Chemistry of Fats and Oils - ITUkaraali/AKFatsOilsChem.pdfChemistry of Fats and Oils Prof. Dr....
54
Chemistry of Fats and Oils Prof. Dr. Artemis Karaali Food Engineering Department Istanbul Technical University ITU January 24, 2006
Transcript of Chemistry of Fats and Oils - ITUkaraali/AKFatsOilsChem.pdfChemistry of Fats and Oils Prof. Dr....
Che
mis
tryof
Fat
san
dO
ilsP
rof.
Dr.
Arte
mis
Kar
aali
Food
Engi
neer
ing
Dep
artm
ent
Ista
nbul
Tech
nica
lUni
vers
ityIT
UJa
nuar
y24
, 200
6
Con
tent
s
1.In
trodu
ctio
n 2.
Com
mon
Pro
perti
esof
Fat
san
dO
ils2.
Maj
orC
onst
ituen
tsof
Fat
san
doi
ls:
Che
mis
try o
f Trig
lyce
rides
and
Fatty
Aci
ds3.
Rea
ctio
nsof
Fat
san
dO
ils4.
Min
orC
onst
ituen
tsof
Fat
san
dO
ils5.
Con
clus
ion
Intro
duct
ion
Fats
and
oils
are
bio
chem
ical
uni
ts s
ynth
esiz
edby
plan
tsan
dan
imal
san
dm
ade
upof
mos
tlyca
rbon
, hyd
roge
nan
dox
ygen
elem
ents
.
They
are
the
mos
tcal
orie
-den
se o
f all
the
nutri
ents
foun
din
food
s:
~9kc
al/g
and
cont
ribut
ero
ughl
y30
-50%
of o
urda
ilyca
lorie
inta
ke.
They
impr
ove
pala
tibili
tyof
food
sby
mod
ifyin
gfla
vour
and
text
ure
They
are
inso
lubl
e in
wat
er b
ut s
olub
le in
mos
t org
anic
sol
vent
s.
They
are
gre
asy
to th
e to
uch,
and
hav
e lu
bric
atin
g pr
oper
ties.
They
are
not
read
ily v
olat
ile.
Whe
nbu
rntt
hey
do n
ot le
ave
any
resi
due.
They
hav
e lo
wer
den
sitie
s th
an w
ater
.At
nor
mal
room
tem
pera
ture
s th
eyra
nge
in c
onsi
sten
cy fr
om li
quid
s to
sol
ids.
Whe
n so
lids,
they
are
refe
rred
to a
s “fa
ts” a
nd w
hen
liqui
d th
ey a
re c
alle
d “o
ils.”
Che
mic
alPr
oper
ties
They
belo
ngto
the
uppe
rcla
ssof
bio
chem
ical
com
poun
dskn
own
as “L
ipid
s”.
Inad
ditio
nto
fats
and
oils
, the
term
lipid
sal
soin
clud
em
ono-
and
digl
ycer
ides
, pho
spha
tides
, ce
rebr
osid
es, s
tero
ls, t
erpe
nes,
fatty
alc
ohol
s,
fatty
aci
ds, f
at-s
olub
le v
itam
ins,
and
sim
ilar
subs
tanc
esth
atar
eal
sofo
und
in m
inor
amou
nts
in fa
tsan
doi
ls.
Trig
lyce
rides
The
maj
oran
dpr
edom
inan
tcom
pone
ntof
fats
and
oils
are
triac
ylgl
cero
lsor
‘trig
lyce
rides
’.A
“trig
lyce
ride”
is a
n es
ter o
f gl
ycer
ol a
nd th
ree
fatty
ac
ids.
O
H2C
O
H
HC
O
H
H2C
O
H
HO
C
R
HO
C
R
HO
C
R
OO O
H2C
O
C
R
O OH
2C
O
C
R
HC
O
C
R
++
3 H
2O
TRIG
LYC
ERID
ESW
hen
all o
f the
thre
efa
tty a
cids
in a
trig
lyce
ride
are
iden
tical
,it i
s te
rmed
a “s
impl
e”tri
glyc
erid
e.
The
mor
e co
mm
on fo
rms,
how
ever
, are
the
“mix
ed”
trigl
ycer
ides
in w
hich
two
or th
ree
kind
s of
fatty
aci
dsar
e pr
esen
t in
the
sam
etri
glyc
erid
em
olec
ule.
MixedTriglyseride
SimpleTriglyseride
FATT
Y A
CID
STh
em
ajor
porti
onof
the
trigl
ycer
ide
mol
ecul
eis
mad
eup
of fa
ttyac
ids:
One
hun
dred
gr
ams
of fa
t or o
il co
ntai
nsap
prox
imat
ely
95 g
ram
s of
fatty
ac
ids.
