Toluene, methyl benzene or phenyl methane Assignment Help

Benzene - Toluene, methyl benzene or phenyl methane

Toluene, methyl benzene or phenyl methane

         Toluene is the simplest homolouge of benzene. It was first found by dry distillation of tolubalsam and hence called toluene. It is usually called as tolual.

         Methods of preparation

         (i) From benzene [Friedel-craft's reaction] :  

1360_toluene.png

  •  Alkyl halide employed can undergo an isomeric change

1216_toluene1.png

  •  Catalysts may be needed in place of anhydrous AlCl3 are,

AlCl3 > SbCl3 > SnCl4 > BF3 > ZnCl2 >  HgCl2

         (ii) Wurtz fitting reaction:

1385_toluene2.png 

         (iii) Decarboxylation :

729_toluene3.png 

         (iv) From cresol

 

11_toluene4.png

 

         (v) From toluene sulphonic acid :

 

2488_toluene5.png

         (vi) From toluidine :

1797_toluene6.png

         (vii) From grignard reagent :

 1376_toluene7.png

 

   (viii) Commercial preparation

         From coal tar : The main source of commercial production of toluene is the light oil fraction of coal-tar. The light oil fraction is refined with conc. H2SO4 to remove the bases, then with NaOH to remove acidic substances and lastly with water. It is related to fractional distillation. The vapours collected between 80 - 1100 C is 90% benzol which contains 70-80% benzene and 14-24% toluene. 90% benzol is again distilled and the portion distilling between  108 - 1100 C  is collected as toluene.

(ix) From n- heptane and methyl cyclohexane

 

1659_toluene8.png

 

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