WO2009064037A1 - Récupération de catalyseurs, d'acide benzoïque et d'acide aromatique - Google Patents
Récupération de catalyseurs, d'acide benzoïque et d'acide aromatique Download PDFInfo
- Publication number
- WO2009064037A1 WO2009064037A1 PCT/KR2008/000180 KR2008000180W WO2009064037A1 WO 2009064037 A1 WO2009064037 A1 WO 2009064037A1 KR 2008000180 W KR2008000180 W KR 2008000180W WO 2009064037 A1 WO2009064037 A1 WO 2009064037A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- benzoic acid
- filtration device
- water
- filtrate
- range
- Prior art date
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 115
- 239000005711 Benzoic acid Substances 0.000 title claims abstract description 51
- 235000010233 benzoic acid Nutrition 0.000 title claims abstract description 51
- 239000003054 catalyst Substances 0.000 title claims abstract description 36
- 238000011084 recovery Methods 0.000 title claims abstract description 17
- 238000001914 filtration Methods 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 159000000032 aromatic acids Chemical class 0.000 claims abstract description 25
- 239000000706 filtrate Substances 0.000 claims abstract description 24
- 239000002910 solid waste Substances 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 239000002002 slurry Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 15
- 239000002699 waste material Substances 0.000 claims description 7
- 239000011148 porous material Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 230000008016 vaporization Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract description 8
- 238000000638 solvent extraction Methods 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 10
- 230000007423 decrease Effects 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000011572 manganese Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004065 wastewater treatment Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- -1 bromide (Br) ions Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/04—Monocyclic monocarboxylic acids
- C07C63/06—Benzoic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/04—Monocyclic monocarboxylic acids
Definitions
- This invention relates to a process for recovering catalysts, benzoic acid and other aromatic acids from solid wastes generated in a manufacturing process of an aromatic carboxylic acid.
- the said solid wastes contain many useful chemicals such as catalysts for oxidation reactions (0.7-1.4%), benzoic acid (17-32%) and other aromatic acids (7-15%) .
- the recovered catalysts can be reused in the oxidation reaction process of aromatic acids.
- the benzoic acid may be used as raw materials for dye intermediates, preservatives, insecticides, pharmaceuticals and plasticizers .
- Recently, the demand of benzoic acid has been increasing more rapidly due to the T) development of new processes for phenols and caprolactam, using benzoic acid as raw materials.
- the other aromatic acids recovered can be recycled back to the manufacturing process of the same aromatic acids or used in the manufacturing process of polyol resins. Since there are no economical processes
- the solid wastes are presently sent to the wastewater treatment facilities, buried underground or burned in incinerators or boilers, causing environmental pollutions,
- U.S. Patent 4,910,175 teaches a method for recovering catalysts from said solid wastes by filtration and oxidation reaction, following precipitation of cobalt (Co) and manganese (Mn) catalysts by using oxalic acid and caustic soda.
- this process has several disadvantages such as: (1) bromine (Br) , benzoic acid and other aromatic acids can not be recovered; (2) the consumption of expensive oxalic acid is 5 high; (3) the reaction rate in the oxidation reactor of aromatic acids decreases due to introduction of the sodium ion which is a catalyst poison; and (4) the process is very complex, requiring high investment costs.
- ROK Patent 1991-0003973 provides a method for recovering
- ROK Patent 1998-0009219 provides a method of recovering and purifying gaseous benzoic acid by using a gasifier and activated carbon. But this process has a number of technical difficulties to be overcome for commercialization, such as the 0 difficulty of separating benzoic acid from water (about 60% in said wastes) in the gas phase, the regeneration problem of used activated carbons, and plugging problems of equipment and pipelines . [Disclosure] [Technical Problem]
- the present invention provides a process for the recovery of catalysts, benzoic acid and other aromatic acids from said l.
- ⁇ solid wastes which comprises the following steps: a) separating the slurry mixture of residual aromatic wastes and water or an aqueous acetic acid solution from an extractor (3) into the first filtrate, containing catalysts, and wet cake, containing benzoic acid and other aromatic acids, 0 by means of both a filtration device 1 (5) and a filtration device 2 (8) or by using a filtration device 2 (8) only; b) feeding said first filtrate to an evaporator (10) , vaporizing excess solvent to recover a concentrated catalyst solution, reslurrying said wet cake with water (15) and feeding the resulting slurry to a filtration device 3 (18) to separate solids from filtrate, wherein the solids are sent to a dissolver (21) ; c) dissolving benzoic acid in the dissolver (21) and 5 feeding the resulting
- solvent (2) in an extractor (3) to extract catalysts such as cobalt (Co), manganese (Mn) and bromide (Br) ions, which are used as catalysts for the oxidation reaction.
