Ph lc 1 - Tng hp dibenzylideneacetone

GII THIU
Dibenzylideneacetone hay cn c bit vi tn thng mi l dibenzalacetone (DBA) l mt hp cht
hu c tng hp.
CTPT: C17H14O, tn IUPAC: 1,5-diphenyl-1,4-pentadien-3-one
Nhit nng chy: 107-113 oC (ng phn trans, trans)
Dibenzalacetone l cht rn mu vng nht khng tan trong nc, tan tt trong n-hexane, toluene,
benzene v tan va phi trong C2H5OH, CH3COOC2H5...

Hnh 1. Cng thc cu to ca dibenzylideneacetone (hay dibenzalacetone DBA).

Vi cng thc cu to c bit (hnh 1), DBA c kh nng hp th tia UV v bo v da khi tc hi ca
nh nng mt tri. Hn na, DBA khng gy kch ng cho da. Do , DBA c s dng ph bin trong cc
sn phm chng nng. Ngoi ra, DBA cn c bit n nh mt ligand quan trng trong lnh vc ha hc
c kim.
Trong quy m cng nghip cng nh phng th nghim, DBA thng c tng hp bng phn ng
ngng t Claisen-Schmidt gia benzaldehyde v acetone, vi xc tc l dung dch NaOH
(hnh 2).

Hnh 2. Phn ng ngng t Aldol gia benzaldehyde v acetone trong dung dch NaOH
DBA to thnh cha trn 90% ng phn dng trans, trans. Bn cnh phn ng chnh ni trn, cn c 1 s
phn ng ph cnh tranh bao gm: phn ng ngng t Aldol ca acetone, phn ng Cannizarro ca
benzaldehyde hay ch c monobenzalacetone c hnh thnh

HNG DN TH NGHIM
Dng c v ha cht
Ha cht
Acetone
Benzaldehyde
NaOH rn
Ethanol

1 Pipet 5 ml
1 Erlen 150 ml
1 ng ong 50 ml
1 Bp t + C t

Dng c
1 Erlen 250 ml
1 Becher 50 ml
1 Phu lc Buchner
1 Becher 250 ml
1 Bnh lc chn khng
1 a khuy
Giy lc
1 Nhit k
1 B iu nhit

Quy trnh th nghim

-

Ha tan 3.5 g NaOH trong erlen (loi 250 ml) vi 35 ml nc v 28 ml ethanol. Khuy u v n

nh nhit trong khong 20oC n 25oC.

-

Trn 3.6 ml (0.035 mol) benzaldehyde v 1.3 ml (0.0175 mol) acetone trong becher 50 ml, lc nh

cho tan ht. Cho mt na hn hp ny vo dung dch NaOH. Khuy u v n nh nhit trong khong
20oC n 25oC. Sau 15 pht phn ng, cho tip phn cn li vo erlen (trng li becher vi khong
5 ml cn) v tip tc phn ng xy ra thm 30 pht (vn trong khong nhit trn).
-

Lm lnh erlen trong b trong khong 15 pht ri lc di p sut thp (1 lp giy lc). Phn tn

li sn phm vo 200 ml nc, khuy k ri lc di p sut thp (1 lp giy lc), ra sn phm th bng
nc.
-

Cho DBA th vo erlen (loi 150 ml), thm khong 20 ml cn ( nhit si) ri t ln b iu

nhit, lc u erlen. Tip tc thm chm cn ( nhit si) n khi DBA tan va ht. Lm ngui v
nhit phng ri lm lnh trong b . Lc di p sut thp, ra DBA bng mt t cn lnh.
Mt s ch quan trng
-

Benzaldehyde l hp cht rt khng bn trong khng

kh v nh sng. Khi ly benzaldehyde, khng pipet
chm y chai, khng a chai ra khi hp giy v y
cht np sau khi s dng.

Cc dng c ly ha cht (pipet, a nha) phi

hon ton kh ro.

Sinh vin ly nhanh v chnh xc cc ha cht

(benzaldehyde, acetone, NaOH) theo yu cu th
nghim.

Cc cha hn hp tc cht nn c y cht trong sut qu trnh th nghim.

Pipet sau khi ly benzaldehyde phi c ra sch ngay bng cn v t ng v tr quy nh.

Cch bo qun v s dng cc ha cht khng bn, d ht m hoc d bay hi trong phng th
nghim l mt trong nhng yu cu ca bi th nghim ny. Do , nhm th nghim s b pht (tr
1-2 im) nu khng thc hin nghim tc cc ch trn.