DE269746C - - Google Patents
Info
- Publication number
- DE269746C DE269746C DENDAT269746D DE269746DC DE269746C DE 269746 C DE269746 C DE 269746C DE NDAT269746 D DENDAT269746 D DE NDAT269746D DE 269746D C DE269746D C DE 269746DC DE 269746 C DE269746 C DE 269746C
- Authority
- DE
- Germany
- Prior art keywords
- hexamethylenetetramine
- methylrhodanide
- mixture
- formaldehyde
- methyl
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- VKYKSIONXSXAKP-UHFFFAOYSA-N Hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 7
- 229960004011 Methenamine Drugs 0.000 claims description 7
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 7
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000006011 modification reaction Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims 1
- VYHVQEYOFIYNJP-UHFFFAOYSA-N Methyl thiocyanate Chemical compound CSC#N VYHVQEYOFIYNJP-UHFFFAOYSA-N 0.000 description 5
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-Trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 3
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical class NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N HF Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- -1 potassium rhodium Chemical compound 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/18—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
JVI 269746 KLASSE 12/?. GRUPPEJVI 269746 CLASS 12 / ?. GROUP
Dr. KARL HEINRICH SCHMITZ in BRESLAU.Dr. KARL HEINRICH SCHMITZ in BRESLAU.
Verfahren zur Darstellung von Hexamethylentetramin -Methylrhodanid.Process for the preparation of hexamethylenetetramine -methylrhodanide.
Zusatz zum Patent 266788.Addendum to patent 266788.
Patentiert im Deutschen Reiche vom 8. April 1913 ab. Längste Dauer: 3.Februar 1928.Patented in the German Empire on April 8, 1913. Longest duration: February 3, 1928.
Durch Patent 266788 ist ein Verfahren zur Darstellung von Hexamethylentetramin-Methylrhodanid geschützt, welches darin besteht, daß man entweder die Methylester von Säuren auf Hexamethylentetramin einwirken läßt und die entstandenen Additionsprodukte mit leicht löslichen Rhodansalzen umsetzt, oder daß man Rhodanmethyl auf Hexamethylentetramin, mit oder ohne Zusatz eines Lösungsmittels, einwirken läßt.By patent 266788 is a method for the preparation of hexamethylenetetramine-methylrhodanide protected, which consists in either allowing the methyl esters of acids to act on hexamethylenetetramine and the resulting addition products are reacted with readily soluble rhodan salts, or that one Rhodanemethyl act on hexamethylenetetramine, with or without the addition of a solvent leaves.
Es wurde nun die technisch wertvolle Beobachtung gemacht, daß man zu derselben Verbindung auch gelangt, wenn man die Methylester der Rhodanwasserstoffsäure und anderer Säuren statt auf Hexamethylentetramin auf ein Gemisch der Lösungen von 6 Molekülen Formaldehyd und 4 Molekülen Ammoniak einwirken läßt; Es kommen hierbei die im Hauptpatent angeführten Ester, in erster Linie also Chlor-, Brom-, Jodmethyl und Dimethylsulfat in Betracht. Sofern nicht Methylrhodanid angewendet wird, erfolgt die Abscheidung des Hexamethylentetramin-Methylrhodanids durch Zugabe eines Rhodansalzes.The technically valuable observation has now been made that one can get to the same Connection is also obtained when one uses the methyl esters of hydrofluoric acid and others Acids instead of hexamethylenetetramine on a mixture of solutions of 6 molecules Allows formaldehyde and 4 molecules of ammonia to act; Here come the Esters listed in the main patent, primarily chlorine, bromine, iodine methyl and dimethyl sulfate into consideration. Unless methyl rhodanide is used, the deposition takes place of the hexamethylenetetramine methylrhodanide by adding a rhodan salt.
Statt Formaldehyd können auch dessen polymere Modifikationen, wie Trioxymethylen und Paraformaldehyd, verwendet werden.Instead of formaldehyde, its polymeric modifications, such as trioxymethylene and Paraformaldehyde, can be used.
In 4,5 kg einer 40 prozentigen Formaldehydlösung läßt man unter Rühren und Rückflußkühlung 2,72 kg einer 25 prozentigen Ammoniaklösung und hiernach 0,75 kg Methylrhodanid einfließen. Das Reaktionsgemisch, das sich stark erwärmt, wird dann weiterhin noch so lange in gelindem Sieden erhalten, bis das Methylrhodanid aufgebraucht ist. Beim Erkalten scheidet sich das Hexamethylentetramin-Methylrhodanid in großen Prismen ab.In 4.5 kg of a 40 percent formaldehyde solution, the mixture is left with stirring and reflux cooling 2.72 kg of a 25 percent ammonia solution and then 0.75 kg of methyl rhodanide are poured in. The reaction mixture that heats up a lot, then continues to simmer gently until the Methylrhodanide is used up. When cooling down, the hexamethylenetetramine methylrhodanide separates in large prisms.
•D ■ · !• D ■ ·!
Ein Gemisch von 1,8 kg Trioxymethylen -■ und 2,72 kg einer 25 prozentigen Ammoniaklösung wird unter Rühren und Rückflußkühlung so lange erwärmt, bis das Trioxymethylen gelöst ist. Dann wird die Mischung mit 1,26 kg Dimethylsulfat versetzt und so lange erwärmt, bis die Ölschicht verschwunden ist. Zum Schluß werden noch 0,97 kg Rhodankalium eingetragen. Beim Erkalten scheidet sich die Rhodanverbindung in schönen Kristallen ab.A mixture of 1.8 kg of trioxymethylene - ■ and 2.72 kg of a 25 percent ammonia solution is heated with stirring and reflux until the trioxymethylene is resolved. Then the mixture is mixed with 1.26 kg of dimethyl sulfate and so long heated until the oil layer has disappeared. Finally, 0.97 kg of potassium rhodium are added registered. When it cools, the rhodan compound separates into beautiful crystals away.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE269746C true DE269746C (en) |
Family
ID=526575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT269746D Active DE269746C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE269746C (en) |
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0
- DE DENDAT269746D patent/DE269746C/de active Active
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