3,105,018

3 4.
rectification, removing a tetralone fraction as a heads
product and a naphthol fraction as a bottoms product, or at a pressure of from about 10 mm. of mercury to about
50 mm. of mercury. The bottoms from primary stripping
batch-wise, removing, successively, a tetralone-contain still 2, which contain mostly 1-naphthol and diethylene
ing cut, mid-cuts which can be recycled to the distilla glycol with some tetralone, are fed to secondary stripping
tion and a naphthol-containing cut.
Recovery of 1-naphthol and 1-tetralone from the tetra still 3, having at least 8 theoretical plates, wherein dieth
ylene glycol and any remaining 1-tetralone are removed
lone-free and naphthol-free fractions which result from overhead
the naphthol-tetralone-alcohol distillation can be accom mm. of mercury by distillation at pressures of from about 50
plished by any of several well known means, such as by to about atmospheric pressure. The
distillation or washing the fractions with a solvent for O semi-refined 1-naphthol removed from the bottom of
secondary stripping still 3 can be further purified by dis
the alcoholic separating agent.
Solvent washing can be accomplished with any inert tillation in naphthol refining still 4 as shown, or in some
solvent in which the alcoholic separating agent employed other manner, such as by a water wash. The overhead
in the process of this invention is soluble, and in which streams from both primary and secondary stripping stills
either the naphthol or tetralone are insoluble. It is pre 5 2 and 3, which contain diethylene glycol and 1-tetralone,
ferred that the solvent employed be relatively volatile are fed to mixing tank 6 and are there mixed with wa
and readily separated from the alcoholic entrainer by ter. Two liquid layers are formed in the mixing tank;
distillation. Applicable solvents are water and hydro the upper layer is a diethylene glycol-water solution and
carbons boiling from about 60° C. to about 100° C., the lower layer is substantially pure 1-tetralone. The di
such as n-hexane, isohexane, n-heptane, isoheptane, iso ethylene glycol-water layer is drawn off from mixing
octane and the like. Water is the preferred solvent, 20 tank 6 and fed to diethylene glycol recovery still 5 where
where it can be used, for economic reasons. in separation of water and diethylene glycol is effected.
Where tetralone cannot be separated from the alcoholic Diethylene glycol removed from the bottom of diethylene
separating agent by a solvent wash, as where the alcohol glycol recovery still 5 is recycled and mixed with the in
is immiscible with water, it is readily recovered by 25
coming naphthol-tetralone mixture. Make-up diethylene
adding sufficient boric acid to the tetralone-containing glycol from feed tank 1 is fed to primary stripping still
fraction to convert the alcohol to the borate ester. The 2 as needed. Water removed overhead from diethylene
tetralone can then be distilled off, employing conven glycol recovery still 5 is recycled to mixing tank 6 as
tional distillation procedures. The borates are readily needed.
hydrolized by water. Thus, the alcohol can be recovered 30
The following examples are illustrative.
by mixing the borate with water, whereby the boric acid Example 1 -
precipitates out on cooling and is removed from the A charge containing 350 parts by weight of a mixture
aqueous mixture by filtration. The alcohol-water phases containing 81.5 weight percent of 1-naphthol and 18.5
of the filtrate are then allowed to settle out and are
separated. weight percent of 1-tetralone, and 350 parts by weight of
In some cases decantation processes can be employed 35 lauryl alcohol was placed in the kettle of a still having 16
to recover tetralone or naphthol from the two product theoretical plates and was distilled at a pressure of 10
fractions resulting from the naphthol-tetralone separa mm. of mercury. A cut amounting to 313 parts by weight
tion. For example, when glycerol is the alcohol em was recovered at a head temperature of from 130 C. to
140° C. and contained 75 percent of the 1-tetralone
ployed, the tetralone-containing distillate forms two lay 40 charged
ers upon standing. The upper layer contains 1-tetralone, free of 1-naphthol. The tetralone could be re
and the lower layer contains glycerol. These two lay covered from this fraction by esterification of the alcohol
ers are easily separated to permit recovery of the 1-tetra with boric acid to form laurylborate, and then distilling off
lone as a product and glycerol which can be recycled the 1-tetralone. Mid-cuts were taken to a head tempera
to the process. 45 ture of 143° C. At that temperature a cut amqunting
The preferred method for the recovery of the 1-naph to 149 parts by weight was obtained that was free of 1
thol from the naphthol-alcohol fraction is by distillation, tetralone and contained 41 percent of the 1-naphthol
which can be performed in the same column employed charged. This cut was added to 680 parts by weight of
for the naphthol-tetralone separation or in a separate heptane and was cooled to 15 C., whereby crystals of
column. This distillation can be carried out at pres 50 pure 1-naphthol were precipitated. About 20 percent of
sures from about 5 mm. of mercury up to about atmos the naphthol in the cut was recovered in this manner in
pheric pressure. When diethylene glycol, dipropylene a purity of greater than 99%.
