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Catalysis of Nontronite in Phenols and Glycine Transformations

Published online by Cambridge University Press:  02 April 2024

M. C. Wang
M. C. Wang*
Affiliation:
Department of Soil Science, National Chung Hsing University, Taichung, Taiwan 40227, Republic of China
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Abstract

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The catalytic power of Ca-nontronite (0.2–2 μm) for the polycondensation of phenols and glycine and the associated reactions that involve the ring cleavage of phenols and the decarboxylation and deamination of glycine was studied in systems free of microbial activity. At the end of a 90-hr reaction period, the amount of CO2 released from the Ca-nontronite-glycine-pyrogallol, Ca-nontronite-glycine-eatechol, and Ca-nontronite-glycine-hydroquinone systems were 5.1, 8.7, and 11.6 times higher, respectively, than those from the respective nontronite-free systems, showing the catalytic role of Ca-nontronite in the ring cleavage of phenols and the decarboxylation of glycine. The release of CO2 and NH3 from the Ca-nontronite-glycine system revealed that Ca-nontronite can catalyze decarboxylation and deamination of glycine. The ability of Ca-nontronite to catalyze the deamination of glycine was substantially enhanced by the presence of a phenol. The visible absorbances at both 472 and 664 nm of the supernatants, the total yields of N-containing humic polymers, and the fractions of glycine converted to nitrogenous polymers indicated that polycondensation of glycine and phenol was greatly catalyzed by Ca-nontronite. The total N-containing humic polymers formed in the systems decreased in the order: Ca-nontronite-glycine-pyrogallol > Ca-nontronite-glycine-cateehol > Ca-nontronite-glycine-hydroquinone > glycine-pyrogallol > glycine-hydroquinone > glycine-catechol. The infrared and electron spin resonance spectra of humic acid (HA) and fulvic acid (FA) formed in the supernatants of the reaction systems were quite similar to those of soil HA and FA. The catalytic power of Ca-nontronite in affecting the ring cleavage of phenols, deamination and decarboxylation of amino acids, and formation of humic substances derived from phenols with amino acids in soils and the related environments thus merits attention.

Keywords

CatalysisDeaminationDecarboxylationGlycineNontronitePhenolPolycondensation
Type
Research Article
Information
Clays and Clay Minerals , Volume 39 , Issue 2 , April 1991 , pp. 202 - 210
Copyright
Copyright © 1991, The Clay Minerals Society

