DE966520C - Process for the continuous production of hexamethylenetetramine - Google Patents
Process for the continuous production of hexamethylenetetramineInfo
- Publication number
- DE966520C DE966520C DEM8612A DEM0008612A DE966520C DE 966520 C DE966520 C DE 966520C DE M8612 A DEM8612 A DE M8612A DE M0008612 A DEM0008612 A DE M0008612A DE 966520 C DE966520 C DE 966520C
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- hexamethylenetetramine
- formaldehyde
- ammonia
- heat
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(WiGBI. S. 175)(WiGBI. P. 175)
AUSGEGEBEN AM 14. AUGUST 1957ISSUED AUGUST 14, 1957
INTERNAT. KLASSE C 07 d INTERNAT. CLASS C 07 d
M86i2lVbJi2pM86i2lVbJi2p
Hexamethylentetramin entsteht unter starker Wärmeentwicklung bei der Einwirkung von Formr aldehyd auf Ammoniak. Bei den heute üblichen Verfahren macht die Abführung der Reaktionswärme Schwierigkeiten. Außerdem geht, obsehon zum späteren Eindampfen der Hexamethylentetraminlösung große Wärmemengen benötigt werden, die Reaktionswärme verloren.Hexamethylenetetramine is produced under the influence of Formr with strong heat development aldehyde to ammonia. With the usual ones today Process makes it difficult to remove the heat of reaction. In addition, it works large amounts of heat are required for later evaporation of the hexamethylenetetramine solution, the heat of reaction lost.
Es ist ferner aus der deutschen Patentschrift 8o2 457 bekannt, die Reaktionswärme in dem Verfahren selbst teilweise zur Verdampfung von flüssigem Ammoniak, das in die Reaktion eingeführt wird, auszunutzen. Auch hat man schon die Reaktionswärme der Umsetzung in einem Wärmeaustauscher teilweise auf die Mutterlauge des Verfahrens übertragen;, um sie für die Eindampfung der Reaktionslösung auszunutzen (USA.-Patentschrift 2449040).It is also known from German Patent 8o2 457, the heat of reaction in the process itself partly to the evaporation of liquid ammonia that is introduced into the reaction will take advantage of it. You also have the heat of reaction of the conversion in a heat exchanger partially transferred to the mother liquor of the process; in order to use it for evaporation of the To utilize the reaction solution (U.S. Patent 2449040).
Es wurde nun gefunden, daß man die Reaktionswärme der Reaktion zwischen. Formaldehyd: und Ammoniak vollständig in dem Verfahren ausnutzen kann, wenn man die Reaktion beim Siedepunkt des Reaktionsgeniisches durchführt, so daß die Reaktionswärme eine Verdampfung der entsprechenden Menge Wasser bewirkt. Durch Wahl eines geeigneten Unter- oder Überdruckes kann die Siedetemperatur so gewählt werden, wie es die günstigste Reaktionstemperatur verlangt.It has now been found that the heat of reaction of the reaction between. Formaldehyde: and Ammonia can be fully utilized in the process if the reaction is at the boiling point of the Reaction geniisches carries out so that the heat of reaction causes the corresponding amount of water to evaporate. By choosing a suitable one Under or over pressure, the boiling temperature can be selected as it is the most favorable Reaction temperature required.
AusführungsbeispieleWorking examples
i. Durch eine Kolonne, einen Rieselturtn od. dgl. rieselt von oben eine wäßrige 'Formaldehydlösungi. By a column, a trickle belt or the like. An aqueous formaldehyde solution trickles down from above
709 632/34709 632/34
dem unten eingeleiteten gasförmigen Ammoniak entgegen. Der Druck wird z. B. auf etwa 150 mm Quecksilber, entsprechend einer Siedetemperatur des Wassers von etwa 6o°, eingestellt. Die Dosierung des Ammoniaks erfolgt z. B. so, daß durch ein pH-Regelgerät oder durch ein polarographisches Regelgerät stets auf ein neutral ausfließendes Gemisch geregelt wird. Die Reaktionskolonne ist oben über einen Kühler, in dem das abgedampfte Lösungsmittel kondensiert wird, mit einer Vakuumpumpe verbunden. Das Hexamethylentetramin wird, wie üblich, durch Eindampfen in einem Vakuum-Eindampfapparat gewonnen. Die Ausbeute an Hexamethylentetramin betragt 98,3%.against the gaseous ammonia introduced below. The pressure is z. B. to about 150 mm of mercury, corresponding to a boiling temperature of the water of about 6o °. The ammonia is metered in, for. As is so that it is always regulated by a p H -Regelgerät or by a polarographic control device to a neutral effluent mixture. The top of the reaction column is connected to a vacuum pump via a condenser in which the evaporated solvent is condensed. The hexamethylenetetramine is obtained, as usual, by evaporation in a vacuum evaporator. The yield of hexamethylenetetramine is 98.3%.
