Abstract
A new method of synthesis 2,2-dimethylolpropionic acid from 2,2-dimethylolpropionaldehyde was put forward. The electrochemical oxidation behavior of 2,2-dimethylolpropionaldehyde has been investigated on a Ti/SnO2 + Sb2O4/PbO2 electrode by cyclic voltammetry (CV) and stable polarization curves in sulfuric acid. The results showed that it was an irreversible reaction controlled by diffusion. The formation mechanism of 2,2-dimethylolpropionic acid in the sulfuric acid was then proposed and the transfer coefficients of the reaction were calculated. It was concluded that RCHO+ỌHads→RCHOỌHads was the rate-determining step in the electrolysis process. The rate of this step obtained from the assumed process agrees well with experiment.
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Luciani, A., Plummer, J.G., Nguyen, T., Garamszegi, L., Månson, J.-A.E.: Rheological and physical properties of aliphatic hyperbranched polyesters [J]. J. Polym. Sci. Part B: Polym. Phys. 42, 1218–1225 (2004)
Žagar, E., Žigon, M.: Characterization of a commercial hyperbranched aliphatic polyester based on 2,2-bis(methylol)propionic acid. Macromol. 35, 9913–9925 (2002)
Komber, H., Ziemer, A., Voit, B.: Etherification as side reaction in the hyperbranched polycondensation of 2,2-bis(hydroxymethyl)propionic acid. Macromol. 35, 3514–3519 (2002)
Cai, J., Chen, J., Sun, M.: Preparation of 2,2-dimethylolpropionic acid. Chem. Ind. Eng. Prog. 25, 1198–1200 (2006)
Robert, J.R.: Method of making polymethylalkanoic acids. US Patent 3312736 (1967)
Jin, S., Ye, S.: Oxygen evolution on titanium anodes coated with conductive metallic oxides: kinetics and mechanism in alkaline solution. Electrochim. Acta 41, 827–834 (1996)
Devilliers, D., Dinh Thi, M.T., Mahé, E., Dauriac, V., Lequeux, N.: Electroanalytical investigations on electrodeposited lead dioxide. J. Electroanal. Chem. 573, 227–239 (2004)
Velichenko, A.B., Amadelli, R., Enedetti, A.B., Girenko, D.V., Kovalyov, S.V., Danilov, F.I.: Electrosynthesis and physicochemical properties of PbO2 films. J. Electrochem. Soc. 149, C445 (2002)
Yu, J., Cao, X., Zhang, H.: Electrooxidation of hydroxypivalaldehyde in an undivided cell. Chem. Res. Chin. Univ. 22, 626–630 (2006)
Monahov, B., Pavlov, D., Kirchev, A., Vasilev, S.: Influence of pH of the H2SO4 solution on the phase composition of the PbO2 active mass and of the PbO2 anodic layer formed during cycling of lead electrodes. J. Power Sources 113, 281–292 (2003)
Koivusalmi, E., Tulisalo, J.: Determination of highly polar compounds in reaction mixtures of 2,2-bis(hydroxymethyl)propionic acid and 3-hydroxy-2,2-bis(hydroxymethyl)propionic acid by HPLC. J. Liq. Chromatogr. Relat. Technol. 24, 187–200 (2001)
Hsiao, M.W., Adzic, R.R., Yeager, E.B.: The effects of adsorbed anions on the oxidation of D-glucose on gold single crystal electrodes. J. Electrochem. Soc. 143, 759–767 (1996)
Lamy, C., Beden, B., Leger, J.M.: Comment on A. Heinzel et al.’s paper on the electrooxidation of methanol and formaldehyde at a platinum electrodes: a SEESR study of radical intermediates. Electrochim. Acta 35, 679–680 (1990)
Matsui, H., Kunugi, A.: The kinetics of oxidation of formaldehyde at a platinum electrode in an acid solution. Bull. Chem. Soc. Jpn. 63, 507–510 (1990)
Wu, H.: Applied Electrochemistry Foundation. pp. 80–86. Xiamen University Press, Xiamen (2006)
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Liang, Z., Sun, H. Kinetics of the Electrocatalytic Oxidation of 2,2-Dimethylolpropionaldehyde. J Solution Chem 38, 47–56 (2009). https://doi.org/10.1007/s10953-008-9347-2
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DOI: https://doi.org/10.1007/s10953-008-9347-2