BO CO CHUYN

MN: CNG NGH TNG HP

HU C HA DU

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 ti

ETHYLBENZENE
GVHD: TS. Phm Thanh Huyn
Nhm 17:
1. Hunh Anh Vit
2. Nguyn Hong Vit
3. Trn c Vinh
4. Hunh Tn Vinh
5. Bi Quang Vng
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Ethylbenzen l hidrocacbon thm c ng dng rng ri trong

cng ngh tng hp ha du.
Ethylbenzene, phenylethane, C6H5CH2CH3 l hp cht Alkyl thm
n vng, c ngha quan trng trong cng nghip tng hp hu c
ha du. Phn ln ( > 99 % ) c s dng lm nguyn liu cho qu
trnh sn xut Styrene monomer C6H5CH=CH2. 50 % ca qu trnh
sn xut benzene trn th gii. Cn li t hn 1 % ethylbenzene c
s dng lm dung mi cho sn, hoc nguyn liu cho qu trnh sn
xut diethylbenzene.
Hu nh tt c Ethylbenzene tinh khit c s dng lm
polystyrene sn xut nha v cao su nguyn liu.
6,4 triu tn / nm ca Ethylbenzene c sn xut ti M (s
liu 2001). EU, khong 5,7 triu tn c sn xut vo nm 1999.
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T l EB trn th gii gim trong nm 2008, l kt qu ca s suy thoi

kinh t th gii, dn ti nhu cu v Styrene cng dn b thu hp li. Cc
nh sn xut M, Tu u, Nht phn i vic tng gi nguyn liu,
dn ti lm gim nng sut , hnh thnh cc cng ty lin hp. Khu vc
Trung ng v Trung Quc, nng sut EB Styrene tip tc tng nh d
on do nhu cu tng. Trong khi Trung v Nam M t l s dng gim
trong 2008. Th trng th gii ang hi phc chm. Nhu cu EB trn th
gii s tng mc trung bnh hng nm l 2.9% t 2008 ti 2013, c
trng ch tng nhanh nht l khu vc Trung ng v Trung Quc
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GII THIU TNG QUT

I. NH NGHA V TNH CHT VT L
II. TNH CHT HA HC
III. PHNG PHP SN XUT
IV. NG DNG V CHT LNG
V. AN TON MI TRNG
VI. X L V BO QUN

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Phn I

NH NGHA V TNH CHT VT L

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1. nh ngha:

- Danh php IUPAC: etylbenzen

- Tn khc l : etylbenzol,phenyletan,EB
- Cng thc ha hc: C8H10

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Cng thc phn t

Cu trc

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2. Tnh cht vt l
iu kin thng, Ethylbenzene l cht
lng trong sut, khng mu vi mi thm
c trng.
Ethylbenzene c kch ng cho da v mt.
Tng i c hi khi ung phi, ht th v
hp ph qua da.

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10

Di y l mt vi tnh cht
vt l ca Ethylbenzene:
Khi lng ring :
- 150C :
- 200C :
- 250C :

0.87139 g/cm3
0.867g/cm3

0.86262 g/cm3

Nhit nng chy : -94. 9490C

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11

Di y l mt vi tnh cht vt l
ca Ethylbenzene: (tt)
Nhit si 101.3 kPa : 136.2 0C
Ch s khc x + 20 0C :
+ 25 0C :

1.49588
1.4932

p sut ti hn : 3609 kPa ( 36.09 bar )

Nhit ti hn :
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344.02 0C

12

Di y l mt vi tnh cht vt l
ca Ethylbenzene: (tt)
Nhit chp chy:

15 0C

Nhit t bc chy :

460 0C

Gii hn chy
n nhit
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+ di:1 %
+ trn : 6.7 %
+ nng chy : 86.3 J/g
+ha hi: 335 J/g
13

Di y l mt vi tnh cht vt l
ca Ethylbenzene: (tt)

nht ng hc + 37.8 0C : 0.6428*10 6m2/s

+ 98.9 0C : 0.39*10 6m2/s
Sc cng b mt : 28.48 mN/m
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14

