Decalin
| Names | |
|---|---|
| IUPAC name
Decahydronaphthalene
| |
| Other names
Bicyclo[4.4.0]decane
Decaline | |
| Properties | |
| C10H18 | |
| Molar mass | 138.25 g/mol |
| Appearance | Colorless liquid |
| Odor | Aromatic |
| Density | 0.896 g/cm3 |
| Melting point | trans: −30.4 °C (−22.7 °F; 242.7 K) cis: −42.9 °C (−45.2 °F; 230.3 K) |
| Boiling point | trans: 187 °C (369 °F; 460 K) cis: 196 °C (384 °F; 469 K) |
| 0.089 mg/100 ml (25 °C) | |
| Solubility | Miscible with acetone, benzene, chloroform, diethyl ether, DMSO, ethanol, ethyl acetate, heptane, hexane, isopropanol, methyl ethyl ketone, methanol, propanol, pyridine, toluene, xylene Slightly soluble in glacial acetic acid |
| Vapor pressure | 2.3 mmHg at 25 °C |
| Hazards | |
| Safety data sheet | Sigma-Aldrich (cis) Sigma-Aldrich (trans) Sigma-Aldrich (mixture) |
| Flash point | 57 °C (135 °F; 330 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
4.170 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Naphthalene Tetralin |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Decalin, also known as decahydronaphthalene is a bicyclic organic compound, used as laboratory and industrial solvent. It has the chemical formula C10H18.
Decalin occurs in cis and trans forms. The trans form is energetically more stable because of fewer steric interactions. cis-Decalin is a chiral molecule without a chiral center; it has a two-fold rotational symmetry axis, but no reflective symmetry. However, the chirality is canceled through a chair-flipping process that turns the molecule into its mirror image.
Contents
Properties
Chemical
Oxygenation of decalin give the tertiary hydroperoxide, which rearranges to cyclodecenone, a precursor to sebacic acid.
Physical
Decalin is a colorless liquid, immiscible with water, but miscible with many organic solvents. It has an aromatic odor described as being close to menthol, but different from tetralin or naphthalene.
Availability
Decalin is sold by chemical suppliers.
Preparation
Complete hydrogenation of naphthalene or tetralin in the presence of platinum or nickel catalyst yields decalin.
Projects
- Solvent for heavy aromatic compounds
- Moieties in transition-metal complex catalysts
Handling
Safety
Decalin is irritant and should be handled with care. With a flash point of 57 °C, it is not very flammable and unless heated prior, it doesn't pose a serious fire hazard.
Storage
In closed air-tight bottles. Since it is known to form peroxides in contact upon prolonged contact with air, it's best to test it for peroxides every few months. These peroxides are dangerous upon concentration, since they can explode. Sodium metal can be added to chemically destroy the peroxides.
Disposal
Should be mixed with a more flammable solvent and burned.
