CA1038878A - Cooxidation process for the production of dimethyl terephthalate - Google Patents
Cooxidation process for the production of dimethyl terephthalateInfo
- Publication number
- CA1038878A CA1038878A CA209,782A CA209782A CA1038878A CA 1038878 A CA1038878 A CA 1038878A CA 209782 A CA209782 A CA 209782A CA 1038878 A CA1038878 A CA 1038878A
- Authority
- CA
- Canada
- Prior art keywords
- oxidate
- xylene
- methyl
- toluate
- stage
- 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.)
- Expired
Links
- 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 34
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims abstract description 25
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims abstract description 22
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 claims abstract description 16
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 230000006872 improvement Effects 0.000 claims abstract description 5
- 239000007791 liquid phase Substances 0.000 claims abstract description 3
- 239000007787 solid Substances 0.000 claims description 21
- 239000012452 mother liquor Substances 0.000 claims description 19
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 abstract description 36
- 230000032050 esterification Effects 0.000 abstract description 33
- 230000009467 reduction Effects 0.000 abstract description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- 229960003903 oxygen Drugs 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 description 42
- 238000007254 oxidation reaction Methods 0.000 description 42
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 27
- 239000008096 xylene Substances 0.000 description 27
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 24
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 19
- 239000000463 material Substances 0.000 description 14
- 238000000926 separation method Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 11
- 238000005194 fractionation Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 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
- 239000007789 gas Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 |
|---|---|---|---|
| US05/403,582 US3956362A (en) | 1973-10-04 | 1973-10-04 | Cooxidation process for the production of dimethyl terephthalate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038878A true CA1038878A (en) | 1978-09-19 |
Family
ID=23596298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA209,782A Expired CA1038878A (en) | 1973-10-04 | 1974-09-23 | Cooxidation process for the production of dimethyl terephthalate |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3956362A (enExample) |
| JP (1) | JPS5833853B2 (enExample) |
| AR (1) | AR201614A1 (enExample) |
| BE (1) | BE819826A (enExample) |
| BR (1) | BR7408138D0 (enExample) |
| CA (1) | CA1038878A (enExample) |
| CH (1) | CH588439A5 (enExample) |
| DD (1) | DD114402A5 (enExample) |
| DE (1) | DE2447047A1 (enExample) |
| EG (1) | EG11190A (enExample) |
| ES (1) | ES430305A1 (enExample) |
| FI (1) | FI291374A7 (enExample) |
| FR (1) | FR2270233B1 (enExample) |
| GB (1) | GB1427897A (enExample) |
| HU (1) | HU171764B (enExample) |
| IE (1) | IE40040B1 (enExample) |
| IT (1) | IT1022563B (enExample) |
| LU (1) | LU71051A1 (enExample) |
| NL (1) | NL7411292A (enExample) |
| NO (1) | NO743367L (enExample) |
| PH (1) | PH11693A (enExample) |
| ZA (1) | ZA746333B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114436830A (zh) * | 2020-11-04 | 2022-05-06 | 长沙资材科技有限公司 | 一种用于对二甲苯空气氧化生产对苯二甲酸二酯的连续装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2894978A (en) * | 1956-07-02 | 1959-07-14 | Chemische Werke Witten Gmbh | Process of producing esters of phthalic acids by oxidation of xylene and toluic acid ester mixtures |
-
1973
- 1973-10-04 US US05/403,582 patent/US3956362A/en not_active Expired - Lifetime
-
1974
- 1974-08-23 NL NL7411292A patent/NL7411292A/xx not_active Application Discontinuation
- 1974-09-12 CH CH1263674A patent/CH588439A5/xx not_active IP Right Cessation
- 1974-09-12 BE BE148445A patent/BE819826A/xx unknown
- 1974-09-12 FR FR7430826A patent/FR2270233B1/fr not_active Expired
- 1974-09-18 NO NO743367A patent/NO743367L/no unknown
- 1974-09-23 CA CA209,782A patent/CA1038878A/en not_active Expired
- 1974-09-23 ES ES430305A patent/ES430305A1/es not_active Expired
- 1974-09-26 GB GB4183174A patent/GB1427897A/en not_active Expired
- 1974-09-27 JP JP49111393A patent/JPS5833853B2/ja not_active Expired
- 1974-09-27 AR AR255802A patent/AR201614A1/es active
- 1974-10-01 BR BR8138/74A patent/BR7408138D0/pt unknown
- 1974-10-01 IE IE2039/74A patent/IE40040B1/xx unknown
- 1974-10-01 EG EG440/74A patent/EG11190A/xx active
- 1974-10-02 DE DE19742447047 patent/DE2447047A1/de not_active Withdrawn
- 1974-10-02 IT IT28006/74A patent/IT1022563B/it active
- 1974-10-03 LU LU71051A patent/LU71051A1/xx unknown
- 1974-10-03 PH PH16370A patent/PH11693A/en unknown
- 1974-10-04 ZA ZA00746333A patent/ZA746333B/xx unknown
- 1974-10-04 HU HU74HE00000665A patent/HU171764B/hu unknown
- 1974-10-04 FI FI2913/74A patent/FI291374A7/fi unknown
- 1974-10-04 DD DD181527A patent/DD114402A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2270233B1 (enExample) | 1978-09-15 |
| IE40040L (en) | 1975-04-04 |
| AR201614A1 (es) | 1975-03-31 |
| NO743367L (enExample) | 1975-04-28 |
| FI291374A7 (enExample) | 1975-04-05 |
| BR7408138D0 (pt) | 1975-07-22 |
| ES430305A1 (es) | 1976-11-16 |
| IT1022563B (it) | 1978-04-20 |
| US3956362A (en) | 1976-05-11 |
| BE819826A (fr) | 1974-12-31 |
| NL7411292A (nl) | 1975-04-08 |
| CH588439A5 (enExample) | 1977-05-31 |
| PH11693A (en) | 1978-05-24 |
| LU71051A1 (enExample) | 1975-04-17 |
| JPS5833853B2 (ja) | 1983-07-22 |
| IE40040B1 (en) | 1979-02-28 |
| DD114402A5 (enExample) | 1975-08-05 |
| ZA746333B (en) | 1975-12-31 |
| AU7395974A (en) | 1976-04-08 |
| FR2270233A1 (enExample) | 1975-12-05 |
| JPS5059346A (enExample) | 1975-05-22 |
| DE2447047A1 (de) | 1975-04-10 |
| GB1427897A (en) | 1976-03-10 |
| EG11190A (en) | 1977-01-31 |
| HU171764B (hu) | 1978-03-28 |
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