1-Chloro-2,4-Dinitrobenzene → 2,4-Dinitrophenol

HRID 1719649

Reaktionsgleichung

Reaktionsgleichung von HRID 1719649
[N+](C1C=C([N+]([O-])=O)C=CC=1[Cl:13])([O-])=O.[N+:14]([C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[OH:26])([O-:16])=[O:15].[N+](COCCOC1C=CC(OC[N+]([O-])=O)=CC=1)([O-])=O.[OH-].[Na+].Cl.[Na].C=O.C1(S(O)(=O)=O)C2C(=CC=CC=2)C=CC=1.I(Cl)(Cl)Cl.ClCl.Cl[O-].[Na+]>[Fe](Cl)(Cl)Cl.O>[Cl:13][C:19]1[C:18]([OH:26])=[C:17]([N+:14]([O-:16])=[O:15])[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=1.[N+:14]([C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[OH:26])([O-:16])=[O:15]

Komponenten

14

Edukt 10

HCID 61-Chloro-2,4-DinitrobenzeneHCID 313Hydrochloric Acid3×HCID 14932,4-Dinitrophenol2×HCID 14798Sodium HydroxideHCID 24526Chlorine3×HCID 70076Iodine trichlorideHCID 5360545SodiumHCID 23665760Sodium HypochloriteHCID 57351120Morwet D 425HCID 1317143252,4-Dinitromethoxyethoxybenzene

Produkt 2

HCID 14932,4-DinitrophenolAusbeute 0,5 %HCID 136812-Chloro-4,6-dinitrophenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24380Iron chloride (FeCl3)KatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 183 parts of 2,4-dinitrochlorobenzene, 16 parts of 2,4-dinitrophenol and 3 parts of 2,4-dinitromethoxyethoxybenzene is saponified to 2,4-dinitrophenol in a mixture of 303 parts of 33% strength sodium hydroxide solution and 3,000 parts of water at 95° C. under an atmosphere of air. The resulting suspension i adjusted to a pH value of 3.5 by adding 185 parts of 31% strength hydrochloric acid. After 10 parts of the sodium salt of a naphthalenesulfonic acid formaldehyde condensation product (dispersing agent), 1 part of iron(III) chloride and 1 part of iodine trichloride have been added, 650 parts of 13 percent strength by weight chlorine bleach liquor (containing 150 g of active chlorine per liter) are added dropwise at 10° C. in the course of 8 hours, the pH increasing meanwhile. In the course of the addition, the pH reaches a value of 4.5. After it has reached this value, the pH is caused to remain, during the chlorination, within the range 4-4.5 by the simultaneous addition of 36 parts of 31% strength hydrochloric acid during the dropwise addition of the remainder of the chlorine bleach liquor. The pH of the suspension is then adjusted to a value of 1.0 by means of 170 parts of 31% strength hydrochloric acid, and small amounts of sodium hypochlorite still present are destroyed by means of 15 parts of 40% strength sodium bisulfite solution. The resulting product is then isolated by being filtered off at about 10° C. 200 parts of pale yellow 6-chloro-2,4-dinitrophenol (melting point: 101°-109° C.), now only containing traces (0.5%) of 2,4-dinitrophenol, are obtained.

Aufarbeitung

  1. additionhave been added
  2. additionare added dropwise at 10° C. in the course of 8 hours
  3. temperaturethe pH increasing meanwhile
  4. additionIn the course of the addition
  5. customstill present are destroyed by means of 15 parts of 40% strength sodium bisulfite solution
  6. customThe resulting product is then isolated
  7. filtrationby being filtered off at about 10° C

Quellen und Nachweise

ORD-Eintrag
ord-e0c182c73ba14e1ab11a236d330032ee
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04540832

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