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Biomass-Derived Production of Itaconic Acid As a Building Block in Specialty Polymers

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Biomass-Derived Production of Itaconic Acid As a Building Block in Specialty Polymers polymers Review Biomass-Derived Production of Itaconic Acid as a Building Block in Specialty Polymers Bernadette-Em˝okeTeleky 1 and Dan Cristian Vodnar 2,* 1 Institute of Life Sciences, University of Agricultural Sciences and Veterinary Medicine, Calea Mănă¸stur3-5, 400372 Cluj-Napoca, Romania; [email protected] 2 Faculty of Food Science and Technology, Institute of Life Sciences, University of Agricultural Sciences and Veterinary Medicine of Cluj-Napoca, Calea Mănăs, tur 3-5, 400372 Cluj-Napoca, Romania * Correspondence: [email protected]; Tel.: +40-747-341-881 Received: 10 May 2019; Accepted: 7 June 2019; Published: 11 June 2019 Abstract: Biomass, the only source of renewable organic carbon on Earth, offers an efficient substrate for bio-based organic acid production as an alternative to the leading petrochemical industry based on non-renewable resources. Itaconic acid (IA) is one of the most important organic acids that can be obtained from lignocellulose biomass. IA, a 5-C dicarboxylic acid, is a promising platform chemical with extensive applications; therefore, it is included in the top 12 building block chemicals by the US Department of Energy. Biotechnologically, IA production can take place through fermentation with fungi like Aspergillus terreus and Ustilago maydis strains or with metabolically engineered bacteria like Escherichia coli and Corynebacterium glutamicum. Bio-based IA represents a feasible substitute for petrochemically produced acrylic acid, paints, varnishes, biodegradable polymers, and other different organic compounds. IA and its derivatives, due to their trifunctional structure, support the synthesis of a wide range of innovative polymers through crosslinking, with applications in special hydrogels for water decontamination, targeted drug delivery (especially in cancer treatment), smart nanohydrogels in food applications, coatings, and elastomers. The present review summarizes the latest research regarding major IA production pathways, metabolic engineering procedures, and the synthesis and applications of novel polymeric materials. Keywords: itaconic acid; biotechnology; biosynthetic pathways; Aspergillus terreus; polymers; hydrogels; drug delivery 1. Introduction The use of non-renewable petrochemicals still leads today‘s petrochemicals industry, while biomass is the only renewable source of organic carbon on Earth. Organic acid production through microbial fermentation of different biomass wastes can play an essential role in the production of biochemical building-blocks or even bioactive compounds [1–4]. Isikgor & Becer [5] have recently presented over 200 significant compounds derived from different biomass sources and structures with pretreatment methods that can also reduce the production costs of chemicals and polymers. Lignocellulosic biomass such as energy crops, agricultural and forest management residues, and municipal wastes are versatile renewable energy sources [6]. They can potentially replace fossil fuels in power and heat generation, and natural gases in the production of bio-based chemicals. A recent review analyzed the present situation of bio-based chemical production through biological and chemical pathways, presenting 435 chemicals and materials obtained from renewable resources [7]. Biomass and biomass-derived wastes have the potential to provide low-cost sources of sugar and could be the best substitute for non-renewable petrochemicals. Polymers 2019, 11, 1035; doi:10.3390/polym11061035 www.mdpi.com/journal/polymers Polymers 2019, 11, 1035 2 of 27 Polymers 2019, 11, x FOR PEER REVIEW 2 of 26 A currentA current major major problem problem is theis the high high amount amount of of plastics plastics present present inin the environment and and their their role role in environmentalin environmental pollution, pollution, since since they they don’tdon’t degra degradede under under natural natural circumstances. circumstances. These These plastics plastics are aremostly composed composed of of synthetic synthetic polymers polymers derived derived mainly mainly from from petrochemicals. petrochemicals. A solution A solution for this for thisnever-ending never-ending problem problem is is the the exploration exploration of of altern alternativeative bio-based bio-based and and biodegradable biodegradable plastics plastics like like biosyntheticbiosynthetic polymers polymers [8], [8], polylactic polylactic acid acid (PLA), (PLA), thermoplastic thermoplastic starch starch (TPS)(TPS) or even natural natural polyesters polyesters likelike polyhydroxyalkanoates polyhydroxyalkanoates (PHA) (PHA) [9 ,[9,10].10]. OneOne of the of mostthe most important important