Toluene react with chlorosulphonic acid to produce o-toluene sulphonyl chloride at zero degree temperature but in that more than 20 % p-toluene sulphonyl chloride is form. What is the best reaction condition to get a maximum yield of o-toluene sulphonyl chloride?
What are the other 80%? starting material or p-toluenesulphonic acid?
In this reaction we have worked with all material super dry and nitrogen atmosphere
I tjink you have already a very goog yield (80%), considering this kind of reaction (aromatic substitution), that always forms the ortho product. My suggestion to you, in order to maximize the yield, is to perform a factorial design, to optimize the conditions that you use (ammount of starting materials, time of reaction, temperature, etc). I have some publications about this approach that could help you.
Pankaj,
Improving yield of 2-toluene sulfonyl chloride from toluene and chlorosulfonic acid will be difficult. If you use 4-iodotoluene and then deiodinate with by catalytic hydrogenation after chlorosulfonation.
When you add 4-iodotoluene slowly to 3.0 moles of chlorosulfonic acid keep at -10 º and stir well overnight. Decompose the reaction mixture by adding onto ice dropwise and cooling externally using ice salt bath.
V P Shah
Dear Shah,
Your suggestion is right but afterall cost of product is too much increases.
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