CH297403A - Process for the preparation of a nitroaryl vinyl sulfone. - Google Patents
Process for the preparation of a nitroaryl vinyl sulfone.Info
- Publication number
- CH297403A CH297403A CH297403DA CH297403A CH 297403 A CH297403 A CH 297403A CH 297403D A CH297403D A CH 297403DA CH 297403 A CH297403 A CH 297403A
- Authority
- CH
- Switzerland
- Prior art keywords
- vinyl sulfone
- nitroaryl
- parts
- preparation
- vinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- -1 nitroaryl vinyl sulfone Chemical compound 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- NKCACQLHTNZVSX-UHFFFAOYSA-N 1-ethenylsulfonyl-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)C=C NKCACQLHTNZVSX-UHFFFAOYSA-N 0.000 claims description 5
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 125000003609 aryl vinyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- VKVLTUQLNXVANB-UHFFFAOYSA-N 1-ethenyl-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C=C VKVLTUQLNXVANB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Nitroaryl-vinylsuNons. Mononitroaryl - vinylsulfone sind bisher noch nicht bekannt. Es wurde nun gefunden, class man Mononitroaryl-vinylsulfone in guter bis sehr guter Ausbeute und hoher Reinheit auf technisch einfache Weise erhalten kann, wenn man auf Arylvinylsulfone der allge meinen Formel CHX-CX-SO2-R, worin R einen aromatischen Rest, beide X Wasserstoff oder ein X Halogen und das andere Wasserstoff bedeuten, nitrierende Mit tel einwirken lässt.
Die glatte Bildung im Kern nitrierter Arylvinylsulfone ist überraschend, da beispielsweise die Nitrierung von Vinyl- benzol kein Vinylnitrobenzol, sondern in der Hauptsache weitgehende Abbauprodukte lie fert (vergleiche A. 53, S. 297).
Gegenstand des Patentes ist ein Verfahren zur Herstellung eines Nitroaryl-v inylsulfons, das dadurch gekennzeichnet ist, dass man auf Phenylvinylsulfon nitrierende Mittel einwir ken lässt und das so gebildete Nitrophenyl- vinylsulfon isoliert.
Das so erhaltene neue Nitrophenylvinyl- sulfon bildet weisse Kristalle, schmilzt im reinen Zustand bei 108-109 , löst sich in kon zentrierter Schwefelsäure und ist in Wasser unlöslich.
Es lässt sich aus Tetrachlorkohlen- stoff oder Methanol umlösen. Aus der schwe felsauren Lösung wird die Verbindung durch Fällen mit Wasser unverändert 7urückerhal- ten. Es lässt sich zu Aminophenylvinylst-tlfon reduzieren und bildet ein wichtiges Zwischen produkt für die Herstellung von Farbstoffen, Polymerisationsprodukten und Textilhilfsmit teln.
<I>Beispiel 1:</I> 252 Gewichtsteile Phenylvinylsulfon wer den bei 5-10 in 750 Volumteile 100 /oiger Schwefelsäure eingerührt und gelöst. Dann lä.sst man bei der gleichen Temperatur eine Nitriersäure aus 95 Gewichtsteilen 100 /o iger Salpetersäure und 220 Gewichtsteilen konzen trierter Schwefelsäure langsam hinzufliessen. Nach kurzem Nachrühren wird das Reaktions gemisch auf Eiswasser gegossen, die ausge schiedene, fast farblose Verbindung abgesaugt und mit Wässer neutral gewaschen.
Das in einer Ausbeute von 304 Gewichtsteilen erhal tene Nitrophenylvinylsulfon der wahrschein lichen Formel:
EMI0001.0042
schmilzt nach dem LTmlösen aus Methanol bei 108-109 .
<I>Beispiel 2:</I> 16,8 Gewichtsteile Phenylvinylsulfon wer den bei etwa 20-25 in 75 Volumteile 100 /oiger Schwefelsäure eingerührt und so in ihr gelöst. Dann trägt man bei der gleichen Temperatur portionsweise 9-9,5 Gewichts teile pulverisiertes N atriumnitrat in die Lö sung ein und rührt bis zur vollständigen Auf lösung nach. Das Reaktionsgemisch wird auf Eiswasser gegossen und wie im Beispiel 1 be schrieben aufgearbeitet. Man erhält das Nitro- phenylvinylsulfon in einer Ausbeute von 20 Clewiehtsteilen.
Process for the preparation of a nitroaryl vinyl sulfone. Mononitroaryl vinyl sulfones are not yet known. It has now been found that mononitroaryl vinyl sulfones can be obtained in a technically simple manner in good to very good yield and high purity if one uses aryl vinyl sulfones of the general formula CHX-CX-SO2-R, where R is an aromatic radical, both X. Hydrogen or one X is halogen and the other is hydrogen, nitrating means can act.
The smooth formation in the core of nitrated aryl vinyl sulfones is surprising since, for example, the nitration of vinyl benzene does not produce vinyl nitrobenzene, but mainly produces extensive degradation products (see A. 53, p. 297).
The subject of the patent is a process for the production of a nitroaryl vinyl sulfone, which is characterized in that nitrating agents are allowed to act on phenyl vinyl sulfone and the nitrophenyl vinyl sulfone thus formed is isolated.
The new nitrophenyl vinyl sulfone thus obtained forms white crystals, melts in the pure state at 108-109, dissolves in concentrated sulfuric acid and is insoluble in water.
It can be converted from carbon tetrachloride or methanol. The compound is retained unchanged from the sulfuric acid solution by precipitation with water. It can be reduced to aminophenylvinylst-tlfon and forms an important intermediate for the manufacture of dyes, polymerisation products and textile auxiliaries.
<I> Example 1: </I> 252 parts by weight of phenyl vinyl sulfone are stirred into 750 parts by volume of 100% sulfuric acid at 5-10 and dissolved. Then, at the same temperature, a nitrating acid composed of 95 parts by weight of 100% nitric acid and 220 parts by weight of concentrated sulfuric acid is slowly added. After brief stirring, the reaction mixture is poured onto ice water, the separated, almost colorless compound is filtered off with suction and washed neutral with water.
The nitrophenyl vinyl sulfone of the probable formula obtained in a yield of 304 parts by weight:
EMI0001.0042
melts at 108-109 after dissolution from methanol.
<I> Example 2: </I> 16.8 parts by weight of phenylvinylsulfone are stirred into 75 parts by volume of 100% sulfuric acid at around 20-25 parts by volume and thus dissolved in it. Then, at the same temperature, 9-9.5 parts by weight of powdered sodium nitrate are added in portions to the solution and the mixture is stirred until it is completely dissolved. The reaction mixture is poured onto ice water and worked up as described in Example 1 be. The nitrophenyl vinyl sulfone is obtained in a yield of 20 parts by weight.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE297403X | 1942-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297403A true CH297403A (en) | 1954-03-31 |
Family
ID=6090672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297403D CH297403A (en) | 1942-01-29 | 1943-10-15 | Process for the preparation of a nitroaryl vinyl sulfone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH297403A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1210804B (en) * | 1961-07-22 | 1966-02-17 | Basf Ag | Process for the preparation of aryl vinyl sulfonic acid esters substituted by nitro groups in the aryl nucleus |
-
1943
- 1943-10-15 CH CH297403D patent/CH297403A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1210804B (en) * | 1961-07-22 | 1966-02-17 | Basf Ag | Process for the preparation of aryl vinyl sulfonic acid esters substituted by nitro groups in the aryl nucleus |
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