https://doi.org/10.1007/s10562-010-0507-9. Toluene has also been used as a coolant for its good heat transfer capabilities in sodium cold traps used in nuclear reactor system loops. Toluene at 100% can be used as a fuel for both two-stroke and four-stroke engines; however, due to the density of the fuel and other factors, the fuel does not vaporize easily unless preheated to 70 °C (158 °F). Complete the following reaction: xeF4 + SbF5 --> X e F 4 + S b F 5 → [X e F 3] + [S b F 6]-Answer. Thus 94.4% conversion of toluene and 98.4% selectivity of benzoic acid could be obtained at 110 °C under 0.3 MPa for 3 h in the presence of 10 mol% NHPI and 4 mol% MnO2. As such, its IUPAC systematic name is methylbenzene. The production of benzoic acid from toluene in the liquid phase with pure oxygen was studied. [8][9], The compound was first isolated in 1837 through a distillation of pine oil by the Polish chemist Filip Walter, who named it rétinnaphte. [12] In 1850, French chemist Auguste Cahours isolated from a distillate of wood a hydrocarbon which he recognized as similar to Deville's benzoène and which Cahours named toluène.[13]. At a dilution ratio of 1/4, 89% toluene conversion and 80% selectivity to benzoic acid was obtained. Graphical Abstract View [34], Several types of fungi including Cladophialophora, Exophiala, Leptodontium, Pseudeurotium zonatum, and Cladosporium sphaerospermum, and certain species of bacteria can degrade toluene using it as a source of carbon and energy. PubMed Google Scholar. Inhalation of toluene in low to moderate levels can cause tiredness, confusion, weakness, drunken-type actions, memory loss, nausea, loss of appetite, hearing loss, and colour vision loss. Trinitrotoluene is the explosive typically abbreviated TNT. [26] In 2013, worldwide sales of toluene amounted to about 24.5 billion US-dollars. Benzoic acid could be efficiently prepared from aerobic oxidation of toluene using manganese dioxide (MnO 2) and N -hydroxyphthalimide (NHPI) as catalysts. Toluene had also been used in the process of removing the cocaine from coca leaves in the production of Coca-Cola syrup. The possession and use of toluene and products containing it are regulated in many jurisdictions, for the supposed reason of preventing minors from obtaining these products for recreational drug purposes. First oxidizing toluene to benzoic acid and then nitration will give product on meta position. Correspondence to It undergoes sulfonation to give p-toluenesulfonic acid, and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene. Allow mixture to reflux for 3 to 4 hours until oily toluene disappears. [11] In 1843, Jöns Jacob Berzelius recommended the name toluin. Google Scholar, Bottinoa A, Capannelli G, Comitea A, Di Felice R (2004) Chem Eng Res Des 82:229, Li XQ, Xu J, Wang F, Gao J, Zhou LP, Yang GY (2006) Catal Lett 108:137, Li XQ, Xu J, Zhou LP, Wang F, Gao J, Chen C, Ning JB, Ma H (2006) Catal Lett 110:255, Raja R, Thomas J, Dreyer V (2006) Catal Lett 110:179, Dumitriu D, Bârjega R, Frunza L, Macovei D, Hu T, Xie Y, Pârvulescu VI, Kaliaguine S (2003) J Catal 219:337, Parvulescu V, Constantin C, Su BL (2003) J Mol Catal A 202:171, Tsang SC, Zhu J, K.Yu KM (2006) Catal Lett 106:123, Zhu J, Robertson A, Tsang SC (2002) Chem Commun 18:2044, Sahle-Demessie E, Gonzalez MA, Enriquez J, Zhao Q (2000) Ind Eng Chem Res 39:4858, Guo CC, Liu Q, Wang XT, Hu HY (2005) Appl Catal A 282:55, Huang G, Wang A, Liu S, Guo Y, Zhou H, Zhao S (2007) Catal Lett 114:174, Yoshino Y, Hayashi Y, Iwahama T, Sakaguchi S, Ishii Y (1997) J Org Chem 62:6810, Recupero F, Punta C (2007) Chem Rev 107:3800, Ishii Y, Sakaguchi S, Iwahama T (2001) Adv Synth Catal 34:393, Sheldon RA, Arends I (2006) J Mol Catal A 251:200, Minisci F, Punta C, Recupero F (2006) J Mol Catal A 251:129, Yang GY, Ma Y, Xu J (2004) J Am Chem Soc 126:10542, Yang GY, Zhang Q, Miao H, Tong X, Xu J (2005) Org Lett 7:263, Zheng GX, Liu CH, Wang QF, Wang MY, Yang GY (2009) Adv Synth Catal 351:2638, Zhou LP, Chen Y, Yang XM, Su YL, Zhang W, Xu J (2008) Catal Lett 125:154, Taha N, Sasson Y (2010) Org Process Res Dev 14:701, Yao Z, Hu XB, Mao JY, Li HR (2009) Green Chem 11:2013, Amorati R, Lucarini M, Mugnaini V, Pedulli GF (2003) J Org Chem 68:1747, Aoki Y, Sakaguchi S, Ishii Y (2004) Adv Synth Catal 346:199, Einhorn C, Einhorn J, Marcadal C, Pierre J-L (1997) Chem Commun 447, Yang GY, Zheng LW, Wu GH, Lin XS, Song MP (2007) Adv Synth Catal 349:2445. This is a preview of subscription content, log in to check access. Toluene is oxidized with alkaline K M n O 4 followed by acidification to form benzoic acid.

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