CH185672A - Process for the production of dodecylaminoacetic acid. - Google Patents
Process for the production of dodecylaminoacetic acid.Info
- Publication number
- CH185672A CH185672A CH185672DA CH185672A CH 185672 A CH185672 A CH 185672A CH 185672D A CH185672D A CH 185672DA CH 185672 A CH185672 A CH 185672A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- formaldehyde
- dodecylaminoacetic
- production
- dodecylamine
- Prior art date
Links
- LNPHVNNRZGCOBK-UHFFFAOYSA-N 2-(dodecylazaniumyl)acetate Chemical compound CCCCCCCCCCCCNCC(O)=O LNPHVNNRZGCOBK-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 13
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 nitrile amine Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Dodecylaminoessigsäure. Es wurde ein Verfahren zur Herstellung von Dodecylaminoessigsäure gefunden, wel ches darin besteht, dass man Dodecylamin, Formaldehyd und Blausäure aufeinander ein wirken lässt und das gebildete Nitril durch Verseifen in die freie Dodecylaminoessigsäure überführt.
Das Verfahren wird zweckmässig in der Weise ausgeführt, dass man Formaldehyd und Dodecylamin in wässrigem Medium zu sammengibt und bei gewöhnlicher oder auch erhöhter Temperatur Blausäure zur Einwir kung bringt. Man kann auch so verfahren, dass man an Stelle von Formaldehyd Sub stanzen verwendet, welche Formaldehyd ab zuspalten vermögen,
beispielsweise Formal- dehydbisulfit. Auf das Formaldehydbisulfit lässt man dann das Dodecylamin und Blau säure oder auch ein Salz der Blausäure in wässrigem Medium einwirken und erhält in glatter Reaktion das Nitrilamin. Bei Ver wendung eines Salzes der Blausäure empfiehlt es sich, die Temperatur etwas zu steigern, jedoch nicht über<B>1000</B> hinaus. Das Nitril- amin wird nach den üblichen Verseifungs- rnethoden in die Dodecylaminoessigsäure übergeführt.
Die Dodecylaminoessigsäure ist ein farb loser kristalliner Körper, der in Wasser sehr schwer löslich ist und bei etwa<B>175</B> C unter Zersetzung schmilzt. Sie soll als Zwischen produkt für die Herstellung von Textilhilfs mitteln Verwendung finden. <I>Beispiel:</I> <B>500</B> Gewichtsteile Natriumbisulfitlösung (38prozentig werden mit 200 Gewichtsteilen Formaldehydlösung (30prozentig) vermischt und mit 370 Gewichtsteilen Dodecylamin (100prozentig) versetzt.
Man hält '/",Stunde eine Temperatur von "00-60 inne und lässt darauf die Lösung von 180 Gewichtsteilen Natriumcyanid (80prozentig) in 800 Gewichts- teile Wasser zulaufen und rührt dann 1 Stunde bei 70-80 0.
Das Nitril kann man auf folgende Weise verseifen Man versetzt das Reaktionsprodukt mit 600 Gewichtsteilen Natronlauge (35prozentig) und hält 4 Stunden eine Temperatur von 900 Man säuert nun mit verdünnter Schwefelsäure an, versetzt mit Natriumacetatlösung bis zum Verschwinden der Kongoreaktion, saugt die ausgefällteDodecylaminoessigsäure ab, wäscht mit Wasser nach und trocknet. Ausbeute etwa 90%. Man kann die Dodecylamino- essigsäure durch Umkristallisieren aus Alko hol reinigen.
Process for the production of dodecylaminoacetic acid. A process for the production of dodecylaminoacetic acid has been found which consists in allowing dodecylamine, formaldehyde and hydrocyanic acid to act on one another and converting the nitrile formed into the free dodecylaminoacetic acid by saponification.
The process is expediently carried out in such a way that formaldehyde and dodecylamine are combined in an aqueous medium and hydrocyanic acid is brought into effect at an ordinary or elevated temperature. One can also proceed in such a way that, instead of formaldehyde, substances are used which are able to split off formaldehyde,
for example formaldehyde bisulfite. The dodecylamine and hydrocyanic acid or a salt of hydrocyanic acid are then allowed to act on the formaldehyde bisulfite in an aqueous medium and the nitrile amine is obtained in a smooth reaction. When using a hydrocyanic acid salt, it is advisable to increase the temperature a little, but not more than <B> 1000 </B>. The nitrilamine is converted into dodecylaminoacetic acid according to the usual saponification methods.
Dodecylaminoacetic acid is a colorless crystalline body that is very sparingly soluble in water and melts at around <B> 175 </B> C with decomposition. It should be used as an intermediate product for the production of textile auxiliaries. <I> Example: </I> <B> 500 </B> parts by weight of sodium bisulfite solution (38 percent are mixed with 200 parts by weight of formaldehyde solution (30 percent) and 370 parts by weight of dodecylamine (100 percent) are added.
A temperature of "00-60" is maintained for 1 hour and the solution of 180 parts by weight of sodium cyanide (80 percent) in 800 parts by weight of water is then run in and the mixture is then stirred at 70-80 ° for 1 hour.
The nitrile can be saponified in the following way: 600 parts by weight of sodium hydroxide solution (35 percent) are added to the reaction product and a temperature of 900 is maintained for 4 hours with water and dry. Yield about 90%. You can purify the dodecylamino acetic acid by recrystallizing it from alcohol.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE185672X | 1934-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185672A true CH185672A (en) | 1936-08-15 |
Family
ID=5719549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185672D CH185672A (en) | 1934-07-26 | 1935-07-24 | Process for the production of dodecylaminoacetic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185672A (en) |
-
1935
- 1935-07-24 CH CH185672D patent/CH185672A/en unknown
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