Asn Xuat Nitrobensen

O AN TOT NGHIEP
San Xuat Nitrobenzen
Thiet Ke Phan Xng
MUC LUC

MUC LUC.............................................................................1
GII THIEU CHUNG............................................................3
Chng I :TNH CHAT CUA NGUYEN LIEU VA SAN
PHAM..................................................................................4
I. Tnh chat cua nguyen lieu.......................................4
A. Tnh chat cua benzen ...............................................4
1. Cau tao cua vong benzen ..............................4
2. Tnh chat vat ly cua benzen ..........................5
3. Tnh chat hoa hoc cua benzen .......................6
B. Tnh chat cua axit nitric.............................................8
1. Tnh chat vat ly cua axit nitrric......................8.
2. Tnh chat hoa hoc cua axit nitrric...................9
C. Tnh chat cua axit sulfuric.......................................11
1. Tnh chat vat ly cua axit sulfuric..................11
2. Tnh chat hoa hoc cua axit sulfuric ..............11
D. Tnh chat cua Na2CO3..............................................13
1. Tnh chat vat ly cua Na2CO3.........................13
2. Tnh chat hoa hoc cua Na2CO3......................13
II. Tnh chat cua san pham.......................................14
1. Tnh chat vat ly cua nitrobenzen ................14
2. Tnh chat hoa hoc cua nitrobenzen...............15
Chng II : CAC PHNG PHAP SAN XUAT NITROBENZEN
........18
1. Nitro hoa bang axit HNO3........................................18
2. Nitro hoa bang axit HNO3 + H2SO4...........................18
3. Nitro hoa bang muoi cua HNO3............................19
4. Nitro hoa bang khi co them HCH3COO hay alhydricaxetic..........................................................................19
5. Nitro hoa bang phng phap the cac nhom sulfo,
amino, diazo bang nhom NO2...............................20
6. Nitro hoa bang oxit nit...........................................20
7. Nitro hoa bang oxit nit co mat H2SO4.................22
8. Nitro hoa bang HNO3 vi s tach nc phan ng
.................................................................................... 22
SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.
O AN TOT NGHIEP
Thiet Ke Phan Xng
Chng III : SAN XUAT NITROBENZEN TRONG CONG

NGHIEP.............................................................................. 24
I. Qua trnh nitro hoa...................................................24
II. Ly thuyet chung........................................................25
1. Ban chat tac nhan nitro hoa..............................25
2. C che phan ng nitro hoa bang hon hp H 2SO4 +
HNO3 ..........................................................................28
3. ong hoc phan ng qua trnh nitro hoa bang
hon hp HNO3 + H2SO4............................................31
4. Qua trnh phu khi nitro hoa ....................................33
5. Nhng yeu to anh hng en qua trnh nitro
hoa ........................................................................... 34
III. Ky thuat san xuat qua trnh nitro hoa ..............38
1. Thiet b nitro hoa ................................................38
2. Chuan b hon hp nitro hoa .............................41
3. San xuat nhng hp chat nitro ........................45
IV.San xuat nitrobenzen ..............................................46
1. S o san xuat nitrobenzen bang phng phap
lien tuc hai bac...............................................................46
2. S o nitro hoa benzen theo Katter.......................47
3. S o san xuat nitrobenzen cua Nga.................47
4. S o san xuat nitrobenzen theo phng phap
lien tuc ............................................................................48
Chng IV. TNH TOAN THIET KE...................................54
I. Tnh can bang vat chat thiet b nitro hoa ........54
1. Lng vat chat vao thiet b phan ng...........55
2. Lng vat chat ra khoi thiet b phan ng......56
II. Tnh can bang nhiet lng thiet b nitro hoa.......57
1. Nhiet lng do nguyen lieu mang vao................58
2. Nhiet lng do nc lanh mang vao....................59
3. Nhiet lng do qua trinh nitro hoa sinh ra...........59
4. Nhiet lng do nc lanh mang ra........................59
5. Nhiet lng do san pham mang ra.......................59
6. Nhiet lng mat mat ra moi trng..................60
KET LUAN........................................................................62
TAI LIEU THAM KHAO....................................................63
O AN TOT NGHIEP
Thiet Ke Phan Xng
GII THIEU CHUNG
Cac san pham hoa hoc noi chung va ac biet

la cac san pham cua nganh cong nghe tong hp
hu c noi rieng, ong vai tro quan trong trong i
song cung nh trong s phat trien cua nen kinh te
quoc dan. Cac san pham nay c san xuat chu
yeu t nguyen lieu ban au la than a va dau mo,
qua nhieu qua trnh che bien hoa hoc khac nhau, tao
nen cac hp chat hu c trung gian. Nitrobenzen la
mot trong cac san pham trung gian o.Do nhu cau
cua con ngi ngay cang cao, cho nen viec tongr hp
ra hp chat nitrobenzen la het sc can thiet. No
chiem mot v tr quan trong trong nganh cong nghiep
hoa chat cua nc ta hien nay .
Nitrobenzen co rat nhieu ng dung. Phan ln
c dung e tong hp anilin, benzidin, dinitrobenzen,
thuoc nhuom Mot lng nho nhng khong kem
phan quan trong dung e lam dung moi chon loc, san
xuat thuoc no va dung trong y dc.
en nay, nitrobenzen van c san xuat theo mot
phng phap duy nhat la nitro hoa benzen vi qui mo
ln va kha hoan thien ve mat ky thuat. Nguyen
lieu chu yeu la benzen , con tac nhan nitro hoa co
the co nhieu loai nh axit nitric, muoi nitrat, oxit nit
Nhng trong cong nghiep hien nay hau nh ch s
dung tac nhan nitro hoa la hon hp axit nitric va axit
sulfuric, ngoai ra co s dung natricacbonat va nc.
Do s a dang ve nhng ng dung quan trong cua
nitrobenzen va do cac nguyen lieu au cho san xuat
nitrobenzen eu khong phai nguyen lieu nhap ngoai
nen viec thiet ke mot day chuyen san xuat
nitrobenzen la can thiet. Co nh vay mi tao ra c
nhieu san pham ng dung trong cac nganh cong
O AN TOT NGHIEP
Thiet Ke Phan Xng
nghiep a nc ta dan dan tien en mot nen cong

nghiep hoa hoc tien tien hien ai.
Chng I.
TNH CHAT CUA NGUYEN LIEU VA SAN PHAM.
A. TNH CHAT CUA NGUYEN LIEU.
I.Tnh chat cua benzen [ 1 120 ].

Benzen co cong thc hoa hoc la C 6H6 . Benzen la
mot hydrocacbon thm trang thai long, khong mau,
linh ong, co chiet suat cao, co mui thm ac biet.
Benzen khong tan trong nc, nhng tan trong ru, ete,
dau hoa. Benzen hoa tan c nhieu chat nha, m,
lu huynh va nhieu chat khac khong tan trong nc.
Do o benzen la mot dung moi rat thong dung.
Benzen la nguon nguyen lieu quan trong trong cong
nghiep pham nhuom anilin, dc pham, trong viec san
xuat chat phu e nang cao ch so octan oi vi
nhien lieu ong c oto va may bay.Nam 1825
Faraday la ngi tm ra benzen . Benzen c tach t
chat long ngng tu bang cach nen kh dau mo.Nam
1845 A.W.Hofman thu c benzen t au nhe trong nha
than.
1. Cau tao cua vong benzen [ 2 12 ].
O AN TOT NGHIEP
Thiet Ke Phan Xng
*Theo quan iem co ien: phan t benzen co

cau tao mach vong khep kn. Nhieu tac gia a e
ngh cac cong thc cau tao cua vong benzen, trong
o co cong thc Kekule
c s dung nhieu hn
ca. Mac du vay, cong thc Kekule khong phan anh
c ay u cac tnh chat cua benzen.
Theo quan iem hien ai: Benzen co cau tao
vong 6 canh phang. Cac nguyen t cacbon trong vong
eu trang thai lai hoa sp2 . Moi nguyen t cacbon
con mot electron p cha lai hoa. Sau electron p cua 6
nguyen t cacbon khong xen phu eu ca hai ben tao
ra am may electron p phan bo eu tren ca 6
nguyen t cacbon cua vong va c bieu dien bang
cong thc sau:
Cac goc hoa tr eu bang 1200 .

C
C
C
C
o dai kien ket C C co gia tr trung gian gia

lien ket n C C va lien ket oi C = C
C
C
1,54 A0
C
1,40 A0
C
1,34 A0
Chung ta de dang nhan thay rang do cac

electron p xen phu khep kn nen cac lien ket C C
cua vong khong mang tnh chat cua mot lien ket
oi C = C. Phan t benzen co mat o electron p phan
bo eu, phan t hoan toan oi xng, ben, v the
O AN TOT NGHIEP
Thiet Ke Phan Xng
ma kho cong hp, kho oxi hoa. No ch de pha v

cau truc ben cua vong.
2 .Tnh chat vat ly cua benzen [ 6 ].
Di ay la cac thong so vat ly cua benzen:
iem nong chay
5,5330C
iem soi
80,10C
Khoi lng rieng 25oC:
879 kg/m3
o nht 200C
0,649.10-3 N.s/m2
Sc cang be mat 200C
29.10-3 N/m
Nhiet dung rieng 200C
1730 J/kg.o
Nhiet o chp chay coc kn

11,1 C.
Nhiet
chay
9,999 kcal/mol.
ang
ap
Nhiet hoa hi
Nhiet
538 C.
25oC
8.09kcal/kmol.
boc
chay
trong
khong
kh
Nhiet
289.45oC.
o
hoa
0.18g/100g H20.
o
tan
ti
trong
nc
han
Ap suat ti han
25oC
48.6
atm
Nhiet nong chay
o
hoa
0.05g/100g C6H6.
Nhiet
2,351 kcal/mol.
tan
30,1 kcal/kmol.
cua
lng
nc
nong
Ty trong ti han
trong
benzen
chay
0,3
g/ml.
O AN TOT NGHIEP
Thiet Ke Phan Xng
Hang so vat ly mot so hydrocacbon thm [ 1 ] :

Cong
thc
C6H6
Ten goi
Benzen
C6H5CH3
Toluen
tnc0C
tsoi0C
+5,5
80,1
Para-xilen
C6H5C2H5
Meta-xilen
110,6
0,8669
138,4
0,8610
144,4
0,8802
139,1
0,8641
136,2
0,8669
-95
C6H5(CH3)2 Xilen
Octo-xilen
Ty
khoi
0,8790
+13,
2
-29,0
Etylbenzen
-53,6
-94,0
3. Tnh chat hoa hoc cua benzen [ 2 ].

a.
Phan ng cong hp :
Kho thc hien, oi hoi ieu kien khac nghiet
: nhiet o, xuc tac, ap suat.
+ Phan ng kh :
+ 3H2
Ni,200 - 3000C,300 atm
benzen
xyclohexan
Cl
CH
+ Tac dung vi clo :

Cl CH
CH-
nhiet o, ap
Cl CH
suat
Cl
anh
sang
SV: Pham Ngoc HpLp: Hoa Dau - K44.
CH
Cl
+ 3 CI2
CH
O AN TOT NGHIEP
Thiet Ke Phan Xng
a. Phan ng oxi hoa : Rat kho thc hien.

Cac chat oxi hoa thong thng nh KMNO 4 ,K2Cr2O7
/ H2SO4 khong co kha nang oxi hoa nhan benzen.
nhiet o cao, benzen b oxi hoa bi oxi tao anhydric
maleic vi s co mat cua xuc tac V2O5 :
O
CH
4500C
V2O5
benzen
C
9/2O2
CH
O
anhydricax
etic
b.Phan ng the electrophyl SE :

phan ng halogen hoa :
X
FeX
+ X2 3
+ HX ; (X =
Cl, Br)
Phan ng nitro hoa :
H2SO4
NO2
O AN TOT NGHIEP
Thiet Ke Phan Xng
+ HNO3
55 600C
Phan ng sulfo hoa :
+
+ H2 O
SO3H
H2SO4
H2O
Phan ng ankyl hoa :
R
AlCl3
+ RCl
O
C R
Phan ng axyl hoa :

O
+
HCl
R C ClAlCl+3
HCl
II.Tnh chat cua axit nitric [ 3 134 ], [ 4 183 ].

