DE2655463B2 - Verfahren zum Verestern der im Destillationsrückstand der Herstellung von Terephthalsäuredimethylester verbleibenden Rohester - Google Patents
Verfahren zum Verestern der im Destillationsrückstand der Herstellung von Terephthalsäuredimethylester verbleibenden RohesterInfo
- Publication number
- DE2655463B2 DE2655463B2 DE2655463A DE2655463A DE2655463B2 DE 2655463 B2 DE2655463 B2 DE 2655463B2 DE 2655463 A DE2655463 A DE 2655463A DE 2655463 A DE2655463 A DE 2655463A DE 2655463 B2 DE2655463 B2 DE 2655463B2
- Authority
- DE
- Germany
- Prior art keywords
- weight
- distillation residue
- methanol
- oxidate
- distillation
- 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.)
- Withdrawn
Links
- 238000004821 distillation Methods 0.000 title claims description 45
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 23
- 150000002148 esters Chemical class 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- 238000005886 esterification reaction Methods 0.000 claims description 24
- 230000032050 esterification Effects 0.000 claims description 23
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 22
- -1 Aromatic carboxylic acids Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 13
- 210000002196 fr. b Anatomy 0.000 description 8
- 210000003918 fraction a Anatomy 0.000 description 7
- 210000000540 fraction c Anatomy 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- QBHDSQZASIBAAI-UHFFFAOYSA-N 4-acetylbenzoic acid Chemical compound CC(=O)C1=CC=C(C(O)=O)C=C1 QBHDSQZASIBAAI-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery 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
- 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
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1975185698A PL115115B1 (en) | 1975-12-17 | 1975-12-17 | Method of processing of residue after raw esters distillation and residue after distillation of filtrate from crystallization obtainable in the process of dimethyl terephthalate manufacture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2655463A1 DE2655463A1 (de) | 1977-06-23 |
| DE2655463B2 true DE2655463B2 (de) | 1981-02-12 |
Family
ID=19974792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2655463A Withdrawn DE2655463B2 (de) | 1975-12-17 | 1976-12-07 | Verfahren zum Verestern der im Destillationsrückstand der Herstellung von Terephthalsäuredimethylester verbleibenden Rohester |
Country Status (7)
| Country | Link |
|---|---|
| CS (1) | CS192468B2 (enExample) |
| DE (1) | DE2655463B2 (enExample) |
| FI (1) | FI763612A7 (enExample) |
| PL (1) | PL115115B1 (enExample) |
| RO (1) | RO69922A (enExample) |
| SU (1) | SU747417A3 (enExample) |
| TR (1) | TR19694A (enExample) |
-
1975
- 1975-12-17 PL PL1975185698A patent/PL115115B1/pl unknown
-
1976
- 1976-12-07 DE DE2655463A patent/DE2655463B2/de not_active Withdrawn
- 1976-12-13 CS CS768131A patent/CS192468B2/cs unknown
- 1976-12-15 SU SU762428803A patent/SU747417A3/ru active
- 1976-12-15 FI FI763612A patent/FI763612A7/fi not_active Application Discontinuation
- 1976-12-16 RO RO7688757A patent/RO69922A/ro unknown
- 1976-12-17 TR TR19694A patent/TR19694A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU747417A3 (ru) | 1980-07-23 |
| DE2655463A1 (de) | 1977-06-23 |
| PL115115B1 (en) | 1981-03-31 |
| FI763612A7 (enExample) | 1977-06-18 |
| CS192468B2 (en) | 1979-08-31 |
| RO69922A (ro) | 1980-08-15 |
| TR19694A (tr) | 1979-10-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8263 | Opposition against grant of a patent | ||
| 8239 | Disposal/non-payment of the annual fee |