Itaconic acid

Members of a series of N,N′‐alkylene bisitaconamic acids were synthesized from the reaction between itaconic anhydride and a homologous group of aliphatic diamines with the general formula H2N (CH2)n NH2, where n = 4–12. Cyclodehydration of the acids in toluene gave the isomeric imides: bisitaconimide, biscitraconimide, and citra‐itaconimide. The isomeric imides were isolated, purified, and characterized for each diaminoalkane studied.

A trifunctional epoxy resin from itaconic acid (TEIA) was synthesized from a renewable resource‐based itaconic acid by allylation of itaconic acid to form diallyl itaconate by using m‐chloroperoxybenzoic acid as oxidizing agents followed by epoxidation of allylic C═C bond of diallyl itaconate methylhexahydropthalic anhydride as curing agent in the presence of 2‐methyl imidazole as a catalyst. The chemical structure of the synthesized resins was confirmed by Fourier transform infrared and nuclear magnetic resonance (1H‐NMR and 13C‐NMR) spectroscopy analysis. The mechanical, thermal, and rheological performances of the TEIA were also investigated and compared with diglycidyl ether of bisphenol A and a plant‐based epoxidized soybean oil bioresin cured with the same curing agent. The higher epoxy value of 1.02, lower viscosity (0.96 Pa s at 25°C), higher mechanical, and higher curing reactivity toward methylhexahydropthalic anhydride of TEIA as compared with epoxidized soybean oil and c...

Itaconic acid, a carbohydrate‐derived aliphatic dicarboxylic acid, is a potential chemical for the synthesis of renewable resource‐based resins and polyesters. Owing to environmental reasons, there is a gradual demand for renewable resources in the chemical industry. Conversely, as a rather underappreciated side effect of this growth, novel chemical building blocks are obtained, which are not commercially derived from petrochemical sources. In this respect, itaconic acid has attracted much attention and its trifunctional structure leads to the synthesis of novel polymeric materials. This review discusses the most relevant information for bio‐based resins and polyesters resulting from itaconic acid and distinctive properties for various commercial applications. © 2017 Society of Chemical Industry

This work aims to synthesize a novel itaconic acid (IA) grafted carboxymethyl chitosan (PICMCS), and further fabricate its nanoparticles for potential biomedical applications. First, PICMCS was prepared via free-radical polymerization of IA monomer, in the presence of ammonium persulfate as an initiator and nitrogen as a protector. Its chemical structure was confirmed by FTIR and (1)H NMR. The IA substitution degree calculated by elemental analysis data was 1.85, implying that IA was successfully grafted to carboxymethyl chitosan (CMCS). XRD and TGA patterns illustrated its well-defined crystallinity and thermostability. Second, PICMCS nanoparticles were fabricated by electrostatic attraction between carboxyl and amino groups in the absence of any additional agent, which were of obvious core-shell structures with an average particle size of 144nm and a polydispersity index of 0.11. PICMCS nanoparticles exhibited excellent physical stability after storage at 25°C for 30 days, without...

Metabolic engineering with a high-yielding mutant, A. terreus AN37, was performed to enhance the production of itaconic acid (IA). Reportedly, the gene cluster for IA biosynthesis is composed of four genes: reg (regulator), mtt (mitochondrial transporter), cad (cis-aconitate decarboxylase), and mfs (membrane transporter). By overexpressing each gene of the IA gene cluster in A. terreus AN37 transformed by the restriction enzyme-mediated integration method, several transformants showing high productivity of IA were successfully obtained. One of the AN37/cad transformants could produce a very high amount of IA (75 g/l) in shake-flask cultivations, showing an average of 5% higher IA titer compared with the high-yielding control strain. Notably, in the case of the mfs transformants, a maximal increase of 18.3% in IA production was observed relative to the control strain under the identical fermentation conditions. Meanwhile, the overexpression of reg and mtt genes showed no significant ...

Studies of Cd (II) complexes with itaconic acid have been carried out by polarographic method in non-aqueous media (20%, 40%, 60% DMF) under varying temperatures, at 298 K and 308 K in presence of KCl as a supporting electrolyte. The reduction of Cd (II) was found to be reversible in nonaqueous medium for itaconic acid ligand and have shown the formation of 1:1, 1:2 and 1:3 complexes. DeFord and Hume's method as modified by Irving has been applied for the determination of composition and stability constant of the complexes species. The changes in thermodynamic parameters H°, G° and S° accompanying complexation have been evaluated. The mathematical Mihailov's method has also been applied for the comparison of stability constant values.

