Itaconic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. We manufacture and distribute ita chemically through the isomerization reaction of the citraconic acid. Itaconic acid market size, share, trends, opportunities. Exploration of issatchenkia orientalis as a host for the. Since the middle of the twentieth century, itaconic acid has been produced industrially using the filamentous fungus aspergillus terreus. Polymers of itaconic acid are formed at high conversion by an aqueous polymerization process of partially neutralized monomer solution, water, polyvalent metal ion and initiator. John george haigh, the notorious acid bath murderer in 1940s england, becomes the subject of this dramatization. In this study, di was, for the first time, produced from ia in an aqueous medium by an ionic liquidstrengthened enzymatic method. Anhydrous conditions were observed to minimise the hydrolysis of the anhydride to acid. Itaconic acid a versatile building block for renewable. Chemical product and company identification product name. Dec 08, 2012 itaconic acid is an unsaturated dicarboxylic acid with two pk a values at 3.
We are a premiere supplier and distributor of itaconic. Development of integrated production of polyitaconic acid. Pdf itaconic acid a biotechnological process in change. Itaconic acid 2methylidenebutanedioic acid is an unsaturated dicarbonic acid. Definition a dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group. Files available from the acs website may be downloaded for. Pdf enhancing itaconic acid production by aspergillus terreus. The decarboxylation procedure is also applicable to citric acid, a more widely available bio. The acid is formed from cisaconitate, an intermediate of the tricarboxylic tca cycle, by catalytic action of.
This article presents a complete process chain from wooden. Here, we utilize saccharomyces cerevisiae to enable the synthesis of itaconic acid, a molecule with diverse applications as a petrochemical replacement. Itaconic anhydride ita and stearyl methacrylate sm are other monomers obtained from renewable resources. Itaconic acid definition of itaconic acid by merriamwebster. It has a broad application spectrum in the industrial production of resins and is used as a building block for acrylic plastics, acrylate latexes, superabsorbents, and antiscaling agents willke and vorlop, 2001. Efficient itaconic acid production by aspergillus terreus. Pdf world market and biotechnological production of itaconic acid. Process development of itaconic acid production by a. Metabolic engineering of an acidtolerant yeast strain pichia. Oct 11, 2018 renewable raw materials in sustainable biorefinery processes pose new challenges to the manufacturing routes of platform chemicals. Wed like to understand how you use our websites in order to improve them. It is biodegradable and as such is a sustainable industrial building block. Aconitic acid, the intermediate compound in the pathway from citric acid to itaconic acid was also used successfully as a substrate. Metabolic engineering of an industrial aspergillus niger.
Process optimization by integration of bioconversion with product separation and recovery i. The itaconic anhydride as a derivative of the socalled biobased platform chemical itaconic acid is propagated as a versatile monomer and building block because of its easy accessibility from inexpensive renewable raw materials. Itaconic acid is an unsaturated dicarbonic acid which has a high potential as a biochemical building block, because it can be used as a. In this context, itaconic acid ia or methylene succinic acid 1, fig. The cac intermediate cisaconitate is enzymatically processed by cisaconitate dehycarboxylase cada to produce itaconic acid 68. Expired lifetime application number us853467a inventor messina giuseppe. Itaconic anhydride is the cyclic anhydride of itaconic acid a unsaturated, dicarboxylic acid and is obtained by the pyrolysis of citric acid. That unsaturation makes itaconic acid a possible substitute for acrylic acid as a platform chemical, because it can be polymerized in a similar wayby addition. Expressing the cad gene from aspergillus terreus opened the metabolic pathway towards itaconic acid in a. Production of itaconic acid from acetate by engineering. Itaconic acid is a valueadded organic acid that is widely applied in industrial production. Aspergillus terreus is successfully used for industrial production of itaconic acid. The name itaconic acid was devised as an anagram of aconitic acid, another derivative of citric acid.
Itaconic acid ia, an unsaturated dicarboxylic acid produced by fermentation. Polymerization reactions of itaconic acid and some of its. Aug 17, 2014 itaconic acid methylene succinic acid is produced commercially by microbial fermentation using the fungus a. Us3162582a process for the production of itaconic acid. Itaconic acid definition of itaconic acid by the free. Itaconic acid ita is available as an additive to improve the properties of commodity resin and medium for diverse chemicals. Enhanced itaconic acid production in aspergillus niger using. May 07, 20 itaconic acid is an organic compound that inhibits isocitrate lyase, the key enzyme of the glyoxylate shunt, a pathway essential for bacterial growth under specific conditions. Synthesis and characterization of itaconic anhydride and. Polymers produced according to the process of the invention are useful as detergent additives, scale inhibitors and removers, sequestrants, yarn sizers, deflocculating. Furthermore, it also used for the manufacturing of pulp or paper products, plastic products, plastic additives, various types of paints, and many more.
It can be used in industry as monomer or comonomer in the manufacturing of polymers, and is on the doe department of energy top 12 list of the biotechnologically produced building block chemicals 1,2. As a comonomer in the polymerization of polyacrylonitrile pan to promote the thermooxidative stabilization of polymer. Itaconic acid solubility in water at different temperatures. Itaconic acid ia, also known as methylene succinic acid, is a monounsaturated dicarboxylic acid, with unsaturated double bond and carboxyl functional groups, making it an important intermediate for various organic compounds. Itaconic acid is an unsaturated dicarboxylic acid with two pka values at 3.
