CA2315151A1 - Procede de production d'acides carboxyliques aromatiques - Google Patents
Procede de production d'acides carboxyliques aromatiques Download PDFInfo
- Publication number
- CA2315151A1 CA2315151A1 CA002315151A CA2315151A CA2315151A1 CA 2315151 A1 CA2315151 A1 CA 2315151A1 CA 002315151 A CA002315151 A CA 002315151A CA 2315151 A CA2315151 A CA 2315151A CA 2315151 A1 CA2315151 A1 CA 2315151A1
- Authority
- CA
- Canada
- Prior art keywords
- organic acid
- reactor
- substituted aromatic
- water
- xylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- -1 aromatic carboxylic acids Chemical class 0.000 title claims description 6
- 239000013078 crystal Substances 0.000 claims abstract description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000001301 oxygen Substances 0.000 claims abstract description 30
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 24
- 239000010941 cobalt Substances 0.000 claims abstract description 24
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000007524 organic acids Chemical class 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 23
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 129
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 56
- 239000008096 xylene Substances 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract description 76
- 230000008569 process Effects 0.000 abstract description 11
- 229960000583 acetic acid Drugs 0.000 description 43
- 238000007254 oxidation reaction Methods 0.000 description 42
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 32
- 230000003647 oxidation Effects 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 239000007788 liquid Substances 0.000 description 24
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 238000002791 soaking Methods 0.000 description 16
- 239000007789 gas Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- 241001085205 Prenanthella exigua Species 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229940011182 cobalt acetate Drugs 0.000 description 3
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004868 gas analysis Methods 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000005272 metallurgy Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910002090 carbon oxide Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 238000009870 titanium metallurgy Methods 0.000 description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229940082328 manganese acetate tetrahydrate Drugs 0.000 description 1
- CESXSDZNZGSWSP-UHFFFAOYSA-L manganese(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].CC([O-])=O.CC([O-])=O CESXSDZNZGSWSP-UHFFFAOYSA-L 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000009865 steel metallurgy Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 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
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
L'invention concerne un procédé permettant de produire par exemple de l'acide téréphtalique, le procédé comprenant les étapes consistant: à former un courant d'alimentation comprenant une fraction aromatique à substitution dialkyle et un solvant d'acide organique; à mettre le courant d'alimentation en contact avec un courant de vapeur, le courant de vapeur contenant au moins 50 % en volume d'oxygène et à une pression partielle d'oxygène d'au moins 1 psi à une température comprise entre environ 80 ·C et environ 130 ·C, en la présence d'un système de catalyseur comprenant du zirconium et du cobalt, la mise en contact s'effectuant dans un réacteur à réservoir agité; à retirer du réacteur à réservoir agité un courant de vapeur comprenant l'acide organique et de l'eau; à condenser au moins une partie de l'acide organique et de l'eau provenant du courant de vapeur; à séparer au moins une partie de l'eau de l'acide organique séparé du courant de vapeur; à ramener au moins une partie de l'acide organique condensé dans le réacteur à réservoir agité; à récupérer en continu du réacteur à réservoir agité un produit comprenant une fraction aromatique à substitution diacide; à isoler des cristaux solides de la fraction aromatique à substitution diacide du produit du réacteur; et à récupérer à partir des cristaux solides de la fraction aromatique à substitution diacide une fraction aromatique à substitution diacide ayant une pureté d'au moins 97 % en poids.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6944197P | 1997-12-15 | 1997-12-15 | |
| US60/069441 | 1997-12-15 | ||
| PCT/EP1998/008134 WO1999031038A1 (fr) | 1997-12-15 | 1998-12-14 | Procede de production d'acides carboxyliques aromatiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2315151A1 true CA2315151A1 (fr) | 1999-06-24 |
Family
ID=22089001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002315151A Abandoned CA2315151A1 (fr) | 1997-12-15 | 1998-12-14 | Procede de production d'acides carboxyliques aromatiques |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1045824A1 (fr) |
| JP (1) | JP2002508343A (fr) |
| KR (1) | KR20010033086A (fr) |
| CN (1) | CN1282314A (fr) |