glycol or butanediol are employed as the separating Example 2
agents, it is preferred to conduct this distillation at pres A charge containing 200 parts by weight of a mixture
Sures of greater than about 50 mm. of mercury, because 55 containing 76 weight percent of 1-naphthol and 24 weight
when pressures of less than 50 mm. of mercury are em
ployed an incomplete separation of alcohol from naph percent of 1-tetralone and 200 parts by weight of 7-ethyl
thol results. Thus, the naphthol from this distillation having 2-methyl-4-undecanol was placed in the kettle of a still
may require washing with a solvent for the alcohol for 4 theoretical plates and was distilled at a pres
complete separation of said alcohol and 1-naphthol. In 60 tion,sure of 10 mm. of mercury. A tetralone-alcohol frac
some instances, however, such as when hexametriol, 1,3- containing about 62.5 percent of the tetralone
butanediol or glycerol are employed as separating agents, charged was obtained at head temperatures of from 130
pressures of 10 mm. of mercury or less are required to C. to about 140 C. A cut boiling at 145 to 146 C.
prevent decomposition of these alcohols. was then obtained and contained 78 percent of the
The drawing is a flow diagram illustrating a preferred naphthol charged. This cut was dissolved in three times
embodiment of the process of this invention, wherein 65 its own weight of commercial hexane and cooled to 20
diethylene glycol is employed as the separating agent. C. to separate the naphthol from the tetradecanol. About
With reference to the drawing, a constant boiling mix 52 percent of the naphthol charged was recovered as
ture of 1-naphthol and -1-tetralone (naphthol-tetralone crystals which melted at 93 to 95 C.
CBM) is combined with diethylene glycol from diethylene Example 3
glycol feed tank 1, in a weight ratio of diethylene glycol 70 A charge containing 350 parts by weight of a mixture
to 1-tetralone of from about 2:1 to about 5:1. The
naphthol-diethylene glycol-tetralone mixture is then fed containing 82.5 weight percent of 1-naphthol and 17.5
to primary stripping still 2, having at least 8 theoretical weight percent of 1-tetralone and 350 parts by weight of
1,4-butanediol was placed in the kettle of a still having
plates, wherein distillation of said mixture is conducted 75 17 theoretical plates and was distilled at a pressure of
 3,105,018 6
5 parts by weight of 1,2,6-hexanetriol was placed in the
10 mm. of mercury. Cuts obtained at head temperatures kettle of a still having 16- theoretical plates and distilla
of from 115 C. to 130° C. amounted to 331 parts by tion was started at a pressure of 10 mm. of mercury. A
weight and contained a mixture of 1,4-butanediol and 1 cut of 29 parts, containing mostly tetralone, was obtained
tetralone. This mixture was mixed with 550 parts by at a head temperature of from 123' C. to 142 C. Mid
weight of water and the resulting mixture was allowed cuts containing tetralone and naphthol were taken to
to settle. Two phases formed, one of which contained 150° C. A cut which contained 73 percent of the naph
an aqueous solution of 1,4-butanediol, and the other of thol charged to the still in a purity of about 90 per
which contained 87 percent of the tetralone charged, free cent was obtained at a head temperature of 150 C.
