chemlul Engiaetrin&3sdeaee, 1058.

vol. a, pp.lea to lea. PasalmllPrenLtd.

Production of phenol from cumene

J. P. FORTUIN* and H. I. WATERMAN
Laboratory of Chemical Engineering, The University, Delft, Holland
(Rembed 15 June 1958)

Summary-This paper deals with the preparation of phenol from cumene. Liquid-phase
oxidation of cumene with molecular oxygen produces cumene hydroperoxide, which is subse-
quently decomposed catalytically into phenol and acetone.
The oxidation requires the use of thoroughly purified cumene. It was carried out in a
copper vessel at l!W’C, good conversions and high yields of cumene hydroperoxide being obtained.
For the decomposition of cumene hydroperoxide into phenol and acetone sulphur dioxide
was used as the catalyst. Thii reaction gave optimum results when carried out in a film reactor.
A description is given of an apparatus for continuous preparation of phenol from cumene
and a simplified flow sheet for product&on on a larger scale is added.
R6sum4-L’auteur Btudie la preparation de phenol B partir de cumene. L’oxydation en phase
liquide du cum&e par l’oxygene mol&mlaire donne l’hydroperoxyde de cumene qui est ensuite
decompose par voie catalytique en phenol et en acetone.
L’oxydation demande l’emploi de cum&e de haute puret.4. Effectub dens un recipient en
cuivre B 1WC elle donne de bonnes transformations et de hauts rendements en hydroper-
oxyde de cum&e.
Pour la decomposition en phenol et en acetone de l’hydroperoxyde ainsi obtenu l’auteur utilise
l’anhydride sulfureux SO, comme catalyseur. On obtient les meilleurs rksultats lorsque la
decomposition est ex&x&&. dans un r&cteur oit le liquide est decompose sous fonne dune couche
mince.
L’auteur d&it un appareil pour la preparation continue de phenol B partir de cum&e et un
schema simplifie d’op&ation pour la production B plus grande Cchelle.

INTRODUCTION PREPARATIONOF CUMENEHYDROPE~OXIUJS

HOCK and LANG prepared cumene hydroperoxide
Recently a new process for commercial phenol
by bubbling dry oxygen through cumene heated
production has been announced, with cumene
at 85°C under ultra-violet radiation [2]. Only
(isopropylbenzene) as starting material [l]. The
7& per cent of the cumene had been converted to
process is obviously based upon the reactions
the hydroperoxide after 24 hours.
first disclosed by HOCK and LANCJ[2].
Oxidation of a cumene-water emulsion system
gave conversions to cumene hydroperoxide of
CHs CH,
I
80-40 per cent and yields of 80-90 per cent [8].
CH, CII CHs-C-O-O-H OH CH, About 8 per cent wt of cumene hydroperoxide
1 ,
was formed per hour in the hydrocarbon layer.
Still better reaction rates were obtained when the
cumene was oxidized as such at llO-180°C [4].
cumene cumene phenol acetone At 120°C 7 per cent wt of cumene hydroperoxide
hydroperoxide was formed in the liquid per hour.
Previous addition of cumene hydroperoxide to
The further development of this new phenol the cumene to be oxidized is claimed to shorten
synthesis necessitated a laboratory investigation the induction period and thus to increase the
into both reactions. The present paper discusses reaction rate [5].
the main features of this work. During the As catalysts CaCO,, Na&O, [6] or lead salts
investigation several patents and applications [7] are mentioned. Even with the aid of these
were published by others interested in the field. catalysts the reaction rates remained low (about

* Present address : KoninMajkt/SheU-Laboratorium Am&dam Holland.

