Sodium ethoxide is a strong base formed by reacting sodium with ethanol. It is used in organic synthesis to facilitate reactions such as esterification and deprotonation.
| IUPAC Name | Sodium ethoxide |
| Molecular Formula | C2H5NaO |
| CAS Number | 141-52-6 |
| Synonyms | Ethanol, sodium salt; Sodium ethylate; Ethyl sodium; Ethylate; Sodium ethyl alcoholate |
| InChI | InChI=1S/C2H5O.Na/c1-2-3;/h2-3H,1H3;/q-1;+1 |
Sodium Ethoxide Properties
Sodium Ethoxide Formula
The chemical formula of sodium ethylate is C2H5NaO. It consists of two carbon atoms (C), five hydrogen atoms (H), one sodium atom (Na), and one oxygen atom (O). The formula represents the ratio of atoms present in a molecule of sodium ethylate.
Sodium Ethoxide Molar Mass
The molar mass of sodium ethylate is calculated by summing up the atomic masses of all the atoms in its formula. Sodium (Na) has a molar mass of 22.99 g/mol, carbon (C) has a molar mass of 12.01 g/mol, hydrogen (H) has a molar mass of 1.01 g/mol, and oxygen (O) has a molar mass of 16.00 g/mol. Adding them up gives a molar mass of approximately 68.06 g/mol for sodium ethylate.
Sodium Ethoxide Boiling Point
Sodium ethylate has a boiling point of around 90-95°C (194-203°F). This temperature indicates the point at which sodium ethylate changes from a liquid to a gas phase when heated under standard atmospheric pressure.
Sodium Ethoxide Melting Point
The melting point of sodium ethylate is approximately 260-270°C (500-518°F). It signifies the temperature at which solid sodium ethylate transitions to a liquid state.
Sodium Ethoxide Density g/mL
Sodium ethylate has a density of about 0.868 g/mL. Density refers to the mass of a substance per unit volume and can be used to determine its relative heaviness or lightness compared to an equal volume of water.
Sodium Ethoxide Molecular Weight
The molecular weight of sodium ethylate, also known as the molecular mass, is approximately 68.06 g/mol. It is calculated by summing up the atomic masses of all the atoms present in a molecule of sodium ethylate.
Sodium Ethoxide Structure
Sodium ethylate has a structure where the sodium atom (Na) is bonded to the oxygen atom (O) through an ionic bond. The ethoxide group, consisting of two carbon atoms (C) and five hydrogen atoms (H), is attached to the sodium atom.
Sodium Ethoxide Solubility
Sodium ethylate is highly soluble in polar solvents such as ethanol (C2H5OH) and other organic solvents. It readily dissolves in these solvents to form a clear, colorless solution, facilitating its use as a reagent in various organic reactions.
| Appearance | Colorless solid |
| Specific Gravity | 0.868 g/mL |
| Color | Colorless |
| Odor | Odorless |
| Molar Mass | 68.06 g/mol |
| Density | 0.868 g/mL |
| Melting Point | 260-270°C (500-518°F) |
| Boiling Point | 90-95°C (194-203°F) |
| Flash Point | Not applicable |
| Water Solubility | Reacts with water |
| Solubility | Soluble in such as ethanol (C2H5OH) and other organic solvents |
| Vapour Pressure | Not available |
| Vapour Density | Not available |
| pKa | Not available |
| pH | Basic (alkaline) |
Sodium Ethoxide Safety and Hazards
Sodium ethylate poses several safety hazards and precautions should be taken when handling it. It is a corrosive substance that can cause severe burns to the skin, eyes, and respiratory system. Direct contact should be avoided, and protective gloves, goggles, and clothing should be worn. It reacts violently with water, releasing flammable hydrogen gas, and should be stored away from moisture. Sodium ethylate can also react vigorously with air, potentially leading to fire or explosion. Proper ventilation is crucial to prevent the buildup of vapors. Additionally, it is important to handle sodium ethylate in a well-equipped laboratory with trained personnel to minimize risks and ensure safety.
| Hazard Symbols | Corrosive |
| Safety Description | – Causes severe burns<br>- Reacts violently with water<br>- Keep away from moisture<br>- Handle with care<br>- Use protective equipment<br>- Store in a dry place<br>- Ensure proper ventilation |
| UN IDs | UN2922 |
| HS Code | 2905.19.00 |
| Hazard Class | 8 (Corrosive substances) |
| Packing Group | II |
| Toxicity | Toxic if ingested or inhaled |
Sodium Ethoxide Synthesis Methods
Several methods can synthesize sodium ethylate.
