Oxygen → Disulfiram

HRID 991971

Reaction equation

HRID 991971 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].O=O.[C:8](=[S:10])=[S:9]>C([O-])(=O)C.[Mn+2].C([O-])(=O)C>[CH2:1]([N:3]([CH2:4][CH3:5])[C:8](=[S:10])[S:9][S:9][C:8](=[S:10])[N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH3:2]

Participants

5

Reactant 3

HCID 977Oxygen3×HCID 6348Carbon Disulfide2×HCID 8021Diethylamine

Product 1

HCID 3117Disulfiram

Reagents, catalysts & solvents 1

HCID 12525Manganous AcetateCatalyst

Conditions

Temperature
60 °C

Procedure

Diethylamine (150 g, 2.05 moles) and manganese acetate catalyst (30 mg, 0.12 mmole) were charged into a 1 liter reactor at room temperature. The reactor was evacuated to 0.6×105 Pa (0.6 bar) and carbon disulfide (87.5 g, 1.15 moles) was dosed in 20 min while increasing the temperature to 60° C. The reactor was pressurized to 3×105 (3 bar) with pure oxygen and the stirring speed was raised to 1400 rpm. Carbon disulfide dosing was started again at a dosing rate of 2 moles per mole oxygen reacted, i.e. 68.5 g (0.90 mole) in 280 min. The reaction was stopped when the oxygen flow fell below 1 ml/min. After removal of the reaction water formed by evaporation, 295 g of tetraethyl thiuram disulfide were obtained (yield: 97.2 wt %) with a purity of 96.7 wt % (as determine d by the H2S titration method).

Workup

  1. temperaturethe stirring speed was raised to 1400 rpm
  2. customreacted
  3. waiti.e. 68.5 g (0.90 mole) in 280 min
  4. customAfter removal of the reaction water
  5. customformed by evaporation

Sources & evidence

ORD record
ord-69b8fd587f8f4be093325da0805a0f3d
Source dataset
uspto-grants-2002_10
Patent number
US06465691B1

Linked notes

Loading…