Axit nitric co cong thc phan t HNO3 la mot axit
manh c dung lam tac nhan nitro hoa benzen e
san xuat nitrobenzen.
trang thai hi, phan t axit nitric co cau tao
phang.
O
0
0,96 A
0
102
O
1,21 A0
1160
0
130
N
0
1,41114
A0
O AN TOT NGHIEP
Thiet Ke Phan Xng
I. Tnh chat vat ly cua axit nitric.

ieu kien thng axit nitric la chat long
khong mau, boc khoi manh trong khong kh. Axit nitric
ac tan trong nc theo bat k ty le nao. No tao nen
vi nc hon hp ong soi cha 69,2% axit va soi
121,80C di ap suat thng.
Axit nitric tinh khiet kem ben, de b phan huy
di tac dung cua anh sang va nhiet :
4 HNO3
4 NO2
+ O 2 + 2 H 2O
Kh NO2 sinh ra lai tan vao axit nitric lam cho chat
long t khong mau tr nen co mau vang.
Ban than axit nitric tinh khiet t ion hoa nh sau :
2 HNO3
NO2+
+ NO3- +
H2O
Trong o nong o cua moi loai ion la 0,5 mol/lt

nhiet o 100C.
Khi tan trong dung moi co kha nang cho proton
manh hn, nh axit sulfuric va axit pecloric, axit nitric phan
ly cho ion nitroni NO2+ :
HNO3
+
NO 2+
2HClO4
2ClO4-
H3O+
4HNO3 +
2H2SO4
4NO2+ + 2HSO4- +
H3O+
Qua trnh phan ly nay tao nen nhieu ion nitroni
hn s t ion hoa cua axit nitric.
Mot so tnh chat vat ly cua axit nitric [6] :
Nhiet o soi
82,60C
Nhiet o ket tinh
-41,590C
Khoi lng rieng 200C
1512,8 kg/m3
Ch so khuc xa nD25
1,397
o nht 200C
0,8.10-3 N.s/m2+
Nhiet tao thanh pha long
2,7474 J/g
10
O AN TOT NGHIEP
Thiet Ke Phan Xng
Nhiet tao thanh pha kh
2,1258 J/g
Nhiet hoa hi 200C
626,3 J/g
1.748 j/g.o
Nhiet nong chay
600 kcal/kmol
2.Tnh chat hoa hoc cua axit nitric :

Axit nitric la axit manh, tng oi t ben, oxi hoa
manh va la tac nhan nitric hoa.
a. Tac dung vi kim loai :
Axit nitric co the tng tac vi hau het kim loai
tr Au, Pt, Rh, Ta va Ir. Tuy thuoc vao nong o cua
axit, nhiet o va ban chat cua kim loai ma san
pham thu c la HNO2, NO2, N2O, N2 , NH4+ .
Noi chung nhng kim loai co the ien cc kha
nho hn the ien cc cua hidro se kh axit nitric en
N2O, N2, NH4+ .
V du :
4Zn + 10HNO3(loang)
4Zn(NO3)2 +
NH4NO3
+ 3H2O
Nhng kim loai khac kh axit nitric ac en NO 2
va kh axit nitric loang en NO.
V du :
3CU
8HNO3(loang)
3CU(NO3)2
2NO
Pb
4HNO3(ac)
Pb(NO3)2
2NO2
4H2O
2H2O
ieu la la mot so kim loai thong thng nh Fe,
Al, va Cr khong nhng khong tng tac vi axit nitric
ac ma con c axit o thu ong hoa (do tao
thanh mang oxit rat mong va kho tan).
b. Tac dung vi phi kim :
Axit nitric co the oxi hoa c mot so nguyen to
khong kim loai nh C, P, As, S len so oxi hoa cao nhat :
11
O AN TOT NGHIEP
+
S
Thiet Ke Phan Xng
2HNO3(loang)
6HNO3(ac)
H2SO4
=
H2SO4
2 NO
+
4NO2
2H2O
Giong vi axit nitr, axit nitric ac oxi hoa ion Fe 2+
en ion Fe3+ con ban than axit c kh en NO. Khi
co d ion Fe2+, NO se ket hp vi ion o cho hp chat
mau nau va kem ben :
6FeSO4 + 3H2SO4 + 2HNO3 =
4H2O
FeSO4
+ NO
3Fe2(SO4)3
NO
[Fe(NO)]SO4
Khac vi axit nitr, axit nitric loang khong oxi hoa

c HI en I2. Tuy nhien axit ac oxi hoa c khong
nhng HI ma ca HCl :
HNO3(ac)
3HCl
NO
Cl 2
2H2O
Hon hp cua mot the tch axit nitric ac va ba
the tch axit clohidric ac c goi la cng thuy, no
co the hoa tan c ca vang va Platin.
3Pt + 4HNO3 + 12HCl = 3PtCl4 + 4NO + 8H2O
PtCl4
2HCl
H2[PtCl6]
Axit cloroplatinic
Axit nitric tinh khiet hon hp vi axit sunfuric ac

la tac nhan nitro hoa cac hp chat hu c mach
vong thm.
V du :
H
+
H2SO4
NO
+2
H NO2
H2 O
12
O AN TOT NGHIEP
Thiet Ke Phan Xng
II.Tnh chat cua axit sulfuric [3 117],[4 230]

Axit sulfuric (H2SO4) c s dung nh mot chat
xuc tac trong qua trnh nitro hoa ong thi con tao
ieu kien cho viec s dung axit nitric triet e hn.
1. Tnh chat vat ly cua axit sulfuric.
Axit sulfuric la mot chat long nang (d = 1,827
g/cm ), sanh nh dau, khong co mau va mui, cac
phan t lien hp vi nhau bang lien ket hidro, ong
ac 10,370C va soi kem theo s phan huy
khoang 2800C. Hon hp ong soi ap suat 1 atm
cha 98,2% H2SO4 soi 3380C.
3
Axit sulfuric tan vo han trong nc va qua trnh tan

o toa rat nhieu nhiet. V vay khi pha loang can
phai o dan dan axit vao nc ong thi khuay
eu, tuyet oi khong c o nc vao axit.
Axit sulfuric co kha nang hut nc manh nen
thng c dung nh mot chat lam kho.
2. Tnh chat hoa hoc cua axit sulfuric.
Axit sulfuric co nhng tnh chat hoa hoc chu yeu
sau : axit manh, oxi hoa, sulfo hoa, hidrat hoa. Trong
dung dch nc axit sulfuric la axit manh nac ien ly
au tien, nac th hai no ien ly yeu hn :
H2SO4
H+
HSO-4
HSO-4
H+
SO-4
Axit sulfuric tinh khiet la dung moi ion hoa ( = 100

250C). Ban than axit cung t ion hoa theo s o :
H2SO4
H2SO4
H3SO4+ + HSO4-
Axit sulfuric ac nong oxi hoa c ca nhng kim

loai kem hoat
ong nh ong, bac, thuy ngan (0 > 0) va san pham
s kh H2SO4 la SO2.
13
O AN TOT NGHIEP
Thiet Ke Phan Xng
V du :
2 H2SO4
Cu
CuSO 4
SO2
2H2O
Vi cac kim loai hoat ong, san pham s kh
axit sulfuric ngoai SO2 con tao thanh S, H2S.
V du :
Mg
2H 2SO4
3Mg
4H2SO4
4Mg
5H2SO4
MgSO 4
SO2
3MgSO4
4MgSO 4
+ H2S
2H2O
4H2O
+
4H2O
Axit sulfuric nong o ln hn 65%, nguoi khong
tac dung vi sat.
Vi mot so phi kim nh P, S, C b axit sulfuric ac
nong oxi hoa en oxit hoac axit tng ng.
V du :
2 H2SO4
3SO2
2H2O
Tnh chat sunfo hoa cac hp chat hu c vong

thm cua axit sulfuric ac the hien phan ng :
Ar H
HSO4
2H 2SO4
ArSO 3H
H3O+
Cuoi cung axit sulfuric ac la tac nhan hidrat

hoa, no co the hoa than gluxit.
V du :
(C6H10O5)n
H2SO4 . 5nH2O
H2SO4
6nC
Trai vi axit ac, axit sulfuric loang khong tac

dung vi phi kim va ch phan ng vi nhng kim loai
co the kh am va san pham s kh axit la kh
hidro :
14
O AN TOT NGHIEP
Zn
Thiet Ke Phan Xng
H2SO4
ZnSO4
H2
II.Tnh chat cua Na2CO3 [ 6 ] , [ 4 147 ].

Natri cacbonat hay soda (Na2CO3) c dung lam
chat trung hoa axit d.
1. Tnh chat vat ly cua Na2CO3.
Nhng thong so vat ly cua Na2CO3 :
Khoi lng rieng 200C
2533 kg/m3
Nhiet o nong chay
8540C.
Khoi
105.99 kg/kmol.
lng
Ty
2.533 g/cm3.
trong
Nhiet
10.676 j/g.
phan
20oC
tao
Nhiet nong chay

kcal/kg.o
thanh
7000 kcal/kmol
0,2493
Natri cacbonat khan la chat bot mau trang, hut

am. No de tan trong nc, qua trnh tan phat ra nhieu
nhiet do s tao thanh cac hidrat. T dung dch
nhiet o di 32,50C, natri cacbonat ket tinh di dang
ecahidrat Na2CO3.10 H2O. ay la nhng tinh the n ta
trong suot, khong mau, de tan trong nc va nong
chay trong nc ket tinh 32,50C. Gia nhiet o o
va 35,40C, no mat nc bien thanh heptahidrat
Na2CO3.7 H2O, tren 35,40C bien thanh monohidrat
Na2CO3.H2O va en 1070C mat nc hoan toan bien
thanh soda khan. o tan cua cac hidrat cha nhieu
phan t nc tang len theo nhiet o, con o tan
cua monohidrat giam xuong. Khi e trong khong kh,
ecahidrat mat bt nc ket tinh tr nen trang vun.
2. Tnh chat hoa hoc cua Na2CO3.
15
O AN TOT NGHIEP
Thiet Ke Phan Xng
Khi tan trong nc, natri cacbonat b thuy phan lam

cho dung dch co phan ng kiem :
Na2CO3
H2O
NaHCO3
NaOH
Tac dung vi voi toi :
Na2CO3
CaCO3
Ca(OH)2
2NaOH
Tac dung vi CO2 va H2O :
Na2CO3
CO2
H2O
2NaHCO3
B. TNH CHAT CUA SAN PHAM.

Nitrobenzen co cong thc phan t C6H5NO2, la
hp chat nitro thm n gian nhat. Chat long nh dau.
Nitrobenzen c ieu che bang cach dung hon hp
HNO3 va H2SO4 e nitro hoa benzen. Dung lam nguyen
lieu e san xuat anilin, benzidin, thuoc nhuom, dung
moi va chat oxi hoa.
1.Tnh chat vat ly cua nitrobenzen :
Nitrobenzen tinh khiet la chat long khong mau
(nitrobenzen cong nghiep co mau vang), co mui
hanh nhan, oc, t tan trong nc, co the bay hi theo
hi nc. Nitrobenzen de tan c trong hau het cac
dung moi hu c va tan lan vi benzen moi ty le.
Nitrobenzen la mot dung moi hu c tot co the hoa
tan c AlCl3.
Nhng thong
nitrobenzen :
so
vat
ly
+ Nhiet o nong chay
quan
trong
cua
5,850C
+ Nhiet o soi
101 kPa
210,90C
13 kPa
139,90C
4 kPa
108,20C
0,13 kPa
53,10C
+ Ty trong
16
O AN TOT NGHIEP
Thiet Ke Phan Xng
d41,5
1,344
d410
1,213
d415,5
1,208 - 1,221
d425
1,119
+ o nht (150C)
2,17.10-2 mPa.s
+ Sc cang be mat (200C)
43,35 mN/m
+ Hang so ien moi

200C
35,97
1700C
18,15
+ Nhiet dung rieng (300C)
14,18 J/g
+ Nhiet nong chay
94,1 J/g
+ Nhiet hoa hi
331 J/g
+ Nhiet o chp chay coc kn
880C
+ Nhiet o t boc chay
4820C
+ Gii han no trong khong kh (930C)
1,8% V
+ Ty trong pha hi
4,1
+ Ch so khuc xa n15
1,55457
2. Tnh chat hoa hoc cua nitrobenzen :

Hp chat nitro thm tham gia hai loai phan ng
chnh la : phan ng kh hoa nhom nitro (NO 2) thanh
nhom amin NH2 va cac phan ng the xay ra nhan
thm (the electrophylvaf the nucleophyl).
a. Phan ng kh : Hp chat nitro thm b kh hoa
tao ra cac san pham trung gian kha phc tap.
- Kh trong moi trng axit : chat kh c dung
la kim loai , v du: Fe hoac Sn, Zn trong moi trng axit
(HCl)
NO2
2H
NO2O
2
-H
NO
NHOH
2H
2H
NH2
+
H2 O
17
O AN TOT NGHIEP
Thiet Ke Phan Xng
Nitrobenzen
Nitrozo
Hydroxylamin
Anilin
- Kh trong moi trng kiem : chat kh Zn +
NaOH hoac NiAlH4. Phan ng tao ra cac san pham
NO2 kha phc
NO tap va kho
NHOHtach.
trung gian
[H]
N=N
nitrrobenzen
nitrrozo
hydroxyamin
O
NH2
oxibenzen
N = N
Az
NH NH
2
Azobenzen
Hydrazobenzen
- Kh trong moi trng trung tnh : chat kh : Zn +

NH4Cl. Phan ng kh dng lai san pham
hydroxylamin.
NO2
NHOH
+
2Zn
NH 4Cl
H2O
benzen
hydroxylamin
Phan ng kh hoa co the tien hanh vi hydro

phan t H2, dung xuc tac Ni hoac Pt, Pd.
b. Phan ng the electrophyl : NO2 la nhom thu ong
hoa nhan benzen trong phan ng SE , va la nhom
nh hng meta :
V du :
NO2
NO2
FeC3
18
O AN TOT NGHIEP
Thiet Ke Phan Xng
Cl2
Cl
HCl
Nitrobenzen
nitrobenzen
m clo
c .Phan ng the nucleophyl:

