PL91566B1 - - Google Patents
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- Publication number
- PL91566B1 PL91566B1 PL1973165130A PL16513073A PL91566B1 PL 91566 B1 PL91566 B1 PL 91566B1 PL 1973165130 A PL1973165130 A PL 1973165130A PL 16513073 A PL16513073 A PL 16513073A PL 91566 B1 PL91566 B1 PL 91566B1
- Authority
- PL
- Poland
- Prior art keywords
- dimethyl terephthalate
- methanol
- methyl
- residue
- koh
- Prior art date
Links
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 16
- 238000007254 oxidation reaction Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 12
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000006227 byproduct Substances 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 13
- -1 methyl diphenyl carboxylates Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 230000006698 induction Effects 0.000 description 7
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- LKNTUZXCVHCKLD-UHFFFAOYSA-N 4-methyl-1-(2-methylphenyl)cyclohexa-2,4-diene-1-carboxylic acid Chemical compound C1=CC(C)=CCC1(C(O)=O)C1=CC=CC=C1C LKNTUZXCVHCKLD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 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 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
- C07C51/16—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
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 |
|---|---|---|---|
| DE19722244662 DE2244662C3 (de) | 1972-09-12 | Verfahren zur Gewinnung von Terephthalsäuredimethylester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL91566B1 true PL91566B1 (en, 2012) | 1977-03-31 |
Family
ID=5856087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973165130A PL91566B1 (en, 2012) | 1972-09-12 | 1973-09-10 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4126755A (en, 2012) |
| JP (1) | JPS4966644A (en, 2012) |
| AR (1) | AR198532A1 (en, 2012) |
| AT (1) | AT326112B (en, 2012) |
| BE (1) | BE804767A (en, 2012) |
| BR (1) | BR7306983D0 (en, 2012) |
| CA (1) | CA1022180A (en, 2012) |
| CH (1) | CH580559A5 (en, 2012) |
| DD (1) | DD104973A5 (en, 2012) |
| ES (1) | ES417790A1 (en, 2012) |
| FR (1) | FR2198928B1 (en, 2012) |
| GB (1) | GB1427783A (en, 2012) |
| IN (1) | IN140025B (en, 2012) |
| IT (1) | IT990110B (en, 2012) |
| NL (1) | NL173052C (en, 2012) |
| PL (1) | PL91566B1 (en, 2012) |
| RO (1) | RO63001A (en, 2012) |
| ZA (1) | ZA735425B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2923681C2 (de) * | 1979-06-12 | 1981-11-05 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Gewinnung und Wiederverwendung von Schwermetalloxidationskatalysator aus dem Wittem-DMT-Prozeß |
| DE3045332C2 (de) * | 1980-12-02 | 1982-11-25 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Gewinnung und Wiederverwendung von Schwermetalloxidationskatalysator aus Rückständen im Witten-DMT-Prozeß |
| DE3430555A1 (de) * | 1984-08-20 | 1986-02-27 | Hoechst Ag, 6230 Frankfurt | Verfahren zur abtrennung von dimethylisophthalat und dimethylorthophthalat aus ihrem gemisch mit dimethylterephthalat |
| US4760165A (en) * | 1985-11-13 | 1988-07-26 | Teijin Petrochemical Industries, Ltd. | Recovering useful components at least containing dimethyl terephthalate from high-boiling byproducts occurring in the production of dimethyl terephthalate |
| US4886901A (en) * | 1988-11-21 | 1989-12-12 | Amoco Corporation | Method for purifying a crude dimethyl naphthalene dicarboxylate |
| 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 |
