Europaisches Patentamt | | | | | 1 1| | | | | | | | | || || || | | | | | | | |

(19) J European Patent Office

Office europeen des brevets (11) EP 0 858 990 A1

(12) E U R O P E A N PATENT A P P L I C A T I O N

(43) Date of publication: (51) Int. CI.6: C07C 51/43, C07C 5 1 / 4 8 7 ,

19.08.1998 Bulletin 1998/34 C07C 6 3 / 2 6
(21) Application number: 98102704.8

(22) Date of filing: 17.02.1998

(84) Designated Contracting States: • Suzuki, Hiroshi,

AT BE CH DE DK ES Fl FR GB GR IE IT LI LU MC c/0 Mitsui Chemicals Inc.
NL PT SE Kuga-gun, Yamaguchi 740 (JP)
Designated Extension States: • Taniguchi, Norio,
AL LT LV MK RO SI c/o Mitsui Chemicals Inc.
Kuga-gun, Yamaguchi 740 (JP)
(30) Priority: 17.02.1997 JP 32375/97
(74) Representative:
(71) Applicant: Hansen, Bernd, Dr. Dipl.-Chem. et al
MITSUI CHEMICALS, INC. Hoffmann Eitle,
Tokyo (JP) Patent- und Rechtsanwalte,
Arabellastrasse 4
(72) Inventors: 81925 Munchen (DE)
• Takano, Toshinori,
c/o Mitsui Chemicals Inc.
Kuga-gun, Yamaguchi 740 (JP)

(54) Process for producing purified terephthalic acid

(57) A process for producing purified terephthalic

acid capable of controlling the transmittance of the puri-
fied terephthalic acid product promptly in a simple pro-
cedure without necessitating to alter the condition of the
oxidation of paraxylene to thereby permit a minute con-
trol of the process and to allow to obtain a purified
terephthalic acid product with a low and constant impu-
rity level within a certain range, which process com-
prises

hydrogenating a crude terephthalic acid resulting

from a liquid phase oxidation of paraxylene in a
hydrogenation reactor 6 in the presence of a hydro-
genation catalyst, followed by precipitation of the
crystals 8, a solid/liquid separation 11, re-slurrying
14 of the separated crystals in water and a further
solid/liquid separation 16, to obtain a purified
terephthalic acid; observing the transmittance of
the resulting purified terephthalic acid; and control-
ling the temperature of the washing water so as to
maintain the observed transmittance within a pre-
O determined range.
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 1 EP 0 858 990 A1 2

