AT45443B - Process for the preparation of hexamethylene amine triguayakol. - Google Patents
Process for the preparation of hexamethylene amine triguayakol.Info
- Publication number
- AT45443B AT45443B AT45443DA AT45443B AT 45443 B AT45443 B AT 45443B AT 45443D A AT45443D A AT 45443DA AT 45443 B AT45443 B AT 45443B
- Authority
- AT
- Austria
- Prior art keywords
- triguayakol
- preparation
- hexamethylene amine
- hexamethylene
- amine
- Prior art date
Links
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 12
- 229960001867 guaiacol Drugs 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- 101100243951 Caenorhabditis elegans pie-1 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
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Verfahren zur Darstellung von Hexamethylenamintriguajakol.
Durch die Untersuchungen von Moschatos und Tollens (Liebig's Annalen der Chemie, Band 272, S. 280) wurde bekannt, dass das Hexamethylen-(tetra)-amin sich mit Phenolen zu wohlcharakterisiertcn Körpern zu verbinden vermag. Diese Additionsprodukte, welche man in neuester Zeit a) s Motekülverbindungen auffasst, stellen eine sehr handliche Form, besonders der niedrig schmelzenden Phenole dar, da diese sich sehr leicht, z. B. durch Destillation im Wasserdampfstrome, aus ihnen regenerieren lassen. In der oben genannten Arbeit berichten Moschatos und Tollens auch, dass es nicht gelinge, derartige Produkte aus Phenolen von komplizierterer Konstitution, z. B. aus Guajakol, herzustellen.
Im Gegensatz zu diesen Angaben gelingt es indes, reines, kristallisiertes Guajakol mit dem Hexamothylenamin zu einem Produkt zu vereinigen, das seiner Zusammensetzung nach als Hexamethylenamintriguajakol bezeichnet werden muss.
Beispiel I : Zu einer warmen Lösung von 6 kg Hexamethylenamin in 8 l Wasser fügt man 4 kg kristallisiertes Guajuko) und erwärmt, bis eine klare Lösung entstanden ist.
EMI1.1
methylenamintriguajakol zeigt ähnlich wie Hexamethylenamintriphenol keinen scharfen Schmelzpunkt. Es beginnt über 80 C zu erweichen und schmilzt bei etwa 95 zu einor trüben Flüssigkeit. Es ist in kaltem Alkohol und in Chloroform leicht löslich.
Beim Übergiessen mit Wasser scheiden sich Öltropfen von Guajakol ab ; während aber reines Guajakol sich erst in GO bis 70 Teilen Wasser löst, gibt das Hexamethylenamintriguajakol bereits mit 25 Teilen Wasser eine klare Lösung. Durch Destillation im Wasserdampfstrome gelingt es, aus 100 g der Verbindung 70 9 reines kristallisiertes Guajakol zu regenerieren.
Bei s pie 1 Il : An Stelle des kristallisierten Hexamethylenamins im Beispiel I verwendet man direkt die Lösung, welche erhalten wird durch Versetzen einer 40prozentigen Formaldehydlösung mit Ammoniak und verfährt im übrigen nach Beispiel 1.
Beispiel III : Man fügt zu einer 40prozentigen Formaldehydlösung eine kon-
EMI1.2
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of hexamethylene amine triguayakol.
Through the investigations of Moschatos and Tollens (Liebig's Annalen der Chemie, Volume 272, p. 280) it became known that hexamethylene (tetra) amine can combine with phenols to form well-characterized bodies. These addition products, which have recently been understood as a) s Motekülverbindungen, represent a very handy form, especially of the low-melting phenols, as these are very easy, e.g. B. by distillation in a stream of steam to regenerate from them. In the above-mentioned work, Moschatos and Tollens also report that it is not possible to obtain such products from phenols of more complex constitution, e.g. B. from guaiacol.
In contrast to this information, however, it is possible to combine pure, crystallized guaiacol with hexamethylene amine to form a product which, according to its composition, has to be called hexamethylene amine triguayakol.
Example I: 4 kg of crystallized guajuko are added to a warm solution of 6 kg of hexamethylene amine in 8 l of water and the mixture is heated until a clear solution has formed.
EMI1.1
Like hexamethyleneamine triphenol, methylenaminetriguajakol does not have a sharp melting point. It begins to soften above 80 C and melts at around 95 to a cloudy liquid. It is easily soluble in cold alcohol and in chloroform.
When water is poured over it, oil droplets separate from guaiacol; But while pure guaiacol only dissolves in 70 parts of water, hexamethylene amine triguayakol gives a clear solution with 25 parts of water. Distillation in a stream of steam makes it possible to regenerate pure crystallized guaiacol from 100 g of compound 70 9.
In the case of pie 1 II: Instead of the crystallized hexamethylene amine in Example I, the solution obtained by adding ammonia to a 40 percent formaldehyde solution is used directly, and the rest of the procedure is as in Example 1.
Example III: A 40 percent formaldehyde solution is added
EMI1.2
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE45443X | 1908-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT45443B true AT45443B (en) | 1910-12-10 |
Family
ID=5624997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT45443D AT45443B (en) | 1908-10-05 | 1909-08-28 | Process for the preparation of hexamethylene amine triguayakol. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT45443B (en) |
-
1909
- 1909-08-28 AT AT45443D patent/AT45443B/en active
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