1,808,155.

Patented June 2, 1931

UNITED STATES PATENT OFFICE

HY'YM E. BUG, OF ROSELLE, NEW JERSEY, ASSIGNOR T0 STANDARD OIL DEVELOPMENT
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COMPANY, A CORPORATION OF DELAWARE

PROCESS OF MAKING ISOPROPYL ACETATE

No Drawing.

Application ?led November 24, 1926. Serial No. 150,625.

This invention relates to improvements in portion of the distilled ester, and a lower
the manufacture of isopropyl acetate by re layer composed mainly of water. The layers
acting isopropyl alcohol with acetic acid, in are separately withdrawn preferably con
the presence of a catalyst and at a distilling tinuously and slowly so as not to disturb the
temperature. The invention will be fully stratification. Any alcohol and ester in the
understood from the following description lower layer are recovered by fractionation
for use in the next batch. The ester layer is
of a preferred method.
_

ordinarily continuously removed for puri?

Commercial isopropyl alcohol and acetic

acid, preferably glacial acid, are Placed in a
still. The alcohol may contain about 10%
or so of water, and if prepared from petro

cation by washing with water or the like.

The number of washings and the amount of -

60

wash water will depend upon the desired

leum re?nery gases will usually have a few purity of the ester. The wash water may be
percent of tertiary butyl alcohol as its chief added to the water drawn off from the
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organic impurity. More dilute acid and

alcohol may be used, but the removal of the

Strati?cation vessel.

>

' It is sometimes desirable to return a por ~65

tion or all of the ester layer to the still for

larger volume of water retards the process.

It is best to have the acetic acid initially
present in 100 to 200% excess of the theoreti
cal amount required for. reaction with the
alcohol. A small amount of a catalyst for
the esteri?cation reaction, for example 0.2 to

redistillation. This should be done, for ex

ample, if. some difficulty has caused a low

percentage of ester in~the upper layer.

The washed ester, is redistilled, with or? 70
without ?rst neutralizing any traces of acid
0.3% by weight of sulfuric acid is preferably that may contaminate it. The charge is ?rst

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distilled with fractionationup to a tempera
The mixture is distilled and the vapors ture of about 80 C. The residue is substan
are recti?ed. The temperature of the ?nally tially water free and may be distilled over 75
recti?ed ,vapors should be kept ' at about with little or no fractionation to produce the

.
7 5.5 C. I have found that at this tempera ?nished ester.
The acetic acid in the still becomes progres
ture the highest percentage of ester distills
over in the form of a substantially constant sively more dilute because of the formation
boiling mixture. When tertiary butyl alco of water in the reaction. Only about half 80
hol'is present, it decomposes during the dis of this water comes over at the preferred tem
added to the charge in the still.

25

30

tillation. The decomposition products ap perature of distillation, 75.5 C. When the

35

pear to reduce the boiling temperature of the acid no longer reacts e?iciently, the distilla
constant-boiling mixture, and in such cir tion is stopped. It is usually not best to con
cumstances the temperature of distillation tinue after the acid is less than,v about 65%

85

strength.

may be allowed to go as low as about 70 C.

An 80% or better yield of ester may be

It should not exceed 76 C. under normal
pressure, as the yield of ester falls off rapidly obtained by continuing the operation for a
beyond that point. The ester forms the sufficient time. However, it is usually more
greater part of the distillate, which is com economical to stop when about a 65% yield

posed mostly of ester, alcohol, and water.

45

substantially constant.

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The distillate is condensed and collected in

a large container in which it strati?es, form

~50

is obtained, as this can be reached with a "

Very little acetic acid as such distills over at relatively brief period of o eration.
Any alcohol' and ester le t in the still may
the temperature stated. Fresh alcohol and
acid, preferably in the ratio of 2 parts of be distilled off and used in the next batch. 05'
alcohol to one of acid, are added continu The acetieacid solution in the still is con
ously to keep the volume of reaction mixture centrated for further use, or is otherwise
suitably disposed of.
I claim:

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1. Process of making isopropyl acetate,

ing an upper layer containing the greater comprising distilling a mixture containing 100

ascents

isopropyl alcohol, acetic acid and water,

rectifying the distilled vapors, holding the

.?nally recti?ed vapors at a tem erature'not

exceeding .76 (3., takin off an condensing

' I the ISOPIO yl acetate ormed from the re

action of ISOPIO yl alcohol and acetic acid,

together with su stances associated with the

isopro yI acetate, and separating the iso

prop

i0

2.

acetate.

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rocess according to claim 1 in which

the isopropyl acetate and associated sub

stances are taken off, the mixture is allowed

to stratify the layer containing a large pro

' " portion 0

isopropyl acetate is withdrawn

15 and the isopropyl acetate is puri?ed by wash

mg with water.

In testimony that I claim the foregoing as

. my invention, I a?ix my si
, >

vas

ature.

niwnzm E. BUG.