CH200909A - Process for the preparation of a nitrogen-containing aromatic aldehyde. - Google Patents
Process for the preparation of a nitrogen-containing aromatic aldehyde.Info
- Publication number
- CH200909A CH200909A CH200909DA CH200909A CH 200909 A CH200909 A CH 200909A CH 200909D A CH200909D A CH 200909DA CH 200909 A CH200909 A CH 200909A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitrogen
- containing aromatic
- aromatic aldehyde
- preparation
- aldehyde
- Prior art date
Links
- -1 nitrogen-containing aromatic aldehyde Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 239000013078 crystal Substances 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 1
- WBMGILSHAZPPNW-UHFFFAOYSA-N 6-amino-1,4-bis(2-chloroethyl)cyclohexa-2,4-diene-1-carbaldehyde Chemical compound ClCCC1(C=O)C(C=C(C=C1)CCCl)N WBMGILSHAZPPNW-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DNRDOYZBRNVGGF-UHFFFAOYSA-N n-(2,2-dichloroethyl)aniline Chemical compound ClC(Cl)CNC1=CC=CC=C1 DNRDOYZBRNVGGF-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines stickstoffhaltigen aromatischen .Aldehyds. Gegenstand des vorliegenden Patentes ist ein VelTahren zur Herstellung eines stick- stoffhaltigen aromatischen Aldehyds.
Das Verfahren Ist dadurch gekennzeichnet, dass man N-Di-ohloräthyl-anilin, N-Methylform- anilid und Phosphorogychlorid aufeinander einwirken lässt und in dem so erhaltenen p-Dichloräthylaminobenzaldehyd durch Be- handlung mit einem den Sulfosäurerest abge benden Mittel das Chlor gegen
Sulfagruppen aus-tauscht. Das Dinatriumsalz .des so erhal- tenen p-Drsulfäthylaminobenzaldehyds. kri- stallisiert in. feinen farblosen Kristallen. Der Aldehyd soll zur Synthese von Farbstoffen u.<B>a.</B> dienen.
<I>Beispiel:</I> Zu 169 Gewichtsteilen Phosphoroxy- ehlorid gibt man bei 70 allmählich 91 Ge- w@ichIsteile N-Di-oxyäthyl-anilin und er wärmt das Gemisch noch einige Zeit auf 90 bis 100 .
Nach dem Abkühlen lässt man bei 10 bis 15 allmählich ein Gemisch von 135 Gewichtsteilen N-Methylformanilid und 15.1 Gewichtsteilen: Phosphorogychlorid zutropfen, erwärmt noch einige,Stunden auf 45 bis<B>50'</B> und trägt auf Eis aus.
Der entstandene p-Di-(chloräthyl)-aminobenzaldehyd scheidet sich als schwach gefärbtes <B>01</B> ab, welches nach kurzem Rühren zu feinen, praktisch reinen Kristallen erstarrt. Der Aldehyd kri- stallisiert aus Alkohol in derben; langen Prismen vom Schmelzpunkt 88,5 .
Der p-Dxchloräthylaminobenzaldehyd wird nun mit einer Cal. '30 % igen Sulfitlösung, welche 2 Mol Natriums@ulfit enthält, bei 180 bis 2,00' behandelt,
und man erhält .aus der schwach gefärbten klaren Lösung nach Ab- destillieren des @grössten Teils Wasser das ausserordentlich leicht lösliche Dinatriumsalz des p-Di-(sulfäthyl)-aminobenzaldehyds .
in fast farblosen Kristallen, welche durch Um kristallisieren aus ca. 6i5%ig.em Alkohol rein weiss sind. Der Aldehyd ist sehr leicht lös- lich in wässerigen Mitteln.
Process for the production of a nitrogen-containing aromatic aldehyde. The subject of the present patent is a process for the production of a nitrogen-containing aromatic aldehyde.
The process is characterized in that N-di-chloroethyl aniline, N-methylform anilide and phosphorogychloride are allowed to act on one another and the chlorine is counteracted in the p-dichloroethylaminobenzaldehyde obtained in this way by treatment with an agent which releases the sulfonic acid radical
Exchanges sulfa groups. The disodium salt of the p-Drsulfäthylaminobenzaldehyds thus obtained. Crystallized in fine colorless crystals. The aldehyde is said to be used for the synthesis of dyes, among other things.
<I> Example: </I> 91 parts by weight of N-dioxyethylaniline are gradually added to 169 parts by weight of phosphorus oxychloride at 70 and the mixture is warmed to 90 to 100 for a while.
After cooling, a mixture of 135 parts by weight of N-methylformanilide and 15.1 parts by weight of phosphorogychloride is gradually added dropwise at 10 to 15, heated for a few hours to 45 to 50 'and discharged onto ice.
The resulting p-di (chloroethyl) aminobenzaldehyde separates out as a weakly colored <B> 01 </B>, which solidifies to fine, practically pure crystals after brief stirring. The aldehyde crystallizes from alcohol in a rough; long prisms with a melting point of 88.5.
The p-Dxchloräthylaminobenzaldehyd is now with a Cal. '30% sulphite solution, which contains 2 moles of sodium sulphite, treated at 180 to 2.00',
and the extremely easily soluble disodium salt of p-di (sulfethyl) aminobenzaldehyde is obtained from the pale, clear solution after distilling off most of the water.
in almost colorless crystals, which are pure white due to recrystallization from approx. 6.5% alcohol. The aldehyde is very easily soluble in aqueous media.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200909X | 1935-04-12 | ||
| CH192574T | 1936-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200909A true CH200909A (en) | 1938-10-31 |
Family
ID=25722304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200909D CH200909A (en) | 1935-04-12 | 1936-04-02 | Process for the preparation of a nitrogen-containing aromatic aldehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200909A (en) |
-
1936
- 1936-04-02 CH CH200909D patent/CH200909A/en unknown
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