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PTT 259:
OLECHEMICA
L PROCESS &
PRODUCTS
OLEOCHEMIC
AL
PRODUCTS
OLEOCHEMICALS
OLEOCHEMICALS
Hydrolysis is a basic process which the fat and oil (triglyceride)are
splitting into crude glycerol and mixture of crude fatty acid
BASIC OLEOCHEMICALS
OLEOCHEMICAL
PATHWAYS
RAW
MATERIAL
S
PRIMARY
OLEOCHEMICALS
OLEOCHEMICALS
DERIVATIVES
Fatty Acid
 Fatty acid (FA) is produced via hydrolysis process of fat with
water.
Molecular Formula : CnH2nO2
General : R-COOH
Structural Formula :
Sources & Uses of Fatty Acids
Source
• Fatty acids from plant
and animal: oil palm,
coconut, corn,
soybean, sunflower,
fish
• Synthetic fatty acids
are derived from
petrochemical.
Uses
• Petrochemical
industry: tire industry,
soap, detergent, fatty
alcohol, polymer, fatty
amines, cosmetic,
pharmacy.
Process (from crude FA)
• used to purify the crude fatty acids under vacuum.
Distillatio
n
• increases the melting point of the fatty acids.
Hydrogenation is the conversion of unsaturated
acids into saturated acids.
Hydrogenation
• yields a liquid fraction (unsaturated acids, mainly
oleic acids) and a solid fraction (saturated acids,
mainly stearic acids).
Separation
• used to separate a mixture of fatty acids into fatty
acids of a more specific chain length.
Fractional
distillatio
n
Fractionation
Hydrogenation
Palm Oil
Coconut Oil
Inedibile
Animal Fats
Fish Oils
Corn Oil
Cottonseed
Oil
Vegetable Oil
Soybean Oil
Fatty Acid
Cutting oils, special
lubrucants, rolling oils
Fatty Amines
-sulfo fatty acid
Polymer
Fatty Ester
Nonamethylene diamine,
Undecy acid
Fatty Alcohol
Soap
Salt formation
Hydrogenation
Oxidation
Esterification
Polymerization
-sulfonylation
Amination
Reaction with Sulfur
& Sulfur chlorides
Sources & Uses of Fatty
Acids
1) Esterification of Fatty Acids
Fatty Acid Derivatives
Catalyst: 1-3 % sulfuric acid/hydrogen chloride
Alcohol: monohydric/polyhydric
2) Reaction with Ammonia  Fatty Amines
Fatty Acid Derivatives
3) Hydrogenation  Fatty Alcohol
Fatty Acid Derivatives
Operational Parameters:
T = 300oC ; P = 30 - 80 bar
Catayst: copper chromite
C8H17CH=CHC7H14COOH  HOOC(CH2)7COOH + C8H17COOH
Azelaic acid and pelargonic acid are used in the vinyl plasticizers
industry and in synthetic lubricants.
4) Oxidation of Fatty Acids
Fatty Acid Derivatives
Fatty Acid Derivatives
5) Reaction with Chloride (SOCl2)  Acid Chloride
FATTY ESTER
 Fatty Acid Methyl Ester/ Fatty Acid Ester– alkanoate or ester
Molecular Formula : CH3(CH2)nCOOCH3
General : R-COO-CH3
Structural Formula :
Types of Fatty Esters
Isopropyl Esters
Ethylexyl Esters
Butyl Esters
Glycerol Esters
Glycol Esters
Methyl Esters
Polyol Esters
• FAME is produced by
transesterification or
esterification.
• In the transesterification
process a glyceride reacts with
an alcohol in the presence of a
catalyst, forming a mixture of
FAME and an glycerol.
• alkaline catalysts are used with
sodium methylate (most
effective) NaOH can also be
used
FATTY ACID METHYL ESTER
(FAME)
Transesterification
 In the esterification process a fatty acid reacts with an alcohol on the
present of a catalyst, forming a mixture of FAME or Fatty acid ester and
water
• acid catalysts like sulfuric acid are
employed
FATTY ACID
METHYL ESTER
(FAME)
Esterification
 Ester from monohydric alcohol is used in the cosmetics and plasticizer
industries
 Ester from polyhydric alcohol:
i. glycol diester  vinyl plasticizer
ii. monoester
iii. glyceride
iv. triolein
 surface-active agent
 surface-active agent
 plasticizer
Uses of Fatty Esters
Applications
• cosmetics,
toiletries,
pharmaceuticals,
food, metal
working fluids, and
etc.
• as antifoaming
agents,
emulsifiers,
thickening agents
in ointment.
• with desirable
characteristics
such as high
thermal and
oxidation stability
and low volatility.
