Is producing 4,4'-dichlorodiphenyl sulfone with H2SO4 possible?

You can make dichloro-DDS from chlorobenzene using thionyl chloride -https://www.thieme-connect.com/products/ejournals/abstract/1... , followed by oxidation - https://www.ias.ac.in/article/fulltext/jcsc/128/08/1321-1325

Do you have the reference to replace Cl with NH₂ to make dapsone ?

I don't understand why you selected this route when a more simple and common route exists

1.Nitrobenzene to nitrobenzene sulphide - http://www.rsc.org/suppdata/cc/c3/c3cc37795d/c3cc37795d.pdf (pg 6 of pdf)

2.Oxidation of sulphide to sulphone-https://www.organic-chemistry.org/abstracts/literature/433.s...
UHP - https://en.wikipedia.org/wiki/Hydrogen_peroxide_-_urea#Produ...

3.reduction of nitro to amine to get dapsone

[Edited on 2-5-2019 by CuReUS]

Quote: Originally posted by CuReUS

You can make dichloro-DDS from chlorobenzene using thionyl chloride -https://www.thieme-connect.com/products/ejournals/abstract/1... , followed by oxidation - https://www.ias.ac.in/article/fulltext/jcsc/128/08/1321-1325 Do you have the reference to replace Cl with NH2 to make dapsone ? I don't understand why you selected this route when a more simple and common route exists 1.Nitrobenzene to nitrobenzene sulphide - http://www.rsc.org/suppdata/cc/c3/c3cc37795d/c3cc37795d.pdf (pg 6 of pdf) 2.Oxidation of sulphide to sulphone-https://www.organic-chemistry.org/abstracts/literature/433.s... UHP - https://en.wikipedia.org/wiki/Hydrogen_peroxide_-_urea#Produ... 3.reduction of nitro to amine to get dapsone [Edited on 2-5-2019 by CuReUS]

We had several limitations. One of them was that, we could only use lab available materials and equipment.

For equipment, we had a hotplate (the cooking kind! We couldn't use the stirring hotplate cuz we couldnt move it from the other room to move it under a better fume hood. Wouldn't want to expose everyone so we made do.), distillation equipment (lack of temp control meant we couldn't do fractional distillation for azeotropic stuff though), a rotavap (only option for vacuum distillation. We avoid it cuz if anything breaks we're absolutely dead), and oven, and UV for TLC. We also have an HPLC, but were not allowed to use that (we havent trained for it yet, and the thesis people are using it)

Also, we only have a few weeks to do it. We can't do overnight refluxes, cuz we also have to be under supervision. Your suggested sulphide route was so close to being possible though!

As for the chemicals, we dont have SOCl2 for some reason. So that route is also impossible

As for the source, we based our synthesis on this patent:
https://patents.google.com/patent/CN106518735A/en

But it really didn't go how it described. Something formed, but we think it's just chlorobenzenesulfonic acid. We dropped this project cuz we really didn't have the time to deliberate errors.

The amination procedure described in that patent uses ammonium chloride. We also considered this metal catalyzed aryl halide amination method:
https://pubs.rsc.org/en/content/articlelanding/2010/cs/c0036...

Quote: Originally posted by Gryn

Your suggested sulphide route was so close to being possible though!

Quote: Originally posted by clearly_not_atara

In the attached paper, Pilyugin describes a number of methods that have been used to convert 4-nitrochlorobenzene and sodium sulfide into an aryl disulfide. He gives a one-pot two-phase method for converting 4-chloronitrobenzene into 4-amino-4'-nitro-diphenyl sulfide, which should be good enough for dapsone production. Pilyugin does this successfully without a nitrogen atmosphere or an overnight reaction. The reagents used are chlorobenzene (solvent), 4-nitrochlorobenzene, sodium sulfide, and PEG-400, which is a phase-transfer catalyst, and happens to be relatively safe and cheap. 4-nitrochlorobenzene is made by nitration of chlorobenzene. The only special equipment required is a "hydroacoustic device", but you may be able to improvise using e.g. a speaker, or some commercial ultrasound-producing equipment.