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Toluene diisocyanate



Toluene-2,4-diisocyanate
IUPAC name 2,4-diisocyanato-1-methyl-benzene
Other names Tolylene diisocyanate
Methyl phenylene diisocyanate
Identifiers
CAS number 86-91-9
RTECS number CZ6300000
SMILES c1(C)c(N=C=O)cc(N=C=O)cc1
Properties
Molecular formula C9H6N2O2
Molar mass 174.2 g/mol
Appearance Colorless to pale yellow, liquid
Density 1.214 g/cm3, liquid
Melting point

21.8 °C (295.0 K)

Boiling point

251 °C (524 K)

Solubility in water Reacts
Hazards
EU classification Very toxic (T+)
Carc. Cat. 3
NFPA 704
1
3
1
 
R-phrases R26, R36/37/38, R40,
R42/43, R52/53
S-phrases (S1/2), S23, S36/37, S45, S61
Flash point 127 °C
Related Compounds
Related isocyanates Methylene diphenyl diisocyanate
Naphthalene diisocyanate
Related compounds Polyurethane
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Toluene diisocyanate (TDI) is an aromatic diisocyanate. It is produced for reaction with polyols to form polyurethanes. It exists in two isomers, 2,4-TDI (CAS: 584-84-9) and 2,6-TDI (CAS: 91-08-7). 2,4-TDI is produced in the pure state, but TDI is often marketed as 80/20 and 65/35 mixtures of the 2,4 and 2,6 isomers respectively. It is a highly produced diisocyanate, accounting for 34.1% of the global isocyanate market in 2000, second only to MDI.[1]

Contents

Synthesis

There are six steps to the synthesis of pure 2,4-TDI:[1]

  • Nitration: Reaction of toluene with nitric acid and a catalyst to form dinitrotoluene
  • Hydrogenation: Reaction of the dinitrotoluene with hydrogen and a catalyst to form a mixture of isomers of toluene diamine (TDA)
  • Purification: Distillation of the TDA mixture to produce meta-TDA
  • Phosgenation: Reaction of the meta-TDA with phosgene to form a crude TDI mixture
  • Purification: Distillation of the crude TDI mixture to produce an 80:20 mixture of 2,4-TDI and 2,6-TDI, known as TDI (80/20)
  • Differentiation: Separation of the TDI (80/20) to produce pure 2,4-TDI and a 65:35 mixture of 2,4-TDI and 2,6-TDI, known as TDI (65/35)

Chemistry

Each of the isocyanate functional groups in TDI can react with a hydroxyl group to form a urethane linkage.

2,4-TDI is an asymmetrical molecule and thus has two isocyanate groups of different reactivity. 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.[1]

Hazards

Exposure to TDI and its vapors should be avoided. It is a well-documented causative agent of asthma.

See also

References

  1. ^ a b c Randall, David; Lee, Steve (2002). The Polyurethanes Book. New York: Wiley. ISBN 0-470-85041-8. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Toluene_diisocyanate". A list of authors is available in Wikipedia.
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