@@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.
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!
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.
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!
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.
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.
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
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".
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
+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
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.
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.
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
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?
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?
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.
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?
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.
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?
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)
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?
Hello, my teacher, don't be tired. Is there carbon tetrachloride or chloroform in this methylene chloride that you made? Or is there only methylene chloride?
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.
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.
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...
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
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
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.
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.
@@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.
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!👍🏼
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.
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
+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
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.
God i hope you're getting every red fucking cent now. Hey, get paid brother. I've got ten seconds for you,I mean ten lousy seconds to see 2 ads that will keep you going? Fuck yeah
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.
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
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 :(
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.
DCM non-polar? Ehm, no. EDIT: Okay, so that was a lot of nonsense at the start, I have to step in here. DCM has tetrahedral geometry, therefore the molecule clearly has a dipole moment. The low solubility in water is primarily associated with the high density of chlorinated solvents.