Di y l mt vi tnh cht vt l ca
Ethylbenzene: (tt)
Nhit lng ring:
+ kh l tng, 25 0C : 1169 Jkg-1K-1
+ lng, 25 0C
: 1752 Jkg-1K-1
Gii hn nn :

0.263

ha tan trong nc 20 0C : 0,015g / 100ml

T trng hi (khng kh =1)
im
bc
chy
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:3,7
:15-20 0C

15

Phn II
TNH CHT HA HC

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16

Trng thi xi ha

Etyl benzen vo qu trnh oxy ha trong cc tc nhn oxy ha khc nhau

cho cc sn phm khc nhau nh hydroperoxide Ethylbenzene,
acetophenone v thm ch acid benzoic.

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17

Trng thi xi ha (tt)

Tt c nhng phn ng trn l phn ng oxy ha ca
ethyl benzene vi nhng cht phn ng khc nhau nh:
+Phn ng 1 ha cht c s dng l NaCr2O7
+Phn ng 2 ha cht c s dng l CrO3
+Phn ng 3 c tc nhn oxy ha l Mg(CH3COO)2
+Phn ng 4 c tc nhn oxy ha l oxy trong khng kh

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18

kh hir ca Ethylbenzene
asstyrenecsnxuttrongcngnghiptqutrnh
khhircaEthylbenzene
CH2

CH3

CH

CH 2

Cr3O3 ,Al2O3
600o C

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19

Phn ng etylbenzen vi Br2

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20

Phn ng cng H2
CH2

CH3

CH2
+ 3H2

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CH3

Ni
o
110 atm,125 C

21

Phn ng halogen ha nhm ankyl

CH2

CH3
CH2
+ Cl 2

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Cl

CH3

CH2

CH2Cl

22

Phn 3:
PHNG PHP SN XUT

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23

Cc phng php sn xut Etylbenzen:

C 2 phng php sn xut etylbenzen:
-Chng hn hp hi Hydrocacbon thm C8
-Ankyl ha benzen bng etylen

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24

Qu trnh chng tch t hn hp C8:

Khong 1% etylbenzen c sn xut t qu trnh

ny,thng kt hp vi sn xut xylen t sn phm ca qu
trnh Reforming
Sn xut etylbenzen t ngun ny tin hnh phn ln bng
chng ct,qu trnh tch rt kh khn,cng ngh tin hnh
chng trong khong hp (siu chng phn on)
Cng ngh u tin ca hng Cosden Oil and Chemical
Company ra i nm 1957,lin kt vi Badger Company.
Qu trnh tch yu cu 3 thp chng,mi thp hn 100
a.Nhiu nh my c xy dng M,chu u,Nht
trong nhng nm 60,tuy nhin do vn u t v gi nng
lng tng nn phng php ny khng c tnh cnh tranh.
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25

Qu trnh ankyl ha bng Etylen:

c tin hnh ch yu theo 2 phng php:
-Tin hnh trong pha lng
-Tin hnh trong pha hi vi xc tc rn tng c nh

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26

Qu trnh ankyl ha bng Etylen (tt)

Qu trnh pha lng:
Qu trnh alkyl ha vi xc tc axit Lewis,khng s dng
Zeolit
Qu trnh alkyl ha trn xc tc Zeolit trong pha lng

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27

Qu trnh ankyl ha bng Etylen (tt)

Qu trnh alkyl ha trn xc tc Zeolit trong
pha lng:
Cng ngh pha lng s dng xc tc Zeolit bt u c
thng mi ha t nm 1990,nh my u tin vn hnh bi
Nippon SM ca Nht da trn cng ngh ca hng ABB
Lummus Global and Unocal,cng ngh ny s dng xc tc
Zeolit Y v gn y l Zeolit siu n nh
Cng ngh EBMax ca Mobil-Badger da trn xc tc
Mobil MCM-22
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28