One way to synthesize sodium ethylate involves the reaction between sodium metal and ethanol. Sodium metal undergoes a redox reaction with anhydrous ethanol, resulting in the formation of sodium ethylate. To carry out the reaction, one can add small pieces of sodium metal to absolute ethanol and reflux the mixture under controlled conditions.
Another method entails the reaction between sodium hydroxide (NaOH) and ethanol. One dissolves sodium hydroxide in ethanol and heats the mixture, which promotes the reaction to yield sodium ethylate. Chemists commonly use this method when they do not prefer the direct reaction between sodium metal and ethanol.
As an alternative, they can prepare sodium ethylate by reacting ethanol with sodium carbonate (Na2CO3). One dissolves sodium carbonate in ethanol, and then heats and stirs the mixture. This process leads to the formation of sodium ethylate.
It is worth noting that these synthesis methods require strict adherence to safety precautions due to the reactivity of the involved chemicals. Proper handling of flammable substances, use of protective equipment, and conducting the reactions in well-ventilated areas are essential for the safety of the personnel and the successful synthesis of sodium ethylate.
Sodium Ethoxide Uses
Sodium ethylate finds various applications due to its reactivity and strong basic nature. Here are some common uses:
- Organic Synthesis: Sodium ethylate serves as a strong base extensively in organic synthesis. It facilitates reactions such as esterification, condensation, and deprotonation processes.
- Alkoxide Reagent: It serves as an alkoxide reagent, which can react with various organic compounds to form alkoxides. These alkoxides are crucial intermediates in many organic reactions.
- Catalyst: Sodium ethylate acts as a catalyst in several chemical reactions. It promotes the conversion of organic compounds, such as alcohols and esters, into their corresponding ethers or esterification products.
- Dehydration Agent: It dehydrates organic compounds by removing water molecules, facilitating the synthesis of anhydrous products.
- Polymerization: Sodium ethylate participates in polymerization reactions, specifically in the production of polyethylene terephthalate (PET) and other polyester polymers.
- Pharmaceutical Manufacturing: It finds applications in the pharmaceutical industry for the synthesis of various pharmaceutical compounds, including esters, ethers, and intermediates.
- Biodiesel Production: The transesterification process utilizes sodium ethylate to convert vegetable oils or animal fats into biodiesel, a renewable and environmentally friendly fuel.
- Lab Reagent: Researchers commonly use sodium ethylate as a reagent for organic reactions and in experimental setups.
Questions:
Q: Is sodium ethoxide a base?
A: Yes, sodium ethylate is a base.
Q: Is sodium ethoxide a strong or weak base?
A: Sodium ethylate is a strong base.
Q: What would you expect to happen if sodium ethoxide were added to water?
A: If sodium ethylate is added to water, it would react vigorously, releasing hydrogen gas and forming sodium hydroxide.
Q: Is sodium ethoxide a strong or weak base?
A: Sodium ethylate is a strong base.
Q: Is sodium ethoxide a strong nucleophile?
A: Yes, sodium ethylate is a strong nucleophile.
Q: Which of the following most readily undergoes an E2 reaction with sodium ethoxide?
A: The compound with a primary or secondary leaving group would most readily undergo an E2 reaction with sodium ethylate.
Q: Is sodium ethoxide a strong nucleophile?
A: Yes, sodium ethylate is a strong nucleophile.
Q: Is sodium ethoxide a base?
A: Yes, sodium ethylate is a base.
Q: Which of the following most readily undergoes an E2 reaction with sodium ethoxide (NaOCH2CH3)?
A: A compound with a primary or secondary leaving group would most readily undergo an E2 reaction with sodium ethylate.
Q: Is sodium ethoxide flammable?
A: Sodium ethylate itself is not flammable, but it reacts violently with water, releasing flammable hydrogen gas.
Q: What, combined with ethanol, makes sodium ethoxide and hydrogen?
A: The combination of sodium metal and ethanol produces sodium ethylate and hydrogen gas.
Q: What would you expect to happen if sodium ethoxide were added to water?
A: If sodium ethylate were added to water, it would react vigorously, releasing hydrogen gas and forming sodium hydroxide.