@@redram5150 solvents have became very expensive due to the governments heavy regulations for them. 40 for a liter of dcm seems reasonable and it isn't that small..
Doug I love the way you do your videos, so informative and you give all the reasons why you should do things safely and how to do them. Thanks for making them.
Just to eloborate on the point Nils Rotthowe made, the carbon is sp3 hybridized in CH2Cl2 and thus tetrahedral in shape. Due to the shape of DCM and the dipole moment of the C-Cl bond it s a kinda polar molecule that just doesn't mix with water. For example, the dipole moment (mew) for DCM is 1.55 and for isopropyl alchol mew is1.66. Keep up the good work, love the videos.
DCM is polar because of its tetrahedral shape. There are no opposite sides for the Cl to be on. The angle between each of the 4 substituents is 109.5 degrees
Erwin Rommel not exactly. The two chlorines are bigger, and therefore there's a slightly wider angle between them and a slightly narrower angle between the hydrognes. But approximately the angles are somewhere in between 109° and 110°.
Just to elaborate on this point (i know the comment is 5 years old, but in case anyone new sees this). The main reason the dcm is not miscible with water is due to the lack of ability of water to form hydrogen bonds with it. If you look at other organic molecules of a similar size then the ones that CAN mix with water are those which have a nitrogen or oxygen in the molecule - a place where the water can hydrogen bond to. For example aldehydes cannot hydrogen bond within themselves (as the oxygen is not directly bonded to a hydrogen), but water can hydrogen bond to the =O DCM definitely shows some polarity and this can partly explain the relatively high boiling point of DCM as opposed to the first few alkanes.
You can see how much methanol was in the distillate. At 6:43 the water layer extends just to the bottom of the label "500 ml", whereas at 7:46 the water-methanol layer extends well below the label "500 ml".
That so called polymer goop might be methyl cellulose, I don't know how you could test for it or what you could do with it though. What's with the 1,3 benzodioxole in the last scene? I can't help wondering how nice it would look with n-methyl-propan-2-amine attached in the 5 position...
Was wondering that myself as well... or maybe attaching an indane ring with a secondary amine. I also wonder if you could change the (secondary?) amine to a (tertiary?) amine and hang a L-lysine off the nitrogen in the indane ring to create a slow release version.
Methyl celulose can be used to make metaloxide nano/micro particle paste to make electrodes from particles in dye sensitized solar cell experiments. I believe that there are many other similar uses.
Dichloromethane is not hugely soluble in water, but it is somewhat polar (moreso than diethyl ether) and it will dissolve to the tune of a few tens of grams per liter of water (or vice versa for water in DCM), depending on the temperature. I understand that the intent of this video was to show an easy way to acquire a useful solvent (and it did a good job of that) but the simplification might have been excessive.
You can pour methanol/ethanol/isopropynol into the stripper after it's mostly distilled to continue the distillation for a slightly increased yield, however there still needs to be some leftover DCM for the polymer to not crash out.
The whiteboard, that three,four methylenedioxy skeleton with a cho tacked on is the precursor to a very substantially valuable, truly mind opening substance that is worth taking. And synthesizing it then becomes why you begin learning organic. Come to find life is deep and science is what its about!
I love your videos and it's always great to see what kind of chemicals you can actually get OTC. But your representation of the CH2Cl2 structure is a bit off. The way you told it, the carbon would be square planar but since it's sp3 DCM has a tetrahedral structure so there isn't really something like "on opposite sides". Keep the expensive videos coming so my patreon account comes to good use ;)
+Nils Rotthowe It's easy to tell people with real chemistry knowledge apart isn't it. Some of the things I see people say on the internet make me have a good giggle:)
Actually, I did that on purpose to simplify the explanation. I didn't want to have to spend time explaining 3D structural representations since most people watching this video are just trying to get DCM.
+Nils Rotthowe + Dr. Heisenberg I do feel badly that this might teach someone incorrect information. The thought process was that most people who are looking to isolate DCM from OTC products are not chemists - they're modelmakers, auto enthusiasts, painters, etc. and in the past I have received negative feedback about long, boring explanations. I resolved to simplify explanations on the simple videos, and maintain the full explanation on the complicated syntheses that only chemists would really be interested in. Unfortunately, I then get critiqued the other way, with the chemists telling me the explanation is too simple/technically incorrect. I'm trying to find a balance where I can give enough information inspire the curious to seek more information, while still keeping things short enough to appease those who are not chemists. It's difficult!
Good science Doug. Love the channel. I didn't have any potassium carbonate so I distilled. Also I took the initial distillation a little further, got "the goop" out. Then I evaporated the remaining solvent out of said goop. I'm 99% certain that what's left is nearly pure polysilicon. This stuff is a great additive to lubricants and is very chemical resistant. It's primarily made by Dow Corning in Michigan. Play around with it and see what you think, I'm definitely greasing up my saucer sled with the stuff this winter... I mean it's REAALLLY SLICK.
Ik its a joke but between ace home depot/lowes and once in a blue moon tractor supply ive been able to find everything he gets at the hardware store it just takes alot of lable reading
+Doug's Lab you should have used a larger sep funnel because it was too full giving the DCM smaller surface area making the washing steps less effective
I guess u need to study some chemistry dude... due to the high electron withdrawing nature(electronegetivity), the bond angles get changed and it doesnt remain tetrahedral..it changes to kind of a see-saw shape
@@venkatsharma05it absolutely remains tetrahedral, it’s just not as close to ideal as methane. Methane bond angles are 109.5 degrees, DCM cl-c-cl bond angle is 112.2 degrees, less than 3 degrees from an ideal tetrahedron and almost 70 degrees from the 180 degrees characteristic of a see-saw.
