AT96290B - Process for the preparation of hexamethylenetetramine. - Google Patents
Process for the preparation of hexamethylenetetramine.Info
- Publication number
- AT96290B AT96290B AT96290DA AT96290B AT 96290 B AT96290 B AT 96290B AT 96290D A AT96290D A AT 96290DA AT 96290 B AT96290 B AT 96290B
- Authority
- AT
- Austria
- Prior art keywords
- hexamethylenetetramine
- methylene chloride
- preparation
- ammonia
- added
- Prior art date
Links
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 title claims description 14
- 235000010299 hexamethylene tetramine Nutrition 0.000 title claims description 7
- 239000004312 hexamethylene tetramine Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- GKESTCSMPAVCFO-UHFFFAOYSA-N NC.ClO Chemical compound NC.ClO GKESTCSMPAVCFO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von Hexamethylentetramin.
Es ist bekannt, dass beim Erhitzen von Methylenchlorid mit alkoholischem Ammoniak Hexamethylentetramin entsteht. Des weiteren sind Versuche bekannt, gemäss welchen beim Erhitzen von Methylenclorid mit wässerigem Ammoniak auf höhere Temperaturen, z. B. 200c, Chlorammonium, Ammoniumformiat und Methylaminchlorhydrat gebildet wurde.
EMI1.1
tetramin in guter Ausbeute aus Methylenehlorid herstellen kann, wenn man die Körper bei Temperaturen aufeinander wirken lässt, welche 1200 nicht wesentlich übersteigen. Sehr gute Ergebnisse wurden z. B.
EMI1.2
zurück, um mit weiter sinkender Temperatur immer ungünstiger zu werden. Das Verfahren kann in Abwesenheit oder Gegenwart von Katalysatoren ausgeübt werden.
Die Mitwirkung von Katalysatoren
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Beispiel : 41 kg Methylenchlorid werden mit 10l wässeriger Ammoniakläsung, welche im Liter 0. 23 kg NH enthält, in einem Autoklaven 15 Stunden lang-auf 100'erhitzt. Nach Abdestillieren des bei dieser Temperatur noch beständigen Methylenchlorids, in vorliegendem Falle 12 kg, wird das Hexamethylentetramin aus dem Reaktionsgemisch, z. B. durch Kristallisation, gewonnen. Ausbeute : 7 2 kg = 90"o des umgesetzten Methylenclorids.
Es hat sich als zweckmässig erwiesen, mit einem Überschuss an Ammoniak zu arbeiten. Vorteilhaft kann man aber auch derart verfahren, dass man nur so viel Ammoniak zufügt, als zur Bildung von Hexamethylentetramin notwendig ist, und gleichzeitig noch zum Zwecke der Bindung der freiwerdenden Salzsäure entsprechende Mengen von säurebindenden Stoffen, z. B. Soda oder Ätzalkali, zufügt.
PATENT-ANSPRÜCHE :
1. Verfahren zur Herstellung von Hexamethylentetramin aus Methylenchlorid und Ammoniak, dadurch gekennzeichnet, dass man wässeriges Ammoniak bei unter 120 0 liegenden oder] 200 nicht wesentlich
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**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of hexamethylenetetramine.
It is known that when methylene chloride is heated with alcoholic ammonia, hexamethylenetetramine is formed. Furthermore, attempts are known, according to which when heating methylene chloride with aqueous ammonia to higher temperatures, eg. B. 200c, chlorammonium, ammonium formate and methylamine chlorohydrate was formed.
EMI1.1
tetramine can be produced in good yield from methylene chloride if the bodies are allowed to interact at temperatures which do not significantly exceed 1200. Very good results were e.g. B.
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back to become more and more unfavorable as the temperature falls further The process can be carried out in the absence or presence of catalysts.
The involvement of catalysts
EMI1.3
Example: 41 kg of methylene chloride are heated to 100 ° for 15 hours in an autoclave with 10 l of aqueous ammonia solution, which contains 0.23 kg of NH per liter. After distilling off the methylene chloride, which is still stable at this temperature, in the present case 12 kg, the hexamethylenetetramine is removed from the reaction mixture, e.g. B. by crystallization obtained. Yield: 72 kg = 90% of the converted methylene chloride.
It has been found to be useful to work with an excess of ammonia. However, it is advantageous to proceed in such a way that only as much ammonia is added as is necessary for the formation of hexamethylenetetramine, and at the same time for the purpose of binding the hydrochloric acid released, corresponding amounts of acid-binding substances, e.g. B. Soda or caustic alkali adds.
PATENT CLAIMS:
1. A process for the preparation of hexamethylenetetramine from methylene chloride and ammonia, characterized in that aqueous ammonia is used at less than 120 0 or] 200 not significantly
EMI1.4
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT96290T | 1922-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT96290B true AT96290B (en) | 1924-03-10 |
Family
ID=3615870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT96290D AT96290B (en) | 1922-04-15 | 1922-04-15 | Process for the preparation of hexamethylenetetramine. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT96290B (en) |
-
1922
- 1922-04-15 AT AT96290D patent/AT96290B/en active
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