DE1147571B - Verfahren zur Herstellung von Benzoldicarbonsaeuren - Google Patents
Verfahren zur Herstellung von BenzoldicarbonsaeurenInfo
- Publication number
- DE1147571B DE1147571B DEZ7784A DEZ0007784A DE1147571B DE 1147571 B DE1147571 B DE 1147571B DE Z7784 A DEZ7784 A DE Z7784A DE Z0007784 A DEZ0007784 A DE Z0007784A DE 1147571 B DE1147571 B DE 1147571B
- Authority
- DE
- Germany
- Prior art keywords
- oxygen
- reaction
- oxidation
- acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 22
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 239000001301 oxygen Substances 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 28
- 238000007254 oxidation reaction Methods 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 20
- 230000003647 oxidation Effects 0.000 claims description 20
- 238000001816 cooling Methods 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 15
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000009826 distribution Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000008096 xylene Substances 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 150000000703 Cerium Chemical class 0.000 description 1
- 230000035508 accumulation Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003738 xylenes Chemical class 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)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL252888D NL252888A (enrdf_load_stackoverflow) | 1960-01-30 | ||
| DEZ7784A DE1147571B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von Benzoldicarbonsaeuren |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ7784A DE1147571B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von Benzoldicarbonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1147571B true DE1147571B (de) | 1963-04-25 |
Family
ID=7620261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEZ7784A Pending DE1147571B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von Benzoldicarbonsaeuren |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1147571B (enrdf_load_stackoverflow) |
| NL (1) | NL252888A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135341A1 (en) * | 1983-08-09 | 1985-03-27 | Mitsubishi Kasei Corporation | Process for preparing terephthalic acid from para-xylene |
| EP0343991A3 (en) * | 1988-05-27 | 1991-07-24 | Amoco Corporation | Process for production of aromatic polycarboxylic acids |
| WO2000058257A1 (en) * | 1999-03-25 | 2000-10-05 | Franco Codignola | Process for the production of aromatic acids |
| US6833472B2 (en) | 2000-07-14 | 2004-12-21 | Eurotecnica Development And Licensing Spa | Process for the purification of aromatic carboxylic acids |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT163644B (de) * | 1947-05-09 | 1949-07-25 | Ici Ltd | Verfahren zur Herstellung von Terephthalsäure oder deren Ester |
| DE1008279B (de) * | 1954-12-29 | 1957-05-16 | Bataafsche Petroleum | Verfahren zur Herstellung von m- und p-Phthalsaeure durch Oxydation von Dialkylbenzolen |
-
0
- NL NL252888D patent/NL252888A/xx unknown
-
1960
- 1960-01-30 DE DEZ7784A patent/DE1147571B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT163644B (de) * | 1947-05-09 | 1949-07-25 | Ici Ltd | Verfahren zur Herstellung von Terephthalsäure oder deren Ester |
| DE1008279B (de) * | 1954-12-29 | 1957-05-16 | Bataafsche Petroleum | Verfahren zur Herstellung von m- und p-Phthalsaeure durch Oxydation von Dialkylbenzolen |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135341A1 (en) * | 1983-08-09 | 1985-03-27 | Mitsubishi Kasei Corporation | Process for preparing terephthalic acid from para-xylene |
| EP0343991A3 (en) * | 1988-05-27 | 1991-07-24 | Amoco Corporation | Process for production of aromatic polycarboxylic acids |
| WO2000058257A1 (en) * | 1999-03-25 | 2000-10-05 | Franco Codignola | Process for the production of aromatic acids |
| US6761860B2 (en) | 1999-03-25 | 2004-07-13 | Franco Codignola | Apparatus for the production of aromatic acids |
| US6833472B2 (en) | 2000-07-14 | 2004-12-21 | Eurotecnica Development And Licensing Spa | Process for the purification of aromatic carboxylic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| NL252888A (enrdf_load_stackoverflow) |
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