Professional Documents
Culture Documents
Hawkins
Managing Director
5 basic oleochemicals:
fatty acids
fatty alcohols
fatty methyl esters
fatty amines
glycerine
esterification
Partial glycerides
Glycerine
Triacetine
splitting
esterification
ethoxylation
Oils
&
Fats
Fatty
Acids
neutralization
Soaps
amination
Fatty Amines
esterification
a
hydrogenation
trans-esterification
F.A. ethoxylates
Fatty Acid
Methyl
Esters
Fatty
Alcohol
c
d
amidation
direct hydrogenation
Alkyl chlorides
F. OH ethoxylates
F.OH sulfates
Esters
F.A. Alkanolamides
Fatty Alcohols
Lubricants
Detergents
Plasticizer
Cosmetics
Palm Oil (PO)- Primarily derived from the palm oil plantations
in Malaysia and Indonesia is the major feedstock in Asia.
Carboxylic Acids
R
COOH
C
OH
Alcohols
OH
Amines
NH2
OH
H
R
COOR1
Esters
R
C
H
R1
Intermediates
Soap
Plasticizer
Fatty Acids
Lubricants
Cosmetics
O
R
C
OH
Splitting
Hydrogenation
Distillation
Different Process
Twitchell
used catalyst
Continuos
Colgate-Emery higher T & P than Twitchell
Enzymatic
lipases
limited interest to date
Catalysts used
Ni on silica powder; slurry phase
Pd on C powder; slurry phase
Pd on C; fixed bed
Reactor systems
low pressure/
hydrogen shortage
Ni(fa)2 + H2
Ni + 2 ffa
high pressure/
abundance of hydrogen
100 m/g Ni
+ ffa
+ Ni-soaps
- ffa
used
catalyst
10-20 m/g Ni
Dissolved Ni (ppm)
25
20
Ni + 2H+ = Ni2+ + H2
15
10
Ni2+ = K.(H+)2/H2
5
0
0
30 bar
0.1
10 bar
0.2
0.3
0.4
0.5
0.6
2 bar
final iodine
value
100
10
presumable
course
1
1
10
pore size diameter (nm)
Soybean soap stock fatty acids, 15 bar, 200C
100
95
90
85
80
75
70
65
60
55
50
50
time (min)
100
Ni residues
Environment
4
Fresh
Catalyst
5
Customers
process
3
Precious
metal
salt solution
1
Precious
metal
6
Spent
catalyst
2
Precious
metal
sponge
9
Precious
metal ash
refining
7
Incineration
spent
catalyst
8
Precious
metal ash
unsat FA
Surfactants
80%
Shampoo
Powders
Bath gels
etc
Fatty
Alcohols
Emulsifying
agents
Cosmetics
Lubricants
in polymer processing
O
R
C
OH
Catalysts used:
CuCr
CuZn
CuSi
Raney Cu
Gas phase FB
2900-3600psi; 230-250C
Trickle-bed
2900-4350psi; 250 C
100-150C; 20-50bar
Intermediates
Fatty
M.E.
Biodiesel
O
R
C
H
R1
RCOOCH2
RCOOCH
RCOOCH2
CH2OH
+ 3CHOH
NaOCH3
3RCOOCH3 + CHOH
methyl ester
CH2OH
cetane (C16)
biodiesel
Growth industry due to:
green movement and agricultural incentives in Europe
agricultural lobby and aim for domestic fuel production in
USA
H
R
Most uses depend on the cationic nature of the amine
Corrosion
Inhibitors
Fatty
Amines
Sanitizing
Agents
Organoclays
Fabric
Softeners
Lubricant
Additive
Primary amine
R-NH2
Secondary amine
R2NH
Tertiary amine
R3N
Catalyst choice
Raney Ni
Supported Ni powders
NH3
Fatty nitriles
Al2O3
Fatty acids
Raney
Saturated
primary amine
Ni(P)
Unsaturated
primary amine
Saturated and
unsaturated
secondary
amines
Ni(D)
Dialkyl
monomethyl
tertiary amine
Ni(D)
Formaldehyde
Temp (C)
Pressure
(bar)
Primary
80-150
10-550
Secondary
150-200
50-200
Tertiary
160-230
7 - 14
nickel, cobalt
Unsaturated
similar to above
Catalysts
copper
chromite,
nickel
powder
Special Conditions
R-COOH + NH3
R-COONH4
ammonium salt
R-COONH4
R-CONH2 + H2O
amide
R-CONH2
R-CN + H2O
R-CN + 2H2
FATTY AMINES
nitrile
R-CN + H2
R-CH=NH
imine
R-CH=NH + H2
imine
R-CH2NH2
R-CH=NH + R-CH2NH2
imine
R-CH-NH-CH2-R
NH2
1-aminodialkylamine
R-CH-NH-CH2-R
NH2
1-aminodialkylamine
- NH3
R-CH=N-CH2-R
imine
R-CH=N-CH2-R
imine
+H2
R-CH2-NH-CH2-R
secondary amine
R-CH-NH-CH2-R
NH2
+H2
1-aminodialkylamine
- NH3
R-CH2-NH-CH2-R
secondary amine
Personal Care
Food
Glycerine
Explosives
Pharmaceutical
Tobacco