Itaconic acid Chemical Properties

Melting point:

165-168 °C (lit.)

Boiling point:

268°C

Density 

1.573 g/mL at 25 °C (lit.)

vapor pressure 

0.0000115 Pa (20 °C)

refractive index 

1.4980 (estimate)

Flash point:

268°C

storage temp. 

Store below +30°C.

solubility 

77.49g/l

form 

Crystalline Powder or Crystals

pka

3.85(at 25℃)

Specific Gravity

1.573

color 

White to light beige

PH

3.5(1 mM solution);2.95(10 mM solution);2.43(100 mM solution);

Odor

Characteristic Odor

Water Solubility 

Soluble in water, acetone, methanol, hexane and ethanol. Slightly soluble in benzene, chloroform, carbon disulfide and petroleum ether.

Sensitive 

Hygroscopic

Merck 

14,5242

BRN 

1759501

Stability:

Light Sensitive

InChIKey

LVHBHZANLOWSRM-UHFFFAOYSA-N

LogP

-0.301 at 20℃

CAS DataBase Reference

97-65-4(CAS DataBase Reference)

NIST Chemistry Reference

Butanedioic acid, methylene-(97-65-4)

EPA Substance Registry System

Itaconic acid (97-65-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

1

Autoignition Temperature

430 °C

TSCA 

Yes

HS Code 

29171990

Hazardous Substances Data

97-65-4(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 2000 mg/kg

MSDS

• Language:English Provider:Methylenebutanedioic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Itaconic acid Usage And Synthesis

Discovery

Itaconic acid was discovered by Baup in 1837 as a product of the pyrolytic distillation of citric acid. The name itaconic was devised as an anagram of aconitic. Itaconic acid is formed in the fermentation of some sugars. In 1929, Kinoshita first showed the acid as a metabolic product of Aspergillus itaconicus.

Source

Itaconic acid is formed by the cytosolic enzyme aconitate decarboxylase from cis-aconitic acid. Another biosynthetic pathway from pyruvate through citramalic acid, citraconic acid, and itartaric acid also results in itaconic acid.

Chemical Properties

white to light beige crystalline powder

Uses

The major uses for itaconic acid are in copolymerizations, resins, plasticizers, and as lube oil additives.

Uses

Itaconic acid is used in the preparation of acrylonitrile-butadiene-styrene and acrylate latexes. It is also used to prepare poly-itaconic acid, resins biofuel components and ionomer cements. It finds application in the textile, chemical and pharmaceutical industries. It is also used as an additive in fibers and ion exchange resins to increase abrasion, waterproofing, physical resistance, dying affinity and better duration. Further, it acts as a co-monomer used in the preparation of acrylic fibers and rubbers, reinforced glass fiber, artificial diamonds and lens. In addition to this, it acts as a binder and sizing agent in non-weaving fibers.

Definition

ChEBI: A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.

Definition

itaconic acid: A product of the fermentationof the flamentous fungusAspergillus niger. Itaconic acid is usedcommercially in the production ofadhesives and paints.

General Description

Itaconic acid, an unsaturated dicarbonic organic acid, is a metabolic product of Aspergillus itaconicus.

Flammability and Explosibility

Non flammable

Purification Methods

Crystallise itaconic acid from EtOH, EtOH/water or EtOH/*benzene. [Beilstein 2 IV 2228.]

Itaconic acid(97-65-4)Related Product Information

• Dimethyl succinate
• Ethyl 2-(Chlorosulfonyl)acetate
• Citric acid
• Folic acid
• Ammonium succinate
• Dioctyl sulfosuccinate sodium salt
• Disodium succinate
• Metroprolol succinate
• meso-2,3-Dibromosuccinic acid
• Glycine
• ITACONIC ACID DIMETHYL ESTER
• DL-Phenylsuccinic acid
• iron succinate
• Succinic acid
• CIS-ACONITIC ACID
• ITACONIC ACID DI-N-BUTYL ESTER (STABILIZED WITH HQ) 95+%,ITACONIC ACID DI-N-BUTYL ESTER,ITACONIC ACID DIBUTYL ESTER
• Itaconic acid anhydride
• Maleic acid