Both
the
phys
ical
and
che
mic
al
char
acte
ristic
s of
fats
are
in
fluen
ced
grea
tly b
y th
e ki
nds
and
prop
ortio
ns o
f the
com
pone
nt
fatty
aci
ds a
nd th
e w
ay in
whi
ch
thes
e ar
e po
sitio
ned
on th
e tri
glyc
erid
em
olec
ule.
Fatty
Aci
dsTh
e pr
edom
inan
t fat
ty a
cids
foun
din
mos
ted
ible
oils
are
satu
rate
d an
d un
satu
rate
d ca
rbon
cha
ins
with
an
even
num
ber o
f ca
rbon
ato
ms
and
a si
ngle
car
boxy
l gro
up.
Fatty
aci
ds c
an b
e cl
assi
fied
acco
rdin
g to
th
eir d
egre
e of
‘sat
urat
ion’
.
Satu
rate
dvs
. Uns
atur
ated
Fatty
Aci
dsFa
tty a
cids
con
tain
ing
only
satu
rate
d(s
ingl
eca
rbon
-to-c
arbo
n)
bond
sar
eca
lled
“sat
urat
ed”.
Fatty
acid
sco
ntai
ning
one
or m
ore
doub
leca
rbon
-to-c
arbo
n b
onds
are
te
rmed
“uns
atur
ated
.”
The
Iodi
nenu
mbe
ror(
Iodi
neVa
lue)
is u
sed
toas
sess
the
degr
eeof
uns
atur
atio
nof
fatty
acid
sin
fats
and
oils
sinc
e io
dine
will
add
toth
eir
doub
lebo
nds
in p
ropo
rtion
with
unsa
tura
tion,
IV b
eing
high
erin
hi
gher
degr
ees
of u
nsat
urat
ion.
Com
mon
Nam
eSy
stem
atic
Nam
eFo
rmul
a
But
yric
aci
d(4
C)
n-bu
tano
ic
Cap
roic
acid
(6C
)n-
hexa
noic
Cap
rylic
acid
(8C
)n-
octa
noic
Cap
ricac
id(1
0C)
n-de
cano
ic
Laur
icac
id(1
2C)
n
-dod
ecan
oic
CH
3(C
H2)
2COO
H
CH
3(C
H2)
4COO
H
CH
3(C
H2)
6COO
H
CH
3(C
H2)
8COO
H
CH
3(C
H2)
10CO
OH
Com
mon
Satu
rate
d Fa
tty A
cids
:C
omm
onSa
tura
ted
Fatty
Aci
ds:
Com
mon
Nam
eSy
stem
atic
Nam
eFo
rmul
a
Myr
istic
acid
(14C
)n-
tetra
deca
noic
Palm
itic
acid
(16C
)n-
hexa
deca
noic
Stea
ricac
id(1
8C)
n-oc
tade
cano
ic
Ara
chid
icac
id(2
0C)
n-ei
cosa
noic
Beh
enic
acid
(22C
)n-
doco
sano
ic
Lign
ocer
icac
id(2
4C)
n-te
traco
sano
ic
CH
3(C
H2)
12CO
OH
CH
3(C
H2)
14CO
OH
CH
3(C
H2)
16CO
OH
CH
3(C
H2)
18CO
OH
CH
3(C
H2)
20CO
OH
CH
3(C
H2)
22CO
OH
Com
mon
Mon
ouns
atur
ated
Fatty
Aci
ds(M
onoe
noic
-MU
FA)
Com
mon
Nam
eSy
stem
atic
Nam
e ci
s
Myr
isto
leic
9-te
trade
ceno
icac
id
Palm
itole
ic9-
hexa
dece
noic
acid
Ole
ic9-
octa
dece
noic
acid
Eruc
ic13
-doc
osen
oic
acid
Com
mon
Poly
unsa
tura
ted
Fatty
Aci
ds(P
olye
noic
-PU
FA)
Com
mon
Nam
eSy
stem
atic
Nam
e Li
nole
ic:
9,12
-oct
adec
adie
noic
aci
d(2
doub
lebo
nds)
Lino
leni
c:9,
12,1
5-oc
tade
catri
enoi
c ac
id(3
dou
ble
bond
s)
Ara
chid
onic
:5,
8,11
,14-
eico
sate
traen
oic
acid
(4 d
oubl
ebo
nds)
Lino
leic
and
linol
enic
acid
s ar
e ca
lled
“ess
entia
lfat
tyac
ids”
beca
use
they
can
not
be s
ynth
esiz
ed b
y th
e hu
man
body
and
mus
t be
supp
lied
in th
e di
et. A
rach
idon
icac
id c
an b
e sy
nthe
size
d by
the
body
from
die
tary
lino
leic
acid
. Th
ese
acid
sar
eco
nsid
ered
esse
ntia
l bec
ause
they
are
eith
eran
ess
entia
l co
mpo
nent
of m
embr
anes
or
prec
urso
r of a
gro
up o
f hor
mon
e-lik
e co
mpo
unds
ca
lled
eico
sano
ids
incl
udin
g pr
osta
glan
dins
, thr
ombo
xane
s, a
nd p
rost
acyc
lins
whi
ch a
re im
porta
nt in
the
regu
latio
n of
wid
ely
dive
rse
phys
iolo
gica
l pro
cess
es.
