Thermal destruction of d -mannose condensation products using p -aminoacetanilide in solvent-free systems
https://doi.org/10.21285/2227-2925-2020-10-4-581-589
Abstract
Thermal destruction of D-mannose condensation products using p-aminoacetanilide in solvent-free systems, such as paraffinic oil and a KBr-matrix, was studied by the methods of electronic and vibrational spectroscopy. The thermal destruction of mannosylamine in a KBr matrix is accompanied by intense coloration. At the same time, the bands in the IR spectra characterizing the functionalization of aminoacetanilide retain their position and intensity, which indicates the absence of transformation of the amine fragment. The appearance of the 1645, 1680, 1690 cm-1 bands of enone O=C-C=C- fragments is noted, along with the 1750 and 1780 cm-1 bands attributed to the stretching C=O vibrations of esters and lactones likely formed as a result of transformation of the primary mannosylamine degradation products. The thermal destruction of a mannosylamine suspension in paraffinic oil shows a lower transformation of the mannosyla-mine structure in comparison with experimental processes in a KBr matrix. The spectra depict the bands of С = O vibrations in different structural environments, as well as the signal shift of 1280 cm-1 into the low- frequency region characterizing the elimination of arylamine. The reflection spectra of the alcohol solutions of destruction products demonstrate the presence of only the 1750 cm-1 band; the 1780 cm-1 band does not appear probably due to the instability of lactones in solutions, which causes their recyclization. An analysis of vibrational spectra showed the absence of bands characteristic of melanoidin N-heterocycles due to the predominant formation of acyclic conjugated systems and carboxylic acid derivatives in the studied solvent-free systems. In the electronic spectra of the alcohol solutions of destruction products in both systems, maxima of about 260 nm were recorded. These maxima correspond to the absorption of oxyenone chromophores and the continuous absorption region in the visible part of the spectrum, caused by the formation of extended chromophores, i.e. condensation products of the intermediates of mannosylamine decomposition. The obtained results can be useful both when selecting conditions for the Maillard reaction with a given functionalization and when developing methods for the synthesis of antioxidant agents for protecting polymers and oils.
About the Author
I. S. Cherepanov
Udmurt State University
Russian Federation
Russian Federation
Igor S. Cherepanov - Cand. Sci. (Chemistry), Associate Professor.
1, Universitetskaya St., Izhevsk, 426034References
1. Gobert J, Glomb MA. Degradation of glucose: reinvestigation of reactive a-dicarbonyl compounds. Journal of Agricultural and Food Chemistry. 2009; 57(18):8591 -8597. https://doi.org/10.1021/jf9019085
2. Wnorowski A, Yaylayan V. Influence of pyrolytic and aqueous-phase reactions on the mechanism of formation of Maillard products. Journal of Agricultural and Food Chemistry. 2000;48(8):3549-3554. https://doi.org/10.1021/jf9913099
3. Rubinsztain Y, Yariv S, Ioselis P, Aizenshtat Z, Ikan R. Characterization of melanoidins by IR spectroscopy - I. Galactose - glycine melanoidins. Organic Geochemistry. 1986;9(3):117-125. https://doi.org/10.1016/0146-6380(86)90101-4
4. Cherepanov IS, Abdullina GM. Study of dialyzable melanoidin fractions in aqueuos-ethanolic D-lactose - aryl amine systems. Izvestiya Vuzov. Prikladnaya Khimiya i Biotekhnologiya = Proceedings of Universities. Applied Chemistry and Biotechnology. 2017;7(2):181-184. (In Russian) https://doi.org/10.21285/2227-2925-2017-7-2-181-184
5. Cherepanov IS, Abdullina GM, Kornev VI. Interaction of D-lactose with aromatic amines in aqueous-ethanolic medium. Butlerovskie soob-shcheniya = Butlerov Communication. 2016;46(4): 71-76. (In Russian)
6. Abraham JP, Sajan D, Joe IH, Jayakumar JS. Molecular structure, spectroscopic studies and first-order molecular hyperpolarizabilities of p-amino acetanilide. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy. 2008;71(2):355- 367. http://dx.doi.org/10.1016/j.saa.2008.01.010
7. Gatial A, Polovkova А, Breza М. Quantumchemical study of N,N’-diphenyl-p-phenylenedia-mine (DPPD) dehydrogenation. Acta Chimica Slo-vaca. 2008;1(1):72-84.
