Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Toluene diisocyanate: Difference between pages

| Watchedfields = changed

| verifiedrevid = 477003341

| Name = Toluene-2,4-diisocyanate

| ImageFile = Structural formula of toluene-2,4-diisocyanate.svg

| ImageName = Toluene diisocyanate

| ImageFile1 = Toluene-2,4-diisocyanate 3D ball.png

| ImageName1 = Ball and stick model of toluene diisocyanate

| PIN = 2,4-Diisocyanato-1-methylbenzene

| OtherNames = Toluene diisocyanate<br/>Toluene-2,4-diisocyanate<br />Methyl phenylene diisocyanate<br />Benzylene 2,4-diisocyanate<br/>2,4-Di(nitrogencarbonyl)toluene

| Section1 = {{Chembox Identifiers

| index_label=2,4

| index1_label=2,6

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 584-84-9

| CASNo1 = 91-08-7

| Beilstein = 744602

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI1 = 53557

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1086446

| ChEMBL1 = 1443390

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID1 = 6773

| DTXSID1 = DTXSID2026157

| EC_number = 209-544-5

| EC_number1 = 202-039-0

| PubChem = 11443

| PubChem1 = 7040

| RTECS = CZ6300000

| RTECS1 = CZ6310000

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 17X7AFZ1GH

| UNNumber = 2078

| UNII1 = 78243HXH5O

| SMILES = Cc1ccc(cc1\N=C=O)\N=C=O

| InChI1=1S/C9H6N2O2/c1-7-8(10-5-12)3-2-4-9(7)11-6-13/h2-4H,1H3

| InChIKey1 = RUELTTOHQODFPA-UHFFFAOYSA-N

| SMILES1 = CC1=C(C=CC=C1N=C=O)N=C=O

| Section2 = {{Chembox Properties

| Formula = C₉H₆N₂O₂

| MolarMass = 174.2 g/mol

| Appearance = Colorless liquid

| Odor = sharp, pungent<ref name=PGCH/>

| Density = 1.214 g/cm³, liquid

| Solubility = Reacts

| MeltingPtC = 21.8

| MeltingPt_notes =

| BoilingPtC = 251

| BoilingPt_notes =

| VaporPressure = 0.01 mmHg (25°C)<ref name=PGCH/>

| Section7 = {{Chembox Hazards

| ExternalSDS =

| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|315|317|318|319|330|334|335|351|412}}

| PPhrases = {{P-phrases|201|202|260|261|264|271|272|273|280|281|284|285|302+352|304+340|304+341|305+351+338|308+313|310|312|320|321|332+313|333+313|337+313|342+311|362|363|403+233|405|501}}

| NFPA-H = 3

| NFPA-R = 1

| NFPA-F = 1

| FlashPtC = 127

| IDLH = Ca [2.5 ppm]<ref name=PGCH>{{PGCH|0621}}</ref>

| PEL = C 0.02 ppm (0.14 mg/m³)<ref name=PGCH/>

| REL = Ca<ref name=PGCH/>

| ExploLimits = 0.9–9.5%<ref name=PGCH/>

| LC50 = 14 ppm (rat, 4 hr)<br/>13.9 ppm (guinea pig, 4 hr)<br/>9.7 ppm (mouse, 4 hr)<br/>11 ppm (rabbit, 4 hr)<ref>{{IDLH|584849|Toluene-2,4-diisocyanate}}</ref>

| Section8 = {{Chembox Related

| OtherFunction_label = [[isocyanate]]s

| OtherFunction = [[Methylene diphenyl diisocyanate]]<br />[[Naphthalene diisocyanate]], [[1,3-Diisocyanatobenzene]]

| OtherCompounds = [[Polyurethane]]

'''Toluene diisocyanate''' ('''TDI''') is an [[organic compound]] with the formula CH₃C₆H₃(NCO)₂. Two of the six possible [[isomer]]s 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 [[Methylene diphenyl diisocyanate|MDI]].<ref name="Randall">{{cite book |author1=Randall, D. |author2=Lee, S. | title = The Polyurethanes Book | publisher = Wiley | location = New York | year = 2003 | isbn = 978-0-470-85041-1 }}</ref> Approximately 1.4 billion kilograms were produced in 2000.<ref name=Ullmann/> All isomers of TDI are colorless, although commercial samples can appear yellow.

