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Jozmim: Feb. 17, 1953 B. V. Aller Etal
Jozmim: Feb. 17, 1953 B. V. Aller Etal
17, 1953
B. v. ALLER ETAL
2,628,983
MANUFACTURE oF PHENoLs
Filed Jan. 29
1948
JOZmI
HEILNVOBG
'1358EA
HOLVLISV
INVENTORS.
BY
A Gv E N T
2,628,983
(Cl. 260-621)
duced.
The present invention is based on the discovery
that when benzene derivatives of the kind men
tioned are oxidised in the liquid phase by gaseous
oxygen, percompounds are formed.
These are
'
2,628,983
peratures.
By carrying out the process in this way it is
possible to obtain yields of phenols of more than
80% calculated on the total percompounds pres
ent in the reaction mixture. This is the more
surprising in view of the presence of the initial
alkyl benzene during the decomposition of the
said peroxides.
The recovery of the products resulting from the
process according to the present invention may
be achieved in various Ways.
When work
ing.
5 ,
verted.
The
treatment
was
continued
for
of phenol.
tions during the oxidation to maintain the emul
The residue of the fractionation, which still
sion), was heated at 85 C. with oxygen till the
formed two phases, was made strongly alkaline,
oil layer contained 44.8% w./v. of peroxide (cal
and the alkaline solution decanted from undis
culated as isopropyl benzene peroxide).
. solved oil. 34.8 grams of phenol were found in
50 cc. of the oil layer were agitated with a con
this alkaline solution, which corresponds to a
centrated solution of sodium hydroxide. The
yield of '70% on the peroxide in the original oil
aqueous liquid was acidied cautiously with
layer from the oxidation.
dilute sulphuric acid and the resultant mixture
Example 4
was boiled under reilux and finally distilled while
the liquid volume in the boiling flask was main
The effect of stirring on the rate of decomposi
tained by addition of water. The distillation was
tion of the percompounds in the acid treatment
stopped when the distillate gave a negative test
is seen from the following table.
for phenol. 6.7 grams of phenol were obtained
75 cc. of a peroxide solution in isopropyl ben
in this way, which corresponds to a yield of 48.5%
zene were mixed with '75 cc. of a 10% w./w. aque
on the peroxide contained in the oil layer from
ous sulphuric acid and refluxed gently, in one
the oxidation.
case wtih stirring, in the other without it. Peri
Another 50 cc. of the oil layer were reiiuxed
odically samples were Withdrawn and analysed
with 90 grams of a 10% sulphuric acid for 90
for percompound content in the oil phase.
Tune/mm.
Dpercent
Sitio
ecompoA
Unstirred
50
68
78
Example 2
2G
B8
46
85
57
S9
93
6l
76
is
Stm ed
e
91
Example 5
composed.
'72% of theory.
Example 3
2,628,983
7
pounds is practically complete, and separating
Example 7
'
2,628,983
phenol, which comprises oxidizing isopropyl
benzene with molecular oxygen, whereby per
compounds are produced therefrom, terminating
the oxidation While the resulting reaction mix
ture contains a substantial amount of unreacted
acetophenone.
10
produced.
2,628,983
12
l1
REFERENCES CITED
The following references are of record in the
le of this patent:
Number
2,434,888
,2,527,640
OTHER REFERENCES
Hock et al., Berichtee, vol. '77 (1944), pp. 25%
26.4 (8 pages). Abstracted in C. A. 39, col. 3526,
'7 (Zpages) (1945).