Continuous flow microfluidic implementation of a fluorescent marker into a polyacrylate moiety
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Continuous flow microfluidic implementation of a fluorescent marker into a polyacrylate moiety Maxim Oshchepkov 1,2 & Inna Solovieva 2 & Aleksey Menkov 1,2 & Sergey Tkachenko 1,2 & Vladimir Udovenko 1,2 & Konstantin Popov 1 Received: 31 January 2020 / Accepted: 7 April 2020 # Akadémiai Kiadó 2020
Abstract Fluorescent-tagged scale inhibitor application is a new trend in water treatment. Herein the results on the comparative study of the batch and a continuous flow microfluidic conjugation of 1,8-naphthalimide with acrylic acid and with allylsulfonate to give a fluorescenttagged polyacrylate and polyalkylsulfonate/acrylate copolymer with molecular mass 2000–4000 Da are reported. It is demonstrated that a better reaction yield (91%) and less side reactions take place in the flow system compared with conventional method. Keywords Fluorescent markers . Hydrophilic polymers . Scale inhibition applications . Continuous flow microfluidics
1 Introduction Fluorescent-tagged scale inhibitor application is a new trend in water treatment [1–3]. In 1992 the Nalco Chemical Company first patented an implementation of a fluorescent fragment into the polymeric scale inhibitor [4]. This communication was soon followed by numerous patents issued by Nalco, Rhodia Chimie, Kemira Chemicals Inc., Ecolab USA Inc., JSC Fine Chemicals R&D Centre as well as by a great number of research reports [1]. Most of the publications in the field were published over the last decade. An increasing interest to the fluorescent antiscalants is associated with a need of a better scale inhibitor concentration control in industrial applications: oilfield, boilers, heat exchangers, evaporation plants etc. Indeed, the concentration of antiscalants in the circulating Electronic supplementary material The online version of this article (https://doi.org/10.1007/s41981-020-00093-7) contains supplementary material, which is available to authorized users. * Maxim Oshchepkov [email protected] 1
JSC “Fine Chemicals R&D Centre”, 107258 Moscow, Russia
2
Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russia
system is usually changed by evaporation of water, reagent sorption on the pipe surfaces and scale particles, and by a periodical discharge of the circulating water with some deposit. On the other hand, these conjugates are very promising agents for the scale inhibition mechanisms studies [5, 6] as well as possible anticancer agents [7]. Among the fluorescent fragments 1,8-naphthalimide derivatives, Fig. 1, have a lot of advantages [1, 3, 6–8]. However, the batch synthesis [8] of 1,8-naphthalimide conjugate with acrylic acid to give a fluorescent-tagged polyacrylate with molecular mass 2000–4000 Da revealed some problems: the difficulties of reaction control and local reaction mass overheating. In order to eliminate these drawbacks in a recent study the continuous-flow synthesis technique was tested. Indeed, the continuous-flow synthesis has been proved to be a technique with many advantages over the conventional batch reactions
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