CH238334A - Process for the preparation of a monoacylmelamine. - Google Patents
Process for the preparation of a monoacylmelamine.Info
- Publication number
- CH238334A CH238334A CH238334DA CH238334A CH 238334 A CH238334 A CH 238334A CH 238334D A CH238334D A CH 238334DA CH 238334 A CH238334 A CH 238334A
- Authority
- CH
- Switzerland
- Prior art keywords
- melamine
- monoacylmelamine
- preparation
- acetic anhydride
- plastics
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 229920000877 Melamine resin Polymers 0.000 claims description 10
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- REVYMWLDXAUASZ-UHFFFAOYSA-N n-(4,6-diamino-1,3,5-triazin-2-yl)acetamide Chemical compound CC(=O)NC1=NC(N)=NC(N)=N1 REVYMWLDXAUASZ-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000007974 melamines Chemical class 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- -1 diacetyl compound Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Monoaeylmelamins. Es wurde gefunden, dass man in guter Ausbeute Monoacylmelamine erhält, wenn man auf Melamin eine etwa äquimolekulare Menge eines Säureanhydrids einwirken lässt.
Es war überraschend und nicht vorauszuse hen, dass auf diese Weise in glatter Reaktion h'lonoacylabkömmlinge des Melamins erhält lich sind, da beim Melamin bekanntlich die drei Aminogruppen in symmetrischer Anord nung an einen heterocyclischen Ring ange schlossen sind, so dass neben der Bildung von .Monoacylderivaten auch mit der Bildung von Di- und Triacylabkömmlingen zu rechnen war, wobei dann eine entsprechende Menge Melamin hätte unverändert bleiben müssen (siehe z.
B. die Alkylierung oder Arylierung von Melamin durch Erhitzen von Melamin mit mineralsauren Salzen von aliphatischen oder aromatischen Aminen, französisches Pa tent Nr.857622). Besonders überraschend war auch die glatte Bildung der Monoacylmel- amine, da es Ostrogovich, Gazz. chim. ital. 65, 566-588, bei der Einwirkung von Essig säureanhydrid auf Melamin nur gelungen war,
eine Diacetylverbindurig zu erhalten und er ausdrücklich.angibt, dass es nicht möglich sei, eine Monoacetylverbindung zu gewinnen.
Wichtig und interessant ist es, dass die nach dem obigen Verfahren leicht erhält lichen Monoacylderivate des Melamins so stark sauren Charakter aufweisen, dass sie sich in wässerigen Alkalien glatt lösen. Ver wendet man als Säureanhydrid das innere Anhydrid einer zweibasischen Carbonsäure, z. B. Bernsteinsäureanhydrid, so erhält man ein Monoacylderivat des Melamins, welches ausser der sauren Acylaminogruppe noch eine Carbogylgruppe besitzt.
Infolgedessen binden solche Verbindungen 2 Aquivalente Alkali.
Die neuen und so leicht zugänglichen Monoacylderivate des Melamins sind wich tige Ausgangsmaterialien zur Herstellung von Kunststoffen; sie sollen besonders zur Kon densation mit Aldehyden, wie Formaldehyd, herangezogen werden.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Herstellung eines Mono- acylmelamins, dadurch gekennzeichnet, dass man auf Melamin eine äquivalente Menge Essigsäureanhydrid bei erhöhter Temperatur einwirken lässt.
Das so erhaltene Monoacetylmelamin kri stallisiert aus Dimethylformamid in Nadeln vom Schmelzpunkt 325 , ist in heissem Was ser löslich, wird durch Alkalien leicht verseift. Es soll als Zwischenprodukt zur Herstellung von Kunststoffen Verwendung finden. Beispiel: 126 Teile Melamin werden mit 102 Teilen Essigsäureanhydrid und etwa 625 Teilen Xy- lol etwa 10 Stunden am Rückflusskühler zum Sieden erhitzt.
Dann wird das Xylol mitWas- serdampf abgetrieben, der Destillationsrück- stand abgesaugt und getrocknet.
Process for the preparation of a monoalkylmelamine. It has been found that monoacylmelamines are obtained in good yield if an approximately equimolecular amount of an acid anhydride is allowed to act on melamine.
It was surprising and could not be foreseen that in this way h'lonoacylabkömmlinge of melamine are available in a smooth reaction, since in melamine it is known that the three amino groups in a symmetrical arrangement are attached to a heterocyclic ring, so that in addition to the formation of. The formation of di- and triacyl derivatives was also to be expected from monoacyl derivatives, in which case a corresponding amount of melamine should have remained unchanged (see e.g.
B. the alkylation or arylation of melamine by heating melamine with mineral acid salts of aliphatic or aromatic amines, French patent no.857622). The smooth formation of the monoacylmelamines was also particularly surprising, since Ostrogovich, Gazz. chim. Ital. 65, 566-588, with the action of acetic anhydride on melamine only succeeded
to obtain a diacetyl compound and he expressly states that it is not possible to obtain a monoacetyl compound.
It is important and interesting that the monoacyl derivatives of melamine easily obtainable by the above process have such a strong acidic character that they dissolve smoothly in aqueous alkalis. If the acid anhydride used is the internal anhydride of a dibasic carboxylic acid, e.g. B. succinic anhydride, a monoacyl derivative of melamine is obtained which, in addition to the acidic acylamino group, also has a carbogyl group.
As a result, such compounds bind 2 equivalents of alkali.
The new and easily accessible monoacyl derivatives of melamine are important starting materials for the manufacture of plastics; they should especially be used for condensation with aldehydes such as formaldehyde.
The present patent relates to a process for the production of a mono-acylmelamine, characterized in that an equivalent amount of acetic anhydride is allowed to act on melamine at an elevated temperature.
The monoacetylmelamine obtained in this way crystallizes from dimethylformamide in needles with a melting point of 325, is soluble in hot water and is easily saponified by alkalis. It should be used as an intermediate product in the manufacture of plastics. Example: 126 parts of melamine are heated to boiling with 102 parts of acetic anhydride and about 625 parts of xylene for about 10 hours in a reflux condenser.
Then the xylene is driven off with steam, the distillation residue is suctioned off and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH238334T | 1944-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH238334A true CH238334A (en) | 1945-07-15 |
Family
ID=4460540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH238334D CH238334A (en) | 1944-01-24 | 1944-01-24 | Process for the preparation of a monoacylmelamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH238334A (en) |
-
1944
- 1944-01-24 CH CH238334D patent/CH238334A/en unknown
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