Synthesis of hippuric acid with inverse phase transfer catalyst in a heterogeneous liquid-liquid reaction system

Asai, Satoru; Nakamura, H; Okada, W.; Yamada, Mitsuharu

doi:10.1016/0009-2509(94)00493-b

Cited by 10 publications

(3 citation statements)

References 6 publications

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“…The Starks ion-exchange mechanism and the Makosza interfacial-reaction mechanism are among the two well-known models for ion initiation reactions in liquid−liquid two-phase systems. However, little has been known about the molecular details of the mechanism of PTC, mainly owing to the complex interplay of mass transfer, adsorption, partitioning, and chemical reactions, all of which depend on the details of experimental conditions. − …”

Section: Introductionmentioning

confidence: 99%

“…However, little has been known about the molecular details of the mechanism of PTC, mainly owing to the complex interplay of mass transfer, adsorption, partitioning, and chemical reactions, all of which depend on the details of experimental conditions. [7][8][9][10][11][12][13][14][15] From an electrochemical viewpoint, the role of phase-transfer catalysts is not necessarily to form ion pairs with hydrophilic reactants; the distribution potential between the two phases spontaneously formed by partitioning of ionic phase-transfer catalysts can act as the driving force for transferring charged reactants to the organic phase. 16,17 Such an electrochemical understanding of the mechanism of PTC can further be extended by applying the potential difference between the two phases to induce two-phase chemical reactions; chemical reactions can take place in the organic phase without phase-transfer catalysts if reactive cations or anions in the aqueous phase (W) are transferred to the organic phase in response to the applied potential.…”

Section: Introductionmentioning

confidence: 99%

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Two-Phase Azo-Coupling Reactions Driven by Phase-Boundary Potential Across the Liquid|Liquid Interface

2000

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Phase-boundary-potential-driven azo coupling has been demonstrated for the reaction between hydrophilic arenediazonium ions and lipophilic coupling components in 1,2-dichloroethane (DCE)|water (W) two-phase systems. Instead of using phase-transfer catalysts, hydrophilic arenediazonium ions are driven into the DCE phase by externally controlling the potential drop across the polarized DCE|W interface. The diffusion-controlled transfer of arenediazonium ions across the interface is followed by azo-coupling reactions with coupling components in the DCE phase. The rate of the azo coupling in DCE has been accurately determined by using potential-step chronoamperometry for the transfer for four arenediazonium ions having different lipophilicity in the presence of one of four aromatic coupling components in DCE. No appreciable contribution of the adsorbed reactants to the overall azo-coupling process is detected. An electrochemical approach using liquid|liquid two-phase systems is advantageous in determining the rate of two-phase chemical reactions and is promising for elucidating the mechanism of phase-transfer catalysis.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Two-Phase Azo-Coupling Reactions Driven by Phase-Boundary Potential Across the Liquid|Liquid Interface

2000

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“…However, it has been suggested as an essential amino acid for maximum performance of growing chicks ( Corzo et al, 2004 ; Waguespack, 2005 ; Waldroup et al, 2005 ; Dean et al, 2006 ). In addition, Gly has the following metabolic functions: synthesis of proteins, purines, porphyrin moiety of heme groups ( Furuya, 2008 ), glutathione (te Braake et al, 2008 ), creatine ( Wyss and Kaddurah-Daouk, 2000 ), and hippuric acid ( Asai et al, 1995 ). Gly has also been reported as indispensable for synthesis of uric acid for excretion of any excess nitrogen ( Corzo et al, 2004 ).…”

Section: Introductionmentioning

confidence: 99%

Effects of Dietary Levels of Glycine, Threonine and Protein on Threonine Efficiency and Threonine Dehydrogenase Activity in Hepatic Mitochondria of Chicks

Lee

Cho²,

Lee³

et al. 2014

Asian Australas. J. Anim. Sci

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This study was carried out to evaluate the relationship between threonine (Thr) efficiency and Thr dehydrogenase (TDG) activity as an indicator of Thr oxidation on chicks fed with levels of diets (CP [17.5% and 21.5%] and Thr [3.8 and 4.7 g/100 g CP]; glycine [Gly][0.64% and 0.98%] and true digestible Thr [dThr] [0.45% and 0.60%]). Calculation of the Thr efficiency was based on N-balance data and an exponential N-utilization model, and TDG activity was determined as accumulation of aminoacetone and Gly during incubation of hepatic mitochondria. This study found that in the liver of chicks who received a diet containing up to 0.79% Thr (4.7 g Thr/100 g of CP) in the 17.5% CP diet, no significant (p>0.05) effect on TDG activity was observed. However, significantly (p = 0.014) increased TDG activity was observed with a diet containing 21.5% CP (4.7 g Thr/100 g of CP) and the efficiency of Thr utilization showed a significant (p = 0.001) decrease, indicating the end of the Thr limiting range. No significant (p>0.05) effect on the total TDG activity and accumulation of Gly was observed with addition of Gly to a diet containing 0.45% dThr. In addition, addition of Gly to a diet containing 0.60% dThr also did not result in a change in accumulation of Gly. Due to an increase in accumulation of aminoacetone, an elevated effect on total TDG activity was also observed. No significant (p>0.05) reduction in the efficiency of Thr utilization was observed after addition of Gly at the level of 0.45% dThr. However, significantly (p<0.001) reduced efficiency of Thr utilization was observed after addition of Gly at the level of 0.60% dThr. Collectively, we found that TDG was stimulated not only by addition of Thr and protein to the diet, but also by addition of Gly, and efficiency of Thr utilization was favorably affected by addition of Gly at the level near to the optimal Thr concentration. In addition, no metabolic requirement of Gly through the TDG pathway was observed with almost the same accumulation of Gly and a slight increase in TDG activity by addition of Gly. Thus, our findings suggest that determination of TDG activity and parameter of efficiency of Thr utilization may be useful for evaluation of dietary Thr level.

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Recent Advances in Phase‐transfer Catalysis

Sasson

Rothenberg

2002

Handbook of Green Chemistry and Technology

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Synthesis of hippuric acid with inverse phase transfer catalyst in a heterogeneous liquid-liquid reaction system

Cited by 10 publications

References 6 publications

Two-Phase Azo-Coupling Reactions Driven by Phase-Boundary Potential Across the Liquid|Liquid Interface

Two-Phase Azo-Coupling Reactions Driven by Phase-Boundary Potential Across the Liquid|Liquid Interface

Effects of Dietary Levels of Glycine, Threonine and Protein on Threonine Efficiency and Threonine Dehydrogenase Activity in Hepatic Mitochondria of Chicks

Recent Advances in Phase‐transfer Catalysis

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