Ethanol → Toluene 2,4-Diisocyanate

HRID 1659625Notes

Reaction equation

HRID 1659625 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:9].NC1C=C([N+]([O-])=O)C=CC=1C.N[C:22](N)=[O:23].[C]=O.[CH2:27]([OH:29])C>Cl[Pd]Cl>[N:1]([C:2]1[CH:7]=[C:6]([N:8]=[C:22]=[O:23])[CH:5]=[CH:4][C:3]=1[CH3:9])=[C:27]=[O:29]

Participants

7

Reactant 5

HCID 702EthanolHCID 1176Urea2×HCID 72612,4-DiaminotolueneHCID 74442-Methyl-5-NitroanilineHCID 178418416HCID 178418416, compound

Product 1

HCID 11443Toluene 2,4-Diisocyanate

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

250 g of the following mixture were introduced into a 0.7 liter autoclave: 2×10-3 % by weight of PdCl2, 4% by weight of FeOCl, 14.8% by weight of a bis-urea of 2,4-diamino toluene and 2-amino-4-nitrotoluene and 81% by weight of ethanol. The nitro groups of the urea used are oxidizing agents for the oxycarbonylation of the urea function. 120 bar of carbon monoxide were forced in at room temperature. The mixture was allowed to react for two hours at 180° C. The bis-urea was converted quantitatively. The bis-urethane of 2,4-diisocyanatotoluene was obtained with a selectivity of 50 mol % in addition to 10 mol % of isomeric aminourethanes.

Workup

  1. customwere forced in at room temperature
  2. customto react for two hours at 180° C

Sources & evidence

ORD record
ord-6aa5440d67bb4c6180faee262f866adb
Source dataset
uspto-grants-1981_12
Patent number
US04304922

Reaction notes

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