Rec
omm
ende
d D
ieta
ry A
llow
ance
s fo
rdie
tary
lino
leic
acid
nec
essa
ry to
pre
vent
es
sent
ial f
atty
aci
d de
ficie
ncy
in h
uman
s is
roug
hly
1 to
2%
of t
otal
die
tary
ca
lorie
s.
“Om
ega”
Fat
tyA
cids
H C H
2C H 2
C H 2
C H 2
C H 2
C H 2
C O H
O C H
3 ( C H 2 ) 7
H C C
ω
1 9
γβ
αC
2H om
ega
9 -o
ctad
ecen
oic
acid
The
“om
ega”
or “n
-”cl
assi
ficat
ion
orno
men
clat
ure
forf
atty
acid
s: T
he
term
s “o
meg
a”or
“n-”
refe
r to
the
posi
tion
of th
e do
uble
bon
d of
the
fatty
ac
id c
lose
st to
the
met
hyl e
nd o
f the
mol
ecul
e.
Thus
, ole
ic a
cid
whi
ch h
as it
s do
uble
bon
d on
the
9th
carb
on fr
om th
e m
ethy
l end
is c
onsi
dere
d an
om
ega-
9 (o
r an
n-9)
fatty
aci
d.
Nut
ritio
nally
mor
esi
gnifi
cant
omeg
afa
ttyac
ids:
Om
ega-
3 P
UFA
Isom
eris
min
Fat
tyA
cids
Isom
ers
are
chem
ical
com
poun
ds c
ompo
sed
of th
esa
me
elem
ents
com
bine
din
the
sam
epr
opor
tions
, thu
sha
ving
the
sam
e cl
osed
mol
ecul
ar fo
rmul
ae b
ut w
ith a
diff
eren
t ar
rang
emen
tof t
heir
cons
titue
nt a
tom
s.
Thes
e di
ffere
nces
may
resu
lt fro
m d
iffer
ent c
arbo
n sk
elet
ons(
bran
ched
orst
raig
htch
ain)
,diff
eren
t pos
ition
s of
do
uble
bon
ds, o
rsom
eot
herd
iffer
ent a
rran
gem
ents
of t
he
atom
s in
spa
ce.
The
two
impo
rtant
type
s of
isom
eris
m a
mon
g fa
tty a
cids
are
:(1
) pos
ition
al(2
) geo
met
ric
Posi
tiona
lIso
mer
ism
Whe
n tw
o fa
tty a
cids
are
iden
tical
exc
ept f
or th
e po
sitio
n of
th
e do
uble
bon
d, th
ey a
re re
ferre
d to
as
‘pos
ition
al is
omer
s’.
Exam
ple:
Pet
rose
linic
and
olei
cac
ids
Petro
selin
icac
idis
an
18C
fatty
acid
pres
enti
n pa
rsle
ysee
doi
lwith
a si
ngle
doub
lebo
ndat
6th
car
bon
(6-o
ctad
ecen
oic
acid
) whe
reas
itspo
sitio
nali
som
erol
eic
acid
is a
gain
an 1
8C
mon
ouns
atur
ated
acid
with
itssi
ngle
doub
lebo
ndat
the
9th
carb
on(9
-oct
adec
enoi
cac
id).
Geo
met
ric Is
omer
ism
Uns
atur
ated
fatty
aci
ds c
an e
xist
in
eith
er th
e ci
sor
tran
s fo
rm d
epen
ding
on
the
conf
igur
atio
n of
the
hydr
ogen
at
oms
atta
ched
toth
e ca
rbon
ato
ms
join
ed b
y th
e do
uble
bon
ds.
If th
e hy
drog
en a
tom
s ar
e on
the
sam
e si
de o
f the
car
bon
chai
n, th
e ar
rang
emen
t is
calle
d ci
s.
If th
e hy
drog
en a
tom
s ar
e on
op
posi
te s
ides
of t
he c
arbo
n ch
ain,
th
e ar
rang
emen
t is
calle
d tra
ns.
Geo
met
ric Is
omer
ism
Geo
met
ric Is
omer
ism
With
two
doub
le b
onds
, fo
ur g
eom
etric
isom
ers
are
poss
ible
:
1. A
llci
s:ci
s-ci
s,2.
cis
-tran
s,
3. tr
ans-
cis,
4.
All
trans
:tra
ns-tr
ans.
Fatty
Aci
dC
ompo
sitio
ns*
of C
omm
onFa
tsan
dO
ils
* : a
s %
of t
otal
fatty
acid
s
Ana
lysi
sof F
atty
Aci
ds(F
AM
E*)
1
FAM
E*:
Fat
tyA
cid
Met
hylE
ster
s
Trig
lyce
rides
Fats
and
oils
are
pra
ctic
ally
alw
ays
mix
ture
s of
tri
glyc
erid
es in
var
ying
pro
porti
ons.
