Chemistry:2,4-Diaminotoluene
2,4-Diaminotoluene is an aromatic organic compound with the formula C
6H
3(NH
2)
2CH
3. It is one isomer of six with this formula. It is a white solid, although commercial samples are often yellow-tan.[1]
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.[1]
A laboratory method involves reduction of 2,4-dinitrotoluene with iron powder.[2]
Use
It is mainly used to manufacture toluene diisocyanate, which is a key raw material in polyurethane chemistry.[3] It is still the starting material used when non-phosgene methods of production of toluene diisocyanate are used.[4][5]
It is also a degradation product of polyurethane materials produced using toluene diisocyanate.
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.[6]
Toxicity
Aromatic amines in general often are classed as toxic and so the toxicity profile of this species has been studied.[7][8][9] It has received more in depth study in the 21st century.[10][11]
References
- ↑ 1.0 1.1 Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_405
- ↑ Mahood, S. A.; Schaffner, P. V. L. (1931). "2,4-Diaminotoluene". Organic Syntheses 11: 32. doi:10.15227/orgsyn.011.0032. http://dx.doi.org/10.15227/orgsyn.011.0032.
- ↑ Ji, Lu; Li, Fang; Che, Conghui; Xue, Wei; Yang, Qiusheng; Ding, Xiaoshu; Zhang, Dongsheng; Zhao, Xinqiang et al. (October 2023). "Single-atom Au-modified CeO2 catalyst: Structure and its catalytic performance in 2,4-diaminotoluene methoxycarbonylation reaction". Applied Catalysis A: General 667. doi:10.1016/j.apcata.2023.119459. ISSN 0926-860X. Bibcode: 2023AppCA.667k9459J. https://doi.org/10.1016/j.apcata.2023.119459.
- ↑ 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" (in en). Industrial & Engineering Chemistry Research 52 (23): 7684–7689. doi:10.1021/ie4005095. ISSN 0888-5885. https://pubs.acs.org/doi/10.1021/ie4005095.
- ↑ Juárez, Raquel; Padilla, Ana; Corma, Avelino; García, Hermenegildo (2008-11-05). "Organocatalysts for the Reaction of Dimethyl Carbonate with 2,4-Diaminotoluene" (in en). Industrial & Engineering Chemistry Research 47 (21): 8043–8047. doi:10.1021/ie800126t. ISSN 0888-5885. https://pubs.acs.org/doi/10.1021/ie800126t.
- ↑ Gessner, Thomas; Mayer, Udo (2000). "Triarylmethane and Diarylmethane Dyes". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_179. ISBN 978-3-527-30385-4.
- ↑ 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.
- ↑ 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. PMID 1747922. https://doi.org/10.1093/carcin/12.12.2233.
- ↑ 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" (in en). Environmental Mutagenesis 1 (4): 391–398. doi:10.1002/em.2860010412. ISSN 0192-2521. PMID 553809. https://onlinelibrary.wiley.com/doi/10.1002/em.2860010412.
- ↑ 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" (in en). Journal of Environmental Engineering 146 (7). doi:10.1061/(ASCE)EE.1943-7870.0001740. ISSN 0733-9372. https://ascelibrary.org/doi/10.1061/%28ASCE%29EE.1943-7870.0001740.
- ↑ 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. PMID 15996806. Bibcode: 2005Toxgy.213..138S. https://www.sciencedirect.com/science/article/pii/S0300483X05002477.
 |  |
