Succinimid
SI · Pyrrolidine-2,5-dione · 2,5-PYRROLIDINEDIONE · 3,4-Dihydropyrrole-2,5-dione · Lubrizol 2153 · succiminide · Succinic imide · Orotric
Identifikatoren & physikalische Daten
| CAS No. | 123-56-8 |
|---|---|
| Summenformel | C4H5NO2 |
| Durchschnittliche Molmasse | 99,09 g/mol |
| Monoisotopische Masse | 99,0320284 g/mol |
| SMILES | O=C1CCC(=O)N1 |
| InChIKey | KZNICNPSHKQLFF-UHFFFAOYSA-N |
| PubChem CID | 11439 |
| ChEMBL | CHEMBL275661 |
| ChEBI | CHEBI:9307 |
| EC No. | 204-635-6 |
| DTXSID | DTXSID8051629 |
| Lokaler Name | Succinimid |
Chemische & physikalische Eigenschaften
| XLogP | -1 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 105 |
| Stoffklassen | Industrial compound |
| SpringerMaterials Properties | Boiling point |
| Schmelzpunkt | 123-125 °C (lit.) |
| Siedepunkt | 285-290 °C (lit.) |
| Dichte | 1.41 |
| Dampfdruck | <1 hPa (50 °C) |
| Brechungsindex | 1.4166 (estimate) |
| Flammpunkt | 201 °C |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | 330g/lSoluble in water and ethanol. Insoluble in ether and chloroform. |
| pKa (Säurekonstante) | 9.6(at 25℃) |
| Aggregatzustand | Powder or Flakes |
| Farbe | Off-white to beige to light brown |
| pH | 4-6 (200g/l, H2O) |
| Geruch | nearly odorless |
| Merck | 14,8871 |
| BRN | 108440 |
| InChI | 1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7) |
| InChIKey | KZNICNPSHKQLFF-UHFFFAOYSA-N |
| SMILES | O=C1CCC(=O)N1 |
| LogP (Verteilungskoeffizient) | -0.85 at 20℃ |
| CAS Datenbank | 123-56-8(CAS DataBase Reference) |
| NIST chemische Informationen | 2,5-Pyrrolidinedione(123-56-8) |
| EPA chemische Informationen | Succinimide (123-56-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 33.2% (120 of 361) of reports.WarningH315 (66.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 361 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-PyrrolidinedioneStatus: Active Update: 18-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/301682,5-Pyrrolidinedione: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (66.5%) |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29251995 |
| RTECS-Nr. | WN2200000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in rats: 14 g/kg (Melon) |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 22-24/25-36-26-S24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Succinimide is used in organic syntheses and in industrial silver plating processes. It is a reagent that is used in the synthesis of Lumiflavin (L473900), which is a toxic photolysis product of vitamin B2 (R415000). Further, it is used to form covalent bonds between proteins, peptides and plastics. In addition to this, it is used as an important raw material for the synthesis of heterocyclic compounds through N-acyliminium cyclizations.
Herstellung & Synthese
synthetische
To a flask equipped with a dropping funnel, mechanical stirrer, and a 40 cm long side arm of not less than 10 mm inside diameter is added 236 gm (2.0 mole) of succinic acid. The flask is cooled and 270 ml (4.0 moles) of 28% aqueous ammonia is slowly added with stirring. The flask is rapidly heated with an oil bath until 200 ml of water distils. The temperature of the bath is rapidly raised to 275°C. Succinimide starts to distil over the range 275-289°C, to afford 168 gm of crude product which solidifies on cooling. The intermediate fraction, boiling between 102° and 275°C, is redistilled to afford 10.0 gm of crude succinimide, b.p. 275-289°C. The combined product (178 gm) is added to 178 gm of hot ethanol. The solution is cooled, the crystals filtered, washed with 25 ml of cold ethanol, and dried to afford 163-164 gm (82-83%), m.p. 123-125°C. Approximately 4-5 gm of additional product may be obtained by concentrating the mother liquor. Recent Japanese patents suggested inert aprotic solvents such as cyclic amides (e.g., N-methylpyrrolidone, N-acetyl-2-pyrrolidone, DMF, or tet-ramethylurea) and azeotroping solvents (e.g., toluene, 0-xylene, hexane, or pentane) or other high-boiling solvents (e.g., chlorobenzene or chlo-rotoluene) as dehydrating agents for the formation of imides from dibasic acids (e.g., 3- and/or 4) hydroxyphthalic acid with a large variety of diamines including diaminosiloxanes such as bis (3-aminopropyl)-tetra-methylsiloxane.