of 1-naphthol. A series of mid-cuts was then taken at O The 1,2,6-hexanetriol remaining in the still was boiled
head temperatures of from 130° C. to 146° C. The
head temperatures leveled off at 146 C., and a cut off at a pressure of 5 mm. of mercury.
amounting to 355 parts by weight was obtained at this Example 8
temperature that had a freezing point of 94 C., indicating A charge containing 275 parts by weight of a mixture
that it contained over 98 percent 1-naphthol. With credit containing 81 weight percent of 1-naphthol and 19
for column holdup, the purified naphthol amounted to weight percent of 1-tetralone and 275 parts by weight of
70 percent of the 1-naphthol charged. Residue that a primary decyl ether of ethylene glycol was placed in
formed was less than 2 percent of the charge. the kettle of a still having 16 theoretical plates, and was
Example 4 distilled at a pressure of 10 mm. of mercury. A cut,
A charge containing 350 parts by weight of a mixture 20 amounting
head
to 224 parts by weight, was obtained at a
temperature of 122 C. to 136 C. which contained
containing 82.5 weight percent of 1-naphthol and 17.5
weight percent of 1-tetralone and 350 parts by weight of substantially all of the tetralone charged. A cut boiling
at 147 C. amounted to 219 parts by weight, and con
1,3-butanediol was placed in the kettle of a still having tained 1-naphthol free of 1-tetralone. This fraction was
17 theoretical plates, and was distilled at a pressure of
10 mm. of mercury. A heads cut, amounting to 375 25 mixed with 600 parts by weight of heptane and cooled to
10 C., whereby crystals of 1-naphthol precipitated out.
parts by weight, was obtained at a head temperature of The crystals were recovered by filtration and dried.
102 C. to 110° C., from which 70 percent of the tetra Fifty-four percent of the 1-naphthol charged was recov
lone charged was recovered free of 1-naphthol by water
washing. Mid-cuts were then taken to a head tempera 30 ered in over 99 per cent purity in this manner.
ture of 146 C., at which temperature the head tempera Example 9
ture leveled off. The fraction recovered at this tempera A charge containing 200 parts by weight of a mixture
ture amounted to about 136 parts by weight and con containing 81 weight percent of 1-naphthol and 19 weight
tained about 47 percent of the 1-naphthol charged in a percent of 1-tetralone and 200 parts by weight of 3
purity of about 97.5 percent. Residue that formed 35 methoxy-1,2-propanediol was placed
amounted to about 5 percent of the weight of the initial still having six theoretical plates and indistilled the kettle of a
at a pres
charge. sure of 10 mm. of mercury. A cut amounting to 199
Example 5 parts by weight was obtained at a head temperature of
Two hundred parts by weight of a mixture containing from 105 C. to 110° C. and contained 58 per cent of
76 percent of naphthol and 24 percent of 1-tetralone 40 the 1-tetralone charged free of 1-naphthol. Several mid
were distilled with 200 parts by weight of 2-ethyl-1,3- cuts were taken to a head temperature of 146°C., at
hexanediol at 10 mm. of mercury pressure. Tetralone which temperature a cut amounting to 123 parts by
alcohol fractions, containing 60 percent of the tetralone weight containing 1-naphthol contaminated with methoxy
charged, were obtained at head temperatures up to 148 propanediol and a small amount of 1-tetralone was ob
C. A tails fraction boiling steadily at 148 C. was then 45 tained. The solid, impure naphthol was melted and
recovered, and was poured into ten times its weight of poured into 700 parts by weight of water, whereby crys
water, whereby naphthol crystals were precipitated from tals of 1-naphthol precipitated. The naphthol was re
the solution. The precipitated crystals, amounting to 65 covered in a yield of 61.5 per cent at a purity of 88.3
percent of the naphthol charged, melted at 83 to 89 C. percent.
