Iodine → Benzylbenzene diisocyanate

HRID 45412Notes

Reaction equation

HRID 45412 reaction equation
[NH:1]([CH2:5][CH2:6]O)CCO.II.[C:10]1(=[O:16])O[C:13](=O)[CH:12]=[CH:11]1.S(=O)(=O)(O)O.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[N-:1]=[C:10]=[O:16].[N-:1]=[C:10]=[O:16].[C:22]1([CH2:28][C:6]2[CH:5]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 1140TolueneHCID 7923Maleic AnhydrideHCID 8113Diethanolamine

Product 1

HCID 19824838Benzylbenzene diisocyanate

Procedure

The above amounts of diethanolamine and iodine were added to the above amount of soybean oil with stirring. The mixture was stirred for 22 hours at a temperature between about 180° F. and about 225° F. Then, the above amounts of maleic anhydride, toluene and sulfuric acid were added with stirring. The mixture was refluxed for 6 hours using a Dean-Stark distilling trap, then distilled out of solvent to give a liquid soybean oil based polyol with a hydroxyl number of 50. A reaction mixture of about 10.00 grams of the polyol and the above indicated amount of diphenylmethane diisocyanate yielded a solid soybean oil based polyurethane material.

Workup

  1. stirringThe mixture was stirred for 22 hours at a temperature between about 180° F. and about 225° F
  2. stirringwith stirring
  3. temperatureThe mixture was refluxed for 6 hours
  4. distillationdistilling trap
  5. distillationdistilled out of solvent
  6. customto give a liquid soybean oil

Sources & evidence

ORD record
ord-c9d7d6f6638d4ab5bbe53189e49c85f8
Source dataset
uspto-grants-2013_09
Patent number
US08541536B2

Reaction notes

Loading…