Epoxidation of Castor oil

1. EpoxidationOf
CastorOil
Bhushan Patare
17OIL206

2.  Castor oil - valuable raw material for the chemical
industry
 Natural polyol which has about 90% of Mono
unsaturation
 Ability of Ricinoleic Acid to undergo various
reactions.
 Epoxidation is a commercially important reaction.
 Wide applications - due to the high reactivity of the
epoxy ring

3. Reactions

4. Reaction

5. Industrial
Method
 epoxidation of castor oil is carried out with
performic or peracetic acid.
 In situ acid catalyzed peroxidation of the
corresponding acid with high strength hydrogen
peroxide (up to 70% w/w).
 Soluble mineral acid (usually Sulphuric acid) or
acidic cation exchange resin (such as the
sulphonated polystyrene-type Amberlite) are
commonly used as catalyst for this reaction.
 Peracids are unstable, and the reaction is
exothermic.
 The concentration of peracid is kept low by using a
low concentration of the carboxylic acid either in
the neat oil or in a hydrocarbon solvent.
 dihydroxy and hydroxy carboxylates as byproducts.

6. Lab Method
with Ion
exchange
resin as
catalyst
 500 mL three-neck RBF in water bath (±1 K)
 magnetic stirrer, thermometer, reflux condenser
and dropping funnel
 Oil (100 g) was mixed with an equal mass of
benzene and an appropriate mass of glacial acetic
acid before addition of an ion exchange resin
 CO unsat. to H2O2 ratio 1:1.5
 Dropwise H2O2 addition to the reaction mixture at a
constant rate over the course of half - one hour.
 Temperature was maintained at 303 K - 323 K
 Continuous stirring at 1500 rpm for fine dispersion.

7. Optimized
Conditions
 The process of epoxidation is significantly
influenced by reaction variables such as molar ratio
of reactants, type of catalyst, catalyst loading,
temperature, stirring speed and presence of an
inert solvent.
 epoxidation occurred optimally at a temperature of
323 K
 0.5 mol of glacial acetic acid and
 1.5 mol of (30% w/w) aq. hydrogen peroxide
solution
 per mol of double bond of castor oil used
 catalyzed with 10 wt% of the ion exchange resin.
 maximum yield reached with 15 wt% of catalyst

8.  Centrifugation of mixture for separation of oil and
aqueous phase
 Oil phase was dissolved in diethyl ether
 Washed with distilled water (first cold then warm)
until it was acid-free
 Then dried by adding anhydrous Na2SO4
 Samples were then analyzed for iodine number (IN)
and epoxy oxygen content (EO)
 At the end of the reaction the ion exchange resin
was filtered from the cooled reaction mixture,
washed with water and diethyl ether, and air-dried.

9. Enzymatic
Method
 Chemo-enzymatic epoxidation uses the
immobilized lipase from Candida antartica
(Novozym 435) to catalyze conversion of fatty acids
to Peracids with 60% hydrogen peroxide.
 The lipase is remarkably stable under the reaction
conditions and can be recovered and reused 15
times without loss of activity.
 Methyl esters are also epoxidized without
hydrolysis under these conditions.

10. Physico-
chemical
properties

11.  ECO can be used directly as plasticizers and
polymer stabilizers, as paint and coating
components, as lubricants.
 Also as intermediates for alcohols, glycols,
alkanolamines, polyols and polymers (such as
polyurethanes, polyesters, and epoxy resins)
production due to the high reactivity of the epoxy
ring.

12. Reaction of
Epoxy ring
with
Nucleophile

13. Acrylation
Of ECO

14. ECO
Manufacture
rs &
Exporters
 Jayant Agro Organics Limited
 Sebacic India Limited
 Arvalli Castor Pvt. Limited
 Ihsedu Sp. Chemicals Pvt. Limited
 Biotor Industries Limited
 Allanasons Limited (Mumbai)

15. References
 Epoxidation of castor oil fatty acid methyl esters
(COFAME) as a lubricant base stock using
heterogeneous ion-exchange resin (IR-120) as a
catalyst: Venu Babu Borugaddaa,VaibhavV Gouda
 Kinetics of the Epoxidation of Castor Oil with
Peracetic Acid Formed in Situ in the Presence of
an Ion-Exchange Resin: Milovan R. Janković,
SnežanaV. Sinadinović-Fišer,* and Olga M.
Govedarica
 Epoxidation of castor oil with peracetic acid
formed in situ in the presence of an ion exchange
resin: Sneˇzana Sinadinovi´ c-Fiˇser∗, Milovan
Jankovi´ c, Olga Borota
 Castor Oil Modified by Epoxidation,
Transesterification and Acrylation Process:
Spectroscopic Characteristics: G. S. Sudha,
Hemjyoti Kalita, Smita Mohanty & Sanjay Kumar
Nayak
 Bailey’s IndustrialOil And Fats (6th edition)

16. THANK YOU !!