Graft polymerization of itaconic acid on tragacanth gum (TG) was carried out using potassium persulfate as initiator to develop smart hydrogels for drug delivery systems. The effect of the grafting parameters on the degree of grafting was investigated. The grafting was significantly influenced by the reaction medium, the reaction temperature and the monomer concentration. The monomer dependency of the system was found to be 1.52. The hydrogels were characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, differential scanning calorimetry and X‐ray diffraction. The grafted TG had an amorphous nature and exhibited excellent swelling in water and strong dependence on the pH of the medium. The grafted TG showed pH‐dependent release of ciprofloxacin which offers the possibility of using these materials in colon‐specific drug targeting for human healthcare systems. © 2018 Society of Chemical Industry

Nanohydrogel of tragacanth gum using microwave radiations is used for the controlled release of ampicillin. Tragacanth gum was grafted with itaconic acid, employing graft copolymerization in the presence of N, N-methylene-bis-acrylamide (MBA) as cross linker, and potassium persulphate as initiator. The prepared nanohydrogel was characterized using FTIR, XRD, SEM, and TEM. Besides, the hydrogel was evaluated for in vitro drug release in distilled water and different pH values, and antimicrobial efficacy against E. Coli by well diffusion assay. In vitro drug release studies, at different pH values (2.2, 5.4 and 9.4), and distilled water, pH 2.2 was considered as the optimized pH for maximum drug release. Finally, through antimicrobial efficacy studies against E. Coli, it was observed that ampicillin loaded nanohydrogel, was more efficient in comparison to that of plain ampicillin drug.

The bulky 1,4‐cyclohexanedimethanol was used as co‐monomer for introducing rigidity in lipase synthetized poly(itaconate)s. Poly(1,4‐cyclohexanedimethanol itaconate) was synthetized on a 14 g scale at 50 °C, under solvent‐free conditions and 70 mbar using only 135 Units of lipase B from Candida antarctica per gram of monomer. The mild conditions preserved the labile vinyl group of itaconic acid and avoided the decomposition of 1,4‐cyclohexanedimethanol, both observed in chemical polycondensations. Experimental and computational data show that the enzymatic polycondensation proceeds despite the low reactivity of C1 of itaconic acid. The rigid poly(1,4‐cyclohexanedimethanol itaconate) was investigated in the context of aza‐Michael addition of hexamethylenediamine and 2‐phenylethylamine to the vinyl moiety. The enzymatically synthesized linear poly(1,4‐butylene itaconate) was studied as a comparison. The two oligoesters (Molecular Weights ranging from 720 to 2859 g mol−1) reacted on a ...

Itaconic acid, also known as methylene succinic acid, is a colorless, crystalline substance that is found in nature. Due to its two functional carboxylic acid forms and - unsaturated bond, it can be used in a variety of sectors (plastics, super-absorbents, biopolymers, anti-scaling agents, etc.). Itaconic acid can be produced via thermally decarboxylating citric acid, catalysing the condensation of succinic acid derivatives with formaldehyde, decarboxylating aconitic acid, and fermentation utilizing Aspergillus terreus and other microbes. It is quite expensive and harmful to extract itaconic acid from the fermentation broth. In the present study, Iso-butanol, iso-octanol, groundnut, soybean, mustard, and rice bran oil were incorporated as solvents for separating itaconic acid from their solutions in distilled water. Liquid-liquid extraction experiments were conducted over the range of 0.08-0.533 mol.L-1 of itaconic acid. The results thus obtained were defined as the separation effic...

Preparation of Isoniazid (INH) loaded nanogel particles using gamma radiation as safe, simple, cheap and reproducible technique for promoting mycobacterial killing in a lower-dose system aiming in developing of drug resistance. Polymeric pH-sensitive nanogels were prepared by gamma radiation-induced polymerization of Acrylic acid (AAc) or Itaconic acid (IA), in aqueous solution of polyvinylpyrrolidone (PVP), as template polymer. The prepared nanogels were utilized for encapsulation of INH. 3(1)X2(2) factorial design was employed for optimization and exploring the effect of radiation dose (X1) (30-50kGy), ratio of PVP: acid (X2) (50:50-30:70) and type of acid (X3) on the prepared nanogel characterization RESULTS: The optimized levels of X1, X2 and X3 were (50 KGy, 30:70 and Itaconic acid, respectively), with a desirability of 0.959. In-vitro INH release rate from the prepared nanogels decreased with increasing gamma radiation doses, with the predominance of the diffusion mechanism fo...