182
 : production of phenol from cumene
J. P. F~RTUIN and H. I. WATERMAN

1-8 per cent wt of cumene hydroperoxide formed was checked with pure cumene hydroperoxide
per hour). (prepared from the recrystallized sodium salt, cf.
It may be concluded that the oxidation rates HOCK and LANK [2]) and with solutions of cumene
generally are very low. The yield of cumene hydroperoxide in cumene of known strength. The
converted into cumene hydroperoxide may be as results are summarized in Table 1.
high as 90-100 per cent, however. One of the Duplicate determinations were reproducible
objects of the investigation was therefore to within 0.1 per cent. The table shows that the
increase the reaction rate whilst maintaining a results are somewhat too low. The deviation
high yield, so as to develop an oxidation process increases with increasing cumene hydroperoxide
attractive for the manufacture of cumene hydro- content. No correction was made for this devia-
peroxide on a larger scale. tion in the experimental work.
Technical cumene from several sources was
used as the starting material. APPARATUS
The first oxidation experiments were carried out
ANALYTICALPROCEDURE in a pyrex reactor (capacity approx. 400 ml, see
All hydroperoxide concentrations were deter- Fig. 1). The dispersion of the oxygen in the
mined by an iodometric method [8]. This method liquid was effected with a nozzle and a stirrer.
Table 1. The oxygen was of commercial quality con-
Acctmcy of the analysis o/ cumene hydropemride taining at least 99 per cent 0s. When air was
used as the oxidant it was first filtered through
Found by cotton wool.
analyak Mean Dzvia-
tion PURITY OF THE FEED
% wt Technical cumene absorbed only a very small
L-__
amount of oxygen at 120°C in the pyrex reactor.
19.5 19.6 19.6 - 04
48.1 48.2 - 1.8 No hydroperoxide could be detected in the
95.8 95.7 95.8 - 4.2 reaction mixture.
Rectification of the technical products yielded
a cumene fraction, boiling range
152-O-152@C, nz 1.4918 (lit.b.p.
152.8’C, ng 1.4918 [S]). This
fraction, however, still refused
to absorb an appreciable amount
of oxygen at 12O’C within six
hours. It was suspected that
the cumene contained inhibitors
which had not been removed by
distillation.
Chemical treatments to im-
prove the oxidizability of cumene
are described in the literature,
i.e. boiling with sodium [2],
washing with bisulphite or per-
manganate solutions [S] or
with sodium hydroxide [s].
Several methods have been
tested. For this purpose the
Fig. 1. The pyres reactor. crude cumene was first distilled,

188
 J. P. FOXTWIN
and H. I. WATERMAN: Production of phenol from cumene
the fraction boiling between lbl-156°C being sub-
jected to several treatments. The treated cumene
was then dried over calcium chloride, distilled
again and the fraction with $ 1.4918 oxidized
in the pyrex reactor.
Pig. 2. Purification of cumene.
The .foUowing treatments were applied :
1. Permmganate treatment.
250 ml cumene was agitated for 10 mins with
200 ml 8 per cent aqueous KMnO, solution, then
washed with 2 n caustic soda solution and with
water.
2. Bkulphite treatm+mt.
250 ml was twice agitated for 10 mins with 100 ml
of a 5 per cent aqueous solution of sodium bisul-
phite solution, then washed with water.
8. Hypochlorite treatment [lo].
500 ml cumene was agitated for 15 mins with
80mltlnaceticacidand86Omlofanaqueous
hypochlorite solution which contained 225 grams
of bleaching powder, comprising 27.4 per cent wt
of active chlorine. After separation the treated
cumene layer was washed with water.
4. So&urn h~droside treatment.
500 ml cumene was twice agitated for 10 mins
with 20 ml of a 25 per cent aqueous solution d
NaOH and then twice with 100 ml water.
184
5. So&urn treatment.
500 ml cumene was boiled for 1 hour with 15
grams of sodium.
6. Sulphuric a&d treatment.
800 ml of cumene was thrice agitated for 10 mins
with 20 ml of sulphuric acid (96 per cent, spec. wt
l-84), then washed with water, 2 n sodium hydro-
xide solution and again with water.
7. Double sulphuric acid treatmmt.
800 ml of cumene was subjected to the same
treatment as described under 6 with the only
difference that the agitation with sulphuric acid
was repeated six times instead of three times.
Oxidation tests were carried out by bubbling
through oxygen gas at a rate of between 9 and
10 l/h. In each run 200 ml of cumene was used
to which 8-O per cent wt of cumene hydroperoxide
had been added as initiator. The temperature
during the oxidation was 120°C. The hydro-
peroxide content of the oxidized liquids was
determined at hourly intervals. The results of
treatments 1 and 2 were entirely negative, no
cumene hydroperoxide being formed in the
liquids. The results of the other tests are shown
in Fig. 2.
It is clear that the treatment with aoncentrated
sulphuric acid gave the most satisfactory results.
I.n some instances, however, a treatment with
ndphuric acid did not yet provide reproducible
oxidation rates. It was found that in those cases
the oxidixability could be restored if a second
purification step was added. After the double
5ulphuric acid treatment the cumene was then
agitated twice for 5 mins with a 5 per cent aqueous
solution of mercuric acetate followed by a caustic
soda and a water wash.
Technical cumene is prepared by catalytic
alkylation of benzene with propylene. Sulphuric
acid, phosphoric acid (on a carrier) or aluminium
chloride are generally used as catalysts. Con-
tamination of the crude cumene with thiophenes,
propylene polymers or styrenes is therefore very
likely. Which of the possible contaminants acted
as inhibitors was investigated by adding l/k mol
per cent of these substances to purified cumene
and measuring the oxidation rate of the liquids
 J. P. FORITTIN
and I-l. I. WATEXMAN
: Productionof phenolfrom cumene

