Swig is sharing his failures in this reaction in hope that other bees will avoid the pain and torture that swig has endured.
First Swig would like to express that this was not a failed reaction, which is evident by the stale burning odor of benzyl chloride. This reaction is one of the most elementary reactions in the subject, even a monkey could be trained to mix benzyl alcohol and hydrochloric acid together. With that being said, swig can now express the problems encountered when one tries to purify benzyl chloride. Swig ran into many problems which can be lead to one or two shortcomings.
Problem 1.
According to the literature (Which can be found at
www.rhodium.ws), one should mix a 1:3 ration of benzyl alcohol and hydrochloric acid, and then slowly heat until 60c, which then two layers separate. Swig made the big mistake because he failed to appreciate all the factors that take part in this reaction. Swig did not want to waste his time with a measly 2 grams of reactant; he wanted to go for the big gun, one whole mole of benzyl chloride. However the reaction does not work so well for scaled-up reactions, why?, because it takes time, and a lot of it. You can’t just put a mole of benzyl chloride in a flask and mix hydrochloric acid and expect that the reaction will take place in an hour. It seems that one would have to wait at least 24-48 with low heat to achieve this goal. This leads swig to his next failure.
Problem 2.
A person can expect to wait at least 24 hours before distillation is complete, that is of course if that person lacks a vacuum, and uses an efficient column. It seemed that oxidization took over completely by the time enough heat was generated.
Swig did try the reaction with hydrobromic acid, and the speed of the reaction seemed to be much faster. A person needs to choose which hydrogen halide to used according to which will be safer for their lab set up. Benzyl bromide has to be the most awful smell swig has encountered in the lab, seriously, benzyl chloride does not even come close to the pain of being exposed to benzyl bromide, however benzyl chloride seems to be a lot more harmful to the body then benzyl bromide.
Even though swig has not yet successfully purified either halogen compound, Swig has some good advice that should be taking into consideration.
1. Don’t get greedy, do small reactions.
2. Distill in small portions unless one has a vacuum and good heat source.
3. Wear protection gear.
4. Wear goggles, inhalation mask, and 1-2 pair of nitrile gloves, when cleaning glassware, for some reason when water is added, the shit hits the fan., also if doing the reaction inside, cover all nearby food. It will absorb though your Doritos bag.
I hope this information has helped, please give feedback that would help make this reaction (purification) more successful.
ADDkid
P.S. If Zinc is dissolved in the hydrochoric acid the reaction would happen much faster.