Synthesis of Triphenyl Phosphate and Benzyl Benzoate with Phase-Transfer Catalyst in a Heterogeneous Liquid-Liquid Reaction System

Asai, Satoru; Nakamura, H; Tanabe, Mitsunori; Sakamoto, Kenji

doi:10.1021/ie00031a008

Cited by 15 publications

(20 citation statements)

References 9 publications

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“…Die PTK-Veresterung wird typischerweise bei Temperaturen von 85°C durchgeführt [33 -36]. Ebenfalls wird Natriumoder Kaliumhydroxid zugegeben, um die Ionentärke anzupassen und als Base die Bildung von Benzoesäure zu verhindern [37]. Kinetische Studien der PTK-Veresterung in gerührten Laborreaktoren zeigen, dass die Reaktionsrate mit steigender Rührgeschwindigkeit und selbst bei Rühr-geschwindigkeiten über 1000 rpm exponentiell ansteigt [34,35,37].…”

Section: Introductionunclassified

Redispersion Microreactor System for Phase Transfer Catalyzed Esterification

Jovanović

Rebrov

Nijhuis

et al. 2011

Chemie Ingenieur Technik

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Redispersion Microreactor System for Phase Transfer Catalyzed EsterificationAn interdigital mixer -redispersion capillary assembly was applied to prevent the liquid-liquid bubbly flow coalescence in microreactors. The redispersion capillary consisted of 1 mm long and 0.25 mm inner-diameter constrictions placed every 0.50 m along the channel length. The system was tested on the phase transfer catalyzed esterification to produce benzyl benzoate. The application of constrictions to prevent coalescence resulted in a better reproducibility compared to a capillary without the constrictions. By controlling the total flow rate and the aqueous-to-organic ratio the bubbly flow surface-volume ratio could be increased up to 230 700 m 2 m -3. Compared to the conventional phase transfer catalyzed esterification, the continuous operation in the interdigital-redispersion capillary assembly eliminated the use of solvents and bases, removing an energy intensive step of distillation, while increasing process safety.

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Section: Introductionunclassified

Redispersion Microreactor System for Phase Transfer Catalyzed Esterification

Jovanović

Rebrov

Nijhuis

et al. 2011

Chemie Ingenieur Technik

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“…7 mol L -1 ) and the internal standard. The benzyl bromide conversion in the PTC esterification is highly dependent on the stirring speed, and therefore the bubble surface-to-volume ratio [34,35,37,38]. The coalescence of droplets in the bubbly flow results in the intermittent slug/ bubbly flow pattern, reducing the surface-to-volume ratio (Tab.…”

Section: Ptc Esterificationmentioning

confidence: 99%

“…Furthermore, the selectivity of the process improved by removing the side products such as dibenzyl ether [43]. The conventional PTC process introduced the use of solvents such as toluene, benzene, chloroform, 1,2-dichloroethane [33,37] and chlorobenzene [34], which added an energy-intensive solvent removal step via distillation. Furthermore, the PTC esterification is highly dependent on the stirring, where inhomogeneous stirring can result in yield variation.…”

Section: Process Benchmarking: Switching From Batch To Continuousmentioning

confidence: 99%

“…PTC esterification is usually performed at temperatures below 85°C [33][34][35][36], in the presence of sodium or potassium hydroxide in order to adjust the ionic strength and prevent the production of benzoic acid [37]. Kinetic studies of PTC esterification in stirred-batch reactors have shown that the reaction rate increases exponentially with increasing stirring speed, even at stirring speeds above 1000 rpm [34,35,37]. An increase in the stirring speed in batch reactors decreases the droplet size, thus increasing the specific surface-to-volume ratio [38].…”

Section: Introductionmentioning

confidence: 99%

“…Last, in PTC esterifications, solvents such as toluene, benzene, chloroform, 1,2-dichloroethane [33,37], and chlorobenzene [34] are employed to suppress the side reaction of hydrolysis [33,35] into benzyl alcohol. In this study, the reaction was performed under solvent-free conditions, in order to eliminate the expensive solvent removal step in the post-reaction workup and, with it, the environmental impact of the process.…”

Section: Introductionmentioning

confidence: 99%

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Redispersion Microreactor System for Phase Transfer‐Catalyzed Esterification

et al. 2011

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An interdigital mixer-redispersion capillary assembly was applied to prevent the liquid-liquid bubbly flow coalescence in microreactors. The redispersion capillary consisted of 1-mm-long 0.25 mm inner-diameter constrictions, placed every 0.50 m along the channel length. The system was tested on the phase transfer-catalyzed esterification to produce benzyl benzoate. The application of constrictions to prevent coalescence resulted in a better reproducibility and higher conversion compared to a capillary without constrictions. The bubbly flow generated by the interdigital mixer-redispersion capillary assembly was found to be independent of the redispersion capillary inner diameters (0.50 and 0.75 mm) while being highly dependent on the flow rates. By controlling the total flow rate and the aqueousto-organic ratio, the bubbly flow surface-to-volume ratio could be increased up to 230 700 m 2 m -3. Compared to the conventional phase transfer-catalyzed esterification, the continuous operation in the interdigital mixer-redispersion capillary assembly eliminated the use of solvents and bases, removing an energy-intensive step of distillation while increasing process safety.

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Green Synthesis of Triaryl Phosphates with POCl₃ in Water

et al. 2017

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The facile synthesis of triaryl phosphates by using POCl3 and phenols under mild conditions is a great challenge for both chemical industry and organic chemistry. Especially for the reaction of functionalized phosphorus oxychloride in water, which has long been considered impossible due to its quickly hydrolysis, the fact that makes phosphorus oxychloride serve as a type of popular starting material commonly appeared in organic solvents. Herein, a feed‐controlled substitution reaction with POCl3 in water was investigated and 97% isolated yield of triphenyl phosphate (TPP) was obtained on the kilogram scale. A broad scope of triaryl phosphates can be prepared in good yields under mild conditions without using any catalysts. The presence of appropriate amount of water could significantly promote the reaction efficiency.

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Synthesis of Triphenyl Phosphate and Benzyl Benzoate with Phase-Transfer Catalyst in a Heterogeneous Liquid-Liquid Reaction System

Cited by 15 publications

References 9 publications

Redispersion Microreactor System for Phase Transfer Catalyzed Esterification

Redispersion Microreactor System for Phase Transfer Catalyzed Esterification

Redispersion Microreactor System for Phase Transfer‐Catalyzed Esterification

Green Synthesis of Triaryl Phosphates with POCl₃ in Water

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Synthesis of Triphenyl Phosphate and Benzyl Benzoate with Phase-Transfer Catalyst in a Heterogeneous Liquid-Liquid Reaction System

Cited by 15 publications

References 9 publications

Redispersion Microreactor System for Phase Transfer Catalyzed Esterification

Redispersion Microreactor System for Phase Transfer Catalyzed Esterification

Redispersion Microreactor System for Phase Transfer‐Catalyzed Esterification

Green Synthesis of Triaryl Phosphates with POCl3 in Water

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Product

Resources

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Green Synthesis of Triaryl Phosphates with POCl₃ in Water