RU2213725C2 - Способ получения очищенной терефталевой кислоты - Google Patents
Способ получения очищенной терефталевой кислоты Download PDFInfo
- Publication number
- RU2213725C2 RU2213725C2 RU2000113847/04A RU2000113847A RU2213725C2 RU 2213725 C2 RU2213725 C2 RU 2213725C2 RU 2000113847/04 A RU2000113847/04 A RU 2000113847/04A RU 2000113847 A RU2000113847 A RU 2000113847A RU 2213725 C2 RU2213725 C2 RU 2213725C2
- Authority
- RU
- Russia
- Prior art keywords
- terephthalic acid
- solution
- temperature
- purified
- solvent
- Prior art date
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 315
- 238000004519 manufacturing process Methods 0.000 title description 11
- 239000002904 solvent Substances 0.000 claims abstract description 168
- 238000000034 method Methods 0.000 claims abstract description 106
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 67
- 238000001704 evaporation Methods 0.000 claims abstract description 49
- 230000008020 evaporation Effects 0.000 claims abstract description 49
- 239000002244 precipitate Substances 0.000 claims abstract description 49
- 238000010956 selective crystallization Methods 0.000 claims abstract description 35
- 238000001914 filtration Methods 0.000 claims abstract description 24
- 239000012535 impurity Substances 0.000 claims abstract description 23
- 239000006185 dispersion Substances 0.000 claims abstract description 17
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 238000000746 purification Methods 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 15
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- 238000002425 crystallisation Methods 0.000 claims description 97
- 239000013078 crystal Substances 0.000 claims description 96
- 230000008025 crystallization Effects 0.000 claims description 88
- 238000001816 cooling Methods 0.000 claims description 39
- 238000005406 washing Methods 0.000 claims description 26
- 238000002791 soaking Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 11
- 230000007423 decrease Effects 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 230000009467 reduction Effects 0.000 claims description 4
- 230000008569 process Effects 0.000 abstract description 30
- 239000000047 product Substances 0.000 abstract description 19
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 55
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 44
- 238000007254 oxidation reaction Methods 0.000 description 38
- 239000000243 solution Substances 0.000 description 38
- 230000003647 oxidation Effects 0.000 description 37
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 36
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 35
- 150000003839 salts Chemical class 0.000 description 32
- 239000000203 mixture Substances 0.000 description 26
- 238000004090 dissolution Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000000725 suspension Substances 0.000 description 17
- 239000012452 mother liquor Substances 0.000 description 15
- 238000006073 displacement reaction Methods 0.000 description 13
- 239000013557 residual solvent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002955 isolation Methods 0.000 description 12
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 12
- 230000008929 regeneration Effects 0.000 description 12
- 238000011069 regeneration method Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920001225 polyester resin Polymers 0.000 description 5
- 239000004645 polyester resin Substances 0.000 description 5
- 238000003908 quality control method Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000009434 installation Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 230000009972 noncorrosive effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- -1 if used Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- FILVIKOEJGORQS-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C FILVIKOEJGORQS-UHFFFAOYSA-N 0.000 description 2
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 2
- JBODMFWMIWWZSF-UHFFFAOYSA-N 1-(2-sulfanylethyl)pyrrolidin-2-one Chemical compound SCCN1CCCC1=O JBODMFWMIWWZSF-UHFFFAOYSA-N 0.000 description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 2