==Synthesis==

2,4-TDI is prepared in three steps from [[toluene]] via [[dinitrotoluene]] and [[2,4-Diaminotoluene|2,4-diaminotoluene]] (TDA). Finally, the TDA is subjected to ''phosgenation'', i.e., treatment with [[phosgene]] to form TDI. This final step produces [[Hydrochloric acid|HCl]] as a byproduct and is a major source of industrial hydrochloric acid.<ref name=Ullmann>{{ Ullmann | author = Six, C.; Richter, F. | title = Isocyanates, Organic | doi = 10.1002/14356007.a14_611 }}</ref>

:[[File:TDI-Synthese.svg|frameless|upright=2.75]]

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==

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.<ref name="Randall" /> It is also sometimes used in [[rocket propellants]].<ref>{{cite web|url=https://www.globalsecurity.org/wmd/world/iraq/ababil.htm|title=Ababil-100/Al Fat'h|website=GlobalSecurity.org|archive-url=https://web.archive.org/web/20190415172938/https://www.globalsecurity.org/wmd/world/iraq/ababil.htm|archive-date=15 April 2019}}</ref>

It is used in the production of rigid polyurethane foams with a high temperature stability.

==Hazards==

The [[LD50]] for TDI is 5800&nbsp;mg/kg for oral contact and [[LC50]] of 610&nbsp;mg/m³ for the vapour. Despite the indicated low toxicity, TDI is classified as "very toxic" by the European Community.<ref name=Ullmann/>

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&nbsp;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.<ref>{{cite web|author=National Institute for Occupational Safety and Health|title=Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs)|publisher=Centers for Disease Control and Prevention|date=May 1994|url=https://www.cdc.gov/niosh/idlh/584849.html}}</ref>

This chemical was one of many that were stored by the company whose chemical warehouse stationed in Tianjin, China was the site of [[2015 Tianjin explosions|massive explosions on August 12, 2015]].<ref>{{cite web|url=http://edition.cnn.com/2015/08/13/asia/china-tianjin-explosions/|website=CNN|title=Tianjin explosion: Dozens dead, areas of Chinese port city devastated|date=13 August 2023|last1=Ripley|first1=Will|last2=Jiang|first2=Steven|last3=Mullen|first3=Jethro|access-date=1 October 2023}}</ref>

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.<ref>{{ cite book |editor1=Allport, D. C. |editor2=Gilbert, D. S. |editor3=Outterside, S. M. | year = 2003 | title = MDI and TDI: Safety, Health and the Environment: A Source Book and Practical Guide | publisher = Wiley | isbn = 978-0-471-95812-3 }}</ref> All major producers of TDI are members of the International Isocyanate Institute,{{citation needed|date=August 2014}} 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|date=May 2017}}

==See also==

* [[Hexamethylene diisocyanate]]

* [[Isophorone diisocyanate]]

* [[Methylene diphenyl diisocyanate]]

==References==

{{reflist}}

==External links==

*[http://www.inchem.org/documents/icsc/icsc/eics0339.htm International Chemical Safety Card 0339]

*[http://www.inchem.org/documents/icsc/icsc/eics0339.htm IARC Monograph: "Toluene Diisocyanates"]

*[https://www.cdc.gov/niosh/npg/npgd0621.html NIOSH Pocket Guide to Chemical Hazards]

* [https://www.cdc.gov/niosh/topics/isocyanates/ NIOSH Safety and Health Topic: Isocyanates], from the website of the National Institute for Occupational Safety and Health (NIOSH)

* International Isocyanate Institute http://[http://www.diisocyanates.org www.diisocyanates.org]

[[Category:Isocyanates]]

[[Category:Monomers]]

[[Category:IARC Group 2B carcinogens]]

[[Category:2-Tolyl compounds]]

[[Category:4-Tolyl compounds]]