Fast Esterification of Acetic Acid with Short Chain Alcohols in Microchannel Reactor

Yao, Xueping; Yao, Jianfeng; Zhang, Lixiong; Xu, Nanping

doi:10.1007/s10562-009-0072-2

Cited by 9 publications

(3 citation statements)

References 27 publications

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“…The production of MeOAc from HOAc and MeOH has been kinetically mediated by homogeneous or heterogeneous catalysts, with more research being performed on the latter due to increased reusability, high selectivity, and less product contamination . The synthesis and kinetics via microwave, membrane, batch, and microchannel reactors have also been addressed . Most recent experimental investigations (from 2011) have reported free energy of activation for this process with values ranging from ∼7.7 to 15.1 kcal mol −1 in different reaction media/solvents at temperature up to 333 K. In addition to this parameter, some studies also provided heat of reaction (enthalpy, Δ H ) and entropy (Δ S ) of activation values within −1.0 and 0.1 kcal mol −1 for Δ H while 1.0 E −5 and 0.1 cal (mol K) −1 for the reaction entropy …”

Section: Introductionmentioning

confidence: 99%

DFT study of the acid‐catalyzed esterification reaction mechanism of methanol with carboxylic acid and its halide derivatives

Lawal

Govender

Maguire

et al. 2017

Int J of Quantum Chemistry

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Extensive experimental studies have been dedicated to the esterification mechanisms from carboxylic acids and acid halides. However, attention on the theoretical aspect of the mechanism has been scarcely addressed. Herein, the acid-catalyzed esterification mechanism of methanol with acetic acid and its halide derivatives is described using density functional theoretical method and solvation model based on density. The mechanistic investigation involved formation of cyclic prereaction and 6-membered ring transition structures, which favors the esterification process and product formation. A good comparison with experimental data from literature for the esterification reaction of acetic acid with methanol was achieved through this in silico approach. Density Functional Theory-based quantum descriptors were applied to provide a better understanding on the reactivity, selectivity, and stability of this reaction. This theoretical results provide a crucial guide to study classical acid-catalyzed reaction mechanisms and applying a reasonable theoretical model to study similar organic reactions. In addition, it can be applied to larger systems such as enzymatic mechanism. K E Y W O R D S acetic acid (HOAc), acetyl halides (XAc), Density Functional Theory (DFT), esterification reaction 1 | I N TR ODU C TI ON Esters remained important intermediates in the chemical industry due to their widespread pharmaceutical applications and biodiesel production.Dating back to the 1890s, the Fischer esterification [1] reaction has remained a crucial process through which esters are formed via dehydrative coupling of carboxylic acids (RCOOH) with alcohol (ROH) in the presence of inorganic liquid acids. [2][3][4] Among studies on kinetics and mechanism of acid-catalyzed RCOOH esterification, methyl acetate (MeOAc) formation from acetic acid (HOAc) and methanol (MeOH) using homogeneous and heterogeneous acid catalysts are abundant. [4][5][6] R€ onnback et al. [2] had earlier hypothesized the nature of the acid-catalyzed esterification of HOAc with MeOH as a stepwise model involving 7 transition structures and 3 intermediates in acidic solution. This experimental study [2] was novel and serves as a basis for subsequent investigations.The overall reaction process is presented as:The production of MeOAc from HOAc and MeOH has been kinetically mediated by homogeneous [2,[6][7][8][9][10][11] or heterogeneous catalysts, [5,6,[12][13][14][15] with more research being performed on the latter due to increased reusability, [16] high selectivity, [17] and less product contamination. [6,16,18] The synthesis and kinetics via microwave, membrane, batch, and microchannel reactors have also been addressed. [12,13,19,20] Most recent experimental investigations (from 2011) have reported free energy of activation for this process with values ranging from 7.7 to 15.1 kcal mol 21[4-6,15,21-26] in Int J Quantum Chem. 2018;118:e25497.

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Section: Introductionmentioning

confidence: 99%

DFT study of the acid‐catalyzed esterification reaction mechanism of methanol with carboxylic acid and its halide derivatives

Lawal

Govender

Maguire

et al. 2017

Int J of Quantum Chemistry

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“…Recently, there are some reports on alkali-catalyzed transesterification for biodiesel production [27][28][29][30] and esterification of acids with alcohols [31,32] in microstructured reactors. The results indicated that the reaction time could be significantly reduced.…”

Section: Introductionmentioning

confidence: 99%

Continuous production of biodiesel from high acid value oils in microstructured reactor by acid-catalyzed reactions

Sun

Yao

et al. 2010

Chemical Engineering Journal

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“…Yao et al. raised the yield of acetic acid esters to 70.1%, 74.0%, 92.2% and 97.2% in a microchannel reactor with the presence of ethanol, methanol, n‐butanol and n‐propanol, respectively, during the 14.7 min of residence . Aromatic nitration of acetyl guaiacol is highly exothermic and fast, and can be better controlled at high efficiency in the microreactor due to the acceleration of mixing and heat transfer.…”

Section: Introductionmentioning

confidence: 99%

Acetone Iodination Kinetics in Flow with Online UV Monitoring and Continuous Control

et al. 2019

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Kinetics of acetone iodide synthesis was investigated in a microchannel reaction system mainly composed of a micromixer and a tubular reactor. This system can be used as a plug flow reactor, as proved by the low variance (0.006) of residence time distribution detected by a step stimuli–response tracer. An online ultraviolet monitoring system was built to fast and reliably detect the transmittance of the flowing solution. Reaction kinetics was tested at different reactant concentrations and temperatures (35‐50 °C). Second‐order kinetics concerning acetone and HCl was identified with activation energy of 67.86 kJ/mol.

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Fast Esterification of Acetic Acid with Short Chain Alcohols in Microchannel Reactor

Cited by 9 publications

References 27 publications

DFT study of the acid‐catalyzed esterification reaction mechanism of methanol with carboxylic acid and its halide derivatives

DFT study of the acid‐catalyzed esterification reaction mechanism of methanol with carboxylic acid and its halide derivatives

Continuous production of biodiesel from high acid value oils in microstructured reactor by acid-catalyzed reactions

Acetone Iodination Kinetics in Flow with Online UV Monitoring and Continuous Control

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