NaOH(KOH)-catalyzed vinylation of cellulose with acetylene gas in water
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ORIGINAL RESEARCH
NaOH(KOH)-catalyzed vinylation of cellulose with acetylene gas in water Lidiya N. Parshina . Ludmila A. Oparina . Anatolii P. Tantsyrev . Nina K. Gusarova . Boris A. Trofimov
Received: 15 June 2020 / Accepted: 3 September 2020 Ó Springer Nature B.V. 2020
Abstract Diverse mercerized celluloses (powder cellulose and kraft pulp) have been successfully vinylated with acetylene in an aqueous solution of alkali metal hydroxides (KOH or NaOH) at 125–140 °C. Depending on the reaction conditions, degree of substitution (DS) of the hydroxyl groups by highly reactive polymerazable vinyloxy groups ranges 0.08–0.73, the yields of vinyl celluloses being 24–75%. The process is accompanied by alkaline degradation of the cellulose macromolecule. Keywords Acetylene Cellulose Nucleophilic addition Alkali solutions Vinyl cellulose
Introduction The progressive depletion of hydrocarbon resources, coupled with environmental concerns, has prompted
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10570-020-03435-9) contains supplementary material, which is available to authorized users. L. N. Parshina L. A. Oparina A. P. Tantsyrev N. K. Gusarova B. A. Trofimov (&) A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russia e-mail: [email protected]
researchers to search for alternative feedstock as well as eco-friendly routes to the production of chemicals. Biomass as a globally accessible and renewable raw material is considered as one of the most promising candidates for such feedstock, which could partially or even completely replace the currently employed fossils (Belgacem and Gandini 2008; Gallezot 2012; Besson et al. 2014; Mika et al. 2018; Popa and Volf 2018; Sudarsanam et al. 2019). Among constantly reproducible plant biomass, cellulose is of particular value. It represents the most ubiquitous inexpensive and biocompatible natural polymer, capable of biodegradation (Klemm et al. 2005). Also, the technologies for cellulose processing have been well developed (Klemm et al. 2005; Heinze et al. 2006, 2018; Wertz et al. 2010; Fox et al. 2011; Kostag et al. 2019). Cellulose esters and ethers were and remain very important technical derivatives of cellulose (Klemm et al. 2005; Heinze et al. 2006, 2018; Wertz et al. 2010; Fox et al. 2011; Kostag et al. 2019). They are produced in hundred thousand tons per year (Klemm et al. 2005; Heinze et al. 2018) and are intensively used in the food (Wu¨stenberg 2014), cosmetic (Lochhead 2007), and pharmaceutical (Shokri and Adibkia 2013; Arca et al. 2018) industry, in the manufacture of artificial fibers (Klemm et al. 2005; Heinze et al. 2006, 2018) and membranes (Klemm et al. 2005; Heinze et al. 2006), as selective stationary phases in chromatography (Heinze et al. 2006), building (Klemm et al. 2005; Heinze et al. 2018) and packing (Johansson et al. 2012) materials,
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