Effect of reaction substrates on membrane-assisted transesterification reactions

Ikeda, Ayumi; Matsuura, Wakako; Abe, Chie; Hasegawa, Yasumichi

doi:10.1016/j.cep.2021.108443

Cited by 12 publications

(9 citation statements)

References 32 publications

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“…These differences in the reactiveness of alcohols can be attributed to the differences in their basicity and steric structure. The p K a values of primary alcohol was smaller than that of secondary alcohol, resulting in the protonation of secondary alcohol being less favorable …”

Section: Resultsmentioning

confidence: 97%

“…Along with esterification, amidation, and cross-coupling, transesterification is an important reaction in synthesizing pharmaceuticals and fine chemicals. − A few studies on batch-type membrane reactors for transesterification reactions have been published in recent years; for example, Ikeda et al reported an efficient ester production method based on transesterification in a batch reactor via the selective removal of the byproduct methanol using a methanol-selective membrane. , Ikeda et al proposed a kinetic model for performing transesterification in a membrane reactor and evaluated the validity of the model by comparing it with experimental results …”

Section: Introductionmentioning

confidence: 99%

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Transesterification of Methyl Acetate Using a Flow-Type Membrane Reactor with a Zeolite Membrane

Sakai

Sekine

Matsukata

2023

Ind. Eng. Chem. Res.

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Continuous-flow reactors used for manufacturing pharmaceuticals and fine chemicals have been investigated because of their advantages of high space−time yield, heat efficiency, mixing efficiency, and selectivity. In this study, we developed a flow-type membrane reactor to perform transesterification, one of the important reactions in synthesizing pharmaceuticals and fine chemicals. We observed that anion exchange ionomer (AEI) membrane exhibited high methanol selectivity because of the molecular sieving effect from the reaction system of transesterification of methyl acetate and i-butyl alcohol. Because the equilibrium level of conversion is shifted by the selective removal of methanol, the yield of i-butyl acetate using the flow membrane reactor with the AEI membrane reached 66.2%, which exceeded the 42.9% level of the equilibrium conversion without membrane. The productivity of ester improved by 54% using the proposed membrane reactor. The flow-type membrane reactor exhibited stable performance for at least 9 h. The effect of residence time in a flow reactor on the yield of ester was also studied. A substantial amount of methanol is removed through the membrane by extending the residence time. A high methanol removal fraction leads to a substantial shift in the equilibrium level, thereby improving the product yield.

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Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Transesterification of Methyl Acetate Using a Flow-Type Membrane Reactor with a Zeolite Membrane

Sakai

Sekine

Matsukata

2023

Ind. Eng. Chem. Res.

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“…FAU-type zeolite membranes were synthesized on the outside of porous α-alumina support tubes (outer diameter: 3 mm, mean pore diameter: 0.3 μm, porosity: 50%) by a secondary growth method as previously reported [ 7 , 9 ]. A synthesis solution was prepared by stirring a mixture of sodium hydroxide, sodium aluminate, sodium silicate solution, and de-ionized water for 4 h at room temperature.…”

Section: Methodsmentioning

confidence: 99%

“…Selective removal of methanol from the reaction system increases the conversion. In several transesterification reactions, conversion was shown to be increased by methanol removal using permselective FAU-type zeolite membranes in the authors’ previous reports [ 8 , 9 , 10 ]. In the transesterification of methyl hexanoate and 1-hexanol at the initial molar ratio = 1, the conversion was increased from 57% to 78% at 373 K [ 10 ].…”

Section: Introductionmentioning

confidence: 95%

“…Over the last decade, transesterification reaction with methanol permselective membrane was reported and the conversion of methyl ether increased by shifting chemical equilibrium with methanol removal [ 8 , 9 , 10 , 11 , 12 ]. In the transesterification reaction where the reaction substrate is methyl ester, the methyl ester reacts with alcohol, causing the main chains to swap to form an ester with a large molecular weight and methanol.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of FAU-type Zeolite Membrane Stability in Transesterification Reaction Conditions

et al. 2023

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The transesterification conversion of methyl ether can be enhanced by the removal of the byproduct methanol using methanol permselective faujasite (FAU-type) zeolite membranes. However, the authors previously observed that the methanol flux during the transesterification reaction was lower than the predicted flux. Therefore, this study investigated the stability of FAU-type zeolite membranes in the presence of organic components associated with the transesterification reaction of methyl hexanoate and 1-hexanol. The stability was defined in terms of changes in methanol permeance and zeolite structure. The effect of reaction components (methanol, 1-hexanol, methyl hexanoate, and hexyl hexanoate) on the FAU-type zeolite structure and the methanol permeation performance of the FAU-type zeolite membranes were evaluated to find the component causing the lower methanol flux. From these results, two esters were found to adsorb strongly on the FAU-type zeolite. The methanol flux of the FAU-type zeolite membrane was examined after vapor exposure of each of the four reaction chemicals at 373 K for 8 h. In the case of methyl hexanoate and hexyl hexanoate vapor exposure, the methanol flux was reduced by about 75% compared to the initial flux of 15 kg m−2 h−1. These results indicated methanol permeation performance was inhibited by the adsorption of esters.

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Transesterification reactions as a means to produce esters: A critical review

Devale,

Mahajan

2024

Can J Chem Eng

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Esters are important chemicals used in fine and bulk chemical industry with numerous applications: solvents, paints, varnishes, dyes, and cosmetics. Ester formation is dominated mainly by Fischer esterification and transesterification. Fischer reaction is generally used for ester production, but in certain cases, transesterification can be used with advantage. It is useful when the acid is less soluble in the alcohol or in the solvent used, thus forming two layers. Water formation creates purification problems during esterification reactions due to azeotrope formation and transesterification can be useful in such cases. Commercially, cheaply available methyl and ethyl esters can be conveniently used as raw materials for value added ester production by transesterification. Transesterification is also useful when the parent acids are highly reactive and pose difficulty in separation. Transesterifications are slow reactions and a catalyst is used: acids and bases, ion exchange resins, zeolites, and clays. Homogeneous catalysts were used in the past which are now replaced by their heterogeneous counterparts. Heterogeneous catalysts offer added advantages like reusability, lesser corrosion, and ease of separation. Transesterification can be commercially used to produce a number of esters of industrial importance like acrylics and biodiesel. This review considers all these aspects in considerable detail. A large literature set was scanned and its judicious extract is presented.

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Effect of reaction substrates on membrane-assisted transesterification reactions

Cited by 12 publications

References 32 publications

Transesterification of Methyl Acetate Using a Flow-Type Membrane Reactor with a Zeolite Membrane

Transesterification of Methyl Acetate Using a Flow-Type Membrane Reactor with a Zeolite Membrane

Evaluation of FAU-type Zeolite Membrane Stability in Transesterification Reaction Conditions

Transesterification reactions as a means to produce esters: A critical review

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