April 19, 1966 N.

FRAGEN 3,247,246
CYCLIC PROCESS FOR PRODUCTION OF TEREPHTHALIC ACID
Filed Nov. 6, 196l.

Aig. 2

INVENTOR.
Wathan Aragen
BY
-2-4-12
A77OAAWEY
United States Patent Office 3,247,246
Patented Apr. 19, 1966

1. 2
3.247,246 Both embodiments of the invention, as well as sug
CYCLIC PROCESS FOR PRODUCTION OF gested variations thereof, will be considered in the ensuing
TEREPHTHALCAC) discussion, which is to be read in conjunction with the
Nathan Fragen, Hammond, Ind., assignor to Standard attached drawings wherein:
Oil Company, Chicago, I., a corporation of Indiana
Filed Nov. 6, 1961, Ser. No. 50,338 FIGURE 1 is a schematic flow sheet showing an em
1. Clain. (C. 260-515) bodiment where the lower fatty acid is employed in sub
This invention relates to the preparation of terephthalic Stantial excess; and
acid. More particularly, it concerns the recovery of FIGURE 2 depicts an alternative to the FIGURE 1
terephthalic acid are produced by the so-called "Henkel process, in which the lower fatty acid is used in substan
process' for converting potassium salts of aromatic acids O tially stoichiometric amounts.
to dipotassium terephthalate. It will be appreciated that the drawings are intended to
Terephthalic acid, an intermediate widely used in the be schematic only, and that various auxiliaries, utilities,
preparation of polyester films and fibers, may be made duplicate and staged equipment, pumps, gages, etc., have
by various processes. Recently, the "Henkel process” has 15
been eliminated from the drawings for reasons of clarity
become of commercial interest. There are in fact two and simplicity. However, the need for and location of
“Henkel processes'; in one (Belgian Patents 522,849, 524,- these will be apparent to those skilled in the chemical
305, 547,301-2, U.S. Patent 2,863,913, U.S. 2,794,830, engineering arts in light of the present description.
etc.) the potassium salt of either benzoic acid, phthalic Turing first to FIGURE 1, an embodiment of the inven
acid, or isophthalic acid is disproportionated or isomerized 20
tion is schematically depicted which illustrates the pre
to dipotassium terephthalate, while in the other (Belgian ferred form of the invention. The basic items of equip
Patents 561,194, 576,528, etc. ) benzene is reacted with ment, in process sequence order, are Henkel process re
potassium carbonate in the presence of metal carbide actor 11, reaction product dissolving tank 12, terephthalic
“water-binding' agents to produce the dipotassium tereph acid Springing tank 13, centrifugal separator 14, benzoic
thalate. It is the former process with which the present in 25
acid dissolving tank 17, evaporator 18, and potassium
vention is primarily concerned. benzoate drier 19. For the process exemplified, benzoic
While the Henkel process has been responsible for acid is converted to potassium benzoate, while the lower
much interest and has resulted in the generation of many fatty acid employed is acetic acid. Other terephthalic
patents, commercialization has thus far been limited. This acid precursors, i.e. phthalic acid, phthalic anhydride, iso
appears to be the result of difficulties in Satisfying the 30
phthalic acid and benzene-the latter requiring some
economic requirement of recovering and reusing potas What different handling techniques-may be processed by
sium from the crude dipotassium terephthalate reaction the Same or an essentially similar procedure. Likewise the
product. In general, various acids are used for "spring other lower fatty acids, that is formic, propionic, and, less
ing free terephthalic acid from the reaction products, desirably the butyric acids, may be substituted for acetic
but in most cases the liberating acid has either been too 35
acid, with the essential equipment remaining the same
weak, causing incomplete potassium recovery, or exces although concentrations and process conditions will re
sively strong, making the liberating acid itself unrecover quire modification for optimum utilization of each acid.
able. The one exception, lower fatty acids, possess the Conversion of potassium benzoate, charged via line 21
proper strength, but have not heretofore been integrated to reactor 11, is accomplished according to the well
into an overall process. 40 known Henkel process as more fully is described in the
A cyclic process has now been discovered, according to introductory portion of this patent. Temperatures gen
the invention, employing lower fatty acids, for instance erally range between about 250° C. to about 400° C.
acetic acid, whereby outstanding recovery of both the ter (482–842. F.), but are said to be preferably above 350°
ephthalic acid and the potassium may be attained. More C., optimumly within the range of 400 to about 420° C.
over, the fatty acids may be recovered and recycled in a 45 The pressure within reactor is is preferably above 40
