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From: ReactionFactory
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  • Everyone loves ⏣

  • this method is as same as preparation of methane where we add sodium acelate (CH3COONa) with soda lime (NaOH + CaO) to give methane (CH4) and sodium carbonate (Na2CO3)

  • Dumb question but how much Benzene did you get out of this synthesis?

  • If you want to re-use your "dry distillation apparatus", you could improve your device, when you'd replace the Mighty Putty "gasket" by a thread cut in the copper pipe, together with a nut and a flat gasket at each side of the tin's lid. Times have changed: When I was young and made chemical experiments (in 1976 I was 14), Benzene was sold at each pharmacy or drug store without restrictions at any hobby-chemist.

  • can benzene be sinthesice from say cinnamon?

  • @Revelde20

    I am afraid no: Cinnamon only contains small amounts of Cinnamaldehyde and Cinnamic acid, which also would lead to adverse side reactions. Sodiumbenzoate is the best starter material for the preparation of Benzene, only a decorboxylation step has to be carried out (apart from refining the raw benzene by a repeated distillation).

  • @196Stefan2 thank you !

  • Hi, nice video, and cool apparatus for the first distillation. Propane and melting point of 600 degrees are a good heating choice - well chosen with the camp stove. Can you please describe what is happening chemically? The sodium / calcium hydroxide is releasing hydroxide ions, what is the Sodium Benzoate's role in the transaction? Could Potassium Benzoate be used as well? Thanks 1x10E6!!! (A million!) and very interesting stuff. :)

  • @daviddanielgraham

    If I'm not mistaken, neutral carbon dioxide comes off anionic benzoate leaving a phenyl carbanion which then nucleophilically abstracts a proton from hydroxide to produce benzene distilling off. The remaining sodium oxide then reacts with the carbon dioxide produced earlier to form sodium carbonate which remains in the boiling flask.

    Potassium benzoate is suitable as well, so long as you change the recipe so as to keep the molar ratios the same.

  • Very nice video ! Be extremely careful with benzene. I think this red material in the flask is from various polycondensation of benzene, like tetracene (red-orange color), equation :

    4 C6H6 => 3 C2H4 + C18H12

  • @chemC2H5OH

    We think something like fluorene or fluorenone is present, as it fluoresces under a black light. I've read papers describing the pyrolysis of benzoate salts which indicated that possibility.

  • do you have to have copper pipe?

    

  • @superawesome484

    Most metal pipes should be fine if you have a good seal, they don't melt, and don't react. What are you thinking of using?

  • @ReactionFactory

    i dont know my uncle owns a scrap yard so whatever i find there

  • Can you use simple distillation, I assume no but I would be happy if you could because I don't have a setup for fractional distillation...yet.

  • @PyroPudding

    As the purpose of the distillation is to remove the benzene from the side-products, all of which will have much higher molecular masses, and therefore boiling points, a simple distillation should be almost exactly as suitable as a fractional distillation for this experiment, as long as you don't get it so hot as to start vaporizing the side-products.

  • how much of the vapors do you have do inhale to get cancer? or else i will have cancer now:(

  • @thegodofchemistry

    Incidental exposure isn't cause for too much concern, whereas being exposed to benzene vapor on a day-to-day basis for many years would be riskier. But there are too many risk factors at play here (genetics, diet, occupation, habitual tobacco use, etc.) that vary on a person-to-person basis to come up with a definite number for the threshold exposure to induce cancer. But generally, the less exposure you receive, the better off you'll be in the long run.

  • @ReactionFactory thanks :)

  • @ReactionFactory for the second distillation does it have to be in glass or can it be in the same set up as the first?

  • @618suckit

    I guess you could use the paint can still for normal distillation, but it's a pretty crappy apparatus.

  • @ReactionFactory thanks, also where can you get sodium benezoate and sodium hydroxide?

  • @618suckit

    I think the easiest sources would be to buy sodium benzoate online, perhaps on eBay, and to buy the sodium hydroxide from a hardware store like Ace as a solid drain opener.

  • Could I substitute potassium benzoate instead of sodium benzoate?

  • @PyroAbsestion22

    Absolutely, yes, though you will want to adjust the mass ratio of sodium hydroxide to potassium benzoate to around 4:15, respectively, to account for the larger molar mass of potassium benzoate

  • I am considering making ethylbenzene in the future. Do you know of any reaction pathways except the hydrogenation of styrene that would yield ethylbenzene?