- catalysts such as cobalt (Co), manganese (Mn) and bromide (Br) ions, which are used as catalysts for the oxidation reaction.
- Preferred solvents (2) for the solvent extraction are water or an aqueous acetic acid solution. Desired ratios of the solvent
- W feed rate relative to the solid wastes rate to the extractor (3) are 1.0 to 4.0 for water and 1.5 to 4.5 for the aqueous acetic acid solution. If the feed ratio of the solvent with respect to the solid wastes exceeds 4.0 for water and 4.5 for the aqueous acetic acid solution, the vaporization time of the solvent and energy required in the evaporator (10) become excessive, resulting in the increased operating costs. If the ratios of solvents are lower than 1.0 for water and 1.5 for the aqueous acetic acid solution, the extraction efficiency of T) catalysts decreases.
- the extractor (3) is preferably operated at a temperature within the range of 25 to 6O 0 C and at an agitator speed of 30 to 105 rpm with the extraction time of 0.3 to 1.5 hr.
- IJ catalysts is sent to the evaporator (10) .
- the concentrated slurry is recycled back to the extractor (3) , while part of the concentrated slurry is fed through line 7 to a filtration device 2 (8) for separation of wet cake.
- Filtrate (9) of the filtration device 2 is sent to the evaporator (10) and the wet
- the feed rate of water (15) to the filtration device 2 (8) is preferably maintained at 1.0 to 3.0 times the wet cake rate for the high recovery rate and purity of benzoic acid.
- the effluent slurry of the extractor (3) is processed by a single-stage filtration device
- the effluent slurry is pumped to the filtration device 2(8), bypassing the filtration device 1(5) .
- Filtrate (9) containing catalysts is sent to the evaporator (10) and the wet cake is sent to the 55 holding tank 1(16) along with water (15) .
- the evaporator (10) is used to vaporize excess water in order to minimize the amount of water being recycled back to oxidation reactors along with the recovered catalysts, since
- K water decreases the oxidation rates of aromatic alkyl compounds.
- the concentrated catalysts solution (14) is recycled back to the oxidation reactors for reuse.
- the vaporized water is condensed in a condenser (11) and then sent to the wastewater treatment facility. The temperature of the
- IT) evaporator (10) is preferably maintained in the range of 90 to 12O 0 C by a heater (13) .
- the evaporator (10) can be used as a holding tank without using the heater (13) and the condenser (11) .
- the slurry from the holding tank 1(16) is pumped to the filtration device 3(18) to separate liquid and wet cake in a similar way as for the filtration device 2(8) .
- the filtrate from the filtration device 3(18) is recycled back to the extractor (3) through a pipeline (20) and the wet cake, reslurried with water, is sent to a dissolver (21) .
- the feed rate of water to the filtration device 3 (18) for reslurrying is preferably maintained at 2.5 to 6.0 times the wet cake rate. If the feed ratio of water to the solid cake is more than 6.0, both energy consumption and equipment sizes increase, resulting in unfavorable process economics. If the feed ratio of water is less than 2.5, both the purity of benzoic acid and the recovery yield of other aromatic acids will decrease due to a higher temperature of dissolver (21) required to dissolve all benzoic acid.
- the resulting slurry is pumped to the filtration device 4(24) to separate liquid and wet cake in a similar way as for the filtration device 2(8) .
- the filtrate (31) of the filtration device 4 mainly composed of benzoic acid, is sent to a crystallizer (32) and the wet cake is sent to a holding tank 2
- the content of the holding tank 2 (27) comprising of mainly aromatic acids (other than benzoic acid) and water, can be recycled back to the aromatic acid production process or used as a raw material for polyol resins.
