DE1006411B - Process for the preparation of terephthalic acid - Google Patents
Process for the preparation of terephthalic acidInfo
- Publication number
- DE1006411B DE1006411B DEB38337A DEB0038337A DE1006411B DE 1006411 B DE1006411 B DE 1006411B DE B38337 A DEB38337 A DE B38337A DE B0038337 A DEB0038337 A DE B0038337A DE 1006411 B DE1006411 B DE 1006411B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- terephthalic acid
- nitric acid
- chloromethyl
- preparation
- 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 10
- 229910017604 nitric acid Inorganic materials 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 claims description 3
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 claims 1
- DLTKEOYTIZIUKD-UHFFFAOYSA-N 4-(chloromethyl)-1-methyl-2-nitrobenzene Chemical compound CC1=CC=C(CCl)C=C1[N+]([O-])=O DLTKEOYTIZIUKD-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- QUMITRDILMWWBC-UHFFFAOYSA-N nitroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C([N+]([O-])=O)=C1 QUMITRDILMWWBC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- JTMYLQKKQFLIGV-UHFFFAOYSA-N 2-chloro-4-(chloromethyl)-1-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1Cl JTMYLQKKQFLIGV-UHFFFAOYSA-N 0.000 description 1
- ZPXGNBIFHQKREO-UHFFFAOYSA-N 2-chloroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Cl)=C1 ZPXGNBIFHQKREO-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004063 acid-resistant material Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- -1 o-nitro - 4 - chloromethyl - 2 - nitrotoluene Chemical compound 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
- C07C51/275—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids of hydrocarbyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Terephthalsäure Zusatz zur Patantanmeldung B 29904 W b /12 o Die Hauptpatentanmeldung B 29904 IVb/120 betrifft ein Verfahren zur Herstellung von Terephthalsäure, das im wesentlichen darin besteht, daß man p-Chlormethyltoluol mit Salpetersäure zunächst unter normalem Druck bis zu einem im wesentlichen aus Toluylsäure bestehenden Säuregemisch oxydiert und daran anschließend diese Rohsäure mit Salpetersäure unter erhöhtem Druck weiteroxydiert. Durch ein solches Vorgehen erhält man Terephthalsäure in Ausbeuten von über 9O0/o. Process for the production of terephthalic acid. Addition to the patent application B 29904 W b / 12 o The main patent application B 29904 IVb / 120 relates to a process for the production of terephthalic acid, which consists essentially in that one p-Chloromethyltoluene with nitric acid initially under normal pressure up to one an acid mixture consisting essentially of toluic acid and then oxidized this crude acid is further oxidized with nitric acid under increased pressure. Through a Such a procedure gives terephthalic acid in yields of over 90%.
Gemäß Zusatzpatentanmeldung B 32054 IVb/ 12o erzielt man besonders gute Ergebnisse durch Anwendung einer mindestens 320/oigen, vorzugsweise 42- bis 460/oigen Salpetersäure in der ersten Stufe, während anschließend unter erhöhtem Druck mit etwa 320/obiger Salpetersäure weiteroxydiert wird. DurchAuswaschen des Endprodukts mit Methanol wird Terephthalsäure mit einer Säurezahl von 674 erhalten. According to additional patent application B 32054 IVb / 12o one achieves particularly good results by using at least 320%, preferably 42 to 460% nitric acid in the first stage, while then under increased Pressure is further oxidized with about 320 / above nitric acid. By washing out the The end product with methanol is terephthalic acid with an acid number of 674.
Es wurde nun gefunden, daß die vorstehend genannten Verfahren insofern allgemeinerer Anwendung fähig sind, also danach auch Derivate der Terephthalsäure in gleichfalls über 900/oiger Ausbeute ohne sonderliche Schwierigkeiten hergestellt werden können. It has now been found that the above methods so far are capable of more general application, so then derivatives of terephthalic acid likewise produced in a yield of over 900% without any particular difficulty can be.
Die Produkte, wie Chlorterepbtbalsäure oder Nitroterephthalsäure u. ä. Derivate werden bereits beim Abkühlen der Reaktionslösung in außerordentlich reiner Form erhalten.The products such as chloroterepbtbalic acid or nitroterephthalic acid and the like Ä. Derivatives are already extraordinary when the reaction solution is cooled preserved in pure form.
Für das Verfahren gelten die gleichen Arbeitsbedingungen, die sich für die Herstellung der Terephthalsäure bewährt haben. The same working conditions apply to the procedure have proven themselves for the production of terephthalic acid.