  • @yellowmetalcyborg

    A Friedel-Crafts alkylation of benzene with chloroethane and aluminium trichloride catalyst would do it. Of course, those latter two components can be hard for an amateur to get and work with. Though, hydrogenations tend to be hard for amateurs too ... what catalyst would you use for the hydrogenation?

  • @ReactionFactory I was hoping I could use nickel oxide as catalyst, but I try to avoid using catalysts because every single time, they do something unexpected. Plus, I'm not sure if I'm allergic to nickel.

    Do you think hydrogen radicals would do the trick?

    H2O2--FeCl3--> 2'OH

    CO2+ C--> 2CO

    2CO+ 2'OH--> 2CO2+ 2H

    2H+ C6H5CH=CH2--> C6H5CH2CH3

  • @yellowmetalcyborg

    Trying to use an exceedingly strong oxidizing mixture like Fenton's reagent to hydrogenate something seems like a doomed venture from the start.

  • @ReactionFactory The Friedel-Crafts reaction is starting to look pretty darn easy to do. Mixing sulfuric acid with sodium bromide would generate HBr in situ. If I react ethanol with hydrobromic acid, I'd get bromoethane that would boil off at ~40C. It would then react with benzene with the help of a catalyst to yield hydrogen bromide gas and ethylbenzene. I could then recycle the HBr to make more ethylbenzene.

  • @yellowmetalcyborg

    Producing anhydrous aluminium trichloride at home is actually really hard, and the alternative Lewis acidic catalysts for an Friedel-Crafts alkylation are even harder. Even buying it is quite tricky. That's the reason why Friedel-Crafts reactions are hard for the amateur.

  • @ReactionFactory And I thought making AlCl3 was the least of my worries...

    Nonetheless, I have done a little more research and stumbled upon something even better than hydrogenation and Friedel-Crafts; it's called electrochemical hydrogenation. I found this on sciencemadness, here's the link:

    / t a l k / v i e w t h r e a d . p h p ? t i d = 1 1 0 7 6

    I thought you might find this interesting.

  • @yellowmetalcyborg Benzene and acetyl chloride with a aluminum trichloride catalyst would form acetophenone in high yield, that could be reduced with zinc and hydrochloric acid to form ethylbenzene.

  • The gunk contains biphenyl and related compounds. It is essentially a mush of cancer waiting to kill someone. Best thing to do is to burn it.

  • @endimion17 biphenyl boils at 255,5 C deg...

  • @eskade1 Not important. Liquids transfer distillation systems even though their boiling point hasn't been reached. It's either as an aerosol, either as volatile fumes. Distillations aren't perfect, and though very little of the unwanted stuff manages to find its way to the receiving flask, it starts to be very important when the stuff is extremely poisonous.

  • @endimion17 and that's why I would use vigreux column :)

  • @eskade1 Exactly. And I'd repeat the procedure for a couple of times if I don't have any other way of purification.

  • That was flippin fascinating. Well done.

  • Can I make benzene from scratch lik c6h6 just combine the carbon atoms by heat or something because this is not what I pictured ....any help would be much appreciated

  • @seandizzy

    No, you can't make benzene by combining graphite and hydrogen and heating. I guess sometimes you can form compounds by mixing their constituent elements and heating, but at least in organic chemistry, that's not going to work for you.

  • @seandizzy I'd reccomend laying off benzene or anything similar if you need someone to answer such a trivial question. Benzene is a seriously dangerous compound. You wouldn't want to get pulmonary cancer, would you?

  • Is it just me, or is distillation beautiful?

  • @AjavatDWP nope it's not just you :)

  • I've just made a quick video of it going in the back garden, with the yield of orange gold. It should be the newest video on my list if you sort by date - 'Benzene from Benzoate'

  • Comment removed

  • Rather than build a copper condenser, or use an open iced flask, I used some spare copper compression 90 degree bends (two) to make a recovery bend from the fitting on the tin. I stuck a rubber stopper on the other end and had it in one of the side necks on a glass flask. On the remaining port of the flask, I put a condenser I already have. Thereby avoiding the need to build a condenser or use ice, but also trapping the benzene if any tried to escape to glass collection flask.