Nhom -NO2 the hien hai hieu ng am : -C, -I ,
la nhom hut electron manh , lam giam kha nang
phan ng cua nhan trong phan ng the electrophyl.
Ngc lai no lam hoat ong hoa vong thm trong
phan ng the nucleophyl .
V du:Phan ng the nucleophyl cua dan xuat
halogen xay ra thuan li khi trong vong benzen ,ngoai
nguyen t halogen con co nhom -NO2 cac v tr
octo va para.
O2N--
--CL + NaOH
O2N--
--OH + NaCL
Nhom
-NO2
la nhom hut electron manh lam
phan tan ien tch am va lam be cacbanion trong
phan ng the electrophyl.
3. ng dungcua nitrobenzen:
Nitrobenzen la mot san pham trung gian quan
trong . Hau het nitrobenzene c dung e chuyen
hoa thanh anilin ,benzidin, dinitrobenzene,lamf chat xuc
tien lu hoa cao su, dung e san xuat thuoc nhuom
anilin en .Ngoai ra con dung lam dung moi chon loc
e tinh che dau mo va moat so ng dung quan trong
na la dung e san xuat thuoc no va dung trong y
dc.
Chng II.
CAC PHNG PHAP SAN XUAT NITROBENZEN

[ 8 ].
19
O AN TOT NGHIEP
Thiet Ke Phan Xng
1. Niro hoa bang axit HNO3 :

Phan ng xay ra theo phng trnh :
ArH
+ HONO2
ArNO2 + H2O
Nc tao ra trong qua trnh se lam loang nong

o cua HNO3. Hang so van toc phan ng nitro hoa
phu thuoc vao nong o axit cho nen van toc nitro
hoa giam xuong khi nong o axit giam ti mot tr
so xac nh th phan ng thc te khong the xay ra
na .
v du : nitro hoa toluen khi nong o HNO 3 < 50% se
khong xay ra na.
e tang cng van toc nitro hoa th tang nhiet
o len nhng qua trnh oxi hoa lai tang, lam sinh ra
cac san pham phu khong mong muon.
oi vi phng phap nay tot hn het la nen
lam viec nhiet o thap va phai dung axit nitric
that tinh khiet.
Nhieu chat b nitro hoa bi HNO3 nh : phenol,
phennangtren, naptalin, angtraxen...
Nhng thc te trong cong nghe t dung oc nhat
HNO3 thng them chat hut nc vao.
2.Nitro hoa bang axit HNO3 + H2SO4 :
ay la phng phap thong dung nhat hien nay v
co nhng u iem sau :
- S dung c hoan toan HNO3.
- Giam bt c qua trnh oxi hoa cua HNO 3 en
mc toi thieu.
- Co the dung lai c axit a lam viec (rat kinh
te).
- Co the nitro hoa nhiet o cao c (cao hn
so vi phng phap dung HNO3 ).
20
O AN TOT NGHIEP
Thiet Ke Phan Xng
- Axit H2SO4
giup cho qua trnh tao ra NO 2+
nhanh,lam tang van toc phan ng.
- Hieu suat at c tng oi cao en 98% lai
khong can HNO3 tinh khiet. Ngoai H2SO4 ra con co the
dung cac tac nhan khac e hut nc nh : BF 3,
P2O5 ...
V du :
ArH + HNO3 + BF3 ArNO2 + BF3. H2O
3. Nitro hoa bang muoi cua HNO3 :
Phan ng xay ra theo phng trnh :
NaNO3
H2SO4
HNO3
NaHSO4
HNO3 la tac nhan nitro hoa.

+u iem cua phng phap nay :
- Moi trng tuyet oi khong co nc.
- Hau nh khong co qua trnh oxi hoa, khong co
HNO2.
+Nhc iem :
-Khong the s dung can tha la bisulfat natri.
- Neu ta dung NH4NO3 th tot hn v bisulfat amon
dung tot va x ly de dang.
- Neu dung HNO3 e nitro hoa toluen san pham
t oxi hoa la meta nitrobenzenandehyt. Hieu suat cua
no tang theo s tang cua nhiet o.
4. Nitro hoa khi co them HCH3COO hay alhydric axetic :
Hon hp cua HNO3 vi HCH3COO hay vi alhydric
axetic la hon hp tac nhan nitro hoa.
Axit axetic la moi trng tot e nitro hoa mach
nhanh. Dung alhydric axetic con li hn v no con co
tac dung hut nc tot.
Alhydric axetic + HNO3
axetylnitrat.
21
O AN TOT NGHIEP
Thiet Ke Phan Xng
HNO3
(CH 3CO)2 O
N2O5
2CH3COOH
N2O5
(CH3CO)2O
2CH3COONO2
au tien la axetyl hoa sau la qua trnh tao ra hp

chat nitro :
ArH
CH 3COONO2
ArNO2
CH3COOH
Axit axetic cung ket hp vi HNO 3 tao thanh hp
chat phc chat hai cau t (HNO 3.HCH3COO) lam anh
hng en van toc phan ng.
5. Nitro hoa bang phng phap the cac nhom sulfo,
amino, diazo...bang nhom NO2 :
V du :
ArN = N O.NO2
NaNO3
NaNO2
ArN = N O NO +
Diazonitrat
Diazonitrit
Sau o chuyen thanh hp chat nitro :

ArN = NO NO
ArNO2
N2
Phng phap nay thng dung trong cong nghiep

thuoc nhuom e ieu che meta- nitronaptalin hoac
ieu che trong phong th nghiem para dinitro benzen tinh
khiet t para nitro-anilin.
6. Nitro hoa bang oxit nit :
Phng phap nay c nghien cu va a vao
san xuat t nam 1910
en 1915. Nitro hoa bang oxit nit trong ky thuat rat
u viet, v no khong can qua giai oan ieu che HNO 3.
Nh ta a biet san xuat HNO 3 t oxit nit la mot ieu
phc tap ve thiet b va ky thuat, qua trnh phai oxi
hoa NO thanh NO2 sau o dung nc hap thu c
axit loang roi dung H2SO4 ac e tang nong o cua
22
O AN TOT NGHIEP
Thiet Ke Phan Xng
HNO3 . V vay dung ngay oxit nit trong qua trnh oxi hoa
nit la mot van e rat kinh te.
N2O4 nam hai dang ong phan :
N2O4
2NO2
nhiet o thap nam dang ong phan imer

oxit nit khi nhiet o ln hn 140 0C th N2O4 phan ly
hoan toan. Khi nhiet o 27 0C khoang 20% N2O4 nam
di dang monomer.
Mau sac cua N2O4 cung thay oi theo nhiet o,
khi 500C la tinh the khong mau, khi 183 0C la kh
mau en.
Phan ng tac dung gia benzen va N2O4 xay ra :
NO2
+
3HNO3
3N2O4
O2N
+
NO2
benzen
trinitrobenzen
Khi tac dung benzen vi N2O4 ngi ta thng
them tac nhan phu tr vao v du nh AlCl 3 va FeCl3. Khi
co mat nhng clorit ay benzen se tac dung rat
manh liet vi N2O4 tao thanh mot phc chat.
V du : oi vi benzen th thanh phan cuoi cung
la:
2AlCl3.3C6H6.3N2O4
va FeCl3.2C6H6.2NO4
Trong o nc se tach ra khoi hp chat , ong
thi chat hu c C6H6N2O4 tach HNO2
ra va bien
thanh nitrobenzen.
Khi un nong AlCl3 vi N2O4 va hp chat thm
vang mat cua H2O
th phan ng xay ra theo phng trnh :
23
O AN TOT NGHIEP
Thiet Ke Phan Xng
2AlCl3 + 3ArH + 3N 2O4 3ArNO2 + 3NOCl +

Al2Cl3(OH)3
Titop cho rang s tac dung xay ra do s bao hoa
tng bac cua AlCl3, giai oan au tao thanh :
ArNO2.AlCl2(OH)+ AlCl3.NOCl va cuoi cung tao thanh :
AlCl(OH)2.ArNO2.2NOCl.
C che phan ng nitro hoa nay Titop giai thch
bang s tac dung co cc cua AlCl 3 dan en s ion
hoa phan t N2O4 nh s o :
AlCl3
N2O4
AlCl3.NO2.NO2
H
AlCl3.NO2.NO2 + C6H6
NO2
( NO2AlCl )H+
Trong hp chat trung gian nay, hydrozen lien ket
vi nguyen t cacbon cung vi NO 2 , de dang tach ra
di dang ion e tao thanh nitrobenzen roi ket hp
vi phan t th hai AlCl3 thanh phan t.
Ngi ta con dung PCl 5 lam tac nhan phu tr,
phan ng xay ra theo phng trnh :
PCl5 + ArH + N2O4 POCl3 + HCl + NOCl +
ArNO2
Phng phap nay ch dung gan ni san suat
HNO3.
7. Nitro hoa bang oxit nit co mat H2SO4 :
Khi co mat H2SO4 th :
N2O3
2NO +
3H 2SO4
3HSO 4-
+ H3O+
N2O4
+ 3H2SO4
NO + + NO2+ + 3HSO4-
+ H3O+
N2O5
3H 2SO4
2NO 2+
3HSO4-
H3O
24
O AN TOT NGHIEP
Thiet Ke Phan Xng
NO2+ la tac nhan nitro hoa.

Trong qua trnh ch co 50% ioxit nit la tham gia
vao phan ng. Con 50% khac tac dung vi axit H 2SO4
thanh sulfua nitrozyl :
C6H6 + H2SO4 + 2NO2
C6H5NO2
NOOSO3H
H2O
Phan ng vi toluen, meta va para xylen ,
clobenzen, nitrobenzen cung xay ra tng t nh the.
Angtraquinon cung cho san pham nitro khi tac dung N 2O4
trong moi trng oleum cha 5% SO3 cung vi axit
H2SO4 nong o 70 100%.
8. Nitro hoa bang HNO3 vi s tach nc phan ng :
u iem cua phng phap nay la khong dung
H2SO4 v viec thu hoi H2SO4 trong axit a dung ton
nhiet, he thong thiet b ac biet.
S tach nc tao thanh bang cach tao nen mot
hon hp ang ph gia nc va hydrocacbon thm hay
vi mot dung moi tr cho vao ty le vi lng HNO 3.
Nhieu ArH tao ra vi nc mot hon hp ang ph
nh : Toluen nc soi 84,10C (toluen soi 110,80C).
Benzen nc soi 690C
(benzen soi 80,40C).
Duy tr nhiet o cua nitrator bang nhiet o soi

cua hon hp ang ph se tach c nc trong qua
trnh nitro hoa.
+u iem :
- Khong nhan c axit a dung, khong can tai
sinh.
- Tach nc nen tang nong o cua HNO 3.
Hon hp bay len se qua tinh luyen dung dch
ang ph khong ong nhat bac 2 se tach bang lang
phan rieng. ArH se a ve e nitro hoa lai.
25
O AN TOT NGHIEP
Thiet Ke Phan Xng
Muon tang toc o cua qua trnh dung HNO 3

dang hi. Hi HNO3 khuech tan vao trong ArH, khoi
phan ng ong nhat, be mat tiep xuc ln nen
van toc nitro hoa ln.
nhiet o cao HNO3 hoat ong hn.
HNO3
Ar
HO*
NO2*
Ar*
Ar
NO2*
Ar*
Ar
HO*
ArNO2
+
+
+
HO*
HOH
HNO2
Qua trnh co nang suat ln, de lien tuc.