References

Aiken, G. R., Aiken, G. R., McKnight, D. M., Wershaw, R. L. and MacCarthy, P., 1985 Isolation and concentration techniques for aquatic humic substances Humic Substances in Soil, Sediment, and Water New York Wiley 363 – 385.Google Scholar
Andreux, F., Golebiowska, D., Chone, T., Jacquin, F. and Metche, M., 1977 Characterisation et transformations en milieu mull d’un modele humique issu de l’autoxydation du systeme catechol-glycine et marque selectivement au carbon-14 Soil Organic Matter Studies II 43 – 57.Google Scholar
Borchardt, G. A., Dixon, J. B. and Weed, S. B., 1977 Montmorillonite and other smectite minerals Minerals in Soil Environments Madison, Wisconsin Soil Science Society of America 293 – 330.Google Scholar
Bremner, J. M., McLaren, A. D. and Peterson, G. H., 1967 Nitrogenous compounds SoilBiochemistry, Vol. 1 New York Marcel Dekker 19 – 66.Google Scholar
Bremner, J. M. and Mulvaney, C. S., 1982 Nitrogen-Total Methods of Soil Analysis, pt. 2 9 595 – 624.Google Scholar
Eltantawy, I. W. and Arnold, P. W., 1973 Reappraisal of ethylene glycol monoethyl ether (EGME) method for surface area estimation of clays J. Soil Sci. 24 232 – 238.CrossRefGoogle Scholar
Flaig, W., Beutelspacher, H., Rietz, E. and Gieseking, J. E., 1975 Chemical composition and physical properties of humic substances Soil Components, Vol. 1, Organic Components New York Springer-Verlag 1 – 211.Google Scholar
Germida, J. J. and Casida, L. E. Jr., 1980 Myceloid growth of Arthrobacter globiformis and other Arthrobacter species J. Bacteriol. 144 1152 – 1158.CrossRefGoogle ScholarPubMed
Haider, K., Frederick, L. R. and Flaig, W., 1965 Reactions between amino acid compounds and phenols during oxidation Plant Soil 22 49 – 64.CrossRefGoogle Scholar
Hatcher, P. G., Breger, I. A. and Mattingly, M. A., 1980 Structural characteristics of fulvic acids from continental shelf sediments Nature 285 560 – 562.CrossRefGoogle Scholar
Hayes, MHB, Aiken, G. R., McKnight, D. M., Wershaw, R. L. and MacCarthy, P., 1985 Extraction of humic substances from soils Humic Substances in Soil, Sediment, and Water New York Wiley 329 – 362.Google Scholar
Hsieh, C. S. and Wang, M. K., 1989 Taiwan Soils Taichung, Taiwan Published by National Chung Hsing University 161 – 203.Google Scholar
Jackson, M. L., 1979 Soil Chemical Analysis—Advanced Course 2 Madison, Wisconsin Published by the author 100 – 166.Google Scholar
Keeney, D. R. and Nelson, D. W., 1982 Nitrogen—Inorganic forms Methods of Soil Analysis, pt. 2 9 643 – 658.Google Scholar
Leenheer, J. A., Aiken, G. R., McKnight, D. M., Wershaw, R. L. and MacCarthy, P., 1985 Fractionation techniques for aquatic humic substances Humic Substances in Soil, Sediment, and Water New York Wiley 409 – 429.Google Scholar
Martin, J. P., Haider, K., Kirk, T. K., Higuchi, T. and Chang, H., 1980 Microbial degradation and stabilization of 14C-labeled lignins, phenols, and phenolic polymers in relation to soil humus formation Lig-nin Biodegradation: Microbiology, Chemistry and Potential Applications, Vol. I Boca Raton, Rorida CRC Press, Inc. 77 – 100.Google Scholar
McKeague, J. A., Cheshire, M. V., Andreux, F., Berthelin, J., Huang, P. M. and Schnitzer, M., 1986 Organo-mineral complexes in relation to pedogenesis Interactions of Soil Minerals with Natural Or-ganics and Microbes Madison, Wisconsin Soil Science Society of America 549 – 592.Google Scholar
Olson, B. M., McKercher, R. B. and Germida, J. J., 1984 Microbial population in trifluralin-treated soil Plant Soil 76 379 – 387.CrossRefGoogle Scholar
Schnitzern, M., 1977 Recent findings on the characterization of humic substances extracted from soils from widely differing climatic zones Soil Organic Matter Studies II Vienna IAEA-SM-211/7 117 – 130.Google Scholar
Schnitzer, M., Barr, M. and Hartenstein, R., 1984 Kinetics and characteristics of humic acids produced from simple phenols Soil Biol. Biochem. 16 371 – 376.CrossRefGoogle Scholar
Schnitzer, M. and Ghosh, K., 1982 Characteristics of water-soluble fulvic acid-copper and fulvic acid-iron complexes Soil Sci. 134 354 – 363.CrossRefGoogle Scholar
