CS251095B2 - Method of terephthalic acid's dimethyl ester and terephthalic acid production - Google Patents
Method of terephthalic acid's dimethyl ester and terephthalic acid production Download PDFInfo
- Publication number
- CS251095B2 CS251095B2 CS851508A CS150885A CS251095B2 CS 251095 B2 CS251095 B2 CS 251095B2 CS 851508 A CS851508 A CS 851508A CS 150885 A CS150885 A CS 150885A CS 251095 B2 CS251095 B2 CS 251095B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methanol
- terephthalic acid
- ester
- fraction
- esterification
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 9
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 249
- 238000005886 esterification reaction Methods 0.000 claims description 45
- 230000032050 esterification Effects 0.000 claims description 42
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 22
- 230000003647 oxidation Effects 0.000 claims description 18
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- -1 methyl p-toluyl ester Chemical class 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 9
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 9
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 claims description 4
- 150000004702 methyl esters Chemical class 0.000 claims description 4
- RYRZSXJVEILFRR-UHFFFAOYSA-N 2,3-dimethylterephthalic acid Chemical compound CC1=C(C)C(C(O)=O)=CC=C1C(O)=O RYRZSXJVEILFRR-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000005611 electricity Effects 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 5
- 230000006835 compression Effects 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MNHWRUCVFATHDL-UHFFFAOYSA-N 2-methylterephthalaldehyde Chemical compound CC1=CC(C=O)=CC=C1C=O MNHWRUCVFATHDL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07C63/14—Monocyclic dicarboxylic acids
- C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
- C07C63/26—1,4 - Benzenedicarboxylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3407912A DE3407912C1 (de) | 1984-03-03 | 1984-03-03 | Verfahren zur Herstellung von Terephthalsaeure ueber Terephthalsaeuredimethylester aus p-Xylol und Methanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS251095B2 true CS251095B2 (en) | 1987-06-11 |
Family
ID=6229529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS851508A CS251095B2 (en) | 1984-03-03 | 1985-03-04 | Method of terephthalic acid's dimethyl ester and terephthalic acid production |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4642377A (ro) |
| EP (1) | EP0157122B1 (ro) |
| JP (1) | JPH0688937B2 (ro) |
| KR (1) | KR920003120B1 (ro) |
| BG (1) | BG45697A3 (ro) |
| BR (1) | BR8500935A (ro) |
| CS (1) | CS251095B2 (ro) |
| DD (1) | DD232912A5 (ro) |
| DE (2) | DE3407912C1 (ro) |
| EG (1) | EG17052A (ro) |
| ES (1) | ES540832A0 (ro) |
| IN (1) | IN163350B (ro) |
| MX (1) | MX162239A (ro) |
| PL (1) | PL144915B1 (ro) |
| PT (1) | PT80041B (ro) |
| RO (1) | RO91879B (ro) |
| SU (1) | SU1581218A3 (ro) |
| TR (1) | TR22497A (ro) |
| YU (1) | YU44722B (ro) |
| ZA (1) | ZA851579B (ro) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4026732A1 (de) * | 1990-08-24 | 1992-02-27 | Huels Chemische Werke Ag | Verfahren zur reinigung eines oxidationsabgases mit energierueckgewinnung |
| US6472557B1 (en) | 1999-02-10 | 2002-10-29 | Eastman Chemical Company | Process for recycling polyesters |
| CN110078284B (zh) * | 2019-04-25 | 2021-08-24 | 杭州多向流化学科技有限公司 | 用于制备对苯二甲酸的富水溶剂分级利用减排系统 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2653165A (en) * | 1950-09-27 | 1953-09-22 | California Research Corp | Oxidation process |
| DE1071688B (de) * | 1958-06-14 | 1959-12-24 | Basf Ag | Verfahren zur Verbesserung der Oxydationsgeschwindigkeit der bei Luftoxydation von xylol oder von gemischen aus xylol und p-toluylsaeuremethylestern anfallenden gemische |
| DE2916197C2 (de) * | 1979-04-21 | 1982-01-28 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Terephthalsäure aus Dimethyltherephthalat als Zwischenprodukt |
-
1984
- 1984-03-03 DE DE3407912A patent/DE3407912C1/de not_active Expired
- 1984-12-27 IN IN1039/MAS/84A patent/IN163350B/en unknown
-
1985
- 1985-02-07 EP EP85101271A patent/EP0157122B1/de not_active Expired
- 1985-02-07 DE DE8585101271T patent/DE3560053D1/de not_active Expired
- 1985-02-25 SU SU853857493A patent/SU1581218A3/ru active
- 1985-02-25 DD DD85273522A patent/DD232912A5/de unknown
- 1985-02-27 TR TR8624A patent/TR22497A/xx unknown
- 1985-02-27 RO RO117779A patent/RO91879B/ro unknown
- 1985-02-28 MX MX204465A patent/MX162239A/es unknown
- 1985-02-28 BG BG069044A patent/BG45697A3/xx unknown
- 1985-02-28 YU YU314/85A patent/YU44722B/xx unknown
- 1985-02-28 KR KR1019850001275A patent/KR920003120B1/ko not_active Expired
- 1985-03-01 ZA ZA851579A patent/ZA851579B/xx unknown
- 1985-03-01 BR BR8500935A patent/BR8500935A/pt not_active IP Right Cessation
- 1985-03-01 PL PL1985252195A patent/PL144915B1/pl unknown
- 1985-03-01 PT PT80041A patent/PT80041B/pt not_active IP Right Cessation
- 1985-03-01 ES ES540832A patent/ES540832A0/es active Granted
- 1985-03-02 EG EG12585A patent/EG17052A/xx active
- 1985-03-04 CS CS851508A patent/CS251095B2/cs unknown
- 1985-03-04 US US06/707,579 patent/US4642377A/en not_active Expired - Lifetime
- 1985-03-04 JP JP60041377A patent/JPH0688937B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ZA851579B (en) | 1985-10-30 |
| YU31485A (en) | 1987-10-31 |
| EG17052A (en) | 1994-07-30 |
| US4642377A (en) | 1987-02-10 |
| YU44722B (en) | 1990-12-31 |
| IN163350B (ro) | 1988-09-10 |
| BG45697A3 (en) | 1989-07-14 |
| JPH0688937B2 (ja) | 1994-11-09 |
| JPS60202842A (ja) | 1985-10-14 |
| ES8602590A1 (es) | 1985-12-01 |
| PL252195A1 (en) | 1985-09-24 |
| PL144915B1 (en) | 1988-07-30 |
| PT80041B (pt) | 1987-06-17 |
| ES540832A0 (es) | 1985-12-01 |
| DD232912A5 (de) | 1986-02-12 |
| RO91879B (ro) | 1987-07-03 |
| SU1581218A3 (ru) | 1990-07-23 |
| EP0157122A1 (de) | 1985-10-09 |
| KR850007056A (ko) | 1985-10-30 |
| MX162239A (es) | 1991-04-12 |
| TR22497A (tr) | 1987-09-11 |
| BR8500935A (pt) | 1985-10-22 |
| EP0157122B1 (de) | 1987-01-14 |
| RO91879A (ro) | 1987-06-30 |
| PT80041A (de) | 1985-04-01 |
| KR920003120B1 (ko) | 1992-04-20 |
| DE3560053D1 (en) | 1987-02-19 |
| DE3407912C1 (de) | 1985-05-09 |
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