Optimization of the conditions of guaiacol and glyoxylic acid condensation to vanillylmandelic acid as an intermediate product in vanillin synthesis

Selikhova, Natalia Yu.; Kurgachev, D. A.; Sidelnikov, V S; Новиков, Д. В.; Ботвин, В. В.; Полещук, О. Х.

doi:10.1088/1742-6596/1145/1/012047

Cited by 3 publications

(2 citation statements)

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“…The glyoxylic acid method was the most commonly used synthesis method in the chemical synthesis method. 14 3-Methoxy-4-hydroxymandelic acid (VMA) is an important intermediate for production of vanillin by the glyoxylic acid method. 15 , 16 At the same time, intermediates of VMA also have great applications in the pharmaceutical, cosmetic, and food processing industries.…”

Section: Introductionmentioning

confidence: 99%

“…At present, three processes have been developed for vanillin production: natural extraction, biosynthesis, and chemical synthesis. ,, Among them, the mainstream producing method is chemical synthesis, which has the advantages of mature technology, abundant raw materials, and easy availability. The glyoxylic acid method was the most commonly used synthesis method in the chemical synthesis method . 3-Methoxy-4-hydroxymandelic acid (VMA) is an important intermediate for production of vanillin by the glyoxylic acid method. , At the same time, intermediates of VMA also have great applications in the pharmaceutical, cosmetic, and food processing industries .…”

Section: Introductionmentioning

confidence: 99%

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Effect and Mechanism of Aluminum(III) for Guaiacol–Glyoxylic Acid Condensation Reaction in Vanillin Production

et al. 2020

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3-methoxy-4-hydroxymandelic acid (VMA) was the critical intermediate for the synthesis of vanillin by the glyoxylic acid method. Meanwhile, a valuable byproduct (2-hydroxy-3-methoxy-mandelic acid, o -VMA) was obtained during the reaction. Al 3+ was found to be a helpful catalyst in increasing the selectivity for VMA and o -VMA. In the presence of Al 3+ , the selectivity for VMA and o -VMA increased from 83 to 88% and from 3 to 8%, respectively, while that of the helpless byproduct 2-hydroxy-3-methoxy-1,5-mandelic acid (di-VMA) decreased from 14% to less than 4%. The kinetics based on the kinetic equation of the condensation reaction was studied by the initial concentration method. The results indicated that the involvement of Al 3+ could reduce the activation energy of the reaction on the basis of the Arrhenius equation. Combined with thermogravimetric analysis, in situ Fourier transform-infrared spectroscopy, and 1 H NMR research, Al 3+ was found to interact with guaiacol through Al–O and Al···H, which further improved the selectivity of the VMA and o -VMA and reduced the selectivity of di-VMA by adding the electronegativity of the ortho- and para-positions of hydroxyl groups of guaiacol.

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Section: Introductionmentioning

confidence: 99%