Hazel Chem - 2017-12-30
in this video i am doing the synthesis of chloralhydrate by chlorination and direct hydration of ethanole do to the temperatures in my country the water in my lab is frozen so i can t do anything right now .... i hope you understand this music by bensound mfg hazelChem
Check pubchem, seems u wouldve benefitted from h2so4, then distill, fractionally, chloral coming off last
I just found your channel, nice work!
thx :D
Nice work, subbed. How long did this entire reaction take? A lot of people seem to have trouble with it
the chlorination took around 14h
mfg hazelChem
Its not accurate to say this is chloral hydrate, and the channel op notes this. H2so4.. needed! Pubchem.org or .com
Hmm chloral hydrate has a melting point of around 130 degrees F or 56-57 C. Not sure but it sounded like you said .2 degrees but gave no scale
i am allways using ° Celsius so it was 2°C of
mfg hazelChem
would it be easier to start with chloroform and ethanol? Similar to chlorobutanol? seems there would be an easier way with chloroform. Any response would be appreciated.
hm i dont think that this will work .... sry
mfg hazelChem
Is there any use for Chloral (trichloroacetaldehyde) or Chloral Hydrate other than a sedative?
Synthesis of 4,4′-DDT
hi, have a question: does the temperature has to be raised DURGING the chlorination? if yes, do you know why? i can't think of an explanation.
also: was your source "Winterfeld, K. - Praktikum der organisch-präparativen Pharmazeutischen Chemie"? :D would be funny
it increases the reactionspeed this interm increases the yield
mfg hazelChem
@Hazel Chem so i did this and now i am left with some emulsion. i dont relly know what i have here
it is not soluble in water
@Whopperino Beats yes in parts :D and to your emulsion problem .... i think you just have to try it again or recrystalize ..
mfg hazelChem
HAZEL..........GREAT VIDEO. You really made me think and read a lot of stuff.....lol. I could be wrong but i think you should add a little water to your reaction to help OCl anion formation and also help carbonyl hydration to form the geminal diol. Just a thought. ALSO I understand you boiled/distilled off the liquid at the end so you could concentrate the chloral hydrate and you did it under a VACUUM so it would not decompose in to chloral at it's boiling point of 96C. But if chloral hydrate boils at 96C and chloral boils at 98 C and water boils at a 100 C and ethanol at like 78C. I mean all those boiling points sound VERY CLOSE TO EACH OTHER. Maybe when you distilled it down to concentrate your product you ALSO distilled away a lot of your product. I mean just because chloral hydrate and contaminants/impurities have almost the same exact boiling point under atmospheric pressure does not mean under a vacuum the boiling points will still be close to each other. But it may be a good indicator that the boiling points are still VERY CLOSE TO EACH OTHER even under a vacuum.......... DID YOU CHECK TO MAKE SURE????????????????????????? Just a thought. Not saying i am right but i am saying it is my GUESSES. My 2 cents.....lol. Man i been at this same video and posting and researching it and watching it for over 6 hours now. I am GETTING A BRAIN CRAMP...............LMAO
hey john thanks for all the time you put into analyzing the video! I think you are right and that the final "concentration" step killed my yield. The video is now three years old and of now i would do it completely differently.... and I might do so in the future ^^
mfg hazelChem
@Hazel Chem .........Seriously watching experiments and learning the mechanisms and etc is my entertainment in life. I got nothing else going on....lol. The first time i do an experiment i think just getting it to work is a more important goal than getting a great yield. On the first attempt just getting it to work is a BIG success in my mind. Then i can try to tweek it on the next attempt so i can get a better yield.
