VSAT 2022

What Is Diethyl Ether?

The organic compound diethyl ether is made up of two carbon atoms connected by an oxygen atom (C-O-C). It is a colourless, highly flammable, highly volatile liquid with an ethereal odour (sweet smelling). The molecular formula of diethyl ether is $C{{H}_{3}}C{{H}_{2}}OC{{H}_{2}}C{{H}_{3}}$ and the IUPAC name of diethyl ether is ethoxyethane.


Valerius Cordus synthesised diethyl ether in the year 1540 and gave it the name "sweet oil of vitriol" (oleum dulce vitrioli), reflecting the fact that it is produced by distilling a mixture of ethanol and sulfuric acid. August Sigmund Frobenius named the substance "ether" in 1729. It is frequently used as an engine starter fluid and as a solvent in laboratories. Before non-flammable medications like halothane were created, it was used as a general anaesthetic. Intoxicating recreational drugs have been made from it in the past.


Structure of Diethyl Ether

Diethyl ether usually referred to as ethyl ether, is an ether-class chemical molecule with the formula ${{({{C}_{2}}{{H}_{5}})}_{2}}O$. R-O-R. It is used to signify diethyl ether. Here, R stands for the alkyl group(${{C}_{2}}{{H}_{5}}$), and O stands for the oxygen atom.


Structure of Diethyl Ether


Structure of Diethyl Ether


Physical Properties of Diethyl Ether

  • Diethyl ether is a colourless liquid with a molar mass of 74.123 g/mol.

  • It is highly volatile.

  • It is highly flammable.

  • It has a sweetish pungent odour.

  • The boiling point is 34.6 °C (94.3 °F; 307.8 K).

  • The melting point is -116.3 °C (-177.3 °F, 156.8 K).

  • Its density is 0.7134 $\mathrm{g}/\mathrm{cm}^3$ , liquid.

  • Its vapour pressure is 440 mmHg at 20 °C (58.66 kPa at 20 °C).


Chemical Properties of Diethyl Ether

${{C}_{2}}{{H}_{5}}O{{C}_{2}}{{H}_{5}}\,+\,6{{O}_{2}}\,\to \,4C{{O}_{2\,}}+\,5{{H}_{2}}O$

  • Halogenation: On halogenation with halogens like chlorine or bromine, diethyl ether undergoes a substitution reaction to form halo-substituted ether in the absence of sunlight.

${{C}_{2}}{{H}_{5}}O{{C}_{2}}{{H}_{5}}\,+\,C{{l}_{2}}\,\to \,{{C}_{2}}{{H}_{4}}(Cl)O{{C}_{2}}{{H}_{4}}(Cl)$


Preparation of Diethyl Ether

  • Diethyl ether is produced by heating dry silver oxide with ethyl iodide.

  • Williamson synthesis: This process involves heating sodium or potassium ethoxide with chloro, bromo, or iodo ethane. Diethyl ether and sodium iodide are the products of this reaction.

${{C}_{2}}{{H}_{5}}ONa\,+\,{{C}_{2}}{{H}_{5}}I\,\to \,{{C}_{2}}{{H}_{5}}O{{C}_{2}}{{H}_{5}}\,+\,NaI$

  • Diethyl ether is produced by heating ethyl alcohol with alumina (Al2O3) at 250°C.

${{C}_{2}}{{H}_{5}}OH\,\xrightarrow[250]{A{{l}_{2}}{{O}_{3}}}\,{{C}_{2}}{{H}_{5}}O{{C}_{2}}{{H}_{5}}\,+\,{{H}_{2}}O$

  • Laboratory method: A high concentration of ethyl alcohol is combined with a less concentrated sulfuric acid, and the resultant mixture is heated to roughly 140°C to produce diethyl ether.

${{C}_{2}}{{H}_{5}}OH\,+\,{{H}_{2}}S{{O}_{4}}\,+\,{{C}_{2}}{{H}_{5}}HS{{O}_{4}}\,+\,{{H}_{2}}O$

${{C}_{2}}{{H}_{5}}HS{{O}_{4}}\,+\,{{C}_{2}}{{H}_{5}}OH\,\to \,{{C}_{2}}{{H}_{5}}O{{C}_{2}}{{H}_{5}}\,+\,{{H}_{2}}S{{O}_{4}}$


Health Hazards of Diethyl Ether

  • Highly flammable liquid and vapour and it may also form explosive peroxides.

  • It is very harmful if swallowed and causes drowsiness, dizziness, and may induce vomiting.

  • Continual exposure to ether could result in skin dryness or cracking and may also damage the proper functioning of kidneys.


Uses of Diethyl Ether

  • It is used as a fuel:

Due to its high volatility and low flash point, diethyl ether, which has a high cetane number of 85–96, is utilised as a starting fluid in combination with petroleum distillates for gasoline and diesel engines.

  • Chemistry:
    A typical aprotic solvent used in laboratories is diethyl ether.
    It dissolves in water at a rate of 1.5 g/100 g (1.0 g/100 ml) and has low solubility in water (6.05 g/100 ml at 25 °C). This makes it perfect for use as a non-polar solvent in liquid-liquid extraction, along with its high volatility.
    In addition to other reactions employing organometallic reagents, the Grignard reaction uses it as a typical solvent.