| AU (1) | AU732522B2 (fr) |
| BR (1) | BR9813606A (fr) |
| CA (1) | CA2315151A1 (fr) |
| HU (1) | HUP0100656A3 (fr) |
| TR (1) | TR200001718T2 (fr) |
| WO (1) | WO1999031038A1 (fr) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6949673B2 (en) | 2000-01-12 | 2005-09-27 | E.I. Du Pont De Nemours And Company | Process for producing carboxylic acids |
| US7060853B2 (en) | 2000-01-12 | 2006-06-13 | Invista North America S.A R.L. | Method for increasing oxidation reactor production capacity |
| US7485747B2 (en) | 2001-06-04 | 2009-02-03 | Eastman Chemical Company | Two stage oxidation process for the production of aromatic dicarboxylic acids |
| US7276625B2 (en) | 2002-10-15 | 2007-10-02 | Eastman Chemical Company | Process for production of a carboxylic acid/diol mixture suitable for use in polyester production |
| US7161027B2 (en) | 2002-12-09 | 2007-01-09 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
| US7074954B2 (en) | 2002-12-09 | 2006-07-11 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
| US7132566B2 (en) | 2003-09-22 | 2006-11-07 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
| US20040215036A1 (en) | 2003-04-25 | 2004-10-28 | Robert Lin | Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam |
| CN101111312B (zh) * | 2004-12-20 | 2012-01-18 | 工艺设计中心有限公司 | 用于制备芳族羧酸的方法 |
| KR100744754B1 (ko) * | 2005-12-13 | 2007-08-01 | 삼성석유화학(주) | 방향족 카르복실산의 제조방법 |
| US20070208194A1 (en) | 2006-03-01 | 2007-09-06 | Woodruff Thomas E | Oxidation system with sidedraw secondary reactor |
| US7772424B2 (en) | 2006-03-01 | 2010-08-10 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced evaporative concentration downstream of oxidative digestion |
| US7420082B2 (en) | 2006-03-01 | 2008-09-02 | Eastman Chemical Company | Polycarboxylic acid production system employing hot liquor removal downstream of oxidative digestion |
| US7326807B2 (en) | 2006-03-01 | 2008-02-05 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced heating for oxidative digestion |
| US7816556B2 (en) | 2006-03-01 | 2010-10-19 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced multistage oxidative digestion |
| US7326808B2 (en) | 2006-03-01 | 2008-02-05 | Eastman Chemical Company | Polycarboxylic acid production system employing cooled mother liquor from oxidative digestion as feed to impurity purge system |
| US7393973B2 (en) | 2006-03-01 | 2008-07-01 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced residence time distribution for oxidative digestion |
| US8455680B2 (en) | 2008-01-15 | 2013-06-04 | Eastman Chemical Company | Carboxylic acid production process employing solvent from esterification of lignocellulosic material |
| US8614350B2 (en) | 2008-01-15 | 2013-12-24 | Eastman Chemical Company | Carboxylic acid production process employing solvent from esterification of lignocellulosic material |
| KR101704370B1 (ko) * | 2008-03-18 | 2017-02-07 | 쥐티씨 테크놀로지 유에스,엘엘씨 | 이소프탈산 및 테레프탈산의 생산을 위한 개선된 시스템 및 방법 |
| GB0807904D0 (en) * | 2008-04-30 | 2008-06-04 | Invista Technologies Srl | Oxidation reactions |
| RU2010152022A (ru) * | 2008-05-23 | 2012-06-27 | ДжиТиСи ТЕКНОЛОДЖИ ЭлПи (US) | Каталитические системы для производства кислот |
| US20100113735A1 (en) * | 2008-10-31 | 2010-05-06 | Eastman Chemical Company | Integrated Co-Production of Dicarboxylic Acids |
| CN110452392B (zh) * | 2019-08-30 | 2021-11-02 | 湘潭大学 | 一种钴基金属有机骨架材料的制备方法及其在对二甲苯氧化反应中的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562318A (en) * | 1966-11-10 | 1971-02-09 | Petro Tex Chem Corp | Catalytic oxidation process of mono-aryl compounds |
| GB1373230A (en) * | 1971-12-23 | 1974-11-06 | Mitsui Petrochemical Ind | Process for producing terephthalic acid |
| GB9104776D0 (en) * | 1991-03-07 | 1991-04-17 | Ici Plc | Process for the production of terephthalic acid |
-
1998
- 1998-12-14 BR BR9813606-2A patent/BR9813606A/pt not_active IP Right Cessation
- 1998-12-14 JP JP2000538970A patent/JP2002508343A/ja not_active Withdrawn
- 1998-12-14 KR KR1020007006448A patent/KR20010033086A/ko not_active Application Discontinuation
- 1998-12-14 EP EP98965822A patent/EP1045824A1/fr not_active Withdrawn
- 1998-12-14 CA CA002315151A patent/CA2315151A1/fr not_active Abandoned
- 1998-12-14 TR TR2000/01718T patent/TR200001718T2/xx unknown
- 1998-12-14 AU AU21610/99A patent/AU732522B2/en not_active Ceased
- 1998-12-14 WO PCT/EP1998/008134 patent/WO1999031038A1/fr not_active Application Discontinuation
- 1998-12-14 HU HU0100656A patent/HUP0100656A3/hu unknown
- 1998-12-14 CN CN98812192A patent/CN1282314A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| TR200001718T2 (tr) | 2001-01-22 |
| JP2002508343A (ja) | 2002-03-19 |
| CN1282314A (zh) | 2001-01-31 |
| WO1999031038A1 (fr) | 1999-06-24 |
| HUP0100656A3 (en) | 2002-03-28 |
| EP1045824A1 (fr) | 2000-10-25 |
| BR9813606A (pt) | 2000-10-10 |
| AU732522B2 (en) | 2001-04-26 |
| AU2161099A (en) | 1999-07-05 |
| KR20010033086A (ko) | 2001-04-25 |
| HUP0100656A2 (hu) | 2001-06-28 |
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