Diethyl ether or ethoxyethane is a colorless, highly flammable and volatile liquid that is commonly used as a solvent and as a starting material for the synthesis of other organic compounds.
| IUPAC Name | Ethoxyethane |
| Molecular Formula | C4H10O |
| CAS Number | 60-29-7 |
| Synonyms | Ether, Ethyl ether, Ethyl oxide, Diethyl oxide, 1,1′-Oxybisethane, Dether, Anesthetic ether, Sulfuric ether, Etylowy eter |
| InChI | InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 |
Diethyl ether Properties
Diethyl ether density g/ml
The density of diethyl ether is 0.713 g/mL. Density is defined as the mass of a substance per unit volume. In the case of diethyl ether, its density is lower than that of water, which has a density of 1 g/mL. This means that diethyl ether floats on top of water.
Diethyl ether molar mass
Diethyl ether has a molar mass of 74.12 g/mol. Molar mass is the mass of one mole of a substance, expressed in grams. In the case of ethoxyethane, one mole of the compound contains 74.12 grams of it. This value is derived from the atomic masses of carbon, hydrogen, and oxygen that make up the molecule. The molar mass of a substance is an important parameter in chemical calculations, as it is used to determine the amount of substance present in a given sample.
Diethyl ether Structure
Diethyl ether has a simple chemical structure consisting of two ethyl groups attached to an oxygen atom. The molecule has a bent shape due to the lone pair of electrons on the oxygen atom that causes a distortion of the molecule from the ideal tetrahedral geometry. The bent structure of ethoxyethane is responsible for its ability to form hydrogen bonds with other molecules, making it a useful solvent.
Diethyl ether boiling point
The boiling point of diethyl ether is 34.6 °C (94.3 °F). Boiling point is the temperature at which a substance changes from its liquid state to its gaseous state at atmospheric pressure. Diethyl ether has a relatively low boiling point, making it a volatile liquid that easily evaporates at room temperature. This property makes it useful as a solvent and as an anesthetic in medicine.
Diethyl ether melting point
The melting point of ethoxyethane is -116.3 °C (-177.3 °F). Melting point is the temperature at which a solid substance changes to a liquid state at atmospheric pressure. Ethoxyethane is a colorless liquid at room temperature, and it is rare to see it in a solid state due to its low melting point.
Diethyl ether molecular weight
Ethoxyethane has a molecular weight of 74.12 g/mol. Molecular weight is the sum of the atomic weights of all atoms in a molecule. It is an important parameter in chemical reactions and stoichiometry as it determines the amount of reactant needed to form a specific amount of product.
Diethyl ether formula
The chemical formula of ethoxyethane is C4H10O. It is composed of four carbon atoms, ten hydrogen atoms, and one oxygen atom. The formula represents the exact number of each type of atom in a molecule and is used to determine the molecular weight of the substance. The chemical formula of a substance is essential in chemical equations, where it is used to balance reactions and determine the amount of reactants and products.
| Appearance | Colorless liquid |
| Specific Gravity | 0.713 |
| Color | Colorless |
| Odor | Sweet, ether-like |
| Molar Mass | 74.12 g/mol |
| Density | 0.713 g/mL |
| Melting Point | -116.3 °C (-177.3 °F) |
| Boiling Point | 34.6 °C (94.3 °F) |
| Flash Point | -45 °C (-49 °F) |
| Water Solubility | 6.9 g/L at 25 °C |
| Solubility | Miscible in most organic solvents |
| Vapor Pressure | 440 mmHg at 25 °C |
| Vapor Density | 2.5 |
| pKa | 15.9 |
| pH | 7 (neutral) |
Diethyl ether Safety and Hazards
Ethoxyethane has several safety and hazard considerations that must be taken into account when handling it. It is highly flammable and can form explosive vapor-air mixtures. Therefore, it must be kept away from sources of ignition and sparks. It can also cause irritation to the skin, eyes, and respiratory system, and prolonged exposure can cause dizziness and headaches. Proper ventilation is necessary when using ethoxyethane, and protective equipment such as gloves and goggles should be worn. It should also be stored in a cool, dry place away from oxidizing agents and incompatible materials.
| Hazard Symbols | F, Xi |
| Safety Description | S9, S16, S29, S33, S60, S61 |
| UN IDs | UN 1155 |
| HS Code | 2909.19.00 |
| Hazard Class | 3 |
| Packing Group | II |
| Toxicity | LD50 (oral, rat): 3,500 mg/kg |
Diethyl ether Synthesis Methods
Various methods exist to synthesize diethyl ether, including the reaction of ethanol with sulfuric acid and the dehydration of ethanol using a dehydrating agent like sulfuric acid or alumina.
To synthesize ethoxyethane via the dehydration method, heat ethanol with a dehydrating agent like sulfuric acid or alumina to remove a molecule of water, thus forming ethoxyethane. To enhance the reaction yield, one can use a catalyst such as potassium hydroxide or sodium hydroxide.
Another method of synthesizing ethoxyethane is through the Williamson ether synthesis, where ethanol reacts with an alkoxide ion such as sodium ethoxide to form ethoxyethane. This reaction requires the use of a strong base and an appropriate solvent, such as anhydrous ethanol.
Another method to produce ethoxyethane is through the Tishchenko reaction. In this process, acetic acid and ethanol react in the presence of a catalyst like sulfuric acid or aluminum oxide, resulting in a high yield of ethoxyethane.
To produce ethoxyethane as a final product, one can use sodium borohydride or sodium amalgam to reduce acetaldehyde. This is another method to synthesize ethoxyethane. This reaction results in the formation of ethanol, which can then undergo the dehydration method described above to form ethoxyethane.
Diethyl ether Uses
Some uses of diethyl ether include:
- Solvent: A highly effective solvent for a range of organic compounds, including oils, fats, resins, and waxes. Used in the production of lacquers, varnishes, and other coatings.
- Anesthetic: Used as an anesthetic for surgical procedures, though it has largely been replaced by safer alternatives in modern medicine.
- Extraction: Used as an extraction solvent in the production of pharmaceuticals, natural products, and essential oils.
- Fuel additive: Used as a fuel additive to improve the performance of diesel engines, as it can increase the cetane number of the fuel.
- Chemical intermediate: Key intermediate in the production of a range of organic compounds, including ethanol, acetaldehyde, and acetic acid.
- Flavoring agent: Used as a flavoring agent in the production of some foods and beverages, such as candy and liqueurs.
- Laboratory reagent: Used as a reagent in laboratory experiments, particularly in organic chemistry.
- Aerosol propellant: Used as a propellant in aerosol products. Safety concerns have led to the phasing out of this use.
Questions:
Q: Is diethyl ether polar?
A: Yes, ethoxyethane is a polar molecule due to the presence of the oxygen atom, which creates a partial negative charge on one end of the molecule and a partial positive charge on the other end.
Q: Is diethyl ether miscible in water?
A: Ethoxyethane is not very soluble in water. However, it is considered to be partially miscible in water, meaning that it can mix with water to some extent but not completely.
Q: Is diethyl ether flammable?
A: Yes, ethoxyethane is highly flammable and can form explosive mixtures with air.
Q: Is diethyl ether polar or nonpolar?
A: Ethoxyethane is a polar molecule due to the presence of the oxygen atom.
Q: Is diethyl ether polar aprotic?
A: Yes, ethoxyethane is considered to be a polar aprotic solvent, meaning that it can dissolve polar molecules but does not have a hydrogen atom that can act as a hydrogen bond donor.