Okay this has been confusing me for awhile now. The central carbon is sp3 hybridized yes? Meaning it forms a tetrahedral shape with its bonds. This would mean that there is no "opposite side" for the chlorines to bond to seeing as all of the bond angles are identical. Now I am aware that steric interactions are going to cause the chlorines to repel each other, but is this really strong enough to consider the two adjacent bonds as being "opposite"? This maybe just a slip of the tongue on your part (if you're Doug currently reading this), but as a student I just want to clarify for my own understanding. -Thanks
@@mikeg4972 agree, but the synthesis of DCM is not easy and not attainable by the amateur. It requires chlorine gas, methane and temperatures sbove 500c.
how pure would this be? how far from pure would it be for use in extracting cinnamaldehyde via distillation and then used as a fragrance (i.e. comes in contact with skin or inhalation)
after watching this, i went and researched how DCM is made and it went as far as learning how to concentrate CO2 from atmo using potassium hydroxide and calcium hydroxide, then turning the captured CO2 into methane using the Bosch reaction, and then chlorinating the methane into DCM at 400 C. fun stuff. side product is HCl which is useful
+skyhawk551 i plan on making my own liquid salt reactor to make sodium metal and chlorine gas so i will do this for sure. besides i don't want to waste chlorine gas and there's only so much HCl i can make.
+TheTechnic Lord I have but I don't get chlorine gas from it, and I wanted to get sodium as cheap as I can and water softening pellets is the cheapest source I could find. besides I plan on getting into metallurgy so I won't be bothered by high temp. :) I will have a proper lab before getting started
skyhawk551 Ahh, getting into metallurgy too I see. I too wish I could, but unfortunately my lab consists of a kitchen, a broken beaker and a few flasks :P. I did melt salt and aluminium though, so I guess that's something. Any way I can help (I know the theory :P)?
+TheTechnic Lord I'm going to make an electric furnace that uses tungsten wire to heat it so I can go to 4000°F using zircon crucibles/linings. I would like to make my own graphite but that requires plasma arc heating to pull off
In the beginning when you said you wouldn't need the thermometer because it wouldn't tell you anything: wouldn't it be handy to know what temp. the vapors are at so you know what's distilling over? I know methanol has a much higher boiling point than DCM, so why wouldn't that be a good thing to know?
Why do the methanol separation in the sep funnel? Seems tedious. Why not do it in a large Erlenmyer w/ a stir bar and copious water, with the sep-funnel only for separating the layers?
Outside of heating, is there any way to turn dichloromethane into something less toxic or neutralize it to be less of a hazardous material? There is some MC/HF acid-based paint stripper leftover from a tenant and I was curious about either putting small amounts onto a tray on a hot day or reacting it with something "neutralize" it. Thanks for the video!
It's still heating it, but toss cup fulls of it at a time into a big roaring fire, the elevated temperatures will allow it to burn which will destroy the molecules. Or take it to a hazardous waste drop off site, there's always that. DCM won't burn on it's own (it burns, but it's not a self-sustaining reaction since the flame temperature is lower than it's ignition temperature) but a big roaring fire with hot coals will safely break it down just fine. Adding chemicals to neutralize it will probably wind up with a more toxic chemical soup than you started with...
@@TheExplosiveGuyBurning chloroalcanes is in general a big no. You could make some extremely deadly phosgene in this way. Now, as it is dichloromethane and not chloroform you'll mostly end up with formyl monochloride instead (which decomposes rapidly to hydrochloric acid and carbon monoxide), but I still wouldn't take the risk. Slowly evaporating the stuff is the best way on a small scale. Strongly alkaline water solution will slowly decompose the stuff in a few months and is suitable too.
Hi Doug. We have purchased pure Dichloromethane for a solution of paint stripping, we will try to keep it enclosed to stop evaporation as it will do it simply on a hot day. Is there any other solution we should mix with the DCM to make it a better product for our shop, we will strip parts by immersion, not by spraying in the open air. Thanks
You are missing things like once you didn't suply nitrogen during distillation and always use molecular sieves to store DCM longer.. P2O5 already absorbs water so no need to do separation further via funnel.
A question. is it possible to rebuild the cap of the can and use the entire can as a disposable boiling vessel to get as much yield without a messy cleanup? or is there a good reason like possible contamination that can occur?
Late reply, but yes you can, the distillation temperature is so low you won't need to worry about any side reactions with the metal can or it's plastic fittings (unless it's all steel). It's really not a bad idea honestly, you'll save a number of steps and can just cap the remnants in the original can for disposal.
@@TheExplosiveGuy I use that method to isolate & purify most of my solvents. Coleman's camp fuel (et al), yields Hexanes, & the metal spout, will accept the male 24/40 after multiple wraps of Teflon plumbers tape and pressing into the opening. The Hexanes have BPs from 40^C up to to 105^C. The bulk is about 60^C. I use a vigreaux to separate the various cuts on the first pass. You do nice work. I like the Handle. I am a former licensed fireworks supervisor. I "get it".
@@Don_Soucy It's a good method, why waste time and dirty up glassware when it comes in It's own boiling flask lol. And thanks, I appreciate the compliments, I haven't put as much time into my channel as I'd like to but eventually plan to do a lot more, and I'm definitely getting back to the pyro roots that my channel was originally based on (I made the channel in like 07 I think, back when I was making a lot of primaries as a hobby😉), though HPR rocket building is starting to overshadow everything else now haha, I just built my first APCP level 2 HPR rocket a few weeks ago including motor and fuel and now all I can think about is getting my class 3 lol.