unique manner which is both simple and convenient. In atmospheres, this being chiefly artificially imposed car
addition, the inventive method also enables Henkel process bon dioxide pressure, while pressures of 200 and even
catalysts to be recovered and reused economically. 4,000 atmospheres are said to be useful. Catalyst, which
By virtue of the foregoing it has now been possible to are most suitably the metals zinc, cadmium, mercury,
provide an integrated cyclic Henkel process, and one which 50 lead, iron, or other heavy metals, and which may be em
is free of difficulties hitherto experienced. Thus, accord ployed either as the element or in oxide or in salt form,
ing to one embodiment, crude reaction products from a may also be employed, and it is a particular advantage
Henkel process are dissolved in water, treated with a fatty of the procedure described herein that such catalysts
acid to precipitate terephthalic acid which may thereupon may be recovered and reused without unduly complicat
be removed by physical means, and the resultant aqueous ing the operation. Catalyst concentrations are usually
solution of the potassium salt of the fatty acid may be within the range of about 1-5 weight percent on potas
reacted with benzoic acid or other terephthalic acid pre sium benzoate or other feed, and are preferably within
cursor to form a solution of the corresponding potassium the range of about 3-5 percent. Conversion times may
salt. This is then heated to distill off the fatty acid, and range from, say, 5 minutes to as much as 24 hours or
the remaining salt then fed to the Henkel process conver 60
even longer.
sion reactor. The cycle is then repeated. During the reaction, should there be any decarboxyla
In the foregoing embodiment, it is desirable to employ tion in addition to the desired disproportionation, excess
a substantial excess of lower fatty acid over the stoichi carbon dioxide may form. Also, when potassium ben
ometric requirements of the dipotassium terephthalate re zoate is employed as the feed, benzene forms as a co
action product. However, in an alternative embodiment, 65 product. If desired, these components may be vented
only substantially the stoichiometric amount of fatty acid through vent line 22, from whence benzene may be re
need be used, and for reasons which will be evident upon moved by scrubbing with, for example, high boiling
subsequent discussion, considerable additional equipment petroleum gas oil, which may then be stripped to liberate
savings may be realized. the benzene while unabsorbed carbon dioxide may be
 3,247,246
3 4
vented and/or recovered for reuse or for other purposes. this ratio should be substantially higher than stoichio
At the conclusion of a desired conversion reaction, metric, as for example greater than 2.5:1 and preferably
the original potassium benzoate feed has been converted at least about 3:1 or even more-up to 6:1 and possibly
to dipotassium terephthalate, with the concurrent pro even higher. A ratio of 4:1 of acetic acid to dipotassium
duction of a benzene co-product. The crude reaction mix terephthalate is used in the illustrative embodiment.
ture may then be transferred via line 23 to dissolving Temperature does not appear to be a significant variable
tank 12, where it is taken up in water. for the precipitation. Temperatures above about 20
In dissolving tank 12 the reaction products are dis C., and preferably within the range of about 60-100
solved in water, admitted via line 24. This water, in the C., offer some advantage with respect to minimizing the
embodiment shown, is free of any substantial amount amount of water which need be present.
of acid, so that no terephthalic acid is precipitated in dis Springing tank 13, which is equipped with a rotary
solving tank 12. It has been found that the optimum mixer for efficient agitation, is sized so as to afford a hold
temperature for dissolving tank 12 is the normal boiling ing time of about 5 minutes. At the end of this period,
temperature of the resultant solution; dipotassium ter the magma is transferred via line 31 to a physical Sepa
ephthalate dissolves in boiling water to the extent of rating means such as centrifugal separator 14. Here the
about 400 grams per liter of water, and its solubility terephthalic acid crystals are separated from the mother
at 26.1° C. (79F) is 288 grams per liter of water. Tem liquor, which at this stage is composed of water, excess
peratures other these may of course be employed, and the acetic acid, and potassium acetate. As an alternative or
tank may be maintained under pressure if desired to adjunct to centrifugal separator 14, other separating or
achieve even higher temperatures and concurrently great thickening systems may be employed, such as for exam