Description high purity. A purified terephthalic acid may contain

small amount of contaminants, such as paratoluic acid
FIELD OF THE INVENTION resulting from the reduction of 4-CBA, and others. The
amount of the contaminants can be assessed by
The present invention relates to a process for pro- s observing transmittance of the purified terephthalic acid
ducing a purified terephthalic acid (PTA) by hydrogenat- as a substitute parameter.
ing a crude terephthalic acid (CTA) obtained by liquid The amount of the impurities in the purified tereph-
phase oxidation of paraxylene. thalic acid may vary with the amount of the impurities in
the starting crude terephthalic acid to be treated by
DESCRIPTION OF THE RELATED TECHNIQUES 10 hydrogenation. It has heretofore been practised to
maintain the amount of impurities in the crude tereph-
On oxidizing paraxylene with a molecular oxygen- thalic acid within a certain range mainly by controlling
containing gas in liquid phase, a crude product of the condition in the process for the production of the
terephthalic acid is formed, which contains, as a main crude terephthalic acid, namely, by controlling the con-
impurity component, 4-carboxybenzaldehyde (abbrevi- 15 dition of oxidation of paraxylene.
ated hereinafter as 4-CBA), in addition to terephthalic However, a control of the impurity level in the crude
acid. It is necessary to purify such a crude terephthalic terephthalic acid by adjusting the oxidation condition
acid in using as a starting material for producing polyes- has a difficulty that a prompt response to the optimum
ter fiber, which require a purified terephthalic acid as a condition is not able due to a considerable time lag
starting material. 20 required for the actual appearance of influence on the
For producing a purified terephthalic acid, a proc- amount of impurities in the purified product, so that it is
ess is known in which a crude terephthalic acid is not adapted for a minute administration of the product
treated by hydrogenation in the presence of a hydrogen- quality.
ation catalyst (Cf., for example, Japanese Patent Kokai
Hei 4-66553 A). In this process, a purified terephthalic 25 SUMMARY OF THE INVENTION
acid is produced by reducing 4-CBA into paratoluic acid,
which is water-soluble, by hydrogenation and removing An object of the present invention is to provide a
it from terephthalic acid by, for example, solid/liquid sep- process for producing purified terephthalic acid which
aration after crystallization of terephthalic acid. can afford to control the transmittance of the purified
The above-mentioned treatment by hydrogenation 30 terephthalic acid product promptly by a simple proce-
is realized by arranging a fixed layer of a solid catalyst dure without altering the condition of oxidation of parax-
within a reactor and passing an aqueous solution of the ylene, whereby a minute control of production can be
crude terephthalic acid to the catalyst layer while sup- realized and a purified product of terephthalic acid hav-
plying hydrogen gas to the reactor. The 4-CBA existing ing a constant impurity level can be produced.
in the crude terephthalic acid is reduced thereby into 35 The process for producing purified terephthalic acid
paratoluic acid. When the reaction mixture is cooled, according to the present invention comprises hydrogen-
terephthalic acid crystals will precipitate, while most of ating a crude terephthalic acid obtained by a liquid
the impurities, such as paratoluic acid etc., remain dis- phase oxidation of paraxylene in the presence of a
solved in the mother liquor. By performing a solid/liquid hydrogenation catalyst, causing crystals of terephthalic
separation, a primary purified product of terephthalic 40 acid to precipitate out of the hydrogenation reaction liq-
acid crystals having some inclusion of mother liquor uor, separating the resulting crystals from the mother
adhered on the crystals is obtained, while most of the liquor, washing the separated crystals with water,
impurities are left dissolved in the separated mother liq- observing the transmittance of the resulting purified
uor. terephthalic acid and controlling the temperature of the
By washing out the rest of the impurities adhered 45 washing water so as to maintain the observed transmit-
on the crystals, a purified terephthalic acid is obtained. tance within a predetermined range.
A commonly employed washing technique consists in a
re-slurrying the crystals of the primary product in water, BRIEF DESCRIPTION OF THE DRAWINGS
in order to transfer the impurities adhered on the crys-
tals to the aqueous layer. By effecting a solid/liquid sep- so Fig. 1 shows a flow sheet of an embodiment of the
aration of the resulting slurry again, almost all the process for producing purified terephthalic acid accord-
impurities are retained in the liquid phase and a highly ing to the present invention.
purified terephthalic acid having scarce impurity content
is obtained. DETAILED DESCRIPTION OF THE DISCLOSURE
For such a purified terephthalic acid to be used as 55
the starting material for polyester fibers and so on, it is The crude terephthalic acid to be treated by hydro-
required to maintain a constant quality and, thus, a con- genation according to the present invention is that
stant impurity level, in addition to the requirement for obtained by a liquid phase oxidation of paraxylene.