Any advice on what to clean the BF with if one waited too long to remove the residue whilst hot and still somewhat fluidy? NaOH solution work okay? Ive done this before it works quite well, so thank you Doug (i love all of your work brother, please keep it up👍🏻👍🏻) , but last time i was smart enough to remove the residue rather quickly. But say one waited too long and the residue lost its fluidity and began to cake on the flask?
Any idea what polymer is in the polymeric goop? Maybe a polystyrenic type, maybe some byproduct of styrene production. On a similar note: PVC glue is a good source of THF, it is thickened by PCV dissolved in the THF.
+GEZZA1 Distillation as with DCM. Take care - pure THF forms peroxides that can ruin your whole day. Since the polymer is PVC you might ruin a flask too.
+Jk Smith -- It's almost certainly methyl cellulose, a methyl ether of cellulose. It's also used as wallpaper paste. See: en.wikipedia.org/wiki/Methyl_cellulose
If you're in the US in 2020 looking for DCM in the hardware store, you're going to have a hard time finding it - the EPA just banned DCM in commercial products.
I hate to be a wet blanket but you can buy laboratory grade methylene chloride or dichloromethane from Carolina chemical supplier for about $11 for 500 ml. Last I checked that can of klean strip you used was about $25 at Lowe's You stated you wanted to have this on hand because it's a very convenient solvent to have on hand for many reactions so it seems a little bit of a waste to perform this reaction. I could see doing it if you had maybe a half a can leftover because it does not store well to just have the solvent on hand it's much cheaper to buy it from a company like sigma or Carolina
Have you tried ordering it from sigma or Carolina chemical? Good luck getting it without working for a large lab or company. This video was made for people who can't order chems from those companies.
I love your work Doug, please keep it up 👍🏻👍🏻 Any advice on what to clean a BF with, if one waited too long to remove the residuals and they began to dry and cake the walls of the flask?
Just hook the rubbery residue with a bent bit of wire and drag it out through the neck of the flask, then clean flask with a brush and a bit of acetone.
The flooring business uses DCM mix to clean carpet glue off tools and the edges of the carpet. I'm fairly sure the most common product I used had the polymeric goop and DCM w/o methanol. Just another source if any other floor-installers/amateur chemists have some laying around. I forget the number commonly assigned to the compound. - TVC
Thanks for your very informative videos. I really enjoyed watching them! I am just curious, are you working without a mask and a fumehood? As it was a moment when you hold a flask with methanol+dichloromethane, flask was open. So you could simply breath vapors which are toxic, expecially from methanol?
Hey could someone please tell me how/if you can separate petroleum and methylene chloride, there’s a local paint striper here that contains methylene chloride but also petrol and I Seen they have similar boiling points
Lol i had no idea about the recent ban of DCM in consumer (but not commerical) by the EPA until i needed some DCM and found no products containing it or advertising it as NMP or methylene chloride free. I went to a few hardware stores to check and even the brand that I used to use, changed it's formula... Even Klean Strip changed theirs...
+MrIhavnovideos that does not look like o-dinitrobenzene, can't see it very well but the benzene ring has a 1,2 oxygen bond and o-dinitrobenzene would have NO2 on 1 and 2. But the bottom structure clearly is 1,3-benzodioxole
DCM is gone from all shelves as of 1/1/2020. Very unfortunate this video is now obsolete as I literally just planned on isolating some. Better stock up on most types of store bought solvents. MEK is another along with Xylene for that matter that are gone now too :(
Doug, I have a rather beginner question that I hope you will answer. If one were to have a 2L sized heating mantle with magnetic stirring option, would I be able to also use smaller boiling flasks ( 1L, 500ml 250ml) in the 2L sized mantle??? I see so many different kinds of mantles in different sizes, I was hoping to not have to buy more than 1. or perhaps would having a big hot plate with stirrer be better, in conjunction with an oil bath? Please let me know when convenient, thank you for your excellent videos, I’ve learned so much! -alex
This may be two years late, but yeah you can use smaller flasks in bigger mantles if you need to, it's always an option. Obviously you won't be able to match the heat transference to the bottom of the flask due to less contact area but it really doesn't matter, since a 2 liter mantle can put out some serious juice, it will heat perfectly fine. I get by with just a 1 liter mantle and a Corning PC-351 600W hot plate, if the mantle won't fit my vessel then an oil bath on the hot plate will. I do think it would be pretty nice to have the full range of mantles though, perhaps one day when my hobbies and budget align lol.
haha better late than never! thx for the reply though bro, just saw it as I’m not on here as much I appreciate the feedback, I’m a super noob on a budget, so I’m glad to hear a 2L mantle will work just fine for smaller flasks Thx again for the help man!👍🏼
How do you get the dichloromethane with the two Cl on one side? I mean you have described the 1,3 dichloromethane which is non-polar, but I would love to have the 1,2 dichloromethane which is polar🤔
The left over polymer crap in the boiling flask is problematic in its removal. I read someplace or saw something that said that kerosene will remove it. When I used kerosene to try and remove it , it did not work. I used some tetrachloromethane (aka Brakekleen) in its can and that sorta worked but still didn't break it down very well. I finally used some very hot water and Dawn dish soap which helped but I still had specs of that shit stuck to the sides of the flask. I got it out finally by mixing up about two tablespoons of sodium hydroxide in cold water, and let it set for a couple of hours. Btw, HCL never phased it either. I also used Kleanstrip paint stripper. My can of it was almost straight DCM and no methanol. I washed it with water and couldn't extract any methanol from the wash water. Not to say it didn't contain any, just that the percentage in it was very low. This is a great video, I'm just relating my experience with this process. The problems with videos like these is that the makers of them leave out some minor details like how to clean up the mess this process makes of your glassware? I hope my procedure for clean up helps.