er solubility. ple, hydrocyclones, Dorr thickeners, filters, etc.
For economy of downstream operations, particularly The stream of terephthalic acid emitted from centrifu
with respect to distillation heat load, it is desirable to em gal separator 14 is wet with mother liquor. If desired, this
ploy as small amount of water as is possible, consistent stream may be washed with dilute acetic acid and/or Wa
with other factors such as purity of terephthalic acid ter for purification, and then dried and sent to product
precipitate. Secondly, although highly concentrated di storage via line 32.
potassium terephthalate solutions can be obtained, it The mother liquor discharged from centrifugal sepa
appears that solutions ranging from about 5 to about 15 rator 4 is conducted via line 33 to dissolving tank 17,
percent salt content are optimum in all regards, although where benzoic acid feed stock is admitted from source 6
this may be increased to as much as 50 percent or more 30 and line 34. In the agitated dissolving tank 17, benzoic
under particular economic conditions. In the present acid reacts with potassium acetate to form an equilibrium
illustrative embodiment, a boiling 10 percent potassium with potassium benzoate; this equilibrium is disrupted
terephthalate solution is produced. in evaporator 18 when acetic acid is removed by distilla
Adsorbent carbon, i.e. activated charcoal, may be in tion.
troduced via line 26 into dissolving tank 12 for the 35 The solution thus prepared in dissolving tank 17 is
purpose of treating the solution for removal of colored conducted via line 36 to the evaporator.
by-products. Usually less than about one percent by Evaporator 18 constitutes a portion of the system where
weight of absorbent carbon on dipotassium terephthalate in water and acetic acid are removed by distillation (the
need be employed. term is defined broadly to include evaporation, azeotropic
The solution from spring tank 12 is then transferred AO distillation with the aid of such azeotroping agents as
via line 27 to a physical separator such as filter 28, where methyl ethyl ketone or benzene) and where the resultant
the carbon and insoluble catalyst, e.g. cadmium ter potassium benzoate is dried in preparation for its being
ephthalate, are separated, and are processed in a manner charged to the Henkel process reactor 11.
to be discussed presently. From filter 28 the decolorized Evaporator 18 may be a single or multiple stage evapo
stream is passed via line 29 to springing tank 13. 45 rator, where water and acetic acid (liberated in dissolving
As a result of considerable research, it has been found tank 17) are taken overhead via line 36 and passed to
that the conditions for optimum precipitation of ter drying column 37. In turn, this column 37 separates wa
ephthalic acid by reaction between aqueous dipotassium ter as an overhead through line 24, and concentrates or
terephthalate and aqueous lower fatty acid are quite im dehydrates the acetic acid as a bottom product taken
portant, although they may be varied over wide ranges 50 through line 39. The water overhead from this distilla
with more or less equally satisfactory results. It has, tion column 37 passes via line 24 to dissolving tank 12
for example, been found that, in a batch operation, it is as a recycle stream, while the concentrated or dehydrated
preferable to add the dipotassium terephthalate to the acetic acid is conducted via line 39 to line 4 and thence
acetic acid rather than vice versa, and in either a con to springing tank 13.
tinuous or a batch operation it is highly desirable to 55 To assure complete dehydration and as complete as pos
insure adequate mixing. . sible acetic acid removal from the potassium benzoate,
Furthermore, the concentration of acetic acid, together potassium benzoate (or potassium benzoate slurry or so
with the ratio of acetic acid to dipotassium terephthalate, lution) from evaporator 8 is conducted via line 42 to
are important variables. For example, as may be seen drier 19. Here the potassium benzoate is heated, advan
from the examples presented hereinafter, both the re 60 tageously in the presence of a hot gas stream, to, say,
covery and purity of terephthalic acid are superior when 80-200 C. or higher in order to liberate any retained
the initial dipotassium terephthalate solution is rather acetic acid and water. Off gases from drier 19 are passed
low, e.g. 1.8 percent by weight, instead of a more concen through symbolic line 43 where they join line 41; in ac
trated 10 percent or so. However, 10 percent dipotas tuality, symbolic line 43 may include a cooler and/or
sium terephthalate solutions and even solutions with 65 Scrubbing tower where water and acetic acid are sepa
higher salt contents may be processed readily with attend rated from the gas and then transmitted to line 41.