2
 3 EP 0 858 990 A1 4

Such a crude product of terephthalic acid may, in gen- thereof, so long as it permits to arrange therein a cata-
eral, contain, as a principal impurity, 4-CBA in an lyst layer filled with a hydrogenation catalyst and allows
amount of about 0.1 - 0.4 % by weight. supply of hydrogen gas thereto to effect contact of the
The liquid phase oxidation of paraxylene is realized aqueous solution of terephthalic acid and hydrogen with
in a reaction solvent using an oxidation catalyst. As the 5 the catalyst.
solvent for the liquid phase oxydation of paraxylene, For the hydrogenation reactor, one which has a
there may be used, for example, a fatty acid, such as fixed layer of solid catalyst disposed therein, a supply
acetic acid, propionic acid, n-butyric acid, isobutyric line for supplying the aqueous terephthalic acid solution
acid, n-valeric acid, trimethylacetic acid or caproic acid, thereto, a discharge line for discharging the treated liq-
or a mixture of such an acid with water. Among them, a 10 uor therefrom and a feed line for feeding hydrogen gas
solvent of acetic acid or of acetic acid containing water thereto is preferable. While the aqueous solution of
is preferred, as described afterwards. terephthalic acid may be supplied so as to cause an
As the catalyst of liquid phase oxydation of paraxy- upflow in the reactor, it is preferable to arrange the
lene, there may generally be employed a heavy metal aqueous terephthalic acid solution supply line at the top
compound and/or a bromine-containing compound, 15 of the reactor and the treated liquor discharge line at the
wherein, as the former, a compound of nickel, cobalt, bottom thereof so as to cause a downf low of the aque-
iron, chromium, manganese or the like is enumerated ous solution in the reactor. Here, hydrogen gas feed line
and wherein both are employed as the element or as a may preferably be disposed at an upper portion of the
compound preferably in a form soluble in the reaction reactor so as to be introduced therein from above.
system. In a preferred mode of the catalyst, cobalt com- 20 While a hydrogenation catalyst conventionally
pound, manganese compound and bromine compound employed hitherfor can be used here, such as for exam-
are used. Cobalt compound may be used usually in an ple, palladium, ruthenium, rhodium, osmium, iridium,
amount of 10 - 10,000 ppm, preferably 100 - 3,000 ppm, platinum, platinum black, palladium black, iron and
calculated as cobalt, based on the weight of the reaction cobalt-nickel, there may be used favorably a solid cata-
solvent. The proportion of the manganese compound to 25 lyst, in which such a catalyst as above is supported on
the cobalt compound may be in the range of 0.001 - 2 as a carrier, preferably on an adsorptive carrier, such as
the atomic ratio of manganese to cobalt. The proportion activated carbon, so as to permit to buid up a fixed layer.
of the bromine compound to the cobalt compound may In a steady state, the hydrogenation treatment is
be in the range of 0.1 - 5 as the atomic ratio of bromine realized by first re-slurrying the crude terephthalic acid
to cobalt. 30 crystals in water at a concentration of 10 - 40 % by
The liquid phase oxidation of paraxylene is carried weight, preferably 24 - 30 % by weight, heating the
out using a molecular oxygen-containing gas. For such resulting aqueous slurry at a temperature of 230°C or
a molecular oxygen-containing gas, usually a gas com- higher, preferably 240 - 300°C, under a pressure of 1 -
posed of an oxygen gas diluted by an inert gas, such as 11 MPa, preferably 3 - 9 MPa (gauge), to dissolve the
the atmospheric air or oxygen-enriched air, may be 35 crude terephthalic acid crystals and, then, supplying the
used. The oxidation reaction is effected usually at a resulting aqueous solution of terephthalic acid to the
temperature in the range of 150 - 270 °C, preferably 170 hydrogenation reactor so as to pass it through the solid
- 220 °C , under a pressure at which the reaction mix- catalyst layer, while feeding hydrogen gas to the reactor
ture can be maintained in the liquid phase and usually in at a feed rate of at least 1.5 molar times, preferably at
the range of 0.5 - 4 MPa (gauge). The duration of the 40 least 2 molar times the 4-CBA present in the aqueous
oxidation reaction may usually be in the order of 20 - crude terephthalic acid solution. The hydrogenation is
180 minutes as the residence time in the reactor, though effected at a temperature of 230 °C or higher, preferably
variable in accordance with the size of the reactor and 255 - 300°C , under a pressure of 1 - 11 MPa, preferably
other parameters. The water content in the reaction sys- 3 - 9 MPa (gauge), at a hydrogen partial pressure in the
tem may usually be in the range of 3 - 30 % by weight, 45 order of at least 0.05 MPa, preferably 0.05 - 2 MPa.
preferably 5 - 15 % by weight. By the hydrogenation treatment, the 4-CBA present
According to the present invention, the crude in the crude terephthalic acid is reduced into paratoluic
terephthalic acid obtained from the liquid phase oxida- acid which is water-soluble at lower temperatures. Thus,
tion of paraxylene is subjected to a treatment by hydro- by cooling the hydrogenation treated liquor down to a
genation in a hydrogenation reactor in the presence of a so temperature of 300 °C or lower, preferably 100 - 280 °C,
hydrogenation catalyst. Here, the crude terephthalic only terephthalic acid crystals will be precipitated, so
acid separated from the mother liquor of the liquid that paratoluic acid can be separated from terephthalic
phase oxidation is re-slurried in water and the resulting acid crystals by effecting a solid/liquid separation. The
aqueous slurry is heated and pressurized to form an so-separated terephthalic acid crystals have inclusion
aqueous solution of terephthalic acid, which is intro- 55 of impurities of the rest of mother liquor adhered on the
duced into the hydrogenation reactor and is subjected crystals and, by washing out the impurities from the
to hydrogenation. For the hydrogenation reactor, there crystals, a purified terephthalic acid is obtained.
is no special limitation in the form and construction The washing of the resulting terephthalic acid crys-

