Itaconic acid
- Methyl succinate
- Methylenbutandisäure
- Itaconic acid
White, flammable, hygroscopic, nearly odorless powder
Fixed
1.63 g · cm -3
162-167 ° C
Unknown as from 268 ° C using the decomposition
3.84 and 5.55
Moderately in water ( 83 g · l-1 at 20 ° C)
Attention
2969 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
Itaconic acid ( C5H6O4 ) is an organic dicarboxylic acid. It is formed as one of three products in the distillation of citric acid. Itaconic acid is soluble in water, ethanol and acetone.
Properties
Itaconic acid occurs at normal temperature in the solid state as a white, almost odorless powder. The molar mass is 130.10 g · mol -1 with a density of 1.63 g · cm -3. It is flammable and hygroscopic and moderately soluble in water (83 g · l-1 at 20 ° C).
Production and representation
The technical production of itaconic acid is carried out by submerged fermentation of molasses biotechnology and other substrates with strains of the fungi Aspergillus itaconicus or Aspergillus terreus. This is done theoretically with use of a 15 % sucrose solution, a conversion of 78 % to itaconic acid. The amount of sugar-based production is more than 80 g / l
The metabolic pathway for the first time in 1931 (now Aspergillus itaconicus ) and shortly thereafter demonstrated Aspergillus niger for Aspergillus terreus. Itaconic acid forms as a byproduct of the citric acid cycle in the reaction of citric acid (citrate) to isocitric acid ( isocitrate ) via cis- aconitic acid. The cis- aconitic acid is to be for the production of itaconic acid decarboxylated ( so it will be deprived of CO2 ) rather than by the addition of water hydrated to isocitric acid. As an enzyme for the reaction of itaconic acid to the cis - aconitic acid decarboxylase is used. An alternative pathway runs from the pyruvic acid ( pyruvate ) via Citratäpfelsäure, citraconic acid and itaconic acid Itaweinsäure to.
Byproducts succinic acid and Itaweinsäure, which are undesirable in the industrial process. The formation can be by the addition of calcium, which inhibits the Itakonsäureoxidase prevented.
Use
The total amount of global production of itaconic acid amounts to more than 80,000 tons per year at a market price of about 2 U.S. $ / kg ( as of 2009).
Itaconic acid is used as a comonomer in the synthesis of polyacrylates and gum arabic. Furthermore, it is used in the manufacture of paints and coatings, as thickeners for greases, for pharmaceuticals, as a herbicide, and biodegradable polymers in the packaging industry.
Together with other biotechnologically relevant chemicals itaconic acid was identified by the Department of Energy of the USA as one of twelve platform chemicals with particular biotechnological production potential in 2004. However, in a critical review of the list of 2010, it was not taken up again in the list of the resulting ten hopefuls due to various criteria.