DE2047579A1 - - Google Patents
Info
- Publication number
- DE2047579A1 DE2047579A1 DE19702047579 DE2047579A DE2047579A1 DE 2047579 A1 DE2047579 A1 DE 2047579A1 DE 19702047579 DE19702047579 DE 19702047579 DE 2047579 A DE2047579 A DE 2047579A DE 2047579 A1 DE2047579 A1 DE 2047579A1
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- component
- cobalt
- xylene
- reaction
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 claims description 20
- 230000003647 oxidation Effects 0.000 claims description 20
- 238000007254 oxidation reaction Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 14
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 12
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000010941 cobalt Substances 0.000 claims description 8
- 229910017052 cobalt Inorganic materials 0.000 claims description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluenecarboxylic acid Natural products CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000001869 cobalt compounds Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- -1 p-toluylic acid methyl ester Chemical class 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 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 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910020515 Co—W Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 239000002351 wastewater 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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)
- Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702047579 DE2047579B2 (de) | 1970-09-28 | 1970-09-28 | Verfahren zur Herstellung von Terephthalsäuredimethylester |
| NL7108955A NL7108955A (enrdf_load_stackoverflow) | 1970-09-28 | 1971-06-29 | |
| ES393247A ES393247A1 (es) | 1970-09-28 | 1971-07-14 | Procedimiento para la preparacion de ester dimetilico de a-cido tereftalico. |
| RO6768671A RO59479A (enrdf_load_stackoverflow) | 1970-09-28 | 1971-07-16 | |
| CA120613A CA921931A (en) | 1970-09-28 | 1971-08-16 | Process for the preparation of terephthalic acid dimethylester |
| IT2761471A IT941696B (it) | 1970-09-28 | 1971-08-18 | Procedimento per la preparazione di estere dimetilico dell acido tereftalico |
| BR586071A BR7105860D0 (pt) | 1970-09-28 | 1971-09-06 | Processo para a preparacao do ester dimetilico do acido tereflatico |
| TR1691271A TR16912A (tr) | 1970-09-28 | 1971-09-14 | Tereftalik asit dimetilesterlerinin imaline mahsus usul |
| FR7134896A FR2108653A5 (en) | 1970-09-28 | 1971-09-28 | Dimethyl terephthalate prodn - using a cobalt and a group via metal catalyst |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702047579 DE2047579B2 (de) | 1970-09-28 | 1970-09-28 | Verfahren zur Herstellung von Terephthalsäuredimethylester |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2047579A1 true DE2047579A1 (enrdf_load_stackoverflow) | 1972-03-30 |
| DE2047579B2 DE2047579B2 (de) | 1975-04-24 |
| DE2047579C3 DE2047579C3 (enrdf_load_stackoverflow) | 1975-12-04 |
Family
ID=5783559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702047579 Granted DE2047579B2 (de) | 1970-09-28 | 1970-09-28 | Verfahren zur Herstellung von Terephthalsäuredimethylester |
Country Status (9)
| Country | Link |
|---|---|
| BR (1) | BR7105860D0 (enrdf_load_stackoverflow) |
| CA (1) | CA921931A (enrdf_load_stackoverflow) |
| DE (1) | DE2047579B2 (enrdf_load_stackoverflow) |
| ES (1) | ES393247A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2108653A5 (enrdf_load_stackoverflow) |
| IT (1) | IT941696B (enrdf_load_stackoverflow) |
| NL (1) | NL7108955A (enrdf_load_stackoverflow) |
| RO (1) | RO59479A (enrdf_load_stackoverflow) |
| TR (1) | TR16912A (enrdf_load_stackoverflow) |
-
1970
- 1970-09-28 DE DE19702047579 patent/DE2047579B2/de active Granted
-
1971
- 1971-06-29 NL NL7108955A patent/NL7108955A/xx unknown
- 1971-07-14 ES ES393247A patent/ES393247A1/es not_active Expired
- 1971-07-16 RO RO6768671A patent/RO59479A/ro unknown
- 1971-08-16 CA CA120613A patent/CA921931A/en not_active Expired
- 1971-08-18 IT IT2761471A patent/IT941696B/it active
- 1971-09-06 BR BR586071A patent/BR7105860D0/pt unknown
- 1971-09-14 TR TR1691271A patent/TR16912A/xx unknown
- 1971-09-28 FR FR7134896A patent/FR2108653A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT941696B (it) | 1973-03-10 |
| ES393247A1 (es) | 1975-02-16 |
| DE2047579B2 (de) | 1975-04-24 |
| DE2047579C3 (enrdf_load_stackoverflow) | 1975-12-04 |
| BR7105860D0 (pt) | 1973-05-08 |
| CA921931A (en) | 1973-02-27 |
| FR2108653A5 (en) | 1972-05-19 |
| TR16912A (tr) | 1973-09-01 |
| NL7108955A (enrdf_load_stackoverflow) | 1972-03-30 |
| RO59479A (enrdf_load_stackoverflow) | 1976-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |