Chlorinating C2Cl4 to C2Cl6

Рет қаралды 34,502

8 жыл бұрын

In this video, I attempt to chlorinate tetrachloroethylene to hexachloroethane using ferric chloride as a catalyst.
Patreon link: / dougslab

Пікірлер: 90

@hardwareful 8 жыл бұрын

Maybe tilting the round bottom flask by 45 degrees moves the liquid sufficiently far away from the cold head condensor. That might work in simple setups.

@glenthemann 8 жыл бұрын

yay another nice long dougs lab :D you sir inspire me to have a lab that I cannot possibly given my current living circumstances, but I can dream

@martinprentice3225 8 жыл бұрын

Keep up the good work, its a pleasure to watch your detailed videos.

@vector8310 3 жыл бұрын

Your vids are an absolute pleasure. I pick up a thing or eight with every one I watch.

@homealchemy 8 жыл бұрын

Where is Doug? I hope he didn't get injured doing chemistry.

@gogear131 8 жыл бұрын

its been a month.....hope you didnt breathe in to many of dem chemical fumes....i love you come back T_T

@spaceyboi6651 8 жыл бұрын

Seriously we need some info about you. Hope you're not in hospital.

@ericallen1045 8 жыл бұрын

Hey Doug you should synthesize some oil for your lab jack. Haha love your vids

@jhyland87 4 жыл бұрын

Yeah, or some handy dandy WD40.

@LukeM912 8 жыл бұрын

Another awesome video as always, do you think you can make some playlists of your videos in order?

@maggincracking8174 8 жыл бұрын

Hey, I have watched a load of your videos! All of them are very interesting and informative keep it going. Quick questions, what sort of analytical equipment do you have?

@lightvsdark21 8 жыл бұрын

Where'd you go?! Come back!!!

@galacticgaming5058 8 жыл бұрын

This is amazing bro

@JadAzido 8 жыл бұрын

Where'd you go Doug? been a week since this video came out :(

@ProjektOchExperiment 8 жыл бұрын

Good video!

@valentyn.kostiuk 2 жыл бұрын

Hope you'll come back one day.

@baileymclean1021 4 жыл бұрын

Hey, Doug could you do a Friedel-craft alkylation reaction?

@pixelpatter01 7 жыл бұрын

Why didn't you tilt the two neck flask to bring the cold finger out of the solution?

@anonymouslegion1544 8 жыл бұрын

can you do a video that includes a reaction that involves an inert hydrogen atmosphere?

@vlogscience 8 жыл бұрын

Cool, i'm curious as to how you got your anhydrous ferric chloride, did you make it?

@11Rastafari11 4 жыл бұрын

could photochlorination of toluene in the gasphase be worth a try? Some toluene in a boiling flask with a long column surrounded by uv lamps followed by an air trap.

@johnblacksuperchemist2556 2 жыл бұрын

QUESTION..............I have used cold fingers and they always condense water on them. Is the water in the cold finger suppose to be above the dew point of the room to stop that???????????????

@FPSproductionsDff 8 жыл бұрын

I like the 60 FPS man!

@yanovich3234 8 жыл бұрын

Do you have plans to oil your lab jack at some point? Your videos make my dog jumpy :)

@DougsLab 8 жыл бұрын

+Ian Cunningham Ugh, you have no idea how much I want to stop that squeak! I have drenched it in grease attempting to shut it up but apparently somewhere on it something has been ground to a mirror finish that squeaks even with grease. I've tried WD-40, white lithium, and mineral oil and none of it works! I think I'm just going to avoid raising or lowering it on camera from now on. Tell your dog I'm sorry. :D

@benearhart1224 5 жыл бұрын

The pro way to do with is with chlorine radical chain reaction initiated with UV light. Just make sure to keep it cool since radical reactions can proceed quickly.