S cng ngh ca 2 cng ngh ny tng i ging nhau:

Figure 2.Lummus/UOP ethylbenzene process

a)Alkylation reactor; b) Transalkylation reactor; c) Benzene column; d) Ethylbenzene
column; e) Polyethylbenzene column.
Figure
3.Mobil Badger EBMax process
a) Alkylation reactor; b) Transalkylation reactor; c) Benzene column; d) Vent-gas
column; e) Ethylbenzene column; f) Polyethylbenzene column
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29

Qu trnh pha hi
Gm hai qu trnh:
- Qu trnh alkyl ha xc tc axit Lewis,khng
s dng Zeolit
- Qu trnh alkyl ha pha hi trn Zeolit

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30

Qu trnh alkyl ha xc tc axit Lewis,khng

s dng Zeolit
Nm 1960 c quy trnh c pht trin bi UOP da
trn xc tc BF3.
*iu kin vn hnh:
- Nguyn liu:benzen kh,etylen v BF3
- p sut cao:2,5 3,5 Mpa
- Nhit thit b phn ng thp:100 150 oC
- Nhit thit b chuyn v alkyl: 180 230 oC
Kt qu thu c etylbenzen c nng 99,9%
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31

Qu trnh alkyl ha pha hi trn Zeolit

Nm 1970,cng ngh ca Mobil-Badger xut hin v
c cng nhn l cng ngh alkyl ha trong pha hi
thnh cng nht vi xc tc Zeolit tng hp ZSM-5.
*iu kin vn hnh:
-Nguyn liu t etylen (15%)
-Xc tc ZSM-5 hot tnh cao
-p sut : 1-3 Mpa
-Nhit : 400 450 oC
-C 2 thit b hot ng thay phin:1 thit b hot ng
v 1 thit b ti sinh xc tc gip qu trnh hot ng lin
tc.
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32

Qu trnh alkyl ha pha hi trn Zeolit:

S cng ngh:

Figure 4.Third-generation Mobil Badger ethylbenzene process

a)Reactor-feed heater; b) Alkylation reactor; c) Benzene recovery column; d)Ethylbenzene
recovery column; e) Polyethylenebenzene recovery column; f) Secondary reactor; g) Stabilizer

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33

Cng ngh sn xut Etylbenzen mi hin nay:

Cng ngh sn xut etylbenzen trong pha hn
hp c a ra bi CD Tech,l cng ty lin hp
ca ABB Lummus Global v Chemical Research
and Licensing.Nh my u tin ra i nm
1994 v ti nm 1999 c 3 phn xng i vo
vn hnh

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34

Cng ngh sn xut Etylbenzen mi hin nay

S cng ngh

Figure 5.CDTech ethylbenzene process

a) Finishing reactor; b) Transalkylator; c) Alkylator; d) Benzene stripper; e)Ethylbenzene
column; f) Polyethylbenzene column
BFW = boiler feed water, PEB = polyethylbenzene
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35

Phn 4:
ng dng v cht lng

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36

ng dng
Ethylbenzene gn nh c quyn (> 99%)
s dng sn xut styrene monomer
[CAS RN: 100-42-5], C6H5 CH = CH2
Hu ht monome styren (Ts = 145,20C)
c sn xut bng phng php dehydro
ha etylbenzen hoc l ng sn phm ca
qu trnh sn xut propylen oxyt
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ng dng
C ch phn ng:

