2,4-Diaminotoluene

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2,4-Diaminotoluene
2,4-diaminotoluene.png
Names
Preferred IUPAC name
4-Methylbenzene-1,3-diamine
Other names
2,4-Toluenediamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.231 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • CC1=C(C=C(C=C1)N)N
Properties
C7H10N2
Molar mass 122.171 g·mol−1
AppearanceWhite solid
Density 1.521 g/cm3
Melting point 97 to 99 °C (207 to 210 °F; 370 to 372 K)
Boiling point 283 to 285 °C (541 to 545 °F; 556 to 558 K)
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
Ca [1]
IDLH (Immediate danger)
Ca [N.D.] [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4-Diaminotoluene is an aromatic organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. It is a white solid, although commercial samples are often yellow-tan. [2]

Contents

Preparation

It is prepared by hydrogenation of 2,4-dinitrotoluene using a nickel catalyst. Commercial samples often contain up to 20% of the 2,6-isomer. [2]

A laboratory method involves reduction of 2,4-dinitrotoluene with iron powder. [3]

Use

It is mainly used to manufacture toluene diisocyanate, which is a key raw material in polyurethane chemistry. [4] It is still the starting material used when non-phosgene methods of production of toluene diisocyanate are used. [5] [6]

It is also a degradation product of polyurethane materials produced using toluene diisocyanate.

Synthesis of C.I. Basic Yellow 9, an acridine dye. SynthesisBasicYellow9.png
Synthesis of C.I. Basic Yellow 9, an acridine dye.

Its reaction with benzenediazonium chloride gives the cationic azo dye Basic Orange 1. Condensation of 2,4-diaminotoluene with acetaldehyde gives the acridine dye called Basic Yellow 9. [7]

Toxicity

Aromatic amines in general often are classed as toxic and so the toxicity profile of this species has been studied. [8] [9] [10] It has received more in depth study in the 21st century. [11] [12]

Related Research Articles

<span class="mw-page-title-main">Isocyanate</span> Chemical group (–N=C=O)

In organic chemistry, isocyanate is the functional group with the formula R−N=C=O. Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyanates are manufactured for the production of polyurethanes, a class of polymers.

<span class="mw-page-title-main">Acridine</span> Chemical compound

Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecules pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.

<i>p</i>-Phenylenediamine Chemical compound

p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.

<span class="mw-page-title-main">Toluene diisocyanate</span> Chemical compound

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. Approximately 1.4 billion kilograms were produced in 2000. All isomers of TDI are colorless, although commercial samples can appear yellow.

<span class="mw-page-title-main">Methylene diphenyl diisocyanate</span> Aromatic diisocyanate

Methylene diphenyl diisocyanate (MDI) is an aromatic diisocyanate. Three isomers are common, varying by the positions of the isocyanate groups around the rings: 2,2′-MDI, 2,4′-MDI, and 4,4′-MDI. The 4,4′ isomer is most widely used, and is also known as 4,4′-diphenylmethane diisocyanate. This isomer is also known as Pure MDI. MDI reacts with polyols in the manufacture of polyurethane. It is the most produced diisocyanate, accounting for 61.3% of the global market in the year 2000.

<span class="mw-page-title-main">Biphenyl</span> Chemical compound

Biphenyl is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one hydrogen may use the prefixes xenyl or diphenylyl.

<span class="mw-page-title-main">Dicyclopentadiene</span> Chemical compound

Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor, with less pure samples possessing a stronger acrid odor. Its energy density is 10,975 Wh/l. Dicyclopentadiene is a co-produced in large quantities in the steam cracking of naphtha and gas oils to ethylene. The major use is in resins, particularly, unsaturated polyester resins. It is also used in inks, adhesives, and paints.

<span class="mw-page-title-main">2,4-Dinitrotoluene</span> Organic chemical compound

2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.

<i>m</i>-Xylene Chemical compound

m-Xylene (meta-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The m- stands for meta-, indicating that the two methyl groups in m-xylene occupy positions 1 and 3 on a benzene ring. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and p-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable.

Xylenols are organic compounds with the formula (CH3)2C6H3OH. They are volatile colorless solids or oily liquids. They are derivatives of phenol with two methyl groups at various positions relative to the hydroxyl group. Six isomers exist, of which 2,6-xylenol with both methyl groups in an ortho position with respect to the hydroxyl group is the most important. The name xylenol is a portmanteau of the words xylene and phenol.

2,4-Dimethyl-6-<i>tert</i>-butylphenol Chemical compound

2,4-Dimethyl-6-tert-butylphenol is the organic compound with the formula Me2(tert-Bu)C6H2OH (Me = methyl, tert-Bu = tertiary butyl). It is a colorless oil that is classified as an alkylated phenol.

<span class="mw-page-title-main">Hexamethylene diisocyanate</span> Chemical compound

Hexamethylene diisocyanate (HDI) is the organic compound with the formula (CH2)6(NCO)2. It is classified as an diisocyanate. It is a colorless liquid. It has sometimes been called HMDI but this not usually done to avoid confusion with Hydrogenated MDI.