| PT96056A (pt) * | 1989-12-02 | 1991-09-13 | Hoechst Ag | Processo para a purificacao de tereftalato de dimetilo |
| US5578173A (en) * | 1995-04-03 | 1996-11-26 | Eastman Kodak Company | Removal of dimethylterephthalate from a methanolysis vapor stream |
| DE19530970A1 (de) * | 1995-08-23 | 1997-02-27 | Huels Chemische Werke Ag | Verfahren zur Aufarbeitung von Rückständen aus der Rohester-Destillation bei der Herstellung von Dimethylterephthalat (DMT) |
| KR20120027531A (ko) | 2009-06-16 | 2012-03-21 | 아미리스 인코퍼레이티드 | 시클로헥센 1,4-카르복실레이트 |
| WO2010148070A2 (en) | 2009-06-16 | 2010-12-23 | Draths Corporation | Biobased polyesters |
| US8426639B2 (en) * | 2009-06-16 | 2013-04-23 | Amyris, Inc. | Preparation of trans, trans muconic acid and trans, trans muconates |
| WO2011085311A1 (en) | 2010-01-08 | 2011-07-14 | Draths Corporation | Methods for producing isomers of muconic acid and muconate salts |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2773090A (en) * | 1953-03-10 | 1956-12-04 | Du Pont | Process for preparing pure dimethylterephthalate from the carbonylation of aromatic halides |
| DE1139827B (de) * | 1961-04-15 | 1962-11-22 | Chemische Werke Witten Gesell schaft mit beschrankter Haftung, Witten | Verfahren zur verbesserten Aufarbeitung von Terephthalsäuredimethylester und Isophthalsäuredimethylester enthaltenden Mutterlaugen. |
| DE1142858B (de) * | 1961-07-19 | 1963-01-31 | Witten Gmbh Chem Werke | Verfahren zur Gewinnung von Diphenylpolycarbonsaeuremethylestern |
-
1973
- 1973-07-10 DD DD172189A patent/DD104973A5/xx unknown
- 1973-08-01 IT IT51779/73A patent/IT990110B/it active
- 1973-08-03 IN IN1798/CAL/73A patent/IN140025B/en unknown
- 1973-08-09 ZA ZA735425A patent/ZA735425B/xx unknown
- 1973-08-11 ES ES417790A patent/ES417790A1/es not_active Expired
- 1973-09-06 AR AR249952A patent/AR198532A1/es active
- 1973-09-07 CH CH1289873A patent/CH580559A5/xx not_active IP Right Cessation
- 1973-09-07 RO RO7300076017A patent/RO63001A/ro unknown
- 1973-09-10 BR BR6983/73A patent/BR7306983D0/pt unknown
- 1973-09-10 AT AT780973A patent/AT326112B/de not_active IP Right Cessation
- 1973-09-10 PL PL1973165130A patent/PL91566B1/pl unknown
- 1973-09-11 GB GB4276673A patent/GB1427783A/en not_active Expired
- 1973-09-11 FR FR7332677A patent/FR2198928B1/fr not_active Expired
- 1973-09-11 CA CA180,722A patent/CA1022180A/en not_active Expired
- 1973-09-12 US US05/396,468 patent/US4126755A/en not_active Expired - Lifetime
- 1973-09-12 NL NLAANVRAGE7312572,A patent/NL173052C/xx not_active IP Right Cessation
- 1973-09-12 BE BE135579A patent/BE804767A/xx unknown
- 1973-09-12 JP JP48102988A patent/JPS4966644A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IN140025B (en, 2012) | 1976-09-04 |
| CH580559A5 (en, 2012) | 1976-10-15 |
| NL173052C (nl) | 1983-12-01 |
| AR198532A1 (es) | 1974-06-28 |
| NL7312572A (en, 2012) | 1974-03-14 |
| NL173052B (nl) | 1983-07-01 |
| US4126755A (en) | 1978-11-21 |
| ATA780973A (de) | 1975-02-15 |
| DD104973A5 (en, 2012) | 1974-04-05 |
| AT326112B (de) | 1975-11-25 |
| RO63001A (fr) | 1978-05-15 |
| BR7306983D0 (pt) | 1974-07-18 |
| FR2198928B1 (en, 2012) | 1977-02-25 |
| DE2244662B2 (de) | 1976-06-10 |
| IT990110B (it) | 1975-06-20 |
| ES417790A1 (es) | 1976-02-16 |
| DE2244662A1 (de) | 1974-04-04 |
| BE804767A (fr) | 1974-01-02 |
| GB1427783A (en) | 1976-03-10 |
| JPS4966644A (en, 2012) | 1974-06-27 |
| CA1022180A (en) | 1977-12-06 |
| FR2198928A1 (en, 2012) | 1974-04-05 |
| ZA735425B (en) | 1974-07-31 |
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