Mechanism and kinetics of esterification of adipic acid and ethylene glycol by tetrabutyl titanate catalyst

Chen, Liwei; Xu, Jumei; Xue, Weilan; Zeng, Zuoxiang

doi:10.1007/s11814-017-0276-x

Cited by 10 publications

(11 citation statements)

References 16 publications

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“…k 1 and k 2 are the kinetic constants in Equation , M cat is the catalyst loading of per unit mass of all reactants, and x A , x B , x C , and x D represent a mole fraction of lauric acid, ethanol, ethyl laurate, and water, respectively. The Simpson's numerical integration was used to calculate the reaction rate . The kinetic parameters were estimated by minimizing the sum of residual squares (SRS), which can be expressed as follows:

0true SRS = \sum_{samples} {false(r_{\exp} - r_{cal} false)}^{2}

where r exp and r cal denote the reaction rate obtained from experiments and calculated data.…”

Section: Resultsmentioning

confidence: 99%

Kinetic study on the reaction of lauric acid with ethanol catalyzed by deep eutectic solvent based on cetyl trimethyl ammonium bromide

Chen

Xue

et al. 2019

Int J of Chemical Kinetics

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In this work, a novel type of deep eutectic solvents (DES: CTAB–DES) based on cetyl trimethyl ammonium bromide (CTAB) was successfully synthesized by mixing CTAB with p‐toluenesulfonic acid monohydrate and applied as catalysts for the esterification reaction of ethanol and lauric acid. The kinetics of the reaction of ethanol and lauric acid catalyzed by CTAB–DES was investigated in the temperature range of 328.15–348.15 K. The influence of different parameters including agitation speed, temperature, catalyst loading, and the lauric acid to ethanol molar ratio on the conversion of lauric acid was discussed. The kinetic experimental data obtained were correlated by the pseudo‐homogeneous model, and the results show that it can predict the reaction process well. Moreover, CTAB–DES can be reused six times without any significant decrease in catalytic activity.

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0true SRS = \sum_{samples} {false(r_{\exp} - r_{cal} false)}^{2}

where r exp and r cal denote the reaction rate obtained from experiments and calculated data.…”

Section: Resultsmentioning

confidence: 99%

Kinetic study on the reaction of lauric acid with ethanol catalyzed by deep eutectic solvent based on cetyl trimethyl ammonium bromide

Chen

Xue

et al. 2019

Int J of Chemical Kinetics

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“…Therefore, the kinetic equation for this reaction system was established based on the PH model and was modified as follows:

\begin{array}{c} center & r = W_{c a t} (k_{1} a_{a c i d} a_{E t O H} - k_{2} a_{e s t e r} a_{H_{2} O}) \end{array} \begin{array}{c} center & = W_{c a t} k_{1} (a_{a c i d} a_{E t O H} - \frac{1}{K_{e}} a_{e s t e r} a_{H_{2} O}) \end{array}

where

K_{e} = k_{1} / k_{2}

k_{1}

, and

k_{2}

are the kinetic constants in Equation . The Simpson's numerical integration was used to calculate the reaction rate . The kinetic parameters were estimated by minimizing the sum of residual squares (SRS), which can be expressed as follows:

SRS = \sum_{s a m p l e s} {false(y_{e x p} - y_{c a l} false)}^{2}

where

y_{e x p}

true(y_{c a l} true)

denotes the conversion of lauric acid obtained from experiments (calculated).…”

Section: Resultsmentioning

confidence: 99%

Kinetics of the reaction of ethanol and lauric acid catalyzed by deep eutectic solvent based on benzyltrimethylammonium chloride

Xue

Zeng

et al. 2018

Can J Chem Eng

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In this work, three types of deep eutectic solvents (DESs: BAC-PTSA, BAC-2PTSA, and BAC-3PTSA) based on benzyltrimethylammonium chloride (BAC) were successfully synthesized by mixing benzyltrimethylammonium chloride with p-toluenesulphonic acid monohydrate (PTSA) and used as catalysts for the esterification reaction of ethanol and lauric acid. The kinetics of the reaction of ethanol and lauric acid in the presence of DESs as catalysts was investigated systemically in the temperature range of 333.15-353.15 K. The influences of different parameters including type of DESs, reaction temperature, catalyst loading, and initial reactant molar ratio on the conversion of lauric acid were discussed. The kinetic experimental data obtained were successfully correlated by the pseudohomogeneous (PH) model based on the activities. Moreover, BAC-3PTSA is easily synthesized and reused six times without any significant decrease in catalytic activity.

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“…However, slow reaction rates and competing side reactions associated with the esterification pathway − create a more complex reaction network. Challenges associated with the esterification process have spurred the investigation of its reaction kinetics , and consolidation of reaction steps. − Reaction mechanisms of diol-diacid dehydration esterification have been theorized, ,, but none has been assessed with molecular modeling to the best of our knowledge. This work aims to investigate the assumed catalytic esterification mechanism to provide a better understanding for future endeavors.…”

Section: Introductionmentioning

confidence: 99%

DFT Analysis of Organotin Catalytic Mechanisms in Dehydration Esterification Reactions for Terephthalic Acid and 2,2,4,4-Tetramethyl-1,3-cyclobutanediol

et al. 2021

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Polyesters synthesized from 2,2,4,4-tetramethyl-1,3cyclobutanediol (TMCD) and terephthalic acid (TPA) are improved alternatives to toxic polycarbonates based on bisphenol A. In this work, we use ωB97X-D/LANL2DZdp calculations, in the presence of a benzaldehyde polarizable continuum model solvent, to show that esterification of TMCD and TPA will reduce and subsequently dehydrate a dimethyl tin oxide catalyst, becoming ligands on the now four-coordinate complex. This reaction then proceeds most plausibly by an intramolecular acyltransfer mechanism from the tin complex, aided by a coordinated proton donor such as hydronium. These findings are a key first step in understanding polyester synthesis and avoiding undesirable side reactions during production.

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Mechanism and kinetics of esterification of adipic acid and ethylene glycol by tetrabutyl titanate catalyst

Cited by 10 publications

References 16 publications

Kinetic study on the reaction of lauric acid with ethanol catalyzed by deep eutectic solvent based on cetyl trimethyl ammonium bromide

Kinetic study on the reaction of lauric acid with ethanol catalyzed by deep eutectic solvent based on cetyl trimethyl ammonium bromide

Kinetics of the reaction of ethanol and lauric acid catalyzed by deep eutectic solvent based on benzyltrimethylammonium chloride

DFT Analysis of Organotin Catalytic Mechanisms in Dehydration Esterification Reactions for Terephthalic Acid and 2,2,4,4-Tetramethyl-1,3-cyclobutanediol

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