DE109663C - - Google Patents
Info
- Publication number
- DE109663C DE109663C DE1898109663D DE109663DA DE109663C DE 109663 C DE109663 C DE 109663C DE 1898109663 D DE1898109663 D DE 1898109663D DE 109663D A DE109663D A DE 109663DA DE 109663 C DE109663 C DE 109663C
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- nitroethylbenzene
- methylene group
- bodies
- ether
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 12: Chemische Verfahren und Apparate.CLASS 12: Chemical processes and apparatus.
Zusatz zum Patente 107095 vom 2. September 1898.Addendum to patent 107095 of September 2, 1898.
Patentirt im Deutschen Reiche vom 16. Dezember 1898 ab. Längste Dauer: 1. September 1913.Patented in the German Empire on December 16, 1898. Longest duration: September 1, 1913.
In dem Patent 107095 wurde gezeigt, dafs aromatische Nitrokörper, die in o- oder p-Stellung zur Nitrogruppe ein Methyl enthalten, mit Salpetrigsäureestern zu Oximen von Nitroaldehyden condensirt werden können.In the patent 107095 it was shown that aromatic nitro bodies which are in the o- or p-position to the nitro group contain a methyl, with nitrous acid esters to oximes of nitroaldehydes can be condensed.
Es wurde.nun gefunden, dafs diese Reaction auch bei solchen Nitrokörpern eintritt, welche an Stelle der Methylgruppe eine nicht mit einem negativen Radical verbundene Methylengruppe enthalten. Die Bildung von Isonitrosoverbindungen bei der Einwirkung von Natriumä'thylat und Amylnitrit auf aromatische Verbindungen, welche eine Methylengruppe enthalten, ist bereits von verschiedenen Seiten beobachtet worden (Ann. 250. 163, Ann. 291. 280); stets aber waren die in den Bereich der Untersuchung gezogenen Verbindungen solche, welche eine mit einem negativen Radical verbundene Methylengruppe enthielten. Die Beobachtung, dafs die Nitroderivate von aromatischen Körpern mit einer Methylengruppe ohne ein benachbartes negatives Radical im Sinne des durch Patent 107095 geschützten Verfahrens reagiren, ist also neu.It has now been found that this reaction also occurs in nitro bodies which instead of the methyl group, a methylene group that is not linked to a negative radical contain. The formation of isonitroso compounds when exposed to sodium ethylate and amyl nitrite on aromatic compounds containing a methylene group, has already been observed from different sides (Ann. 250, 163, Ann. 291. 280); but the connections drawn into the area of investigation were always those which contained a methylene group linked to a negative radical. The observation, that the nitro derivatives of aromatic bodies with a methylene group without an adjacent negative radical in the sense of the process protected by patent 107095 is therefore new.
^CH2 ■ CH3
\2V0, ^ CH 2 ■ CH 3
\ 2V0,
Zu einer Lösung von 5 Theilen Natrium in 100 Theilen absolutem Alkohol giebt man unter Abkühlung ein Gemisch von 30,2 Theilen o-Nitroäthylbenzol und 23,4 Theilen Amylnitrit. Der Beginn der Reaction giebt sich durch den Eintritt einer intensiv gelben Färbung zu erkennen. Nach 12 stündigem Stehen bei gewöhnlicher Temperatur giebt man die Reactionsmasse in Wasser, entfernt das unveränderte Nitroäthylbenzol und scheidet durch Einleiten von Kohlensäure das entstandene ο - Ni tr ο acetophenonoxim aus der alkalischen Lösung aus. Es krystallisirt aus heifsem verdünntem Alkohol in feinen Nädelchen vom Schrnp. 11 5 °.To a solution of 5 parts of sodium in 100 parts of absolute alcohol is added while cooling, a mixture of 30.2 parts of o-nitroethylbenzene and 23.4 parts of amyl nitrite. The beginning of the reaction is indicated by the appearance of an intense yellow color. After standing for 12 hours at ordinary temperature, the reaction mass is added in water, removes the unchanged nitroethylbenzene and separates by introducing it of carbonic acid the resulting ο - Ni tr ο acetophenone oxime from the alkaline solution. It crystallizes from hot, diluted alcohol in fine needles from the Snippet 11 5 °.