How about a synthesis route? You get none in germany, because of health limitations. Also, Acetone is a watched Chemical (Anti terror laws -_-), often hard to get, so Chloroform is neither cost effective or prepareable in useable Quantities.
More and more I'm beginning to think that living in the land of extremely free tinkering may not be the best choice in the long run. Too much rage, too much ignorance, too much power.. ..my home shop/lab is not an island.
Seems like it's hard to get a hold of this kind of paint remover today. They all advertise _"methylene chloride free"_ now... :-( *EDIT:* Well, turns out that last year (2019) the EPA banned the use of DCM as a paint remover... that fucking sucks. Apparently there were too many dummies that didn't read the safety label and used it for extended periods in enclosed areas with no ventilation or respirators... and passed away. That sucks that people died, but the report said they found 13 deaths since the year 2000 that were likely caused by DCM paint remover... This may sound cold, but honestly, thats not many deaths at all. I would think that the replacement paint removers that are now much more flammable will result in _more_ deaths. *SOURCES* 1) www.usatoday.com/story/news/nation/2019/03/16/methylene-chloride-epa-bans-chemical-used-popular-paint-strippers/3190041002/ 2) msutoday.msu.edu/news/2012/msu-investigation-links-deaths-to-paint-stripping-chemical/
If you're looking for dcm paint stripper go to a smaller hardware store that doesn't see a lot of buisness, I just went to my local one and found a jackpot. Looks like they haven't sold dcm paint stripper since they banned it lol.
At the end you wind up with a mystery brown bottle with mystery liquid in it. Surely you label it. Could we elementary learners hear and see How you make and use labels. And further, how is your pantry of materials organized. Alphabetically? By size? Could be a video.
This episode needs an update considering the EPA made it so there is no DCM in retail paint strippers
Yep! But you can buy it off ebay or Amazon. I got mine off Amazon, 1L ACS grade DCM for like $40 (Carolina Chemical)
@@jhyland87 that's alot for a little bottle
@@redram5150 gotta recycle your solvents
@@jhyland87 if you buy in larger quantities it's a lot cheaper, I got a 1 gallon bottle of 99.9% research grade DCM for $70 shipped off ebay.
@@redram5150 solvents have became very expensive due to the governments heavy regulations for them. 40 for a liter of dcm seems reasonable and it isn't that small..
Doug I love the way you do your videos, so informative and you give all the reasons why you should do things safely and how to do them. Thanks for making them.
Appreciate the hell out of you going into the theory. Lots of videos explain WHAT to do, buy not WHY. Awesome video.
Ah memories. DCM was probably the first thing I distilled. Such an easy distillation.
Just to eloborate on the point Nils Rotthowe made, the carbon is sp3 hybridized in CH2Cl2 and thus tetrahedral in shape. Due to the shape of DCM and the dipole moment of the C-Cl bond it s a kinda polar molecule that just doesn't mix with water. For example, the dipole moment (mew) for DCM is 1.55 and for isopropyl alchol mew is1.66. Keep up the good work, love the videos.
DCM is polar because of its tetrahedral shape. There are no opposite sides for the Cl to be on. The angle between each of the 4 substituents is 109.5 degrees
Erwin Rommel not exactly. The two chlorines are bigger, and therefore there's a slightly wider angle between them and a slightly narrower angle between the hydrognes. But approximately the angles are somewhere in between 109° and 110°.
Just to elaborate on this point (i know the comment is 5 years old, but in case anyone new sees this).
The main reason the dcm is not miscible with water is due to the lack of ability of water to form hydrogen bonds with it. If you look at other organic molecules of a similar size then the ones that CAN mix with water are those which have a nitrogen or oxygen in the molecule - a place where the water can hydrogen bond to. For example aldehydes cannot hydrogen bond within themselves (as the oxygen is not directly bonded to a hydrogen), but water can hydrogen bond to the =O
DCM definitely shows some polarity and this can partly explain the relatively high boiling point of DCM as opposed to the first few alkanes.
I stinkin' love finding unicorn channels like this one.
You can see how much methanol was in the distillate. At 6:43 the water layer extends just to the bottom of the label "500 ml", whereas at 7:46 the water-methanol layer extends well below the label "500 ml".
That so called polymer goop might be methyl cellulose, I don't know how you could test for it or what you could do with it though.
What's with the 1,3 benzodioxole in the last scene? I can't help wondering how nice it would look with n-methyl-propan-2-amine attached in the 5 position...
Exactly what I thought
Was wondering that myself as well... or maybe attaching an indane ring with a secondary amine. I also wonder if you could change the (secondary?) amine to a (tertiary?) amine and hang a L-lysine off the nitrogen in the indane ring to create a slow release version.
Interesting, thanks!
I was looking for this comment 😂😂 I'm not alone
Methyl celulose can be used to make metaloxide nano/micro particle paste to make electrodes from particles in dye sensitized solar cell experiments. I believe that there are many other similar uses.
💜💜💜, please come back. We need you bro.
Dichloromethane is not hugely soluble in water, but it is somewhat polar (moreso than diethyl ether) and it will dissolve to the tune of a few tens of grams per liter of water (or vice versa for water in DCM), depending on the temperature. I understand that the intent of this video was to show an easy way to acquire a useful solvent (and it did a good job of that) but the simplification might have been excessive.
You can and should re-distill the waste once enough has accumulated, effectively decreases the waste volume and increases the yield.
great video unfortunately DCM has been removed from paint strippers in the USA in 2019
laballey has DCM.