In dem abgedampften Lösungsmittel sind nur Spuren bis höchstens 2% an Ammoniak bzw. Formaldehyd zu finden.There are only traces of ammonia or formaldehyde up to a maximum of 2% in the evaporated solvent to find.
2. Zur Gewinnung eines ohne Umkristallisieren reinen Hexamethylentetramins kann man, statt das Hexamethylentetramin dlurch Eindampfen der Lösung bis zur Trockne zu gewinnen, nuir bis zur konzentrierten Lösung eindampfen und aus dieser, z. B. in einem Rieseltturm., mit Ammoniak das Hexamethylentetramin ausfällen. Die ammoniakalische Mutterlauge wird im Vakuum mit Formaldehyd zur Reaktion gebracht, wobei die Reaktionswärme wieder zum Eindampfen ausgenutzt und der zugegebene Formaldehyd durch ein pH-Regelgerät oder ein polarographisches Regelgerät dosiert wird. Durch geeignete Regelgeräte kann das Verfahren völlig kontinuierlich gestaltet werden.2. To obtain a pure hexamethylenetetramine without recrystallization, you can instead the hexamethylenetetramine can be obtained by evaporating the solution to dryness, only up to evaporate concentrated solution and from this, z. B. in a trickle tower., With ammonia that Precipitate hexamethylenetetramine. The ammoniacal mother liquor is treated with formaldehyde in vacuo brought to reaction, the heat of reaction being used again for evaporation and the added formaldehyde through a pH regulator or a polarographic control device is dosed. With suitable control devices the process can be designed to be completely continuous.
Obwohl es sich nicht um eine Ionenumsetzung, sondern um eine Moleküllumsetzung handelt, geht die Umsetzung fast momentan vor sich. Es werden 99% Ausbeute erhalten. Das Kondensat ist frei von Ammoniak und Formaldehyd.Although it is not an ion conversion, but rather a molecular conversion, the conversion is almost instantaneous. It will 99% yield obtained. The condensate is free from ammonia and formaldehyde.
Claims (3)
Deutsche Patentschrift Nr, 802457;
britische Patentschrift Nr. 441 586;
USA.-Patentschriften Nr. 1987552, 2449040; Altpeter: »Hexamethylentetramin«, 1931, S. 2 bis 4;Considered publications:
German Patent No. 802457;
British Patent No. 441,586;
U.S. Patent Nos. 1987552, 2449040; Altpeter: "Hexamethylenetetramine", 1931, pp. 2 to 4;
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM8612A DE966520C (en) | 1951-02-20 | 1951-02-20 | Process for the continuous production of hexamethylenetetramine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM8612A DE966520C (en) | 1951-02-20 | 1951-02-20 | Process for the continuous production of hexamethylenetetramine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE966520C true DE966520C (en) | 1957-08-14 |
Family
ID=7294276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM8612A Expired DE966520C (en) | 1951-02-20 | 1951-02-20 | Process for the continuous production of hexamethylenetetramine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE966520C (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1987552A (en) * | 1930-06-02 | 1935-01-08 | Mentecatini Societa Generale P | Process for the preparation of ammonium nitrate |
| GB441586A (en) * | 1934-02-24 | 1936-01-22 | Bamag Meguin Ag | Process of producing crystallized ammonium nitrate with utilization of the reaction heat for the evaporation of water |
| US2449040A (en) * | 1942-12-30 | 1948-09-07 | Chemical Construction Corp | Manufacture of hexamethylene tetramine |
| DE802457C (en) * | 1947-07-30 | 1951-02-12 | Basf Ag | Process for the preparation of hexamethylenetetramine |
-
1951
- 1951-02-20 DE DEM8612A patent/DE966520C/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1987552A (en) * | 1930-06-02 | 1935-01-08 | Mentecatini Societa Generale P | Process for the preparation of ammonium nitrate |
| GB441586A (en) * | 1934-02-24 | 1936-01-22 | Bamag Meguin Ag | Process of producing crystallized ammonium nitrate with utilization of the reaction heat for the evaporation of water |
| US2449040A (en) * | 1942-12-30 | 1948-09-07 | Chemical Construction Corp | Manufacture of hexamethylene tetramine |
| DE802457C (en) * | 1947-07-30 | 1951-02-12 | Basf Ag | Process for the preparation of hexamethylenetetramine |
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