Toluene diisocyanates

Data were last reviewed in lARC (1986) and the compounds were classified in lARC Monographs Supplement 7 (1987). 

2 Structural and molecular formulae and relative molecular mass 

Description Colourless to pale yellow liquid with pungent odour (United States National Library of Medicine, 1997) 

Solubility 2,4- and 2,6-Toluene diisocyanates decompose in water and are very soluble in acetone and benzene (Lide, 1997) 

Worldwide production capacities for toluene diisocyanates in 1987 were reported as (thousand tonnes) western hemisphere, 356 eastern Europe, 46 western Europe, 380 and Japan and the Far East, 88 (Ulrich, 1989). Worldwide production capacities in 1993 were reported as (thousand tonnes) North America, 485 Europe, 530 Pacific region, 308 and Latin America, 102.5 (Anon., 1995). 

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Phosgene (for toluene diisocyanate, dipbenylmetbane diisocyanate, and polycarbonate resin manufacture), cbloroisocyanuric acid, cyanuric cbloride. 

These foams are produced from long-chain, Hghtiy branched polyols reacting with a diisocyanate, usuaUy toluene diisocyanate [1321 -38-6] (TDI), to form an open-ceUed stmcture with free air dow during dexure. During manufacture these foams are closely controUed for proper density, ranging from 13 to 80 kg/m (0.8—5 lbs/ft ), to achieve the desired physical properties and cost. 

For methylene diphenyl diisocyanate (MDI), the initial reaction involves the condensation of aniline [62-53-3] (21) with formaldehyde [50-00-0] to yield a mixture of oligomeric amines (22, where n = 1, 2, 3...). For toluene diisocyanate, amine monomers are prepared by the nitration (qv) of toluene [108-88-3] and subsequent hydrogenation (see Amines byreduction). These materials are converted to the isocyanate, in the majority of the commercial aromatic isocyanate phosgenation processes, using a two-step approach. 

A convenient method for the synthesis of these low boiling materials consists of the reaction of /V,/V-dimethy1iirea [96-31-1] with toluene diisocyanate to yield an aUphatic—aromatic urea (84). Alternatively, an appropriate aUphatic—aromatic urea can be prepared by the reaction of diphenylcarbamoyl chloride [83-01-2] with methylamine. Thermolysis of either of the mixed ureas produces methyl isocyanate ia high yield (3,85). 

Phosgenation. The most important reaction of y -toluenediamine is with phosgene [75-44-5] to give toluene diisocyanate TDI (see... 

Yield for the process at low catalyst loading is 95%. AJ-Methyl-toluenediamiae, one of the reaction by-products, represents not only a reduction ia yield, but also a highly objectionable impurity ia the manufacture of toluene diisocyanate. Low concentrations of CO (0.3—6% volume) control this side reaction. 

Toluene Diisocyanate. Toluene diisocyanate is the basic raw material for production of flexible polyurethane foams. It is produced by the reaction sequence shown below, in which toluene is dinitrated, the dinitrotoluene is hydrogenated to yield 2,4-diaminotoluene, and this diamine in turn is treated with phosgene to yield toluene 2,4-diisocyanate. 

An equimolar mixture of carbon monoxide and chlorine reacts at 500 K under a slight positive pressure. The reaction is extremely exothermic (Ai/gQQp. = —109.7 kJ or —26.22 kcal), and heat removal is the limiting factor in reactor design. Phosgene (qv) is often produced on-site for use in the manufacture of toluene diisocyanate (see Amines, aromatic-diaminotoluenes Isocyanates, organic). 

Toluene diisocyanate Separation of TDI 80 into 22,000 Undisclosed Falling him Undisclosed Undisclosed... 

Toluene diisocyanate (toluene diamine, phosgene) B LG None 200-210 1 7h [7] 657... 

Toluene diisocyanate Midget impinger 15 ml Marcali solution 1 25 95 Diazotlzation and coupling reaction Materials containing reactive hydrogen attached to oxygen (phenol) certain other diamines... 

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