+Nhc iem :
Dung thiet b bang thep khong r. Trong thc
te t dung.
Chng III.
LY THUYET VE QUA TRNH NITRRO HOA.
Hien nay, nitrrobenzen c san xuat theo phng

phap thong dung nhat la nitro hoa benzen bang tac
nhan nitro hoa la hon hp cua axit nitric va axit
sulfuric.
I .QUA TRNH NITRO HOA.
Phan ng nitro hoa vong benzen xay ra theo c
che electrophyl, c bieu dien bang phng trnh sau :
26
O AN TOT NGHIEP
H2O
Thiet Ke Phan Xng
H2SO4
55 60 0C
NO2
+
HNO3
Nhiet phan ng cua qua trnh nitro hoa rat ln :

36,4 - 142,5 kj/mol (24 34 kcal/mol). Phan ng nitro hoa
tao ra nc nen nong o HNO3 giam dan. Hang so
van toc cua phan ng phu thuoc vao nong o axit
ay nong o HNO3 giam dan va thc te giam
en mot tr so xac nh cua nong o phan ng se
dng lai. V du : nitro hoa benzen bang HNO 3 800C
phan ng se khong tiep tuc na khi nong o cua
HNO3 = 50%. Neu nhiet o thap hn phan ng se
ngng nong o cao hn. Khi nitro hoa bang HNO 3
loang qua trnh oxi hoa lai xay ra manh liet hn (HNO 3
co kha nang oxi hoa hydrocacbon khi nhiet o rat
thap du vang mat H2O hay co mat H2O), ieu nay
the hien ro ret bang s tach oxit nit trong phan
ng vi HNO3 loang. Chnh v the nen trong thc te
ngi ta khong nitro hoa oc nhat bang HNO 3.
e tranh nhng anh hng xau ay ngi
thng s dung nhng chat hut nc. Pho bien va
thong dung hn ca la dung H 2SO4. Hon hp HNO3 +
H2SO4 goi la hon hp nitro hoa hay hon hp axit. Hon
hp nitro hoa c che tao t axit H2SO4 96 en 98%
va HNO3 ky thuat nong o 60 en 65%( =1,4) hay 95
98% ( = 1,5), e thuan tien trong cong nghiep
ngi ta thng dung hon hp menlazo, gom HNO 3
am ac, 7,5 9% H2SO4 va khoang 4,5% H2O, cai li
cua hon hp nay la co the van chuyen trong nhng
thiet b bang gang thep ma khong b an mon (khi
nitro hoa tnh toan pha them axit H 2SO4 vao).
Ngi ta con dung ca oleum e che tao hon
hp nitro hoa. Ngoai hon hp HNO 3 + H2SO4 ra con co
the s dung hon hp H2SO4 + NH4NO3, oi khi dung
27
O AN TOT NGHIEP
Thiet Ke Phan Xng
hon hp nitro hoa la HNO 3 vi dung moi CH3COOH hay

nhng dung moi khong tan trong no nh clobenzen,
policlorit benzen, CCl4, BF3. Nhng dung moi nay la tac
nhan hut nc rat tot. Xong v kho tai sinh va hay
gay ra phan ng phu nen cac loai dung moi nay t
c s dung.
Viec a them nhom NO2 vao se lam giam mat
o ien tch trong vong benzen (NO2 la nhom hut
electron) do o cung lam giam hoat tnh cua vong
benzen oi vi phan ng the electrophyl. Chnh v vay
nen cac san pham the di - , tri nitrobanzen hiem khi
xay ra di ieu kien c s dung cho qua trnh the
mono nitro. Cac qua trnh di nitro hoa oi hoi cac
ieu kien khac nghiet hn i kem theo (nong o axit
cao va nhiet o cao) cung nh phai s dung qua trnh
tach san pham mono va thc hien phan ng tng
bc.
Qua trnh nitro hoa co the c thc hien theo
phng thc gian oan hay lien tuc. e co c chi
ph thap th ngi ta s dung phan ng gian oan
trong thiet b phan ng (thiet b nitro hoa) c thiet
ke e thch nghi ni nhieu loai san pham khac nhau.
Cac phan ng nitro hoa eu kem theo s toa
nhiet, oi v mononitro hoa benzen co
H = -117
kj/mol, con naphtalen co H = - 209kj/mol. Qua trnh toa
nhiet nay oi hoi pha lam lanh mot cach co hieu
qua , bang viec s dung qua trnh lam lanh bang
vo boc ngoai hoac lam lanh trong hay ca hai phng
phap .V l do an toan, thiet b thong c gii han
kha nang cha khoang
6000 lt ,ket hp vi may
khoay .Qua trnh
lien tuc dung cho san xuat hp
chat trung gian (nitrobenzene , dinitrobenzen) co o an
toan va hieu qua kinh te cao .
28
O AN TOT NGHIEP
Thiet Ke Phan Xng
Hai lnh vc quan trong trong cong nghe nitro hoa

ang c chu y en va cai tien hien nay tren the
gii la:
+ S dung axitsunfuric tuan hoan.
+ ieu khien cac ong phan va tach
chung.
II. LY THUYET CHUNG.
1. Ban chat tac nhan nitro hoa.
Tac nhan nitro hoa la hon hp cua hai axt HNO 3
va H2SO4. ay ta xet en vai tro ac biet cua
H2SO4.
Theo Maccopnhicop th hon hp nitro hoa tao ra anhydric
HOSO2ONO2 va chnh no la tac nhan nitro hoa. S tao
thanh anhydric xay ra theo phng trnh sau :
H2SO4
HNO3
HOSO2ONO2
H 2O
Gia thiet nay khong ung v thc ra tac nhan

nitro hoa chnh la ion NO2+. Ion nitronyl nay tao ra cung
ni ion hydroxyl va bisulfat theo phng trnh cua Titop :
HNO3
2HSO4 (1)
+ 2H2SO4
NO 2+ + H3O+ +
e xac nhan co thc ion nitroni NO 2+ ngi ta a

nghien cu theo nhieu phng phap khac nhau :
Xaponhicop a nghien cu thay o dan ien
cua dung dch HNO3 + H2SO4 kha ln chng to trong
dung dch co ion. Dung dch ien ly cua HNO 3 trong
oleum th HNO3 chuyen hoan toan thanh NO 2+ ; trong
hon hp axit loang ion NO 2+ tao ra rat t (ien phan
dung dch HNO3 trong oleum axit HNO3 nam trong dung
dch dang cation).
Nghien cu bang quang pho cua dung dch HNO 3
trong H2SO4 thay xuat hien mot ng co tan so
bang 1400 cm-1, ng nay khong co trong HNO3
loang, nhng lai xuat hien trong HNO3 ac, kha manh
29
O AN TOT NGHIEP
Thiet Ke Phan Xng
va ro ret nhat trong hon hp HNO 3 + H2SO4 . Cng

o ng nay giam i khi ham lng nc trong hon
hp tang len. Th nghiem a en ket luan : co s
phan ly ra O = N+ = O mi lam xuat hien ng
thang cua quang pho.
Trong oleum ion nitroni
phng trnh :
HNO3
NO2 tao ra t HNO3 theo

NO2+
H2S2O7
+ HSO-4 +
H2SO4
Theo s bien oi cng o cua ng co tan
so 1400 cm-1 trong quang pho th hang so van toc cua
phan ng (1) la :
[NO2+] [H3O+] [HSO4-]2
K=
[HNO3] [H2SO4]2
Hang so van toc (K) bien oi t 30 42. Theo

so lieu ong hoc th K = 30 36. Bi vay khi dung d
H2SO4 vi HNO3 t nc thc te HNO3 phan ly hoan
toan thanh (NO2+) cation nitronyl.
Nghien cu bang quang pho phan ly lien hp
thay ham lng NO2+ trong hon hp H2SO4 + HNO3 bien
oi nh sau :
HNO3trong
1
1
2
8
9
1
hon hp
5
10 15 20 40 60 80 90 10
(%)
0
HNO3chuyen
1
1
8
9
2
1
9
5
1
thanh NO2+ 10 10 80 62, 28, 16, 9,8 5,9 10
(%)
0
0
5
8
7
0
Khi ch co HNO3 th ion nitroni se tao ra theo phng
trnh :
2HNO3
NO2+ + H2O +
NO3- .
30
O AN TOT NGHIEP
Thiet Ke Phan Xng
Khi them nc vao HNO3 100%, nghien cu bang

quang pho thay ion nitroni se t i va mat han.
nong o HNO3 94 95% nhng hon hp cua HNO 3 vi
H2SO4 khi pha them nc vao th ion NO2+ van tao ra.
V du : Hon hp la H 2SO4 +
ham lng cua HNO3 la 70%, ion
ham lng H2O cha trong o la
HNO3 la 30% th ion NO2+ mat i
cha trong o la 13,5%.
HNO3 + H2O trong o

nitroni ch mat i khi
11%. Neu ham lng
khi ham lng nc
Trong o axit nitric khan phan ln HNO 3 nam

dang phan t trung hoa HONO2. Mot vai tnh chat cua
HNO3 nh s bien oi sc cang be mat cung vi
nhiet o, trong lng phan t, quang pho t ngoai
chng to co s lien hp cac phan t cua axit nitric
do lien ket hydro theo cau tao sau :
O. . . .HO
O N
N O
OH . . . . . . O
Nghien cu ac tnh bien oi nhiet o nong

chay cua axit nitric (nong o HNO3 100%) khi them
nc va N2O5 vao thay rang trong axit HNO 3 nong o
100% cha khoang 97% (theo trong lng) HNO 3 khong
b phan ly va khoang 1% NO2+ , 1,5% NO3- va 0,5% H2O
c tao thanh theo phan ng.
2HNO3
NO2+ + NO3- +
H2O
Khi them nc vao axit nitric chu yeu tao thanh

cac phc chat khong b ion hoa gom : [(H 2O)(HNO3)2]
Nong o axit HNO3 la 95 100% va [(H2O)(HNO3)]
nong o axit la 80 95% phan ly thanh ion theo phng
trnh :
HNO3 + H2O
H3O+
NO3-
Axit nitric nong o 75% va cao hn th s phan ly

thanh ion xay ra mc o khong ang ke.
31
O AN TOT NGHIEP
Thiet Ke Phan Xng
Neu tiep tuc giam nong o HNO 3 th mc o

phan ly thanh phan t tch ien c tang len.
Nang cao nhiet o len th mc o phan ly cua
HNO3 cung b giam i.
Nhng gia thiet va so lieu thu c trong cac
cong trnh nghien cu a en ket luan la : tac
nhan nitro hoa la ion nitroni va H 2SO4 ong vai tro
quan trong lam cho s phan ly ra NO2+ de dang va
lng HNO3 tieu ton t. V vay thc te hay s dung
hon hp nitro hoa la HNO3 + H2SO4.
2. C che phan ng nitro hoa bang hon hp H 2SO4 +
HNO3.
Gonleman Vilanda a nghien cu c che phan
ng nitro hoa cua benzen vi axit nitric cho rang au
tien axit nitric ket hp vi nhan thm theo noi oi roi
tiep tuc tach nc thanh nitrobenzen
+
benzen
nitrobenzen
OH
NO2
H
- OH
H
NO
- 2
-
- H2O
NO2
S xac nhan tren c tm ra trong khi tach san

pham tng t cua s ket hp axit nitric vi
hydrocacbon khong no, naphtalin va angtraxen. Thieu sot
cua s o tren la khong c ro rang khi tiep tuc
chuyen hoa san pham ket hp thanh dan xuat cua
benzen.
Titop nghien cu s tac dung cua axit nitric vi
naphtalin thay rang san pham nhan c khong phai
la n chat ma la mot hon hp cha nitro naphtalin,
naphtalin va axit nitric. Nghien cu ky hn na phan
ng tac dung cua hydrocacbon loai etylen vi axit
nitric , chng to rang axit nitric ket hp theo noi oi
nh nhng axit vo c khac ong thi tao thanh nitrat
32
O AN TOT NGHIEP
Thiet Ke Phan Xng
cua ru khong no theo s o :

H
ONO2
C = C
+ HONO2
Tronop cung nh Nanutkin va Zabrodin coi s ket

hp cua axit nitric vi benzen theo s o cua Gonleman
Vilanda khong ro rang.
Cac nha nghien cu nay gia nh rang hp
chat trung gian tao thanh do ket qua cua s ket hp
axit nitric vi hydrocacbon theo s o :
O
C6H6 + N
O
O
C6H5 . N
- H2 O
C6H5NO2
OH
O H
OH
Tronop da tren nhng cong trnh da nghien cu

theo ong hoc phan ng gia benzen va axit nitric
trong dung dch nitrobenzen, cung nh cong trnh nghien
cu nitro hoa benzen bang etylnitrat, thay rang phan
t axit nitric tham gia chu yeu e tao thanh san
pham trong o mot phan t hoat hoa phan t
benzen con phan t th hai c ket hp nh s o :
O
N
O H
OH
(HNO3)
Qua mot so nghien cu khac Tronop con thay
rang gia nitrobenzen va axit nitric ton tai mot phc
chat co thanh phan la : C6H5NO2 + HNO3 va C6H5NO2 +
2HNO3.
33
O AN TOT NGHIEP
Thiet Ke Phan Xng
oi chieu nhng so lieu tren ve thanh phan

hon hp nitro hoa va ve ong hoc qua trnh nitro hoa
th nhng c che phan ng ay cha c ro rang
lam.
Ve sau nhieu cong trnh nghien cu a tm c
c che phan ng nitro hoa thch hp nhat.
Trong hon hp axit HNO3 va H2SO4 khan nc, axit
nitric hoan toan hoac phan ln nam dang cation
NO2+. Titop coi cation NO2+ la tac nhan nitro hoa ro ret
khi nitro hoa nhng chat tng oi kho b nitro hoa
bang hon hp axit H2SO4 va HNO3. Theo Titop kha nang
phan ng cao cua cation NO2+ la do s bao hoa ien
t va cha bao hoa cua nguyen t nit.
Cation nitroni c tao ra theo phan ng :
HNO3
H2SO4
HOSO2ONO2
NO2+
HOSO2ONO2
H2O
+ H2SO4-
C che phan ng nitro hoa gom hai giai oan. Giai

oan cham hn va quyet nh toc o cua toan bo
qua trnh la giai oan trong o moi lien ket gia
nguyen t hydro va cacbon b pha v.
NO2
O2
(I)
H
N
H
+ NO2+
cham
NO2
H
H+
nhanh
+
+
NO2
(II)
HSO4-
hay
H+
H2SO4
Theo c che nay giai oan (I) ong thi cung la

giai oan cham nhat va quyet nh toc o cua toan
bo qua trnh la yeu cau ket hp ion NO 2+ vi nhan
thm tao thanh san pham co cau tao :
NO2
NO2
H
34
O AN TOT NGHIEP
Thiet Ke Phan Xng
hay
Giai oan hai la giai oan tach proton san pham

