Hydroquinone → Malathion

HRID 1851864

Reaction equation

HRID 1851864 reaction equation
[CH3:1][O:2][P:3](=[S:7])([O:5][CH3:6])[SH:4].[C:8]([O:17][CH2:18][CH3:19])(=[O:16])/[CH:9]=[CH:10]\[C:11]([O:13][CH2:14][CH3:15])=[O:12].C1(C=CC(O)=CC=1)O>>[CH3:19][CH2:18][O:17][C:8]([CH2:9][CH:10]([S:7][P:3]([O:5][CH3:6])([O:2][CH3:1])=[S:4])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:16]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 12959O,O-dimethyl phosphorodithioate2×HCID 5271566Diethyl Maleate2×

Product 1

HCID 4004Malathion

Procedure

The solution of dimethyl dithiophosphoric acid was added to diethyl maleate (the ratio of dimethyl dithiophosphoric acid to diethyl maleate was approximately 1-1.25 kg:1.2 kg). Hydroquinone (approximately 3 grams) was added to the mixture. The reaction mixture which contains two separate solutions, an organic solution of diethyl maleate and an aqueous solution of dimethyl dithiophosphoric acid, was mixed for about 8 hours at 53° C. under a nitrogen atmosphere. After mixing, the reaction was cooled to ambient temperature and the organic and aqueous solutions were separated. The organic or diethyl maleate solutions which contained malathion was washed two (2) times with water (approximately 1 liter each time). The organic and aqueous solutions were separated and the malathion in the solution of diethyl maleate retained. This reaction yielded approximately 1.5-1.9 kg of malathion.

Workup

  1. customseparate solutions
  2. additionan organic solution of diethyl maleate and an aqueous solution of dimethyl dithiophosphoric acid, was mixed for about 8 hours at 53° C. under a nitrogen atmosphere
  3. additionAfter mixing
  4. customthe organic and aqueous solutions were separated
  5. washwas washed two (2) times with water (approximately 1 liter each time)
  6. customThe organic and aqueous solutions were separated

Sources & evidence

ORD record
ord-fa38e77632e546429f7422f77ff12dfb
Source dataset
uspto-grants-2015_02
Patent number
US08957238B2

Linked notes

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