Itaconic anhydride

Base Information

• Chemical Name: Itaconic anhydride
• CAS No.: 2170-03-8
• Deprecated CAS: 141257-20-7,2055573-69-6
• Molecular Formula: C5H4O3
• Molecular Weight: 112.085
• Hs Code.: 2917 19 80
• European Community (EC) Number: 218-518-2
• NSC Number: 43979,43972
• UNII: Y455KS1U7Q
• DSSTox Substance ID: DTXSID8062230
• Nikkaji Number: J38.162D
• Wikipedia: Itaconic_anhydride
• Wikidata: Q15726050
• Metabolomics Workbench ID: 143528
• ChEMBL ID: CHEMBL87967
• Mol file: 2170-03-8.mol

Synonyms:Itaconicanhydride (6CI);Succinic anhydride, methylene- (8CI);Dihydro-3-methylene-2,5-furandione;Itaconicacid anhydride;Methylenesuccinic anhydride;NSC 43979;

Chemical Property of Itaconic anhydride

Chemical Property:

• Appearance/Colour: White to cream crystalline powder
• Melting Point: 66-68 °C(lit.)
• Refractive Index: 1.517
• Boiling Point: 239.4 °C at 760 mmHg
• Flash Point: 114.8 °C
• PSA: 43.37000
• Density: 1.26 g/cm³
• LogP: 0.01610
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Water Solubility.: Hydrolyzes in water.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 112.016043985
• Heavy Atom Count: 8
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

Itaconic Anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C=C1CC(=O)OC1=O
• Uses: Itaconic anhydride is used in immobilization of β-glucosidase. It undergoes estrification to obtain suitable monomers for emulsion polymerization itaconates.

Technology Process of Itaconic anhydride

There total 16 articles about Itaconic anhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-methylenesuccinic acid (97-65-4,25119-64-6) → itaconic acid anhydride (2170-03-8)

Guidance literature:

With trimethylsilylethoxyacetylene; In dichloromethane; at 40 ℃; for 5h;

DOI:10.1021/jo00372a010

Reference yield:

citric acid (77-92-9,906507-37-7) → diethyl 3-hydroxypentanedioate (638-18-6) + Mesaconic acid (498-24-8,7407-59-2) + 1 propene 1,2,3 tricarboxylic acid (499-12-7) + 2-methylenesuccinic acid (97-65-4,25119-64-6) + citraconic acid anhydride (616-02-4) + itaconic acid anhydride (2170-03-8)

Guidance literature:

With Sn/Pb solder; at 150 - 210 ℃;

DOI:10.1366/0003702953963229

Reference yield:

2-methylenesuccinic acid (97-65-4,25119-64-6) → citraconic acid anhydride (616-02-4) + itaconic acid anhydride (2170-03-8)

Guidance literature:

With acetic anhydride; at 80 ℃;

upstream raw materials:

cis-aconitic anhydride

2,6-dioxo-3,6-dihydro-2H-pyran-4-carboxylic acid

1 propene 1,2,3 tricarboxylic acid

2-methylenesuccinic acid

Downstream raw materials:

N-<2-Methoxy-phenyl>-2-methylen-succinamidsaeure

N-Cyclohexyl-2-methylen-succinamidsaeure

N-<4-Methoxy-phenyl>-2-methylen-succinamidsaeure

itaconic acid mono-anilide

Refernces

• 1、 Shlyakhtin, Andrei V.,Lemenovskii, Dmitrii A.,Nifant'Ev, Ilya E.. "Thermal behaviour of the copolymers of acrylonitrile with methyl acrylate and itaconic acid or its derivatives". . p. 277 - 278. Retrieved 2013.
• 2、 Martinez-Garcia, Ariel,Martinez, Ricardo. "Microwave assisted synthesis of diosgenin esters of maleic and itaconic acids". . p. 1917 - 1925. Retrieved 2008.
• 3、 Galanti, Michele C.,Galanti, Anthony V.. "Kinetic Study of the Isomerisation of Itaconic Anhydride to Citraconic Anhydride". . p. 1572 - 1574. Retrieved 1982.
• 4、 Rashed, Md. N.,Siddiki,Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Kon, Kenichi,Toyao, Takashi,Shimizu, Ken-Ichi. "Heterogeneous catalysts for the cyclization of dicarboxylic acids to cyclic anhydrides as monomers for bioplastic production". . p. 3238 - 3242. Retrieved 2017/07/28.