Xylidine can refer to any of the six isomers of xylene amine, or any mixture of them.

<span class="mw-page-title-main">2,6-Lutidine</span> Chemical compound

2,6-Lutidine is a natural heterocyclic aromatic organic compound with the formula (CH3)2C5H3N. It is one of several dimethyl-substituted derivative of pyridine, all of which are referred to as lutidines. It is a colorless liquid with mildly basic properties and a pungent, noxious odor.

Mononitrotoluene or nitrotoluene (MNT or NT), is any of three organic compounds with the formula C6H4(CH3)(NO2). They can be viewed as nitro derivatives of toluene or as methylated derivatives of nitrobenzene.

1,2,3-Trimethylbenzene is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum. It is one of the three isomers of trimethylbenzene. It is used in jet fuel, mixed with other hydrocarbons, to prevent the formation of solid particles which might damage the engine.

<span class="mw-page-title-main">2,5-Diaminotoluene</span> Chemical compound

2,5-Diaminotoluene is an organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. 2,5-Diaminotoluene is a colorless crystalline solid, although commercial samples are often colored owing to air oxidation. It is commonly used in hair coloring.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.

<span class="mw-page-title-main">Tetramethylxylylene diisocyanate</span> Chemical compound

Tetramethylxylylene diisocyanate (TMXDI) is an organic compound with the formula C6H4(CMe2NCO)2 (Me = CH3). Introduced in the 1980s by American Cyanamid, the molecule features two isocyanate groups. TMXDI is generally classified as an aliphatic isocyanate, which are generally more UV stable than their aromatic counterparts.

References

  1. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a19_405
  3. ↑ Mahood, S. A.; Schaffner, P. V. L. (1931). "2,4-Diaminotoluene". Organic Syntheses. 11: 32. doi:10.15227/orgsyn.011.0032.
  4. ↑ Ji, Lu; Li, Fang; Che, Conghui; Xue, Wei; Yang, Qiusheng; Ding, Xiaoshu; Zhang, Dongsheng; Zhao, Xinqiang; Wang, Yanji (October 2023). "Single-atom Au-modified CeO2 catalyst: Structure and its catalytic performance in 2,4-diaminotoluene methoxycarbonylation reaction". Applied Catalysis A: General. 667: 119459. doi:10.1016/j.apcata.2023.119459. ISSN   0926-860X.
  5. ↑ Sun, Shuai; Liang, Ning; An, Hualiang; Zhao, Xinqiang; Wang, Guirong; Wang, Yanji (2013-06-12). "Kinetics for Dimethyl Toluene-2,4-dicarbamate Synthesis from 2,4-Diaminotoluene, Urea, and Methanol". Industrial & Engineering Chemistry Research. 52 (23): 7684–7689. doi:10.1021/ie4005095. ISSN   0888-5885.
  6. ↑ Juárez, Raquel; Padilla, Ana; Corma, Avelino; García, Hermenegildo (2008-11-05). "Organocatalysts for the Reaction of Dimethyl Carbonate with 2,4-Diaminotoluene". Industrial & Engineering Chemistry Research. 47 (21): 8043–8047. doi:10.1021/ie800126t. ISSN   0888-5885.
  7. ↑ Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a27_179
  8. ↑ National Toxicology Program (1979). "Bioassay of 2,4-diaminotoluene for possible carcinogenicity". National Cancer Institute Carcinogenesis Technical Report Series. 162: 1–139. ISSN   0163-7185. PMID   12799700.
  9. ↑ George, E.; Westmoreland, C. (1991). "Evaluation of the in vivo genotoxicity of the structural analogues 2,6-diaminotoluene and 2,4-diaminotoluene using the rat micronucleus test and rat liver UDS assay". Carcinogenesis. 12 (12): 2233–2237. doi:10.1093/carcin/12.12.2233. ISSN   0143-3334.
  10. ↑ Bermudez, Edilberto; Tillery, Deborah; Butterworth, Byron E. (January 1979). "The effect of 2,4‐diaminotoluene and isomers of dinitrotoluene on unscheduled dna synthesis in primary rat hepatocytes". Environmental Mutagenesis. 1 (4): 391–398. doi:10.1002/em.2860010412. ISSN   0192-2521.
  11. ↑ Femina Carolin, C.; Senthil Kumar, P.; Janet Joshiba, G.; Ramamurthy, Racchana; Varjani, Sunita J. (July 2020). "Bioremediation of 2,4-Diaminotoluene in Aqueous Solution Enhanced by Lipopeptide Biosurfactant Production from Bacterial Strains". Journal of Environmental Engineering. 146 (7). doi:10.1061/(ASCE)EE.1943-7870.0001740. ISSN   0733-9372.
  12. ↑ Séverin, Isabelle; Jondeau, Adeline; Dahbi, Laurence; Chagnon, Marie-Christine (2005-09-15). "2,4-Diaminotoluene (2,4-DAT)-induced DNA damage, DNA repair and micronucleus formation in the human hepatoma cell line HepG2". Toxicology. 213 (1): 138–146. doi:10.1016/j.tox.2005.05.021. ISSN   0300-483X.
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