Prepared By:

Eugene Benito O. Rusiana

Amines in the
Chemical Industry

Amines: A Reintroduction
In Organic Chemistry (CHM141 and CHM142),
amines are structurally defined as organic
derivatives of ammonia (NH3), formed by replacing
one or more hydrogen atoms by alkyl or aryl
groups.
Amines can either be Primary (RNH2), Secondary
(R2NH), Tertiary (R3N) or Cyclic.
Amines are basic, and are thus superior
nucleophiles than other organic compounds.
In Chemical Nomenclature, amines have the suffix
-ine in their names.
Like ammonia, amines are notorious for their
disgusting odor, which is akin to rotting flesh or
waste matter.

Primary Amines: Aniline

Aniline is a versatile amine
with various applications
ranging from Pharmaceuticals
to Polymers.
Aniline is a precursor to the
synthesis of Methylene
Diphenyl Diisocyanate (MDI),
which in turn is a precursor to
the synthesis of Polyurethane,
a commercially vital plastic. It
is also used in the production
of acetaminophen (a.k.a.
paracetamol or Biogesic).

Secondary Amines: Dimethylamine

Dimethylamine is also
another industrially
significant amine with various
applications.
Its applications range from
pharmaceuticals, rocket fuel
and surfactants.
Dimethylamine is also utilized
by cockroaches as a
communication pheromone,
or a chemical whose odor is
utilized by animals as a means
of communication.

Tertiary Amines: Triethanolamine

Triethanolamine (TEA) is a
versatile and commerically
significant amine with various
industrial applications.
As an amine and an alcohol, TEA
possesses properties of both
functional groups, making it
chemically versatile.
Due to its unique properties, it
has found use in an exceptional
amount of industries, some of
which include Metalworking,
Cements, Personal Care Products
and Textiles.

Cyclic Amines: Proline

Proline (Abbreviations: Pro, P) is

one of the 20 naturally occurring
Amino Acids.
Alongside Glycine, it does not
follow the traditional structural
format of the other Amino Acids.
Prolines distinctive properties as a
cyclic compound are vital in the
formation of fibrous proteins such
as Keratin and Collagen.
Fibrous proteins are rich in Proline,
whose properties help in making
the protein insoluble in water as
well as enhancing its structural
rigidity.

Commercial Significance of Amines

Apart from their biological importance, many
amines have found various industrial
applications, ranging from polymers, fertilizers
and pharmaceuticals.
Commercially significant amines include Aniline,
Ethanolamines, Ethylenediamine and OrthoToluidine.
Methamphetamine (a.k.a. Crystal Meth or
Shabu), is arguably the most well known amine
known in the country.

Secondary Amines: Shabu

OBOSEEEEEEEEEEEEN

Local Manufacture of Amines

Aside from the illegal shabu syndicates in the
Philippines, there is no major dedicated producer
of amines in the Philippines, despite strong local
demand for these compounds.
However, major chemical companies that produce
amines in other countries such as The Dow
Chemical Company and BASF have local offices in
the Philippines. Currently, these companies import
their foreign-produced amines to the Philippines to
satisfy local demand.

Philippine Market for Triethanolamine

As of August 2016, there are currently no
producers of Triethanolamine (TEA), despite
highly promising Philippine demand trends for
the said chemical.
Using data from the United Nations Commodity
Trade Database, Philippine TEA imports may
rise to as much as 50,000 Metric Tons by 2024.
In the Philippines, TEA is used primarily by the
soap, personal care products, metalworking,
cement, concrete and agricultural chemical
industries.

Applications of Triethanolamine

Adhesive

Adhesives - as an intermediate for adhesive chemicals.

Agricultural Chemicals

Agricultural as an intermediate for herbicide, molluscide,

fungicide, and algaecide products.

Cement

Cement used to enhance strength, reduce drying time

and protect against the affects of freezing and thawing.
Triethanolamine (TEA) is used as a component in the
formulation of cement grinding media during the
manufacture of cements.

Detergents, Cleaners, Fabric softeners

Detergents, Cleaners, Fabric softeners to provide efficient

cleaning and prevent soil deposition.

Gas treating

Gas treating for a variety of natural gas, petrochemical, and oil

treatments.

Metalworking fluids

Metalworking fluids to neutralize acidic components in

lubricants and prevent corrosion and rusting and for proprietary
corrosion inhibitors and biocides.

Personal-care products

Personal-care products to produce soaps for use in hand lotions, cosmetic

creams, cleansing creams, shaving creams, and shampoos and for dry-cleaning
solvents and heavy-duty liquid laundry detergents.

Photographic chemicals

Photographic chemicals for use in complex modern

developing systems used by the photographic chemical
industry.

Rubber

Rubber as an intermediate for chemicals used in the

manufacture of rubber.

Surfactants

Surfactants - to react with long-chain fatty acids to form surfaceactive soaps used in emulsifying additives in textile lubricants,
polishes, detergents, pesticides, and personal-care products such as
hand lotions, shaving creams, and shampoos.

Textiles and textile additives

Textiles and textile additives as aids to clean and scour textiles,

facilitate wetting, and improve lather and ease of soap removal.

Production of Triethanolamine
Raw Materials: Ethylene Oxide, Ammonia
Reactors: Plug Flow Reactor
Equipment: Distillation Columns

Triethanolamine Reaction

Ethylene Oxide
Chemical Formula:
C2H4O
Other Names: Oxirane
Moiety: Epoxide
Melting Point: -111.3oC
Boiling Point: 10.7oC

Ammonia

Chemical Formula: NH3

Other Names: N/A
Moiety: N/A
Melting Point: -77.73oC
Boiling Point: -33.34oC

Triethanolamine

Hazards of the Raw Materials

Ethylene Oxide
As an epoxide, EO is
incredibly reactive by
nature. It can very easily
explode if exposed to an
ignition source.
EO is also toxic by
inhalation, as well as a
carcinogen.

Ammonia
Ammonia is a relatively
powerful base, although
not to the same extent
as Alkali Hydroxides.
Ammonia is also toxic,
so prolonged inhalation
is hazardous to ones
health.

Triethanolamine: Block Flow Diagram

Triethanolamine PFR Conditions

Ammonia Column Conditions

Monoethanolamine Column Conditions

Triethanolamine Column Conditions

References
Organic Chemistry by T. W. Graham Solomons and Craig
Frhyle
Organic Chemistry by Janice Smith
Dow Amines (http://www.dow.com/amines/index.htm)
Transport Processes and Unit Operations by Christi
Geankoplis
Perry's Chemical Engineers' Handbook, 8th Edition by Robert
Perry and Don Green
Physical Chemistry by Ira Levine
United Nations Commodity Trade Database
Ethylene Oxide MSDS
Ammonia MSDS
Monoethanolamine MSDS
Diethanolamine MSDS
Triethanolamine MSDS