Man kann die Salpetersäureoxydation in beiden Stufen ebenfalls in Gegenwart von Luft, Sauerstoff oder ähnlichen oxydierenden Gasen durchführen. Als Reaktionsgefäße kommen fiir die erste Stufe vor allem gegen Salzsäure widerstandsfähige, z. B. emaillierte Behälter in Frage, hingegen für die zweite Stufe Vorrichtungen, die aus druckfesten und gegen Salpetersäure widerstandsfähigen Materialien erstellt sind, z. B. solche aus Molvbdän-, Chrom-, Wolfram- oder Nickelstählen. Zur Schonung der Druckapparatur empfiehlt sich eine Wäsche des Zwischenprodukts mit einem geeigneten Lösungsmittel, vorzugsweise mit dem noch nicht chlormethylierten Ausgangsstoff. Dadurch werden korrodierende Chlorverbindungen von den wertvollen Apparaturen ferngehalten und nicht umgesetztes Chlormethylprodukt zurückgewonnen. Nitric acid oxidation can also be carried out in both stages in Perform in the presence of air, oxygen or similar oxidizing gases. as For the first stage, reaction vessels are primarily resistant to hydrochloric acid, z. B. enamelled containers in question, however, for the second stage devices, made of pressure-resistant and nitric acid-resistant materials are e.g. B. those made of Molvbdän, chrome, tungsten or nickel steels. For protection In the pressure apparatus, it is advisable to wash the intermediate product with a suitable one Solvent, preferably with the not yet chloromethylated starting material. This keeps corrosive chlorine compounds away from the valuable equipment and recovered unreacted chloromethyl product.
Beispiel 1 100 Teile 4-Chlormethyl-2- chlor- toluol, erhalten durch Chlormethylierung von o-Chlortoluol, werden mit 800 Teilen 450/oiger Salpetersäure 2 Stunden unter Rückfluß gekocht. Das erhaltene Oxydationsprodukt wird mit 750Teilen 320/oiger Salpetersäure 1 Stunde bei 1800 und 15 at oxydiert. Hierbei wird Luft durch die Oxydationslösung geleitet. Das nach dem Erkalten auskristallisierte Produkt wird abfiltriert und aus Wasser umkristallisiert. Man erhält 100 Teile Chlorterephthalsäure vom Fp. 316 bis 3180. Example 1 100 parts of 4-chloromethyl-2-chlorotoluene, obtained by Chloromethylation of o-chlorotoluene with 800 parts of 450% nitric acid Boiled under reflux for 2 hours. The oxidation product obtained is 750 parts 320% nitric acid is oxidized for 1 hour at 1800 and 15 atm. Here is Air through the oxidizing solution passed. The product that crystallized out after cooling is filtered off and recrystallized from water. 100 parts of chloroterephthalic acid are obtained from m.p. 316 to 3180.
Beispiel 2 100 Teile eines durch Chlormethylierung von o - Nitro - toluol hergestellten 4 - Chlormethyl - 2 - nitrotoluols werden mit 800 Teilen Salpetersäure der Dichte 1,27 zwei Stunden auf 105 bis 1100 unter Durchleiten von Luft erhitzt. Die erhaltene Oxydationslösung wird heiß in einen Reaktor gepumpt und 1 Stunde bei 1900 und 20 at oxydiert. Man läßt abkühlen, filtriert die entstandenen Kristalle ab und kristallisiert aus Wasser um. Man erhält 98 Teile Nitroterephthalsäure vom Fp. 266 bis 2680. Example 2 100 parts of a product obtained by chloromethylation of o-nitro - 4 - chloromethyl - 2 - nitrotoluene produced toluene are 800 parts Nitric acid with a density of 1.27 two hours to 105 to 1100 while passing through Air heated. The oxidizing solution obtained is pumped hot into a reactor and oxidized for 1 hour at 1900 and 20 atm. It is allowed to cool and the resulting filtered Crystals and recrystallizes from water. 98 parts of nitroterephthalic acid are obtained from m.p. 266 to 2680.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB38337A DE1006411B (en) | 1955-12-16 | 1955-12-16 | Process for the preparation of terephthalic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB38337A DE1006411B (en) | 1955-12-16 | 1955-12-16 | Process for the preparation of terephthalic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1006411B true DE1006411B (en) | 1957-04-18 |
Family
ID=6965461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB38337A Pending DE1006411B (en) | 1955-12-16 | 1955-12-16 | Process for the preparation of terephthalic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1006411B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1102129B (en) * | 1959-08-22 | 1961-03-16 | Bergwerksverband Gmbh | Process for the production of monochloroterephthalic acid |
-
1955
- 1955-12-16 DE DEB38337A patent/DE1006411B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1102129B (en) * | 1959-08-22 | 1961-03-16 | Bergwerksverband Gmbh | Process for the production of monochloroterephthalic acid |
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