Amines

BY: KAMRAN MANJINDER AND JENNIFER

Introduction of Amines

Considered Organic derivatives of Ammonia (NH3)

One or more hydrogen atoms are replaced by an alkyl or Aromatic group

Classified as primary, secondary, and tertiary amines

Dependent upon the number of Organic groups directly attached to the Nitrogen atom

Rules/Laws to predict predominant product(s) And ReactionsPrimary amines

Find the longest continuous carbon chain containing the amine group to get the parent compound.

Drop the final –e of the parent name and add the suffix –amine.

Number the parent chain to give the amine carbon the lowest possible number

Name and number all sub-chains as usual

Secondary and tertiary amines Add the prefix N-alkyl to the name of the parent for 2° and 3°

amines

Cont’d - Examples

The simplest aromatic amine is benzenamine

4-chlorobenzenamineN,N-Dimethylbenzene

Structural Drawings of reactions

• Amines React as a weak base in an aqueous solution• Nitrogen will act as a proton (H+) acceptor • Water would act as the proton donor

Cont’d Reactions

When an amine is neutralized by an acid, and alkylammonium salt is produced.

Cont’d Reactions

An alkyl ammonium salt is the conjugate acid of the corresponding amine. Therefore alkyl ammonium salts will react with hydroxide ions to produce the amine and water.

Cont’d Reaction Catalysts

Amine Catalysts can be used in a variety of polyurethane foam applications

Example: Seat cushions, mattresses, refrigerators, freezers, and wall insulation

Common polyurethane amine catalysts are: triethylenediamine, pentamethyldiethylenetriamine, and dimethylcyclohexylamine

APPLICATIONS OF AMINES

Using amines as dyes

Primary aromatic amines are used as a starting material for the manufacture of azo dyes, some examples are as follows

1. methyl orange

2. direct brown 138

3. sunset yellow FCF

4. poncean

Using amines for drugs

Many drugs are designed to mimic or to interfere with the action of natural amine neurotransmitters , exemplified by the amine drugs:

·chlorpheniramine is an antihistamine that helps to relieve allergic disorders due to cold, hay fever, itchy skin, insect bites and stings.

· chlorpromazine is a tranquillizer that sedates without inducing sleep. It is used to relieve anxiety, excitement, restlessness or even mental disorder.

· ephedrine and phenyleprine, as amine hydrochlorides, are used as decongestant

Using amines for gas treatment

Aqueous monoethanolamine (MEA) and some other widely amines are used industrially for removing carbon dioxide (CO2) and hydrogen sulfide (H2S) from natural gas and refinery process streams.

They may also be used to remove CO2 from combustion gases /flue gases and may have potential for abatement of greenhouse gases. Related processes are known as sweetening.

Health and environmental impacts of amines

1. The process of post combustion ( CO2-capture by chemical absorption) relies on large scale of amines in aqueous solution. In such operations, emissions of amines may occur through the cleaned exhaust gas, as degraded solvent and as accidental spills. It is thus important that the chemicals used have low or no environmental effects.

2. To check this, standard ecotoxicity and biodegradability tests for a marine environment were performed on more than 40 amines, including both solvents already in use for CO2-removal and new promising chemicals.

Some of the solvents used for carbon capture, have been shown to have low biodegradability. The tertiary amines which have been tested do not degrade easily, while the amino acids tested both have low toxicity and degrade easily.