Synthethic
lubricants
In
pharmaceutical
s
As diesel
substitutes for
taxis, buses,
lorries and
tractors, etc.
Variety
industrial
applications
FATTY ALCOHOL
 Fatty Alcohol – alcoholate
Molecular Formula : CH3 (CH2)nCH2OH (n=4-20)
General : R-COH
Structural Formula :
Production
Process (Acid
Route)
• direct hydrogenation of fatty acids is not
used in a large commercial scale due to
higher reaction temperatures resulting in
lower yield & damaging effects of FA on
the catalyst.
Production
Process (Ester
Route)
• using the suspension process or the fixed
bed process (depending on the method by
which the catalyst is employed)
• copper chromite (CuCr) catalyst also
converts any unsaturated carbon double
bonds so that only saturated fatty alcohols are
formed.
• if unsaturated fatty alcohols are desired,
zinc chromite catalyst is employed
FATTY ALCOHOL
 Fatty alcohols and their derivatives are used at about 70% in
surface active substances
 It is due to its ampliphilicity characteristic thus, fatty alcohols
can orient themselves at interfaces, which allows their use in
emulsions and micro-emulsions
 Therefore most fatty alcohol been used as a surfactant
Types of fatty alcohol and its group of
surfactant
• nonionic surfactants
• anionic surfactants
Fatty alcohol
polyglycolethers, fatty
alcohol ethoxilates
Fatty alcohol sulfates
and Fatty alcohol ether
sulfates
• cationic surfactants
Alkyl methylammonium
chlorides
• non-ionic surfactants
Alkyl polyglucosides
(APG)
Applications
Cosmetic
Pharmaceutic
al cream and
ointments
Ethoxylated
sulphate
Textile
auxiliaries
Detergent Plasticizer
Shampoo
Concrete
additives
Pest control
formulation
FATTY AMINE / FATTY
NITROGEN
Types of Fatty
Amine
Fatty Amine Production
Fatty Amine Production
Applications
GLYCEROL
 Glycerol– esters of glycerol with alkanoate or carboxylate
Molecular Formula : C3H8O3
Classification: Polyol
Structural Formula :
Production Of Glycerol
1) Hydrolysis
• They are hydrolyzed into their constituents (fatty acids and glycerol) by the
action of super heated steam, acid, alkali or enzyme (e.g., lipase of
pancreas).
• During their enzymatic and acid hydrolysis glycerol and free fatty acids are
produced
2) Saponification
 Alkaline hydrolysis produces glycerol and salts of fatty acids (soaps).
 Soaps cause emulsification of oily material this help easy washing of the
fatty materials
3) Transesterification
 Triglycerides are treated with an alcohol such as ethanol with catalytic
base to give ethyl esters of fatty acids and glycerol
Glycerol Derivatives
Applications

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oleochemical products.pptx

  • 1. PTT 259: OLECHEMICA L PROCESS & PRODUCTS OLEOCHEMIC AL PRODUCTS
  • 3. OLEOCHEMICALS Hydrolysis is a basic process which the fat and oil (triglyceride)are splitting into crude glycerol and mixture of crude fatty acid
  • 6. Fatty Acid  Fatty acid (FA) is produced via hydrolysis process of fat with water. Molecular Formula : CnH2nO2 General : R-COOH Structural Formula :
  • 7. Sources & Uses of Fatty Acids Source • Fatty acids from plant and animal: oil palm, coconut, corn, soybean, sunflower, fish • Synthetic fatty acids are derived from petrochemical. Uses • Petrochemical industry: tire industry, soap, detergent, fatty alcohol, polymer, fatty amines, cosmetic, pharmacy.