  • @lexichronicle2

    I have also found a good way to get a condenser on this reaction. I put a vacuum takeoff adapter on top of a Liebig condenser and ran the benzene fumes through the Liebig. Really good condensation from that.

  • @ReactionFactory I think that's definitely the way to do it, rather than making a water jacket from copper - it's too expensive and time consuming. And I can't imagine someone wanting benzene if they don't already have a semi decent glass condenser - it'd just boil off any subsequent work and help promote some cancer in the process. I've since distilled mine from some CaCl2, about 3l in total, for a yield of around 85%; I expect it'd have been 50% if I hadn't recycled the waste.

  • Just finishing doing this on a 7.5 kilo batch of benzoate, using a 2.5l paint tin over a camping stove. Thus far, there's about 2.5l in the flask, not sure since there's water in there with it and it's still crude that needs vigreuxing.

    I have a neat tip though! Go to the plumbing section & look for 'Compression tank coupling / fitting'. Wrap with PTFE, drop thru the hole in the li and tighten up. They work great! Msg me for my facebook, I have a ton of photos.

  • @h0meIandsecurity

    What that means is that I have more molecules of sodium hydroxide than I do of sodium benzoate. It's just that sodium hydroxide weighs significantly less per molecule. The ratios you're going to use are 327 grams of sodium benzoate for every 100 grams of sodium hydroxide. Good luck, and be careful.

  • @h0meIandsecurity

    Nope, we have 1.86 moles of sodium benzoate, and 2.05 moles of sodium hydroxide here. That's a 10% molar excess of sodium hydroxide.

  • I've done this synthesis a few times but scaling it up seems to be dificult :(.

  • @Hydroxybenzeen

    I recently made 20 fluid ounces of dry benzene by running the decarboxylation (with the same quantities of materials as in the video) four times (The last two runs were cut short before it had all been extracted, though.) It can then be distilled and dried in one batch together.

    BTW, try putting a little bit of colorful crude material under a blacklight ... it fluoresces!

    Hopefully there will be a video on bromobenzene in the not-too-distant future.

  • @Hydroxybenzeen Scaling up is definitely tricky, as the material in the can insulates the base near the flame. A 2.5l paint can with .25 to 1 kilo in it is as big as it's getting on a camping stove, and then you'll probably find unreacted material in it (I had to sort my waste and rerun). I tried insulation as well, bigger flames would likely damage the steel. I think the key to using bigger containers would be to use nichrome wire to heat the container all over.

  • How is the vapor condensing in that distillation setup? Have you ever heard of Toluene disproportionation (TDP)? The theory is simple, but how hard would it be to carry that out?

  • @nicoheckens1

    What do you mean by the vapor condensing in the distillation setup? There's reflux, due to heat transferring out of the column, and there's condensate forming in the Graham condenser due to the coolant water which we are pumping through it.

    I have heard of toluene disproportionation in passing. Toluene and xylene can both be bought from Ace Hardware in Florida, so there's no practical use to trying it. AFAIK, the hard part would be acquiring or making anhydrous aluminium chloride.

  • @h0meIandsecurity

    The coloration has been reported by other amateurs performing this and similar experiments without copper components, so I think we can rule that explanation out. Under certain conditions, the color comes out more yellow than red. We think that the yellow impurity, which we believe is present even when the distillate is primarily red, is 9-fluorenone.

    Because we like spiders. Spiders are awesome.

  • Brave man. Useful death. He died so that we can live, and be aware.

  • Benzene causes cancer also, it's highly flammable. Make sure you have water near you to jump in if things go wrong. You can't get the fire out br rolling on the ground, it just makes it worst, it burns even in water for a while. Bad shit.

  • PRAISE GOD ALMIGHTY, for this. YET, Remember Benzene is ACCUMULATIVE in the body.. It is nothing to get a raincoat, a chepo plastic face mask, and vacuum hose with chepo sponges for a "gas mask" for your LONG TERM BENZENE MAKING. ok???? :)

    (i SPEAK in luie of preaching part time pt bosses, slow sticker on cars etc. THE Box, and tell people such for many (8) years.) ALSO. TELL THE GOVERNEMTN YOU APPRECIATE THE BILL OF RIGHTS for the principal of it, at least!!!!.

