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Complexes of polyvinylpyrrolidone and polyethylene glycol with palladium(II) ions: characterization and catalytic activity

Dina N. Akbayeva, Indira A. Smagulova, Azhar Timurkyzy, Botagoz S. Bakirova

Abstract


In this work, we obtained complexes by mixing aqueous solution of palladium(II) chloride with polyvinylpyrrolidone and polyethylene glycol. The composition of the complex compounds was determined by potentiometric and conductometric titration. IR spectroscopy and scanning electron microscopy (SEM) confirmed the coordination of polymeric ligand to palladium and allowed evaluating the morphology and features of the complex surface. The catalytic activity of the synthesized compounds in the oxidation of octene-1 by inorganic oxidizers (NaBrO3, K2S2O8) in aqueous-organic media in dimethyl sulfoxide (DMSO) under mild conditions was calculated. The reaction product was octanone-2, obtained in good yield (62–98%). Quantitative analysis of octanone-2 was made by the gas-chromatographic method. Mass spectrometry confirms the formation of octanone-2. The complexes are able to participate in five consecutive catalytic cycles without significant loss of catalytic efficiency. Oxidation of octene-1 proceeds by the oxidation-reduction mechanism and consists of two key stages.

Keywords


palladium(II) ions; polyvinylpyrrolidone; polyethylene glycol; catalysis; oxidation; octene-1

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References


Weissermel K, Arpe HJ. Industrial Organic Chemistry. 4th ed. Weinheim: Wiley-VCH; 2003. 491 p.

Tsuji J. Synthetic applications of the palladium-catalyzed oxidation of olefins to ketones. Synth. 1984;369–384. doi:10.1055/s-1984-30848

Takacs JM, Jiang XT. The Wacker reaction and related alkene oxidation reaction. Curr Org Chem. 2003;7(4):369–396. doi:10.2174/1385272033372851

Sharma GVM, Krishna PR. Carbohydrates: from ‘chirons’ to new glycosubstances. Curr Org Chem. 2004;8(13):1187–1209. doi:10.2174/1385272043370096

Kulkarni MG, Shaikh BY, Borhade AS, Chavhan SW, Dhondge AP, Gaikwad DD, Desai MP, Birhade DR, Dhatrak NR. Greening the Wacker process. Tetrahedron Lett. 2013;54:2293–2295. doi:10.1016/j.tetlet.2013.01.082

Pires MJD, Purificação SI, Santos AS, Marques MMB. The role of PEG on Pd- and Cu-catalyzed cross-coupling reactions. Synth. 2017;49:2337–2350. doi:10.1055/s-0036-1589498

Schroeter F, Soellner J, Strassner T. Cyclometalated palladium NHC complexes bearing PEG chains for Suzuki–Miyaura cross-coupling in water. Organometal. 2018;37(22):4267–4275. doi:10.1021/acs.organomet.8b00607

Han GH, Lee SH, Seo M, Lee KY. Effect of polyvinylpyrrolidone (PVP) on palladium catalysts for direct synthesis of hydrogen peroxide from hydrogen and oxygen. RSC Adv. 2020;10:19952–19960. doi:10.1039/D0RA03148H

Lu J. Sodium bromate: an eco-friendly brominating and oxidizing reagent. SYNLETT. 2011;6:0879–0880. doi:10.1055/s-0030-1259755

Bierenstiel M, D’Hondt PJ, Schlaf M. Investigations into the selective oxidation of vicinal diols to a-hydroxy ketones with the NaBrO3/NaHSO3 reagent: pH dependence, stoichiometry, substrates and origin of selectivity. Tetrahedron. 2005;61:4911–4917. doi:10.1016/j.tet.2005.03.056

Yamato T, Shinoda N. Highly efficient oxidation of alcohols catalysed by Nafion-cerium(IV) or Nafion-chromium(III). J Chem Research (S). 2002;8:400–402. doi:10.3184/030823402103172464

Shaabani A, Farhangi E, Rahmati A. Ionic liquid promoted selective oxidation of organic compounds with NaBrO3. Monatsh Chem. 2008;139:905–908. doi:10.1007/s00706-007-0840-x

Al-Hashimi M, Fisset E, Sullivan AC, Wilson JRH. Selective oxidation of sulfides to sulfoxides using a silica immobilised vanadyl alkyl phosphonate catalyst. Tetrahedron Lett.2006;47(46):8017–8019. doi:10.1016/j.tetlet.2006.09.065

Memarian HR, Mohammadpoor-Baltork I, Sadeghi MM, Samani ZS. Potassium peroxodisulfate: a convenient oxidizing agent for aromatization of 1,4-dihydroperidines. Indian J Chem. 2001;40B:727–728.

Safari A, Zeynizadeh B. Activated charcoal: a highly efficient promoter for selective oxidation of alcohols to aldehydes and ketones by K2S2O8 at solvent−free conditions. Curr Chem Lett. 2015;4:111–118. doi:10.5267/j.ccl.2015.4.001

Yang XY, Wang R, Wang L, Li J, Mao S, Zhang SQ, Chen N. K2S2O8-promoted C–Se bond formation to construct -phenylseleno carbonyl compounds and ,-unsaturated carbonyl compounds. RSC Adv. 2020;10:28902–28905. doi:10.1039/d0ra05927g

Walker FS, Bhattacharya SN, Senoff CV. Alkylated polyamine complexes of palladium(II). Inorg Synth. 1982;21:129–130.

McCombs JR, Michel BW, Sigman MS. Catalyst-controlled Wacker-type oxidation of homoallylic alcohols in the absence of protecting groups. J Org Chem. 2011;76(9):3609–3613. doi:10.1021/jo200462a

Liu M, Yan X, Liu H, Yu W. An investigation of the interaction between polyvinylpyrrolidone and metal cations. React Funct Polym. 2000;44(1):55–64. doi:10.1016/S1381-5148(99)00077-2

Gupta MN, Batra R, Tyagi R, Sharma A. Polarity index: the guiding solvent parameter for enzyme stability in aqueous-organic cosolvent mixtures. Biotechnol Prog. 1997;13(3):284–288. doi:10.1021/bp9700263

Moiseyev II. Pi-kompleksy v zhidkofaznom okislenii olefinov [-Complexes in liquid-phase oxidation of olefins]. Moscow: Nauka; 1970. 242 p. Russian.

Huheey JE. Inorganic Chemistry: Principles of structure and reactivity. 3d ed. New-York: Harper and Row; 1983. 936 р.

Rokosz K, Hryniewicz T, Matysek D, Raaen S, Valicek J, Dudek L, Harnicarova M. SEM, EDS and XPS analysis of the coatings obtained on titanium after plasma electrolytic oxidation in electrolytes containing copper nitrate. Mater. 2016;9(5):318. doi:10.3390/ma9050318

Akbayeva DN, Bakirova BS, Seilkhanova GA, Sitzmann H. Synthesis, characterization, and catalytic activity of palladium-polyvinylpyrrolidone complex in oxidation of octene-1. Bull Chem React Eng Catal. 2018;13(3):560–572. doi:10.9767/bcrec.13.3.1980.560-572




DOI: https://doi.org/10.15826/chimtech.2023.10.3.01

Copyright (c) 2023 Dina N. Akbayeva, Indira A. Smagulova, Azhar Timurkyzy, Botagoz S. Bakirova

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Chimica Techno Acta, 2014-2024
ISSN 2411-1414 (Online)
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