is raised. .llO”C seenIs the best reaction tem-

perature in this apparatus.
Some experiments were carried out with air as
the oxidant. Copper turnings or finely divided
silver were added as catalysts. The results are
given in Fig. 5.

Fig. 6. The copperreactor.

Fig. 5. Oxidationof cumcnewith air.
Eil?pdMti
Oxidation temperature 110°C; throughput of air
15 l/h. Stirrer speed 1,200r.p.m. 200-n-J batches
of cumene to which 54 per cent wt of cumene
hydroperoxide had been added as initiator.
About the same maximum oxidation rate is
observed with air as with oxygen at llO"C, which
indicates that the rate is independent of the
oxygen concentration.
Under these conditions the hydroperoxide
silver on pumice were added. These catalysts
were prepared by adsorption of the complex
ammonia compounds of the metals on pumice,
followed by reduction with hydrogen [Xl].
Batches
of 250 ml of purified cumene were used in the
experiments, which were carried out at 12O’C
with an oxidation period of 8 hours.
Table 8.
Expm*menia in ths copper reactor (wiihoui BLirrer).
Ctmcnc hydro-

I
19eroaSdeconcentra-
formation is catalysed by the metals. oxldan: l/h Ciddpt so?3

EXPERIMENTS IN A COPPER REACTOR

Addition of copper bronze during the oxidation
of cumene exerts a catalytic effect. It was
found, moreover, that cumene hydroperoxide
shows a marked stability in copper compared
with glass or iron at 110°C[12].Therefore, the
preparation of cumene hydroperoxide was now
studied using a copper vessel as the reactor. The
reactor employed is shown in Fig. 6. The content
of the vessel was approx. 850 ml.
Before each experiment the inner surface of
the reactor was rinsed with fuming nitric acid
(spec. gr. 1.52) then washed with water and
dried.
No stirrer was applied in the first experiments.
To increase the active surface area copper or
_-
air
air
air
oxygen
The addition of metallic catalysts is of no value
here. It was noted, however, that with the silver
catalyst added the resulting peroxide solution
was nearly water-white, whilst the other oxidized
liquids were uniformly yellow coloured.
As no stirring is applied the oxygen pressure
influences the oxidation rate here, the rate-
determining step being the diffusion of oxygen
into the liquid.

