Itaconsureanhydrid
2,5-Furandione, dihydro-3-methylene- · 3-Methylenedihydrofuran-2,5-dione · ITACONIC ANHYDIDE · ITACONIC AHYDRIDE · ITACONIC ANHYDRIDE · ItaconicAnhydride>Itaconic anhydride,98% · Itaconic anhydride 95% · Itaconic acid anhydride
Identifikatoren & physikalische Daten
| CAS No. | 2170-03-8 |
|---|---|
| Summenformel | C5H4O3 |
| Durchschnittliche Molmasse | 112,08 g/mol |
| Monoisotopische Masse | 112,01604399 g/mol |
| SMILES | C=C1CC(=O)OC1=O |
| InChIKey | OFNISBHGPNMTMS-UHFFFAOYSA-N |
| PubChem CID | 75110 |
| ChEMBL | CHEMBL87967 |
| EC No. | 218-518-2 |
| DTXSID | DTXSID8062230 |
| Lokaler Name | Itaconsureanhydrid |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 169 |
| Polymers | Plastics & Rubber -> Acid Anhydrides, Cyclic |
| SpringerMaterials Properties | Chemical shift |
| Physical Description | Off-white or white crystalline powder[Alfa Aesar MSDS] |
| Schmelzpunkt | 66-68 °C (lit.) |
| Siedepunkt | 114-115 °C/12 mmHg (lit.) |
| Dichte | 1.2600 |
| Brechungsindex | 1.5130 (estimate) |
| Flammpunkt | 114-115°C/12mm |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Crystalline Powder |
| Farbe | White to cream |
| Löslichkeit | Hydrolyzes in water. |
| BRN | 2212 |
| InChI | InChI=1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h1-2H2 |
| InChIKey | OFNISBHGPNMTMS-UHFFFAOYSA-N |
| SMILES | O1C(=O)CC(=C)C1=O |
| CAS Datenbank | 2170-03-8(CAS DataBase Reference) |
| NIST chemische Informationen | 2,5-Furandione, dihydro-3-methylene-(2170-03-8) |
| EPA chemische Informationen | 2,5-Furandione, dihydro-3-methylene- (2170-03-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (83.3%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 2,5-Furandione, dihydro-3-methylene-Status: Active Update: 03-02-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/189592,5-Furandione, dihydro-3-methylene-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Hydrolyzed by waterAn irritant[Alfa Aesar MSDS] See ACID ANHYDRIDES. |
| Hazard Classes and Categories | Acute Tox. 4 (83.3%) |
| F | 3-10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2917 19 80 |
| R-Sätze (R) | 36/37/38-22 |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 26-36-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
Itaconic anhydride is used in immobilization of β-glucosidase. It undergoes estrification to obtain suitable monomers for emulsion polymerization itaconates.
Herstellung & Synthese
synthetische
To a flask equipped with a 12 mm diameter ground glass adaptor tube bent for downward distillation and joined to a 100 cm condenser is added 200 gm (0.95 mole) of citric acid monohydrate. An ice-cooled flask and a cold trap are connected to the condenser. The flask containing the citric acid is heated rapidly with a wide flame of the Meker burner so that in 12-15 min the distillation at 175-190°C is complete. The distillation is stopped earlier if the vapors in the reaction flask become yellow. Superheating of the citric acid will cause rearrangement to citraconic anhydride. The water is quickly separated from the distillate and the itaconic anhydride layer dried to afford 40-50 gm (37-47%), m.p. 67-68°C. Long time contact of the water with the anhydride causes it to hydrolyze to itaconic acid, m.p. 162-165°C.