Ethanol → Phthalate

HRID 976088

Reaction equation

HRID 976088 reaction equation
[Mg+2:1].[Cl-].[Cl-].C(O)C.[C:7]([O:22]CC(C)C)(=[O:21])[C:8]1[C:9](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:10]([O:12]CC(C)C)=[O:11]>CCCCCCC>[Mg:1].[C:7]([O-:22])(=[O:21])[C:8]1[C:9](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:10]([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 702EthanolHCID 6782Diisobutyl phthalateHCID 5360315Magnesium Chloride2×

Product 2

HCID 181977PhthalateHCID 5462224Magnesium

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
120 °C

Procedure

Into a stirred reactor 28.4 g of MgCl2, 49.5 g of anhydrous ethanol, 10 ml of vaseline oil ROL OB/30, 100 ml of silicone oil having a viscosity of 350 cs were added. The mixture was heated at 120° C. until MgCl2 was dissolved. The hot reaction mixture was then transferred to a 1.5 l reactor equipped with a Ultra Turrax T-45 N stirrer, containing 150 cm3 of vaseline oil and 150 cm3 of silicone oil. The temperature was maintained at 120° C. whilst stirring for 3 minutes at 3000 RPM. The mixture was then discharged in a 2 liter stirred tank containing 1 l of anhydrous n-heptane cooled to 0° C. whilst stirring at a speed of 6 m/sec for about 20 minutes, maintaining the temperature at 0° C. The particles so obtained, after washing with n-hexane, were subjected to a thermal treatment in a nitrogen stream, at temperatures ranging from 50° to 150° C. until spherical particles were obtained having a residual alcohol content of about 35% by weight. 25 g of this product were charged into a stirred reactor containing 625 ml of TlCl4 at 0° C. and under stirring. The mixture was then heated to 100° C. for one hour and then left to cool. When the temperature of 40° C. was reached, diisobutyl phthalate was added in quantities such to give a molar ratio of magnesium to phthalate of 8. The mixture was heated to 100° C. for 2 hours under stirring and then the solid was left to settle. The hot liquid was removed by syphoning. Then 500 ml of TiCl4 was added and the mixture was heated to 120° C. for 1 hour whilst stirring. After settling, the hot liquid was removed by syphoning and the solid was washed with n-hexane.

Workup

  1. dissolutionwas dissolved
  2. customThe hot reaction mixture was then transferred to a 1.5 l reactor
  3. customequipped with a Ultra Turrax T-45 N stirrer
  4. stirringstirred tank
  5. temperaturecooled to 0° C.
  6. stirringwhilst stirring at a speed of 6 m/sec for about 20 minutes
  7. temperaturemaintaining the temperature at 0° C
  8. customThe particles so obtained
  9. washafter washing with n-hexane
  10. customranging from 50° to 150° C. until spherical particles
  11. customwere obtained
  12. stirringunder stirring
  13. temperatureThe mixture was then heated to 100° C. for one hour
  14. waitleft
  15. temperatureto cool
  16. customthe temperature of 40° C.

Sources & evidence

ORD record
ord-e9de7fe43fa946559f90b78ff5ef40cc
Source dataset
uspto-grants-1997_03
Patent number
US05610244

Linked notes

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