https://www.thevespiary.org/rhodium/Rhodium/chemistry/benzylchloride.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/benzylchloride.html)
Look, Swig knows how to distill, the problem involved the smoke, burning. There was no stabliztion, temp kept going up and down. I am starting to think that it was due to drafts, and could never get hot enough to make it up to 179.
No offense, but obviously not. SWIM thought he knew how to distill also when he first tried to make benzyl bromide (his first real fractionation), and got similar results.
First you need to make sure your heat source is adjustable. Never just apply a bunch of heat and expect the distillation to run it's course. You must first turn on the heat and set it at a low setting, lets say 80C. Let it sit until everything that's gonna come over comes over. Then gradually increase the heat. DO this as you move through the fractions. Do it very slowly and gradually. The slower the better.
Also the rate of distillation is a factor. A big one. No distillation is gonna be fast. For purity and good results, you must do it very slowly. Vogels says around two to three drops a second collecting is fast enough. As soon as you start to hit a fraction thats coming over, decrease or increase heat until your rate is about two to three drops a sec. Distill at this rate, and do things as SWIM says, and you should recive more accurate results. And if it seems more than just benzyl chloride is coming over at it's boiling point (or it comes over in a boiling range like say 172-180 for example), then that fraction that comes over at those temps is going to have to be redistilled, for extra purity.
Speed and impatience is the enemy here. In the mean time SWIM strongly suggests going to a book store and buying Zubricks Organic Chem Survival manual. SWIM thought he knew how to distill and crystallize and everything, but he used to do it with the wrong technique and always wondered why nothing ever worked the way it was supposed to for him. It's like lifting weights, you can lift all day long and still get results, but to get proper results, you must lift with proper form.
Also SWIM STRONGLY suggests to go here:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/vogel3.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/vogel3.html)
The substance will polymerize under the influence of all common metals except nickel and lead, with evolution of corrosive fumes (hydrogen chloride - see ICSC # 0163), with fire or explosion hazard. On combustion, forms toxic and corrosive fumes (hydrogen chloride). Reacts vigorously with strong oxidants. Reacts with water, producing corrosive fumes (hydrogen chloride - see ICSC # 0163). Attacks many metals in presence of water.
Sure your rig hasn't got any metal in it? And no water in the mixture? CaCl2 would probably dry it enough if there was.
Try using mineral oil or paraffin wax for your bath, it doesn't smoke easily. Wax could go up to 300 C. It also may help to insulate the bath and/or the flask up to the condensor. Hardware stores sell cuffs for wrapping water heater pipes.
http://www.jtbaker.com/msds/englishhtml/b1957.htm (http://www.jtbaker.com/msds/englishhtml/b1957.htm)
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0107 (http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0107)