In s
ome
fats
on
e tri
glyc
erid
epr
edom
inat
es, i
n ot
hers
sev
eral
ar
e pr
esen
t in
near
lyeq
uala
mou
nts.
App
aren
tly
no n
atur
al fa
t or o
il co
nsis
ts s
olel
y of
a s
ingl
e tri
glyc
erid
e.
The
trigl
ycer
ides
of
seve
n ac
ids
(laur
ic, m
yris
tic,
palm
itic,
ole
ic, l
inol
eic
and
linol
enic
) mak
e up
the
grea
t bul
k of
the
natu
ral f
ats
and
oils
.
Trig
lyce
rides
Nat
ural
trigl
ycer
ide
mol
ecul
es c
onta
inbo
th s
atur
ated
and
uns
atur
ated
fa
tty a
cids
.D
epen
ding
on
the
type
of f
atty
aci
ds in
the
mol
ecul
e, tr
igly
cerid
es c
an
be c
lass
ified
as
mon
o-, d
i-, a
nd tr
iuns
atur
ated
orm
ono-
, di-,
and
trisa
tura
ted.
The
degr
eeof
uns
atur
atio
nof
the
trigl
ycer
ide
is th
usre
late
dto
the
num
bero
f dou
ble
bond
spr
esen
tin
itsfa
ttyac
idco
mpo
nent
s.
Trig
lyce
rides
Phy
sica
l pro
perti
es o
f trig
lyce
rides
dep
end
very
muc
hon
thei
r fat
ty a
cid
com
pone
nts:
Mel
ting
poin
t of t
hefa
toro
ilin
crea
ses
as th
e nu
mbe
r of
car
bons
in th
e hy
droc
arbo
n ch
ains
incr
ease
s an
d as
the
num
ber o
f dou
ble
bond
s de
crea
ses.
Thi
sis
w
hy:
-trig
lyce
rides
rich
in u
nsat
urat
ed fa
tty a
cids
are
ge
nera
lly li
quid
at r
oom
tem
pera
ture
,-tr
igly
cerid
es ri
ch in
sat
urat
ed fa
tty a
cids
are
ge
nera
lly s
emis
olid
s or
sol
ids
at ro
om te
mpe
ratu
re.
Trig
lyce
rides
•In
trigl
ycer
ides
rich
in s
atur
ated
fatty
ac
ids:
•sa
tura
ted
hydr
ocar
bon
chai
ns c
an li
e pa
ralle
l and
pac
k in
to w
ell-o
rder
ed,
com
pact
cry
stal
line
form
s.•
ther
e ar
e st
rong
dis
pers
ion
forc
es
betw
een
thei
r cha
ins;
ther
efor
eth
ey
have
mel
ting
poin
ts a
bove
room
te
mpe
ratu
re(s
olid
)
•In
trigl
ycer
ides
rich
in u
nsat
urat
ed fa
tty
acid
s:•
the
hydr
ocar
bon
chai
ns h
ave
a le
ss
orde
red
stru
ctur
ebe
caus
e of
the
kink
yco
nfig
urat
ion
of th
e do
uble
bon
ds,
•di
sper
sion
forc
es b
etw
een
unsa
tura
ted
hydr
ocar
bon
chai
ns a
re w
eake
r; th
ese
trigl
ycer
ides
ther
efor
eha
ve m
eltin
g po
ints
bel
ow ro
om te
mpe
ratu
re(li
quid
)
kink
Rea
ctio
nsof
Fat
sand
Oils
a.R
eact
ions
in th
eca
rbox
ylic
grou
p
b.R
eact
ions
in th
efa
ttyac
idch
ain
a
b
a.1.
Hyd
roly
sis
Trig
lyce
rides
can
be b
roke
ndo
wn
toth
eirc
onst
ituen
tsby
chem
ical
agen
ts(o
rby
enzy
mes
-lipa
ses-
as in
the
dige
stiv
etra
cts
of
hum
ans
and
anim
als)
. Par
tial h
ydro
lysi
s of
trig
lyce
rides
will
yiel
d m
ono-
and
digl
ycer
ides
and
fatty
aci
ds.
Hyd
roly
sis
Whe
n th
e hy
drol
ysis
of a
trig
lyce
ride
is c
arrie
d to
com
plet
ion
with
wat
er in
the
pres
ence
of a
n ac
id o
rbas
eca
taly
st, t
he
mon
o-, d
i-, a
nd tr
igly
cerid
es w
ill hy
drol
yze
to y
ield
gly
cero
l an
d fa
tty a
cids
.
A tr
iacy
lgly
cero
l(a
trig
lyce
ride
)
CH
2O
-CR
O O
O
CH
2O
-CR
''
1.
Na
OH
, H
2O
2.
