Oxidation of Vanillin to Vanillic Acid

Englis, D. T.; Manchester, Merle

doi:10.1021/ac60029a018

Cited by 17 publications

(8 citation statements)

References 7 publications

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“…Each solution is only used twice and only during the same day because of the limited stability of vanillin. 34,35 When cleaning, the cells are drained, flushed thoroughly with alcohol, rinsed with distilled water, and dried with oil-free compressed air.…”

Section: Methodsmentioning

confidence: 99%

“…When the nucleation in all the cells is completed and recorded, the temperature is raised again to dissolve the crystals in solution and to repeat the experiment or to start the cleaning. Each solution is only used twice and only during the same day because of the limited stability of vanillin. , When cleaning, the cells are drained, flushed thoroughly with alcohol, rinsed with distilled water, and dried with oil-free compressed air.…”

Section: Methodsmentioning

confidence: 99%

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Influence of Additives on Nucleation of Vanillin: Experiments and Introductory Molecular Simulations

Pino-García

Rasmuson

2004

Crystal Growth & Design

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Nucleation of vanillin (VAN) in 2-propanol/water in the presence of additives, viz., acetovanillone (AVA), ethyl vanillin (EVA), guaiacol (GUA), guaethol (GUE), 4-hydroxyacetophenone (HAP), 4-hydroxybenzaldehyde (HBA), and vanillic acid (VAC) is investigated experimentally and by molecular simulations. In the experimental work, the induction time for nucleation is measured at different temperatures and levels of supersaturation using a multicell apparatus. A large variation in the experimental data is observed, and this variation is analyzed by statistical methods. By classical nucleation theory, the induction time data are used to estimate the solid-liquid interfacial energy of vanillin for each VAN-additive system. At 1 mol %, the interfacial energy becomes lower in the presence of AVA, EVA, HAP, and VAC, while it becomes higher in the presence of the other additives. As the additive concentration increases from 1 to 10 mol %, the interfacial energy also increases. The interfacial energy ranges from 6.9 to 10.1 mJ m -2 . Molecular modeling, implemented in the program Cerius2, is used to simulate and examine the surface chemistry of the likely crystal growth faces of VAN (i.e., {0 0 1} and {1 0 0}). To evaluate the additivecrystal face interaction energy, two approaches are used: the surface adsorption method and the lattice integration method. Both experimental and molecular simulation results indicate that the additives studied are potential modifiers of the nucleation of VAN. However, a simple and clear relationship between the experimental values of interfacial energy and the calculated interaction energies for the most important crystal faces of VAN cannot be identified. The modeling does not concern the actual nucleation but rather the conditions of a growing surface and are based on several severe simplifications. Obviously, this simplistic approach does not sufficiently capture the influence of additives on the nucleation of vanillin.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Influence of Additives on Nucleation of Vanillin: Experiments and Introductory Molecular Simulations

Pino-García

Rasmuson

2004

Crystal Growth & Design

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“…Each solution is used only twice and only during the same day because of the limited stability of vanillin. 38,39 After that, the cells are cleaned, and fresh solution is used. During cleaning, the cells are drained, flushed thoroughly with alcohol, rinsed with distilled water, and dried with oilfree compressed air.…”

Section: Methodsmentioning

confidence: 99%

“…When the nucleation in all of the cells is completed and has been fully recorded, the temperature is raised again to dissolve the crystals and repeat the experiment or to facilitate cleaning of the apparatus. Each solution is used only twice and only during the same day because of the limited stability of vanillin. , After that, the cells are cleaned, and fresh solution is used. During cleaning, the cells are drained, flushed thoroughly with alcohol, rinsed with distilled water, and dried with oil-free compressed air.…”

Section: Methodsmentioning

confidence: 99%

Primary Nucleation of Vanillin Explored by a Novel Multicell Device

Pino-García

Rasmuson

2003

Ind. Eng. Chem. Res.

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A novel multicell apparatus is designed, constructed, and used to investigate crystal nucleation of vanillin in water/2-propanol solution (20 mass % of 2-propanol on a solute-free basis). The device contains 15 nucleation cells, with volumes of about 6 cm 3 each, in which the induction times for nucleation are measured simultaneously. The nucleation in the cells is continuously video-recorded and analyzed offline. The induction time for nucleation of vanillin is determined at various levels of supersaturation and temperature, and by classical nucleation theory the solid-liquid interfacial energy is estimated to 7.3 ( 0.2 mJ m -2 . A large variation in the experimental data is observed, and this variation is analyzed by statistical methods.

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“…Some reactions of oxidation or reduction could lower the yield of vanillin production. A major risk is the oxidation of vanillin present in the complex media [31,36,44,45]. The presence of bacteria, mushrooms, or yeasts foreign to the biotechnological process can lead to the formation of undesirable products such as guaiacol [33], vanillyl alcohol [28,30,31], and other aldehydes [16].…”

Section: Introductionmentioning

confidence: 99%

Electroanalysis may be used in the Vanillin Biotechnological Production

Giraud

Mirabel²,

Comtat

2013

Appl Biochem Biotechnol

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This study shows that electroanalysis may be used in vanillin biotechnological production. As a matter of fact, vanillin and some molecules implicated in the process like eugenol, ferulic acid, and vanillic acid may be oxidized on electrodes made of different materials (gold, platinum, glassy carbon). By a judicious choice of the electrochemical method and the experimental conditions the current intensity is directly proportional to the molecule concentrations in a range suitable for the biotechnological process. So, it is possible to imagine some analytical strategies to control some steps in the vanillin biotechnological production: by sampling in the batch reactor during the process, it is possible to determine out of line the concentration of vanillin, eugenol, ferulic acid, and vanillic acid with a gold rotating disk electrode, and low concentration of vanillin with addition of hydrazine at an amalgamated electrode. Two other possibilities consist in the introduction of electrodes directly in the batch during the process; the first one with a gold rotating disk electrode using linear sweep voltammetry and the second one requires three gold rotating disk electrodes held at different potentials for chronoamperometry. The last proposal is the use of ultramicroelectrodes in the case when stirring is not possible.

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Oxidation of Vanillin to Vanillic Acid

Cited by 17 publications

References 7 publications

Influence of Additives on Nucleation of Vanillin: Experiments and Introductory Molecular Simulations

Influence of Additives on Nucleation of Vanillin: Experiments and Introductory Molecular Simulations

Primary Nucleation of Vanillin Explored by a Novel Multicell Device

Electroanalysis may be used in the Vanillin Biotechnological Production

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