Hexamethylen-1,6-diisocyanat
HDI · HMDI · 1,6-Diisocyanatohexane · 1,6-HEXAMETHYLENE DIISOCYANATE · H6XDI · Hexane, 1,6-diisocyanato- · Hexamethylene-1,6-diisocyanate · 1,6-diisocyanated’hexamethylene
Identifikatoren & physikalische Daten
| CAS No. | 822-06-0 |
|---|---|
| Summenformel | C8H12N2O2 |
| Durchschnittliche Molmasse | 168,19 g/mol |
| Monoisotopische Masse | 168,08987763 g/mol |
| SMILES | O=C=NCCCCCCN=C=O |
| InChIKey | RRAMGCGOFNQTLD-UHFFFAOYSA-N |
| PubChem CID | 13192 |
| ChEMBL | CHEMBL1896533 |
| ChEBI | CHEBI:53578 |
| EC No. | 212-485-8 |
| DTXSID | DTXSID4024143 |
| Lokaler Name | Hexamethylen-1,6-diisocyanat |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 58,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 169 |
| Schmelzpunkt | -55°C |
| Siedepunkt | 82-85 °C/0.1 mmHg |
| Dichte | 1.047 g/mL at 20 °C (lit.) 1.047 g/mL at 20 °C |
| Dampfdruck | 0.05 mm Hg ( 25 °C) |
| Brechungsindex | n20/D 1.453 |
| Flammpunkt | 248 °F |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Wichte | 1.05 |
| Farbe | Clear colorless to slightly yellow |
| Explosionsgrenze | 0.9-9.5%(V) |
| Löslichkeit | Reacts |
| BRN | 956709 |
| Stabilität | Stable. Moisture sensitive. Combustible. Incompatible with strong oxidizing agents, strong bases, amines, acids. May react explosively with alcohols in the presence of base without a diluting solvent. Heating above 200 C may cause polymerization. |
| InChI | 1S/C8H12N2O2/c11-7-9-5-3-1-2-4-6-10-8-12/h1-6H2 |
| InChIKey | RRAMGCGOFNQTLD-UHFFFAOYSA-N |
| SMILES | O=C=NCCCCCCN=C=O |
| LogP (Verteilungskoeffizient) | 3.2 at 20℃ |
| CAS Datenbank | 822-06-0(CAS DataBase Reference) |
| NIST chemische Informationen | 1,6-Hexamethylene diisocyanate(822-06-0) |
| EPA chemische Informationen | Hexamethylene-1,6-diisocyanate (822-06-0) |
Sicherheit & Vorschriften
| F | 10-19-21 |
|---|---|
| Berufliche Expositionsstufe (OEB) | D |
| Arbeitsplatzgrenzwert (OEL) | TWA: 0.005 ppm (0.035 mg/m3), Ceiling: 0.020 ppm (0.140 mg/m3) [10-minute] |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2281 |
| Zollcode | 29291090 |
| RTECS-Nr. | MO1740000 |
| R-Sätze (R) | 23-36/37/38-42/43-41-34-26-22-39/23/24/25-23/24/25-11 |
| Toxizität | LD50 orally in Rabbit: 746 mg/kg LD50 dermal Rabbit 570 mg/kg |
| Gefahrensymbole | T,T+,F |
| Sicherheitshinweise (S) | 26-28-38-45-28A-36/37/39-23-36/37-16-7 |
| Gefahrenklasse | 6.1Acute Tox. 1 InhalationAcute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1CSkin Sens. 1STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Gefahrstoffdaten | 822-06-0(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 454 °C |
Anwendungen & Verwendung
Beschreibung
This diisocyanate compound is used in the manufacture of various polyurethane products: elastic and rigid foams, paints, lacquers, adhesives, bin ding agents, synthetic rubbers, and elastomeric fibers.
Verwenden
Hexamethylene diisocyanate (HDI) is one of the most common aliphatic disocyanates, It is a monomer used in the production of polyurethane foams and exceptionally high-quality coatings, and is found in some industrial paints and spray painting operations. It is a compound which reacts readily with water and alcohols (Von Burg 1993). It has a vapor pressure of 0.05 mm Hg at room temperature, but can be present in aerosol form allowing a potentially higher exposure to individuals. The HDI-BT trimer is often present for similar industrial uses. It would be expected to have a lower vapor pressure; however, the aerosol form can also be present, allowing potentially higher exposure of HDI-BT to individuals. Hexamethylene diisocyanate reacts slowly with water to form carbon dioxide (HSDB 1996). The base-catalyzed reaction of Hexamethylene diisocyanate with alcohols should be carried out in inert solvents; the reaction may occur with explosive violence in the absence of solvents (NFPA 1994).
Herstellung & Synthese
synthetische
Hexamethylene diisocyanate (HDI) is prepared by the phosgenation of hexamethylenediamine (section lO.2.2(b)): H2N-(CH2)6-NH2--COCl2-->OCN-(CH2)6-NCOHexamethylene diisocyanate is a liquid with a volatility of the same order as that of tolylene diisocyanate. It is respiratory irritant and also has powerful effects on the skin and eyes. Hexamethylene diisocyanate was one of the first diisocyanates utilized for making polyurethanes, being used to prepare fibres and moulding compounds. These applications are no longer of importance but hexamethylene diisocyanate now finds use mainly in coatings which are more light stable than those based on aromatic isocyanates.