BENZYL CHLORIDE FROM TOLUENE BY

CHLORINATION
INTRODUCTION

 Benzyl chloride is an organic compound with the formula C7H7Cl.

 This colourless liquid is a reactive organochloride that is a widely used chemical
building block.
 It’s another name alpha-chlorotoluene
 Preferred IUPAC name is (chloromethyl)benzene.
 Benzyl chloride is liquid at room temperature and production volume is 7,700
tonnes/year in 1993 in japan.
 Its used as a intermediate chemical as dyes, platicizers,flavorants, prefumes.
 Benzyl chloride is an alkylating agent. benzyl chloride reacts with water in a
hydrolysis reaction to form benzyl alcohol and hydrochloric acid.
 benzyl chloride mostly used at benzyl butyl phthalate and plasticizer used
extensively in vinyl flooring and other flexible poly (vinyl chloride) uses
such as food packing.
 In dyes industry benzyl chloride is used as intermediate in manufacture of
triphenylmethane dyes.
Toluene properties

 Molecular formula-C6H5CH3
 Molecular weight- 92.141 g/mol
 Appearance- colourless liquid
 Boiling point- 111oc
 Pressure- 40.55atm
 Chemical name- toluene (or) anisen
Chlorine properties

 Molecular formula- cl2

 Molecular weight- 70.8 g/mol
 Boiling point- -34.04oc
 Appearance-pale yellow –green gas
 Density- 0.002898
Benzyl chloride properties

 Chemical formula-C7H7Cl
 Molecular weight-126.58 g/mol
 Odour- pungent
 Density-1.100g/cm3
 Boiling point-179oc
 Solubility- soluble in ethanol, ethyl ether,chloroform.
various process

 Blanc chloromethylation of benzene

 Gas-phase photochemical reaction of toluene with chlorine
 Benzyl chloride from toluene by chlorination process.
Selection process

 Benzyl chloride from toluene by chlorination process

C6H5CH3 + Cl2  C6H5CH2Cl + HCL
 This process toluene and chlorine is reacted at using a ferric chloride as a catalyst.
Then manufacture by benzyl chloride and hydrochloric acid.
 The benzyl chloride production is very low impurities.
 And also colorless clear liquid.
Advantage:
 Benzyl chloride minimum is 99.5%.
Process description

 The benzyl chloride production at liquid stage.

 Then raw material is toluene are liquid at 100-110oc heated .It will be at liquid
and gases phase.
 Chlorine in dry gas phase passing at chlorinator in bottom, and adding a catalyst
(ferric chloride) it will boost up a reaction.
 The toluene at liquid phase and chlorine at gas phase is reaction occurred as a
(benzyl chloride +hydrochloric acid) is formed.
 When the gas phase (toluene and chlorine) passing at scrubber in between
condensating a toluene it will phase changed at gases to liquid.
 At bottom of the scrubber get toluene. Then it passed to neutralizer and it will be
neutralize for using base compound at top of the neutralizer.
 But the base compounds are at dilute alkali e.g.; cao (calcium chloride), NaOH (sodium
hydroxide)…now we using NaOH as a base compound.
 Neutralize processed at sodium hydroxide react with HCL and form as sodium chloride+
water and taken at bottom of the tank.
 When the solution is formed at liquid then passing at distillation column. It can be
separated by boiling point to recovery the toluene, then produce benzyl chloride. The
benzyl chloride is conversion of 70% and another process is photo chlorination reaction.
Material balance

Basis
Benzyl chloride = 15,000 ton/year
=15,000 * 1000 kg/year
=15000000/345 kg/day
=43478 kg/day
= 43478/24 kg/hr
=1800 kg/hr
Conversion =70%
Yield = 95%
MATERIAL BALANCE FOR
CHLORINATOR

Compound Input (kg/hr) Output (kg/hr)

Toluene 1404 kg/hr -----

Chlorine 1152 kg/hr -----

Benzyl chloride ----- 1699 kg/hr

HCL ----- 90 kg/hr

Mixer of products ----- 767 kg/hr

total 2556 2556

 (383.5 kg/hr)

MATERIAL BALANCE FOR SCRUBBER

Compound Input Output

Mixer of product 767 kg/hr ----

Chlorine ------- 383.5 kg/hr

Toluene ------- 383.5 kg/hr

total 767 767

MATERIAL BALANCE FOR ACID
ABSORBER

Compound Input Output

Chlorine 383.5 kg/hr ------

Water 97.48 kg ------

Vent ------- 86.65 kg

Hydrochloric acid -------- 394.28 kg/hr

total 480.93 480.93

MATERIAL BALANCE FOR
NEUTRALIZER
Compound Input Output
Benzyl chloride 1699 kg/hr 1699 kg/hr
Toluene 383.5 kg/hr 383.5 kg/hr
Hydrochloric acid 90 kg/hr -------

Sodium hydroxide 98.88 kg/hr --------

Sodium chloride ------ 145 kg/hr

Water ----- 44.5 kg
Total 2271 2271
MATERIAL BALANCE FOR
DISTILLATION COLUMN
Compound Input Output

Benzyl chloride 1699 kg/hr 1699 kg/hr

Toluene 383.5 kg/hr 383.5 kg/hr

total 2082 kg/hr 2082 kg/hr