The water/ACN distributi on coeffi cient o f itaconic acid, fa­ voured for the aqueous phase in creases further on addition of water soluble suspending agents and phase tran sfer catal yst (PTC). The di stributi on coefficient diminishes with rise in te m­ perature. The partiti on coeffi cient is inde pendent of the concen­ trati on of th e solute until saturation in the organic phase and thi s saturati on point shifts to a hi gher concentrati on regime with in ­ crease in te mperature. The differe nti al heat o f solution (t.H) cal­ culated from th e temperature dependency of partition coefficie nt and that fro m th e equilibrium solubilit y of IA in the two phases are practically th e same. t.H value decreases in the presence of water solubl e organic additives, while inorgani c additives increase it marginally.

The rheological behaviour of a dope solution of poly(acrylonitrile-co-itaconic acid) copolymer was compared with that of a poly(acrylonitrile-co-methylacrylate-co-itaconic acid) terpolymer of identical molecular weight. The effects of temperature, concentration and shear force on the rheology of the polymer dope were examined. In both cases, the temperature dependence of zero shear viscosity conformed to the Arrhenius-Frenkel-Eyring equation. The free energy change ΔGv increased with concentration more significantly for the copolymer than the terpolymer. The Power Law model was fitted to the shear dependency of the viscosity, and the pseudoplasticity index (n) decreased with the dope concentration. The shear thinning behaviour was more pronounced for the terpolymer than the copolymer. The decreasing trend of the pseudoplasticity index with concentration and temperature was more pronounced in the case of the terpolymer than the copolymer. Empirical models were arrived at, which could...

The aim of this research is to obtain a composite made of coconut fiber, thermoplastic starch (TPS), ethylene vinyl alcohol (EVOH), and styrene–butadiene copolymer (SBR), achieving the most significant criteria/attribute determined by users. The tools used were quality function deployment (QFD) and the theory of inventive problem solving (TRIZ). The end result indicated that the quality requirement and most representative attribute for users is the toxicity of the material. Four mixtures were made with different percentages of coconut fiber, TPS–EVOH, and SBR, subjecting them to Fourier transform infrared spectroscopy (FTIR), dynamic mechanical analysis (DMA), and thermogravimetric analysis (TGA). The material obtained complies with the requirements of the Food and Drug Administration (FDA) regarding the nontoxicity of synthetic materials (EVOH and SB) to be used in contact with food (packaging and packaging). The spectra IR of the presence of monomers such as methacrylic acid, 2-hy...

SummaryThe functionalization of polypropylene (PP) through the grafting of unsaturated polar monomers such as maleic anhydride (MAH), acrylic acid and its derivatives, in the presence of organic peroxide as initiator, has received much attention over the past decades. However, up to now, only few studies have been reported on the effect of these polar monomers on crystallization and how they are distributed in the polymeric chain. In the present work heterophasic polypropylene copolymer was grafted with itaconic acid (AIt) using reactive extrusion. The main objective of this work was to evaluate the influence of itaconic acid in the rubber and crystalline phases in samples of PP. The separation of the different phases by xylene solubles analysis showed that the acid has preference to incorporate in the rubber fraction. The amount of itaconic acid was determinate by FTIR. It was concluded that the addition of peroxide and itaconic acid to the polymer causes changes of chemical and st...

Itaconic acid (IA) is a well-known bio-based monounsaturated organic acid (C5H6O4), with a white color and crystalline structure. It is widely used in the agro-based, plastics, textile, paint and pharmaceutical sectors, owing to its flexible structure, due to the presence of functional groups with covalent double bonds. IA is an alternative to the petrochemicals acrylic and methacrylic acids. Commercial manufacturing of IA using Aspergillus terreus is more economically effective and feasible, and the Department of Energy (DOE) of the United States added IA under the “top 12” organic chemicals in 2004. This review provides an overview on the synthesis of IA and improvement of its yield by mutagenesis and metabolic engineering of Aspergillus and other fungal strains, along with its wide applications for food, pharmaceutical and textile purposes.