Sulfuric Acid → 5-Nitrobenzene-1,2,3-tricarboxylic acid

HRID 66225

Reaction equation

HRID 66225 reaction equation
[C:1]1([C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=[O:8])[C:2]=1[C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[N+:21]([O-])([O-:23])=[O:22].[K+]>O>[N+:21]([C:5]1[CH:6]=[C:1]([C:13]([OH:15])=[O:14])[C:2]([C:10]([OH:12])=[O:11])=[C:3]([C:7]([OH:9])=[O:8])[CH:4]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 112881,2,3-Benzenetricarboxylic acidHCID 24434Potassium Nitrate

Product 1

HCID 144348595-Nitrobenzene-1,2,3-tricarboxylic acidYield 50.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 125 g of 1,2,3-benzenetricarboxylic acid and 900 ml of concentrated sulfuric acid at 60°-70° C. is added, gradually over a 2 hour period, 312 g of potassium nitrate. The mixture is heated at 135°-140° C. for 16 hours, cooled and treated with ice and water. Some solid is separated out and is dissolved in water. The entire aqueous mixture is extracted with ether, the extract is washed with water and dried over magnesium sulfate. The ether is concentrated to a small volume, and petroleum ether is added to precipitate a white solid. The solid is collected and dried to give 76.5 g of 5-nitro-1,2,3-benzenetricarboxylic acid.

Workup

  1. additionis added, gradually over a 2 hour period
  2. temperatureThe mixture is heated at 135°-140° C. for 16 hours
  3. temperaturecooled
  4. customSome solid is separated out
  5. dissolutionis dissolved in water
  6. extractionThe entire aqueous mixture is extracted with ether
  7. washthe extract is washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationThe ether is concentrated to a small volume, and petroleum ether
  10. additionis added
  11. customto precipitate a white solid
  12. customThe solid is collected
  13. customdried

Sources & evidence

ORD record
ord-3f603b5dc60b4c7bbc0a097e7b89eb59
Source dataset
uspto-grants-1978_12
Patent number
US04130660

Linked notes

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