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 2
- OQILOJRSIWGQSM-UHFFFAOYSA-N 1-methylpyrrolidine-2-thione Chemical compound CN1CCCC1=S OQILOJRSIWGQSM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical compound CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- IYSGJCJSRBFZSZ-UHFFFAOYSA-N carbon monoxide;manganese;5-methylcyclopenta-1,3-diene Chemical compound [Mn].[O+]#[C-].[O+]#[C-].[O+]#[C-].C[C-]1C=CC=C1 IYSGJCJSRBFZSZ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
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
- 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/962,030 | 1997-10-31 | ||
| US08/962,030 US5840968A (en) | 1995-06-07 | 1997-10-31 | Method and apparatus for preparing purified terephthalic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2000113847A RU2000113847A (ru) | 2002-03-20 |
| RU2213725C2 true RU2213725C2 (ru) | 2003-10-10 |
Family
ID=25505339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2000113847/04A RU2213725C2 (ru) | 1997-10-31 | 1998-10-29 | Способ получения очищенной терефталевой кислоты |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5840968A (https=) |
| EP (1) | EP1030829B1 (https=) |
| JP (1) | JP4381600B2 (https=) |
| KR (1) | KR100603723B1 (https=) |
| CN (1) | CN1127471C (https=) |
| AR (1) | AR017765A1 (https=) |
| AU (1) | AU1286899A (https=) |
| BR (1) | BR9813349B1 (https=) |
| CA (1) | CA2307783C (https=) |
| DE (1) | DE69835229T2 (https=) |
| ES (1) | ES2263227T3 (https=) |
| ID (1) | ID21201A (https=) |
| MY (1) | MY119529A (https=) |
| RU (1) | RU2213725C2 (https=) |
| TR (1) | TR200001138T2 (https=) |
| TW (1) | TW505627B (https=) |
| WO (1) | WO1999023055A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2475475C1 (ru) * | 2011-12-26 | 2013-02-20 | Открытое акционерное общество "Каустик" (ОАО "Каустик") | Способ получения диамида терефталевой кислоты |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4002199A (en) * | 1998-05-29 | 1999-12-20 | Hfm International, Inc. | Method for preparing purified terephthalic acid and isophthalic acid from mixed xylenes |
| KR100642625B1 (ko) * | 1998-11-24 | 2006-11-10 | 티. 디. 빈센트 린 | 고순도 방향족 폴리카르복실산 및 이것의 유도체를 정제및 생성하는 방법 |
| US6291707B1 (en) * | 1999-03-12 | 2001-09-18 | Tsong-Dar Vincent Lin | Process of purifying and producing high purity aromatic polycarboxylic acids and derivatives thereof |
| US6392091B2 (en) * | 1998-11-24 | 2002-05-21 | Tsong-Dar Vincent Lin | Process of purifying and producing high purity aromatic polycarboxylic acids |
| AU7055500A (en) | 1999-08-30 | 2001-03-26 | Mossi & Ghisolfi Overseas S.A. | An integrated process for the production of 2,6-naphthalene dicarboxylic acid |
| US6649263B2 (en) | 2001-11-16 | 2003-11-18 | Honeywell International Inc. | Polyester resin and industrial yarn process |
| DE10206168A1 (de) * | 2002-02-14 | 2003-08-21 | Guehring Joerg | Kupplung für mudular aufgebaute Werkzeughalterarme |
| 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 |
| BR0316462A (pt) * | 2002-12-09 | 2005-10-11 | Eastman Chem Co | Processos para reduzir uma suspensão de ácido carboxìlico purificado, para purificar um produto de oxidação em estágios, para produzir um produto de ácido carboxìlico purificado, e, suspensão de ácido carboxìlico purificado |
| CN100453517C (zh) * | 2003-01-10 | 2009-01-21 | 三菱化学株式会社 | 芳香羧酸的制备方法和对苯二甲酸的制备方法 |
| US7193109B2 (en) * | 2003-03-06 | 2007-03-20 | Eastman Chemical Company | Process for production of a carboxylic acid/diol mixture suitable for use in polyester production |
| US20050059709A1 (en) * | 2003-09-15 | 2005-03-17 | Meythaler Jay M. | Treatment of a neuropathy with rapid release aminopyridine |
| US7214760B2 (en) * | 2004-01-15 | 2007-05-08 | Eastman Chemical Company | Process for production of a carboxylic acid/diol mixture suitable for use in polyester production |
| WO2006088470A2 (en) * | 2004-04-09 | 2006-08-24 | Gtc Technology Inc. | Purification of carboxylic acids by complexation with selective solvents |
