Dibutylcarbonat
DI-N-BUTYL CARBONATE · BUTYL CARBONATE · n-Butyl carbonate · Dibutyl carbonate · n-C4H9OC(O)OC4H9-n · Carbonic acid dibutyl · carbonicaciddibutylester · Carbonicacid,dibutylester
Identifikatoren & physikalische Daten
| CAS No. | 542-52-9 |
|---|---|
| Summenformel | C9H18O3 |
| Durchschnittliche Molmasse | 174,24 g/mol |
| Monoisotopische Masse | 174,12559444 g/mol |
| SMILES | CCCCOC(=O)OCCCC |
| InChIKey | QLVWOKQMDLQXNN-UHFFFAOYSA-N |
| PubChem CID | 68333 |
| EC No. | 208-816-0 |
| DTXSID | DTXSID7060255 |
| Lokaler Name | Dibutylcarbonat |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 35,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 100 |
| SpringerMaterials Properties | Optical coefficient |
| Schmelzpunkt | <25 °C |
| Siedepunkt | bp 206.6° |
| Dichte | d420 0.9251d425 0.9388 |
| Brechungsindex | nD20 1.4117 |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | clear liquid |
| Farbe | Colorless to Almost colorless |
| InChI | InChI=1S/C9H18O3/c1-3-5-7-11-9(10)12-8-6-4-2/h3-8H2,1-2H3 |
| InChIKey | QLVWOKQMDLQXNN-UHFFFAOYSA-N |
| SMILES | C(OCCCC)(=O)OCCCC |
| EPA chemische Informationen | Carbonic acid, dibutyl ester (542-52-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.2% (3 of 137) of reports.DangerH315 (13.9%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 137 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 24-08-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23934Carbonic acid, dibutyl ester: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (13.9%) |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2920.90.5100 |
Anwendungen & Verwendung
Verwenden
Dibutyl Carbonate is a potential fuel substitute due to the observed decrease in CO2 emissions. Also used in CO2 catalytic activation.
Herstellung & Synthese
synthetische
A 160 mL Parr autoclave was charged with butanol 982 (2.22 g, 0.03 mol), N-cyclohexyl-N',N',N'',N''-tetramethylguanidine (CyTMG; 6.9 g, 0.035 mol), and acetonitrile (30 mL). The autoclave was attached to a pressure head, and 160 psig CO2 was introduced with stirring at room temperature. An exothermic reaction ensued, leading to an increase in temperature to ca. 40℃. In a Fischer–Porter bottle was placed a solution of 1-chlorobutane (8.33 g, 0.09 mol) in acetonitrile (10 mL). This bottle was attached to a pressure head, and 80 psig CO2 was introduced above the solution. After 1 h, the solution of 1-chlorobutane was added in one portion under 80 psig CO2 to the pre-formed carbonate anion solution generated in the autoclave. After the addition, the pressure was increased to 160 psig with CO2, and the reaction mixture was warmed to 85 ℃ for 16 h. Thereafter, the reaction mixture was allowed to cool to room temperature, and then the pressure was released. An aliquot was removed, diluted with diethyl ether, and CyTMGH+Cl- was filtered off; by GC analysis using biphenyl as an internal standard, the yield of dibutyl carbonate was calculated as 73%; oil.