Dimethyl Oxalate

In this video, I make dimethyl oxalate from oxalic acid and methanol.
Patreon Link: / dougslab
Twitter: @YTDougsLab
Google+: plus.google.co...

[@ScienceWithJames]

Here's an update from Doug that he posted on the Science Madness forum: He moved into a new house and is currently busy with that. He is working on settling in, finding time to do chemistry, and setting up a new lab. He probably won't be back soon, but when he is, expect a new lab setup!

[@karolus28]

cool

[@All_Science]

@@karolus28 very cool

[@karolus28]

@@All_Science quite indeed

[@gabrielbr1459]

Thanks for clarifying

[@dudetapedtoafridge3073]

OMG YES JAMES HOLY F##K YES

[@duyataksis5210]

Aaaaaaaaaaaand he's gone. Bye, Doug! See you again next year!

[@jasonvoorhes3429]

I need him!!!!

[@mikebarnacle1469]

Happy spiders though

[@thetilenglishtaste9913]

*in 2 years

[@n-n.n3248]

@D. R. yeah YT rules are awful If this keep going like this , every cool chem channel will be banned and only will stand the shitty ones(make slime/playDoh as the "coolest" science projects) :c

[@pd1jdw630]

It’s now 2 years later.

[@DarkMetaOFFICIAL]

Does he even realize how big his channel has become now?! This is a money maker just sitting here. Man

[@b-rad3937]

I don't think he does or he doesn't care

[@NurdRage]

If you're going to make trichlorophenol please be careful and thoroughly research the formation of side products like TCDD. I wanted to make TCP awhile back but i decided against it due to TCDD formation.

[@mozarellaman1201]

hadn't even heard of the compound, looks like scary stuff

[@AlChemicalLife]

Agent Orange :( , be careful Doug !

[@NatasPvPMontagesz]

He didnt post anything in a month, did he died?

[@bigboineptune9567]

This is scary given the fact that he hasn't posted in 7 months.

[@jeffreyfugh7602]

If a chemical's evilness is enough to deter a hardened badass chemist like NurdRage, it IS really not a good idea to take such a risk.

[@DavidJohnson-ty8qz]

Doug. Please come back!!!!! We miss seeing your content.

[@BlackWolf42-]

I know the family and other commitments take precedence over playing in the lab and doing KZbin videos. I wish you the best. You are/were the best educational producer in the field of KZbin chemistry; you can run with the best of them.

[@brandonross6083]

It's sad he disappeared like that though. He had a talent with this. Probably the best chem tuber out of them all and he wasn't even around long enough to reap any benefit from it. His videos have more potential than any chemistry videos I've ever seen on KZbin

[@RedwoodRhiadra]

Doug, I really hope you're all right.

[@jhyland87]

Same..

[@unclecrusty1991]

I hope you come back soon Doug. Your videos give me confidence to perform projects myself because of the education you give while talking about some of these chemicals. It'd be like Christmas to see you uploading again. Hope to see you soon.

[@CollegeChemistry]

Doug the videos just keep rolling out from you, and I'm loving it.

[@Spycyzygy]

This comment aged poorly rip

[@OkieDokieSmokie]

@@Spycyzygy very poorly...

[@miabobeea2644]

F

[@cockatieltime2259]

Rip doug :(

[@GrimStarr]

@@Spycyzygy hahaha

[@liamcg2521]

really miss this channel posting, one of the best.

[@atomicreactions9201]

Since you quit upoading videos I feel like a forgotten lab spatula in an acid solution.

[@hopeforescape884]

I just wanted to thank you for being an inspiration to me, I am three weeks away from graduating with a bachelor's in chemistry, and I will be starting grad school this August, I started watching you all the way back in middle school, it sad you have not continued to upload, but none the less thanks for your videos!

[@caltto1361]

Doug come backkkkkk we need our Chemistry king backkkkk

[@normellow]

Let’s go Doug ! Chemistry doesn’t wait for nobody !

[@lastplace199]

Is doug dead or taking another year long hiatus? Find out next year on Dragon Ball Z.

[@AtlasReburdened]

And then the f*%&ing series just restarts.

[@shinyblu2144]

as i saw this comment i was playing dbz2

[@MobscastBlackOut]

He's dead rip

[@Adventist1997]

@@MobscastBlackOut Is he actually???

[@jhyland87]

@@Adventist1997 i think hes just joking.

[@svoranger]

@Doug's lab, When work slows down and family life allows, hope to see some new videos from you. And I think your channel is every bit as good as Nile Red and Nerd Rage.

[@ph08nyx]

Now we will never know what this super secret and super cool reaction is! I feel miserable!

[@AtlasReburdened]

We still miss you, Doug. Hope you're doing alright in this busy world.

[@michaeldomansky8497]

Where were all these great "teachers" when I was in school! Doug, come back!

