Glycerol → Benzanthrone

HRID 848432Notes

Reaction equation

HRID 848432 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[PH2]([O-])=O.[Na+].O.O[CH2:23][CH:24]([CH2:26]O)O>S(=O)(=O)(O)O>[CH:23]1[C:6]2=[C:7]3[C:12]([C:13]([C:14]4[C:5]2=[CH:4][CH:3]=[CH:2][CH:1]=4)=[O:15])=[CH:11][CH:10]=[CH:9][C:8]3=[CH:26][CH:24]=1

Participants

6

Reactant 4

HCID 753GlycerolHCID 962WaterHCID 6780AnthraquinoneHCID 178527019HCID 178527019, compound

Product 1

HCID 6697Benzanthrone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

Procedure

208 g of anthraquinone are dissolved in 1,000 g of concentrated sulphuric acid at 80°-110°. 96 g of sodium hypophosphite, dissolved in 240 g of glycerol, are added to this solution in a manner such that a temperature of 100° C. can be maintained. The mixture is then heated to 120° C. and kept at this temperature for 3 hours. The melt is then poured into 3 l of water and the product which has precipitated is filtered off. It is washed with hot water until the runnings are almost colourless, the filter cake is then suspended in 1.5 l of water and the suspension is rendered weakly alkaline and boiled up. After renewed filtration of the product, washing with hot water and drying at 100° C., 200-225 g of 92-97% pure benzanthrone≈80-93% of theory result.

Workup

  1. additionare added to this solution in a manner such that a temperature of 100° C.
  2. temperaturecan be maintained
  3. customthe product which has precipitated
  4. filtrationis filtered off
  5. washIt is washed with hot water until the runnings
  6. filtrationfiltration of the product
  7. washwashing with hot water
  8. customdrying at 100° C.

Sources & evidence

ORD record
ord-293cb5a5d92e4c3191987c4a86627b97
Source dataset
uspto-grants-1981_10
Patent number
US04296043

Reaction notes

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