- the temperature of the dissolver (21) is preferably maintained in the range of 70 to 120 0 C by a heater (22) . If the temperature of the dissolver is higher than 12O 0 C, the purity of benzoic acid and the recovery rate of other aromatic acids decrease. If the temperature is lower than 7O 0 C, the purity of benzoic acid increases, but the recovery rate of benzoic acid decreases.
- the aqueous benzoic acid solution fed to the ") crystallizer (32) is crystallized after cooling temperature to the range of 10 to 6O 0 C by using chilled water (33) and a cooler (34) . If the crystallizer temperature is higher than 60 0 C, the recovery yield of the benzoic acid becomes low since some dissolved benzoic acid cannot be crystallized.
- crystallizer temperature lower than 1O 0 C is not desirable, since both investment and operating costs increase.
- the benzoic acid slurry is fed to a filtration device 5(40) to separate solid benzoic acid from filtrate m a similar way as for the filtration device 2(8) .
- the filtrate i r ) (36) mainly composed of water and a trace amount of benzoic acid is sent to the wastewater treatment facility and the solid benzoic acid is sent to a dryer (38) .
- the operating conditions of the dryer are preferably maintained at a temperature in the range of 60 to 120 0 C and at a pressure in O the range of 20 to 13OkPa with a drying time of 0.5 to 2.0 hr for the high purity and yield of benzoic acid.
- filtration devices employed in this invention can be conventional pressure filters, rotary filters, tubular filters or centrifuges, which are commonly used m industrial applications for the solid- liquid separation.
- the filtration device 1(5) is of the tubular filter type and the same tubular type is preferred for other filtration devices for easier operation and maintenance.
- the material of construction for the tubular filters is stainless steel or titanium and the pore size of filter medium is m the range of 0.5 to 20 ⁇ m. If its pore size is bigger than 20/ini, some solids of small size can not be filtered and fed with the filtrate to the subsequent processes, resulting m
- the typical recovery yields from the solid wastes are about 80 to
- FIG. 1 and 2 are flow diagrams, showing the general configuration of this invention.
- the type of the filtration devices used in the following example is tubular filters made of sintered stainless steel with the average pore size of I ⁇ m. Batch tests were performed step-by-step at a pilot plant by using the solid wastes with the compositions shown in Table 1, which were simulated per a typical analysis of the solid wastes from a terephthalic acid plant.
- the extractor (3) in Fig. 1 was charged with 5 kg of the solid wastes and 17.5kg of de- ionized water and then catalysts were extracted at 45 0 C by stirring the extractor contents at 56 rpm for 60 minutes. The resulting slurry was fed to the filtration device 2(8) to separate solid and liquid. In this example, the filtration device 1(5) was not used.
- the filtrate of the filtration device 2(8) was collected in the evaporator (10) and then boiled at 100 0 C for 30 min. to evaporate excess water.
- the total amount of catalysts (Co, Mn, Br) recovered was 98.3 gram and the recovery yield of catalysts is shown in Table 2.
- the wet cake from the filtration device 2(8) was reslurried with 9 kg of water in the holding tank 1(16) and the resulting slurry was fed to the filtration device 3(18) to separate solid and liquid.
- the wet cake was washed with water and then mixed with 3 kg of water in the dissolver (21) .
- the contents of the dissolver (21) were heated to 96 0 C and well stirred at the same temperature for 30 minutes.
- the resulting slurry was filtered by the filtration device 4(24) .
- Amount of terephthalic acid recovered was 492.5 g and the recovery yield of terephthalic acid is shown in Table 2.
- the liquid filtrate of the filtration device 4(24) was fed to the crystallizer (32) , wherein benzoic acid was crystallized at 34 0 C for 1 hour.
- the resulting slurry was filtered by means of the filtration device 5(40) .
- the wet cake thus obtained was dried at 80 0 C under a vacuum pressure 60 kPa for 2 hours.
- Amount of benzoic acid recovered was 1368.7 g and its recovery yield is shown in Table 2.
- the process of this invention provides a method of recovering catalyst, benzoic acid and other aromatic acid simultaneously from the solid wastes, while the prior art processes recover only one component from the wastes.
