Ethylene Glycol → Tetrachlorophthalic acid

HRID 1995184Notes

Reaction equation

HRID 1995184 reaction equation
[OH-].[Na+].C(O)C[OH:5].[Cl:7][C:8]1[C:9]([Cl:21])=[C:10]([Cl:20])[C:11]([Cl:19])=[C:12]2[C:17](=[O:18])[O:16][C:14](=[O:15])[C:13]=12>O>[Cl:7][C:8]1[C:9]([Cl:21])=[C:10]([Cl:20])[C:11]([Cl:19])=[C:12]([C:17]([OH:16])=[O:18])[C:13]=1[C:14]([OH:5])=[O:15]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 8326Tetrachlorophthalic anhydrideHCID 14798Sodium Hydroxide3×

Product 1

HCID 12442Tetrachlorophthalic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 20 g quantity of sodium hydroxide was dissolved in 1000 g of water, and 200 g of ethylene glycol was added to the solution. Subsequently, 143 g of tetrachlorophthalic anhydride was added to the mixture, and the resulting mixture was heated to 95° to 98° C. to obtain a solution. A 122.5 g quantity of 40% aqueous solution of Cr2 (SO4)3 was diluted with 200 g of water and then added dropwise to the obtained solution at the same temperature, over a period of 40 minutes. The resulting mixture was thereafter stirred for 20 minutes, and provided a grayish green precipitate. Subsequently, 10% aqueous solution of sodium hydroxide was added dropwise to the reaction mixture to adjust the pH thereof to about 3. About 13 g of sodium hydroxide was so used. The mixture was further stirred for 2 hours, then cooled and filtered at about 50° C. The resulting reaction product was washed with water and dried, giving 140 g of Cr complex compound of tetrachlorophthalic acid. This complex compound was found to have good thermal stability (as tested at temperatures of below 350° C. in the same manner as described in Example 1).

Workup

  1. temperaturethe resulting mixture was heated to 95° to 98° C.
  2. customto obtain a solution
  3. additionadded dropwise to the obtained solution at the same temperature, over a period of 40 minutes
  4. customprovided a grayish green precipitate
  5. stirringThe mixture was further stirred for 2 hours
  6. temperaturecooled
  7. filtrationfiltered at about 50° C
  8. customThe resulting reaction product
  9. washwas washed with water
  10. customdried

Sources & evidence

ORD record
ord-85829846466b4bd3982fcd35e373feee
Source dataset
uspto-grants-1983_09
Patent number
US04403027

Reaction notes

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