I love how fast you talk. Thats pleasant
You can pour methanol/ethanol/isopropynol into the stripper after it's mostly distilled to continue the distillation for a slightly increased yield, however there still needs to be some leftover DCM for the polymer to not crash out.
The whiteboard, that three,four methylenedioxy skeleton with a cho tacked on is the precursor to a very substantially valuable, truly mind opening substance that is worth taking. And synthesizing it then becomes why you begin learning organic. Come to find life is deep and science is what its about!
I worked with it to clean wavesoldered PCBs and we sent the dirty stuff back for re-cleaning.
I really miss Doug’s lab
I love your videos and it's always great to see what kind of chemicals you can actually get OTC. But your representation of the CH2Cl2 structure is a bit off. The way you told it, the carbon would be square planar but since it's sp3 DCM has a tetrahedral structure so there isn't really something like "on opposite sides".
Keep the expensive videos coming so my patreon account comes to good use ;)
+Nils Rotthowe It's easy to tell people with real chemistry knowledge apart isn't it. Some of the things I see people say on the internet make me have a good giggle:)
Actually, I did that on purpose to simplify the explanation. I didn't want to have to spend time explaining 3D structural representations since most people watching this video are just trying to get DCM.
+Doug's Lab OK you're probably right.
+Nils Rotthowe + Dr. Heisenberg
I do feel badly that this might teach someone incorrect information. The thought process was that most people who are looking to isolate DCM from OTC products are not chemists - they're modelmakers, auto enthusiasts, painters, etc. and in the past I have received negative feedback about long, boring explanations. I resolved to simplify explanations on the simple videos, and maintain the full explanation on the complicated syntheses that only chemists would really be interested in. Unfortunately, I then get critiqued the other way, with the chemists telling me the explanation is too simple/technically incorrect. I'm trying to find a balance where I can give enough information inspire the curious to seek more information, while still keeping things short enough to appease those who are not chemists. It's difficult!
I highly suspect you are Nile Red. Initials, Nil and rott meaning red in German. OMG
Thank you so much sir! This video is a lot of help for my research methodology!
two vids in two days! :O quickly becoming my fav chem channel
your cool people bro, advice i learned: keep it simple, and dont make ridiculious choice unless fun is involved
Good science Doug. Love the channel. I didn't have any potassium carbonate so I distilled. Also I took the initial distillation a little further, got "the goop" out. Then I evaporated the remaining solvent out of said goop. I'm 99% certain that what's left is nearly pure polysilicon. This stuff is a great additive to lubricants and is very chemical resistant. It's primarily made by Dow Corning in Michigan. Play around with it and see what you think, I'm definitely greasing up my saucer sled with the stuff this winter... I mean it's REAALLLY SLICK.
I would love to live near "the hardware store" in your town.
Ik its a joke but between ace home depot/lowes and once in a blue moon tractor supply ive been able to find everything he gets at the hardware store it just takes alot of lable reading
Auto part store also good place to label read...
its suprising what chemicals you can find isn common products
+Doug's Lab you should have used a larger sep funnel because it was too full giving the DCM smaller surface area making the washing steps less effective
I love the spoiler on the whiteboard at the end!
"the chlorines are on opposite sides" ???? It's a tetrahedron my dudes
This was my first thought lol
I guess u need to study some chemistry dude... due to the high electron withdrawing nature(electronegetivity), the bond angles get changed and it doesnt remain tetrahedral..it changes to kind of a see-saw shape
@@venkatsharma05it absolutely remains tetrahedral, it’s just not as close to ideal as methane. Methane bond angles are 109.5 degrees, DCM cl-c-cl bond angle is 112.2 degrees, less than 3 degrees from an ideal tetrahedron and almost 70 degrees from the 180 degrees characteristic of a see-saw.
Okay this has been confusing me for awhile now.
The central carbon is sp3 hybridized yes? Meaning it forms a tetrahedral shape with its bonds.
This would mean that there is no "opposite side" for the chlorines to bond to seeing as all of the bond angles are identical.
Now I am aware that steric interactions are going to cause the chlorines to repel each other, but is this really strong enough to consider the two adjacent bonds as being "opposite"?
This maybe just a slip of the tongue on your part (if you're Doug currently reading this), but as a student I just want to clarify for my own understanding.
-Thanks
sorry, this has been answered like three times already, nevermind.
Wouldnt the potassium carbonate not remove all the water if it was clumping together like that?
Late to this video but that is a really cool pressure relief on the top of sep funnel, never seen that before
A method to make DCM rather than extract it would be nice as DCM now is banned in all things in the hardware store.
how are you responsibly disposing of your chlorinated waste? or perhaps heavy metal waste?
This won't work with Methylenchloride or Chloroform. They are pretty inert in a chemical way.
Take it to a local school or fire department
Take to household hazardous waste facility
I'd like to see a synthesis of dibromomethane or diiodomethane by the Finkelstein reaction.
Wouldn't plaster of Paris (calcium sulfate anahydrous) remove the water better?
Sadly, dcm is no longer used in the US paint stripper market. Dangit
We need a video where he synthesizes DCM.
@@mikeg4972 agree, but the synthesis of DCM is not easy and not attainable by the amateur. It requires chlorine gas, methane and temperatures sbove 500c.
@@K0ester I plan to try a small scale "Free radical halogenation" using a quartz tube and a UV lamp that emits UVC.
If I succeed, I may post it here.