HC
l, H
2O CH
2O
H
CH
2O
H
1,2
,3-P
ropa
netr
iol
(Gly
cero
l, gl
ycer
in)+
RC
O2
H
R'C
O2
H
R''
CO
2H
Fatty
aci
ds
HO
CH
R'C
O-C
H
a.2.
Sapo
nific
atio
n•
Nat
ural
soa
ps a
re p
repa
red
by b
oilin
g fa
ts(i.
e. la
rd o
r ot
her a
nim
al fa
ts)w
ith N
aOH
, in
a re
actio
n ca
lled
sapo
nific
atio
n(s
apo:
soa
pin
Lat
in)
Sodi
um s
oaps
1,2,
3-Pr
opan
etri
ol(G
lyce
rol;
Gly
ceri
n)
+
sapo
nifi
catio
n+
O
CH
OH
CH
2O
H
CH
2O
H
3N
aO
H
3R
CO
-
Na
+A
tria
cylg
lyce
rol
(a tr
igly
ceri
de)
CH
2O
-C
R
O O
O
CH
2O
-C
R
RC
O-
CH
Soap
sSo
aps
clea
n by
act
ing
as
emul
sify
ing
agen
ts:
the
long
hyd
roph
obic
hy
droc
arbo
n ch
ains
of s
oaps
ar
e in
solu
ble
in w
ater
and
tend
to
clu
ster
in s
uch
a w
ay a
s to
m
inim
ize
thei
r con
tact
with
w
ater
the
pola
r hyd
roph
ilic c
arbo
xyla
tegr
oups
tend
to re
mai
n in
co
ntac
t with
the
surr
ound
ing
wat
er m
olec
ules
driv
en b
y th
ese
two
forc
es, s
oap
mol
ecul
es s
pont
aneo
usly
cl
uste
r int
o “m
icel
les”
•W
hen
soap
is m
ixed
with
wat
er-
inso
lubl
e gr
ease
, oil,
and
fat
stai
ns, t
he n
onpo
larp
arts
of t
he
soap
mic
elle
s “d
isso
lve”
no
npol
ardi
rt m
olec
ules
and
th
ey a
re c
arrie
d aw
ay in
the
pola
r was
h w
ater
that
diss
olve
sth
epo
lar c
arbo
xyla
tepa
rts.
Synt
hetic
Det
erge
nts
The
desi
gn c
riter
ia fo
r a g
ood
dete
rgen
t are
•a
long
hyd
roca
rbon
tail
of 1
2 to
20
carb
ons
•an
da
pola
r hea
d gr
oup,
just
like
soap
s.Th
e m
ost w
idel
y us
ed s
ynth
etic
det
erge
nts
are
the
linea
r al
kylb
enze
nesu
lfona
tes
(i.e.
Sod
ium
dode
cylb
enze
nesu
lfona
te)
a.3.
Este
rific
atio
nsE
ster
ifica
tion
is th
ere
vers
eof
hyd
roly
sis:
a p
roce
ssw
here
an a
lcoh
ol (i
.e.g
lyce
rol)
is re
acte
d w
ith a
n ac
id(i.
e.fa
tty
acid
)to
form
an
este
r (i.e
.mon
o-, d
i-, a
nd tr
igly
cerid
es).
Ther
ear
em
any
diffe
rent
type
sof
est
erifi
catio
nre
actio
ns:
Exa
mpl
e: A
lcoh
olys
is: A
n al
coho
l suc
h as
gly
cero
l is
reac
ted
with
fat o
r oil
to p
rodu
ce e
ster
s su
ch a
s m
ono-
and
digl
ycer
ides
. U
sing
the
est
erifi
catio
npr
oces
ses,
edi
ble
acid
s, fa
ts, a
nd
oils
can
be
reac
ted
with
edi
ble
alco
hols
to p
rodu
ce u
sefu
l ed
ible
ingr
edie
nts
(i.e.
emul
sifie
rs) a
ndal
sobi
odie
self
uels
as w
illla
terb
e ex
plai
ned
in m
uch
grea
terd
etai
ldur
ing
the
cour
se.
Inte
rest
erifi
catio
nIn
tere
ster
ifica
tion,
whi
chis
the
rear
rang
emen
tor a
re
dist
ribut
ion
of th
e fa
tty a
cids
on
the
trigl
ycer
ide,
is
acc
ompl
ishe
d by
cat
alyt
ic m
etho
ds a
t rel
ativ
ely
low
tem
pera
ture
s.Th
e pr
edom
inan
t com
mer
cial
app
licat
ion
for
inte
rest
erifi
catio
nis
the
prod
uctio
n of
spe
cial
ty
fats
for t
he c
onfe
ctio
nery
and
mar
garin
e in
dust
ries.
Thi
s pr
oces
s pe
rmits
furth
er ta
ilorin
g of
tri
glyc
erid
e pr
oper
ties
to a
chie
ve th
e re
quire
d st
eep
mel
ting
curv
es.