I have trichloroacetaldehyde how do I turn it into a drinkable sedative?
by adding the right amount of H2O .... but i wouldn´t recoment taking chloral hydrate it´s easy to OD on it
stay save !
mfg hazelChem
there is nothing they can do for you with a chloral hydrate overdose either, no narcan. just pray you start breathing again
Can't i just bubble chlorine gas through vodka or something? since it has ethanol and water in it
@Hazel Chem no need to worry because even if i don't have special equipment i am some what good at chemistry and have atleast 4 years trying and doing more stuff, like once i made chlorine from electrolysis of brine and made calcium hypochlorite (in an open and ventilated area)
@Hazel Chem last question, after i did the process and i have my solution of chloral hydrate, water and maybe some alcohol how can i remove the water without boiling it, since the boiling point of chloral hydrate is 98 °C and water is 100 °C, can i put it in a dessicator? I heard that chloral hydrate is hygroscopic so i don't know if it would work
@Miguel Chacón depends on the desiccant you are using i recommend H2SO4.... but it seems to me like you want to take the product ...... do not do this ! the produced chloral hydrate is not pure and may kill you!
mfg hazelChem
@Hazel Chem any way that i could make it pure? And what type of impurities could be in the product?
@Miguel Chacón I wil not answer that because selfmade chemicals should NEVER be consumed.
mfg hazelChem
1:45 So the temperature should be raised slowly over the course of the addition of chlorine? Or would the best yield come from adding chlorine and then refluxing it for a while?
Also since anhydrous ethanol isn't a common lab reagent, does 95% azeotropic ethanol work as well or is the water content too destructive to the synthesis?
Great video by the way this is the first time I have seen someone make this before!
Reflux the 95% with CaO for a couple hours.
Das gute alte chlorhydrat. xD
What was the percentage of ethanol ? How long chlorination took ?
the EtOH was around 99.5 and the chlorination took around 7 hours
mfg hazelChem
@Hazel ChemDoes 95% ethanol work too or does water interfere with the reaction?
So you used HCl to make HCl which you then "throw away"? Wouldn't it make more sense environmentally to recirculate the HCl with a peristaltic pump? Also if you are going to react a gas with a liquid would a tall thin reaction vessel make more sense as the bubble transit time is longer? Then there is the question of why you bother to be precise with the HCl and TCCA when you are not getting 100% absorption into the ethanol? Given that why even use TCCA when you could just electrolytically produce the chlorine from NaCl? Do a run like that and weigh your product, that then gives you the reaction rate for your given set-up and conditions which means you then know exactly how long to run the next batch to get close to 100% conversion.
you are absolutly right
but the recovery of the HCl fumes is (in my case) not worth the effort ....
to the reaction vessel here.... you are right again and again i did it how i did it because it was easier to do for me with the round bottom flask
and lastly the electro chemical production of chlorine gas is quite difficult to do for an amateur eighter you need a Hg electrode or a membrane cell ... and one thing is crazy dangerous and the other is expensive
thanks for the feedback i realy appreciate it and happy new jear
mfg hazelChem
@Daniel Matthews
Also NaCl has a melting point of 800*C and electrolysis only works in a liquid, no sane person prepares chlorine via electrolysis.
If you think aqueous NaCl would work your wrong, as the following instead happens.
NaCl + 3 H2O → NaClO3 + 3 H2
I have some ideas about what I have seen on the video and in the above comments.
I agree with @Daniel Matthews on that the elimination of HCl wasn't environmentally friendly. If the recovery or recirculation is hard to accomplish, a basic solution (sodium carbonate, for instance) could be used to absorb the fumes.
About the "chlorine from NaCl electrolysis" issue, I agree with @Hazel Chem and @ClickThisToSubscribe on that the process is cumbersome and may be dangeours and expensive for an amateur chemist.
I have to disagree with @jared garden on the NaCl electrolysis. The correct would be: 6 NaCl + 6 H2O → 3 H2 + 3 Cl2 + 6 NaOH. If the chlorine can mix with the hydroxide (agitation and heating of the solution etc), then the following occurs: 3 Cl2 + 6 NaOH → 5 NaCl + NaClO3 + 3 H2O. I have prepared chlorine gas from brine a couple of times, but the process is slow and the yield very small.
When I need to perform a chlorination, I use bleaching powder in place of TCCA. It is cheap and accessible.
I like the video. Nice work, and good luck with your other experiments, @Hazel Chem.