@Palerider1942 8 жыл бұрын

wouldnt it be better to use an oil bath for the sublimation? that way the walls are heated aswell throughout the process

@HeaanLasai 6 жыл бұрын

To bubble the gas into the C2Cl4 you use a small glass tube. What is that piece of glassware called?

@skyhawk551 8 жыл бұрын

what if you set up a recycling system that pumped the escaped chlorine back through the reaction to improve the efficiency?

@aaronskoy957 11 ай бұрын

Good stuff! Grease on the joints may help with the loss :)

@johnblacksuperchemist2556 2 жыл бұрын

GREAT VIDEO..........I thought you were just going to put iron wool in the pot and make the anhydrous FeCl3 in situ. Man you got a LOT of anhydrous FeCl3. This is the only experiment i have seen FeCl3 be used other than in electrophilic halogenation of benzene and of course friedel crafts reactions

@DrozGodhammer 6 жыл бұрын

next, do Crystal Meth, or maybe... cook some Krokodil. I think you should make this into a three- part series, so after Krokodil, maybe you can do Jenkem?

@damiangruenberg7097 8 жыл бұрын

awaiting new videos!!!

@IndomitablegamingYT 8 жыл бұрын

where do you buy your glass ware?

@martinprentice3225 8 жыл бұрын

hi doug. could u make a video on the synthesis of titanium lV chloride if its possible . cheers

@beanlets 7 жыл бұрын

how do you make it???

@kylecrane5751 2 жыл бұрын

why not filter it with water to remove the FeCl3 first since the solubility is higher for it than it is C2Cl6?

@bpark10001 5 жыл бұрын

Why don't you use a fractionating column? Do they azeotrope? Regarding the chlorine, why not have a closed system but with a yielding member (balloon? pneumatic trough?) to store the unreacted chlorine. You would regulate chlorine additions to keep the trough partly full. You would have real-time knowledge of the reaction rate. (You would need to purge the air out of the system by starting the chlorine up early, before closing up the system).

@TheChemistryShack 8 жыл бұрын

At 6:37, hexachloroethane is about 1.3 times as dense as tetrachloroethane (at least according to wikipedia), so this is probably the major cause of the decreasing liquid level. Also, don't chlorine and ammonia produce traces of chloramine?

@praspurgh 8 жыл бұрын

+TheChemistryShack chloramine would react with water

@DougsLab 8 жыл бұрын

+TheChemistryShack Thank you for clarifying that. I didn't have time to look that up while I was tending to the chlorine generator! And yes, ammonia and chlorine do form some things other than ammonium chloride. Chlorine dissolves in water to form hydrochloric and hypochlorous acids. The HCl reacts with ammonia to form ammonium chloride, and the hypochlorous acid reacts to form chloramines, which tend to decompose rapidly to ammonium chloride, nitrogen, hydrazine, and oxygen. The addition of further chlorine easily oxidizes the hydrazine and chloamines to nitrogen, HCl, and ammonium chloride. Ammonia's volatility makes it an excellent choice for scrubbing chlorine, but is not suitable if the exit gas is not routed to a hood because small amounts of hazardous byproducts are released. However, it is very effective at absorbing large amounts of chlorine rapidly, is extremely cheap, and does not attack the vinyl hose like a NaOH solution, which is why I used it here.

@TheChemistryShack 8 жыл бұрын

Doug's Lab Oh...that's why my NaOH chlorine traps have been destroying my vinyl tubing! No wonder!

@kirea6762 8 жыл бұрын

+Doug's Lab The difference in density is actually not relevant. It's the molarity that matters in this case since the number of moles is expected to remain constant while the mass is expected to increase due to the chlorine being incorporated into the product. The molarity of tetrachloroethylene is 1622 g/l / 156.82 g/mol = 10.3 mol/l and the molarity of hexachloroethane is 2091 g/l / 236.74 g/mol = 8.8 mol/l, so the volume should actually _increase_ under ideal conditions. I suppose the loss of material is caused be tetracholorothylene vapor being carried away by the stream of chorine gas. This could be mitigated by using a more efficient condenser and/or reducing the flow rate.