| US20050288527A1 (en) * | 2004-06-28 | 2005-12-29 | Cook William L | Method for preparing free-flowing crystalline material |
| US7741515B2 (en) | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7563926B2 (en) | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7568361B2 (en) | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7361784B2 (en) | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7371894B2 (en) | 2004-09-02 | 2008-05-13 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608732B2 (en) | 2005-03-08 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692036B2 (en) | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692037B2 (en) | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7399882B2 (en) | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572932B2 (en) | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572936B2 (en) | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7586000B2 (en) | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7390921B2 (en) | 2004-09-02 | 2008-06-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7482482B2 (en) | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7910769B2 (en) | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7381836B2 (en) | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7507857B2 (en) | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7589231B2 (en) | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7683210B2 (en) | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7495125B2 (en) | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7582793B2 (en) | 2004-09-02 | 2009-09-01 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7304178B2 (en) * | 2005-05-19 | 2007-12-04 | Eastman Chemical Company | Enriched isophthalic acid composition |
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- 1998-10-29 EP EP98956315A patent/EP1030829B1/en not_active Expired - Lifetime
- 1998-10-29 AU AU12868/99A patent/AU1286899A/en not_active Abandoned
- 1998-10-29 ID IDP981421A patent/ID21201A/id unknown
- 1998-10-29 CN CN98810798A patent/CN1127471C/zh not_active Expired - Fee Related
- 1998-10-29 ES ES98956315T patent/ES2263227T3/es not_active Expired - Lifetime
- 1998-10-29 KR KR1020007004687A patent/KR100603723B1/ko not_active Expired - Fee Related
- 1998-10-29 JP JP2000518932A patent/JP4381600B2/ja not_active Expired - Fee Related
- 1998-10-29 DE DE69835229T patent/DE69835229T2/de not_active Expired - Lifetime
- 1998-10-29 RU RU2000113847/04A patent/RU2213725C2/ru not_active IP Right Cessation
- 1998-10-29 WO PCT/US1998/022942 patent/WO1999023055A1/en not_active Ceased
- 1998-10-29 TR TR2000/01138T patent/TR200001138T2/xx unknown
- 1998-10-29 CA CA002307783A patent/CA2307783C/en not_active Expired - Fee Related
- 1998-10-30 MY MYPI98004967A patent/MY119529A/en unknown
- 1998-10-30 AR ARP980105476A patent/AR017765A1/es not_active Application Discontinuation
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| RU2475475C1 (ru) * | 2011-12-26 | 2013-02-20 | Открытое акционерное общество "Каустик" (ОАО "Каустик") | Способ получения диамида терефталевой кислоты |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1278239A (zh) | 2000-12-27 |
| DE69835229T2 (de) | 2006-11-23 |
| ES2263227T3 (es) | 2006-12-01 |
| CN1127471C (zh) | 2003-11-12 |
| BR9813349A (pt) | 2000-08-22 |
| JP2001521917A (ja) | 2001-11-13 |
| WO1999023055A1 (en) | 1999-05-14 |
| TR200001138T2 (tr) | 2000-09-21 |
| EP1030829B1 (en) | 2006-07-12 |
| AU1286899A (en) | 1999-05-24 |
| BR9813349B1 (pt) | 2010-08-24 |
| TW505627B (en) | 2002-10-11 |
| EP1030829A1 (en) | 2000-08-30 |
| JP4381600B2 (ja) | 2009-12-09 |
| EP1030829A4 (en) | 2003-01-02 |
| MY119529A (en) | 2005-06-30 |
| CA2307783C (en) | 2008-12-30 |
| DE69835229D1 (de) | 2006-08-24 |
| ID21201A (id) | 1999-05-06 |
| KR20010031634A (ko) | 2001-04-16 |
| AR017765A1 (es) | 2001-10-24 |
| CA2307783A1 (en) | 1999-05-14 |
| KR100603723B1 (ko) | 2006-07-26 |
| US5840968A (en) | 1998-11-24 |
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