Efficient conversion of glucosamine to ethyl levulinate catalyzed by methanesulfonic acid
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pISSN: 0256-1115 eISSN: 1975-7220
INVITED REVIEW PAPER
INVITED REVIEW PAPER
Efficient conversion of glucosamine to ethyl levulinate catalyzed by methanesulfonic acid Gwi-Taek Jeong† and Sung-Koo Kim Department of Biotechnology, School of Marine and Fisheries Life Science, Pukyong National University, Busan 48513, Korea (Received 2 April 2020 • Revised 14 May 2020 • Accepted 27 May 2020) AbstractThis study is focused on the possibility of using crustacean waste shells for sustainable biofuels and chemical production. We investigated the synthesis of ethyl levulinate (EL) from glucosamine by the methanesulfonic acidcatalyzed hydrothermal reaction using Box-Behnken design. In the ethyl levulinate synthesis, higher water content highly inhibited the formation of EL. Among the reaction factors, reaction temperature, catalyst concentration, and reaction time positively affected the outcome more than substrate concentration. The optimized reaction conditions were 200 oC reaction temperature, 60 g/L substrate concentration, 0.75 M catalyst concentration, and 44.9 min. Under these conditions, a 22.76 mol% EL yield was achieved. These results suggest that crustacean waste shells can be used for renewable feedstocks to produce valuable chemicals and biofuels. Keywords: Glucosamine, Ethyl Levulinate, Platform Chemical, Methanesulfonic Acid, Acid-catalyzed Hydrothermal Process
called versatile platform chemicals) have been reported using various biomass feedstocks by biological or thermo-chemical methods [2-4,10-12,14-20]. Levulinic acid has two functional groups (ketone and carboxylic acid). It is one of the 12 compounds reported by the DOE in 2004 as the “Top Value Added Chemicals from Biomass” [3] and top 10 chemicals revised in 2010 [21]. It
INTRODUCTION Climate change and the depletion of fossil resources have been seriously considered throughout the world. To overcome these problems, renewable energy resources have been introduced and researched. Bioenergy and biomass feedstocks have been regarded as renewable, sustainable, and a replacement for fossil resources [1-3]. Biofuels and chemicals, which originate from various feedstocks such as sugars, starches, lignocellulosics, and macro-/microalgae, have been sustainably converted by biological and/or thermochemical methods [2,4-7]. Recently, chitin/chitosan, derived from marine crustacean shells, has been investigated to produce biofuels and chemicals [8-12]. Chitin and chitosan, which are mainly composed of N-acetylD-glucosamine and D-glucosamine, respectively, are natural polymers (Scheme 1) [9,10]. These can be recovered from the exoskeletons of crustaceans and insects, and the cell walls of yeasts, fungi, and mushrooms [8-10]. Due to the similarity of the structure of chitin/chitosan with cellulose, chitosan can be partially hydrolyzed by some cellulases [9,13,14]. The amino sugar (2-Amino-2-deoxyglucose) [9,10], a glucosamine, is a monomer of chitosan. Glucosamine and chitosan have been commercially introduced in dietary supplements, cosmetics, pharmaceuticals,
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