186
 J. P, FORTUIN
and PI. I. WATERMAN
: Pro~uction~of’phenolfrom cumene
,
In the next series of experiments a copper Friedel Crafts type catalysts [IS] and sulphur
stirrer was used, (as can be seen in Fig. 6, stirred or phosphorus [17].
speed 880 r.p.m.) 225 ml of purified cumene was In our investigation sulphur dioxide was used
oxidized in each run with oxygen, introduced at as the catalyst. High yields of phenol and acetone
a rate of 25 l/h. No initiator was added, as it were obtained from the cumene hydroperoxide.
was observed that the oxidation in the copper Later it appeared that a patent application had
reactor proceeded without an induction period. been filed for the use of sulphur dioxide as a
The results are given in Table 4. catalyst. in this reaction [18]. It was also men-
tioned by KHARASCH[IS].
Table 4
Eqwrimtnk in ihe copper Tea&r Experimental
When SO, gas is fed into a flask containing some
TtWl- Ozidaiion Final Total
grams of pure cumene hydroperoxide the liquid
perature period hydropero- oiqgen Yield
“c! h tide cone. in liquid explodes almost immediately. The reaction
%
% wt % wt proves to be strongly exothermic.
Even at very low temperatures sulphur dioxide
120 1 11.0 2.45 95 is still active. When cumene hydroperoxide was
120 2 22.5 6.08 98
added dropwise to liquid SO? which was kept at a
120 a a4.7 1.54 96
180 1 25.0 660 81 temperature of - 55’C, there was again a heavy
la0 2 84.4 - - explosion after some time. We assume that the
reaction set in after a given quantity of hydro-
peroxide had accumulated in the liquid sulphur
High yields were obtained at 12O”C, which dioxide and ended in an explosion as the result
seems to be the best oxidation temperature in of insufficient heat removal.
this apparatus. The reproducibility of these Temperature control is of particular importance
results was good. Generally 11-18 per cent wt of here, for the hydroperoxide will decompose to an
cumene hydroperoxide was formed per hour on increasing extent according to an alternative
oxidation at 12O”C, when cumene of high purity reaction when the temperature is raised. As is
was used. These rates are considerably higher known, the main products formed during thermal
than those mentioned in the literature for cumene decomposition are acetophenone and methyl
oxidation. alcohol. It is obvious therefore that, if during
the catalytic decomposition the temperature is
DECOMPOSITION OF CUMENE HYDROPEROXIDE not sufficiently controlled, the yield of phenol
HOCK and LANG heated cumene hydroperoxide and acetone will decrease.
with a large excess of 10 per cent sulphuric acid To avoid the danger of explosion due to the
for 14 hours at 100°C. A 75 per cent yield of great activity of sulphur dioxide, the reaction
phenol was obtained, the presence of acetone had to be restrained. This was achieved by
being qualitatively demonstrated [2]. dropping cumene hydroperoxide into an atmos-
This reaction was studied afterwards by phere of sulphur dioxide gas. Preference was
KHARASCH and collaborators [IS]. Under the given to a method in which the liquid flowed in
catalytic influenceof acids(as conceived by LEWIS) a film over a cooled surface and the catalyst
almost exclusively phenol and acetone were could be absorbed by the liquid.
obtained from cumene hydroperoxide. According The assembly is shown in Fig. 7.
to these investigators the cleavage of the hydro- Sulphur dioxide gas, dried by passing it through
peroxide proceeded as a chain reaction through a wash bottle with concentrated sulphuric acid,
an ionic mechanism. was run via a capillary flow meter into a vertical
The patent literature discloses the use of glass tube with an inside diameter of 2 cm. At
sulphuric acid [15], acidic condensation - or the top of the tube cumene hydroperoxide was

187
 J. P. FOBTUWand H. I. WA- : Production of phenol from cumene

added dropwise from a dropping funnel, so that mixtures of experiments carried out by the above
the liquid flowed down the wall in a thin layer. method gave the results collected in Table 5.
The outside of the tube wail was cooled by means
of water, kept at 10°C. The reaction mixture Tab& 5
was collected in a flask placed in ice under the Decompositbn of cumene hydropcmirkk b aulphur dbide.
tube.
cwnene Time of ITida of Yield oj
hgdroperwide addition in acetone phenol
add&ding min. % %

20-O 58 56-4 67.8

20-o 120 57-8 82.5
20.75 110 67.2 0243

SuIphur dioxide was passed through at the rate

of 1) &es/hour. After expulsion of absorbed SO,
the iodide reaction on unconverted hydroperoxide
in the mixture gave a negative result. The mixture
was then neutralized by means of n-caustic potash
to the litmus end point and the acetone distilled
off till a temperature of QPC had been reached.
The acetone was collected in a measuring flask
which was made up to 1 litre after the distillation.
The acetone content in the aqueous liquid was
Fig. 7. Decompodtion of cumene hydro~tide by determined by the hydroxyiamine method [19].
means of sulphur dioxide
The distillation residue was placed in another
measuring flask and the phenol content in the
In thii apparatus 25 g cumene hydroperoxide liquid determined by bromatometric titration [2O].
was passed through in 78 minutes. The tube The yields of phenol and acetone in the experi-
was illled with sulphur dioxide gas which WIU ments with pure cumene hydroperoxide point
supplied during the reaction at the rate of 11 out that undesired side reactions take place.
litres per hour. Further mitigation of the reaction can be obtained
The reaction mixture from the flask was frac either by dih&i the sulphur dioxide with an
tionally distilled, the sulphur dioxide being inert gas, or by dissolving the cumene hydro-
expelled during the first stage of heating. The peroxide in an organic solvent.
mixture was then separated into the following Since cumene hydroperoxide is always obtained
fractions : as a solution in an excess of cumene, it would be
favourable from a technical point of view if the
I. 6-O g boiling below 80°C.
oxidized cumene could, without further operations,
II. 148 g boiling range 60-17O”C, mainly watu r
directly be decomposed into phenol and acetone.
III. 11.81 g boiling range 170-18PC.
We have therefore carried out a number of
IV. 5.65 g residue.
experiments in which pure cumene hydroperoxide
The first fraction consisted almost entirely o! was dissolved in cumene in various concentrations
acetone (68 per cent of the theoretical quantity) and the liquids were decomposed as described
the third mainly of phenol (70 per cent of the above by means of sulphur dioxide,
theoretical quantity). The residue was a biacli The SO, was again passed through at the rate
resinous material. of 1) litres/hour. The temperature of the cooling
Quantitative determinations of the reacti 1 water for the film reactor was 10°C.

