Epichlorohydrin is a colorless liquid that is primarily used in the production of epoxy resins. It is manufactured through the chlorination of propylene to allyl chloride, followed by the chlorohydration of allyl chloride with hypochlorous acid to form glycerol dichlorohydrins. These are then treated with alkali to yield epichlorohydrin. Nearly 70% of epichlorohydrin production is used to make bisphenol A diglycidyl ether, which is used to produce epoxy resins that have applications in coatings, composites, adhesives, electronics, and more due to their

1. Mr. Abraham G. Dayklee
BSc. Biology/Chemistry
Stella Maris Polytechnic
Mother Patern College of Health Sciences

3.  Epichlorohydrin is an organochlorine compound
and an epoxide.
• It is a liquid epoxide.
The basic structure of an epoxide contains
an oxygen atom attached to two adjacent
carbon atoms of a hydrocarbon.
 Manufactured by the chlorohydrination
of allyl chloride.

4.  Nearly 70% of all epichlorohydrin is used
in the production of epoxy resin.
 This colorless liquid with its irritating chloroform
like odor finds it way into the production process of
various synthetic materials.
 The glycidyl group on both ends of the bisphenol A
are also referred to as an oxirane or ‘epoxy group'.
Bisphenol A
Epoxies

5.  Epoxy is a term used to denote both the
basic components and the cured end products
of epoxy resins.
Epoxy has a wide range of applications, including:
 Metal coatings,
 Use in electronics / electrical components/LED
 High tension electrical insulators,
 Fiber-reinforced plastic materials
 Structural adhesives

6.  Coatings, adhesives and composite materials
such as those using;
• Carbon fiber and fiberglass Reinforcements.
• Polyester, vinyl ester,
 Thermosetting resins are also used for
glass-reinforced plastic.
 In general, epoxies are known for their
 Excellent adhesion
 Chemical and heat resistance
 Good-to-excellent mechanical properties
 Very good electrical insulating properties.

7.  Are also widely used as primers to improve
the adhesion of automotive and marine paints
especially on metal surfaces where corrosion
(rusting) resistance is important.
 Metal cans and containers are often coated
with epoxy to prevent rusting, especially for
foods like tomatoes that are acidic.

8.  Epoxy glues
 rubbers, paper saturated resins
 The most familiar epoxy resin is used as
a coating on the inside of food and beverage
cans to prevent rusting.
 Insect fumigation and as an intermediate for the
formation of glycidyl acrylate derivatives such as
those used in the manufacture of eyeglass lenses.

9.  Epoxy resins are also used for
decorative flooring applications
such as :
Terrazzo Flooring,
Chip Flooring,
Colored Aggregate Flooring.

10. Are adhesives Called "structural adhesives"
or "engineering adhesives“
 Polyurethane, acrylic,
 Cyanoacrylate,
 These high-performance adhesives are
used in the construction of :
 Aircraft, automobiles
Bicycles, boats, golf clubs
 Skis, snowboards

11. Are used as adhesives for wood,
metal, glass, stone, and some plastics.
They can be made flexible or rigid,
transparent or opaque/colored, fast
setting or slow setting.
 Epoxy adhesives are better in heat and
chemical resistance than other common
adhesives.

12.  Epoxy systems are used in industrial tooling
applications to produce:
 Molds, master models,
 Laminates, castings, fixtures,

13.  It is a colorless liquid with a pungent
garlic like odor.
 Moderately soluble in water
 Miscible with most polar organic
solvents.
 ISOPROPYL ALCOHOL
 CYCLOHEXANOL
 BUTANOL

14.  A highly reactive compound used in the
production of:
 Epoxy resins (its primary use)
A clear, low-viscosity, liquid.
 Epoxy glues
 Plastics
 Specialty water treatment chemicals
 Glycerol, Synthetic glycerin
 Wet-strength resins for paper production
and surfactants

15. In their cured form, epoxy resins possess
outstanding properties, including:
 Toughness
 Resistance to moisture and chemicals
 High tensile strength
 Good dielectric properties
In contact with water, epichlorohydrin
hydrolyzes to a carcinogen
found in food.

16.  Epichlorohydrin (C3H5Cl)
 Is a colourless liquid the vapour of which
forms explosive mixtures with air.
 During burning Phosgene, hydrogen
Chloride and carbon monoxide are liberated.
 Polymerization reaction is initiated by
 Acids
 Caustic solutions
 Halide salts

17.  The compound is very reactive with metals such as:
 Zinc and aluminium
 Anhydrous metal halides
 Strong acids and bases, and alcohol
containing materials.
 Epichlorohydrin in the presence of moisture
attacks steel.

18.  Epichlorohydrin was first described
in 1848 by Marcellin Berthelot.
 It was isolated during studies on reactions
between glycerol and gaseous hydrogen
chloride.
 It was manufactured from
allyl chloride in two steps:
1. Addition of hypochlorous acid, which affords a mixture of two alcohols:
CH2=CHCH2Cl + HOCl → HOCH2CHClCH2Cl
OR: ClCH2CH(OH)CH2Cl

19. 2) In the second step, this mixture is treated with base to give the epoxide.
 In this way, more than 800,000 tons (1997)
of epichlorohydrin are produced annually.

