Section: Resultsmentioning

confidence: 99%

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A combination of low‐temperature reactive and extractive distillation for methoxy‐2‐propyl acetate synthesis and separation process: simulations and experiments

Wang

Cai

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND Esterification of methoxy propanol (MP) and acetic acid (HAC) to methoxy‐2‐propyl acetate (MPA) is a typical reversible reaction. The yield of MPA is low owing to the limitation of chemical equilibrium. In the present study, with the goal of increasing the reaction conversion and preventing the NKC‐9 cation exchange resin catalyst from deactivation at high temperature, a process combining low‐temperature reactive and extractive distillation with cyclohexane (C6H12) as entrainer was investigated by process simulations and experiment methods. RESULTS The intrinsic kinetic parameters were obtained by catalyst activity evaluation in a batch reactor. Binary interaction parameters of thermodynamic models were determined by the measurement and fitting of vapor–liquid equilibrium data. The effects of different operating parameters on the reaction conversion and column performance were examined in detail, and a production process of MPA with an annual output of 56 000 tons was suggested. The results showed that the purity of MPA reached nearly 100% after further purification following reactive distillation, and the reaction temperature was controlled in the range 75–80 °C, which allowed long‐term operation thermal stability of the catalyst. CONCLUSION The developed low‐temperature reactive distillation method ensured a long life of the ion exchange resin catalyst, which should provide insights into further advances of MPA industrial production. © 2019 Society of Chemical Industry

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d C_{normalMPA} / d t = k_{1} C_{normalMP} C_{normalHAC} - k_{- 1} C_{normalMPA} C_{H 2 O}

Here C MPA , C MP , C HAC and C H2O represent the molarities of MPA, MP, HAC and H 2 O respectively and k 1 and k −1 are the rate constants of the forward and reverse reactions respectively:

k_{1} = A_{1} \exp (- E_{a1} / RT)

k_{- 1} = A_{2} \exp (- E_{a2} / RT)

where A 1 and A 2 are the pre‐exponential factors and E a1 and E a2 are the apparent activation energies of the forward and reverse reactions respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The esterification reaction of MPA from MP and HAC was reversible, which was generally regarded as a second-order reaction. 5,38 The kinetic model for the esterification reaction of MPA could be expressed by the following equation:…”

Section: Reaction Kinetic Modelmentioning

confidence: 99%

A combination of low‐temperature reactive and extractive distillation for methoxy‐2‐propyl acetate synthesis and separation process: simulations and experiments

Wang

Cai

et al. 2019

J of Chemical Tech & Biotech

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“…Propylene glycol monomethyl ether acetate (PGMEA) is a substantial and multipurpose solvent with a wide range of industrial applications. As one of the largest industries in the world undergoing rapid development, the semiconductor and display-material manufacturing industry requires ultra-high purity PGMEA with ultra-low acidity to satisfy the extremely tight specifications of semiconductor processing [1]. PGMEA is a crucial solvent for photoresist processing [2,3] owing to its excellent physical and chemical properties [4].…”

Section: Introductionmentioning

confidence: 99%

Pressure Swing-Based Reactive Distillation and Dividing Wall Column for Improving Manufacture of Propylene Glycol Monomethyl Ether Acetate

et al. 2021

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Propylene glycol monomethyl ether acetate (PGMEA) is a commonly used solvent in the rapidly developing semiconductor industry. Ultra-high purity PGMEA is required for this ultra-precision industry and to satisfy the current strict waste management regulations. The traditional PGMEA production process consumes considerable energy and has a high production cost. In this study, a novel heat integrated and intensified design, which applies a dividing wall column, reactive distillation, and pressure swing techniques, was proposed for improving the energy efficiency and reducing the cost of PGMEA production. Heat integration was applied to maximize the heat recovery of the process. All processes were simulated using the commercial simulator Aspen Plus V11. The economic and environmental parameters of the process alternative were assessed for a fair comparison with the conventional process. The results showed that heat integration of the optimal pressure swing-based reactive distillation and dividing wall column processes could reduce the energy requirement and TAC by 29.5%, and 20.8%, respectively, compared to that of the optimal conventional process. The improved design provides a strong basis for achieving more sustainable PGMEA production.

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“…[19][20][21][22][23][24][25] Generally, detailed reaction kinetics and thermodynamics data are necessary to choose feasible PI technologies for a certain reaction. [26][27][28][29][30] If the main reaction is accompanied by several complex side reactions, the detailed reaction routes must be also provided. That is because the side reactions might be enhanced or suppressed by using a certain process intensification method.…”

Section: Introductionmentioning

confidence: 99%

“…There are several PI technologies that could be considered, such as reactive distillation, micro‐reactors, high gravity rotating packed bed reactor, etc 19–25 . Generally, detailed reaction kinetics and thermodynamics data are necessary to choose feasible PI technologies for a certain reaction 26–30 . If the main reaction is accompanied by several complex side reactions, the detailed reaction routes must be also provided.…”

Section: Introductionmentioning

confidence: 99%

Unraveling the reaction route and kinetics of 3‐methyl‐3‐penten‐2‐one synthesis for synthetic ketone fragrances

Peng

Kiss

et al. 2020

J of Chemical Tech & Biotech

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BACKGROUND: 3-Methyl-3-penten-2-one (3M3P) is an indispensable raw material used for the synthesis of OTNE (octahydrotetramethyl acetophenone), a synthetic ketone fragrance known by commercial trade names, such as Iso E Super®, which is one of the most important ingredients in perfumes. This work is the first to unravel the reaction route and kinetics for the synthesis of 3M3P via the cross-aldol condensation of acetaldehyde with butanone, catalyzed by the heterogeneous acidic ion exchange resin (NKC-9). RESULTS: An effective method was developed to evaluate this complex reaction system: the reaction routes were determined experimentally from the product structures detected by Gas Chromatography Mass Spectrometry (GC-MS), and the significance of side reactions were evaluated by the Yoneda group contribution method. The major side reactions are the self-condensation of acetaldehyde (significant even under optimized reaction conditions) and the cross-aldol condensation of acetaldehyde with 3M3P (which could be effectively suppressed at high butanone-acetaldehyde molar ratio). The reaction kinetics was investigated at temperatures of 60-90°C, catalyst mass fraction of 5 to 15%, and molar ratio of 5-20. At optimized reaction conditions, the yield of 3M3P was up to 90.85%, which is 2.4 times higher than that for the classic homogeneous catalysts (yield <38%). CONCLUSION: Acidic ion exchange resin NKC-9 is a high-selective green catalyst for the cross-aldol condensation of acetaldehyde with butanone. Integrating experimental determination and thermomechanical analysis is an effective method to unravel the main reaction routes for a complex system.

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Feasibility Study of Reactive Distillation for the Production of Propylene Glycol Monomethyl Ether Acetate through Transesterification

Cited by 29 publications

References 33 publications

A combination of low‐temperature reactive and extractive distillation for methoxy‐2‐propyl acetate synthesis and separation process: simulations and experiments

A combination of low‐temperature reactive and extractive distillation for methoxy‐2‐propyl acetate synthesis and separation process: simulations and experiments

Pressure Swing-Based Reactive Distillation and Dividing Wall Column for Improving Manufacture of Propylene Glycol Monomethyl Ether Acetate

Unraveling the reaction route and kinetics of 3‐methyl‐3‐penten‐2‐one synthesis for synthetic ketone fragrances

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