Es ist leicht löslich in Alkohol, Aether und Benzol, schwer löslich in Ligrom. In Aetzalkalien löst es . sich mit gelber Farbe und wird durch Säuren oder Kohlendioxyd aus dieser Lösung ausgeschieden.It is easily soluble in alcohol, ether and benzene, hardly soluble in ligrom. In caustic alkalis solves it. turns yellow in color and is eliminated from this solution by acids or carbon dioxide.
Die Reaction verläuft nach folgender Gleichung: The reaction proceeds according to the following equation:
^N-ONa^ N-ONa
+ R-ON: 0 + RONa = C11H1(^CH3 + 2 R O H. + R-ON: 0 + RONa = C 11 H 1 (^ CH 3 + 2 RO H.
4\4 \
NO,NO,
Ersetzt man das ο - Nitroäthylbenzol durch m -p'-Dinitrodiphenylmethan, so erhält man das m-p'-Dinitrobenzophenonoxim:If the ο -nitroethylbenzene is replaced by m -p'-dinitrodiphenylmethane, one obtains the m-p'-dinitrobenzophenone oxime:
NO*NO *
CH2 +R-ON: O + RONaCH 2 + R-ON: O + RONa
NO,NO,
= C: = C:
NO,NO,
NO Na + 2R-OHNO Na + 2R-OH
NO„NO "
Das so erhaltene m-p'-Dinitrobenzophenonoxim krystallisirt aus Benzolligro'in in Primen vom Scbmp. 130 bis 1350· Es erwies sich identisch mit dem aus m-p'-Dinitrobenzophenon und Hydroxylamin erhaltenen Oxim.The m-p'-dinitrobenzophenone oxime thus obtained crystallizes from benzoligro'in in primes from Scbmp. 130 to 135 0 · It was found to be identical to the oxime obtained from m-p'-dinitrobenzophenone and hydroxylamine.
Aus p-Nitrobenzylphenylä"ther erhält man eine Phenyl-p-nitrobenzenylhydroxamsäure: A phenyl-p-nitrobenzenylhydroxamic acid is obtained from p-nitrobenzylphenyl ether:
NO,NO,
NO2 NO 2
+ RON: O + RONa = C: N O Na + 2ROH+ RON: O + RONa = C: NO Na + 2ROH
C,C,
Sie krystallisirt aus Benzolligroi'n in Nadeln vom Schmp. io8°. In Aetzalkalien ist sie mit gelber Farbe löslich und wird durch Kohlendioxyd aus dieser Lösung gefällt.It crystallizes from benzene in needles of mp 10 °. In caustic alkalis she is with yellow color and is precipitated from this solution by carbon dioxide.
Die neuen Verbindungen sollen zur Darstellung von Ketonen, ζ. B. o-Nitroacetophenon, dienen.The new compounds are intended to represent ketones, ζ. B. o-nitroacetophenone, to serve.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE107095T | 1898-09-02 | ||
| DE109663T | 1898-12-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE109663C true DE109663C (en) | 1900-02-27 |
Family
ID=379536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1898109663D Expired DE109663C (en) | 1898-09-02 | 1898-12-16 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE109663C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3117995A (en) * | 1960-02-11 | 1964-01-14 | Rumanian Ministry For Petroleu | Method of preparing p-nitroacetophenone and its oxime |
| US5120208A (en) * | 1990-10-18 | 1992-06-09 | Hitachi Koki Company Limited | Molecular drag pump with rotors moving in same direction |
-
1898
- 1898-12-16 DE DE1898109663D patent/DE109663C/de not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3117995A (en) * | 1960-02-11 | 1964-01-14 | Rumanian Ministry For Petroleu | Method of preparing p-nitroacetophenone and its oxime |
| US5120208A (en) * | 1990-10-18 | 1992-06-09 | Hitachi Koki Company Limited | Molecular drag pump with rotors moving in same direction |
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