Abstract
The chloromethylated polystyrene–divinylbenzene (Cl-PS–DVB) was obtained via the chloromethylation of high cross-linked polystyrene–divinylbenzene (PS–DVB). Methylal, trioxymethylene and thionyl chloride were applied as reactants. The obtained Cl-PS–DVB (chloromethylated polystyrene–divinylbenzene) was characterized by the BET and FT-IR. Also, the catalyst, reaction time and reaction temperature were optimized. The chlorine content of the obtained Cl-PS–DVB reached 19% under the catalysis of FeCl3 at 45 °C. The chloromethylation method was thought to be environmental friendly because low toxic reactant (methylal, trioxymethylene and thionyl chloride) were applied in the in situ chloromethylation of PS–DVB in this process instead of using hypertoxic chloromethyl ether (BCME) directly. Also, the low production cost of this reaction gives it a bright prospect in industrial application.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Chen ZB, Kang L, Di DL, Dong F, Yu H (2011) Chloromethylation research of LX-1180 macroporous adsorption resin in ultrasonic environment. Adv Mater Res 233:2893–2897
Cheng Z, Zhu X, Kang ET, Neoh KG (2006) Modification of poly(ether imide) membranes via surface-initiated atom transfer radical polymerization. Macromolecules 39:1660–1663
Dragan ES, Avram E, Axente D, Marcu C (2004) Ion-exchange resins. III. Functionalization–morphology correlations in the synthesis of some macroporous, strong basic anion exchangers and uranium-sorption properties evaluation. J Polym Sci Part A Polym Chem 42:2451–2461
Feinberg RS, Merrifield RB (1974) Zinc chloride-catalyzed chloromethylation of resins for solid phase peptide synthesis. Tetrahedron 30:3209–3212
Hu YL, Lu M, Ge Q, Wang PC, Lu TT (2010) A novel and efficient procedure for the preparation of 4,4′-bis (chloromethyl) biphenyl by chloromethylation of biphenyl catalyzed by PEG 1000-DAIL under homogeneous catalysis in aqueous media. J Ind Eng Chem 16:615–619
Huang J, Huang K, Liu S, Luo Q, Shi S (2008) Synthesis, characterization, and adsorption behavior of aniline modified polystyrene resin for phenol in hexane and in aqueous solution. J Colloid Interface Sci 317:434–441
Jain VK, Pandya RA, Pillai SG, Shrivastav PS (2006) Simultaneous preconcentration of uranium(VI) and thorium(IV) from aqueous solutions using a chelating calix[4]arene anchored chloromethylated polystyrene solid phase. Talanta 70:257–266
Jones M (1984) A novel, convenient synthesis of chloromethyl methyl ether. Chemischer Informationsdienst 2:727
Kedem M, Margel S (2002) Synthesis and characterization of micrometer-sized particles of narrow size distribution with chloromethyl functionality on the basis of single-step swelling of uniform polystyrene template microspheres. J Polym Sci Part A Polym Chem 40:1342–1352
Masuda T, K-i Kitahara, Aikawa Y, Arai S (2002) High-performance liquid chromatographic separation of carbohydrates on a stationary phase prepared from polystyrene-based resin and novel amines. J Chromatogr A 961:89–96
Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I, Kargar H (2005) Mild and efficient oxidation of alcohols with sodium periodate catalyzed by polystyrene-bound Mn(III)porphyrin. Bioorg Med Chem 13:2901–2905
Mondal BC, Das AK (2002) Microwave-assisted synthesis of a new chelating resin containing 2-aminothiophenyl S-acetic acid and its application to the determination of lead. React Funct Polym 53:45–52
Sadeek SA, El-Sayed MA, Amine MM, Abd El-Magied MO (2014) A chelating resin containing trihydroxybenzoic acid as the functional group: synthesis and adsorption behavior for Th(IV) and U(VI) ions. J Radioanal Nucl Chem 299:1299–1306
Shevelev D, Vladenkova O (2008) Effect of catalyst used for chloromethylation of styrene-divinylbenzene copolymer on the service characteristics of the highly basic anion exchanger obtained. Russ J Appl Chem 81:896–898
Sophiamma PN, Sreekumar K (1997) Polystyrene-based hydroxamic esters: preparation and application as acyl transfer reagents. React Funct Polym 35:169–177
Teixeira VG, Coutinho FMB (2010) Morphological study on the reactivity of styrene-divinylbenzene copolymers in a chloromethylation reaction. J Appl Polym Sci 118:2389–2396
Zhang X, Jin Q, Dai L, Yuan S (2011) Facile synthesis of hypercrosslinked resins via chloromethylation and continuous condensation of simple aryl molecules. Bull Mater Sci 34:735–738
Acknowledgements
This work was financially supported by the Foundation of Hunan college students’ innovation and entrepreneurship education outside school base (Hunan education notice [2016]394).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Fu, Y., Huang, X., Zhong, S. et al. A new chloromethylation method based on polystyrene–divinylbenzene. Chem. Pap. 73, 2183–2188 (2019). https://doi.org/10.1007/s11696-019-00761-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-019-00761-6