ket hp chuyen hoa thanh hp chat nitro xay ra vi
toc o ln hn khong anh hng ti toc o toan
bo qua trnh.
3. ong hoc cua phan ng nitro hoa bang hon hp
HNO3 + H2SO4:
Mactixen a nghien cu anh hng cua nong
o H2SO4 trong hon hp nitro hoa len van toc phan
ng. Ong a nghien cu ong hoc phan ng cua
hp chat thm bang ng lng phan t cua HNO 3
trong axit H2SO4 d vi nhng nong o khac nhau, i
en ket luan rang : Phan ng nitro hoa la phan
ng bac hai, hang so van toc cua phan ng thc
te khong bien oi qua tat ca cac giai oan phan
ng vi mot nong o H2SO4 khong oi. Neu thay oi
nong o H2SO4 th hang so van toc phan ng cung
bien oi theo, hang so van toc con phu thuoc vao
nong o chat c nitro hoa.
Qua thc nghiem thay rang , hang so van toc
phan ng at cc ai ng vi ty so 0,63 mol H 2O/
1mol H2SO4 (axit H2SO4 nong o 89,4%), hang so van
toc phan ng se giam i vi nong o cua HNO 3 ln
hn hoac nho hn 89,4%.
Khi chuyen t H2SO4.0,3H2O thanh H2SO4 nong o
100% th hang so van toc phan ng nitro hoa phan
ln giam i 3 lan, oi vi axit benzoic giam i khoang
18,5 lan, oi vi benzosulfo axit giam i 11,5 lan.
Toc o nitro hoa cac dan xuat cua benzen phu
thuoc nhieu vao ac tnh cac nhom the co san
trong nhan, sap xep theo day sau :
NO2 > SO3H > COOH > Cl < CH3 < OCH3 < OC2H5 < OH
35
O AN TOT NGHIEP
Thiet Ke Phan Xng
cham dan i
tang dan
len
Nhng nhom ng pha ben phai clo lam tang
dan van toc phan ng va cang ln khi cang i ve
pha ben phai. Nhng nhom ng pha ben trai clo
lam cham dan phan ng mc o ln hay nho la
tuy thuoc vao mc o cach xa clo.
Anh hng lam cham cua nhom nitro rat ln.
Neu a nhom nitro vao hp chat thm , se lam giam
hang so van toc cua qua trnh nitro hoa ve sau nay
t 105 107 lan.
Qua thc nghiem a xac nhan rang toc o nitro
hoa nitrobenzen cc ai 25 0C khi nong o H2SO4 90% ,
khi nitro hoa bang H2SO4 nong o 95% th toc o
phan ng giam i hn hai lan, con nitro hoa bang
H2SO4 nong o 80% th toc o phan ng giam i 3000
lan. V tr van toc cc ai phu thuoc vao nhiet o, v
du : nitro hoa nitrobenzen 5 0C th van toc cc ai khi
nong o axit H2SO4 la 89% , nhng nitro hoa 40 0C th
van toc cc ai khi nong o H2SO4 la 91%.
Qua so lieu tren chng to rang khong phai
nong o H2SO4 va H2O quyet nh van toc phan ng
nitro hoa ma chnh la do ham so axit (H 0 ) : ac trng
khuynh hng cua moi trng oi vi s truyen
proton cho kiem trung tnh.
fB
a
.
H+
H0 = - lg
fBH+
Trong o :
a : hoat o cua proton.
H+
fB va fBH+ : he so hoat o kiem trung tnh B va
axit cung vi BH+ .
36
O AN TOT NGHIEP
Thiet Ke Phan Xng
T so f B / fBH+ khong oi oi vi tat ca cac

kiem trung tnh, v vay tr so H0 khong phu thuoc vao
ban chat cua kiem.
Axit H2SO4 ong vai tro mot chat xuc tac nhng
lai va co tnh chat dng va am. Theo Titop th axit
H2SO4 c coi la mot phu gia hoat ong ong vai tro
kep : mot mat lam cho HNO3 hoat ong, mat khac
co tac dung xau do phan ng vi hp chat thm tao
ra phc chat, phc chat nay kho phan ng vi
HNO3 e cho san pham nitro hoa. Titop xem mat xau
nay la nguyen nhan ha thap hang so van toc cua
qua trnh nitro hoa khi tang nong o cua H 2SO4 qua
mot tr so xac nh.
4. Qua trnh phu khi nitro hoa :
Ngoai nhng san pham chnh cua phan ng nitro
hoa la hp chat nitro ra, con thay tao thanh mot so
san pham phu nhng ieu kien nitro hoa khac
nhau. Nhng san pham ay c tao ra do ket qua
tham gia ong thi cua nhom oxy va nhom nitro. Titop
nhan thay khi nitro hoa benzen tao thanh dinitrophenol
va axit picric.
C che phan ng tao thanh cac san pham phu
cha c ro rang. Ngi ta gia nh rang trc tien
nh nhom oxy vao hp chat (tuan theo quy luat the
thong thng) roi tiep tuc nitro hoa hp chat oxy.
Nhom oxy c tao ra khong phai la do nit cua tac
nhan nitro hoa ma la do oxy mang ien tch dng tac
dung vi hp chat thm. T nitro benzen trc tin to thnh
meta- nitrophenol sau bin thnh 2, 3, 4, 6 tetra- nitrophenol.
Trong hp cht nitro ny nhm nitro v tr 3 rt linh ng v khi th
n bng nhm oxy th to thnh axit stipninoic. Vic to thnh axit
stipninoic cng khng lin quan n s c mt ca HNO 2. Axit
stipninoic cng c to ra t sulfo tng t nh th (tch nhm ArSO2).
Theo Titop s to thnh sn phm ph ca hp cht nitro xy ra
qua giai on to thnh hp cht nitrozo, nhn c t hp cht thm do
37
O AN TOT NGHIEP
Thiet Ke Phan Xng
tc dng ca cht nitrozo, nhn c t hp cht thm do tc dng ca

cation NO+ (t O=N-SO3H) hay dng nitrat nitrozyl ca dioxyt nit
O
O=NO N
O
V sau trong iu kin nitro ho hp cht nitrozo chuyn thnh
hp cht diazo ri thnh hp cht oxy, cng c th b chuyn nhm
c bit to thnh para- nitrophenol. Sau phenol, cng nh
para- nitrophenol b nitro ho n hp cht polinitro.
C ch phn ng ny gii thch r s to thnh dn xut ca
phenol; meta crezol v meta clorphenol t benzen, toluen v
clorbenzen.
5. Nhng yu t nh hng n qu trnh nitro ho:
a. nh hng ca lng axit HNO3.
Khi nitro ho bng hn hp axit nitric v sulfuric nu tng lng
benzen (nhiu hn lng HNO3) th phn ng nitro ho s chm li, hiu
sut phn ng gim i v cn d mt lng ln benzen, nhng nu tng lng HNO3 trong hn hp th li c tc dng ngc li.
Thc nghim nghin cu v phn ng nitro ho thy rng nu lc
ny ly mt lng tng ng 100 phn trng lng HNO3 v 100 phn
trng lng benzen th hiu sut phn ng t c 80% so vi benzen.
Nu ly 150 phn benzen cc thng s khc gi nguyn th hiu sut
phn ng ch t c 20%. Cn khi ly 50 phn benzen th hiu
sut li tng n 90%. Do vy khi tng lng HNO3 th c li cho phn
ng , v to ra nhiu ion nitroni , lm tng cc hiu sut, ngc li khi
gim lng HNO3 hiu sut phn ng s gim v lng benzen khng
phn ng s tng ln.
b. nh hng ca nng axit H2SO4.
Phn ng nitro ho l phn ng sinh ra nc, nu khng c cht ht
nc th nng HNO3 s gim i v do vy n mt lc no phn
ng dng li vi mt nng ca HNO3 xc nh. Mt khc khi HNO3
38
O AN TOT NGHIEP
Thiet Ke Phan Xng
long, nhit cao , qu trnh oxy ho li mnh lit hn nitro ho. Axit
H2SO4 l cht ht nc mnh , nn n c dng lm tc nhn ht nc
trong qu trnh nitro ho. Nc sinh ra trong qu trnh tin hnh nitro ho
v nc c sn trong HNO3 s lin kt vi axit H2SO4 di dng: H2SO4. x
H2O. V vy nng H2SO4 nh hng nhiu n qu trnh nitro ho.
Axit H2SO4 mt nng thch hp no y s cho vn tc nitro ho
cc i, chnh lc ny n l cht hot ng ho nhn thm, tng
linh ng ca ion NO2+,v lm cho nng lng hot ho ca phn ng
by gi l nh nht v phn ng cho vn tc cc i.
Nhng mi nhit khc nhau , vn tc phn ng li cc i vi
nng H2SO4 khc nhau. V d: nitro ho benzen vi vn tc cc i
khi tin hnh 250C v nng H2SO4 l 89,9%. Vn tc s gim i 2
ln khi nng H2SO4 l 95% v 3000 ln khi nng H2SO4 l
80%.
Di y l th thc nghim ca Mactixen v s ph thuc ca
hng s vn tc phn ng (K) vo nng H2SO4 v nhit .
K
k
Hm lng H2O trn 1 K 250C
3,22
mol H2SO4
0,03
1,50
0,63
3,22
01,03
0,18
S mol H2O/s mol H2SO4
Nhn biu trn ta thy: khong cc i ca hng s vn tc,

axit H2SO4 ng vai tr xc tc dng cho qu trnh nitro ho ngha l
tc dng ht nc v tng hot tnh ca HNO3 ln cao nht.
c nh hng ca nhit nitro ho.
Qua thc nghim thy rng khi tng nhit ln 10 0C th vn tc
phn ng nitro ho s tng ln t 2- 3 ln. Tht vy, nhit 86 0C
39
O AN TOT NGHIEP
Thiet Ke Phan Xng
(nhit si ca HNO3) th HNO3 bt u b phn hu theo phn

ng:
2 HNO3 NO2 + NO + O2 + H2O
Nh th s tn nhiu axit, mt tc nhn HNO 3,v cc kh NO, NO2
bay ra gy c cho sn xut v c khi gy n. Cn O 2 gy ra phn
ng oxy ho vi sn phm hay cht c nitro ho cho ta nhiu sn
phm ph v lm bn sn phm nitro. Mt khc nhit cao cn
cho nhiu polinitro l sn phm ta khng mong mun.
Qu trnh nitro ho cng khng nn tin hnh nhit thp qu
v nhit thp sn phm c th kt tinh li, khi phn ng ng
qunh v ng trn b mt truyn nhit mt lp cao cn tr cho qu
trnh trao i nhit, ko di thi gian nitro ho khi phn ng khng
ng u, sn phm khng ng nht.
Thc t qu trnh nitro ho tt nht trong khong nhit t 40
n 600C.
Nitro ho hydrocacbon th kh t 30 n 70 0C. m bo
nhit phn ng cn phi tin hnh lm lnh thit b vi b mt
truyn nhit thch hp. C th dng cc tc nhn lm lnh khc nhau
nh mui, nc ...
d. nh hng ca nhm th ln qu trnh nitro ho ca hp cht
th ri:
nh hng nhm th ln qu trnh nitro ho cng l iu quan
trng, di y ta xt mt s nhm c bn:
- Nhm nitro (-NO2) c tc dng km hm qu trnh nh hng ca
nhm NO2 rt ln, nitro ho tip v sau s gim i 10 5107 ln v vn
tc phn ng nitro ho.
- Nhm cacboxyl (-COOH) c tc dng km hm qu trnh.
So snh nitro ho to ra nitrobenzen v nitro ho axit benzoic
qua thc nghim thy: vn tc phn ng a nhm NO2 vo v tr
octo i vi nhm cacboxyl gim i 0,3.10 5 ln so vi nitro ho benzen
to thnh nitro benzen, vn tc phn ng a nhm NO2 vo v tr
para hoc meta gim i 1,5.105 ln.
40
O AN TOT NGHIEP
Thiet Ke Phan Xng
- Nhm sulfo (-SO3H) c tc dng km hm ln hn nhm cacboxyl

gp 4 ln, nhng kh hn nhm nitro (NO2) n 17 ln.
- Nhm halogen (-Br, -Cl ). Khi nitro ho clobenzen th a nhm
nitro vo v tr octo s d dng hn vo v tr para v meta.
- Nhm metyl lm tng nhanh vn tc nitro ho.
- Nhm metoxyl (-OCH3) cng tng nhanh vn tc phn ng nitro
ho hn nhm metyl.
- Nhm etoxyl (-OC2H5) lm tng nhanh vn tc nitro ho hn
nhm metoxyl.
- Nhm hydroxyl (-OH) lm tng nhanh vn tc nitro ho hn c.
Qua thc nghim ngi ta sp xp thnh bng sau:
NO2 > SO3H > COOH > Cl > CH3 < OCH3 < OC2H5 < OH
Chm dn
Mnh dn
e. nh hng ca s khuy trn v lm lnh n qu trnh nitro