Inte
rest
erifi
catio
nsw
ithin
a si
ngle
trigl
ycer
ide
orbe
twee
ntri
glyc
erid
es
With
ina
sing
letri
glyc
erid
e:
Betw
een
2 tri
glyc
erid
es;
Sta
rt w
ith:
End
with
:
Enzy
mat
icIn
tere
ster
ifica
tions
By
utili
zing
enzy
mes
in p
lace
of c
hem
ical
s,
the
oils
are
subj
ecte
dto
less
seve
re
proc
essi
ngco
nditi
ons.
Enz
yme
inte
rest
erifi
catio
nis
eco
nom
ical
, in
crea
ses
proc
essi
ngfle
xibi
lity,
frie
ndly
for
the
envi
ronm
ent,
and
also
prov
ides
num
erou
sde
sire
dfu
nctio
nalc
hara
cter
istic
s.
Tran
sest
erifi
catio
nTh
e tra
nses
terif
icat
ion
proc
ess
conv
erts
trig
lyce
ride
este
rs
into
alk
yl e
ster
s b
y m
eans
of a
cat
alys
t (ly
e) a
nd a
n al
coho
l re
agen
t, us
ually
met
hano
l, w
hich
yie
lds
met
hyl e
ster
s(
biod
iese
l), t
he m
etha
nol r
epla
cing
the
glyc
erin
e.
In tr
anse
ster
ifica
tion,
the
lye
cata
lyst
first
brea
ks th
e bo
nds
hold
ing
the
fatty
aci
d ch
ains
to th
e gl
ycer
ine;
the
glyc
erin
e fa
lls a
way
, the
fatty
aci
d ch
ains
then
bon
d w
ith th
e m
etha
nol.
The
trigl
ycer
ide
mol
ecul
e is
turn
edin
toth
ree
sepa
rate
met
hyl
este
r mol
ecul
es p
lus
glyc
erin
e as
a b
y-pr
oduc
t.
b.1.
Hyd
roge
natio
nH
ydro
gena
tion
is th
e pr
oces
s by
whi
ch
hydr
ogen
is a
dded
dire
ctly
to p
oint
s of
un
satu
ratio
nin
the
fatty
aci
dch
ainn
ess
(of
trigl
ycer
ides
).
Why
hyd
roge
nate
?
Impa
rts p
last
icity
Im
prov
es te
xtur
e(c
ryst
al s
truct
ure)
Incr
ease
s ve
rsat
ility
in fo
od a
pplic
atio
nsIn
crea
ses
stab
ility
of o
ilsIn
crea
ses
mel
ting
rang
eIm
prov
es fl
avou
rsta
bilit
y
Hyd
roge
natio
nH
ydro
gen
gas
is
reac
ted
with
the
doub
le b
onds
of t
he
unsa
tura
ted
fatty
aci
dsof
oils
at e
leva
ted
tem
pera
ture
san
d pr
essu
re in
the
pres
ence
of a
cat
alys
t(i.
e.ni
ckel
).
Hyd
roge
natio
nof
Ole
icA
cid
Hyd
roge
natio
nH
ydro
gena
tion
cond
ition
s ca
n be
var
ied
by th
e m
anuf
actu
rer t
o m
eet c
erta
in p
hysi
cal a
nd
chem
ical
cha
ract
eris
tics
desi
red
in th
e fin
ishe
d pr
oduc
t. Th
is is
ach
ieve
d th
roug
h se
lect
ion
of th
e pr
oper
te
mpe
ratu
re, p
ress
ure,
tim
e, c
atal
yst,
and
star
ting
oils
. B
oth
posi
tiona
l and
geo
met
ric (t
rans
) iso
mer
s ar
e fo
rmed
to s
ome
exte
nt d
urin
g hy
drog
enat
ion,
the
amou
nts
depe
ndin
g on
the
cond
ition
s em
ploy
ed.
b.2.
Oxi
datio
nO
xida
tion
of fa
tsan
doi
lsth
atis
indu
ced
by a
ir at
room
te
mpe
ratu
re is
refe
rred
to a
s “a
utox
idat
ion.
” Th
is is
a s
low
pro
cess
in w
hich
oxyg
en re
acts
with
un
satu
rate
d fa
tty a
cids
and
whe
rein
itial
lype
roxi
des
are
form
edas
“prim
ary
oxid
atio
npr
oduc
ts”w
hich
in tu
rn b
reak
do
wn
to h
ydro
carb
ons,
ket
ones
, ald
ehyd
es, a
s w
ella
s ep
oxid
esan
d al
coho
lsas
“sec
ondr
yox
idat
ion
prod
ucts
”.Th
e re
sult
of th
e au
toxi
datio
nof
fats
and
oils
is th
e de
velo
pmen
t of o
bjec
tiona
ble
flavo
rsan
d od
ors
char
acte
ristic
of
the
cond
ition
kno
wn
as “o
xida
tive
ranc
idity
.”
