DE92991C - - Google Patents
Info
- Publication number
- DE92991C DE92991C DENDAT92991D DE92991DA DE92991C DE 92991 C DE92991 C DE 92991C DE NDAT92991 D DENDAT92991 D DE NDAT92991D DE 92991D A DE92991D A DE 92991DA DE 92991 C DE92991 C DE 92991C
- Authority
- DE
- Germany
- Prior art keywords
- nitrotoluene
- toluidine
- reduction
- alkalis
- way
- 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.)
- Active
Links
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 claims description 7
- 150000003568 thioethers Chemical class 0.000 claims description 7
- 230000001603 reducing Effects 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical class [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims description 5
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 5
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-Nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000004992 toluidines Chemical class 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-Nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- VOTFXKJPNQELOG-UHFFFAOYSA-N arsenic acid Chemical compound O[As](=O)=O VOTFXKJPNQELOG-UHFFFAOYSA-N 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 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
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Bis jetzt ist keine genügend rasch zum Ziele führende Methode zur Trennung des Gemisches der Nitrotoluole, welches man beim Nitriren des Toluols erhält, bekannt. Die bisherigen Methoden, welche zur Trennung dieser Nitroproducte oder ihrer durch Reduction entstandenen Amine führen, sind langwierig, mühevoll und kostspielig.Up to now there has not been a quick enough method of separating the mixture the nitrotoluenes, which are obtained by nitriding toluene, are known. The previous Methods which are used for the separation of these nitro products or their resulting from reduction Carrying amines is tedious, laborious and expensive.
Im Patent Nr. 78002 ist ein Verfahren zur partiellen Reduction der Nitroverbindungen des Toluols durch arsenige Säure bekannt geworden. Die Methode führt aber, abgesehen von dem p-Toluidin, zu einem schwer zu trennenden Gemische von o-Nitrotoluol und Azoxyverbindungen. ' .In patent no. 78002 a process for the partial reduction of the nitro compounds des Toluene became known through arsenic acid. The method leads, apart from that from the p-toluidine, to a difficult-to-separate mixture of o-nitrotoluene and Azoxy compounds. '.
Vorliegende Erfindung betrifft ein Verfahren, nach dem diese Trennung einfacher und billiger bewirkt wird.The present invention relates to a method by which this separation is simpler and cheaper is effected.
Es ist lange bekannt, dafs die Nitrokohlenwasserstoffe der aromatischen Reihe durch Behandlung mit Alkalisulfiden in ihre entsprechenden Amine verwandelt werden können. Auf diese Weise wurde seiner Zeit das Anilin aus dem Nitrobenzol von Zinin dargestellt (Journ. f. prakt. Chemie [1842], 27. Band, S. 149). Alkalisulfide sind seitdem beständig zur Reduction von Nitroverbindungen der aromatischen Reihe verwendet worden, besonders in Fällen, wo es erwünscht war, nur eine von mehreren Nitrogruppen zu reduciren.It has long been known that the nitrocarbons of the aromatic series can be treated by treatment can be converted into their corresponding amines with alkali sulfides. In this way the aniline became out of its time the nitrobenzene of Zinin (Journ. f. Prakt. Chemie [1842], Volume 27, p. 149). Since then, alkali sulfides have been resistant to the reduction of nitro compounds of aromatic compounds Series has been used, particularly in cases where only one of several was desired To reduce nitro groups.
Es hat sich nun gezeigt, dafs die Sulfide und Hydrosulfide der Alkalien und alkalischen Erden eine kräftigere reducirende Wirkung auf das p- als auf das o-Nitrotoluol ausüben, und hierauf gründet sich die den Gegenstand vorliegender Erfindung bildende neue Methode der fractionirten Reduction, um die beiden Isomeren zu trennen, und zwar so, dafs o-Nitrofoluol annähernd rein und das Paraproduct als p-Toluidin gewonnen wird.It has now been shown that the sulphides and hydrosulphides of alkalis and alkaline substances Earth have a more powerful reducing effect on p- than on o-nitrotoluene, and the new method of the present invention is based on this fractionated reduction to separate the two isomers in such a way that o-nitrofoluene almost pure and the paraproduct is obtained as p-toluidine.
Das Gemisch der Nitrotoluole wird mit den Sulfiden und Hydrosulfiden der Alkalien oder alkalischen Erden behandelt. Man verwendet von ihnen eine gröfsere Quantität, als erforderlich ist, um das vorhandene p-Nitrotoluol allein zu reduciren. Man erhält auf diese Weise ein Toluidin, welches sehr reich an p-Toluidin ist, während das Nitrotoluol, welches unreducirt zurückbleibt, zum gröfsten Theile aus o-Nitrotoluol besteht. Man kann verschiedene Sulfide und Hydrosulfide der Alkalien und alkalischen Erden verwenden, z. B. die.Sulfide und Hydrosulfide von Natrium, Kalium, Barium, Strontium und Calcium, ganz besonders aber sind die Leblanc-Soda-Rückstände . für diesen Zweck geeignet.The mixture of the nitrotoluenes is with the sulfides and hydrosulfides of the alkalis or treated with alkaline earths. A larger quantity of them is used than is necessary is to reduce the p-nitrotoluene present alone. This way you get a Toluidine, which is very rich in p-toluidine, while nitrotoluene, which is unreduced remains, consists for the most part of o-nitrotoluene. One can use different sulfides and hydrosulphides of alkalis and alkaline earths, e.g. B. die.Sulfide and hydrosulfide of sodium, potassium, barium, strontium and calcium, but they are very special Leblanc soda residue. suitable for this purpose.
200 kg des Handelsnitrotoluols (so, wie es bei der Nitrirung des Toluols erhalten wird), 400 kg Leblanc-Soda-Rückstand und 400 1 Wasser werden circa 12 Stunden lang in einem mit Rührwerk versehenen Kessel erhitzt. Die Toluidine und unveränderten Nitrotoluole werden alsdann mit Wasserdampf abgeblasen, vom Wasser getrennt und mit verdünnter Säure behandelt. Das zurückbleibende Nitrotoluol siedet200 kg of commercial nitrotoluene (as it is obtained from the nitration of toluene), 400 kg of Leblanc soda residue and 400 l of water are combined in one for about 12 hours Kettle equipped with a stirrer is heated. The toluidines and nitrotoluenes are unchanged then blown off with steam, separated from the water and treated with dilute acid. The remaining nitrotoluene boils
innerhalb 2 bis 3 Graden. Nach dem Ausfällen der Toluidine mit Alkali wird das p-Toluidin. durch Ausfrieren und Ausschleudern erhalten. .within 2 to 3 degrees. After the toluidines have been precipitated with alkali, the p-toluidine. obtained by freezing out and centrifuging. .
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE92991C true DE92991C (en) |
Family
ID=364458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT92991D Active DE92991C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE92991C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155441A1 (en) * | 1984-01-09 | 1985-09-25 | Monsanto Company | A process for separating nitration isomers of substituted benzene compounds |
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0
- DE DENDAT92991D patent/DE92991C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155441A1 (en) * | 1984-01-09 | 1985-09-25 | Monsanto Company | A process for separating nitration isomers of substituted benzene compounds |
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