Bi 1: PHN NG ESTER HA TNG HP ASPIRIN

(ESTERIFICATION REACTION THE SYNTHESIS OF ASPIRIN)

I. MC CH
Tm hiu qu trnh tng hp Aspirin trong phng th nghim, xc nh hiu sut ca phn
ng.
II. C S L THUYT
Aspirin hay cn gi l acid salicylic l mt loi ester.
L cht kt tinh khng mu tan t trong nc nhng li tan nhiu trong ru. V th m
ru c dng kt tinh li Aspirin.
Phn ng iu ch Aspirin chnh l phn ng ester ha gia acid salicylic v anhydric
acetic trong mi trng acid. Phn t ca acid salicylic cha hai nhm chc trong c
mt nhm chc l phenol v mt nhm chc l acid cacboxylic. V vy n c th to
thnh mt ester vi vai tr ca mt ancol phn ng vi acid acetic to thnh acetyl
salicylic. Tuy nhin, Aspirin thng c u ch bng cch dng anhyric acetic v
anhyric acetic hot ng mnh hn acid acetic. Salicylic acid c acetyl ha bng acetic
anhydride cho aspirin (sn phm chnh) v acid acetic (sn phm ph).
Cc tc cht s dng trong qu trnh tng hp Aspirin:
- Salicylic acid ( COOH OH H C ) (
4 6
):
L mt acid monohydroxybenzoic (gm phenolic v beta hydroxy acid), acid
hu c ny kt tinh khng mu c s dng rng ri trong tng hp hu c
v c cc chc nng nh l mt hormone thc vt.
Thng tin an ton: Gy kch ng mi, hng, mt v da.
ng dng: Ngoi vic c dng tng hp Aspirin (Acetyl salicylic ),
acid salicylic cn c dng iu tr mn trng c.
iu ch:



- Acetic anhydride hay cn gi l Ethanoic anhydride ( ( ) O CO CH
2 3
):
L mt cht lng khng mu, c mi mnh ca acid acetic. Acetic anhydride
thy phn to thnh acid acetic:
( ) COOH CH O H O CO CH
3 2 2 3
2 +
Thng tin an ton: Kch ng nng gy bng da, mt, ri lon h hp.
ng dng: c dng tng hp Aspirin, s dng trong bo qun g thng
qua ni hp, ngm tm ko di bn ca g, ngoi ra ng dng quan
trng trong vic chuyn i cellulose (acetate cellulose), l thnh phn ca
phim nh v vt liu ph khc.
iu ch:
( ) O CO CH CO COOCH CH
2 3 3 3
+

- Acid sulfuric (
4 2
SO H ):
L mt acid v c mnh, ha tan c trong nc theo bt k t l no. Acid
sulfuric c dng du trong sut, khng mu, khng mi.
Thng tin an ton: Gy kch ng v bng nng, nh hng ti phi, ng tiu
ha.
ng dng: Acid sulfuric c dng trong sn xut phn bn, ch bin qung,
tng hp ha hc, x l nc thi v tinh ch du m.
iu ch: Acid sulfuric c iu ch t lu hunh, oxy v nc theo cng
ngh tip xc.
o Trong giai on u ngi ta t lu hunh to ra ixit lu hunh
( ) ( ) ( ) k
t
k r
SO O S
o
2 2
+
o Sau n b oxi ha thnh trioxit lu hunh bi oxy vi s c mt ca cht
xc tc oxit vanadi (
5 2
O V )
( ) ( ) ( ) k
xt
k k
SO O SO
3 2 2
2 2 +
o Cui cng trioxit luu hunh c x l bng nc ( trong dng 97-98%
4 2
SO H
cha 2-3% nc ) sn xut acid sulfuric 98-99%
( ) ( ) ( ) l l k
SO H O H SO
4 2 2 3
+
o Bn cnh ,
3
SO cng b hp th bi
4 2
SO H to ra leum (
7 2 2
O S H ), cht
ny sau c lm long to thnh acid sulfuric m c.
( ) ( ) l l
O S H SO SO H
7 2 2 3 4 2
+
( ) ( ) ( ) l l l
SO H O H O S H
4 2 2 7 2 2
2 +
Phng trnh phn ng:

Phn ng ester ha l phn ng thun nghch. V vy khi t trng thi cn bng
th hiu sut khng vt qu 66,7 %. Tuy nhin c th chuyn dch cn bng theo
chiu thun bng cch:
Dng d mt trong cc cht tham gia phn ng.
Gim nng cht to thnh trong phn ng.
Dng xc tc thc y phn ng nh: acid sunfuric (
4 2
SO H ), nha trao i ion,
cc mui acid kim loi...
C ch phn ng:


iu kin phn ng xy ra:
Tin hnh phn ng trong chu nc nhit C
o
80 70 , vi thi gian l 15
pht, sau phn ng lm lnh hn hp trong chau nc .
III. TIN HNH TH NGHIM
3.1. S quy trnh tin hnh th nghim





Nhit : 7080C
Thi gian: 15 pht
Lc u hn hp
20ml nc lnh









Salicylic acid
(3g)
Anhydride acetic
(6ml)
Acid sulfuric
(510 git)
Phn ng
Lm lnh
Lc chn khng
Nc lc
Lm kh
Sn phm


3.2. Thuyt minh quy trnh
Cn 3,0 g acid salicylic, cho vo erlen 250ml, dng pipet ht 6,0 ml anhydrid acetic v
cho vo erlen (tin hnh cn thn trnh anhydrid acetic tiep xc vi da v mt.
Tip theo cho t t 5-10 git
4 2
SO H m c vo erlen v lc u hn hp. t hn hp
phn ng vo chu nc nhit 7080C trong 15 pht tin hnh phn ng.
Sau khi phn ng xong, cho vo 20 ml O H
2
, lm lnh trong chu nc . Nu cha
thy xut hin tinh th th ly a thy tinh c nh vo thnh bnh to mn kt tinh
hoc l khuy nh hn hp.
Khi hn hp kt tinh th tin hnh lc (lc chn khng), trong qu trnh lc ta ra li
sn phm bng nc ba ln (khong 23 ml/ln). Lm kh sn phm di nh nng mt
tri hoc t sy (t<100C).
IV. KT QU TH NGHIM
Sn phm thu c qua qu trnh iu ch trn l: Aspirin
Lng Aspirin thu c thc t l:
( )
g m
tt Aspirin
987 , 1 =

Theo phn ng ta c:
( )
mol n n
lic AcidSalicy lt Aspirin
0217 , 0
138
3
= = =

( )
g m
lt Aspirin
9 , 3 180 0217 , 0 = =

Vy hiu sut ca phn ng l:
95 , 50
9 , 3
987 , 1
100 = = =
lt
tt
m
m
H
%
Cch tng hiu sut: L thay i phng php tch chit sn phm, mt phng
php tch chit cho nng sut cao hn l acid ha bi acid phosphoric v un
cc cht phn ng ngc dng nc trong mt bn cha nc si vi thi gian
khong 40-60 pht.
ng dng ca sn phm: Aspirin c tc dng gim au, h st, chng vim, ngoi ra cn
c tc dng chng kt tp tiu cu, khi dng liu thp ko di c th phng nga au tim
v tc nghn trong mch mu.