3
 5 EP 0 858 990 A1 6

tals is effected with water (usually with pure water) to terephthalic acid product will be maintained within a cer-
remove the impurities adhered on the crystals. As a tain range.
concrete technique for the washing, generally a method By the technical measure of controlling the temper-
is employed in which the crystals of primarily purified ature of the washing water so as to maintain the trans-
terephthalic acid resulting from the solid/liquid separa- 5 mittance of the purified terephthalic acid product within
tion after the crystallization of terephthalic acid are re- a certain range according to the present invention, it
slurried in the washing water to transfer the impurities becomes possible to control the transmittance of the
adhered on the crystals to the liquid phase of washing purified terephthalic acid product promptly by a simple
water and subjecting the resulting aqueous slurry again procedure without altering the condition of oxidation of
to a solid/liquid separation, whereupon the separated w paraxylene, whereby a minute control can be realized
crystals are dried to obtain a purified terephthalic acid and a purified product of terephthalic acid having a con-
product having a low impurity level. stant impurity level can be produced.
For other washing techniques, there may be exem-
plified a method, in which a washing liquid is sprayed THE BEST MODE FOR EMBODYING THE INVEN-
onto a moving layer of the terephthalic acid crystals 15 TION
separated by a solid/liquid separation on a rotary filter or
a centrifuge so as to effect repeated re-slurrying and Below, the present invention will further be
solid/liquid separation, or a method, in which the reac- described by way of an embodiment with reference to
tion solvent is replaced with a washing water by bringing appended Fig. 1.
a moving layer of the terephthalic acid crystals sepa- 20 Fig. 1 shows a flow sheet of an embodiment of the
rated by a solid/liquid separation on a rotary filter or a process for producing purified terephthalic acid accord-
centrifuge into contact with the washing water in a coun- ing to the present invention. In Fig. 1, the numeral 1 rep-
ter flow, as disclosed in Japanese Patent Kokai Hei-7- resents a slurrying tank for slurrying the crystals of
149690 A. crude terephthalic acid (CTA) in water.
In employing either one of the above washing tech- 25 For producing a purified terephthalic acid product
niques, a purified terephthalic acid product is obtained by the embodiment of Fig. 1, an aqueous slurry of crude
by finally effecting a solid/liquid separation and drying, terephthalic acid (CTA) is first prepared by introducing
wherein the transmittance of the dried final purified CTA 2 and water 3 into the CTA slurrying tank 1 with agi-
terephthalic acid crystals is observed to ascertain the tation. The resulting aqueous slurry is heated and pres-
product quality by sampling it. The observation of the 30 surized to dissolve the crystals of CTA and the so-
transmittance is realized in general by dissolving the obtained aqueous solution 4 of terephthalic acid is sup-
sample crystals in an alkaline water and determining plied together with hydrogen gas 5 to the hydrogenation
the transmittance of the solution on a spectrophotome- reactor 6, in order to subject the aqueous solution to a
ter at a wave length of 340 nm or 400 nm. treatment by hydrogenation. The resulting reaction liq-
According to the present invention, the temperature 35 uor 7 is cooled with relieving of the pressure, before it is
of the washing water is controlled so as to maintain the transferred to a crystallization tank 8 to cause precipita-
observed value of the transmittance within a certain tion of terephthalic acid crystals there.
range of, for example, 80 - 95 %, preferably 91 - 94 %. The slurry 9 of crystals formed in the crystallization
Here, the control of the temperature of the washing tank 8 is forwarded to a solid/liquid separation unit 10
water is effected in such a manner that the temperature 40 where the crystals are separated from the aqueous
of the washing water will be lowered by a voluntary phase which is discharged out as waste liquor 11. In this
width, for example, 10°C, when the observed value of manner, the impurities, such as paratoluic acid and
the transmittance exceeds over the upper limit of a pre- color components, which are soluble in water can be
set range and will be elevated by a voluntary width, for removed from terephthalic acid crystals 12. The sepa-
example, 10°C, when it exceeds down the lower limit of 45 rated primarily purified terephthalic acid crystals 12 are
the preset range. then introduced into a TA re-slurrying tank 14 together
The concentration of the impurities on the crystal is with a washing water 13 (pure water) for re-slurrying
higher at a portion closer to the crystal surface and the therein. The resulting aqueous slurry 15 is introduced
amount of impurities eluted from the crystals will be into another solid/liquid separation unit 16 where the
greater as the temperature of the washing water is so purified terephthalic acid crystals are separated from
increased. Therefore, the amount of the impurities the liquid phase which is returned as a recovered water
eluted out of the adhered mother liquor on the crystals 3 back to the CTA slurrying tank 1. The separated crys-
into the washing water will be decreased by lowering the tals 17 are dried in a TA dryer 18 to obtain a purified
temperature of the washing water and, on the contrary, terephthalic acid (PTA) 19 as the final product.
the amount of the impurities eluted out of the crystals 55 During the above production procedure, a sample
into the washing water will be increased by elevating the 20 of PTA is taken out of the TA dryer 18 and is for-
temperature of the washing water, whereby the content warded to a transmittance observing unit 21 to deter-
of the impuirties (the color components) in the purified mine the transmittance 22 thereof, which is introduced