ho:
Phn ng nitro ho thng tin hnh hai pha, nu khng khuy
trn u th vn tc phn ng rt nh, v b mt tip xc ca hai
pha nh hn ch nhiu kh nng phn ng ca hn hp axit. Phn ng
hu nh ch xy ra trong lp axit cn lp hu c xy ra khng ng
k. Chnh v vy nu khng khuy trn tht u s gy ra hin tng
phn tng v phn ng nitro ho ch tin hnh b mt phn lp,
b mt cng ln phn ng tin hnh cng tt. Vn tc phn ng ph
thuc vo vn tc khuch tn cu t phn ng t trong th tch ti b
mt phn ng v khuch tn sn phm ra khi b mt phn ng.
tng cng khuch tn ta phI tng cng khuy trn. Mt khc
khuy trn u cn lm cho truyn nhit s nhanh hn, trnh c qu
nhit cc b, khuy trn phi i i vi lm lnh, mc lm lnh cn
quyt nh hiu sut phn ng v nng sut thit b. Tu theo
nhit phn ng cn duy tr (i vi cht c nitro ho khc nhau)
m chn tc nhn lm lnh v my lm lnh khc nhau cho thch hp.
III. K Thut Tin Hnh Phn ng Nitro Ho:
1. Thit b nitro ho:
41
O AN TOT NGHIEP
Thiet Ke Phan Xng
Nitro ho thng tin hnh trong thit b bng gang hoc thp
chu axit hay bng thp khng r, c lp thm my khuy, c o bc
ngoi v ng xon lm lnh bn trong tng cng b mt trao i
nhit.khi nitro ho bng axt nitric long th tin hnh trong thit b
bng snh hay trong thit b trng men hoc lm bng thp khng
g v bng thp pha kim loi qu.
V d: Thit b nitro ho lm vic gin on:
42
O AN TOT NGHIEP
Thiet Ke Phan Xng
N c
N c
KH?
6
GHI CH
1. thn
2. o ngoi
3 .ng cho nguy n liu vo
4.ng xon
5. m y khuy
6 . ng cho sn phm ra
Th tch ca thit b nitro ho trong gii hn t 50 lt n 3.5m 3

tu theo nng suet m ta chn cho thch hp .
43
O AN TOT NGHIEP
Thiet Ke Phan Xng
Trong phm vi sn xut ln hn ( 2 n 3 tn sn nitro phm

trong mt ngy m hoc ln hn ). Khi sn xut nitro nng suet ln
th thng ding loi thit b lm vic lin tc c li hn.
nguy n liu benzen
hn h p nitro ho i vo
N c
hn h p axit quay tr l i
n c ra
KH?n?n
sn phm nitro ra
hi n c qu
nhit
hi ra
GHI CH
1. ng xon rut g
2. b khu?ch t n i l u
4. c nh khuy
5. m y khuy
NgoI ra ngi ta cn dng mt s loi thit b nh: Nitrator Smitta(hnh1) .thit b Ntrrator Bia-xi (hnh 2):
44
O AN TOT NGHIEP
Thiet Ke Phan Xng
Hnh1:
Thit b Nitrator-Smita
benzen
Hnh2:
Thit b Bia-xi
1
chuyn
dng
hn hp axit
benzen
H2O
chuyn
dng
2
H2O
hn hp axit
3
1.My khoy
2.b phn lm lnh
3.B phn cho sn phm ra
1.My khoy
2.Nguyn t lm lnh
3.B phn cho sn phm ra
+ u im ca hai loi thit b trn l khoy v lm lnh rt tt ,

m bo c hiu suet ca phn ng , trnh tch nhit cc b v tho
c hon ton sn phm ra ngoi.
Vi d: Hiu sut cu nitrobenzen thu c khi tin hnh trong
thit b ca Bia-xi t c 98.4% so vi l thuyt.
2. Chun b hn hp nitro ho:
Hn hp nitro ho c iu ch bng phng php pha trn nhng
lng HNO3 v H2SO4 theo nh tnh kh nng nitro ho ca hn hp axit
ban u c quyt nh bi t l nng HNO 3, H2SO4 v H2O. Ngi ta nh gi kh nng ny bng i lng hot ng nitro ho k hiu l
NF.
NF =
C H 2 SO 4 .
140
140 C HNO 3
Trong :
45
O AN TOT NGHIEP
Thiet Ke Phan Xng
C
: Nng ca axit H 2SO4 trong hn hp nitro ho (% khi lH
2SO4
ng).
ng).
CHNO3: Nng ca axit H 2SO4 trong hn hp nitro ho (% khi l-
i vi mt loi cht thm u c mt gi tr NF ti hn. Gi tr ny

cng cao nu kh nng phn ng ca hp cht cng thp v ngc
li.
Khi tin hnh iu ch hn hp nitro ho c s dng axit lm vic
th lng axit HNO3 vn ly xp x bng lng tnh ton theo l
thuyt. Cn lng axit H2SO4 tnh theo nng axit lm vic. Nng
axit lm vic c c trng bi kh nng dehydrat k hiu DC.
DC = H2SO4/HNO3
Kh nng hydrat l t l gia lng H2SO4 cn trong axit lm vic
v lng nc (bao gm c nc nitro trong axit v nc to thnh trong phn
ng). Hiu sut qu trnh ph thuc vo DC. i vi mi cht c gi tr
DC c trng cho kh nng nitro ho ca n. Hp cht cng kh nitro
ho th DC cng cao v ngc li.
Trong khi iu ch hn hp nitro ho tu theo phm sn xut ln
hay nh m s dng nhng s iu ch khc nhau. C hai s
iu ch hn hp nitro ho thng dng nht hin nay l s trong
phm vi sn xut vi nng sut ln v s trong phm vi sn xut vi
nng sut khng ln.
i vi s iu ch hn hp nitro ho trong phm vi sn xut vi
nng sut khng ln, s tin hnh nh sau:
46
O AN TOT NGHIEP
Thiet Ke Phan Xng
hn h p nitro
ho
N c hoc axit
lam vic
N c hoc hn h p
melanz
H2so4
4
5
3
GHI CH
1. th ng cha axit
2. th ng l ng
3. Th ng cha hn h p Nitro ho
4. Bm
5. Bm tun hon
5. thi?t b?lm l nh
axit sulfuric c, axit nitric hay hn hp melanzo v nc hoc axit

lm vic t cc thng cha (1) c a ln thng lng (2) nh khng
kh nn, sau t cc thng lng ny axit sulfuric c, axit nitric hay
hn hp melanzo v nc hoc axit lm vic i vo thit b (4) theo
ng cc t l tnh ton. Trong thit b khuy trn (4) c my
khuy v v lm lnh. My khuy lm vic lin tc m bo
ng u v phn b nhit tt trong ton b hn hp. Qu trnh trn
to nhit mnh nn phi dng nc lnh lm lnh. Sau hn 1 gi, qu
trnh trn xong, hn hp chy vo thng cha (3) v c a vo qu
trnh nitro ho nh khng kh nn.
i vi s iu ch hn hp nitro ho trong phm vi sn xut vi
nng sut ln, s tin hnh nh sau:
47
O AN TOT NGHIEP
2
Thiet Ke Phan Xng
HNO3 hoc
hn h p melanz
khng kh?n?n
H2o
H2o
N c hoc
axit lm vic
khng kh?n?n
H2sO4
khng kh?n?n
hn h p nitro ho
1
3
GHI CH
1. th ng cha axit
3.Thi?t b?trn
2. Th ng l ng
3. Th ng cha hn h p nitro ho
axit sulfuric c, axit nitric hay hn hp melanzo v nc hoc axit

lm vic t cc thng cha (1) c a ln thng lng (2) nh bm li
tm chu axit melanzo v nc hoc axit lm vic chy vo thng
cha hn hp nitro ho (3) theo ng t l tnh ton. T thng cha
(3) hn hp dung dch axit ny c bm tun hon (5) bm lin tc
nhiu ln qua thit b lm lnh (6) ri tr v thng cha (3). Qu trnh
bm nhiu ln ny lm cho hn hp dung dch trn ln vi nhau to
nn hn hp nitro ho. Sau hn hp nitro ho c a vo thit b
nitro ho nh bm (5).
3. Sn xut nhng hp cht nitro.
Qu trnh sn xut nhng hp cht nitro c tin hnh theo s
chung sau y: Nguyn liu ban u tham gia phn ng nitro ho vi
hn hp axit. Sau a vo thng lng. Axit dng nm lp di (ho
tan: 0,5 3% sn phm nitro) cn lp trn l sn phm nitro lng cha
mt t axit H2SO4 v axit HNO3 dng ho tan hoc nh tng.
trch ly mt phn ln sn phm nitro ho tan ra khi axit dng ngi
ta thng dng nguyn liu ban u trch ly.
48
O AN TOT NGHIEP
Thiet Ke Phan Xng
Sau khi trch ly axt dng i vo thng cha, t mt phn

axit quay tr li ch to hn hp axit, phn cn li c chuyn n qu
trnh kh v c c. Kt qu l hon li c phn axit nitric cha phn
ng v hu ht axit sulfuric.Sn phm nitro axit em ra bng nc v
dung dch Na2CO3 sau chng ct bng hi nc ta thu c sn phm
nitro nguyn cht.
S sn xut nhng hp cht nitro.
S s n x u t n h n g h p c h t n it r o
H2so 4
nguy n
HNo 3
l i u u
Tr n a x i t
Ni t r o h o
l n g
Ax it l m v i c
S n ph m n i t r o
Tr ?c h l y
Ng u y n l iu b a n
u v s n ph m
t r ?c h l y
N c
Du n g d ?c h Na2CO
a x i t l m
v i u sa u k h i
t r ?c h l y
kh v
c c
r a
N c r a
s n ph m
IV.Sn xut nitrobenzen.

Qu trnh sn xut nitrobenzen qua mt s giai on chnh sau:
- Chun b hn hp axit.
49
O AN TOT NGHIEP
Thiet Ke Phan Xng
- Nitro ho benzen.
- Tch sn phm nitrobenzen v axit d.
- Ra sn phm v trung ho sn phm.
- Lng axit dng.
- Trch ly nitrobenzen trong axit dng bng benzen.
Trong cng nghip sn xut: Nitrobenzen c th tin hnh bng
phng php gin on hay lin tc.
1. S sn xut nitrobenzen bng phng php lin tc hai bc:
Cho benzen ln nitrobenzen v hn hp axit cha 25% HNO 3
(theo trng lng) vo thit b (1). Nitro ho tin hnh t 3 n 10 pht
nhit 46-97,50C. Sau chy sang thit b phn ly (2), phn
chia thnh 2 lp. Lp trn l nitrobenzen chy sang thit b (3) ra
bng nc , ri chuyn sang thit b phn ly (4). Lp di l nitrobenzen
tip tc em i iu ch anilin (hoc cho vo kho) cn lp nc trn
bm quay li thit b ra (3).
Lp axit lng di thit b phn ly (2) chy vo thit b nitro ho
(nitrator) tc dng lin tc bc hai (5), ng thi cho benzen nguyn
cht vo trn ln vi lp axit . Nh ho ca benzen v axit dng t
thit b (5) chy xung thit b phn ly (6), phn ly thnh 2 lp, lp
trn l hn hp benzen v nitrobenzen, c bm ln thit b nitro ho
tc dng lin tc (1), cn lp di l axit dng em i c c v ti
sinh hn hp axit.
Trong thit b (5) khng ch s dng hon ton axit nitric d trn
m cn c nhim v trch ly nitrobenzen ra khi axit dng. Hiu
sut nitrobenzen t c l 99% so vi l thuyt.
50
O AN TOT NGHIEP
Thiet Ke Phan Xng
S s n x u t Ni t r o b en z en LIN T C HAI BC
h N H P
a x IT
3
5
7
7
n c em
t in h c h ?
n it r o
b ez en
a x i t
d ng
GHI CH
1; 5 Thi?t B?Nitro ho t c dng li n tc
3. thi?t b?nitro benzen
2;4;6 Thi?t b?phn ly
7.b m
2. S nitro ho benzen theo Kater.

