CH292641A - Process for the preparation of a new iminodicarboxylic acid derivative. - Google Patents
Process for the preparation of a new iminodicarboxylic acid derivative.Info
- Publication number
- CH292641A CH292641A CH292641DA CH292641A CH 292641 A CH292641 A CH 292641A CH 292641D A CH292641D A CH 292641DA CH 292641 A CH292641 A CH 292641A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- preparation
- acid derivative
- mol
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical class OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical class OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 5
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 3
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 3
- 239000004571 lime Substances 0.000 claims description 3
- 239000000344 soap Substances 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- -1 copper complex salt Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Iminodiearbonsäurederivates. Es wurde gefunden, dass man zu einem netten Derivat der Iminodiessigsäure gelangt, wenn man 1 Mol 2,4-Dichlorphenol, 1 Mol Formaldehyd und 1 Mol Iminodiessigsäure miteinander umsetzt. Die Kondensation wird vorteilhaft in wässeriger alkalischer Lösung bei erhöhter Temperatur, z. B. 60 bis 70 , aus geführt. Das Natriumsalz des neuen Konden sationsproduktes ist wasserlöslich und kann zur Auflösung von Kalkseifen benützt wer den.
<I>Beispiel:</I> Zu einer Lösung von 4,9 Teilen 2,4-Di- ehlorphenol in 5 Teilen Wasser und 3 Vol-um- teilen 30%iger Natronlauge wird zuerst eine Lösung von 4,0 Teilen Iminodiessigsäure in 5 Teilen Wasser und 4 Volumteilen 30%iger Natronlauge und hierauf 2,
7 Teile einer 37 % igen Formaldehy dlösung unter Rühren zugegeben, worauf sieh das anfangs ausge schIedene ()1 langsam wieder löst. Nach ein- stüncligem Erwärmen auf 60 bis 70 C ist die Reaktion beendigt. Die mit. Wasser verdünnte, sehwach trübe Lösung wird mit Blutkohle ver setzt, filtriert und im Vakuum eingedampft. plan erhält 10,5 Teile eines weissen, festen Produktes, das in Wasser leicht löslich ist.
Während die wässerige Lösung nach Zusatz von Essigsäure klar bleibt, fällt mit Salzsäure die in Wasser schwer lösliche Säure harzartig aus und löst sieh wieder im Übersehuss Salz säure. Das Produkt entspricht der Formel
EMI0001.0039
Die zur Lösung der im Hauptpatent an geführten Kalkseifendispersion nötige Menge einer Lösung, welche in 100 cm3 2 g dieses Produktes enthält, beträgt 25 cm3. Das erhal tene Produkt gibt mit einer Lösung von Kup feracetat ein gelblichgrünes Kupferkomplex salz, das in Wasser löslich ist. Aus der wäs serigen Lösung desselben kann das Kupfer mit Soda nicht mehr gefällt werden.
Process for the preparation of a new iminodiearboxylic acid derivative. It has been found that a nice derivative of iminodiacetic acid is obtained if 1 mol of 2,4-dichlorophenol, 1 mol of formaldehyde and 1 mol of iminodiacetic acid are reacted with one another. The condensation is advantageously carried out in an aqueous alkaline solution at an elevated temperature, e.g. B. 60 to 70 out. The sodium salt of the new condensation product is water-soluble and can be used to dissolve lime soaps.
<I> Example: </I> To a solution of 4.9 parts of 2,4-dichlorophenol in 5 parts of water and 3 parts by volume of 30% strength sodium hydroxide solution, a solution of 4.0 parts of iminodiacetic acid in 5 parts of water and 4 parts by volume of 30% sodium hydroxide solution and then 2,
7 parts of a 37% formaldehyde solution are added with stirring, whereupon the initially separated () 1 slowly dissolves again. After one hour of heating to 60 to 70 C, the reaction is complete. With. Water-diluted, visibly cloudy solution is ver with blood charcoal, filtered and evaporated in vacuo. plan contains 10.5 parts of a white, solid product that is easily soluble in water.
While the aqueous solution remains clear after the addition of acetic acid, with hydrochloric acid the acid, which is sparingly soluble in water, precipitates like resin and dissolves again in the excess hydrochloric acid. The product conforms to the formula
EMI0001.0039
The amount of a solution required to dissolve the lime soap dispersion mentioned in the main patent, which contains 2 g of this product in 100 cm3, is 25 cm3. The product obtained is a yellowish green copper complex salt with a solution of Kup feracetat, which is soluble in water. From the aqueous solution of the same, the copper can no longer be precipitated with soda.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292641T | 1950-06-16 | ||
| CH1045800X | 1950-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH292641A true CH292641A (en) | 1953-08-15 |
Family
ID=25733292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH292641D CH292641A (en) | 1950-06-16 | 1950-06-16 | Process for the preparation of a new iminodicarboxylic acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH292641A (en) |
-
1950
- 1950-06-16 CH CH292641D patent/CH292641A/en unknown
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