Hazel Chem - 2016-05-16
Today I'm synthesising chloro acedic acid via direct chlorination of the alpha bounded acedic acid. I used 100g tcca, 101g acedic acid, 10g sulfur and roughly 160ml HCl.
What was your yield?
Reaction real time
Can you make a video on how to make a shear thinning liquid polymer I was going to use tomatoe sauce but I need like 20 litres of the stuff and i don't want to waste
Did you obtain any side products as in di and trichloroacetic acid?
Thank you
Very good video, you helped me a lot, thanks.
Hi! Please tell me one thing. Did you "chlorinated" your lab with this process? I can see that the reflux cooler is not clogged. How do you eliminate superfulous chlorine gas? Thanks :)
well for exces cl2 there is the fumehood ;D hope that answers your question
mfg hazelChem
OH MY GOD I AM SUCH AN IDIOT............LOL. I kept wandering what you were doing and why it did not make any sense and then i realized you are not making chloracetone but chloroacetic acid. At first i was like well making he is making the chloroacetic acid to react with the acetone in some way but i just could not understand how........lol
مساء الخير ما هي المواد التي يمكن ان تعيد لون زيت السياره المستعمل الئ لونه الاصفر
Is the reaction better when you use red phosporus instead of sulfur?
Careful with the red P, instead of a radicalic substitution you'll end up with a SN2. Instead of chloroacetic acid you'll get acetyl chloride, this reaction also produces some traces of that, that's why water washing your product is a must, apart from making it easier to clean it.
I swear to god, half of the chemistry I know is just how to clean dirty reaction products...
QUESTION..........I have to go to work but i would like to add a some what unrelated question on making bromoacetone. I am going to put some acetone and Br2 in a pot and drip AcOH acid on it. The problem is the acid i choose (AcOH) has a boiling point close to the product (bromoacetone). So my question is this. When the reaction is done can i pour some aqueous NaHCO3 in the pot to neutralize the acetic acid and partition with ether/dcm. to get the product.........OR OR will the addition of NaHCO3 do the same thing as adding NaOH and alpha deprotonate the bromoacetone and do an aldol reaction with another bromoacetone.???????????????????????????????????? Or if there is any bromine in there and i add NaHCO3 would that be a strong enough base to cause a haloform reaction???????????? Or should i just NOT try to neutrallize the acetic acid and extract out my product (bromoacetone) with dcm or ether or whatever and then just do some multiple small water washes and hope i get it all out from that and distillation using a vigorex column???????????????????? Or maybe i should just throw a couple mL of sulfuric acid in to make my enols instead of acetic acid.?????????????? That way sulfuric acid has such a high boiling point i could just use distillation to separate it from the bromoacetone?????????????
Professional, very nice. I need to see if I have the glassware to dry my chlorine.
you dont necessarily have to dry the chlorine .... but if you dont dry it the workup is more work intensive
mfg hazelChem
A tube with CaCl2 will also work.
GREAT VIDEO............After I watched it 3 times i realized i read the title wrong and was confused the whole time. But after i realized you were making chloroacetic acid it all made sense. I have to look in to that sulfur thing. That is new to me.
hello John ^^
thx for the comments and the nice feedback. Well that misreading thing happens to the best XD
I once watched a chemplayer (may they rest in piece) video and utterly misread the title which lead me to believe that either they are idiots or I am.... turned out that 2 hours of sleep for a prolonged time made me the idiot XD
have a nice day and do not kill yourself
Can I fluorination acetic acid like that ? Will it produce fluoroacetic acid ?
nathan is right ! i made HCN but not even i am thinking about using F2 or HF !
mfg hazelChem
GREAT VIDEO .......Going to watch ALL your videos in chronological order they came out. One down. A bunch to go. Not sure what "clocked" means but i am guessing you broke your frit sintered glass funnel and threw it away??????????????????????? I keep my stuff i break now in case i can use it later. I plan on using the frit from my broken funnels for a membrane/salt bridge in electrolysis experiments
nice idea with the electrolysis! until like two years i am also keeping my broken glass comes in handy quite often
mfg hazelChem
It'd be better if you could show the components and other things as text during the video
Very nice Video man, are there still other vids to come? if yes please synthesis of nitromethane
there will be more videos butt i have to get used to my new audio equipment for recording the audio lines ... so im verry sorry fore the longe time without videos
to the MeNO2 i´m working on a reaktor to direktly nitrite the methane gas
if this is not working i have a backup plan wich involves sodiummethylsulfate :p
mfg hazelChem
Hazel Chem
nice, but I dont think that the sodiummethylsulfate method would work very well, looking at the sodiumethylsulfate-way to get some nitroethane
p.s. Den combimag hab ich auch ;-)
MfG
a.s.
