BG62397B1 - Подобрено оксидиране при метода на witten-hercules заполучаване на диметилтерефталат - Google Patents
Подобрено оксидиране при метода на witten-hercules заполучаване на диметилтерефталат Download PDFInfo
- Publication number
- BG62397B1 BG62397B1 BG101958A BG10195897A BG62397B1 BG 62397 B1 BG62397 B1 BG 62397B1 BG 101958 A BG101958 A BG 101958A BG 10195897 A BG10195897 A BG 10195897A BG 62397 B1 BG62397 B1 BG 62397B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- rich
- toluic acid
- methyl ester
- oxidation
- xylene
- Prior art date
Links
- 230000003647 oxidation Effects 0.000 title claims abstract description 74
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 74
- 238000000034 method Methods 0.000 title claims abstract description 52
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title description 3
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 150000004702 methyl esters Chemical class 0.000 claims abstract description 12
- 239000007789 gas Substances 0.000 claims abstract description 10
- 239000008096 xylene Substances 0.000 claims abstract description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract 24
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims description 81
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 230000001590 oxidative effect Effects 0.000 claims description 11
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- -1 methyl p-toluic acid ester Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- OPVAJFQBSDUNQA-UHFFFAOYSA-N 3,4-dimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C OPVAJFQBSDUNQA-UHFFFAOYSA-N 0.000 claims 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 26
- 238000009434 installation Methods 0.000 description 19
- 239000000126 substance Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 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
- 238000001816 cooling Methods 0.000 description 2
- 238000006140 methanolysis reaction Methods 0.000 description 2
- GXWKILBBWPJBBF-UHFFFAOYSA-N methyl 2-(methoxymethyl)benzoate Chemical compound COCC1=CC=CC=C1C(=O)OC GXWKILBBWPJBBF-UHFFFAOYSA-N 0.000 description 2
- 125000006836 terphenylene group Chemical group 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
- C07C69/82—Terephthalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19641912A DE19641912A1 (de) | 1996-10-11 | 1996-10-11 | Verbesserte Oxidation im Witten-Hercules-Verfahren zur Herstellung von Dimethylterephthalat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG101958A BG101958A (bg) | 1998-04-30 |
| BG62397B1 true BG62397B1 (bg) | 1999-10-29 |
Family
ID=7808437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG101958A BG62397B1 (bg) | 1996-10-11 | 1997-10-10 | Подобрено оксидиране при метода на witten-hercules заполучаване на диметилтерефталат |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5869736A (cs) |
| EP (1) | EP0835861B1 (cs) |
| JP (1) | JPH10114713A (cs) |
| KR (1) | KR19980032729A (cs) |
| CN (1) | CN1180695A (cs) |
| BG (1) | BG62397B1 (cs) |
| CZ (1) | CZ319197A3 (cs) |
| DE (2) | DE19641912A1 (cs) |
| ES (1) | ES2146444T3 (cs) |
| PL (1) | PL322600A1 (cs) |
| TR (1) | TR199701137A2 (cs) |
| TW (1) | TW461882B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010007910A1 (en) * | 2000-01-12 | 2001-07-12 | Housley Samuel D. | Process for producing carboxylic acids |
| KR100787767B1 (ko) | 2001-01-10 | 2007-12-24 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 카르복실산의 개선된 제조 방법 |
| WO2002055467A1 (en) * | 2001-01-10 | 2002-07-18 | E.I. Du Pont De Nemours And Company | Method for increasing oxidation reactor production capacity |
| DE10138776C1 (de) * | 2001-08-07 | 2003-04-03 | Arteva Tech Sarl | Verfahren zur Oxidation von p-Xylol (pX) und p-Toluylsäuremethylester (pTE) mit sauerstoffhaltigen Gasen in Gegenwart eines Katalysators im Witten-Verfahren zur Herstellung von Dimethylterephthalat |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE558857A (cs) * | ||||
| JPS522896B2 (cs) * | 1973-01-18 | 1977-01-25 | ||
| DE3704720A1 (de) * | 1987-02-14 | 1988-08-25 | Huels Troisdorf | Verfahren und vorrichtung zur herstellung von benzolcarbonsaeuren bzw. benzoldicarbonsaeureestern |
| DE3904586A1 (de) * | 1989-02-16 | 1990-08-23 | Huels Chemische Werke Ag | Verfahren zur herstellung von dmt-zwischenprodukt bestimmter reinheit sowie dessen weiterverarbeitung zu reinst-dmt und/oder mittel- oder hochreiner terephthalsaeure |
-
1996
- 1996-10-11 DE DE19641912A patent/DE19641912A1/de not_active Ceased
-
1997
- 1997-08-21 EP EP97114447A patent/EP0835861B1/de not_active Expired - Lifetime
- 1997-08-21 ES ES97114447T patent/ES2146444T3/es not_active Expired - Lifetime
- 1997-08-21 DE DE59701502T patent/DE59701502D1/de not_active Expired - Lifetime
- 1997-10-09 TW TW086114855A patent/TW461882B/zh not_active IP Right Cessation
- 1997-10-09 JP JP9277368A patent/JPH10114713A/ja active Pending
- 1997-10-09 CN CN97120651A patent/CN1180695A/zh active Pending
- 1997-10-09 CZ CZ973191A patent/CZ319197A3/cs unknown
- 1997-10-09 TR TR97/01137A patent/TR199701137A2/xx unknown
- 1997-10-10 KR KR1019970052035A patent/KR19980032729A/ko not_active Withdrawn
- 1997-10-10 BG BG101958A patent/BG62397B1/bg unknown
- 1997-10-11 PL PL97322600A patent/PL322600A1/xx not_active IP Right Cessation
- 1997-10-14 US US08/949,336 patent/US5869736A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0835861B1 (de) | 2000-04-26 |
| MX9707745A (es) | 1998-08-30 |
| PL322600A1 (en) | 1998-04-14 |
| JPH10114713A (ja) | 1998-05-06 |
| ES2146444T3 (es) | 2000-08-01 |
| TR199701137A3 (tr) | 1998-04-21 |
| US5869736A (en) | 1999-02-09 |
| KR19980032729A (ko) | 1998-07-25 |
| TR199701137A2 (xx) | 1998-04-21 |
| CZ319197A3 (cs) | 1998-06-17 |
| DE59701502D1 (de) | 2000-05-31 |
| DE19641912A1 (de) | 1998-04-16 |
| CN1180695A (zh) | 1998-05-06 |
| EP0835861A1 (de) | 1998-04-15 |
| BG101958A (bg) | 1998-04-30 |
| TW461882B (en) | 2001-11-01 |
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