CH192026A - Process for the preparation of oleylmethylaminoacetic acid. - Google Patents
Process for the preparation of oleylmethylaminoacetic acid.Info
- Publication number
- CH192026A CH192026A CH192026DA CH192026A CH 192026 A CH192026 A CH 192026A CH 192026D A CH192026D A CH 192026DA CH 192026 A CH192026 A CH 192026A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- oleylmethylaminoacetic
- preparation
- reaction
- methylating agent
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 5
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims description 3
- 229940106681 chloroacetic acid Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000012022 methylating agents Substances 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- UZCGWDVAAVGXFV-KTKRTIGZSA-N 2-[[(z)-octadec-9-enyl]amino]acetic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCNCC(O)=O UZCGWDVAAVGXFV-KTKRTIGZSA-N 0.000 claims 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940047135 glycate Drugs 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- -1 n-dodecylmethylamino Chemical group 0.000 description 1
- OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Oleylmethylaminoessigsäui#e. Im Hauptpatent ist ein Verfahren zur Herstellung von n-Dodecylmethylaminoe6sig- säure beschrieben, welches darin besteht, dass man n-Dodecylmethylamin und Chloressig säure in Gegenwart von fixen Alkalien auf einander einwirken lässt.
Gegenstand dieser Erfindung ist ein Ver fahren. zur Herstellung von Oleylmethyl- aminoe_czigsäure, welches dadurch gekenn zeichnet ist, .dass man auf Oleylamin (Oeto- decenylamin)
Chloressigsäure bezw. ein .Salz derselben einwirken lässt und die ent- eita.ndene 0l.eylaminoessigsäure (Octodecenyl- aminoessigs äuge) durch Behandlung mit einem methylierenden Mittel, zum Beispiel Methylchlorid, in die Oleylmethylaminoessig- säure überführt.
Die Oleylmethylaminoessigsäure ist be- reits bekannt. Sie ist in Form ihres Natrium salzes ein Produkt von salbenartiger Kon sistenz, das sich in kaltem Wasser mit phe- nolphthaleinalkalischer Reaktion löst und auch in wässrigem Methylalkohol, in ver dünnter Essigsäure und Salzsäure löslich ist.
Sie eignet sich zur Verwendung als Netz-, Wasch-, Reinigungs- und. Dispergiermittel in der Textil-, Leder- und Papierindustrie und andern Industrien.
Beispiel: 267 Gewiehtsteile Oleylamin werden ge schmolzen und auf 70 bis <B>90'</B> C erwäTmt, dazu tropft eine Lösung von monochloresGig- saurem Natrium im Laufe von einer Stunde ein. Man hat dafür Sorge zu tragen, dass im Reaktionsgefäss stets .deutlich phenolphtha- leinalkalische Reaktion herrscht.
Man unter bricht :den Zulauf der monochloressigsauren Lösung, wenn eine Probe des Reaktionspro- duktes klar wasserlöslich ist. Im allgemeinen genügen zur Ausführung des vorliegenden Ansatzes 120 bis<B>150</B> Gewichtsteile Mono chloressigsäure, die in wässriger Lösung bis zur phenolphthaleinalkalischen Reaktion neu tralisiert werden.
Nun lässt man bei 60 bis <B>70'</B> unter Rüh ren innerhalb einer Stunde 126 Gewichts teile Dimethylsulfat und zirka 100 Gewichts- teüe Natronlauge von 45' B6 gleichzeitig einlaufen.
Der Ansatz wird 10 Stunden bei 60 his 70 nachgerührt. Auch in dieser Reaktionsphase muss stets auf phenolphtha- leinalkalische Reaktion geachtet werden.
Process for the preparation of oleylmethylaminoacetic acid. The main patent describes a process for the production of n-dodecylmethylamino acidic acid, which consists in allowing n-dodecylmethylamine and chloroacetic acid to act on one another in the presence of fixed alkalis.
The subject of this invention is a process. for the production of oleylmethylaminoe_czig acid, which is characterized by the fact that oleylamine (oeto- decenylamine) is
Chloroacetic acid respectively. A salt of the same is allowed to act and the resulting oil eylaminoacetic acid (octodecenylaminoacetic acid) is converted into oleylmethylaminoacetic acid by treatment with a methylating agent, for example methyl chloride.
Oleylmethylaminoacetic acid is already known. In the form of its sodium salt, it is a product of an ointment-like consistency, which dissolves in cold water with an alkaline phenolphthalein reaction and is also soluble in aqueous methyl alcohol, in dilute acetic acid and hydrochloric acid.
It is suitable for use as a net, washing, cleaning and. Dispersing agent in the textile, leather and paper industry and other industries.
Example: 267 parts by weight of oleylamine are melted and heated to between 70 and 90 ° C, with a solution of monochlorous sodium glycate added dropwise over the course of one hour. Care must be taken to ensure that there is always a clear phenol-phthalene-alkaline reaction in the reaction vessel.
The following is interrupted: the feed of the monochloroacetic acid solution if a sample of the reaction product is clearly soluble in water. In general, 120 to 150 parts by weight of monochloroacetic acid, which are neutralized in aqueous solution to give an alkaline phenolphthalein reaction, are sufficient to carry out the present batch.
Now 126 parts by weight of dimethyl sulfate and about 100 parts by weight of 45 'B6 sodium hydroxide solution are run in at the same time at 60 to 70' ', while stirring.
The batch is subsequently stirred at 60 to 70 hours. In this reaction phase too, attention must always be paid to the phenol-phthalene-alkaline reaction.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE192026X | 1934-07-31 | ||
| CH186544T | 1935-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH192026A true CH192026A (en) | 1937-07-15 |
Family
ID=25721373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH192026D CH192026A (en) | 1934-07-31 | 1935-07-30 | Process for the preparation of oleylmethylaminoacetic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH192026A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2425283A (en) * | 1946-01-05 | 1947-08-05 | American Cyanamid Co | Preparation of allylglycine |
-
1935
- 1935-07-30 CH CH192026D patent/CH192026A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2425283A (en) * | 1946-01-05 | 1947-08-05 | American Cyanamid Co | Preparation of allylglycine |
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