Iodine → Benzylbenzene diisocyanate

HRID 45415Notes

Reaction equation

HRID 45415 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.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[N-:1]=[C:10]=[O:16].[N-:1]=[C:10]=[O:16].[C:17]1([CH2:27][C:6]2[CH:5]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 807IodineHCID 6101p-Toluenesulfonic acidHCID 7923Maleic AnhydrideHCID 8113Diethanolamine

Product 1

HCID 19824838Benzylbenzene diisocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 228° F. Then, the above amounts of maleic anhydride, toluene and p-toluenesulphonic acid were added with stirring. The mixture was refluxed for 10 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 54. 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 228° F
  2. stirringwith stirring
  3. temperatureThe mixture was refluxed for 10 hours
  4. distillationdistilling trap
  5. distillationdistilled out of solvent
  6. customto give a liquid soybean oil

Sources & evidence

ORD record
ord-2073206467494843b9a58b69b4b418bf
Source dataset
uspto-grants-2013_09
Patent number
US08541536B2

Reaction notes

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