Alkylamine

What Is Alkylamine?

Amines are generated by substituting the alkyl or aryl group for one or more hydrogens from the compound ammonia. These compounds are referred to as alkylamines or arylamines. Alkylarylamines are amines that have both types of substituents bonded to a single nitrogen atom.

The chemistry of nitrogen-containing compounds is important in many crucial fields because they play key roles in the preparation of agrochemicals, dyes, explosives, surfactants, additives, and so on. In addition, nitrogen derivatives are typical building blocks for bioactive compounds such as amino acids, nucleotides, vitamins, hormones, organic catalysts and others.

Table of Contents

Synthesis of Alkylamines

N-alkylamine is one of the most important compounds among nitrogen-containing compounds, and a huge amount of attention has been given to this area for research since the 1900s. Traditionally, N-alkylamines are synthesised using alkyl halides as alkylating reagents. However, this procedure is problematic due to amine overalkylation, the toxic nature of alkyl halides, and the generation of inorganic salt waste. There are several aspects to be noted in order to achieve a sustainable synthesis of N-alkylamines.

  • The use of alkyl halides as alkylating reagents should be replaced by alcohol, amine, alkene, alkane, carbon dioxide, and other sustainable molecules.
  • The employment of amines as nitrogen sources can be replaced by nitrobenzene, nitrile, and ammonia to avoid multistep reactions.
  • Economic and efficient catalysts should be developed for the above transformations.

Amines with up to six carbons per alkyl chain are known as lower alkyl amines, and those with over eight carbons per alkyl chain are called fatty alkyl amines. Methyl and ethyl amines were first prepared by the hydrolysis of the corresponding alkyl isocyanate by Wurtz in 1849. However, Hofmann was the first chemist to use the terms primary, secondary and tertiary amines.

In general, most naturally occurring amines have complex structures; however, some simpler members are also available, such as tetramethyl diamine, pentamethylenediamine and di(4-amino-n-butyl)amine. The lower alkyl amines are gases at room temperature (methylamine, dimethyl-amine, trimethylamine and ethylamine); higher amines up to about 12 carbons per chain are liquid, and longer carbons chains are solids at ambient temperature.

General Properties of Alkylamines

The physical properties of some alkylamines are summarised below.

Amines

Melting Point

Basicity of Amines

Methylamine

-92

4.5

Dimethylamine

-96

5.4

Trimethylamine

-117

0.6

Ethylamine

-80

5.1

Diethylamine

-39

10

n-Propylamine

-83

4.1

t-Butylamine

-67

4

Pentylamine

-55

4.2

Cyclohexylamine

17.7

5

Octylamine

0

4.4

Decylamine

17

4.5

Ethylenediamine

8

0.7

Tetramethylethylenediamine

27

0.85

Hexamethylethylenediamine

39

5

The major applications for amines are in the areas of agrochemicals, dyestuffs, pharmaceuticals, surfactants, plastics, and chemical auxiliaries, for example, rubber, textiles, paper manufacture, anti-corrosion agents, and as process chemicals.

Recommended Videos

Amines – One-Shot

Most Important and Expected Questions – Amines

Classification of Amines

Physical Properties and Basic Strength of Amines

Frequently Asked Questions (FAQs)

Q1

What is alkylamine used for?

Alkyl amines are extensively used in the production of rubber-making chemicals, surfactants, solvents and insecticides. Alkyl amines are used in a variety of products, including explosives, chemicals, water purification, pharmaceuticals and agriculture.

Q2

Is dimethylamine a weak or strong base?

Dimethylamine is a stronger base than methylamine because the dimethyl groupโ€™s +I impact is greater than the methyl group. Therefore, dimethylamine is a strong base.

Q3

What is another name for ethylamine and its chemical formula?

The chemical compound ethanamine, also known as ethylamine, has the formula CH3CH2NH2.

Q4

What is the use of triethylamine?

Triethylamine is a clear, colourless liquid with ammonia, and has a fish-like odour. It serves as a catalyst, corrosion inhibitor and propellant, and is used in the production of waterproofing agents.

Q5

What is the charge of ethylenediamine?

Ethylenediamine has an oxidation number of 0. Its charge will therefore be 0.