Toluene diisocyanate

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Toluene-2,4-diisocyanate

Names

Preferred IUPAC name

2,4-Diisocyanato-1-methylbenzene

Other names

Tolylene diisocyanate

Methyl phenylene diisocyanate

 Identifiers

CAS Number  584-84-9

3D model (JSmol)  Interactive image

ChEBI  CHEBI:53556

ChEMBL  ChEMBL1086446

ChemSpider  13835351

ECHA InfoCard 100.008.678

RTECS number  CZ6300000

CompTox Dashboard (EPA)  DTXSID7026156

InChI[show]

SMILES[show]

Properties

Chemical formula C9H6N2O2

Molar mass 174.2 g/mol

Appearance Colorless liquid

Odor sharp, pungent[1]

Density 1.214 g/cm3, liquid

Melting point 21.8 °C (71.2 °F; 294.9 K)

Boiling point 251 °C (484 °F; 524 K)

Solubility in water Reacts

Vapor pressure 0.01 mmHg (25°C)[1]

Hazards

Safety data sheet See: data page

EU classification (DSD) (outdated) Very toxic (T+)

Carc. Cat. 3
R-phrases (outdated) R26, R36/37/38, R40,

R42/43, R52/53

S-phrases (outdated) (S1/2), S23, S36/37, S45, S61

NFPA 704 (fire diamond)

1
3
1
Flash point 127 °C (261 °F; 400 K)

Explosive limits 0.9%-9.5%[1]

Lethal dose or concentration (LD, LC):

LC50 (median concentration) 14 ppm (rat, 4 hr)

13.9 ppm (guinea pig, 4 hr)

9.7 ppm (mouse, 4 hr)

11 ppm (rabbit, 4 hr)[2]

NIOSH (US health exposure limits):

PEL (Permissible) C 0.02 ppm (0.14 mg/m3)[1]

REL (Recommended) Ca[1]

IDLH (Immediate danger) Ca [2.5 ppm][1]

Related compounds

Related isocyanates Methylene diphenyl diisocyanate

Naphthalene diisocyanate

Related compounds Polyurethane

Supplementary data page

Structure and Refractive index (n),

properties
Dielectric constant (εr), etc.

Thermodynamic Phase behaviour

data
solid–liquid–gas

Spectral data UV, IR, NMR, MS

 Except where otherwise noted, data are given for materials in
their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ?)

Infobox references

Toluene 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). 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 produced on a large scale, accounting for 34.1% of the
global isocyanate market in 2000, second only to MDI.[3] Approximately 1.4 billion kilograms were
produced in 2000.[4] All isomers of TDI are colorless, although commercial samples can appear
yellow.

Contents

 1Synthesis
 2Applications
 3Hazards
 4See also
 5References
 6External links

Synthesis[edit]
2,4-TDI is prepared in three steps from toluene via dinitrotoluene and 2,4-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.[4]

Distillation of the raw TDI mixture produces an 80:20 mixture of 2,4-TDI and 2,6-TDI, known as TDI
(80/20). Differentiation or separation of the TDI (80/20) can be used to produce pure 2,4-TDI and a
65:35 mixture of 2,4-TDI and 2,6-TDI, known as TDI (65/35).

Applications[edit]
The isocyanate functional groups in TDI react with hydroxyl groups to form carbamate (urethane)
links. 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]
It is used in the production of flexible polyurethane foams.

Hazards[edit]
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.[4]
In the United States, the Occupational Safety and Health Administration has set a permissible
exposure limit with a ceiling at 0.02 ppm (0.14 mg/m3), while the National Institute for Occupational
Safety and Health has not established a recommended exposure limit, due to the classification of
toluene diisocyanate as a possible occupational carcinogen.[5] This chemical was one of many that
caused two massive explosions in a chemical warehouse stationed in Tianjin, China on August 13,
2015.[6]
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.[7] All major producers of TDI are members of the International Isocyanate Institute,[citation
needed]
whose aim is the promotion of the safe handling of TDI in the workplace, community, and
environment.
High-level exposure can result in reactive airways dysfunction syndrome.[citation needed]

See also[edit]
 Methylene diphenyl diisocyanate
 Hexamethylene diisocyanate
 Isophorone diisocyanate

References[edit]
1. ^ Jump up to:a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0621". National Institute for
Occupational Safety and Health (NIOSH).
2. ^ "Toluene-2,4-diisocyanate". Immediately Dangerous to Life and Health Concentrations
(IDLH). National Institute for Occupational Safety and Health (NIOSH).
3. ^ Jump up to:a b Randall, D.; Lee, S. (2003). The Polyurethanes Book. New York: Wiley. ISBN 978-0-
470-85041-1.
4. ^ Jump up to:a b c Six, C.; Richter, F. "Isocyanates, Organic". Ullmann's Encyclopedia of Industrial
Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a14_611.
5. ^ National Institute for Occupational Safety and Health (May 1994). "Documentation for Immediately
Dangerous To Life or Health Concentrations (IDLHs)". Centers for Disease Control and Prevention.
6. ^ CNN [1]
7. ^ Allport, D. C.; Gilbert, D. S.; Outterside, S. M., eds. (2003). MDI and TDI: Safety, Health and the
Environment: A Source Book and Practical Guide. Wiley. ISBN 978-0-471-95812-3.

External links[edit]
 International Chemical Safety Card 0339
 IARC Monograph: "Toluene Diisocyanates"
 NIOSH Pocket Guide to Chemical Hazards
 NIOSH Safety and Health Topic: Isocyanates, from the website of the National Institute for
Occupational Safety and Health (NIOSH)
 International Isocyanate Institute http://www.diisocyanates.org