  • 8. Process (from crude FA) • used to purify the crude fatty acids under vacuum. Distillatio n • increases the melting point of the fatty acids. Hydrogenation is the conversion of unsaturated acids into saturated acids. Hydrogenation • yields a liquid fraction (unsaturated acids, mainly oleic acids) and a solid fraction (saturated acids, mainly stearic acids). Separation • used to separate a mixture of fatty acids into fatty acids of a more specific chain length. Fractional distillatio n
  • 11. Palm Oil Coconut Oil Inedibile Animal Fats Fish Oils Corn Oil Cottonseed Oil Vegetable Oil Soybean Oil Fatty Acid Cutting oils, special lubrucants, rolling oils Fatty Amines -sulfo fatty acid Polymer Fatty Ester Nonamethylene diamine, Undecy acid Fatty Alcohol Soap Salt formation Hydrogenation Oxidation Esterification Polymerization -sulfonylation Amination Reaction with Sulfur & Sulfur chlorides Sources & Uses of Fatty Acids
  • 12. 1) Esterification of Fatty Acids Fatty Acid Derivatives Catalyst: 1-3 % sulfuric acid/hydrogen chloride Alcohol: monohydric/polyhydric
  • 13. 2) Reaction with Ammonia  Fatty Amines Fatty Acid Derivatives
  • 14. 3) Hydrogenation  Fatty Alcohol Fatty Acid Derivatives Operational Parameters: T = 300oC ; P = 30 - 80 bar Catayst: copper chromite
  • 15. C8H17CH=CHC7H14COOH  HOOC(CH2)7COOH + C8H17COOH Azelaic acid and pelargonic acid are used in the vinyl plasticizers industry and in synthetic lubricants. 4) Oxidation of Fatty Acids Fatty Acid Derivatives
  • 16. Fatty Acid Derivatives 5) Reaction with Chloride (SOCl2)  Acid Chloride
  • 17. FATTY ESTER  Fatty Acid Methyl Ester/ Fatty Acid Ester– alkanoate or ester Molecular Formula : CH3(CH2)nCOOCH3 General : R-COO-CH3 Structural Formula :
  • 18. Types of Fatty Esters Isopropyl Esters Ethylexyl Esters Butyl Esters Glycerol Esters Glycol Esters Methyl Esters Polyol Esters
  • 19. • FAME is produced by transesterification or esterification. • In the transesterification process a glyceride reacts with an alcohol in the presence of a catalyst, forming a mixture of FAME and an glycerol. • alkaline catalysts are used with sodium methylate (most effective) NaOH can also be used FATTY ACID METHYL ESTER (FAME)
  • 21.  In the esterification process a fatty acid reacts with an alcohol on the present of a catalyst, forming a mixture of FAME or Fatty acid ester and water • acid catalysts like sulfuric acid are employed FATTY ACID METHYL ESTER (FAME)
  • 23.  Ester from monohydric alcohol is used in the cosmetics and plasticizer industries  Ester from polyhydric alcohol: i. glycol diester  vinyl plasticizer ii. monoester iii. glyceride iv. triolein  surface-active agent  surface-active agent  plasticizer Uses of Fatty Esters
  • 24. Applications • cosmetics, toiletries, pharmaceuticals, food, metal working fluids, and etc. • as antifoaming agents, emulsifiers, thickening agents in ointment. • with desirable characteristics such as high thermal and oxidation stability and low volatility. Synthethic lubricants In pharmaceutical s As diesel substitutes for taxis, buses, lorries and tractors, etc. Variety industrial applications
  • 25. FATTY ALCOHOL  Fatty Alcohol – alcoholate Molecular Formula : CH3 (CH2)nCH2OH (n=4-20) General : R-COH Structural Formula :
  • 26. Production Process (Acid Route) • direct hydrogenation of fatty acids is not used in a large commercial scale due to higher reaction temperatures resulting in lower yield & damaging effects of FA on the catalyst.
  • 27. Production Process (Ester Route) • using the suspension process or the fixed bed process (depending on the method by which the catalyst is employed) • copper chromite (CuCr) catalyst also converts any unsaturated carbon double bonds so that only saturated fatty alcohols are formed. • if unsaturated fatty alcohols are desired, zinc chromite catalyst is employed
  • 28. FATTY ALCOHOL  Fatty alcohols and their derivatives are used at about 70% in surface active substances  It is due to its ampliphilicity characteristic thus, fatty alcohols can orient themselves at interfaces, which allows their use in emulsions and micro-emulsions  Therefore most fatty alcohol been used as a surfactant
  • 29. Types of fatty alcohol and its group of surfactant • nonionic surfactants • anionic surfactants Fatty alcohol polyglycolethers, fatty alcohol ethoxilates Fatty alcohol sulfates and Fatty alcohol ether sulfates • cationic surfactants Alkyl methylammonium chlorides • non-ionic surfactants Alkyl polyglucosides (APG)
  • 31. FATTY AMINE / FATTY NITROGEN Types of Fatty Amine
  • 35. GLYCEROL  Glycerol– esters of glycerol with alkanoate or carboxylate Molecular Formula : C3H8O3 Classification: Polyol Structural Formula :
  • 36. Production Of Glycerol 1) Hydrolysis • They are hydrolyzed into their constituents (fatty acids and glycerol) by the action of super heated steam, acid, alkali or enzyme (e.g., lipase of pancreas). • During their enzymatic and acid hydrolysis glycerol and free fatty acids are produced
  • 37. 2) Saponification  Alkaline hydrolysis produces glycerol and salts of fatty acids (soaps).  Soaps cause emulsification of oily material this help easy washing of the fatty materials
  • 38. 3) Transesterification  Triglycerides are treated with an alcohol such as ethanol with catalytic base to give ethyl esters of fatty acids and glycerol