Ionic liquidstrengthened immobilized rhizomucor miehei. Itaconic acid market global industry analysis and forecast 2023. Direct production of itaconic acid from liquefied corn starch. Itaconic acid, also known as itaconate, belongs to the class of organic compounds known as branched fatty acids. This dicarboxylic acid is a white solid that is soluble in water, ethanol, and acetone. Itaconic acid ia, or 2methylenesuccinic acid, has a broad spectrum of. Itaconic acid is a dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group. Polyitaconic acid derivatives as thermal stabilizers for. In this respect, itaconic acid has gained considerable attention, as it is biotechnologically produced from carbohydrates on an industrial scale. Itaconic acid revision date 26jan2018 products delayed and immediate effects as well as chronic effects from short and longterm exposure irritation irritating to eyes, respiratory system and skin sensitization no information available carcinogenicity the table below indicates whether each agency has listed any ingredient as a carcinogen. Dimethyl itaconate di, a promising biomassderived intermediate, cannot be synthesized from itaconic acid ia in organisms due to the lack of metabolic pathways. A few other important derivatives include unsaturated ester, 2methyl1, 4butanediol, and 3methyltetrahydrofuran 3methylthf.
Itaconic acid or methylenesuccinic acid, cas 97654 is an unsaturated organic diacid. It is a dicarboxylic acid and an olefinic compound. Preparation and modification of itaconic anhydridemethyl. It can be converted from citric acid by some microorganisms including aspergillus terreus and aspergillus niger. Development of reactive extraction systems for itaconic acid. Aug 27, 2012 aspergillus niger was selected as a host for producing itaconic acid due to its versatile and tolerant character in various growth environments, and its extremely high capacity of accumulating the precursor of itaconic acid. Citeseerx itaconic acid phosphotungstic acid based membranes.
Itaconic acid, or methylidenesuccinic acid, is an organic compound. Itaconic acid distributors bulk chemical supplier for. It is necessary to develop a green and highefficiency method to synthesis di from ia. These acids are used as building blocks for large numbers of compounds, such as resins, paints, plastics, and synthetic fibers acrylic plastic, super absorbants, and antiscaling agents 67. Ita is produced from the pyrolysis of citric acid or through the fermentation of carbohydrates forming itaconic acid followed by its dehydration to form the anhydride 3, and sm is derived from renewable plant oils 46. Review of maleicitaconic acid copolymer purported as. Novel intensified back extraction process for itaconic acid.
Itaconic anhydride ita was prepared by dehydrating itaconic acid with acetyl chloride following an improved previously reported procedure. Stars this entity has been manually annotated by the chebi team. Historically, itaconic acid was obtained by the distillation of citric acid, but currently it is produced by fermentation. Biochemistry of microbial itaconic acid production. Download scientific diagram itaconic acid solubility in water at different temperatures. Buy itaconic acid onlinecas 97654,itaconic acid prices. Poly itaconic acid is the largest derivative segment of the itaconic acid market. Us5336744a process for polymerization of itaconic acid.
Beside the investigations of individual unit operations, the research on process chains, leading from plant biomass to the final products like lactic acid, succinic acid, and itaconic acid is increasing. Here we show that itaconic acid inhibits the growth of bacteria expressing isocitrate lyase, such as salmonella enterica and mycobacterium tuberculosis. Grafting of acrylic acid co itaconic acid onto eptfe and characterization of water uptake by the graft copolymers. Its trifunctional structure allows for the synthesis of new polymers, like polyitaconates or related copolymers which have been extensively studied in the past. Biotechnological production of itaconic acidthings you have to. It has a role as a fungal metabolite and a human metabolite. Pdf the itaconic acid ia world market is expected to exceed 216 million of dollars by 2020 as a result of an. Process engineering of ph tolerant ustilago cynodontis for efficient. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.
Us3056829a process for making itaconic acid esters. For instance, poly itaconic acid, an important derivative of itaconic acid, is produced by the polymerization of itaconic acid monomers. With martin clunes, keeley hawes, richard hope, celia imrie. The acid is typically used as a platform chemical for the production of various valueadded chemicals such as poly itaconic acid, resins biofuel components, ionomer cement, and many more. Itaconic acid production from undetoxified enzymatic. Itaconic acid dictionary definition itaconic acid defined.
Journal of applied polymer science 2015, 2 7, n a n a. Itaconic acid definition is a crystalline dicarboxylic acid c5h6o4 obtained usually by fermentation of sugars with molds genus aspergillus and used as a monomer for polymers and polyesters. Itaconic acid ia global strategic business report 2018. Direct production of itaconic acid from liquefied corn. A series of novel crosslinked poly vinyl alcoholcovinyl acetateco itaconic acid pvaco and phosphotungstic acid pta based organicinorganic composite membranes have been prepared and characterized for direct methanol fuel cell dmfc applications. In combination with acrylamide to form polyacrylamide co itaconicacid to synthesize biodegradable superabsorbent polymers. Production of itaconic and citraconic anhydrides nat. Itaconic acid is an example of a dicarbonic unsaturated acid.
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