@@mikeg4972 very cool. Sounds interesting and just so crazy it might work!
how pure would this be? how far from pure would it be for use in extracting cinnamaldehyde via distillation and then used as a fragrance (i.e. comes in contact with skin or inhalation)
after watching this, i went and researched how DCM is made and it went as far as learning how to concentrate CO2 from atmo using potassium hydroxide and calcium hydroxide, then turning the captured CO2 into methane using the Bosch reaction, and then chlorinating the methane into DCM at 400 C. fun stuff. side product is HCl which is useful
+skyhawk551 i plan on making my own liquid salt reactor to make sodium metal and chlorine gas so i will do this for sure. besides i don't want to waste chlorine gas and there's only so much HCl i can make.
+skyhawk551 That's pretty dangerous, have you thought about the hydroxide route?
+TheTechnic Lord I have but I don't get chlorine gas from it, and I wanted to get sodium as cheap as I can and water softening pellets is the cheapest source I could find. besides I plan on getting into metallurgy so I won't be bothered by high temp. :) I will have a proper lab before getting started
skyhawk551 Ahh, getting into metallurgy too I see. I too wish I could, but unfortunately my lab consists of a kitchen, a broken beaker and a few flasks :P. I did melt salt and aluminium though, so I guess that's something. Any way I can help (I know the theory :P)?
+TheTechnic Lord I'm going to make an electric furnace that uses tungsten wire to heat it so I can go to 4000°F using zircon crucibles/linings. I would like to make my own graphite but that requires plasma arc heating to pull off
Like Cody, only Doug.
could you carefully add an alkali metal and make alkali methoxide? would this be a way to get the methanol out, and clean up the azetrope?
In the beginning when you said you wouldn't need the thermometer because it wouldn't tell you anything: wouldn't it be handy to know what temp. the vapors are at so you know what's distilling over? I know methanol has a much higher boiling point than DCM, so why wouldn't that be a good thing to know?
John Van Vynck not much, there's a difference of 15-20 degrees.
hang on, are you saying that the carbon in dcm is not tetrahedric?
Would you not want to dry/distill the methanol for use as a solvent or is that not a good idea since it has been in contact with dichloromethane?
Why do the methanol separation in the sep funnel? Seems tedious. Why not do it in a large Erlenmyer w/ a stir bar and copious water, with the sep-funnel only for separating the layers?
07:28 Where does this pressure come from?
Evaporating dcm
Low BP and all that
Why not dry with some magnesium sulfate? Is there some unique property with potassium carbonate?
Mr. Chang they both work as drying agents. Could use cacl2 as well
Mr. Chang the carbonate is just cheaper.
Outside of heating, is there any way to turn dichloromethane into something less toxic or neutralize it to be less of a hazardous material? There is some MC/HF acid-based paint stripper leftover from a tenant and I was curious about either putting small amounts onto a tray on a hot day or reacting it with something "neutralize" it. Thanks for the video!
It's still heating it, but toss cup fulls of it at a time into a big roaring fire, the elevated temperatures will allow it to burn which will destroy the molecules. Or take it to a hazardous waste drop off site, there's always that. DCM won't burn on it's own (it burns, but it's not a self-sustaining reaction since the flame temperature is lower than it's ignition temperature) but a big roaring fire with hot coals will safely break it down just fine. Adding chemicals to neutralize it will probably wind up with a more toxic chemical soup than you started with...
@@TheExplosiveGuyBurning chloroalcanes is in general a big no. You could make some extremely deadly phosgene in this way. Now, as it is dichloromethane and not chloroform you'll mostly end up with formyl monochloride instead (which decomposes rapidly to hydrochloric acid and carbon monoxide), but I still wouldn't take the risk. Slowly evaporating the stuff is the best way on a small scale. Strongly alkaline water solution will slowly decompose the stuff in a few months and is suitable too.
Hi Doug. We have purchased pure Dichloromethane for a solution of paint stripping, we will try to keep it enclosed to stop evaporation as it will do it simply on a hot day. Is there any other solution we should mix with the DCM to make it a better product for our shop, we will strip parts by immersion, not by spraying in the open air.
Thanks
You are missing things like once you didn't suply nitrogen during distillation and always use molecular sieves to store DCM longer.. P2O5 already absorbs water so no need to do separation further via funnel.
amigo como esta soy de Venezuela yo quisiera elaborar en el laboratorio el producto Diclorometano qué productos se debe utilizar y en que proporción.
A question. is it possible to rebuild the cap of the can and use the entire can as a disposable boiling vessel to get as much yield without a messy cleanup? or is there a good reason like possible contamination that can occur?
Late reply, but yes you can, the distillation temperature is so low you won't need to worry about any side reactions with the metal can or it's plastic fittings (unless it's all steel). It's really not a bad idea honestly, you'll save a number of steps and can just cap the remnants in the original can for disposal.
@@TheExplosiveGuy I use that method to isolate & purify most of my solvents.
Coleman's camp fuel (et al), yields Hexanes, & the metal spout, will accept the male 24/40 after multiple wraps of Teflon plumbers tape and pressing into the opening. The Hexanes have BPs from 40^C up to to 105^C. The bulk is about 60^C. I use a vigreaux to separate the various cuts on the first pass.
You do nice work. I like the Handle. I am a former licensed fireworks supervisor. I "get it".
@@Don_Soucy It's a good method, why waste time and dirty up glassware when it comes in It's own boiling flask lol.
And thanks, I appreciate the compliments, I haven't put as much time into my channel as I'd like to but eventually plan to do a lot more, and I'm definitely getting back to the pyro roots that my channel was originally based on (I made the channel in like 07 I think, back when I was making a lot of primaries as a hobby😉), though HPR rocket building is starting to overshadow everything else now haha, I just built my first APCP level 2 HPR rocket a few weeks ago including motor and fuel and now all I can think about is getting my class 3 lol.
