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Hexandinitril
1,4-DICYANOBUTANE · HEXANEDINITRILE · adiponitril · ADIPONITRILE · adipylnitrile · Adipicdintrile · Adipodinitrile · Hexanedinitril
Identifikatoren & physikalische Daten
| CAS No. | 111-69-3 |
|---|---|
| Summenformel | C6H8N2 |
| Durchschnittliche Molmasse | 108,14 g/mol |
| Monoisotopische Masse | 108,06874826 g/mol |
| SMILES | N#CCCCCC#N |
| InChIKey | BTGRAWJCKBQKAO-UHFFFAOYSA-N |
| PubChem CID | 8128 |
| ChEMBL | CHEMBL2132938 |
| EC No. | 203-896-3 |
| DTXSID | DTXSID3021936 |
| Lokaler Name | Hexandinitril |
Chemische & physikalische Eigenschaften
| XLogP | -0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 47,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 113 |
| Stoffklassen | Nitrogen Compounds -> NitrilesFlammable agents - 2nd degree |
| SpringerMaterials Properties | Boiling point |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | log Kow= -0.32 |
| Geruch | Practically odorless. |
| Dichte | 0.965 at 68 °F (EPA, 1998) - Less dense than waterwill float0.9676 g/ml @ 20 °CRelative density (water = 1): 0.970.963 @ 20°C0.951 g/mL at 25 °C (lit.) |
| Viscosity | 9.1 cP @ 20 °C2.6 cP @ 70 °C58 mPa*s at 30 °C |
| Color/Form | NEEDLES FROM ETHERColorless liqWater-white, oily liquid |
| Löslichkeit | 50 to 100 mg/mL at 73 °F (NTP, 1992)Sol in alc, chloroformSol in methanol, ethanol, chloroalkanes, and aromatics but has low solubility in carbon disulfide, ethyl ether, and aliphatic hydrocarbons.In water, 8.0X10+4 mg/l @ 20 °C.Solubility in water, g/l at 20 °C: 50-100 (good)4.5%50g/l90 g/L (20 ºC) |
| Flammpunkt | 199.4 °F (EPA, 1998)93 °C200 °F (93 °C) (OPEN CUP)159 °C c.c.199 °F (open cup)(oc) 199 °F163 °C |
| Siedepunkt | 563 °F at 760 mmHg (EPA, 1998)295 °C @ 760 mm Hg295 °C @760 [mm Hg]295 °C (lit.) |
| Decomposition | WHEN HEATED TO DECOMP RELEASES VAPORS CONTAINING HYDROCYANIC ACID.When heated to decomp it emits highly toxic fumes of CN- /cyanides/. |
| Schmelzpunkt | 1-3 °C (lit.) |
| Dampfdichte | 3.7 (vs air) |
| Dampfdruck | 0.01 mm Hg ( 40 °C) |
| Brechungsindex | n20/D 1.438(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Wichte | 0.951 |
| Farbe | Clear colorless to slightly yellow |
| Explosionsgrenze | 7-14%(V) |
| Spezifische Wärmekapazität | Cp(liquid): 1.19 J/(g·K), at 25℃ |
| BRN | 1740005 |
| Henry-Konstante | 1.5×103 mol/(m3Pa) at 25℃, Plyasunov et al. (2006) |
| Dielektrizitätskonstante | 32.5(Ambient) |
| InChI | 1S/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H2 |
| InChIKey | BTGRAWJCKBQKAO-UHFFFAOYSA-N |
| SMILES | N#CCCCCC#N |
| CAS Datenbank | 111-69-3(CAS DataBase Reference) |
| NIST chemische Informationen | Hexanedinitrile(111-69-3) |
| EPA chemische Informationen | Adiponitrile (111-69-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P320, 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 224 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: HexanedinitrileHexanedinitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanedinitrile are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 12-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14296Adiponitrile: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Combustion products may contain hydrogen cyanide (hydrocyanic acid, HCN). Vapor may explode if ignited in an enclosed area. When heated to decomposition, it emits highly toxic fumes. Avoid oxidizing material. Hazardous polymerization may not occur. (EPA, 1998)· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Brandpotenzial | FLAMMABLE WHEN EXPOSED TO HEAT OR FLAME. |
| Gesundheitsgefahren | This material is toxic by ingestion and inhalation. It produces disturbances of the respiration and circulation, irritation of the stomach and intestine, and loss of weight. It is irritating to skin and eyes. (EPA, 1998)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
Anwendungen & Verwendung
Verwenden
Adiponitrile is mainly used in the production of hexamethylenediamine for manufacturing nylon 6,6. Lesser uses include that in organic synthesis and in the preparation of adipoguanamine, which is used as an extractant for aromatic hydrocarbons. This chemical is an important intermediate for the manufacture of synthetic fiber.
Herstellung & Synthese
synthetische
The main method of industrial production of adiponitrile is the amination of adipic acid. Adipic acid and excess ammonia are reacted in the presence of catalyst phosphoric acid or its salts or esters at a temperature of 270-290°C to generate diammonium adipate, which is then heated and dehydrated to generate crude adiponitrile, The product is obtained by rectification.