4
 7 EP 0 858 990 A1 8

into a processing/control unit 23. In the processing/con- y =a •x + b

trol unit 23, the observed value 22 of transmittance is
compared with a preset value and, if the observed value and therefore
22 exceeds over the upper limit of the preset value, it
puts out an output command signal 24 for lowering the 5 y = 0.02-x + 90 (1)
temperature of the washing water by a decrement of, for
example, 10 °C, to a washing water temperature control Thus, it is seen from the number of data (n) and the
unit 25 and, if the observed value 22 exceeds down the correlation coefficient (r) that there is a correlation
lower limit of the preset value, it puts out an output com- between the transmittance of PTA and the temperature
mand signal 24 for elevating the temperature of the w of washing water. Namely, there is a positive correlation
washing water by an increment of, for example, 10 °C, to that an increase in the one value results in an increase
the temperature control unit 25. in the other value.
The washing water temperature control unit 25 con- From this, it is seen that an elevation of the temper-
trols the temperature of the washing water 13 in accord- ature of washing water by an increment of 10°C will
ance with the command signal 24 and the washing is result in an increase of the PTA transmittance T-340 by
water of so-adjusted temperature is pumped into the TA an increment of 0.2 %.
re-slurrying tank 14. In this manner, the amount of the While the above equation may not always be appli-
impurities eluted out of the crystals 12 into the washing cable, since the observed values may eventually vary
water can be controlled, with the result of attainment of due to the observation conditions, accuracy may be
maintaining the level of transmittance and, thus, the 20 increased by incorporating periodical re-estimation.
content of impurities, especially of the color compo- While the above results are based on an automatic con-
nents, in the product PTA 19 within a certain range. trol, similar controlling may be possible for a manual
Now, the equation for the correlation between the operation. While the above controlling technique is
temperature of the washing water and the PTA transmit- explained in a washing procedure by re-slurrying and
tance employed in the device for computing the control- 25 solid/liquid separation, it is possible to employ a similar
ling temperature width in the processing/control unit 23 controlling technique also in other washing techniques
will be described. including spraying of washing water onto crystal layer
The correlation equation is established by a statisti- and a counter-flow contact of the washing water with the
cal method by taking the transmittance value, in %, of crystals.
the PTA 19 discharged out of the TA dryer 18 as a vari- 30 By controlling the temperature of the washing water
able y and the temperature of the washing water sup- for washing the terephthalic acid crystals in accordance
plied to the TA re-slurrying tank 14, in °C, as a variable with the transmittance of the product crystals after the
x, respectively, based on the actually observed values treatment by hydrogenation and crystallization, it is
of them. Here, the transmittance of PTA is represented made possible to control the transmittance of the PTA
by the value determined on a spectrophotometer using 35 product promptly by a simple procedure without neces-
an aqueous solution of 2N KOH containing 15 % by sitating alteration of the condition of oxidation of parax-
weight of PTA at a wave length of 340 nm (T-340) or 400 ylene, whereby a purified terephthalic acid having a low
nm (T-400). and constant level of impurity content can be produced.
