トルエン-2
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/09/19 23:41:18」(JST)
| Names | |
|---|---|
| IUPAC name
2,4-diisocyanato-1-methyl-benzene
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| Other names
Tolylene diisocyanate
Methyl phenylene diisocyanate |
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| Identifiers | |
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CAS Number
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584-84-9 Y |
| ChEBI | CHEBI:53556 Y |
| ChEMBL | ChEMBL1086446 Y |
| ChemSpider | 13835351 Y |
| Jmol 3D model | Interactive image |
| RTECS number | CZ6300000 |
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InChI
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SMILES
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| Properties | |
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Chemical formula
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C9H6N2O2 |
| Molar mass | 174.2 g/mol |
| Appearance | Colorless to pale yellow 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) |
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Solubility in water
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Reacts |
| Vapor pressure | 0.01 mmHg (25°C)[1] |
| Hazards | |
| Safety data sheet | See: data page |
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EU classification (DSD)
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Very toxic (T+) Carc. Cat. 3 |
| R-phrases | R26, R36/37/38, R40, R42/43, R52/53 |
| S-phrases | (S1/2), S23, S36/37, S45, S61 |
| NFPA 704 |
1
3
1
|
| Flash point | 127 °C (261 °F; 400 K) |
| Explosive limits | 0.9%-9.5%[1] |
| Lethal dose or concentration (LD, LC): | |
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LC50 (median concentration)
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14 ppm (rat, 4 hr) 13.9 ppm (guinea pig, 4 hr) |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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C 0.02 ppm (0.14 mg/m3)[1] |
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REL (Recommended)
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Ca[1] |
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IDLH (Immediate danger)
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Ca [2.5 ppm][1] |
| Related compounds | |
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Related isocyanates
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Methylene diphenyl diisocyanate Naphthalene diisocyanate |
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Related compounds
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Polyurethane |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) | |
| 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]
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 crude 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).
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
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.[citation needed][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.
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| リンク元 | 「トルエン-2,4-ジイソシアネート」 |
| 関連記事 | 「diisocyanate」 |