Sulfuric Acid → HCID 86587967, compound

HRID 1794981Notes

Reaction equation

HRID 1794981 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[S:13](=[O:17])(=[O:16])([OH:15])O>OS(O)(=O)=O.O=S(=O)=O>[N:1]1[CH:6]=[CH:5][C:4]([S:13]([OH:15])(=[O:17])=[O:16])=[C:3]([S:13]([OH:17])(=[O:16])=[O:15])[C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 14742,2'-Bipyridine

Product 1

HCID 86587967HCID 86587967, compound

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent2×

Conditions

Temperature
20 °C

Procedure

2 g of 2,2′Bipyridine was charged into a reactor, and 20 cc of concentrated sulfuric acid was added to it. This mixture was stirred until the amine dissolved. 20 cc of oleum 65% was added to this mixture under rapid stirring, and the reactor was cooled to about 20° C. After the solution of oleum, the reactants and contents were heated to 50° C. and maintained at this temperature for 48 hours. The reactor and its contents were cooled, and distilled water (10 cc) was added to the reaction mixture to quench the oleum. 50% NaOH solution was added to this solution, under cooling (10° C.) until the sulfuric acid solution was neutralized. The solution was concentrated and then methanol was added to extract the water-soluble ligand from the sodium sulfate powder. The methanol was evaporated to yield the water-soluble sodium salt of 2,2′bipyridine di sulfonic acid. [1.2 g] The product consists of mixtures of the bis sulfonation products as indicated by elemental analysis and 1h NMR. These can be used as such in synthesis of metal complexes for catalysis.

Workup

  1. dissolutiondissolved
  2. temperaturemaintained at this temperature for 48 hours
  3. temperatureThe reactor and its contents were cooled
  4. distillationdistilled water (10 cc)
  5. additionwas added to the reaction mixture
  6. customto quench the oleum
  7. addition50% NaOH solution was added to this solution
  8. temperatureunder cooling (10° C.) until the sulfuric acid solution
  9. concentrationThe solution was concentrated
  10. additionmethanol was added
  11. extractionto extract the water-soluble ligand from the sodium sulfate powder
  12. customThe methanol was evaporated

Sources & evidence

ORD record
ord-7426cb49f9df4615b784299e6098edfe
Source dataset
uspto-grants-2006_04
Patent number
US07026266B2

Reaction notes

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