In general, for regression analysis assuming y as Below, the present invention will further be
the objective variable and x as the explanatory variable, 40 described by way of Examples.
respectively, there are methods, for example, first-order
regression analysis, multiple-order regression analysis Example 1
and polynomial regression analysis. The accuracy of
the analysis will be higher, in general, as the number of 10 m3 of a palladium catalyst supported on an acti-
the order of regression analysis increases. Below, the 45 vated carbon were placed as the hydrogenation catalyst
result of an approximation using an equation by a first- in a hydrogenation reactor, whereto 60 t/hr of a crude
order regression, which is easy in the processing, for terephthalic acid slurry containing 25 % by weight of a
the relationship between the transmittance of PTA by, as crude terephthalic acid having a 4-CBA content of 0.36
an example, T-340, and the temperature is given. % by weight were supplied in order to carry out treat-
The regression coefficient (a) and the regression so ment by hydrogenation at a temperature of 280°C under
factor (b) determined by actual observations for the a partial pressure of hydrogen of 0.7 MPa, followed by a
transmittance of PTA and the temperature of the wash- crystallization of terephthalic acid at a temperature of
ing water were 0.02 and 90, respectively. Here, the 100 °C under a pressure of 0.1 MPa (gauge) with sub-
number of data (n) and the correlation coefficient (r) sequent solid/liquid separation of the resulting slurry of
were 12 and 0.96, respectively. 55 the crystals, whereupon the separated crystals were re-
Therefore, the correlation between the PTA trans- slurried in water so as to obtain a slurry of a concentra-
mittance y and the temperature of washing water x can tion of 30 % by weight, followed by a solid/liquid separa-
be represented by tion again with subsequent drying of the separated

5
 9 EP 0 858 990 A1 10

crystals to obtain a purified product of terephthalic acid. the reaction solvent with the washing water by
In this production system, the purified terephthalic acid bringing a moving layer of the crystals separated by
product was observed for its transmittance and the a solid/liquid separation into contact with the wash-
process was controlled in such a manner that the tem- ing water in a counter flow.
perature of the washing water was lowered by a decre- 5
ment of 10 °C on exceeding the tansmittance over a 5. A process as claimed in either one of Claims 1 to 4,
value of 93.5 % and was elevated by a temperature wherein the controlling of the temperature of the
increment of 10 °C on exceeding the transmittance washing water is realized in such a manner that the
down a value of 91 .5 %, whereby the T-340 was main- temperature of the washing water is lowered when
tained within the range of 91 - 94 °C. 10 the observed transmittance value exceeds over the
upper limit of a preset value and is elevated when
Comparative Example 1 the observed transmittance value exceeds down
the lower limit of the preset valve.
In the production system of Example 1, the proce-
dures were repeated except that the temperature of the 15 6. A process as claimed in either one of Claims 1 to 5,
washing water was maintained at a constant tempera- wherein the controlling of the temperature of the
ture of 100°C . It was found that the fluctuation of T-340 washing water is realized in such a manner that the
of the resulting purified terephthalic acid was in the transmittance at a wave length of 340 nm or 400 nm
range of 90 - 95 %. is maintained within the range of 80 - 95 %.
20
Claims