- the present invention also allows not only to obtain economic benefits by recovering most useful chemicals from the wastes but also to minimize the environmental pollution.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention concerne un procédé de récupération de catalyseurs, d'acide benzoïque et d'autres acides aromatiques à partir des déchets solides générés par un procédé de fabrication d'un acide carboxylique aromatique. Les catalyseurs sont récupérés à partir des déchets solides en utilisant l'extraction par un solvant et la filtration. Les solides résultants sont chauffés pour dissoudre l'acide benzoïque dans l'eau et les acides aromatiques solides sont séparés par filtration. L'acide benzoïque est récupéré à partir du filtrat liquide en utilisant la cristallisation, la filtration et le séchage.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020070115133A KR100897502B1 (ko) | 2007-11-12 | 2007-11-12 | 방향족산 제조공정의 폐기물로부터 촉매, 벤조산 및방향족산의 회수 방법 |
KR10-2007-0115133 | 2007-11-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009064037A1 true WO2009064037A1 (fr) | 2009-05-22 |
Family
ID=40638867
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2008/000180 WO2009064037A1 (fr) | 2007-11-12 | 2008-01-11 | Récupération de catalyseurs, d'acide benzoïque et d'acide aromatique |
Country Status (2)
Country | Link |
---|---|
KR (1) | KR100897502B1 (fr) |
WO (1) | WO2009064037A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016023958A1 (fr) * | 2014-08-12 | 2016-02-18 | Invista Technologies S.À R.L. | Procédé de récupération d'un acide monocarboxylique aromatique |
CN106145572A (zh) * | 2015-03-23 | 2016-11-23 | 中国石油化工股份有限公司 | Pta污泥废料回收利用方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103586259B (zh) * | 2013-11-14 | 2016-05-18 | 湖北祥云(集团)化工股份有限公司 | 一种触媒回收装置 |
KR101531711B1 (ko) * | 2014-07-30 | 2015-06-26 | 한국생산기술연구원 | 테레프탈산 제조 공정 폐기물로부터의 벤조산 회수 방법 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR850000404B1 (ko) * | 1982-07-27 | 1985-03-26 | 이춘화 | 테레프탈산 제조 촉매의 재생 방법 |
WO2006007348A1 (fr) * | 2004-06-18 | 2006-01-19 | Eastman Chemical Company | Ameliorations apportees a un procede de preparation d'un filtrat pour le traitement d'un filtrat d'acide terephtalique |
KR20060122448A (ko) * | 2005-05-27 | 2006-11-30 | 삼성석유화학(주) | 테레프탈산 제조공정시 유기물질의 환류 방법 |
KR100715024B1 (ko) * | 2005-02-18 | 2007-05-09 | 삼성석유화학(주) | 테레프탈산 정제공정시 폐수로부터 촉매 회수 방법 |
-
2007
- 2007-11-12 KR KR1020070115133A patent/KR100897502B1/ko not_active IP Right Cessation
-
2008
- 2008-01-11 WO PCT/KR2008/000180 patent/WO2009064037A1/fr active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR850000404B1 (ko) * | 1982-07-27 | 1985-03-26 | 이춘화 | 테레프탈산 제조 촉매의 재생 방법 |
WO2006007348A1 (fr) * | 2004-06-18 | 2006-01-19 | Eastman Chemical Company | Ameliorations apportees a un procede de preparation d'un filtrat pour le traitement d'un filtrat d'acide terephtalique |
KR100715024B1 (ko) * | 2005-02-18 | 2007-05-09 | 삼성석유화학(주) | 테레프탈산 정제공정시 폐수로부터 촉매 회수 방법 |
KR20060122448A (ko) * | 2005-05-27 | 2006-11-30 | 삼성석유화학(주) | 테레프탈산 제조공정시 유기물질의 환류 방법 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016023958A1 (fr) * | 2014-08-12 | 2016-02-18 | Invista Technologies S.À R.L. | Procédé de récupération d'un acide monocarboxylique aromatique |
CN106660926A (zh) * | 2014-08-12 | 2017-05-10 | 英威达技术有限公司 | 用于回收芳香族单羧酸的方法 |
CN113121333A (zh) * | 2014-08-12 | 2021-07-16 | 英威达纺织(英国)有限公司 | 用于回收芳香族单羧酸的方法 |
CN106145572A (zh) * | 2015-03-23 | 2016-11-23 | 中国石油化工股份有限公司 | Pta污泥废料回收利用方法 |
Also Published As
Publication number | Publication date |
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KR100897502B1 (ko) | 2009-05-15 |
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