Example 6 50 Example 10
A charge containing 300 parts by weight of a tetralone A charge containing 150 parts by weight of a mixture
naphthol constant-boiling mixture and 300 parts by containing 80 percent of 1-naphthol and 20 percent of
1-tetralone and 150 parts of diethylene glycol was placed
weight of glycerol was placed in the kettle of a still hav
ing 16 theoretical plates and distillation was carried out 55 in the kettle of a still having four theoretical plates. The
under 10 mm. of mercury pressure. The initial distillate distillation was performed at a pressure of 10 mm. of
mercury throughout. A cut obtained at a head tempera
was turbid in appearance and separated into two layers ture of 146 to 147 C. contained 30 percent of the 1-naph
upon standing; the upper layer was tetralone and the low thol charged, and was free of 1-tetralone. This cut was
er layer was glycerol. Sixty-four parts of tetralone (87 thoroughly
percent of the tetralone charged to the still) were ob 60 water. Themixed with ten times its own weight of cold
crystals that precipitated out were filtered
tained in two cuts. The first cut boiled at 125 to 130
C., and formed a tetralone layer of 35 parts and a glycerol and dried overnight. The dried crystals melted at 95
C. to 96° C., which corresponds with the melting point
layer of 5 parts. The second cut boiled at 130 to 140 of pure 1-naphthol.
C. and contained 29 parts by weight of the upper tetra
lone layer and 14 parts by weight of the lower glycerol 65 - Example, 11
layer. The distillate then cleared and a mid-cut con A charge containing 500 parts by weight of a mixture
taining tetralone and naphthol was taken to a head tem containing 80 percent of 1-naphthol and 20 percent of
perature of about 149 C. A cut boiling at 149 C. 1-tetralone and 375 parts by weight of dipropylene gly
was obtained which contained 76 percent of the naphthol col was placed in the kettle of a still of seventeen the
charged at a purity of 92 percent. Glycerol was re oretical plates. Distillation was begun under 10 mm.
covered from the still at a temperature of 166° C. at of mercury pressure. A 1-tetralone-dipropylene glycol
10 mm. pressure. - mixture was distilled off to a head temperature of 125°
Example 7 C., then mid-cuts were taken to a head temperature of
. A charge containing 300 parts by weight of a constant mercury 145 C. . The pressure was then increased to 25 mm. of
boiling mixture of 1-tetralone and 1-naphthol and 300 75 and a series of Small cuts was taken to a head
 3,105,018
7 8
temperature of about 168 C. The freezing point of the cent of the 1-tetralone charged to the still, free of 1-naph
distillate, primarily 1-naphthol, rose to 94 C., and then thol, was obtained at a head temperature of 117 to 125
fell off slightly. About 48 percent of the naphthol C. Subsequent cuts taken to 146° C. were found to
charged was obtained as a product having a freezing point contain nearly all of the remaining tetralone as well as
greater than 90° C.
Example 12 diethylene glycol and naphthol. The total distillate to
this point amounted to 483 parts. The head tempera
A charge containing 250 parts by weight of a mixture ture leveled off at 146 C., close to the boiling point of
containing 81.5 weight percent of 1-naphthol and 18.5 pure naphthol. Spot samples of the distillate were taken
weight percent of 1-tetralone and 250 parts by weight of for freezing point determination and the distillation was
thiodiethylene glycol was placed in the kettle of a still 0. continued according to the following log:
having six theoretical plates and was distilled at a pres
sure of 10 mm. of mercury. Cuts recovered at a head
temperature of from 133° C. to 150° C. amounted to BP., °C
Pressure,
mm. of
Parts
by
Kettle
Temp.,
F.P.,
? C.
51 parts by weight and contained 92 percent of the tetra 5 Hg Weight ? ?.
lone charged free of 1-naphthol. The remaining mate
rial, amounting to 440 parts by weight, was mixed with 146--------------------------- 10 49 166 79
2600 parts by weight of water whereby crystals of 1 162--------------------------- 20 144 87 a 91.
naphthol were precipitated. The crystals were recov
ered by filtration and drying. The yield was 41 percent 20 distilling The above fiask. cuts were combined and recharged to the
of the naphthol charged at a purity of 98 percent. The
balance of the 1-naphthol could be recovered from the 186--------------------------- 50 127 205 93
aqueous
ether.
thiodiglycol filtrate by extraction with isopropyl
Example 13 9 io????????”.