ant savings in downstream distillation costs with a con It is desirable that the potassium benzoate leaving drier
centrated precipitant (acetic acid) solution, e.g. 20-80 9 have as little as possible of excess potassium or of
volume percent, and preferably about, say 50 volume per benzoic acid. This may require careful control of the
cent. In the preferred embodiment, a 10 percent dipotas 70 amount of benzoic acid introduced into dissolving tank
sium terephthalate solution is added to a 50 volume per 17 so as to avoid any excess. If precise control is im
cent aqueous acetic acid solution. possible or difficult, an excess of potassium is favored.
With respect to the molar ratio of acetic acid to dipotas - The dried potassium benzoate discharged from drier 19
sium terephthalate, it has been found that the stoichiomet is then cycled via line 21 to reactor 11 where, in the pres
ric 2:1 ratio is generally adequate, but for preferred results 75 ence of an appropriate catalyst Such as cadmium acetate,
 8,247,246
5 6
it is disproportionated through the Henkel process to di Referring spectifically to FIGURE 2, Henkel process
potassium terephthalate and benzene. Thus the entire reactor 1 is discharged via line 23 into springing tank
process can be made cyclic, and even continuous. It is 13, where the reaction mixture is combined with aqueous
also apparaent that the inventive process is exceedingly acetic acid from line 41. Acid concentration is advan
flexible, and many process conditions can be varied with 5 tageously within the range of about 1-20 volume percent,
in wide ranges to accommodate different external condi and contact temperatures are advantageously 60-100° C.
tions and product quality requirements. Also, in contrast The resultant mixture, which comprises a slurry of
to such prior art potassium recovery procedures, e.g. em terephthalic acid and an aqueous solution of predomi
ploying benzoic acid as distinguished from the present nantly potassium acetate with some unconverted dipotas
lower fatty acids, substantially more concentrated acid 10 sium terephthalate, is passed via line 31 to the centrifugal
solutions may be employed, with the result that heat loads separator 4 for physical separation of terephthalic acid
of evaporator i8, drier 19, and distillation column 37 crystals (via line 32) from the mother liquor. As de
may be kept quite low. scribed in conjunction with FIGURE 1, these wettereph
An additional and highly desirable modification of the thalic crystals may be washed with dilute acetic acid
inventive procedure is the inclusion of facilities for re and/or water for additional solution recovery and
covering and reusing Henkel process catalysts such as cad terephthalic acid product purification.
mium acetate. Again inviting attention to FIGURE 1, An additional feature of the FIGURE 2 embodiment
insoluble cadmium terephthalate is separated from line 27 is that it is unnecessary to provide separate catalyst re
by filter 28, along with adsorbent carbon and any insolu covery and recycle facilities. The catalyst dissolves in
be reaction by-products. The solid material so separated 20 the dilute acetic acid solution of springing tank 13 and
is transferred via line 44 to a dissoiving tank 46, where passes along with the balance of the solution through
it is intimately contacted with a dilute acetic acid Solu centrifuge 44 and ultimately is cycled via line 21 to the
tion. A portion of the solution flowing through line 41 reactor.
is excellent for this purpose, and may be introduced via Inasmuch as there is no need to provide a pure water
conduit 47. Acetic acid reacts with cadmium tereph 25stream, it is also possible with this embodiment to mate
thalate to form soluble cadmium acetate and insoluble rialiy reduce the size of evaporator 18 and drier 19 by
terephthalic acid; terephthalic acid, adsorbent carbon, and providing an optional evaporator 51 downstream of cen
reaction by-products are separated in filter 48 while the trifugal separator 4. This removes much of the excess
soluble cadmium acetate in aqueous solution is conducted water along with some of the acetic acid, and permits the
via line 49 to line 35 or to evaporator 8. By this pro 30 vaporized material to be transmitted to line 4 (prefer
cedure, cadmium acetate is dispersed in the potassium ably after cooling and condensation) via line 52.
benzoate which ultimately is to be cycled through line 2 The effluent from evaporator 5i is conducted via line
to the Henkel process reactor 11. The small amount of 53 to dissolving tank 17 where it is contacted with benzoic
terephthalic acid discharged from filter 48 may either be acid (or other acid precursor) obtained from storage
discarded or may be recovered by contact with a potas 26 and admitted to dissolving tank 17 via line 34. As