Ran
cidi
ty
Def
initi
on:F
orm
atio
nof
off
flavo
rsan
dod
ors
from
brea
kdow
nof
fats
Ran
cidi
ttyof
fats
and
oils
are
of tw
oty
pes:
Hyd
roly
ticor
enzy
mat
icra
ncid
ity:R
esul
ting
mos
tlyin
hy
drol
ysed
shor
tcha
infa
ttyac
ids
(i.e.
mos
tcom
mon
in
butte
rand
choc
olat
e)
Oxi
dativ
era
ncid
ity: a
dditi
onof
oxy
gen
todo
uble
bond
sof
oi
ls, r
esul
ting
in s
mal
lcha
inox
ygen
ated
com
poun
dslik
epe
roxi
des,
ald
ehyd
es, k
eton
es(i.
e. M
ostc
omm
onin
po
lyun
satu
rate
doi
ls).
Acc
eler
atin
gFa
ctor
s: d
egre
eof
uns
atur
atio
n,he
at, l
ight
and
pres
ence
of m
etal
s
Stab
ility
of F
atsa
ndO
ilsSt
abili
tySt
abili
tySt
abili
tyof
of
of
Fat
sFa
tsFa
tsan
dan
dan
dO
ilsO
ilsO
ils
Stab
ility
is d
efin
edas
the
resi
stan
ceof
a fa
tor
oilt
ora
ncid
ity.
Oxi
dativ
est
abilit
ym
aybe
ass
esse
dby
dete
rmin
ing
pero
xide
valu
e, a
nisi
dine
valu
e, o
rin
duct
ion
perio
dof
oils
oroi
l-bea
ring
mat
eria
ls.
Hyd
roly
ticst
abilit
yis
ass
esse
dby
dete
rmin
atio
nof
free
fatty
acid
s(FF
A) o
raci
dva
lue
in th
eoi
lor
fat.
How
How
totoPr
even
tPr
even
t // Con
trol
Con
trol R
anci
dity
Ran
cidi
ty
Dea
ctiv
atio
nas
tohe
at, l
ight
and
moi
stur
ein
han
dlin
gan
dst
orag
e
Ant
ioxi
dant
addi
tives
BH
A, B
HT
Toco
pher
ols
Hyd
roge
natio
nR
emov
eun
satu
ratio
n
b.3.
Poly
mer
isat
ion
All
com
mon
ly u
sed
fats
and
oils
, par
ticul
arly
thos
e hi
gh in
pol
yuns
atur
ated
fatty
aci
ds,t
end
to fo
rm
som
e la
rger
mol
ecul
es k
now
n br
oadl
y as
po
lym
ers
whe
n he
ated
und
er e
xtre
me
cond
ition
s of
tem
pera
ture
(250
-275
°C)a
nd ti
me.
P
olym
ers
in fa
ts a
nd o
ils a
rise
by fo
rmat
ion
of
eith
er c
arbo
nbr
idge
s(ca
rbon
to c
arbo
n bo
nds)
or
oxyg
en b
ridge
s be
twee
n m
olec
ules
. The
seca
n oc
cur p
artic
ular
ly d
urin
g de
ep fa
t fry
ing.
The
fato
roi
lfirs
tpol
ymer
izes
to d
imer
san
dtri
mer
s, a
ndth
ento
high
er p
olym
ers.
Prod
uctio
nTe
chno
logy
forO
ilsan
dFa
tsPr
oduc
tion
Prod
uctio
nTe
chno
logy
Tech
nolo
gyfo
rfo
r Oils
Oils
and
and
Fats
Fats
Afte
robt
aini
ngth
ecr
ude
oilo
rfat
from
the
plan
tora
nim
alra
wm
ater
ials
, mos
tcru
defa
tsan
doi
lsar
eno
t in
a st
ate
that
will
allo
wth
emto
be d
irect
lyco
nsum
edsi
nce
they
also
cont
ain
man
yun
desi
rabl
eim
purit
ies.
Ref
inin
g: T
reat
men
tsap
plie
dto
crud
eoi
lsor
fats
tom
ake
them
acce
ptab
lefo
rhum
anco
nsum
ptio
n.
Itm
ayco
nsis
tof a
sim
ple
alka
line
was
hing
(neu
tralis
atio
n)fo
llow
edby
dryi
ngan
dfil
tratio
n, o
rit m
ayin
volv
eso
me
othe
rsta
ges
like
blea
chin
g, w
inte
risat
ion
and
deod
oriz
atio
nbe
fore
mar
ketin
g fo
rhum
anco
nsum
ptio
n.
Min
orC
onst
ituen
tsin
Fat
sand
Oils
Inad
ditio
nto
trigl
ycer
ides
, all
fats
and
oils
cont
ain
som
eno
ngly
cerid
es, t
hem
ajor
ones
bein
gst
erol
s, p
hosp
hatid
es, v
itam
ins
and
pigm
ents
.