Phn ng nitro ho benzen tin hnh trong 10 pht. Nhit phn
ng c dng un nng khi phn ng. Kt thc qu trnh nitro
ho, nitrobenzen c ly ra, cn axit dng nng 72% cho chy
xung thng cha (c un nng) (8), ri ht chn khng a ln thit
b bc hi (9). thit b bc hi khi p sut 35mmHg nc cng vi
nitrobenzen c tch ra khi axit sunlfuric, ngng t li trong thit b ngng (10).
S bc hi xy ra cn bn l do lm lnh axit dng ngha l nh
nhit phn ng nitro ho. Trong thit b bc hi axit sulfuric ngng li
c t 72-75% H2SO4 chy xung thng cao v (7) v chy vo nitrator
(1), (2), (3), (4).
Trong mi mt ni nitro ho xy ra 4 qu trnh (trn axit, nitro ho,
lng v phn ring). Chuyn pha theo thi gian to thnh mt dng
lin tc.
51
O AN TOT NGHIEP
Thiet Ke Phan Xng

S s n x u t Ni t r o b en z en t h eo k a t n er
CHn Khng
10
HNO3(83%)
BenZen
H2SO4
6
7
GHI CH
1;2;3;4 THi?t b?Nitro ho
9.Thi?t b?bc hi
5;6;7 Th ng cao v?
10.Thi?t b?ng ng p k?
8. Th ng cha axit d ng
3. S sn xut nitrobenzen ca Nga:

Benzen, hn hp axit v axit dng cho vo vo ni nitrator (1).
Ngi ta iu chnh t ng lng benzen v hn hp axit cho vo theo
t l cho, cn lng axit dng iu chnh theo nhit trong ni
nitrotor. (Trong ni nitrotor (1) c ng xon bn trong lm lnh bng nc, c b phn khuch tn i lu, c my khuy 350 vng/pht). Sau
khi phn ng t ni nitrotor (1) c bm sang thit b lm lnh
kiu xon c (6) v (7). thit b lm lnh (6) tin hnh nitro ho nt
ngha l chuyn ho hon ton axit nitric cha trong axit dng, cn
trong thit b (7) khi phn ng c lm lnh n 300C ri a ln thit
b phn ly (8), chia thnh 2 lp nitrobenzen v axit dng.
52
O AN TOT NGHIEP
Thiet Ke Phan Xng
Nitrobenzen tip tc em i ra v trung ho, cn axit dng c

quay li thng lng (4) tip tc nitro ho.
Trong nitrator tiu tn gn 90% axit nitric (cha trong hn hp
axit) cn trong thit b lm lnh (6) tiu tn 9-9,5% axit nitric. Tch
nitrobenzen t axit dng xy ra nhanh v c hiu qu do t trng
khc nhau nhiu (1,2 v 1,6g/cm3). Tc ri nh nht ca axit
dng khi phn phi vo nh tng l 2mm/giy, ng vi thi gian phn
lp cc tiu l 5 pht. Nhng thng lng loi nm ngang c hiu qu ln
nht.
S s n x u t Ni t r o ben zen C A NGA
h n h p a x it
3
n it r o b en zen
12
13
14
i t r i c h l y
h 2o
h 2o
b en z en v
n i t r o b en z en
15
11
h 2o
h 2o
GHI C H
1. thi?t b?nitro ho
6;7 .Thi?t b?lm l nh xo n c
2. Th ng l ng benzen
8.Thi?t b?phn ly
9.Th ng cha axit d ng
12 .Thi?t b?i?u ch
nh t l
13 .Thi?t b?i?u ch
nh nhit
3. Th ng cha hn h p axit
4 . Th ng cha axit d ng
14.Thi?t b?
15.Th ng cha benzen
h 2o
5;10;11. bm
4. S sn xut nitrobenzen theo phng php lin tc.
53
Nitrobenzen
Thiet Ke Phan Xng
9
9
dung d?ch
sau khi
trung ho
8
2
Hi
ra
H2O
H2O
Hi nu c
qu nhit
vo
H2O
Benzen
H2O
kh?n?n
dung d?ch
Na2CO3
H2O
H2O
x?t nit i thu hi

kh?n?n
Hn H p Ax?t
s sn xut nitrobenzen theo phung ph p lin tc
O AN TOT NGHIEP
Cho benzen vo thit b nitro ho (1) sau m my khuy, un

nng benzen n 40-450C v cho dn dn hn hp nitro ho vo.
54
O AN TOT NGHIEP
Thiet Ke Phan Xng
iu chnh tc cho tc nhn v khng ch nhit ca khi

phn ng nhit 400C (dng nc lm lnh). Khi cho ht hn hp
nitro ho vo thit b theo t l ta ngng lm lnh, my khuy vn lm
vic v nng dn nhit ln n 50 0C. nhit ny duy tr
phn ng khong mt gi na. Sau khi phn ng c a sang
thit b nitro ho hon ton nh kh nn thit b ny khng c b
phn lm lnh bng ng xon rut g, c cnh khuy y phn ng
coi nh hon ton.
Sau khi phn ng c lm lnh trong thit b ng xon (3)
n nhit thng, nc lnh i ngoi ng, khi phn ng i trong
ng. Tip theo khi phn ng i vo thit b lng (4). Do trng lng
ring khc nhau (
= 1,2g/cm3, axit lm vic c = 1,6g/cm3)
C H5NO2
nn thng lng c s phn chia6 thnh
2 lp. Lp trn l nitrobenzen c a lin tc vo thit b trung ho (6) v thit b ra (7). Hai thit
b ny c dng thp m, lm vic theo nguyn tc cng chiu v lin
tc, nitrobenzen c tip xc u tin vi dung dch Na 2CO3 long c
nng 6% trong thit b (6) sau hn hp ny c a vo thit
b phn ly (8). Ti thit b phn ly (8) lp trn l dung dch sau khi
trung ho c a ra ngoi cn lp di l nitrobenzen c bm vo tip
xc vi nc sch trong thit b (7). Tip theo hn hp nc v
nitrobenzen i vo thit b phn ly (8), y nc c tch ra v thu
c nitrobenzen k thut c nng 99%.Cn lp di trong thit b
lng (4) l axit lm vic cha 70-72% H 2SO4, mt t sn phm oxy
ho oxit nit c a vo thng cha s (5) v c a i s dng li.
55
HNO3
H2O
7:ni nitrator
8:thi?t b?lm l nh
9:thi?t b?phn ring
10:thi?t b?ra v trung ho
4,5:th ng lung hn h p axit,benzen

6:thi?t b?trn hn h p axit
1,2,3:th ng lung H2SO4,HNO3,H2O
H 2SO4
9
13
Axit d ng em tr?ch
ly
H2O
BENZEN
H2O
11
10
18
14
Sn phm nitrobenzen
12
Dung d?ch
NaOH
16
Axit d ng
15
17:thi?t b?phn ring
16:thi?t b?tr?ch ly
14:th ng lung axit d ng

15:th ng l?ng benzen
12:th ng lung dung d?ch NaOH

13:th ng cha axit d ng
11:th ng cha sn phm
Axit d ng
Nitrobenzen
ln benzen
BENZEN
s sn xut nitrobenzen bng phung ph p gi n o n
17
O AN TOT NGHIEP
Thiet Ke Phan Xng
4.S sn xut nitrobenzen bng phng php gin on:
56
O AN TOT NGHIEP
Thiet Ke Phan Xng
Nguyn tc hot ng nh sau:

Cho benzen vo thit b nitro ho (1) sau m my khuy, un
nng benzen n 40-450C v cho dn dn hn hp nitro ho vo.
iu chnh tc cho tc nhn v khng ch nhit ca khi
phn ng nhit 400C (dng nc lm lnh). Khi cho ht hn hp
nitro ho vo thit b theo t l ta ngng lm lnh, my khuy vn lm
vic v nng dn nhit ln n 50 0C. nhit ny duy tr
phn ng khong mt gi na, trong thi gian ny phn ng nitro ho
hu nh hon ton kt th cn li khong 1% benzen khng phn
ng . Sau a khi phn ng ln thit b lm lnh (8) dn nhit
thng ri chy xung thit b phn ring .Do c s chnh loch v khi
lung ring nn khi phn ng phn chia thnh hai lp . Lp trn l
nitrobrnzen , axt chy lin tc xung thit b ra v trung ho (10) .
thit b ny lm vic theo nguyn tc cng chu v lin tc . Sn
phm nitrobenzene c axt nh s b trung ho bi dung dch
kim Na2CO3 , sau qua thp ra bng nc sch .Sau khi ra xong ta
thu c nitrobenzen k thut v a v kho cha.
Cn lp di l axt dng c cha khong 70 n 72%
H2SO4 ,mt t sn phm oxyho , oxytnit ,nitrobenzene dng ho
tan hay dng nh tng c chy xung thng cha (13) ri bm ln
thing lng (14)
Axt c cha mt t nitrobenzene nn cn phI trch ly ra lhi
axt dng trc khi em qua c c . Dng benzen tinh khit
trch ly nitrobenzene ra khi axt dng ( vi nitrobenzene ho tan
trong benzen ) .T thing lng 14, 15 ,benzen v axt dng lin tc
chy vo thit b trch ly (16) ri xung thit b phn ring (17) do
trng lng khc nhau n nitrobenzene v benzeb c tch ra khi axt
dng . phn di thit b phn ring ch v thing cha ri em
c c hoc pha trn vi nitro ho.
Thnh phn ca nitrobenzeb k thwtj nhn c nh sau:
Nitrobenzen:
98.5%.
Benzen:
0.9%.
Nc:
Dinitrobenzen khng ln hn:
0.5%.
0.1%.
57
O AN TOT NGHIEP
Thiet Ke Phan Xng
Qua qu trnh so snh th s ny c nhiu u im nh nng

sut thit b ln, an ton, hiu sut thu c nitrobenzen cao
(nitrobenzen c nng 99%), thi gian mt m t, d c kh ho v
t ng ho, tnh trng sn xut n nh. Do s ny c la
chn trong n ny.
(kt thc!)
(n tnh ton)
58
O AN TOT NGHIEP
Thiet Ke Phan Xng
59
O AN TOT NGHIEP
Thiet Ke Phan Xng
60
O AN TOT NGHIEP
Thiet Ke Phan Xng
61
O AN TOT NGHIEP
Thiet Ke Phan Xng
Chng IV.
TNH TOAN THIET KE.
_ Thiet ke phan xng san xuat nitrobenzen

nang suat 45.000 tan/nam.
_ Cac so lieu ban au :
+ Benzen ky thuat (C6H6) 98% , 2% tap chat.
+ Axit sulfuric (H2SO4) 96%.
+ Hon hp nitro hoa co thanh phan nh sau :
88%HNO3, 8%H2SO4, 4% H2O.
+ Dung dch muoi natrricacbonat (Na2CO3) 6%.
+ Hieu suat cac giai oan :
Hieu suat chung
Nitro hoa
94%
98%
Lang
99%
Trung hoa
98%
Ra
98,5%.
Nitrobenzen ky thuat thu c co nong o

99%.
62
O AN TOT NGHIEP
Thiet Ke Phan Xng
I. TNH CAN BANG VAT CHAT THIET B NITRO

HOA.
- Qua trnh nitro hoa c tao thanh theo phan
ng :
Neu nh nha may san xuat 340 ngay trong mot
nam (25 ngay e bao dng, sa cha nh ky) th
lng nitrobenzen thu c la :
45000.1000
= 5514,706( kg / h)
25(365 25).24
Lng nitrobenzen tinh khiet thu c :

5515,706 . 0,99 = 5459,559 (kg/h)
Lng nitrobenzen tinh khiet tnh theo kmol/h :
5459,559 / 123 = 44,387 (kmol/h)
1. Lng vat chat vao thiet b phan ng :
a.Lng benzen tinh khiet vao thiet b la :
44,387 / 0,94
= 47,220 (kmol/h)
Lng benzen tinh khiet vao thiet b la :

44,220 . 78
= 3683,16 (kg/h)
Lng benzen tho vao thiet b co nong o 98%

la :
3683,16 / 0,98 =
3758,327 (kg/h)
Lng tap chat 2% vao thiet b la :

3758,327 - 3683,16 = 75,167 (kg/h).
b.Lng HNO3 a vao thiet b theo phan ng la :
47,220 (kmol/h).
Vay khoi lng HNO3 a va thiet b la :
47,220 . 63 = 2974,860 (kg/h)
V theo e bai khong cho biet nong o HNO 3 do
o ta coi HNO3 a vao thiet b dang tinh khiet :
2974,860 (kg/h).
63
O AN TOT NGHIEP
Thiet Ke Phan Xng
c.Lng H2SO4 tinh khiet can a vao trong hon hp

nitro hoa :
2974,86.8
= 270,706(kg / h)
88
Theo e bai H2SO4 co nong o 96%, do o H2SO4

tho co khoi lng la :
270,442 / 0,96 =
281,710 (kg/h).
Vay lng nc cha trong H2SO4 la :

281,71 270,442
11,268 (kg/h)
Lng nc i kem trong hon hp nitro hoa :

2974,86.4
=135,221( kg / h)
88
Tong khoi lng hon hp nitro hoa :

2974,86 + 270,442 + 135,221
3380,523
(kg/h)
1. Lng vat chat ra khoi thiet b phan ng :
-Khoi lng nitrobenzen khi ra khoi thiet b nitro
hoa:
3683,16.123
.0,98 = 5691,899( kg / h)
78
-Lng nc ra khoi thiet b nitro hoa gom :

+ Lng nc do phan ng tao ra :
3683,16.18
.0,98 = 832,961( kg / h)
78
+ Lng nc vao cung hon hp nitro hoa la :
135,221 (kg/h).
+ Tong lng nc ra khoi thiet b nitro hoa :
832,961 + 135,221
= 968,182 (kg/h).
-Lng benzen cha phan ng :

3683,16 - 3683,16 . 0,98 = 73,663 (kg/h).
64
O AN TOT NGHIEP
Thiet Ke Phan Xng
-Lng HNO3 cha phan ng :

2974,86 - 2974,86 . 0,98 = 59,497 (kg/h).
-Khoi lng H2SO4 la : 270,442 (kg/h).
-Khoi lng tap chat la : 75,167 (kg/h).
Lng vao
Ten
nguyen
lieu
Khoi
lng
(kg/h)
Lng ra
Tha
nh
pha
n (%)
Hon hp
nitro hoa:
HNO3
Ten
san
pham
Khoi
lng
(kg/h)
Than
h
pha
n (%)
C6H5NO2
5691,8
99
79,73
88
HNO3
H2SO4
2974,86
0
H2SO4
59,497
3,79
H2O
270,442
H2O
270,44
2
13,56
100
C6H6
968,18
2
1,03
135,221
Tong
3380,52
3
0,83
73,663
Benzen
Tap chat
3683,16
0
98
2
Tap
chat
75,167
1,05
Tong
7138,8
50
100
75,167
Tong
3758,32
7
Tong
cong
7138,85
0
100
II. TNH CAN BANG NHIET LNG THIET B NITRO