Schnitzer, M. and Lévesque, M., 1979 Electron spin resonance as a guide to the degree of humification of peats Soil Sci. 127 140 – 145.CrossRefGoogle Scholar
Schnitzer, M. and Skinner, S. I. M., 1963 Organo-metallic interactions in soils: 1. Reactions between a number of metal ions and the organic matter of a podzol Bh horizon Soil Sci. 96 86 – 93.CrossRefGoogle Scholar
Senesi, N. and Schnitzer, M., 1977 Effect of pH, reaction time, chemical reduction and irradiation on ESR spectra of fulvic acids Soil Sci. 123 224 – 234.CrossRefGoogle Scholar
Shindo, H. and Huang, P. M., 1982 Role of Mn(IV) oxide in abiotic formation of humic substances in the environment Nature 298 363 – 365.CrossRefGoogle Scholar
Shindo, H. and Huang, P. M., 1984 Catalytic effects of manganese(IV), iron(III), aluminum and silicon oxides on the formation of phenolic polymers Soil Sci. Soc. Amer. J. 48 927 – 934.CrossRefGoogle Scholar
Shindo, H. and Huang, P. M., 1984 Significance of Mn(IV) oxide in abiotic formation of organic nitrogen complexes in natural environments Nature 308 57 – 58.CrossRefGoogle Scholar
Shindo, H. and Huang, P. M., 1985 The catalytic power of inorganic components in the abiotic synthesis of hydro-quinone-derived humic polymers Appl. Clay Sci. 1 71 – 81.CrossRefGoogle Scholar
Shindo, H. and Huang, P. M., 1985 Catalytic polymerization of hydroquinone by primary minerals Soil Sci. 139 505 – 511.CrossRefGoogle Scholar
Solomon, D. H., 1968 Clay minerals as electron acceptors and/or electron donors in organic reactions Clays & Clay Minerals 16 31 – 39.CrossRefGoogle Scholar
Solomon, D. H. and Hawthorne, D. G., 1983 Chemistry of Pigments and Fillers New York Wiley 179 – 258.Google Scholar
Stevenson, F. J., 1982 Humus Chemistry New York Wiley 1 – 308.Google Scholar
Swaby, R. J., Ladd, J. N. and Neale, G. J., 1962 Chemical nature, microbial resistance, and origin of soil humus Int. Soc. Soil Sci. Trans. Comm. IV. New Zealand Soil Bureau, P. B., Lower Hutt 197 – 202.Google Scholar
Swift, R. S., Aiken, G. R., McKnight, D. M., Wershaw, R. L. and MacCarthy, P., 1985 Fractionation of soil humic substances Humic Substances in Soil, Sediment, and Water New York Wiley 387 – 408.Google Scholar
Tennakoon, D. T. B. Thomas, J. M. and Tricker, M. J., 1974 Surface and intercalate chemistry of layer silicates. pt. II. An iron-57 Mössbauer study of the role of lattice-substituted iron in the benzidine blue reaction of mont-morillonite J. Chem. Soc., Dalton 2211 – 2215.CrossRefGoogle Scholar
Theng, B. K. G., 1974 The Chemistry of Clay-Organic Reactions New York Wiley 261 – 291.Google Scholar
Theng, B. K. G. Wake, J. R. H. and Posner, A. M., 1966 The infrared spectrum of humic acid Soil Sci. 102 70 – 72.CrossRefGoogle Scholar
Tiessen, H., Bettany, J. R. and Stewart, J. W. B., 1981 An improved method for the determination of carbon in soils and soil extracts by dry combustion Comm. Soil Sci. Pl. Anal. 12 211 – 218.CrossRefGoogle Scholar
Umbreit, W. W., Burris, R. H. and Stauffer, J. F., 1964 Manometric Techniques: A Manual Describing Methods Applicable to the Studies of Tissue Metabolism 4 Minneapolis, Minnesota Burgess Publishing.Google Scholar
Wagner, G. H. and Stevenson, F. J., 1965 Structural arrangement of functional groups in soil humic acid as revealed by infrared analyses Soil Sci. Soc. Amer. Proc. 29 43 – 58.CrossRefGoogle Scholar
Wang, T. S. C. Chen, J. H. and Hsiang, W. M., 1985 Catalytic synthesis of humic acids containing various amino acids and dipeptides Soil Sci. 140 3 – 10.CrossRefGoogle Scholar
Wang, T. S. C. Huang, P. M., Chou, C. H. and Chen, J. H., 1986 The role of soil minerals in the abiotic polymerization of phenolic compounds and formation of humic substances Interactions of Soil Minerals with Natural Or-ganics and Microbes 17 251 – 281.Google Scholar
Wang, T. S. C. Kao, M. M. and Li, S. U., 1978 A new proposed mechanism of formation of soil humic substances Studies and Essay in Commemoration of the Golden Jubilee ofAcademia Sinica Taipei, Taiwan Academic Sinica 357 – 372.Google Scholar
Wang, T. S. C. Wang, M. C., Ferng, Y. L. and Huang, P. M., 1983 Catalytic synthesis of humic substances by natural clays, silts, and soils Soil Sci. 135 350 – 360.CrossRefGoogle Scholar