Alkanolamines have the combined physical and chemical characteristics of both
alcohols and amines in one molecule, which makes them useful intermediates in
the synthesis of various target molecules for the use in many diverse areas such
as pharmaceutical, urethane catalysts, coatings, personal care, products, water
treatments, corrosion inhibitors, and gas treating industries. There are 1°, 2º
or 3º nitrogen atom and one hydroxyl group at least in alkanolamines.
Alkanolamines react with inorganic acids carboxylic acids to form salts, soaps,
esters, or amides. Alkanolamines are used in both water- based and solvent-based
coatings to enhance the solubility, reducibility, pigment dispersing and pH
stability. They are used in cathodic electrodeposition systems and as a catalyst
for chain-extend. Alkanolamines are used to prepare surface-active soaps through
reaction with fatty acids. Surface-active soaps are used commercially as a
emulsifier, lubricants, detergents, pesticides and personal care products.
Alkanolamines maintain a constant alkalinity in the boiling water flows and
condensate not to form solid products which would impede line flow. This
function is applied for corrosion Inhibits. Alkanolamines are widely employed in
the preparation of water soluble cationic flocculants and ion exchange resins
which adsorb solid and colloidal particles by electrostatic attraction. They are
used for water treatment industry. Alkanolamines and their derivatives are
widely used as intermediates for the production of active pharmaceutical
ingredients such as procaine, antihistamines analgesics from
N,N-dimethylethanolamine or N-methyldiethanolamine. Alkanolamines are used to
remove hydrogen sulfide (H2S) and CO2 gas from gas streams in natural and
refinery gas operations. Aminoethyl ethanolamine
which has amine groups and hydroxyl group
is used as an important intermediate
for polymer condensation, pharmaceuticals, agrochemicals,
paper chemicals, rubber chemicals, textile auxiliaries.
Aminoethyl ethanolamine is used to produce shampoo,
cationic surfactants, antistatic agents
and chelating agents.
Ethylenediamine is a colourless to yellowish, strongly alkaline liquid, melting
at 8.5 C, boiling at 116 C; completely soluble in water and soluble alcohol. It
is a manufactured chemical that does not occur naturally. It has two primary
amine groups. There are homologous odd number amine (on even number linear
carbon chain) series of ethylenediamines; diethylenetriamine (linear C-4
diamine), triethylenetetramine (linear C-6 triamine), tetraethylenepentamine
(linear C-8 pentamine), and pentaethylenehexamine (linear C-10 hexamine).
Diethylenediamine is the simplest cyclic ethyleneamine (C-4), called piperazine.
It has two secondary amine groups in cyclic system. It is a deliquescent
crystalline compound melting at 105 C; soluble in water, alcohol, glycerol, and
glycols. It is used as a main ingredient of anthelmintics and psychoactive
drugs. Aminoethylpiperazine is also a member of C- 6 cyclic ethyleneamine which
has aminoethyl attached to a nitrogen in piperazine. Accordingly, it has one
primary, one secondary, and one tertiary nitrogen atom. It is used in the
synthesis of catalysts, epoxy curing agent, and corrosion inhibitors.
Aminoethylethanolamine (AEEA) is an analogue of diethylenetriamine. A hydroxyl
group replace for an primary amine group. AEEA has one primary amine, one
secondary amine, and one primary hydroxyl group. AEEA is a useful intermediate
in the production of surfactants, chelating agents, and curing agents. Other
branched or cyclic ethylenediamines include N,N'-Bis-(2-aminoethyl)piperazine)
[CAS #: 6531-38-0], N-[(2-aminoethyl)2-aminoethyl]piperazine) [CAS #: 24028-46-4], tris(2-aminoethyl)amine)
[CAS #: 4097-89-6].
Ethylenediamines are produced by the reaction of aqueous ammonia with
1,2-dichloroethane. This process yields the mixture of polyamines in the form of
hydrochloride salts. The next step is neutralisation of the salts with aqueous caustic soda
to separate free amines. The individual free amines are isolated by fractional
distillation. Ethylenediamines are capable of entering into a variety of
reactions because of their combination of reactivity, basicity, and surface
activity and of the basic functionality of the nitrogen atom. They are therefore
important intermediates for a wide variety of chemical syntheses. Examples of
products obtained by reacting amines are as follows:
- with carboxylic acid
dericatives (acids, esters, anhydrides, or acyl halides): amides and
- with fatty acid: imidazoline
- with cyanides or nitriles:
amidoamines, polyamides, imidazolines
- with urea: substituted urea and
- with ethyleneimines: hydroxyalkyl amine derivatives
- with aliphatic
alcohols and glycols: alkylated ethyleneamines or cyclic ethyleneamines
alkyl or aryl halides: substituted amines
- with aliphatic aldehydes:
- with carbon disulfide: thiocarbamates
carbon dioxide: carbamate
- with inorganic acids: water soluble
Ethylenediamine is used as a very important bidentate ligand
forming chelate agents. The main application is to produce chelating agents
such as ethylenediaminetetraacetic acid (EDTA). It is used in the manufacture of
carbamate fungicides, surfactant and dyes. It is useful also in manufacturing
accelerator or curing agent in epoxy industry. Additional applications include
manufacturing photography development chemicals and cutting oils, bleaching
activators for washing powders especially at low temperature, lubricant for
plastics and polyamide process, and fuel additives.
a yellow, hygroscopic liquid; boiling point of 206 C; soluble in water and
hydrocarbons. It is used as a solvent for sulfur, acidic gas, resin and as a
fuel and oil field component. It is used as an Intermediate for organic
synthesis (modified polyamides, corrosion inhibitors, fuel additives, epoxy
curing agents, fabric softeners and adhesion promoters) and saponification agent
for acidic materials.
Triethylenetetramine is a clear to yellowish oily
liquid; melting point 12 C, boiling point 280 C. It is miscible with water and
the solution is alkaline ( (pH 10 at 10% solution). It reacts with ketones,
halogenated hydrocarbons, nitriles, epoxides, and with strong oxidants.
Commercial triethylenetetramine is a mixture of linear TETA (typically 60%) and
branched or cyclic TETA such as N,N'-Bis(2-aminoethyl)piperazine,
N-[1-(2-piperazin-1-yl-ethyl)]ethane -1,2-diamine, tris-(2-aminoethyl)-amine.
TETA and its derivatives are used as an epoxy curing agent. Their applications
are similar to those of ethylenediamine and diethylenetriamine.
of ethylenediamine family products include:
- Fabric Softeners
- Ore Flotation
- Corrosion Inhibitors
- Chelating Agents
- Bleach Activators
- Epoxy Curing Agent