1. A process for producing purified terephthalic acid

comprising
25
hydrogenating a crude terephthalic acid
obtained by a liquid phase oxidation of paraxy-
lene in the presence of a hydrogenation cata-
lyst,
causing crystals of terephthalic acid to precipi- 30
tate out of the hydrogenation reaction liquor,
separating the resulting terephthalic acid crys-
tals from the mother liquor,
washing the separated crystals with water,
observing the transmittance of the resulting 35
purified terephthalic acid and
controlling the temperature of the washing
water so as to maintain the observed transmit-
tance within a predetermined range.
40
2. A process as claimed in Claim 1, wherein the wash-
ing of the separated crystals is realized by re-slurry-
ing the crystals separated by a solid/liquid
separation in the washing water to cause the impu-
rities adhered on the crystals to be eluted out into 45
the washing water and, then, separating the crys-
tals in the resulting slurry by a solid/liquid separa-
tion.

3. A process as claimed in Claim 1, wherein the wash- so

ing of the separated crystals is realized by spraying
the washing water onto a moving layer of the crys-
tals separated by a solid/liquid separation so as to
effect repeated re-slurrying and solid/liquid separa-
tion. 55

4. A process as claimed in Claim 1, wherein the wash-

ing of the separated crystals is realized by replacing

6
 EP 0 858 990 A1

CNI
o O
c— CD. PTA
ro c
4—1
E>
Cfl l- S amp I i n g
C <D
nj w TA dryer
h O co-
.CN)
CN
s/l separation unit
0) CD-
c
t/1 —
in o .00
m i_ CNJ
O <-> 4J
o c •-
i- o c
Q. o 3 V
LO
cm <r
CO *T
<D o
1 u.
■1— TA re-slurrying tank
CO4->
5 c
o
0) o .CNI
c Wa s h i n s
.c a +-> water 0) o
wE— s/l separation unit —
ro a) c wa
o (0 —

LO
CNI Crystalliz. tank -^00

c LO
<u
o
Hydrogenat. reactor -^~CD
J* (0
I 0)

CTA slurrying tank

•T-H
tin
Water

< 00
CNI
o

7
 EP 0 858 990 A1

European Patent Application Number

EUROPEAN SEARCH REPORT
Office EP 98 10 2704

DOCUMENTS CONSIDERED TO BE RELEVANT

Category Citation of document with indication, where appropriate, Relevant CLASSIFICATION OFTHE
of relevant passages to claim APPLICATION (lnt.CI.6)
EP 0 469 327 A (MITSUI PETROCHEMICAL IND) 1-6 C07C51/43
5 February 1992 C07C51/487
* page 2, line 45 - line 55 * C07C63/26
* page 3, line 11 - line 18 *
6 JP 04 066 553 A 2 March 1992

EP 0 265 137 A (MITSUI PETROCHEMICAL IND) 1-6

27 April 1988
* column 4, line 32 - line 53 *
* example 1 *

US 5 557 009 A (IZUMISAWA Y0SHIAKI ET AL) 1-6

17 September 1996
* column 1, line 52 - line 67 *
* column 4, line 21 - line 45 *
* examples 8,9 *

TECHNICAL FIELDS
SEARCHED (lnt.CI.6)
C07C

The present search report has been drawn up for all claims
Place ofsearch Date ofcompletion ofthe search Examiner
THE HAGUE 26 May 1998 Held, P
CATEGORYOFCITED DOCUMENTS T: theory or principle underlying the invention
E: earlier patent document, but published on, or
X: particularly relevant if taken alone after the filing date
Y: particularly relevant if combined with another □ : document cited in the application
document of the same category L: document cited for other reasons
A: technological background
O: non-written disclosure &: member of the same patent family, corresponding
P : intermediate document document