Oh my god i have watched this video 4 or 6 times today and been thinking about it for like 6 hours. Hazel and chem player always make me think.. I think i got it. But listen to this first so you can understand where i am coming from. The hydration of formaldehyde....meaning formaldehdye in water.....will automatically make methanediol. The carbonyl will be protonated and then a water group will add to the carbonyl carbon and loose a proton making a geminal diol. If you put formaldehyde in water then 100% of it will turn into methanediol and some polymerization. The carbonyl carbon on formaldehyde is very positive due to being right next to oxygen which is such an electronegative atom it sucks up a lot of electron density from the carbonyl carbon.. And protonating the oxygen on the carbonyl makes the carbonyl carbon even more positive/reactive. But when you put acetone in water only about 1% will convert in to the geminal diol. The reason why is you no longer have 2 hydrogens on the carbonyl carbon. Now you have TWO methyl alkyl groups. Alkyl groups are (EDG) electron donating groups. For water to add to the carbonyl carbon and make the diol it must be positive. But the TWO alkyl groups are (EDG) electron donating groups so the carbonyl carbon is not as positive on acetone as it is on formaldehyde. Now most of these hydrates formed from carbonyls and water are not very stable and so can NOT be isolated. But if you have enough electron withdrawing groups (EWG) alpha to the carbonyl carbon ... like chlorine ...THREE CHLORINES TO BOOT. Then you make the carbonyl carbon so positive it has no choice but accept a water molecule attacking and making a geminal diol. And it stays stable UNLIKE most geminal diols and can be isolated because the THERE CHLORO GROUPS STABLIZE IT.
So here is my GUESS on the mechanism. Ethanol just like water self auto ionizes and one ethanol protonates another ethanol or the little bit of water in your ethanol does the protonation. But the point is you got a protonated ethanol molecule. Meaning you have a water group now instead of a hydroxy group and water groups are good leaving groups. The chlorine is bubbled in and when it hits any water molecule it turns into HOCl. Meaning there are now OCl anions in solution and that does an SN2 with the protonated ethanol molecule. The water group leaves and now you got ethane with an OCl on it instead of a OH group or water group. Next the alpha carbon is deprotonated ........the electrons from the deprotonated hydrogen jump up to form the double bond with the oxygen on the OCl group. Now the Cl is a good leaving group and when it leaves you are left with HCl gas and acetaldehdye. So you have made some water from your water leaving group leaving and some HCl and some acetaldehyde. The HCl mostly bubbles out of the pot. Now your acedaldehyde can form an enolate anion and attack the Cl2 gas and add a chloro group to the alpha hydrogen on the acetaldehyde and also making HCl as a byproduct which mostly bubbles away. Now this happens THREE times until you got tri chloro acetaldehyde. NOW WE GO BACK TO THE FIRST PARAGRAPH and remember with all those ELECTRONEGATIVE chloro groups they will suck up electron density. And make the carbonyl carbon SUPER positive and so SUPER reactive when it comes to nuvcleophiles. Even nucleophiles that are neutral like water..............................SO FIRST the lone pairs on the oxygen on the trichloroacetaldehyde is protonated making the carbonyl carbon even more positive/reactive. So water will attack the SUPER CHARGED carbonyl carbon and loose a proton making a STABLE geminal diol which is your finished product called chloral hydrate. Someone tell me what you think of my mechanism or thoughts here
sound very interesting and it all makes sense to me but I do not have the knowledge to confirm your theory
mfg hazelChem
@Hazel Chem ......Well it was fun trying to decipher it all with the mechanism. Right or wrong it sure made me think. That is why i love you and chem players videos. They FORCE me to learn a bunch of stuff. And gain a better understanding of reactions. Before your video i never even heard of chloral hydrate or chloral.
the focus on the stirbar creeped me out, combined with the robot voice
Time to get LIT
Make Deuterchloroform! But reaction of Chloral Hydrate & Sodium Deuteroxide
i dont have any deuterium I´m sory .... and its fucking expensive
mfg hazelChem
@Hazel Chem ask cody from codys lab!
why it have to recrystallized before oral dose ?
Well, you tell me.
What is the use of this chemical? What have i come across ?