188
 J. P. FORRTXN
and H. I. WATERDUN
: Productioti’of phenol from cumene

At the end of the experiments the bulk of the 2. a film reactor for the decomposition of
absorbed sulphur dioxide ‘was removed by gentle cumene hydroperoxide
heating. The reaction mixture was then neutral. 8. a section for the processing of the decompo-
ized with dilute alkali. On further heating the sition products.
acetone distilled over; this acetone was deter. Purified cumene was used as base material for
mined by the hydroxylamine method mentioned all the experiments.
before.
The residue was made alkaline by adding a Re 1. The oxiduth section-For the oxidation
fresh quantity of dilute alkali so as to be sure reaction we used at first a copper reaction vessel
that all the phenol had dissolved in the aqueous of about 1100ml capacity provided with a copper
layer. stirrer. The cumene and the oxidizing gas could
The cumene was now pipetted off ; the remain- be fed continuously at the bottom of the reactor,
ing aqueous layer placed in a measuring flask and while provisions had been made for circulation of
made up to 1 litre with distilled water. The the oxidized liquid.
phenol in this liquid was determined bromato- Batch experiments of only one or two hours
metrically as in the previous series of experiments. yielded very satisfactory results. In long-time or
A survey of the results of the decomposition of continuous experiments, however, the packing of
cumene hydroperoxide solutions in cumene by the stirrer and of the circulating pump caused
SO,, is given in Table 6. much trouble. The rate of oxidation decreased
rapidly as a result of contamination of the cumene
Table 6 by attacked packing material.
Decompo&an of txnwne h@vperw&ie rdtdiona by SO, Another apparatus was therefore designed
I I I I which had no moving parts, so that during the
concenlsation of Qnantitg Timcof Yield of Yield of oxidation the cumene was in contact only with
eumeneh&o- solution ‘addition phend copper.
peroxide in the added in in in in
aohtim y. wt min.
The reactor consisted of a vertical copper tube
8 % %
1,250 mm long and with an inside diameter of
28.7 84-96 80 98.8 24 mm. The tube was sealed at both ends by
40.1 29.95 50 88.7 means of flanges; copper rings were used as
42.2 2wO 90 90.0 packing material. By an electrically heated
50.0 28.98 22 81.0
jacket the tube could be heated to the desired
temperature. Cumene and the oxidizing gas
These figures show clearly that the yield is were fed at the bottom of the reactor, while the
increased by slow addition and lower concentra- oxidized liquid and the excess of gas were dis-
tions of cumene hydroperoxide. charged at the top. Before each test the inside
of the copper tube was etched with fuming nitric
C~NTINU~~~ PROCEDURE FOR THE acid.
PREPARATION OF PHENOL FROMCUMENE Oxidation experiments have been carried out
In order to be able to study the overall process in this reactor with oxygen and with air as the
an apparatus was developed for the continuous oxidizing gases ; in some cases the surface area
preparation of phenol and acetone from cumene was enlarged by filling the tube with copper
on a small scale. The procedure was based on turnings. The results were satisfactory in all
the results of the experiments discussed in the cases ; operating continuously no decrease in
foregoing chapters. oxidation rate was Observed during a run of
Il$ hours.
hbperhental The apparatus is very simple. This type of
The apparatus consisted of three sections : reactor presents possibilities for application on a
1. an oxidation section larger scale.

189
 J. 1’. FORWIN und H. I. WATERMAN : Production of phenol from cumcne

We now consider the process : The t.hermal effect of t,he decomposition

cumene + oxygen + cumene hydroperoxide
+ phenol + acetone.
For the heats of reaction we then find :
cumene + oxygen + cumene hydroperoxide
+ 27.7 kcal/mol(12479 - 12196 = 27.7)
cumene hydroperoxide + phenol + acetone
+ 60.4 kcal/mol(1219X3 - 762.2 - 427 = 60.4)
These values are relatively inaccurate, for they
have been determined as the small differences
reaction is more than twice as great as that of
the oxidation reaction.
TECHNICALPROCEDURE
The technical realization of the “ cumene process”
for the preparation of phenol and acetone
naturally requires more extensive laboratory
experiments and particularly pilot plant work
than has been described.

