CH140409A - Process for the preparation of a mononitro-monohalogen-terephthalic acid. - Google Patents
Process for the preparation of a mononitro-monohalogen-terephthalic acid.Info
- Publication number
- CH140409A CH140409A CH140409DA CH140409A CH 140409 A CH140409 A CH 140409A CH 140409D A CH140409D A CH 140409DA CH 140409 A CH140409 A CH 140409A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- chloro
- terephthalic acid
- mononitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- ZPXGNBIFHQKREO-UHFFFAOYSA-N 2-chloroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Cl)=C1 ZPXGNBIFHQKREO-UHFFFAOYSA-N 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- GFVQORMGWSXQME-UHFFFAOYSA-N 2-chloro-5-nitroterephthalic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=C(C(O)=O)C=C1Cl GFVQORMGWSXQME-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer blfononitro-monolialogeu-tereplitlialsilure. Behandelt man Monohalogen-terephthal- säuren mit einem Nitrierungsmittel, so erhält man leicht 2-Halogeno-5-nitro-terephthalsäu- ren. Dies ist sehr überraschend, da sich die Terephthalsäure selbst bisher nur unter ex tremen Bedingungen, nämlich mit einem grossen Überschuss von rauchender Salpeter säure und einer grossen Menge rauchender Schwefelsäure nitrieren liess.
(Berichte der Deutsch. Chem. Gesellschaft, Band 10, Seite 145; Liebigs Annalen, Band 121, Seite 90; Chem. Zentralblatt, 1912, Vol. I, Seite 17 ff.).
Man erhält ein besonders günstiges Er gebnis beim Nitrierungsverfahren, wenn man ein Gemisch von Salpetersäure und Schwe felsäure auf eine Monohalogenterephthalsäure in schwefelsaurer Lösung einwirken lässt.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Herstellung der 2-Chlor-5- introbenzol-1.4-diearbonsäure der Formel:
EMI0001.0016
dadurch gekennzeichnet, dass man die 2-Chlor- terephthalsäure mit einem nitrierenden Mittel behandelt.
Die 2-Chlor-5-nitrobenzol-1.4-diearborr- Säure kristallisiert aus 50 o/oigem Alkohol in langen, fast farblosen Nadeln und schmilzt bei ungefähr<B>2650.</B>
<I>Beispiel:</I> 40 Teile Mono-clrlor-terephthalsäur-e (vergl. Schweiz. Patent Nr. 138867) werden bei un. gefähr <B>900</B> in 200 Teilen Schwefelsäure von 661 B6 gelöst.
Nach Abkühlen auf Zimmer temperatur lässt man 28 Teile einer Nitrier- säure mit 50 % Gehalt an HN0s. rasch und unter Rühren eintropfen. Die Temperatur steigt auf etwa 650; das Reaktionsgemisch wird eine klare Lösung. Man rührt noch für kurze Zeit und lässt die Lösung abkühlen. Die neue Nitroverbindung scheidet sich bei ungefähr 500 in kristallinischer Form ab. Sie wird durch Eingiessen auf Eis isoliert. Der so erhaltene Niederschlag wird abfiltriert, gewaschen und getrocknet.
Process for the preparation of a blfononitro-monolialogeu-tereplitlialsilure. If monohalo-terephthalic acids are treated with a nitrating agent, 2-halo-5-nitro-terephthalic acids are easily obtained. This is very surprising, since the terephthalic acid itself has hitherto only been able to react under extreme conditions, namely with a large excess of fuming nitric acid and a large amount of fuming sulfuric acid.
(Reports of the German Chem. Society, Volume 10, Page 145; Liebigs Annalen, Volume 121, Page 90; Chem. Zentralblatt, 1912, Vol. I, Page 17 ff.).
A particularly favorable result is obtained in the nitration process if a mixture of nitric acid and sulfuric acid is allowed to act on a monohaloterephthalic acid in a sulfuric acid solution.
The present patent relates to a process for the preparation of 2-chloro-5-introbenzene-1,4-diacid of the formula:
EMI0001.0016
characterized in that the 2-chloro terephthalic acid is treated with a nitrating agent.
The 2-chloro-5-nitrobenzene-1,4-diearboric acid crystallizes from 50% alcohol in long, almost colorless needles and melts at about <B> 2650. </B>
<I> Example: </I> 40 parts of mono-chloro-terephthalic acid (see Swiss patent no. 138867) are used by un. danger <B> 900 </B> dissolved in 200 parts of sulfuric acid of 661 B6.
After cooling to room temperature, 28 parts of a nitrating acid with 50% HNO content are left. Drip in quickly while stirring. The temperature rises to about 650; the reaction mixture becomes a clear solution. The mixture is stirred for a short time and the solution is allowed to cool. The new nitro compound separates out in crystalline form at around 500. It is isolated by pouring over ice. The precipitate obtained in this way is filtered off, washed and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE140409X | 1927-11-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH140409A true CH140409A (en) | 1930-06-15 |
Family
ID=5668204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH140409D CH140409A (en) | 1927-11-11 | 1928-11-08 | Process for the preparation of a mononitro-monohalogen-terephthalic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH140409A (en) |
-
1928
- 1928-11-08 CH CH140409D patent/CH140409A/en unknown
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