Mickie finn
IF YOU ARE LUCKY YOU'LL BE MIKKY FINNED .
IN YOU'RE UNLUNCK (FROM A COMPLETELY UNRELIBLE SOURCE YOU LIVE WILL SUFFER.
Idiots those guy.... The answer for ur question is in google......hahahah
NileRed on steroids (or maybe amphetamine derivatives?)
So cool
I made this an took it. It got me high like xanax does. only cheap., take three to five grams.
please do not take any self synthesised substances !!! and if you do so recrystallize it !!!!
mfg hazelChem
I did find this mechanism but it seems rather weird. Not sure if I'd trust it.
http://www.prepchem.com/synthesis-of-chloral/
it seems quite strange because there is no HCl produced in this mechanism .... and i know old german industrial papers which did the chloralhydrate synthesis in simular way as i .....
mfg hazelChem
Well the HCl obviously has to be produced for each H that is substituted from the Ethanol it just doesn't show up in the mechanis.
hmm .... also the formation of an ether bond when the EtOH attacks the double halogenated EtOH seems pretty strange to me .... at least at this temperature ......
mfg hazelChem
Thank for sharing link! I appreciate it! 😊
Thank
That's music? It sounds like the main bearing seizing up in a Ford Pinto.
Hazel Chem - 2017-12-30
hello everybody
in this video i am performing a OTC chloral hydrate synthesis
for this i weight out three hundred and seventeen gramms of trichloroisocyanuric acid
short TCCA
as my source for the chlorine gas
after this i measured four hundret milliliters of a thirty to thirtythree percent hydrochloricacid solution out
the TCCA is then transfered into a gasgenerator setup
this step has to be done in a fumehood or with a gas mask equipt because the TCCA dust can damage your lungs
now forty six point zero seven gramms pree dried ethanole is added into the reaction flask
this amount of ethanole corresponds to exactly one mole
to start the reaction i am slowly adding the hydrochloric acid to the trichloroisocyanuric acid
this generates three mole chlorine gas out of one mole TCCA and three mole hydrochloric acid
and in this case four mole chlorine gas for our reaction
the start of the reaction is performed in an ice bath which temperature should be raised over time until boiling occures
for my attemp i just used the ice bath without raising the temperature which gave me a horrible yield as a reward
so now after you saw the initial coloring slash absorption of the chlorine in our ethanole i am going to talk a little bit about what is happening in the reaction flask
but a a warning the over all reaction is not that well known
but anyway
so as we drop the HCL to the TCCA we are generating molecular chlorine CL two gas
this then runns through the tube into the ethanole were it attacks the methyl groups hydrogens and replaces them one by one with a chlorine atom
yielding at first the mono then the di an then the tri chlorinated ethanole
and with each chlorination a molecule of hydrogenchloride
so now the problem is that the secondaqry step were the trichlorinated aldehyde is formed is not explained anywhere or at least i did not finde it then shame on me
so i can just assume that it meight be some kind of intra molecular rearrangement
here you can see the formed hydrogenchloride fuming in the humide air of my lab
i hope this shot underlines how important it is that you work in a fume hood because of the toxicity of the HCL fumes
after the chlorination has finished i simply reduced the volume by vacuum destillation to get rid of exess water and ethanole
as seen previously the chloralhydrate has allready formed do to the presence of water in the reagents so you do not need to ad anny H2O
because some of you requested that i let the lab audio in the video i did it this time
but you can clearly hear the problem
i am allways listening to music
but for the future i will try to get some music free shots with lab audio
when the boiling prety much died down i put the concentrated reaction mixture in an exicator to kristallize my product out
in the end i got two point eight gramms product of unknown quality
which is just horrible
but the melting point was only point two degrees of and the smell did fit that of chloralhydrate
so with some improvements like acidifying the reaction mixture and doing part of the chlorination in a boiling water bath the yield should be much better
so have fun and do not kill your self
Petko Tzvetkov - 2018-01-02
Great you are back with new synthesis... I really like you choices and technique! Regards!
Rajat Singla - 2019-05-08
Thank you mam for providing written notes