sium acetate solution. a consequence, an equilibrium solution or slurry is set
Substantial equipment savings over and above those up, with a chemical equilibrium existing between benzoic
attained with the process described in conjunction with acid, acetic acid, potassium benzoate, potassium acetate,
FIGURE 1 may be obtained by employing the process and dipotassium terephthalate. This equilibrium is dis
schematically shown in FIGURE 2, although there is 40 rupted when the effluent from dissolving tank 7 is trans
somewhat of a penalty in flexibility and throughput ca ferred via line 36 to evaporator 3, where volatile acetic
pacity. acid is taken overhead along with water.
Inviting attention to FIGURE 2, it may be seen that in further contrast to the system of FIGURE 1, the
identical items of equipment are assigned the same num process depicted in FIGURE 2 enables column 37 (FIG
bers as in FIGURE 1. URE 1) to be eliminated. Instead, acetic acid and water
Essentially, the FIGURE 2 embodiment differs from removed from evaporator 36 may be passed directly to
that of FIGURE 1 in that the Henkel process reactor 1. line 4i, with of course condensation means being pro
effluent is contacted directly with an acetic acid solution, vided. The discharged material from evaporator 18 is
preferably employing substantially stoichiometrically passed via line 42 to drier 19, which functions in a man
amounts (plus or minus about 10-20 percent) without ner analogous to that of drier 9 in FIGURE 1.
first taking up the reaction product in water. Since it is Drier 19 dries the mixture of potassium benzoate and
unnecessary to provide a separate water stream, water recycled dipotassium terephthalate to an extent which is
and/or acetic acid taken overhead from optional evap suitable for recycle via line 2 to Henkel process reactor
orator 5, evaporator 18, and drier i9 may be combined 1. Thus the process is made entire cyclic, and there is
directly in line 45 and recycled to springing tank 3. No 55 no reagent wastage. Consequently, only Small amounts,
acetic acid concentration need be employed. if any, of make-up potassium (e.g. KOH) and acetic
In both embodiments the chemical reactions are the acid need be added to the system.
same. Acetic acid reacts with dipotassium terephthalate It is apparent therefore that the FIGURE 2 embodi
to spring the trephthalic acid and form an aqueous potas ment enables a commercial plant to be built with even
sium acetate solution. This solution is thereafter reacted 60 lesser equipment costs than that of a plant constructed
with a precursor such as benzoic acid to form an equilib according to FIGURE 1. Moreover, because there is
rium solution or Suspension of benzoic acid, acetic acid, no need for separating water from aqueous acetic acid
potassium benzoate, and potassium acetate, and there solutions there is a substantially reduced heat load, with
after the equilibrium is disrupted when the volatile acetic attendant economies in utilities cost. Accordingly, it is
acid is distilled from the remaining potassium benzoate. 65 possible
This latter material may then be dried further and is plant builtto pursuant achieve even further savings by employing a
to FIGURE 2.
charged to the Henkel process reactor.
Physically, there are certain distinctions between the The following examples illustrate various embodiments
two processes. Because it is desirable to maintain the of the inventive process, with particular emphasis on the
solution in springing tank 13 substantially neutral (pH 70 step of effecting the reaction between the lower fatty acid
about 6-8) it is possible to use only the substantially and dipotassium terephthalate so as to favor the pre
stoichiometric quantity of acetic acid. As a consequence, cipitation of high purity terephthalic acid. These ex
some dipotassium terephthalate remains in solution and amples are intended to be illustrative only and are not
is cycled back to the recator 11 along with freshly pre to be considered wholly definitive or exclusive with re
pared potassium benzcate charge stock. spect to conditions or scope.
 3,247,246
7 8
EXAMPLES 1-6 EXAMPLES 23-26
These six examples illustrate the effect of acid strength In the following examples, a striking demonstration is
and of the proportion of acid to dipotassium terephthalate.made of the unusual difference interephthalic acid purity
In each instance, a 10 weight percent aqueous dipotassium when the dipotassium terephthalate solution is added to
terephthalate solution is added to an approximately 0.26 8 the acetic acid solution rather than vice versa. In each
normal aqueous solution of the precipitant acid. The of the four examples 50 volume percent aqueous acetic
following results are obtained. acid solution and a 10 weight percent dipotassium tere
phthalate solution is used. -

