Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Diphenyl carbonate | HCID 7597 | — |
| Reactant | Toluene 2,4-Diisocyanate | HCID 11443 | — |
| Reactant | Phenyl formate | HCID 74626 | — |
| Catalyst | Toluene 2,4-Diisocyanate | HCID 11443 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Phenol | HCID 996 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2,4-Diaminotoluene | HCID 7261 | — |
| Product | Phenyl carbamate | HCID 69322 | 79.9% |
Reaction Steps
The di-formamide of 2,4-toluene diamine is prepared by either reaction of the diamine with formic acid, with azeotropic removal of water with refluxing toluene, or by reaction of the diamine with phenyl formate in phenol. As in Example 1 above, the di-formamide (5.46 grams, 0.0307 mole) in phenol (17.50 grams, 0.186 mole) is added dropwise to diphenyl carbonate (26.40 grams, 0.123 mole) and heated to 232° C. at 110 mmHg. IS/GC analysis of the overhead (30.55 grams) and pot material (17.42 grams) shows the recovery of 4.004 grams of free 2,4-TDI and 0.277 grams of 2,4-TDI as phenol carbamate (0.0246 moles total TDI, 79.9% yield, based on di-formamide fed).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06781010B1 |
|---|
| Source dataset | uspto-grants-2004_08 |
|---|
| ORD ID | ord-dcc672b21c1349f0831b7e392cdd816f |
|---|
| Source note | uspto-grants-2004_08 |
|---|