@govindrao5249 8 жыл бұрын

hi i want to know chemical rice toucher how to build and what chemical use and method pls i dont know how to ( copper coin A Rice Puller is ‘anti-electricity.’ Rice Pullers interfere with electronic & electrical items. It is very important to protect electronic & electrical items from Rice Pullers) any idea pls i u have any idea pls mail me govind4web@gmail.com

@user-sz6hq8ts4v 8 жыл бұрын

what do you think about reaction between CCl4 and Zinc in neutral solvent or without solwent? Maybe its more easier?

@marcingoawski9305 8 жыл бұрын

It's very hard to do without CCl4.

5 жыл бұрын

marcin is that what he asked?

@andrewdavis5386 7 жыл бұрын

Environmental concerns noted, my question is: would one smoke bomb with that small amount really have been that hazardous and contaminating?

@DougsLab 7 жыл бұрын

Hi Andrew - Valid question, and no, not really at all. It's just that if I did do it, every comment on this video would be people freaking out and threatening to report me to the EPA.

@andrewdavis5386 7 жыл бұрын

Doug's Lab I completely understand. Love your channel. I just ordered my first set of real chemistry glassware. Going to start nice and slow. Your channel has been very educational and helpful. Keep up the great work!

@jhyland87 3 жыл бұрын

So I have all the required chemicals and glassware (mostly) to give this synthesis a shot - Does anyone know any other uses for _hexachloroethane_ other than the smoke bombs? Can it maybe be converted into _carbon tetrachloride?_ That could be useful.

@jhyland87 2 жыл бұрын

@@Paonporteur I haven't gotten to this yet >_< sorry

@dennisyoung4631 10 ай бұрын

Degassing molten aluminum. Molten aluminum has an appetite for hydrogen, and Hexachloroethane is (was) used to degass it - so the resulting castings are not porous.

@One2rock 8 жыл бұрын

a little off the subject, but do you know how to , and could you do a video on how to make pentanol? why is it so expensive now? they want like 180 buck for a liter, I think it is because they want the rush popper market shored up, but it cant be that hard to make is it??? and what is the difference in 1 pentanol, and 3 pentanol?

@transgayatheistmarijuanasm803 8 жыл бұрын

Pentanol, and alcohols in general are obtained from fermentation. Pentanol doesn't have that many uses so it isn't produced on mass scales to make it cheap like ethanol. The 1 and 3 are the position of the OH on pentanol. 1 pentanol has the OH on the first carbon, 3 pentanol has it on the third.

@One2rock 8 жыл бұрын

so how do you make it? and thanks on why it so hard t find. an no I'm not a chemistry scholar, just dabbler, so ya I need it broken down in simple ways.

@mmmhorsesteaks 8 жыл бұрын

+One2rock Depends on what you have available. You could reduce valeric acid with lithium aluminum hydride or borane; or you could hydrate n-pentene with borane and workup with peroxide (if you would use pentene and aqueous acid, you would get 2-pentanol - Markownikoff's rule). This is pretty basic organic chemistry, but the precursors are not readily available either. The most realistic approach would probably be the hydrolysis of a pentyl ester with aqueous NaOH: amyl acetate and pentyl butyrate seem to be fairly common chemicals.

@JustinKoenigSilica 6 жыл бұрын

Trans Gay Atheist Marijuana Smoker pretty sure he wanted to know the difference in production between 1 and 3 pentanol.

@moosehead4497 8 жыл бұрын

What size glass tubing are you using? 12mm? I need to purchase some tubing, the kind I have currently is too small

@DougsLab 8 жыл бұрын

+moosehead I use 6mm OD glass tubing. It's about the same size as a thermometer, so I can use thermometer adapters as gas delivery tubes.

@moosehead4497 8 жыл бұрын

awesome thanks very much

@moosehead4497 8 жыл бұрын

+Doug's Lab while im here, what size stopper fits your drying tube? I have the same one

@flaplaya 7 жыл бұрын

Moose. Dude do you not have a set of calipers or even a ruler?