Love the shorter intro haha. Great vids as usual :)
what is the condensing media used to cool the vapours and temperature of the medium
Any advice on what to clean the BF with if one waited too long to remove the residue whilst hot and still somewhat fluidy? NaOH solution work okay? Ive done this before it works quite well, so thank you Doug (i love all of your work brother, please keep it up👍🏻👍🏻) , but last time i was smart enough to remove the residue rather quickly. But say one waited too long and the residue lost its fluidity and began to cake on the flask?
Can DCM be used as a refrigerant?
I've heard that paint strippers with dichloromethane are banned in the EU and could be banned in California
How cold was the condenser
you can use solid sodium hipocloride to make the reaction?
any reason for dont use cacl2? nice lab n.n
Making methylenedioxy benzene i see? I would LOVE to see a video on piperonal.
If you add a layer of water to the DCM would it prevent it from evaporating?
hi
can you please make a video of the vacuum distillation of essential oils? thanks
Hello Doug,
I was wondering if Dichloromethane reacts with Nickle? i am bonding some plastic with Dichloromethane and plating after.
Any idea what polymer is in the polymeric goop? Maybe a polystyrenic type, maybe some byproduct of styrene production. On a similar note: PVC glue is a good source of THF, it is thickened by PCV dissolved in the THF.
+Jk Smith how can THF be sourced from PVC pipe solvent?
+GEZZA1 Distillation as with DCM. Take care - pure THF forms peroxides that can ruin your whole day. Since the polymer is PVC you might ruin a flask too.
+Jk Smith -- It's almost certainly methyl cellulose, a methyl ether of cellulose. It's also used as wallpaper paste.
See: en.wikipedia.org/wiki/Methyl_cellulose
X: So what did you do last night?
Doug: Ah, usual stuff, a nice round with a stripper…
Did you get that separatory funnel from Aliexpress?
is it hazardous?if we mix in water then drink the water is it poisonous?thanks
Yeah that'd be pretty stupid
Paint stripper with DCM contents above 0,1% is illegal in my country😓
How did you clean up the polymer?
Nice vid!
If you're in the US in 2020 looking for DCM in the hardware store, you're going to have a hard time finding it - the EPA just banned DCM in commercial products.
thats why mom and pop shops and scratch and dent shops are great, still able to get it
can you use any carbonate salt? Thanks!
The point is it's a insoluble dessicant
these videos are priceless!
It's getting a lot harder to find paint stripper with DCM, at least in Michigan.
Is it possible to make DCM in the lab?
Thanks for the tip.
I hate to be a wet blanket but you can buy laboratory grade methylene chloride or dichloromethane from Carolina chemical supplier for about $11 for 500 ml. Last I checked that can of klean strip you used was about $25 at Lowe's
You stated you wanted to have this on hand because it's a very convenient solvent to have on hand for many reactions so it seems a little bit of a waste to perform this reaction. I could see doing it if you had maybe a half a can leftover because it does not store well to just have the solvent on hand it's much cheaper to buy it from a company like sigma or Carolina
Have you tried ordering it from sigma or Carolina chemical? Good luck getting it without working for a large lab or company. This video was made for people who can't order chems from those companies.
I love your work Doug, please keep it up 👍🏻👍🏻 Any advice on what to clean a BF with, if one waited too long to remove the residuals and they began to dry and cake the walls of the flask?
On adderall?
How did you manage to get all the goop out of your flask? I can get most of it out in mine, but there is still residue left.
+Creativity I used hot water and a cleaning brush. I don't know if it helped but i also used a little acetone.
If all else fails... piranha solution.... just be careful w/ it
Just hook the rubbery residue with a bent bit of wire and drag it out through the neck of the flask, then clean flask with a brush and a bit of acetone.
The flooring business uses DCM mix to clean carpet glue off tools and the edges of the carpet. I'm fairly sure the most common product I used had the polymeric goop and DCM w/o methanol. Just another source if any other floor-installers/amateur chemists have some laying around. I forget the number commonly assigned to the compound. - TVC
Would sodium hydroxide work instead of potassium carbonate
I don't think so but I'm not sure. Usually, NaOH is already a little wet. You can use Epson salt previously dried in the oven.
Thanks for your very informative videos. I really enjoyed watching them! I am just curious, are you working without a mask and a fumehood? As it was a moment when you hold a flask with methanol+dichloromethane, flask was open. So you could simply breath vapors which are toxic, expecially from methanol?
There is a big extraction fan behind the lab bench
Nope, that's the inside of his fume hood.
Hey could someone please tell me how/if you can separate petroleum and methylene chloride, there’s a local paint striper here that contains methylene chloride but also petrol and I Seen they have similar boiling points
Is there a solution that one or the other is soluble in but not the other
Lol i had no idea about the recent ban of DCM in consumer (but not commerical) by the EPA until i needed some DCM and found no products containing it or advertising it as NMP or methylene chloride free. I went to a few hardware stores to check and even the brand that I used to use, changed it's formula... Even Klean Strip changed theirs...
i thought the price of paint stripper would be more than purchasing pure DCM? Or is it hard to buy pure DCM?
GEZZA1 its not the case we want the science behind distillation i can directly buy it .
Are you going to to methylate, catechol? I noticed it at the end of the video.
+Joey Petrovyk
Please do a vid on making benzodioxole!
+MrIhavnovideos that does not look like o-dinitrobenzene, can't see it very well but the benzene ring has a 1,2 oxygen bond and o-dinitrobenzene would have NO2 on 1 and 2. But the bottom structure clearly is 1,3-benzodioxole
+MrIhavnovideos Thanks, I can see how it led you to think it was dinitro, no worries. Have you tried synthesising 1,3-benzodioxole?