C. fell at first on raising the pressure, then rose and leveled off at
25
A charge containing 150 parts by weight of a mixture Further distillation at 100 mm. failed to increase the
containing 80 percent of 1-naphthol and 20 percent of freezing point due to the small amount of material re
1-tetralone and 150 parts by weight of diethylene glycol maining in the still. V
was placed in the kettle of a still having four theoretical 30
plates. The distillation was performed at a pressure of Example 16
10 mm. of mercury throughout. A tetralone-containing
fraction was obtained at head temperatures up to 145 C. A charge containing 450 parts by weight of commercial
About 85 percent of the naphthol charged was obtained 1-naphthol (freezing point=93.5 C.) was placed in the
as a cut boiling at 145 to 147 C. This cut was poured 35 kettle of a still having a column of seventeen theoretical
into five times its weight of cold water and crystals of plates and 50 parts by weight of diethylene glycol were
about 95 percent purity and amounting 73 percent of the added. Distillation was begun under a pressure of 100
naphthol charged were recovered. mm. of mercury. After removal of 138 parts of distillate,
a spot sample was taken which froze at 93.5 C. The
Example 14 40 balance of the distillate, amounting to 67 percent of the
naphthol charged, was then taken in one cut. This cut
A charge containing 883 parts by weight of a mixture
containing 78 weight percent of 1-naphthol and 22 weight froze at 94 C., indicating greater purity than the start
ing material. No diethylene glycol was found in the final
percent of 1-tetralone was placed in a distilling flask and cut by infrared examination. The kettle temperature dur
660 parts by weight of diethylene glycol were added. 45 ing the distillation of the principal cut was 225° C. This
The mixture was distilled at a pressure of 50 mm. of example demonstrates that if the kettle temperature is
mercury using a column packed with glass helices equiv high enough diethylene glycol can be completely sepa
alent to nine theoretical plates. A heads cut boiling at rated from 1-naphthol by distillation.
148 to 162° C. was obtained. This cut amounted to 762 I claim: . .
parts by weight and contained 155 parts by weight of 50 1. The process for the separation of a mixture con
1-tetralone along with most of the glycol charged to the sisting essentially of 1-tetralone and 1-naphthol which
distilling flask and contained no naphthol. Several mid comprises distilling said mixture together with an alcohol
cuts were then taken to a head temperature of 178 C., Selected from the group consisting of alcohols having
at which temperature a cut freezing at 93 C. was ob the formulae:
tained. Subsequent analysis showed this cut to contain 55
at least 98 percent 1-naphthol, with less than 2 percent
diethylene glycol and only a trace of 1-tetralone. The
amount recovered at 178° C., together with the column
holdup, amounted to 63 percent of the naphthol charged
to the still. Residue formation amounted to only 2 per 60
cent of the naphthol-tetralone mixture charged. On di
lution with an equal volume of water, the heads product
separated into two layers, one of which contained an iswherein an
n is an integer having a value of from 1 to 3; in
integer having a value of from about 12 to about
aqueous solution of the glycol. The other layer con 14 when n is 1, a value of from about 4 to about 8 when
i tained pure 1-tetralone. 65 n is 2, and a value of from about 3 to about 6 when n is
Example 15 3; Y is selected from the group consisting of oxygen and
sulfur; c is an integer having a value of from 2 to 3; z
A charge containing 500 parts by weight of a mixture is an integer having a value of from 2 to 3; y is an integer
containing 80 percent of 1-naphthol and 20 percent of 1 ishaving a value of from about 10 to about 12 when g
tetralone was placed in a distilling flask and 375 parts is 3;2, and and a value of from about 9 to about 12 when z
a is an integer having a value of from about 1
by weight of diethylene glycol were added. The flask to about 4, and obtaining a lower-boiling fraction con
was installed below a column having seventeen theoreti taining 1-tetralone substantially free of 1-naphthol and
cal plates and distillation was started at 10 mm. of mer a higher-boiling fraction containing 1-naphthol substan
cury pressure. A cut of 194 parts, containing 85 per tially free of 1-tetralone. -
 3,105,018
9
2. The process for the separation of a mixture con comprises and obtaining
distilling said mixture together with glycerol
a lower-boiling fraction containing 1-tetra
sisting essentially of 1-tetralone and 1-naphthol which lone substantially
comprises distilling said mixture together with an alcohol fraction containingfree1-naphthol of 1-naphthol and a higher-boiling
substantially free of 1
having the formula: tetralone.
