I made several reactions with 3,5-Dinitrobenzoyl chloride. When I looked at similar reactions for this substance, no heat was ever given in the reaction (even though heat increases the yield).
The interesting thing is that this substance turns black as soon as the heat is given to the reaction environment. Due to the fact that, theoretically, the polymerization of this material is impossible. Do you know the reason why they do not give heat to this material?
May explode on heating
https://pubchem.ncbi.nlm.nih.gov/compound/3_5-Dinitrobenzoyl-chloride#section=GHS-Classification
And the same concerns for other di-, poly- nitro derivatives. That means also, that you should avoid rectification(even at reduced pressure) for such compounds, because it often leads to an explosion due to strong heating. Only recrystallization or other methods such as chromatography could be applied for purification of dinitrocompounds.
May explode on heating; [Alfa Aesar MSDS] but some procedures exist with heating..10.1021/ja01356a047 THE IDENTIFICATION OF PHENOLS AS THE ESTERS OF 3,5-DINITROBENZOIC ACID .....ACS Pub
Firstly, an acyl chloride is a reactive molecule. When used (for example) in the ester forming reaction, it is a good idea to add the reactant while cooling because it usually generates heat by itself. It is because the chloride is neutralized with the accompanied amine added (or another base) in order to drive the reaction to the end.
Nowadays, chemistry has plenty of alternatives to make a reaction possible. Forcing a reaction simply with heat resembles physics rather than modern chemistry. So, if one reaction condition fails, it is good to think about why it fails and choose another, more suitable (and safe) reactivity environment.
...and of course, I agree with the previous comments regarding the possibility of an explosion. Structural similarity to TNT https://en.wikipedia.org/wiki/TNT is quite close, which nobody would dare heat too much, I believe :-)
The reason is most likely going to be explosion. On heating, the compound tend to dissociate into highly stable and strongly bonded CO, CO2, N2, and HCl, which require a lot of energy to release these substances. However, there are papers where the reaction of 3,5-dinitrobenzoyl chloride were heated Article Homogeneous acylation of xylan with 3, 5-dinitrobenzoyl in i...
Benzoyl Chloride decomposes on contact with hot surfaces or flames and produces highly toxic and corrosive gases (phosgene and hydrogen chloride). This generates fire and explosion hazard. Reacts with water and steam to produce lot of heat and corrosive fumes.
Benzoyl chloride is a reactive compound that can undergo various reactions under different conditions. One of the reactions that benzoyl chloride can undergo is hydrolysis, in which it reacts with water to form benzoic acid and hydrogen chloride gas. This reaction is exothermic, meaning it releases heat.
If heat is added to a reaction mixture containing benzoyl chloride and water, the hydrolysis reaction can be accelerated, leading to a rapid increase in temperature and the evolution of hydrogen chloride gas. This can pose safety risks and result in an uncontrollable reaction.
Therefore, it is generally recommended to avoid adding heat to a reaction mixture containing benzoyl chloride and water, or to limit the amount of heat added to prevent uncontrolled reaction. If heat is required for the reaction, it is important to use appropriate safety measures and to carefully monitor the reaction temperature to avoid hazardous situations.
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