+MrIhavnovideos for a video on piperine check out +chemplayer s page. He has other awesome videos
DCM is gone from all shelves as of 1/1/2020. Very unfortunate this video is now obsolete as I literally just planned on isolating some. Better stock up on most types of store bought solvents. MEK is another along with Xylene for that matter that are gone now too :(
Some countries still sell products that contain dichloromethane, but this is not much consolation for those in countries that do not.
Doug, I have a rather beginner question that I hope you will answer.
If one were to have a 2L sized heating mantle with magnetic stirring option, would I be able to also use smaller boiling flasks ( 1L, 500ml 250ml) in the 2L sized mantle???
I see so many different kinds of mantles in different sizes, I was hoping to not have to buy more than 1. or perhaps would having a big hot plate with stirrer be better, in conjunction with an oil bath?
Please let me know when convenient, thank you for your excellent videos, I’ve learned so much!
-alex
This may be two years late, but yeah you can use smaller flasks in bigger mantles if you need to, it's always an option. Obviously you won't be able to match the heat transference to the bottom of the flask due to less contact area but it really doesn't matter, since a 2 liter mantle can put out some serious juice, it will heat perfectly fine. I get by with just a 1 liter mantle and a Corning PC-351 600W hot plate, if the mantle won't fit my vessel then an oil bath on the hot plate will. I do think it would be pretty nice to have the full range of mantles though, perhaps one day when my hobbies and budget align lol.
haha better late than never!
thx for the reply though bro, just saw it as I’m not on here as much
I appreciate the feedback, I’m a super noob on a budget, so I’m glad to hear a 2L mantle will work just fine for smaller flasks
Thx again for the help man!👍🏼
@@alexandergonzales5121 Good philosophy! Lol I'm glad to help, especially for a fellow budget-minded amateur chemist!
How do you get the dichloromethane with the two Cl on one side? I mean you have described the 1,3 dichloromethane which is non-polar, but I would love to have the 1,2 dichloromethane which is polar🤔
Cool experiment, but I just bought a gallon of lab grade. I use it to solvent weld 3-d print components.
The left over polymer crap in the boiling flask is problematic in its removal. I read someplace or saw something that said that kerosene will remove it. When I used kerosene to try and remove it , it did not work. I used some tetrachloromethane (aka Brakekleen) in its can and that sorta worked but still didn't break it down very well. I finally used some very hot water and Dawn dish soap which helped but I still had specs of that shit stuck to the sides of the flask. I got it out finally by mixing up about two tablespoons of sodium hydroxide in cold water, and let it set for a couple of hours. Btw, HCL never phased it either.
I also used Kleanstrip paint stripper. My can of it was almost straight DCM and no methanol. I washed it with water and couldn't extract any methanol from the wash water. Not to say it didn't contain any, just that the percentage in it was very low. This is a great video, I'm just relating my experience with this process. The problems with videos like these is that the makers of them leave out some minor details like how to clean up the mess this process makes of your glassware? I hope my procedure for clean up helps.
there's no carbon tetrachloride in brake cleaner
that last reaction looks interesting... 👀
Shame you can’t get DCM paint thinner anymore these days
Hey, anyone please can put legends on this video? I m Brazillian and I still need CC :/
How about a synthesis route? You get none in germany, because of health limitations. Also, Acetone is a watched Chemical (Anti terror laws -_-), often hard to get, so Chloroform is neither cost effective or prepareable in useable Quantities.
*****
Sometimes I'd like to do so, but leaving every friend or so is nothing for me...
More and more I'm beginning to think that living in the land of extremely free tinkering may not be the best choice in the long run. Too much rage, too much ignorance, too much power.. ..my home shop/lab is not an island.
I can buy acetone easily, but no kind of acid.
I thought for a sec that i had the vid settings set to speed up the video... But it turns out that you just talk really fast, lol
so cool
Seems like it's hard to get a hold of this kind of paint remover today. They all advertise _"methylene chloride free"_ now... :-(
*EDIT:* Well, turns out that last year (2019) the EPA banned the use of DCM as a paint remover... that fucking sucks. Apparently there were too many dummies that didn't read the safety label and used it for extended periods in enclosed areas with no ventilation or respirators... and passed away. That sucks that people died, but the report said they found 13 deaths since the year 2000 that were likely caused by DCM paint remover... This may sound cold, but honestly, thats not many deaths at all. I would think that the replacement paint removers that are now much more flammable will result in _more_ deaths.
*SOURCES*
1) www.usatoday.com/story/news/nation/2019/03/16/methylene-chloride-epa-bans-chemical-used-popular-paint-strippers/3190041002/
2) msutoday.msu.edu/news/2012/msu-investigation-links-deaths-to-paint-stripping-chemical/
If you're looking for dcm paint stripper go to a smaller hardware store that doesn't see a lot of buisness, I just went to my local one and found a jackpot. Looks like they haven't sold dcm paint stripper since they banned it lol.
or buy some pure dcm off amazon :)
@@iocus_54roudachevski3 That's where I got my DCM, Amazon :-) It's usually reasonably priced.
At the end you wind up with a mystery brown bottle with mystery liquid in it. Surely you label it. Could we elementary learners hear and see How you make and use labels. And further, how is your pantry of materials organized. Alphabetically? By size? Could be a video.
well done son
finally a video on how to make DCM!!
here in poland you can buy 500ml of DCM for 4 euros
Nasty shit. I use it at work.
great teacher