H=125Kj/mol
Phn ng l phn ng thun nghch,thu nhit mnh,tng th tch,thch
hp tin hnh nht cao p sut thp
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ng dng (tt)
It hn 1% ca Ethylbenzene sn xut c s dng
nh mt trung gian sn xut diethylbenzene,
acetophenone v ethylanthraquinone, nh l mt
thnh phn ca nha ng v naphtha, v nh mt
cht chng kch n cht ph gia nhin liu v
gasolines.
Trong nhng ng dng nh, quan trng nht l trong
ngnh cng nghip sn ph nh l mt (Xylen hn
hp) dung mi cho sn, keo xt, v vecni.
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Cht lng
a s cc nh sn xut xc nh c im k thut
bn hng ca h theo tiu chun M v th nghim
phng php ASTM D3193 "Tiu chun k thut i vi
Ethylbenzene ".
Cc thng s chnh ca mt c im k thut bn hng
thng thng l: ti thiu tinh khit ca 99,5 wt. %
V ti a mu sc ca 10 trn cc-Cobalt Quy m
Platinumtrong khi cc tp cht quy nh v nng ca
h ph thuc vo l trnh sn xut lm vic, cng vi cc
c tnh hiu sut cy trng.
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40

Cc kha cnh kinh t

C 99% Ethylbenzene c s dng c sn xut
styrene monomer trn ton th gii.
Nhng nm 1960 v u nhng nm 1970 t l tng
trng hng nm ca styrene v Ethylbenzene trung
bnh 10%.
Khong 15% ca Ethylbenzene c tiu th trong sn
xut hp tc ca styrene v oxit propylen. Cc nh my
ny cung cp mt li th kinh t v gi tr ca sn phm
propylen oxit ng.
Sn xut nhiu ti cc nh my H Lan, Ty Ban Nha,
Nht Bn, Singapore, Hn Quc v Hoa K.
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41

Cc kha cnh kinh t

Nm
1999 trn
ton
th
sut (trong 103 t / a) theo vng nh sau:
North America
South America
Western Europe
Eastern Europe
Korea/Taiwan/China
Japan
Middle East and Africa
Southeast Asia/Australia
Total
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gii cng
7700
330
5900
1300
3800
3500
680
500
24 700
42

Phn 5:
An ton mi trng

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43

1.Mi trng
Ethylbenzene gim nhanh chng trong
mi trng khng c ngha sinh hc
tch ly. N ni trn mt nc v nhanh
chng bay hi.
Theo ch th EU Ethylbenzene hin
khng phn loi l nguy hi cho mi
trng.
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44

2.Con ngi
Theo ch th EU v cc cht nguy him nh hng n
sc khe th Ethylbenzene c phn loi l kh c hi
khi ht. Nu ht hi Ethylbenzene nng cao trong
thi gian di c th gy ra chng mtm nhc u, bun
ng, bun nn v mt phi hp.
V tnh n phi khng gy thng tch nhng nu nut
mt lng ln c th gy t vong.
Etylbenzene c th gy kch ng nh n trung bnh
n da v mt. Thng xuyn tip xc s dn n kh
da v vim da.
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45

Phn 6:

X l v bo qun

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46

1.X l
Trnh tip xc vi da, mt v qun o. Ch s
dng ni thng gi tt.
Ethylbenzene hi c th to thnh hn hp n vi
khng kh. Cc gii hn n trong khng kh ( p
sut kh quyn , o ti 140 o C) l h n gii hn
(LEL) : 1.2% vol,thng n gii hn (UEL) :
8.0% vol.An ton thc hnh lu tr, x l v vn
chuyn phi tp trung vo cc bin php phng
nga trnh s nh la ca Ethylbenzene. Dp tt
ngn la bt thng, hy b ngun nh la,
trnh tia la, khng ht thuc.
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1.X l (tt)
Ethylbenzene l mt cht lng d chy
cao, nhit chp chy 15 20 oC v
vy phi x l nhit mi trng xung
quanh, trnh xa nh nng mt tri trc
tip v cc ngun nhit.
Ethylbenzene c th tch t tnh in do
phi ch n cc bin php chng li
tnh x ( tia la gy nguy him).
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48

2.Bo qun
Bo qun trong thng cha s dng thp
khng g, km xilicat, nha epoxy.
Khng ph hp vi nguyn vt liu butyl,
cao su Neoprene hoc nitrile t nhin v
hu ht cc sn phm nha.

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XIN CHN THNH CM N!

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