classes classes of compounds of compou obtainednds obtained from lignocellulosefrom lignocellulose biomass biomass are organic are acids.organic Bio-based acids. organic Bio-based acids organic are products acids are that products are derived that are from derived different from biomassdifferent sources, biomass whichsources, are sustainable,which are cost-e sustainable,ffective, cost-effective, and environmentally and environmen friendly.tally Among friendly. these, Among itaconic these, acid (IA),itaconic together acid (IA), with together with its derivatives, is an essential renewable chemical because it has various uses in the its derivatives, is an essential renewable chemical because it has various uses in the pharmaceutical pharmaceutical and food industry, and also presents a feasible substitute for unsaturated acids like and food industry, and also presents a feasible substitute for unsaturated acids like acrylic, methacrylic, acrylic, methacrylic, maleic, fumaric acid and their derivatives [11–13]. Integration of IA in polymers maleic, fumaric acid and their derivatives [11–13]. Integration of IA in polymers is very efficient [14]. is very efficient [14]. IA is an unsaturated dicarboxylic acid (C5H6O4), also known as 2-methylenebutanedioic acid, IA is an unsaturated dicarboxylic acid (C5H6O4), also known as 2-methylenebutanedioic acid, propylenepropylene dicarboxylic dicarboxylic acid, acid, or 2-methylenesuccinic or 2-methylenesuccinic acid acid (Figure (Figure1a,b). 1.a,b). IA isIA highly is highly soluble soluble in water in water and alcoholsand alcohols [15], stable [15], at stable average at average temperatures, temperatures, and, being and, being a weak a weak acid, itacid, is also it is stablealso stable in middle-basic, in middle- neutralbasic, and neutral acidic and conditions acidic conditions [16]. It has[16]. an It has appearance an appearance of white of white crystalline crystalline powder powder or crystals, or crystals, and it isand odor-free it is odor-free [17,18]. [17,18]. The variation The variation of IA’s of functionalIA’s functional groups groups makes makes it an it an effi efficientcient intermediate intermediate to produceto produce different different complex complex organic organic compounds. compounds. Itcan It can participate participate in in a a wide wide varietyvariety of reactions reactions like like esterificationesterification with with alcohols, alcohols, salt salt formation formation with with metals, metals, production production ofof anhydride, polymerization, polymerization, and and additionaladditional reactions reactions [19 [19].]. FigureFigure 1. The1. The chemical chemical structure structure (a), properties properties (b (b) and) and chemical chemical synthesis synthesis from from citric citric acid ( acidc) Δ: (heatc) D : heatinput. input. BaupBaup S. discoveredS. discovered IA IA in in 1837 1837 as as a producta product of of thermal thermal decomposition decomposition of citric acid acid [20], [20], while while KinoshitaKinoshita was was the the first first to reportto report production production of of IA IA with withAspergillus Aspergillus itaconicusitaconicus in 1931 [21]. [21]. Later, Later, the the focusfocus for IAfor fermentationIA fermentation was was shifted shifted mostly mostly to toA. A. terreus terreusstrains. strains. NelsonNelson et al. [22] [22] studied studied A.A. terreus terreus NRRLNRRL strain strain 1960 1960 and and established established a biotechnicala biotechnical process; process; while whileEimhjellen Eimhjellen et al. [19] [19] studied studied the the effect effect of diofff erentdifferent substrates substrates (various (various sugars sugars and and alcohols) alcohols) on on IA IA production. production. Production with with A.A. terreus terreus NRRLNRRL 1960 1960 in 20in mL20 mL media media and and 5% 5% substrate substrate in in 100 100 mL mL flasks flasksresulted resulted inin the highest IA IA production production withwith sucrose sucrose (57%) (57%) and andd-glucose D-glucose (52%). (52%). OtherOther substrates substrates like like cellobiose cellobiose (41%), (41%), D-mannosed-mannose (32%), (32%), d- d-xylosexylose (31%), (31%),d D-fructose-fructose (26%)(26%) andand glycerolglycerol (23%) (23%) produced produced significant significant amounts amounts of ofIA IA as aswell well [23]. [23 ]. TheThe initial initial industrial industrial production production of IAof IA used used a chemical a chemical approach, approach, i.e., i.e., the the pyrolysis pyrolysis of of citric citric acid acid to itaconicto itaconic anhydride, anhydride, followed followed by the by hydrolysis the hydrolysis of the anhydrideof the anhydride (Figure 1(Figurec) [ 20]. 1.c) Alternative [20]. Alternative methods weremethods decarboxylation were decarboxylation of aconitic acid, of dryaconitic distillation acid, dr ofy anhydride,distillation andof anhydride,
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