HOA :
Trong day chuyen cong nghe san xuat
nitrobenzen, a so cac giai oan eu lam viec nhiet
o thng, duy ch co giai oan nitro hoa va giai oan
65
O AN TOT NGHIEP
Thiet Ke Phan Xng
lam lanh th co s trao oi nhiet o. Do o can tnh

can bang nhiet lng trong thiet b nitro hoa va thiet
b lam lanh.
Trong gii han cua o an mon hoc ch tnh can
bang nhiet lng trong thiet b nitro hoa.
Phng trnh can bang nhiet lng :
Q1 + Q2 + Q3 + Q4 = Q5 + Q6
Trong o :
Q1 : Lng nhiet do nguyen lieu mang vao,
kcal/h.
Q2 : Lng nhiet do nc lam lanh mang vao,
kcal/h.
Q3 : Nhiet lng toa ra cua qua trnh nitro
hoa, kcal/h.
Q4 : Lng nhiet mat mat ra moi trng
xung quanh, kcal/h.
Q5 : Lng nhiet do nc lam lanh mang ra,
kcal/h.
Q6 : Lng nhiet do san pham mang ra, kcal/h.
1. Nhiet lng do nguyen lieu mang vao :
Q1 = QA + QB = GA . CA . tA + GB . CB . tB
Trong o :
QA : Nhiet lng do hon hp nitro hoa mang
vao, kcal/h.
QB : Nhiet lng do benzen mang vao, kcal/h.
GA : Khoi lng hon hp nitro hoa, G A =
3380,523 (kg/h).
GB : Khoi lng benzen, GB = 3758,327 (kg/h).
CA : Nhiet dung rieng cua hon hp nitro hoa,
kcal/kg.o.
66
O AN TOT NGHIEP
Thiet Ke Phan Xng
CB : Nhiet dung rieng cua benzen (coi nhiet

dung rieng cua tap chat cung nh cua benzen), C B =
0,418 (kcal/kg.o).
tA : Nhiet o vao cua hon hp nitro hoa, t A
= 250C.
tB : Nhiet o vao cua benzen, tB = 250C.
Nhiet dung rieng cua hon hp nitro hoa c
tnh theo cong thc:
C = xi . C i
Trong o :
xi : phan khoi lng cua cac cau t trong
hon hp.
Ci : Nhiet dung rieng cua cac cau t.
Hon hp nitro hoa bao gom : 88%HNO 3; 8%H2SO4;
4%H2O.
250C, cac cau t tren co nhiet dung rieng
nh sau :
C(HNO3) = 0,7 (kcal/kg.o).
C(H2SO4) = 0,565 (kcal/kg.o).
C(H2O) = 1 (kcal/kg.o).
Thay so vao ta co :
C = 0,88 . 0,7 + 0,08 . 0,565 + 0,04 . 1 = 0,701
(kcal/kg.o).
Vay
Q1 = 3380,523 . 0,701 + 3758,327. 0,418 =
3940,727 (kg/h).
2. Nhiet lng do nc lanh mang vao :
Q2 = G . C . t (kcal/h).
Trong o :
t : Nhiet o nc lanh mang vao, t = 250C.
67
O AN TOT NGHIEP
Thiet Ke Phan Xng
C : Nhet dung rieng cua nc lanh mang

vao, C = 1 (kcal/kg.o).
G : Khoi lng nc lam lanh, kg/h.
Vay
Q2 = 25.G(kcal/h).
3. Nhiet lng do qua trnh nitro hoa sinh ra :

Hieu ng nhiet cua qua trnh nitro hoa H =
-117(kj/mol) = -227,35 (kcal/kg).
Khoi lng nitrobenzen sinh ra trong mot gi la :
5459,559 (kg/h).
Vay lng nhiet sinh ra do phan ng la :
Q3 = 227,35 . 5459,559 = 1241230,739
(kcal/h).
4. Nhiet lng do nc lam lanh mang ra :
Q5 = G . C . t (kcal/h).
Trong o :
G : Khoi lng nc lam lanh (kg/h).
C : Nhiet dung rieng cua nc nhiet o
ra khoi thiet b, C = 1 (kcal/kg.o).
tc : Nhiet o cua nc ra, tc = 450C.
Thay so, ta co : Q5 = 45.G (kcal/h).
5. Nhiet lng do san pham mang ra :
Q6 = Gsp . Csp . tsp (kcal/h).
Trong o :
Gsp : Lng san pham, kg/h.
Csp : Nhiet dung rieng cua hon hp san
pham, kcal/kg.o.
tsp : Nhiet o cua hon hp san pham i ra
khoi thiet b, tsp = 500C.
Hon hp san pham co thanh phan nh sau :
68
O AN TOT NGHIEP
Thiet Ke Phan Xng
Lng nitrobenzen thu c = 5691,899 (kg/h) chiem

79,73%.
Lng benzen d va tap chat = 73,663 + 75,167 =
148,83 (kg/h) chiem 2,08%.
Lng HNO3 d = 59,497 (kg/h) chiem 0,83%.
Tong lng nc co sau phan ng = 968,182
(kg/h) chiem 13,56%.
Lng H2SO4 = 270,442 (kg/h) chiem 3,79%.
Tong : 7138,85 (kg/h).
Nhiet dung rieng cua cac cau t thanh phan
nhiet o au ra la 500C :
C(H2SO4) = 0,678 (kcal/kg.o).
C(HNO3) = 0,908 (kcal/kg.o).
C(H2O) = 1 (kcal/kg.o).
C(C6H6) = 0,445 (kcal/kg.o).
C(C6H5NO2) = 0,330 (kcal/kg.o).
Ap dung cong thc :
Csp = xi . Ci = 0,7973. 0,33 + 0,0208 . 0,445 +
0,0083 . 0,908
+ 0,1356 . 1
+ 0,0379 . 0,678 = 0,441 (kcal/kg.o).
Q6 = 7138,85 . 0,441 . 50 = 157411,643 (kal/h).
6. Nhiet lng mat mat ra moi trng :
Nhiet mat mat ra moi trng xap x bang 5%
lng nhiet ma chat tai nhiet mang vao.
Q4 = 0,05 . (Q5 Q2) = 0,05 . (45.G 25.G) = G.
Thay cac so lieu tnh c vao phng trnh can
bang nhiet lng, ta co :
3940,727 + 25.G + 1241230,739 + G = 45.G +
157411,643.
Vay G = 57250,517 (kg/h).
69
O AN TOT NGHIEP
Thiet Ke Phan Xng
Nhiet lng mat mat ra moi trng xung quanh :

Q4 = 57250,517 (kcal/h).
Nhiet lng do tac nhan lanh mang vao :
Q2 = 25.G = 25 . 57250,517
= 1431262,925
(kcal/h).
Nhiet lng do tac nhan lanh mang ra khoi thiet
b :
Q5 = 45.G = 45 . 57250,517
= 2576273,265
(kcal/h).
Bang can bang nhiet lng cua thiet b nitro
hoa.
Nhiet lng vao (kcal/h)
Nhiet lng do nguyen lieu mang vao
Q1
3940,727
Nhiet lng do nc lam lanh mang

vao Q2
1431262,92
5
Nhiet lng toa ra do phan ng nitro

hoa Q3
1241230,73
9
Nhiet lng mat mat ra moi trng

xung quanh Q4
57250,517
2733684,90
8
Tong
Nhiet lng ra (kcal/h)
Nhiet lng do nc lam lanh mang ra
Q5
2576273,26
5
Nhiet lng do hon hp san pham

mang ra Q6
157411,643
Tong
2733684,90
8
70
O AN TOT NGHIEP
Thiet Ke Phan Xng
KET LUAN
Qua mot thi gian tm kiem va nghien cu tai
lieu, em nhan thay viec a nitrobenzen vao san xuat
co tam quan trong rat ln, nitrobenzen la mot san
pham co gia tr, no c s dung rong rai trong
nhieu nganh cong nghiep. c thiet ke day chuyen
san xuat nitrobenzen phuc vu cho nganh tong hp hu
c la mot c muon ln oi vi sinh vien cong
nghe hoa hoc.
c s giup va hng dan tan tnh cua
thay giao TS. Hoang Xuan Tien em a hoan thanh
ban o an thiet ke phan xng san xuat
nitrobenzen vi nang suat 45.000 (tan/nam). Do thi
gian co han nen trong qua trnh hoan thanh ban o
an khong tranh khoi sai sot, em tat mong s ch
bao va gop y cua cac thay co e ban o an
cua em hoan thien hn.
Em xin chan thanh cam n!
Ha noi, ngay 31
thang 01 nam 2004.
Sinh vien
Tran Phi Hang.
71
O AN TOT NGHIEP
Thiet Ke Phan Xng
TAI LIEU THAM KHAO

1. Nguyen Minh Chau.
Hoa hu c.
Trng ai Hoc S Pham Qui Nhn. 1995
2. Nguyen Th Thanh.
Hoa hu c. Tap 2 Hp chat hu c mach
vong.
Nha xuat ban Giao Duc. 1998.
3. Le Mau Quyen.
Hoa hoc vo c.
Nha xuat ban Khoa Hoc va Ky Thuat. 2000.
4. Hoang Nham.
Hoa hoc vo c. Tap 2.
5. Trng ai Hoc Bach Khoa Ha Noi.
Bo mon tong hp hu c.
Ky thuat tong hp cac chat hu c trung gian.
1974.
6. Tran Xoa, Nguyen Trong Khuong, Ho Le Vien.
So tay qua trnh va thiet b cong nghe hoa
chat. Tap 1.
Nha xuat ban Khoa Hoc va Ky Thuat. 1992.
7. Nguyen Thac Cat (Chu Bien), Hoang Minh
Chau, o Tat Hien, Nguyen Quoc Tn.
T ien hoa hoc pho thong.
8. Vu The Tr.
Tong hp cac chat trung gian.
72
O AN TOT NGHIEP
Thiet Ke Phan Xng
ai Hoc Bach Khoa Ha Noi. 1974.

9. Ullmans encyclopedia of industrial chemistry. Vol
A17.
73

Asn Xuat Nitrobensen

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O AN TOT NGHIEP

San Xuat Nitrobenzen

Thiet Ke Phan Xng

SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.

Thiet Ke Phan Xng

Chng III : SAN XUAT NITROBENZEN TRONG CONG

SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.

Thiet Ke Phan Xng

GII THIEU CHUNG

Cac san pham hoa hoc noi chung va ac biet

Thiet Ke Phan Xng

nghiep a nc ta dan dan tien en mot nen cong

A. TNH CHAT CUA NGUYEN LIEU.

I.Tnh chat cua benzen [ 1 120 ].

SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.

Thiet Ke Phan Xng

*Theo quan iem co ien: phan t benzen co

Cac goc hoa tr eu bang 1200 .

o dai kien ket C C co gia tr trung gian gia

Chung ta de dang nhan thay rang do cac

SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.

Thiet Ke Phan Xng

ma kho cong hp, kho oxi hoa. No ch de pha v

Khoi lng rieng 25oC:

Sc cang be mat 200C

Nhiet dung rieng 200C

Nhiet o chp chay coc kn

Thiet Ke Phan Xng

Hang so vat ly mot so hydrocacbon thm [ 1 ] :

3. Tnh chat hoa hoc cua benzen [ 2 ].

Ni,200 - 3000C,300 atm

+ Tac dung vi clo :

Thiet Ke Phan Xng

a. Phan ng oxi hoa : Rat kho thc hien.

b.Phan ng the electrophyl SE :

SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.

Thiet Ke Phan Xng

Phan ng axyl hoa :

II.Tnh chat cua axit nitric [ 3 134 ], [ 4 183 ].

SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.

Thiet Ke Phan Xng

I. Tnh chat vat ly cua axit nitric.

Trong o nong o cua moi loai ion la 0,5 mol/lt

Nhiet o ket tinh

Khoi lng rieng 200C

Nhiet tao thanh pha long

SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.

Thiet Ke Phan Xng

Nhiet tao thanh pha kh

Nhiet hoa hi 200C

Nhiet dung rieng 200C

Nhiet nong chay

2.Tnh chat hoa hoc cua axit nitric :

Thiet Ke Phan Xng

Khac vi axit nitr, axit nitric loang khong oxi hoa

Axit nitric tinh khiet hon hp vi axit sunfuric ac

SV: Pham Ngoc Hp- Lp: Hoa Dau - K44.

Thiet Ke Phan Xng

II.Tnh chat cua axit sulfuric [3 117],[4 230]

Axit sulfuric tan vo han trong nc va qua trnh tan

Axit sulfuric tinh khiet la dung moi ion hoa ( = 100

Axit sulfuric ac nong oxi hoa c ca nhng kim

Thiet Ke Phan Xng

Tnh chat sunfo hoa cac hp chat hu c vong