BE558857A - - Google Patents
Info
- Publication number
- BE558857A BE558857A BE558857DA BE558857A BE 558857 A BE558857 A BE 558857A BE 558857D A BE558857D A BE 558857DA BE 558857 A BE558857 A BE 558857A
- Authority
- BE
- Belgium
- Prior art keywords
- oxidation
- xylenes
- acids
- xylene
- treatment
- Prior art date
Links
- 230000003647 oxidation Effects 0.000 claims description 44
- 238000007254 oxidation reaction Methods 0.000 claims description 44
- 239000008096 xylene Substances 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 15
- 150000003738 xylenes Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000011780 sodium chloride Substances 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 9
- -1 aliphatic alcohols Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000003022 phthalic acids Chemical class 0.000 claims description 7
- 125000005425 toluyl group Chemical group 0.000 claims description 7
- 230000002035 prolonged Effects 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 3
- 230000001131 transforming Effects 0.000 claims description 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000007127 saponification reaction Methods 0.000 description 7
- WOZVHXUHUFLZGK-UHFFFAOYSA-N Dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- XCGBFXNVKPHVEQ-UHFFFAOYSA-N cobalt;2,3-dihydroxybutanedioic acid;ethane-1,2-diamine Chemical compound [Co].NCCN.NCCN.NCCN.OC(=O)C(O)C(O)C(O)=O XCGBFXNVKPHVEQ-UHFFFAOYSA-N 0.000 description 3
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 240000007170 Cocos nucifera Species 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000014121 butter Nutrition 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052803 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N P-Toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- NMNZGKIKHBYUNG-UHFFFAOYSA-L cobalt(2+);hexanoate Chemical compound [Co+2].CCCCCC([O-])=O.CCCCCC([O-])=O NMNZGKIKHBYUNG-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001747 exhibiting Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000725 suspension 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
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
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)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE558857A true BE558857A (da) |
Family
ID=181775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE558857D BE558857A (da) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE558857A (da) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0835861A1 (de) * | 1996-10-11 | 1998-04-15 | Hüls Aktiengesellschaft | Verbesserte Oxidation im Witten-Hercules-Verfahren zur Herstellung von Dimethylterephthalat |
-
0
- BE BE558857D patent/BE558857A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0835861A1 (de) * | 1996-10-11 | 1998-04-15 | Hüls Aktiengesellschaft | Verbesserte Oxidation im Witten-Hercules-Verfahren zur Herstellung von Dimethylterephthalat |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2501673A1 (fr) | Procede continu de production d'acide terephtalique | |
| JP2000514077A (ja) | アクリル酸及びメタクリル酸の精製法 | |
| CA2222365C (fr) | Procede de traitement de melanges reactionnels issus de l'oxydation du cyclohexane | |
| FR2502144A1 (fr) | Procede pour produire du lactate de methyle et procede pour separer l'a-acetoxy- ou propionyloxy-propionaldehyde d'une solution aqueuse | |
| RU2296743C2 (ru) | Способ получения адипиновой кислоты | |
| US2894978A (en) | Process of producing esters of phthalic acids by oxidation of xylene and toluic acid ester mixtures | |
| EP0021525B1 (fr) | Procédé pour la fabrication de composés carboxylés | |
| EP0444132A1 (en) | PROCESS FOR THE PURIFICATION OF A CRUDE NAPHTHALENE DICARBOXYLATE DIMETHYL. | |
| BE558857A (da) | ||
| US2879289A (en) | Oxidation of alkyl benzenes in the presence of alkanols | |
| US3726917A (en) | Process for preparing adipic acid | |
| EP0804403A1 (en) | A method for forming two terminal carboxylic acid groups from an ozonide | |
| CH622766A5 (en) | Process for the preparation of terephthalic acid | |
| US3555083A (en) | Process for the purification of lower fatty acids | |
| US5107020A (en) | Method for producing purified trimesic acid | |
| CA2052228A1 (fr) | Procede de preparation d'oxyde borique par hydrolyse du borate de methyle et sa mise en oeuvre dans l'oxydation d'hydrocarbures satures en alcools. | |
| US5030749A (en) | Method for producing purified trimesic acid | |
| US6563001B1 (en) | Method for separating and purifying carboxylic acid derived from the direct oxidation of a hydrocarbon | |
| RU2254324C2 (ru) | Непрерывный способ получения высокочистой терефталевой кислоты | |
| US3778471A (en) | Process for producing aliphatic carboxylic acids and aromatic carboxylic acids | |
| BE589110A (da) | ||
| JPS6229549A (ja) | Ｐ−トルイル酸の製造法 | |
| BE573049A (da) | ||
| BE510412A (da) | ||
| BE560189A (da) |