DEP0010597MA - - Google Patents
Info
- Publication number
- DEP0010597MA DEP0010597MA DEP0010597MA DE P0010597M A DEP0010597M A DE P0010597MA DE P0010597M A DEP0010597M A DE P0010597MA
- Authority
- DE
- Germany
- Prior art keywords
- terephthalic acid
- ester
- transesterification
- esterification
- acid
- 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.)
- Active
Links
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 230000032050 esterification Effects 0.000 claims description 13
- 238000005886 esterification reaction Methods 0.000 claims description 13
- 238000005809 transesterification reaction Methods 0.000 claims description 12
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 150000002334 glycols Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- 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 description 10
- 150000001298 alcohols Chemical class 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- -1 terephthalic acid Chemical class 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1793559C3 (de) | Verfahren zur Herstellung von Furan 3 carbonsaureestern Ausscheidung aus 1543804 | |
| DE2449492A1 (de) | Verfahren zur herstellung von optisch aktivem p-hydroxyphenylglycin | |
| DE969341C (de) | Verfahren zur Herstellung von Terephthalsaeuredimethylester | |
| DEP0010597MA (enrdf_load_stackoverflow) | ||
| EP0089417A1 (de) | Verfahren zur Herstellung von Phthalid | |
| DE60101020T2 (de) | Verfahren zur Herstellung von Sesamol Ameisensäure Ester und Sesamol | |
| DE2721766C2 (enrdf_load_stackoverflow) | ||
| DE2350610C3 (de) | DL-Lithiumpantoat, D (+)-üthiumpantoat, L (-)-Lithiumpantoat und Verfahren zur Herstellung der optischen Antipoden des Pantolactons | |
| DE2834168A1 (de) | Verfahren zur herstellung von 2-(2-hydroxyaethoxy)aethyl-n-( alpha , alpha , alpha -trifluor-m-tolyl)anthranilat | |
| EP0174624A1 (de) | Verfahren zur Herstellung von Milchsäureestern | |
| DE965230C (de) | Verfahren zur Wiedergewinnung von Katalysatoren und Nebenprodukten aus den Mutterlaugen der Adipinsaeuregewinnung | |
| DE1768114A1 (de) | Verfahren zur Herstellung von alpha-Ketoglutarsaeure | |
| DE2558507A1 (de) | Verfahren zur racemattrennung von dl-phenylpropanolamin | |
| DE1274132B (de) | Verfahren zur Herstellung von L-(í¬)-ª-(3, 4-Dihydroxyphenyl)-ª-methyl-alanin | |
| DE946986C (de) | Verfahren zur Herstellung von ª‡-Acetotetronsaeuren | |
| CH623583A5 (enrdf_load_stackoverflow) | ||
| DE934103C (de) | Verfahren zur Herstellung von cyclooctylierten Alkylessigsaeuren mit stark gallentreibender Wirkung | |
| DE825684C (de) | Verfahren zur Herstellung von Carbonsaeureestern | |
| DE749146C (de) | Verfahren zur Herstellung von ªŠ-Oxycarbonsaeuren | |
| AT70874B (de) | Verfahren zur Darstellung von Salzen des Betains. | |
| AT164031B (de) | Verfahren zur Herstellung von 2,4,6-Triaminophenyl-mono-äthern | |
| AT210419B (de) | Verfahren zur Herstellung von Pyridincarbonsäurealkylestern | |
| DEC0005778MA (enrdf_load_stackoverflow) | ||
| DE302826C (enrdf_load_stackoverflow) | ||
| AT215420B (de) | Verfahren zur Herstellung von 1-Methyl-3-pyrrolidyl-methylalkohol |