Acetic Acid → Benzoic Acid

HRID 1165090

Reaktionsgleichung

Reaktionsgleichung von HRID 1165090
[N+]([C:4]1[CH:9]=[C:8](C)C=[CH:6][C:5]=1C)([O-])=O.Br.O=O.C1(C)C=CC=CC=1.[C:22]([OH:25])(=[O:24])[CH3:23]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.[Ti]>[C:22]([OH:25])(=[O:24])[C:23]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1

Komponenten

9

Edukt 5

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 977Oxygen2×HCID 1140Toluene2×HCID 6974Nitro-p-xylene

Produkt 1

HCID 243Benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23963TitaniumKatalysatorHCID 61372Cobalt(II) acetate tetrahydrateKatalysatorHCID 93021Manganese acetate tetrahydrateKatalysator

Versuchsvorschrift

2-Nitro-p-xylene (40 g), acetic acid (300 g), cobalt (II) acetate tetrahydrate (1.0 g), manganese (II) acetate tetrahydrate (1.0 g), zirconium (IV) diacetate oxide (0.13 g), and 48% hydrobromic acid (1.4 g) were charged into a stirred, one liter titanium autoclave. Oxidation was initiated at an initial temperature of 325° F. under a 250 psig nitrogen atmosphere by introducing 20.9 volume % oxygen into the reactor at a flow rate of 18 ft3 /hr. After the initial oxygen uptake had ceased, a solution consisting of toluene in acetic acid (0.7 g toluene per ml of solution) was added semi-continuously to the reactor via a single-headed Milton Roy pump at a flow rate of 2-2.5 ml/minute. Oxidation temperature was maintained at an average of 383° F. during the semi-continuous addition of toluene (0.87 moles), followed by a rapid temperature ramp to 415° F. and a pressure of 350 psig. Oxidation was terminated when the vent O2 had reached a steady 19 volume %. Analysis of the reaction products indicated that 2-nitroterephthalic acid was formed in a 74 mole % yield, while benzoic acid was formed in a 91 mole % yield. Toluene and 2-nitro-p-xylene were not detected.

Aufarbeitung

  1. customtemperature of 325° F.
  2. additionwas added semi-continuously to the reactor via a single-headed Milton Roy pump at a flow rate of 2-2.5 ml/minute
  3. customfollowed by a rapid temperature ramp to 415° F.
  4. customOxidation was terminated when the vent O2
  5. customwas formed in a 74 mole %

Quellen und Nachweise

ORD-Eintrag
ord-2e31111f306c4ff9aec99b7cdf120f7d
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04906771

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