Fig. 8. Flow sheet of the cumene process.

between two or three large numbers. The errors However, on the basis of the results obtained
in the heats of combustion accumulate in the the following procedure, schematically repre-
values of the heats of reaction calculated by this sented in Fig. 8, can be given [28] :
method. Moreover, we have based our calculations
on the assumption that the conversions take place a. Purification of the base material
quantitatively. The base material cumene, to be suitable for
When we leave these inaccuracies out of con- oxidation, should meet certain requirements. The
sideration, however, the following rough data for purification method t,o be adopted depends on
the design of technical equipment are available : the impurities to be removed from the crude
1. During the oxidation of cumene to cumene cumene. Air, oxygen, or, if necessary, another
hydroperoxide 27.7 kcal is liberated per g mol oxygen-containing gas mixture can be used as
cumene hydroperoxide formed ; this is 182 kcal the oxidant.
per kg cumene hydroperoxide formed.
2. During the decomposition of cumene hydro- b. The oxidation
peroxide into phenol and acetone 60.4 kcal is A number of long copper tubes can be used as
liberated per g mol cumene hydroperoxide con- reactors. At the bottom pure cumene and the
verted ; this is 400 kcal per kg cumene hydro- oxidizing gas are fed continuously. The reaction
peroxide converted. temperature is preferably 120°C.

191
 J. P. FOETUXNand II. I. WATERMAN I Production of phenol from cumene

At the top of the reactor the oxidized cumene Ir. J. J. VER~TAPPEN for doing part of the
is discharged. experimental work. Thanks are due to the
management of Koninklt!jke/SkeU-Laboratorium,
c. The decomposition
Amaterdum and N.V. De Batqfscke Petroleum
From a buffer vessel the hydroperoxide solution itidckapj, The Hague, for their permission
is fed to a number of Aim reactors in which the to publish this paper.
decomposition takes place under the influence of
SO, as a catalyst. REPE~ENCES
d. Processing ,of tke [l] Chem. Eng. Newa 1950 28 866!$ Petroleum Tie8 1951
65 1174. [2] Hock, II. and I, S.; Eer. lB44 77 B 257.
After the decomposition the liquid is first slightly
[S] Br .P . 610,2B8. [4] Br. P. 680,286. [S] Br. 8pp1.
heated so as to remove the bulk of the SO, 82604/48. [6]B&J. P. 501,871;Germ. 8ppl.A. 2620.
absorbed. This is followed by a treatment with [7]fhI'Il. 8p@. 5,150/51. [8]WAWEE, c. D., SMITE,
anhydrous soda till the liquid gives a neutral Il. II. and PETERS, E. D.; Anal. Chem. 1247 19 276.
[B] FRANCIS, A. W.; Chem.Revs. lB48 42 126.[lo] AXLDA~H,
reaction. After filtration the reaction mixture is
E. G. R. and BOWMAN, W. H.; J. Sot. Cheq. Ind. 1985 54
rectified. At a slightly elevated temperature the
267 T. (111SLSICHEB, E.; Ber. 1666 19 678. [12]To be
acetone distils over first ; from the remaining published. [la] Br. P. 587,584. [14] KEAMECH, M. S.,
liquid the unconverted cumene is distilled off in a FONO, A. and NUDZNBE~O, W.; J. Org. Chem. 1950 15
second column in vacuum. This cumene can be 748, 768. [la] Br. P. 626,085; 639,429. [IS] Br. appl.
82600-01/48. 1171 Eelg. P. SO7,BB8. [IS] Iklg. P. 4B7,SOB.
reused after purification.
[lo] MAIUSCO, M.; Ind. Eng. Chem. 1226 18 701. [20]
In a third column the phenol is separated from
RED~AN L. V., d OI.; J. Ind. Eng. Chem. 1918 S 889.
the residue. [al] See alao Br. P. 610,444. [22] Int. Crit. Tables Vol. V,
The authors wish to express their gratitude to 162 (1222).[28] See also Chem. Eng. 1951 58 11, 215.

CORRECTION -
We regret that in Vol. 2, No. 8 page 108, the
date of receipt of the paper by Dr. J. Anderson
Storrow was wrongly given. It should read
“ 7 July, 195%”

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