  • Benzene forms an azetrope with water. I think you can remove the last of the water with sodium metal and than distill it again if you want to remove 7% of azetropic water.

  • @olympicfan2 There was very little water in our benzene to start with, as it wasn't in our original reaction mixture, and it isn't produced from the reaction itself. Thus, the thermometer in the still head was reading far closer to the 80.2 C boiling point of benzene than to the 69.3 C boiling point of the azeotrope. But, as you can see from the initial turbidity, there is still some water present. After drying with the anhydrous magnesium sulfate, the water, and the turbidity, disappears.

  • @ReactionFactory

    Now i'm not the mastermind of synthesizing but how pure benzene would this result in?

    Thanks

  • @ClandestinusJES Provided you redistil it, it should be around the same as 'commercially pure'.

    Benzene is quite often used in reactions which need to be done in anhydrous conditions. As benzene will form azeotropes with water, water is the main problem for those. RF dries his with some anhydrous agent, which will get rid of most of the water.

    To get it anhydrous, it needs redistilling from sodium with benzophenone and transferring with a syringe. Or use a molecular sieve.

  • @olympicfan2 ya lol

  • I wonder if you used sodium oxide or calcium oxide would it optimize the reaction to produce more biphenyl?

  • Interesting video! I especially like the ascending benzene vapors in the Vigreux column in redestillation at 2:30-2:40.

    The gunk at 3:15 contains mostly benzophenone and biphenyl.

  • @DoktorKlawonn

    Thanks! We knew that biphenyl & co. were the primary contaminants, but are still stumped as to what the red compound is.

  • @ReactionFactory Could it be iron species carried over from the initial crude distillation in the steel can?

  • @Grundalizer

    I don't think so. There are reports of others performing this reaction in different types of vessels with the same outcome.  The temperature is supposed to affect it.

  • @ReactionFactory

    May i ask you, why is that necessary to use metal retort and a copper cooler tube?

    What temp is the dry distillation goes on? Why would a glass flask brake if used as a retort?

    Thanks!!

  • @HUNTheRealMaDLaB

    I'm not sure what temperature the reaction begins at. I suspect that it would be at the melting point of sodium hydroxide. ... And that is why you can't use a glass boiling flask.  The hot, molten sodium hydroxide would thrash glass. For the same reason, you couldn't use an aluminium boiling flask. Also, I wouldn't be too happy about exposing even borosilicate glass to the kind of heat we put that can through.

  • @HUNTheRealMaDLaB "Why would a glass flask brake if used as a retort?"

    Strong bases like NaOH and KOH are one of the few things that are able to attack laboratory and quartz glass. You can dissolve borosilicate glass in molten caustic soda and such in no time.

    There is a thread you might like on Science Madness by a member called Len titled Sodium, in which he makes quite a bit of clean sodium from molten NaOH in a cell he's made from stainless and nickel sheet.

  • Well Done!! 

  • One of the simplest Benzene synths I've seen to date. As a side note. You can get those quart cans at a paint shop for like 2 bucks. They have gallon ones too. Make sure you ask for unlined cans though. If you knew that already, then I have nothing further. :)

  • Excellent reaction and method! I see youve invested in nicer distillation equipment I noticed, something ill be doing soon.

  • you can get high from sniffing that you know'

  • @fmeriqui

    The same could be said about any compound that excludes oxygen from the lungs. Except in this case, you're also getting a rich dose of a known carcinogen

  • @ReactionFactory this doesnt get you high from stopping oxygen flow.

    it gets you high for several minutes, and its definitely not from lack of oxygen

  • @fmeriqui Also cancer

  • @rseasmith fuck cancer, as long as you get high... xD

  • @fmeriqui Yeah, you'll probably be dead before cancer hits anyway. Bye :P

  • @onedudetwotube yeah!! xD

  • Why was that special home fashioned retort used? Could a regular retort be used instead?

  • @Aranwu

    The first distillation involves molten sodium hydroxide, which will eat through glass very quickly. Steel will not react with the molten hydroxide and will withstand a higher temperature than even the highest-grade borosilicate.

  • @Aranwu He probably didn't want to waste glassware unnecesary. What is left in the retort (check the end of the video) looks to be impossible to remove from a glass retort without breaking it.

  • @Aranwu It can.

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