20.  Glycerol And Epoxy Resins Synthesis:
 Epichlorohydrin is mainly converted
to bisphenol:
 A diglycidyl ether, a building block in
the manufacture of epoxy resins.
 It is also a precursor to monomers for other
resins and polymers.
 Another usage is the conversion to synthetic glycerol:
CH2CHOCH2Cl + 2 H2O → HOCH2CH(OH)CH2(OH) + HCl

22. Epichlorohydrin is a versatile precursor in the synthesis
of many organic compounds.
 It is converted to glycidyl nitrate,
an energetic binder used in explosive
and propellant compositions.
 The epichlorohydrin is reacted with
an alkali nitrate, such as sodium nitrate,
producing glycidyl nitrate
and alkali chloride.
 It is used as a solvent for cellulose,
resins, and paints, and it has found use
as an insect fumigant.

23. Polymers made from epichlorohydrin:
 Polyamideepichlorohydrin resins
are used in paper reinforcement and in
the food industry to manufacture
 Tea bags
 Coffee filters
 And sausage/salami casings
 Water purification.

24.  Epichlorohydrin is commercially prepared
by high temperature chlorination of propylene
to allyl chloride:
 i.e., it is usually prepared from
propene, which is chlorinated to allyl chloride
 Followed by chlorohydration with hypochlorous
acid to form isomeric glycerol dichlorohydrins.
 i.e. the allyl chloride is chlorinated in water
by hypochlorous acid to yield a mixture
of isomeric glycerol chlorohydrins.

25.  The mixture is subsequently dehydrochlorinated
with alkali to yield epichlorohydrin.
 i.e. After dehydrochlorination with alkali,
epichlorohydrin can be separated by
steam distillation.

26.  The by-products are:
 Cis- and trans-1,3-dichloropropene
 1,2-dichloropropane.
 Glycerol dichlorohydrins are made
from allyl chloride, with 1,2,3-tri
chloropropane being obtained as a
byproduct.
 Finally, epichlorohydrin is produced from the
glycerol-dichlorohydrin mixture by treatment with base.
1,2-dichloroproepan1,3-dichloropropene
Bonded line: 1,3-dichloropropene

28. The primary use of epichlorohydrin
is in the production nof:
 Epoxy resins
used in coatings
adhesives, and plastics.

29.  Epichlorohydrin is also used in the
manufacture of the following:
 Synthetic glycerine
 Textiles
 Paper
 Inks and dyes
 Solvents
 Surfactants
 Pharmaceuticals.

30.  Epichlorohydrin is also listed as
an inert ingredient in commercial
pesticides.
It is also used for bottles, plastics
production.

31. Adhesives and sealant chemicals
Intermediates
Solvents
(which become part of product formulation or mixture)

32.  CONSUMER USED:
Adhesives and Sealants
Paints and Coatings
 Wet strength resins for the paper industry,
 Water‐treatment resins,
 Surfactants, ion‐exchange resins,
 Plasticizers, dyestuffs, pharmaceutical products,
 Oil emulsifiers, lubricants, and adhesives

33.  Epoxy resin formulations are important in the electronics industry, and are employed in
 Motors, generators,
 Transformers, switchgear,
 Bushings, and insulators.
 The are excellent electrical insulators
and protect electrical components from
short circuiting, dust and moisture.

34.  Exposure overtime induce an:
 ALLERGIC REACTIONS
in areas where the exposure has been
highest often visible in the form of
DERMATITIS
 Occurs commonly hands
and forearms

36.  SENSITIZATION
through poor working hygiene
and/or lack of protective equipment
 It is a main source occupational
ASTHMA among users of plastics.
 BISPHENOL A:
which is used to manufacture a common
class of epoxy resins, is a known
ENDOCRINE DISRUPTOR

37. Epichlorohydrin is a highly reactive
and flammable chemical.
It is absorbed rapidly via the skin,
gastrointestinal tract, and, in vapour form,
via the lungs.
It is distributed widely throughout the body.
In rodents, retention in tissues mainly occurs at
the portal of entry, i.e.,
The nasal epithelium during inhalation
And the stomach after oral exposure.

38.  Use in adhesives and coatings
 Paints and plastics.
 Metal cans and containers are often coated
with epoxy to prevent rusting, especially for
foods like tomatoes that are acidic.
 Epichlorohydrin is commercially prepared
by high temperature chlorination of propylene
to allyl chloride.
 Industrials uses includes:
Adhesives and sealant chemicals
Intermediates
Solvents

39. For more Information:
abrahamdaylee25@gmail.com
adayklee@yahoo.com
Contact: 0880760020/0776782278

40. 1. Merck Index, 12th Edition, 3648.
2. NIOSH Pocket Guide to Chemical Hazards #0254". National Institute for Occupational Safety and Health (NIOSH).
3. Epichlorohydrin Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health
(NIOSH).
4. EPA consumer factsheet. Epa.gov. Retrieved 20111202.
5. Berthelot, Marcellin (1854). "Sur les combinaisons de la glycérine avec les acides et sur la synthèse des principes
immédiats des graisses animaux". Ann. Chim. Phys. SER3. 41: 216–319.
6. Géza Braun "Epichlorohydrin and Epibromohydrin" Organic Syntheses,1936, Vol. 16, p.30.
7. Wikipedia