@moosehead4497 7 жыл бұрын

ah i think i asked this question when the tube was still in shipping, so I couldn`t measure directly, but no worries I found one that fits snug, dries gas great heh

@lucasmaugeri5372 8 жыл бұрын

(Doug, are you OK?) (will you tell us that you're OK) (there's a sign in the fumehood) (that you breathed in something nasty Douggie) (help came into your apartment) (found you coughing on the carpet) (then you ran into the showers) (you were poisoned) (it was your doom) (Doug, are you OK?) (so, Douggie, are you OK?) (are you OK Douggie?) (you've been hit by) (you've been struck by A brewed chemical)

@cravenmoorehead7099 3 жыл бұрын

Doug sounds like Jon Hamm

@ib9rt 8 жыл бұрын

I think you wasted a lot of chlorine there. Better contact between the chlorine gas and the reacting liquid might be beneficial. Some ideas include bubbling the chlorine through a sparger to make many smaller bubbles, increasing the depth of liquid above the chlorine inlet to give longer contact time, and stirring the liquid to bring more liquid in contact with the bubble surfaces.

5 жыл бұрын

I'm waiting for people to invent airtight chemical apparatuses

@RealBadWolf 8 жыл бұрын

make a video on how to make 70% hydrogen peroxide from scratch.

@AugustusOakstar 4 жыл бұрын

BadWo1f greetings from TX! H2O2 is easily made from the 3% it comes in 1000ml bottles. Pour it into a absolutely clean 2000ml beaker and put it on a hot plate set at 50 deg C and have a fan in the same place and slowly the H2O will distill off, leaving the H2O2 that boils at over 130 C. The solution goes over about 4 to 5 hours leaving 100% of approx 24 mls. I stop at 50mls of 50% costs about $ 0.88 US. Bye

@psycronizer 8 жыл бұрын

why do you need a lewis acid for this? if bromine in carbon tetrachloride can take dibromoethene all the way to the saturated product, and chlorine itself is a bit more lively than bromine...?

@Chem-iu5jx 7 жыл бұрын

psycronizer You need it to polarize the cl2 so sou can do an electrophilic addition at the double bond

@JustinKoenigSilica 6 жыл бұрын

JOHN BLACK SUPER CHEMIST can you stop talking like...................................... this? Seriously, no one fucking talks like that in real life.

@nuclearthreat545 8 жыл бұрын

science!

@marcingoawski9305 8 жыл бұрын

Ammonia and Cl2? Are you serious? Have you heard of NCl3 and NH4ClO3?

@pinsirka 8 жыл бұрын

+Marcin Goławski Co to jest? Powstaje to w tej reakcji?

@marcingoawski9305 8 жыл бұрын

To dwie substancje o skłonnościach do spontanicznego wybuchu. Może (Może!) w tym wypadku chloru wypływającego z aparatu do kolby z NH3 jest zbyt mało by powstały znaczne ich ilości, to jednak nigdy (w niekontrolowanych warunkach) nie należy mieszać amoniaku i chloru/podchlorynów/chloranów/poddawać NH4Cl elektrolizie, by uniknąć wypadków. Obie substancje mogą powstawać gdy chlorujemy amoniak.

@pinsirka 8 жыл бұрын

+Marcin Goławski Nigdy o tym nie wiedziałem, dziękuję, uwielbiam w taki sposób zdobywać wiedzę :D

@jhyland87 5 жыл бұрын

Doug - you should make a video list of experiments/extractions/reactions that are ideal for hobbyists and chemistry enthusiasts like myself to do :-D Not too advanced, but also not so basic that they're boring... Just an idea. Love your channel!

@jhyland87 5 жыл бұрын

P.S. post some chromotography stuff... Maybe a chromotography column purification followed up by a TLC analysis? Thats what im getting into. Really neat stuff!