12. The process for the separation of a mixture con
sisting essentially of 1-tetralone and 1-naphthol which
wherein n is an integer having a value of from 1 to 3 comprises distilling said mixture together with 1,2,6-
and n is an integer having a value of from about 12 to hexanetriol and obtaining a lower-boiling fraction con
about 14 when n is 1, a value of from about 4 to about 0 taining 1-tetralone substantially free of 1-naphthol and
a higher-boiling fraction containing 1-naphthol substan
8 when n is 2, and a value of from about 3 to about 6
when n is 3, and obtaining a lower-boiling fraction con tially free of 1-tetralone.
13. The process for separating a mixture consistin
??
taining 1-tetralone substantially free of 1-naphthol and a essentially of 1-tetralone and 1-naphthol which comprises
higher-boiling fraction containing 1-naphthol Substantially distilling said mixture together with an alcohol having
free of 1-tetralone. 5
3. The process for the separation of a mixture con the formula:
sisting essentially of 1-tetralone and 1-naphthol which Y(CH2OH)2
comprises distilling said mixture together with a mono wherein Y is selected from the group consisting of oxy
hydric aliphatic alcohol having from about 12 to about 14 gen and sulfur and x is an integer having a value of
carbon atoms and obtaining a lower-boiling fraction con 20 from 2 to 3, and obtaining a lower-boiling fraction con
taining 1-tetralone substantially free of 1-naphthol and taining 1-tetralone substantially free of 1-naphthol and
a higher-boiling fraction containing 1-naphthol Substan a higher-boiling fraction containing 1-naphthol Substan
tially free of 1-tetralone.
4. The process for the separation of a mixture con tially free of 1-tetralone.
14. The process for the separation of a mixture con
sisting essentially of 1-tetralone and 1-naphthol which 25 sisting essentially of 1-tetralone and 1-naphthol which
comprises distilling said mixtures together with lauryl comprises
alcohol and obtaining a lower-boiling fraction contain glycol anddistilling obtaining
said mixture together with diethylene
a lower-boiling fraction containing
ing 1-tetralone substantially free of 1-naphthol and a 1-tetralone substantially free of 1-naphthol and a higher
higher-boiling fraction containing 1-naphthol substan boiling fraction containing 1-naphthol substantially free
tially free of 1-tetralone. 30
5. The process for the separation of a mixture con of 1-tetralone.
sisting essentially of 1-tetralone and 1-naphthol which sisting 15. The process for the separation of a mixture con
comprises distilling said mixtures together with 7-ethyl-2- comprises essentially of 1-tetralone and 1-naphthol which
methyl-4-undecanol and obtaining a lower-boiling frac distilling said mixture together with dipropylene
tion containing 1-tetralone substantially free of 1-naphthol glycol and obtaining a lower-boiling fraction containing
and a higher-boiling fraction containing 1-naphthol Sub boiling 1-tetralone substantially free of 1-naphthol and a higher
stantially free of 1-tetralone. fraction containing 1-naphthol substantially free
6. The process for the separation of a mixture consist of 1-tetralone.
ing essentially of 1-tetralone and 1-naphthol which com 16. The process for the separation of a mixture con
prises distilling said mixtures together with a dihydric 40 sisting essentially of 1-tetralone and 1-naphthol which
aliphatic alcohol having from about 4 to about 8 carbon comprisesglycol distilling said mixture together with thiodi
atoms and obtaining a lower-boiling fraction containing ethylene and obtaining a lower-boiling fraction
1-tetralone substantially free of 1-naphthol and a higher acontaining 1-tetralone substantially free of 1-naphthol and
higher-boiling fraction containing 1-naphthol substan
boiling fraction containing 1-naphthol Substantially free
of 1-tetralone. 45 tially free of 1-tetralone.