8. Ahmad I, Ullah J, Ishaq M, Khan H, Gul K, Sibbiqui S, et al. Monitoring of oxidation behavior in mineral base oil additized with biomass derived antioxidant using FT-IR spectroscopy. RSC Advances. 2015;5:101089-101100. https://doi.org/10.1039/C5RA17753G
9. Cherepanov IS. Synthesis and antioxidative activity of D-glucose - p-aminoacetanilide condensation product. Khimiya i tekhnologiya organi-cheskikh vestchestv = Chemistry and Technology of Organic Substances. 2020;3:71-78 (In Russian)
10. Kulakov IV. Synthesis of new N-aminogly-cosides based on halo-substituted p-phenylenedia-mines and p-aminiphenols. Chemistry of Natural Compounds. 2009;45(4):522-524. https://doi.org/10.1007/s10600-009-9392-0
11. Kublashvili R. N-glucosides of aminobenzoic acids and aminophenols. Chemistry of Natural Compounds. 2003;39(6):586-588.
12. Lewin M, Ziderman I, Weiss N, Basch A, Ettinger A. Chromogen formation during alkaline degradation of hydrocellulose and cellobiose. Carbohydrate Research. 1978;62:393-398.
13. Lievens C, Mourant D, He M, Gunawan R, Li X, Li C-Z. An FT-IR spectroscopic study of carbonyl functionalities in bio-oil. Fuel. 2011;90(11):3417-3423. https://doi.org/10.1016/J.fuel.2011.06.011
14. Sokolov AV, Alekseev EE, Khizhnyak SD, Ga-lytsin VP, Pakhomov PM. Thermooxidative destruction of solvent during production high-strength fibers of ul-trahigh-molecular polyethylene (UHMPE) by gelformation method. Fibre Chemistry. 2018;50(4):270-273. https://doi.org/10.1007/s10692-019-09974-7
15. Haffenden LJW, Yaylayan VA. Nonvolatile oxidation products of glucose in Maillard model systems: formation of saccharinic and aldonic acids and their corresponding lactones. Journal of Agricultural and Food Chemistry. 2008;56(5):1638-1643. https://doi.org/10.1021/jf073290c
16. Kavitha E, Sundaraganesan N, Sebastian S. Molecular structure, vibrational spectroscopic and HOMO, LUMO studies of 4-nifroaniline by density functional method. Indian Journal of Pure & Applied Physics. 2010;48:20-30.
17. Homma S, Terasawa N, Kubo T, Yoneyawa-Ishii N, Aida K, Fujimaki M. Changes in chemical properties of melanoidins by oxidation and reduction. Bioscience, Biotechnology and Biochemistry. 1997;61(3): 533-535. https://doi.org/10.1271/bbb.61.533
18. Wolf D, Hoffman C, Aldrich P, Skeggs H, Wright L, Folkers K. Determination of structure of e,6-dihydroxy-e-methylvaleric acid. Nutrition Reviews. 1986;44(10):337-339. https://doi.org/10.111 1/j.1753-4887.1986.tb07563.x
19. Nonier M, Vivas N, Vivas de Gaulejas N, Mouche C, Rossy Huguet C, Daugey N. Purification and partial characterization of melanoidins fractions from toasted oak heartwood, comparison with melanoidins from roasted coffee. Journal of Food Research. 2018;7(6):37-57. https://doi.org/10.5539/jfr.v7n6p37
20. Lewin M. Oxidation and aging of cellulose. Macromolecular Symposia. 1997;118(1):715-724. https://doi.org/10.1002/masy.19971180192
21. Voigt M, Smuda M, Pfahler C, Glomb MA. Oxygen-dependent fragmentation reactions during the degradation 1-deoxy-D-erythro-hexo-2,3-diulose. Journal of Agricultural and Food Chemistry. 2010;58(9): 5685-5691. https://doi.org/10.1021/jf100140h
22. Beck J, Ledi F, Sengl M, Severin T. Formation of acids, lactones and esters through the Maillard reaction. Zeitschrift fur Lebensmittel-Untersuchung und Forschung = Journal of Food Study and Research. 1990;190(3):212-216. https://doi.org/10.1007/BF01192968
23. Moshin G, Schmitt F-J, Kanzler C, Epping JD, Flemig S, Hornemann A. Structural characterization of melanoidins formed from D-glucose and L-alanine at different temperatures applied FTIR, NMR, EPR and MALDI-ToF-MS. Food Chemistry. 2018;245;761-767. https://doi.org/10.1016/j.foodchem.2017.11.115
Review
For citations:
Cherepanov I.S. Thermal destruction of d -mannose condensation products using p -aminoacetanilide in solvent-free systems. Proceedings of Universities. Applied Chemistry and Biotechnology. 2020;10(4):581-589. (In Russ.) https://doi.org/10.21285/2227-2925-2020-10-4-581-589
Views:
330
Email this article 