You are on page 1of 2

React. Kinet. Catal. Lett., Vol. 47, No.

i, 65-71 (1992)

RKCL 1098

CATALYTIC PREPARATION OF M E S I T Y L OXIDE FROM ACETONE

N. Si~ul, N. C i k o v i ~ x, N. W o l f and J. J e l e n ~ i ~

Faculty of T e c h n o l o g y , University of Zagreb, Savska cesta 16,


41000 Zagreb, Croatia
XFaculty of F o o d T e c h n o l o g y and B i o t e c h n o l o g y ,
Zagreb, Croatia
Received November 5, 1991
Accepted November 19, 1991

In the p r o c e s s of the a l d o l condensation of a c e t o n e the


preparation of m e s i t y l oxide has b e e n s t u d i e d w i t h re-
spect to the t e m p e r a t u r e and the n a t u r e of c a t a l y s t .
Strong basic ion e x c h a n g e r s Ionenaustauscher III (Merck
III) and L e w a t i t MP 500 w e r e used in the t e m p e r a t u r e
range from 0 to 50~ Better results are a c h i e v e d with
Merck III, as is e v i d e n t from DAA/MO yields, rate con-
stants and e n e r g y activation values. Empirical expres-
sions for D A A / M O production are given.

Hcc~efloBaaM B~M~HMe TeMnepaTypN M npMpo~N K~TSJIM3aTOp~ H~

npouecc anb~onbHoM KOH~eHCS/IMM ~eTOHa npM noayqeHHM OKMCM

Me3HTHna (OM). HCHOnB3OBSJIH CMnbH~e OCHOBH~e HOHOO6MeHHHKH

MapKH Ionenaustauscher Ill (Merck Ill) M Lewatit MP 500 B

MHTepBa~e TeMnepKTyp OT 0 ~0 500C. HCXO~ H3 B N X O B O B 7]AC/OM


(/IAC=~HaUeTOHOB~M CHHpT), BenHqHH KOHCTS/4T C K O p O C T e M H sHep-

FM~ aKTMBaUMM, ayqmMe pe3ynbTaT~ ~OCTMPH~rrN n p M MCnOnbSOBa-

HMM Merck III. ~pMBO~STC~ 3MnMpMHeCKMe BNpaxeHM~ npOMSBO~-

C T B a ~AC/OM.

Akad6miai Kiad6, Budapest


v
SISUL et al.: MESITYL OXIDE

INTRODUCTION

In the aldol c o n d e n s a t i o n of acetone into d i a c e t o n e alcohol


(DAA) numerous by-products, such as mesityl oxide, isophorone
mesitylene, phorone and 3,5-xylenol are also obtained. Various
catalysts are used for this purpose, especially basic catalysts
like barium, c a l c i u m and m a g n e s i u m hydroxide or alumina [1-3].
The a p p l i c a t i o n of strongly basic anion exchange resins is also
known [4-6]. Mesityl oxide (MO) is one of the main b y - p r o d u c t s
in the process of DAA synthesis. It is p r e d o m i n a n t e l y formed
at higher temperatures according to the schematic equation:

CH 3 CH 3
2 C<3C=O ~C-CH-C-CH ~C-CH-C-CH + H20
/ ~ /I 2, 3 ~ / - II 3
c~3 cH3 oH o cH 3 o

acetone diacetone alcohol mesityl oxide

Thus in many studies of d i a c e t o n e alcohol condensation from


acetone the study of mesityl oxide formation is also included.

EXPERIMENTAL

In previous works the catalytic preparation of diacetone


alcohol was studied [7,83. Simultaneously the formation of me-
sityl oxide was also determined. In this work its p r o d u c t i o n
is studied w i t h respect to the t e m p e r a t u r e and the catalyst
nature. The e x p e r i m e n t s were carried out in the t e m p e r a t u r e
range from 0 to 50~ using strongly basic ion exchangers
L e w a t i t MP 500 and I o n e n a u s t a u s c h e r III (Merck III) as cata-
lysts. All the e x p e r i m e n t s were p e r f o r m e d in a l a b o r a t o r y set-
up for batch p r o d u c t i o n described earlier [73. Preparation of
c a t a l y s t was done by 24 h swelling in d i s t i l l e d water and 2 h
immersion in 1 M NaOH, then rinsed with water and ethanol. A
gas c h r o m a t o g r a p h y m e t h o d was used to identify reaction prod-
ucts.

66

You might also like