Table I-Effect of acid strength and excess of precipitant

10%. KTA added to approximately 0.26 N precipitant
Molar ratio, Percent TA Percent TA Percent Kin
Example Precipitant Pcpnt:KTA in ppt. recovered ppt. (as
K2SO4)

EXAMPLES 7-18 Table IV-Effect of order of mixing

(50% AcOH and 10%. KTA
These examples demonstrate the effect of initial di Percent TA in ppt.
potassium terephthalate concentration on the purity and 25 Molar ratio,
recovery of terephthalic acid. In the following exam- Example AcOH:KTA
ples, it is demonstrated that higher terephthalic purity AdiA3H to AdSTA to
as well as higher recoveries are obtained when the initial ----
dipotassium terephthalate solution is 1.8 weight percent 23-24----- 2 4.
strength than when it is 10 percent. 30 25-26----- 4. 60 99--

Table II.-Effect of KTA concentration

50%. AcOH added to KTA)
1.8%. KTA 10%. KTA
Molar ratio,
Example AcOF:KTA.
Percent TA Percent TA Percent TA Percent TA
in ppt. Recovered in ppt. Recovered

0.8 13 8 3 3
1, 4-1.5 83 . 50 4. 5
2 99-- 75 4. 4.
3 99-- 92 2S 30
4-4.3 99-- 95 58 60
6 ---------------------------- 99 96

EXAMPLES 27-29
EXAMPLES 19-22 50 In these examples the relative independence of precipi
tation conditions is demonstrated.
These examples demonstrate the superiority of dilute Table V-Effect of precipitation temperature
acetic acid, e.g. 0.26 normal, over a more concentrated 50% AcOFI added to 10%. KTA
50 volume percent acetic acid solution for affecting pre- 55 Percent TA in ppt.
cipitation of terephthalic acid. However it should also Example Temperature, C.
be noted that exceptionally high recoveries are obtained 2AcO:1 KIA 4 AcOH:1 KTA
even with the more concentrated acetic acid when the
acid is present in large excess over the stoichiometric. 27-------- 25
60
4.
.2
60
54
90 3 60

Table III.-Effect of AcOH concentration

10%. KTA added to AcOH)
TA
Concentration Molar ratio, Percent K.
Example AcOE AcOB:KTA in ppt., as
Percent Percent K2SO
in ppt. recovered
} 2:1 99.8 75.6 --------------
3: 99.95 3. 6 0.020
}50% (vol.:vol.)....K. i: - . . ---------6.13
 3,247,246
O
From the foregoing discussion, examples, and flow (b) separating said lower fatty acid and water from
sheets it is manifest that there has been provided, in ac said potassium salt of an aromatic acid by distillation,
cordance with the invention, an outstanding process for (c) reacting said potassium salt of an aromatic acid
recovering potassium values and terephthalic acid from at a temperature within the range of about 250 to
dipotassium terephthalate, the initial product obtained via about 420° C. in the presence of a heavy metal
the Henkel process. By employing a lower fatty acid to catalyst to produce dipotassium terephthalate,
react with the dipotassium terephthalate, not only may (d) making an aqueous solution of said dipotassium
terephthalic acid be recovered in outstandingly high yields terephthalate,
but potassium can be recovered and reused virtually with (e) adding to the resulting dipotassium terephthalate
out any loss. Moreover, the process embodying the pres O solution said lower fatty acid recovered from step
ent invention enables the precipitant acid to be recycled, (b), thereby precipitating terephthalic acid and form
again without any substantial loss. Thus there has truly ing a solution of a potassium salt of a lower fatty
been provided an outstanding adjacent to the Henkel proc acid, and
ess, and one which overcomes many of its limitations. (f) cycling said solution of a potassium salt of a lower
Obviously, many alternatives, modifications, and varia fatty acid into the reaction of step (a).
tions of the disclosed process will be apparent to those
skilled in the art in light of the foregoing description. References Cited by the Examiner
Accordingly, it is intended to embrace all Such alterna UNITED STATES PATENTS
tives, modifications and variations as fall within the spirit 2,841,615 7/1958 Schutt et al. ------ 260-515 X
and broad scope of the appended claim. 2)
2,879,291 3/1959 Elliott ------------- 260-525
I claim:
A method of preparing terephthalic acid which com 2,904587 9/1959 Johnson et al. -------- 260-55
prises the following steps: 2,927,130 3/1960 Schutt ----------- 260-55 X
(a) reacting an aqueous solution of a potassium salt 2,930,813 3/1960 Schenk et al. -------- 260-515
of a lower fatty acid with a member selected from 25 2,965,674 12/1960 Prill et al. ---------- 260-515
the group consisting of benzoic acid, phthalic acid,
phthalic anhydride and isophthalic acid to produce CHARLES B. PARKER, LEON ZITVER, Examiners.
a potassium salt of an aromatic acid and a lower LORRAINE A. WEINBERGER, Primary Examiner.
fatty acid,