Nitric Acid → Pendimethalin

HRID 1075712

Reaktionsgleichung

Reaktionsgleichung von HRID 1075712
C(C(NC1C=CC(C)=C(C)C=1)CC)C.[N+]([O-])(O)=O.N([O-])=O.[Na+].N([N:25]([CH:40]([CH2:43][CH3:44])[CH2:41][CH3:42])[C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][C:29]([CH3:35])=[C:28]([CH3:36])[C:27]=1[N+:37]([O-:39])=[O:38])=O.[N+](N(C(CC)CC)C1CC([N+]([O-])=O)(C)C(C)=CC=1[N+]([O-])=O)([O-])=O>ClC(Cl)C.O>[CH2:41]([CH:40]([NH:25][C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][C:29]([CH3:35])=[C:28]([CH3:36])[C:27]=1[N+:37]([O-:39])=[O:38])[CH2:43][CH3:44])[CH3:42]

Komponenten

8

Edukt 5

HCID 944Nitric AcidHCID 50260Nitroso-pendimethalinHCID 91984N-(1-ethylpropyl)-3,4-dimethylaniline2×HCID 23668193Sodium NitriteHCID 86754080N-nitro-N-(1-ethylpropyl)-3,6-dinitro-3,4-dimethyl-benzenamine

Produkt 1

HCID 38479Pendimethalin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

The dinitration of N-(1-ethylpropyl)-3,4-dimethyl-benzenamine is carried out in a pilot plant in a tubular reactor having a static mixer; the tubular reactor is constituted by a coil in three joined sections, each 5000 mm in length with an internal diameter of 4 mm, with temperature sensors fitted at the junctions between them. The Kenics Static Mixer is a 190 mm long tubular body inserted between the second and third sections. The reactor is immersed in a water-cooled thermostated bath. 67% nitric acid supplemented with 5000 ppm by weight of NaNO2 is fed to the reactor at a rate of 15 l/h at the same time as a solution of 39% by weight N-(1-ethylpropyl)-3,4-dimethyl-benzenamine in dichloroethane; this solution is fed at a rate of 21 l/h. After a period of 15 minutes, during which time the system reaches operating conditions, approximately 6 kg of reaction mass was collected in a separator. After phase separation of the acid phase from the organic phase, this latter which--leaving aside the solvent--is composed of 95% by weight dinitration products and contains 6.8% by weight N-nitroso-N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethyl-benzenamine and 54 ppm p/p N-nitro-N-(1-ethylpropyl)-3,6-dinitro-3,4-dimethyl-benzenamine, is washed and subjected to denitrosation by treatment with aqueous hydrobromic acid and sulphamic acid to transform its N-nitroso derivative co-produced in the course of the reaction into N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethyl-benzenamine. Once the solvent is evaporated, 1.78 kg of crude N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethyl-benzenamine were obtained with a titre of 94.2%.

Aufarbeitung

  1. customeach 5000 mm in length with an internal diameter of 4 mm, with temperature sensors fitted at the junctions between them
  2. temperaturecooled thermostated bath
  3. customconditions, approximately 6 kg of reaction mass
  4. customwas collected in a separator
  5. customAfter phase separation of the acid phase from the organic phase
  6. customthis latter which--leaving aside the solvent
  7. washis washed
  8. customin the course of the reaction into N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethyl-benzenamine
  9. customOnce the solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2760de2a49c746f1b4d5a3f76d02ea71
Quelldatensatz
uspto-grants-1999_05
Patentnummer
US05907062

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