DE80520C - - Google Patents
Info
- Publication number
- DE80520C DE80520C DENDAT80520D DE80520DA DE80520C DE 80520 C DE80520 C DE 80520C DE NDAT80520 D DENDAT80520 D DE NDAT80520D DE 80520D A DE80520D A DE 80520DA DE 80520 C DE80520 C DE 80520C
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- diamines
- water
- heated
- formation
- 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
- 150000004985 diamines Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000000203 mixture Chemical class 0.000 description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
! Diese Erfindung bezweckt, die an Stickstoff gebundenen Wasserstoffatome in Diaminen
'durch Methyl zu ersetzen und so methylirte Diamine bequemer und billiger herzustellen als
nach den bisher bekannten Methoden. Die so ■hergestellten Basen sollen in der Farbtechnik
!und als Arzneimittel Verwendung finden.
j Läfst man Formaldehyd auf Diamine einjwirken, so findet zunächst unter Wasseraustritt
!einfacher Condensationsvorgang statt. Die so !entstandenen Methylenverbindungen zerfallen
[leicht in die ursprünglichen Producte. Dagegen !gehen diese Methylenverbindungen durch Erihitzen
mit überschüssigem Formaldehyd unter! The purpose of this invention is to replace the hydrogen atoms bonded to nitrogen in diamines with methyl, and thus to produce methylated diamines more conveniently and cheaply than by the previously known methods. The bases produced in this way are to be used in color technology and as pharmaceuticals.
If formaldehyde is allowed to act on diamines, a simple condensation process initially takes place with the escape of water. The methylene compounds thus formed break down easily into the original products. On the other hand, these methylene compounds perish when heated with excess formaldehyde
!oder:!or:
Bildung von Kohlensäure in die beständigen Methylverbindungen über; diese Reaction tritt auch ein, wenn man Formaldehyd auf Salze der Diamine oder Mischungen derselben mit überschüssigen Säuren einwirken läfst. Bezweckt man daher die Bildung methylirter Diamine, so braucht man nur, ohne auf die anfängliche Bildung der Methylenverbindungen Rücksicht zu nehmen, die Base selbst oder ein Salz derselben mit so viel Formaldehyd zu erhitzen, dafs auf zwei zu ersetzende Wasserstoffatome drei Molecule Formaldehyd kommen. Die Umsetzung verläuft dann nach den Gleichungen: ■Formation of carbonic acid into the stable methyl compounds; this reaction occurs also one, if one uses formaldehyde on salts of diamines or mixtures thereof with Allow excess acids to act. If one aims, therefore, the formation of methylated Diamines are only needed without affecting the initial formation of the methylene compounds Be considerate of adding the base itself or a salt thereof with so much formaldehyde heat so that for every two hydrogen atoms to be replaced there are three molecules of formaldehyde. The implementation then proceeds according to the equations: ■
2 + 6CH2O= R(N[C Hs\Jt + 2 C O, + 2 H2 O R2 (N H)2 + ?, C H2O = R2 (NCH3J2 +CO2 + H2 O. 2 + 6CH 2 O = R (N [CH s \ J t + 2 C O, + 2 H 2 O R 2 (NH) 2 +?, CH 2 O = R 2 (NCH 3 J 2 + CO 2 + H 2 O.
\ Formaldehyd kann in wässeriger Lösung angewendet werden; auch kann man statt dessen· ein Gemenge von Oxymethylen und Wasser oder Paraformaldehyd und Wasser oder auch Oxymethylen oder Paraformaldehyd ohne !Wasser benutzen. \ Formaldehyde can be used in aqueous solution; a mixture of oxymethylene and water or paraformaldehyde and water or oxymethylene or paraformaldehyde without water can also be used instead.
! Die Reaction beginnt langsam schon bei ι Wasserbadtemperatur; zur genügend raschen iVollendung hat sich eine Temperatur von 4130 bis [6o° als nothwendig erwiesen. Am j besten wird daher die Operation in Autoclaven. >oder anderen geschlossenen Gefä'fsen (Röhren, 'Druckfiaschen) vorgenommen, welche eine !Steigerung der Temperatur auf i6o° ermöglichen. ! The reaction begins slowly at ι water bath temperature; for a sufficiently rapid completion a temperature of 4130 to 60 ° has been found necessary. The operation in autoclaves is therefore best. > Or other closed Gefä'fsen (tubes' Druckfiaschen) made which allow! Raising the temperature to I6O °.
I Will man nach diesem Verfahren beispiels-Iweise Dimethyldiäthylendiamin herstellen, so mischt man 1000 g Diäthylendiamin mit mindestens 1047 g Formaldehyd, den man am einfachsten in Form der käuflichen 4oprocentigen Lösung anwendet. Die Mischung erhitzt man im Antoclaven bis 150 ° steigend. Ein dreibis sechsstündiges Erhitzen genügt, um die Umwandlung zu einer vollständigen zu machen. Nach dem Erkalten scheidet man durch Zusatz von Kalihydrat die Base aus, trocknet in bekannter Weise mit festem Kalihydrat und metallischem Natrium und destillirt.I want to use this procedure for example To produce dimethyldiethylenediamine, 1000 g of diethylenediamine are mixed with it at least 1047 g of formaldehyde, which is easiest to buy in the form of the 4oprocentigen Solution applies. The mixture is heated in the antoclave up to 150 °. A three to heating for six hours is enough to make the conversion complete. After cooling, the base is separated out by adding potassium hydrate and drying is carried out in a known manner Way with solid potassium hydrate and metallic sodium and distilled.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE80520C true DE80520C (en) |
Family
ID=353062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT80520D Active DE80520C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE80520C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1466887A1 (en) * | 2003-04-10 | 2004-10-13 | Celanese Chemicals Europe GmbH | Process for the synthesis of N-methyl-dialkylamines from secundary amines and formaldehyde |
-
0
- DE DENDAT80520D patent/DE80520C/de active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1466887A1 (en) * | 2003-04-10 | 2004-10-13 | Celanese Chemicals Europe GmbH | Process for the synthesis of N-methyl-dialkylamines from secundary amines and formaldehyde |
| JP2004315523A (en) * | 2003-04-10 | 2004-11-11 | Celanese Chemicals Europe Gmbh | Method for producing n-methyl-dialkylamines from secondary dialkylamine and formaldehyde |
| US6982352B2 (en) | 2003-04-10 | 2006-01-03 | Celanese Chemicals Europe Gmbh | Process for preparing N-methyldialkylamines from secondary dialkylamines and formaldehyde |
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