Catechol → Niobium Catecholate

HRID 2093262Notes

Reaction equation

HRID 2093262 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[O-]CC.[Nb+5:12].[O-]CC.[O-]CC.[O-]CC.[O-]CC>C1(C)C=CC=CC=1>[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O-:4])[O-:2].[Nb+5:12].[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O-:4])[O-:2].[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O-:4])[O-:2].[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O-:4])[O-:2].[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O-:4])[O-:2].[Nb+5:12]

Participants

4

Reactant 2

HCID 289CatecholHCID 160675Ethanol, niobium(5+) salt (5:1)

Product 1

HCID 131730578Niobium Catecholate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of catechol (8.64 g, 78.5 mmol) and toluene (70 ml) was dehydrated by distilling 10 mL of the solution. Thereafter, 10.0 g (31.4 mmol) of niobium(V) ethoxide was added to the solution while stirring. The mixed solution was refluxed for 1 hour, and then, while the distillation temperature was 110° C. or higher, distilled until the amount of the solution became half. After the distillation, volatile components of the residual mixed solution were vaporized under reduced pressure by a rotary evaporator. The residual solid content was further heated to 100° C. under vacuum using a vacuum dryer so that the remaining volatile components were completely removed. The solid content (catechol-niobium complex) was brown in color. The yield amount was 11.4 g (31.4 mmol), and the yield percentage was 100%. 3.63 g of catechol-niobium complex was dissolved into 100 mL of 1:4 acetylacetone/toluene to produce a coating liquid.

Workup

  1. distillationby distilling 10 mL of the solution
  2. temperatureThe mixed solution was refluxed for 1 hour
  3. customwas 110° C.
  4. distillationhigher, distilled until the amount of the solution
  5. distillationAfter the distillation, volatile components of the residual mixed solution
  6. customwere vaporized under reduced pressure by a rotary evaporator
  7. customwere completely removed
  8. dissolution3.63 g of catechol-niobium complex was dissolved into 100 mL of 1:4 acetylacetone/toluene
  9. customto produce a coating liquid

Sources & evidence

ORD record
ord-8f6fe3d578cd4b46a5cd910280769a10
Source dataset
uspto-grants-2013_05
Patent number
US08445118B2

Reaction notes

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