@Hazel Chem any followup? :D
@John Griffin well there is the problem of the reactor selfdestructing .... and i have to make more Cl-Ac-COOH and no time ..... but some day !
mfg hazelChem
Oh no don't throw this neat peace of glass away :0 You can easily dissolve the sulfur in toluol/xylen.
As far as i know the sulfur catalyzed prozess also forms acetyl chloride, so you maybe have to distill it.
Really enjoyed your video, keep it up!
p.s.: Ich hab da so eine leise Vermutung, dass deutsch deine Muttersprache ist :)
stimmt
@Felix Schach .
Yes, hot xylene works great! But put a filter paper on top of your frit next time, and it won't get clogged so easily.
QUESTION................So is this a free radical reaction?????????? I mean you are making free radical chlorine and it grabs the alpha hydrogen off the acetic acid and then the acetic acid free radical grabs a chlorine form Cl2 gas and that makes a free radical chlorine to repeat the cycle.. ................But you said there is an acetic anhydride intermediate????????????????????????????????? What is actually going on there?????????? I mean does the sulfur help make acetic anhydride and that is what is being chlorinated and then it decomposes into chloroacetic acid when you add water at the end???????????????????
Couldn't you just electrolyze brine solution, and run the resulting chlorine through the glacial acetic acid for a few days? That would likely be cheaper (using salt), cleaner & if the power is set right you can probably focus on recycling more chlorine back into the solution.
well you would have to build a chloro alkaline electrolysis cell and the output would be quite small
but it is an alternative. For the first part I do not think that, in the conditions you are proposing, the reaction will take place.
mfg hazelChem
ok I had some fear to embarrass my self by telling chmical bullshit .... but i´ll give it a try
this reaction proceeds largely by the Hell Volhard Zelinski mechanism which is normally catalysed by a phosphoroustribromide at a bromination or a phosphorustrichloride at a chlorination. Since I have however used sulfur in this case there are two posible catalytic effects
1 the sulfur alone catalyzes by resonance effects ( you can read this up in the "Organicum 24 Auflage s.160)
2 the sulfur forms sulfurchlorides which then chlorinatethe carboxylic acid
my problem in this case is that I do not know why the chlorine atom replaces the CH3 group and not just one of the alpha constant hydrogen atoms
if someone can explane this please write it in the coments
+Superherofrosch oh ja you´r right :D thanks for helping me out
I will advise your channel to view other people.
What is happening in your video should be clear to everyone!
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Please indicate on the screen in writing.
in the form of formulas and mass of matter - your every action.
otherwise it is not clear.
not understand.
we have other language.
thank you.
This machine translation - Google!
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which substances you use?
and in what quantity?
TCCA -what is that?
Trichloroisocyanuric acid
I'm happy to take up your suggestions #johnblack and I am definitely making to each of your ideas (that is possible for me) a video.
However, I need to check the legal position because some of them are very often used in the preparation of many illegal drugs for example the metal hydrides as reducing agents.
MY BASIC RULE
When a viewer asks me for a theme, I'll make a video to it and try to explain the mechanism.
No matter how controversial, dangerous or difficult it is
BUT
It must be within the law
I am often taking significantly longer with toxic, carcinogenic or groundwater hazardous materials on a video, because I look very strong on self-protection and the legal position
Hi man! Your videos show a man of a great exercise and knowage and I'm really happy to watch and have them... One question - what will be the effect of an IR (infra-red) lamp on the reaction?? Can it replace or overcome the halogen lamp??
Hi man! You have great videos and I'm sad you've quit posting new ones... I wanted to ask you - I have an demonstrational ultra-red lamp (infra-red). Will it speed up the chlorination (halogination)???
sorry that i am responding that late ....
so you need very high energetic photons to split the chlorine molecules
for this UV light is the best and infra red the worst ....do to te wave lenght and the wave particles dualism that gives you the corresponding energy to every wave lenght ... i even doubt that it will work at all if you are using the IR light ....
mfg hazelChem
@Hazel Chem what about using soalr concentrator instead of UV lamp ?
@Lead Azide&Base can work but not as good as the UV lamp
mfg hazelChem
JOHN BLACK SUPER CHEMIST - 2020-07-20
Hazel Chem..........I stopped watching other peoples videos for years but i am back at it again. I been watching like 4 other videos where they make chloroacetone and they NEVER add any acid catalyst (AcOH). I asked them all why but i doubt they will respond. BAMM right off the bat i see you getting AcOH. I looked down and i see it is my HERO Hazel Chem the REAL super chemist. Of course YOU are doing it right. I am VERY GLAD you are still around making videos. Just wanted to say hi AND GREAT VIDEO even though i haven't watched it yet i know it is great