7. The process for the separation of a mixture con 17. The process for separating a mixture consisting
sisting essentially of i-tetralone and 1-naphthol which essentially of 1-tetralone and 1-naphthol which comprises
comprises distilling said mixtures together with 1,3- distilling said mixture together with an alcohol having
butanediol and obtaining a lower-boiling fraction con the formula:
taining 1-tetralone and a higher-boiling fraction containing 50 CyHay-1-O-CH2OH.
1-naphthol substantially free of 1-tetralone.
8. The process for the separation of a mixture consist wherein z is an integer having a value of from 2 to 3
ing essentially of 1-tetralone and 1-naphthol which com and y is an integer having a value of from about 10 to
prises distiling said mixtures together with 1,4-butanediol about 12 when z is 2 and a value of from about 9 to
and obtaining a lower-boiling fraction containing 1-tetra 55 about 12 when z is 3, and obtaining a lower-boiling frac
lone substantially free of 1-naphthol and a higher-boiling tion containing 1-tetralone substantially free of 1-naphthol
fraction containing 1-naphthol substantially free of and a lower-boiling fraction containing 1-naphthol sub
1-tetralone. stantially free of 1-tetralone.
9. The process for the separation of a mixture con 18. The process for the separation of a mixture con
sisting essentially of 1-tetralone and 1-naphthol which 60 sisting essentially of 1-tetralone and 1-naphthol which
comprises distilling said mixtures together with 2-ethyl-1, comprises distilling said mixture together with decoxy
3-hexanediol and obtaining a lower-boiling fraction con ethanol and recovering a lower-boiling fraction contain
taining 1-tetralone substantially free of 1-naphthol and ing 1-tetralone substantially free of 1-naphthol and a
a higher-boiling fraction containing 1-naphthol substan
tially free of 1-tetralone. 65 higher-boiling fraction containing 1-naphthol substan
10. The process for the separation of a mixture con tially free of 1-tetralone.
sisting essentially of 1-tetralone and i-naphthol which 19. The process for separating a mixture consisting
essentially of 1-tetralone and 1-naphthol which comprises
comprises distilling said mixtures together with a trihy distilling
dric aliphatic alcohol having from about 3 to about 6 said mixture together with an alcohol having
carbon atoms and obtaining a lower-boiling fraction con 70 the formu?a:
taining 1-tetralone substantially free of 1-naphthol and a
higher-boiling fraction containing 1-naphthol Substan wherein a is an integer having a value of from about 1
tially free of 1-tetralone. to about 4 and obtaining a lower-boiling fraction con
11. The process for the separation of a mixture con 75 taining 1-tetralone substantially free of 1-naphthol and
sisting essentially of 1-tetralone and 1-naphthol which
 3,105,018
a higher-boiling fraction containing 1-naphthol substan 12
tially free of 1-tetralone. ? References Cited in the file of this patent
20. The process for the separation of a mixture con UNITED STATES PATENTS
sisting essentially of 1-tetralone and 1-naphthol which 1,717,009 Davis ----------------- June 11, 1929
comprises distilling said mixture together with 3-methoxy 5 2,436,864 Mar? .ohnSOn ------------------- ,2 1948
1,2-propanediol and recovering a lower-boiling fraction 2,462,103 Johnson --------------- Feb. 22, 1949
containing 1-tetralone substantially free of 1-naphthol 2,595,266 Johnson ---------------- May 6, 1952
and a higher-boiling fraction containing 1-naphthol sub 2,773,006 Carver et al. ------------ Dec. 4, 1956
stantially free of 1-tetralone. 2,776,936 Bondor et al. ------------- Jan. 8, 1957