  • Anesthesia:

Due to ether's better therapeutic index, or a bigger gap between an effective dose and a potentially toxic dose, diethyl ether generally replaced the use of chloroform as a general anesthetic.

  • Recreational use:
    Ether is a recreational substance because of its anesthetic and euphoric properties. A long history of recreational use exists for the inhalant diethyl ether in anesthetic dosage.


Important Questions

1. Name a few physical properties of diethyl ether.

Ans: Diethyl ether is an organic compound that is colorless, ethereal odoured, highly flammable, and highly volatile liquid with a melting point and boiling point of -116.3 °C and 34.6 °C respectively.


2. Mention a method to prepare diethyl ether.

Ans: Diethyl ether can be prepared by distilling highly concentrated ethyl alcohol with sulphuric acid at about 140 degrees Celsius.


Summary

Ethyl ether, commonly referred to as diethyl ether, is a popular anesthetic that is a member of the large class of chemical compounds known as ethers. The molecular formula and the IUPAC name of diethyl ether are $C{{H}_{3}}C{{H}_{2}}OC{{H}_{2}}C{{H}_{3}}$ and ethoxyethane, respectively. It is a colourless, ethereal odoured, highly flammable, and highly volatile liquid with a melting point and boiling point of -116.3 °C and 34.6 °C, respectively. It is commonly used as a laboratory solvent, fuel, and anesthetic.


Practice Questions

1. Which one of these is not a synonym of diethyl ether?

  1. Ethyl ether

  2. Ethoxyethane

  3. Ethoxymethane

  4. Ether

2. Which of these is a structural isomer of diethyl ether?

  1. Butanal

  2. Butanol

  3. Butane

  4. Butene

Answers

  1. (c)

  2. (b)

FAQs on Diethyl Ether

1. Is diethyl ether still used as an anaesthetic drug during operations?

Yes, diethyl ether is still used as an anaesthetic during medical procedures in many developing countries. The key reasons for this are diethyl ether’s extremely low cost and strong therapeutic index, which reduces respiratory and cardiac discomfort during medical procedures. It is important to keep in mind the fact that ether is not legal to use as an anaesthetic in many nations. Its volatility, flammability, and its toxicity for human beings on higher doses are the reason for this.

2. State the common name of diethyl ether

Diethyl ether is also known as ethyl ether.

3.  An individual has Inhaled Diethyl Ether by mistake. What can happen in this situation?

According to medical experts, breathing or inhaling diethyl ether can cause throat and nose irritation. If an individual has inhaled diethyl ether, then he or she can expect to experience drowsiness, dizziness, arousal, irregular breathing, vomiting, and saliva. In case of high exposure to diethyl ether, the situation can worsen due to unconsciousness or even death.

4. Is Ether still used as an anesthetic during medical operations?

Yes, ether is still used as an anaesthetic in various developing countries. This is mainly because this substance is very low cost and has a high therapeutic index with reduced respiratory and heart distress. It is also important to remember that there are also many countries in which the use of ether as an anesthetic is not allowed. This is because it has a volatile flammability.

5. Can Diethyl Ether be characterized as being flammable?

Diethyl ether is extremely flame retardant. This substance can produce explosive mixtures of air and vapour. It is also interesting to note that ether peroxide has a boiling point higher than ether and can be explosive on contact when present in dry form.

6. What is Diethyl Ether?

Ethyl ether, also known as diethyl ether, is a well-known anaesthetic that belongs to a broad group of organic compounds known as ethers. Its molecular structure consists of two ethyl groups connected by an oxygen atom, as in C2H5OC2H5.

7. What are the Properties of Diethyl Ether?

Ethyl ether is a colourless, volatile, highly flammable liquid with a strong, distinctive odour and a hot, sweetish taste (boiling point 34.5° C [94.1° F]). Bromine, iodine, most fatty and resinous compounds, volatile oils, pure rubber, and some vegetable alkaloids all use it as a solvent.

8. How is Diethyl Ether Manufactured?

The distillation of ethyl alcohol with sulfuric acid produces ethyl ether. Washing crude ether with a saturated aqueous solution of calcium chloride, then treating it with sodium, produces pure ether (absolute ether), which is necessary for medical purposes and the preparation of Grignard reagents.

9. What is a halogenation reaction?

Halogenation is a kind of chemical reaction where a halogen atom is swapped out for another substance, and the halogen atom eventually becomes a component of that molecule or a compound. In general, one or more halogens are typically added to the chemical during the halogenation reaction. When a substance is halogenated, a new substance is created that has different qualities from the original substance. Iodine, chlorine, fluorine, and bromine are among the group of elements known as halogens.

10. What will happen if someone ingested/inhaled diethyl ether by mistake?

Experts in medicine say that breathing or inhaling or ingesting diethyl ether might irritate the nose and throat and cause uneasiness. An individual who has inhaled diethyl ether can anticipate feeling sleepy, and lightheaded, and can have erratic breathing patterns, excessively salivating, and feel nauseous. If one is exposed to large amounts of diethyl ether, it can cause respiratory paralysis, could cause Laryngospasm or one could become unconscious, could cause kidney failure, or perhaps even the person might pass away.

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