JPS6119617B2 - - Google Patents
Info
- Publication number
- JPS6119617B2 JPS6119617B2 JP7377976A JP7377976A JPS6119617B2 JP S6119617 B2 JPS6119617 B2 JP S6119617B2 JP 7377976 A JP7377976 A JP 7377976A JP 7377976 A JP7377976 A JP 7377976A JP S6119617 B2 JPS6119617 B2 JP S6119617B2
- Authority
- JP
- Japan
- Prior art keywords
- oxidation
- dmt
- distillation residue
- distillation
- reaction mixture
- 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
- 238000007254 oxidation reaction Methods 0.000 claims description 74
- 238000004821 distillation Methods 0.000 claims description 58
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 52
- 230000003647 oxidation Effects 0.000 claims description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 41
- 239000003054 catalyst Substances 0.000 claims description 33
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 30
- MJHNUUNSCNRGJE-UHFFFAOYSA-N trimethyl benzene-1,2,4-tricarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(C(=O)OC)=C1 MJHNUUNSCNRGJE-UHFFFAOYSA-N 0.000 claims description 30
- 238000009835 boiling Methods 0.000 claims description 29
- 239000011541 reaction mixture Substances 0.000 claims description 21
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 15
- 238000005886 esterification reaction Methods 0.000 claims description 15
- 229910001882 dioxygen Inorganic materials 0.000 claims description 14
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 10
- 229910001385 heavy metal Inorganic materials 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 29
- 239000006227 byproduct Substances 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 229910017052 cobalt Inorganic materials 0.000 description 14
- 239000010941 cobalt Substances 0.000 description 14
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 14
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 11
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 8
- 229910052748 manganese Inorganic materials 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 230000001590 oxidative effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229940011182 cobalt acetate Drugs 0.000 description 5
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 229940071125 manganese acetate Drugs 0.000 description 5
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 5
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- -1 First Chemical group 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WJJGAKCAAJOICV-UHFFFAOYSA-N N-dimethyltyrosine Natural products CN(C)C(C(O)=O)CC1=CC=C(O)C=C1 WJJGAKCAAJOICV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZVOOGERIHVAODX-UHFFFAOYSA-N O-demycinosyltylosin Natural products O=CCC1CC(C)C(=O)C=CC(C)=CC(CO)C(CC)OC(=O)CC(O)C(C)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(O)C(C)(O)C2)C(C)O1 ZVOOGERIHVAODX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002739 metals Chemical class 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
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen 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
- GOUHYARYYWKXHS-UHFFFAOYSA-N para-formylbenzoic acid Natural products OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7377976A JPS5337632A (en) | 1976-06-24 | 1976-06-24 | Production of telephthalic acid dimethyl |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7377976A JPS5337632A (en) | 1976-06-24 | 1976-06-24 | Production of telephthalic acid dimethyl |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5337632A JPS5337632A (en) | 1978-04-06 |
JPS6119617B2 true JPS6119617B2 (fr) | 1986-05-17 |
Family
ID=13528019
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP7377976A Granted JPS5337632A (en) | 1976-06-24 | 1976-06-24 | Production of telephthalic acid dimethyl |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5337632A (fr) |
-
1976
- 1976-06-24 JP JP7377976A patent/JPS5337632A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5337632A (en) | 1978-04-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0021747B1 (fr) | Procédé pour la préparation de l'acide téréphtahlique | |
TWI382868B (zh) | 蒸餾方法 | |
CA2145307A1 (fr) | Methode de preparation d'acide adipique et d'autres acides aliphatiques dibasiques | |
US4096340A (en) | Process for the preparation of dimethyl terephthalate | |
KR20000062667A (ko) | (메트)아크릴산 제조방법 | |
JP2939346B2 (ja) | トリメリト酸無水物の製造法 | |
JPS6119617B2 (fr) | ||
JP3826435B2 (ja) | アクリル酸又はメタクリル酸の精製法 | |
JP2010163383A (ja) | アクリル酸の精製方法 | |
EP0953561A1 (fr) | Préparation du diméthyle de téréphthalate par oxydation de p-toluène aldéhyde en présence d'air | |
US4398037A (en) | Process for producing aromatic carboxylic acids and methyl esters thereof | |
JPS6353175B2 (fr) | ||
EP0018433B1 (fr) | Procédé de préparation d'acides carboxyliques aromatiques et de leurs esters méthyliques | |
JPS6123781B2 (fr) | ||
JPS6056698B2 (ja) | テレフタル酸ジメチルおよびその中間体の回収法 | |
JP4104228B2 (ja) | テレフタル酸ジメチルとイソフタル酸ジメチルとの混合物の製造方法 | |
CN110114330B (zh) | 从粗丙烯酸中分离甲醛的方法 | |
KR20060042237A (ko) | 1,3-나프탈렌디카르복실산 제조방법 | |
US3910986A (en) | Process for oxidizing beta-acyloxyethyl-toluates | |
EP0443856B1 (fr) | Préparation de l'acide isopropylidène bis-phtalique et du bisanhydride de l'acide isopropylidène bis-phtalique | |
JPS644505B2 (fr) | ||
JPS6125016B2 (fr) | ||
JPH0154340B2 (fr) | ||
JPS5941978B2 (ja) | テレフタル酸の回収法 | |
JPS6125017B2 (fr) |