Thes
eno
n-tri
glyc
erid
eco
mpo
nent
sar
efo
und
in v
ario
ustra
ceam
ount
sin
the
unsa
poni
fiabl
epo
rtion
of th
efa
toro
ilan
dar
equ
itech
arac
teris
ticfo
reac
hso
urce
.
Ster
ols
Ster
ols,
ors
tero
idal
coho
ls, a
rea
clas
sof
su
bsta
nces
that
cont
ain
the
com
mon
ster
oid
nucl
eus
plus
an
8 to
10 c
arbo
nsi
dech
ain
and
an a
lcoh
olgr
oup.
In
anim
alfa
ts“c
hole
ster
ol”i
s th
eon
lyst
erol
, whe
reas
in
vege
tabl
eoi
lsth
eyar
equ
itenu
mer
ous
and
are
calle
dun
dert
hege
nera
l nam
e of
“p
hyto
ster
ols”
.
Phos
phat
ides
Phos
phat
ides
cons
ist
of a
lcoh
ols
(usu
ally
glyc
erol
), co
mbi
ned
with
fatty
acid
s,
phos
phor
icac
id,
and
a ni
troge
n-co
ntai
ning
com
poun
d(lik
ech
olin
e).
Leci
thin
and
ceph
alin
are
mos
tco
mm
onph
osph
atid
esfo
und
in
edib
lefa
ts.
Ref
inin
gre
mov
esal
mos
tall
the
phos
phat
ides
from
the
fato
roil.
CH
2
CH
CH
2
OO
O O
OP
OC
H2
CH
2N
(C
H3
)3
O O-
+
palm
itic
acid
stea
ric
acid
glyc
erol
chol
ine
Leci
thin
Oil-
solu
ble
Vita
min
sTh
ough
gene
rally
not a
ric
hso
urce
forv
itam
ins,
ve
geta
ble
oils
cont
ain
sign
ifica
ntam
ount
sof
to
coph
erol
s( w
ithVi
tam
in E
act
ivity
) and
β-ca
rote
nes
(Vita
min
A
prec
urso
r) as
pig
men
ts.
Fats
from
land
and
mar
ine
anim
als
cont
ain
subs
tant
iala
mou
nts
of
Vita
min
sD
and
A.
Futu
rePr
ospe
ctsa
ndC
oncl
usio
nFu
ture
Futu
rePr
ospe
cts
Pros
pect
san
dan
dC
oncl
usio
nC
oncl
usio
n
Agric
ultu
ral
biot
echn
olog
yha
s be
ensu
cces
sful
lyap
plie
dto
achi
eve
mod
ifica
tions
in t
hech
emis
tryof
fat
san
doi
ls:
The
typi
calo
ilsde
rived
from
biot
echn
olog
ical
mea
nsar
ehi
ghan
dm
idol
eic
sunf
low
er, l
owlin
olen
ic/lo
wsa
tura
teso
ybea
ns, h
igh
linol
eic
flaxs
eed
oil,
low
linol
enic
cano
la, h
igh
laur
ate
cano
la,
high
olei
cca
nola
, and
high
stea
rate
cano
la.
Gen
etic
ally
mod
ified
oils
of
the
futu
rew
illlik
ely
have
cust
omiz
edfa
ttyac
idco
mpo
sitio
nsto
achi
eve
impr
oved
nutri
ent
prof
iles:
red
uctio
nin
sat
urat
edfa
ttyac
idco
nten
t, im
prov
edox
idat
ive
stab
ility
resu
lting
in a
red
uced
need
for
hydr
ogen
atio
n, r
educ
edca
lorie
sor
bioa
vaila
bilit
y, c
reat
ion
of
spec
ific
fatty
acid
prof
iles
forp
artic
ular
food
appl
icat
ions
, and
crea
tive
“func
tiona
l” fo
ods
for
the
popu
latio
nas
wel
las
for
spec
ific
med
ical
and
indu
stria
lpu
rpos
es.
Ref
eren
ces f
orFa
tsan
dO
ilsC
hem
istry
Ref
eren
ceR
efer
ence
s s fo
rfo
r Fat
sFa
tsan
dan
dO
ilsO
ilsC
hem
istry
Che
mis
try
1.Fo
od L
ipid
sby
Cas
imir
C. A
koh
and
Dav
id B
. Min
, Mar
cel
Dek
ker,
Inc.
New
Yor
k, N
Y.1
998
2.
Bai
ley'
s Ind
ustr
ial O
ils a
nd F
at P
rodu
ctsb
y Y
.H. H
uiW
iley
Inte
rsci
ence
. New
Yor
k, N
Y. 1
996
3.
Foo
d C
hem
istr
yby
O. F
enne
ma,
Mar
cel D
ekke
r, In
c.N
ew Y
ork,
NY
.199
8
4.Fo
odFa
tsan
dO
ilsby
Inst
itute
of S
horte
ning
and
Edi
ble
Oils
, 8t
h
Editi
on, 1
999.
