Tolylene-2,4-diisocyanate (TDI) is an organic compound with the formula
CH3C6H3(NCO)2. Two of the six possible isomers are commercially important:
2,4-TDI (CAS: 584-84-9) and
2,6-TDI (CAS: 91-08-7).
1.Synthesis
2,4-TDI is prepared in three steps from toluene, which is doubly nitrated
with nitric acid to give dinitrotoluene. This step determines the isomer ratio
of the ultimate TDI. Hydrogenation of the dinitrotoluene produces the
corresponding isomers of diaminotoluene (TDA). Finally, the TDA is subjected to
phosgenation, i.e. treatment with phosgene to form TDI. This final step produces
HCl as a byproduct and is a major source of industrial hydrochloric
acid.
2.application
The isocyanate functional groups in TDI react with a hydroxyl groups to form
urethane linkages. The two isocyanate groups in TDI react at different rates:
The 4-position is approximately four times more reactive than the 2-position.
2,6-TDI is a symmetrical molecule and thus has two isocyanate groups of similar
reactivity, similar to the 2-position on 2,4-TDI. However, since both isocyanate
groups are attached to the same aromatic ring, reaction of one isocyanate group
will cause a change in the reactivity of the second isocyanate group.
3.Hazard
The LD50 for TDI is 5800 mg/kg for oral contact and LC50 of 610 mg/m3 for the
vapour. Despite the indicated low toxicity, TDI is classified as “very toxic” by
the European Community.
Information is available on handling, personal protective equipment, exposure
monitoring, transport, storage, sampling and analysis of TDI, dealing with
accidents, and health and environmental themes. All major producers of TDI are
members of the International Isocyanate Institute, whose aim is the promotion of
the safe handling of TDI in the workplace, community, and environment.
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