[@erictorkelson5778]

Definitely too much H2SO4. I copied your prep this week also running it on the 1 m scale but reducing the sulfuric acid to 25ml. No issues drying it on the pump and it proceeded at essentially the same speed. Followed up with a re-xtal in hot MeOH to clean off lingering sulfuric.

[@moritzschaferalthaus3461]

Hi Doug In your last Lab Tour for 2500 subscribers you said you will make a more detailed Lab Tour in the future.Can we see that in one of your next videos? I love your channel and im so happy that you‘re back.

[@grantstech.]

I’ve been waiting so patiently all day. So relieved that you actually uploaded. As always love the video!

[@senorjp21]

Hey Doug. Thanks for all these videos. They are excellent. I wish you would make more, but you do you. Cheers

[@drkaranmannan]

Please don't stop uploading. Your Channel is bound to grow. Collab with codys lab maybe?

[@zock4419]

I think your videos are great and it's pretty awesome to be able to expect the release date of the new videos!

[@mrjcaudy]

Doug where are you?

[@vojtechpesl4471]

Doug, please come back !

[@praspurgh]

I remember watching your videos like about 10 years ago, and this video pops up on my home page. still same voice and lab lol

[@Josezwitterion]

I miss you DOUG

[@spinjector]

Hi Doug. I'm a fan of your videos and watch them regularly. I have some suggestions to improve the sound quality of your audio. I'm not sure what you record with, if it's a video camera or cell phone. If it's a cell phone, the solution is easier, see if you can use a bluetooth headset with noise cancellation. First, it will get the microphone closer to your mouth so the sound of your voice is louder in comparison with the noise in the background. If you're using a video camera with a microphone input, get one of those over the ear microphones like you see rock stars using and plug it into the microphone input. Either solution should be able to be had for an economical price. Ebay and Amazon are overflowing with bluetooth microphones, and the over-ear performance microphones can be had at any music store. Whichever one it is, be sure to look for the terms noise-cancelling, directional, or if it's a performance microphone, look for the term cardioid pattern. Barring technological improvements, there are three main sources of noise in your videos: the aspirator, the vent fan, and OMG THAT SQUEAKY LAB JACK lol. Please, for the love of everything and anything to do with my eardrums, please put some grease on that lab jack lol. If you're concerned about volatile hydrocarbons that may interact with any of your experiments, I understand, but perhaps you could just use a dab of that heavily fluorinated grease that you use to grease your glass joints. Should be no reaction problems there, eh? The vent fan would require a little more engineering, and might be more difficult to replace. But with fans, slower and bigger is quieter. Perhaps one of those big white plastic house fans that people get for the summertime? Also with a larger fan, the frequency of the noise it generates would be lower, and less likely to pierce through to the microphone and the recording. And lastly, the remaining screaming roar in your videos is the aspirator. The solution to there is simple, just get a piece of hose about 12 to 18 in long and jam it on the outlet. Make it just long enough so that you can lay the end down in the sink, or put it right down in the drain. Or possibly just in a container sitting on the bottom of the sink to catch the water, after which it can gently overflow and then go down the drain. Peace out bro, keep up the good work.

[@hubrisnaut]

Hey Doug, Your videos are awesome. Any chance you will make more? Hope you are well.

[@MrCrazyChemist]

Loving the new content, I think that if you put a piece of hose on the bottom of your aspirator it would be a lot quieter. Mine sure is

[@mwilson14]

I'll be watching this one later. I experimented quite a bit with oxalate compounds for a couple months and have been hoarding Oxalic acid since Bartell's was selling it buy one get one free.

[@DougsLab]

I want to see what you come up with!

[@mwilson14]

Good deal and I'll be making videos again soon which will be better quality than my previous number of low quality posts. I have a fair amount of ferrous oxalate and even more potassium ferrioxalate, the latter of which I need to use soon since K3Fe(C2O4)3 is very light sensitive and will decompose and become useless. I was thinking about making calcium oxalate to simulate kidney stones. LOL. I have a microscope with a mounted camera that I'd like to upgrade so I can take non-choppy video and make that into a theme for my channel. I don't see tons of people doing micrograph photo/video stuff and I'd like to see others doing a lot more of that. I usually use my camera on my phone out of convenience of not having to hook the microscope up to my laptop, plus I can get a better picture since my phone has a higher resolution. I updated my google header photo with phosphate stabilizers I isolated from a Pepto Bismal bismuth extraction and lit it with UV light under my microscope. It's a pretty cool photo if you want to check it out.

[@mwilson14]

I just found out something that made me jump up with excitement as I've been working on crystallizing neodymium sulfate for a couple of months! I have a small bit of crystals but haven't grown since they formed weeks ago. They are a beautiful lavender color. Most everything else I have created so far is clear, white, yellow, green, blue and dirty orange in color. I do have my nearly black copper acetate crystals, which I've been very fond of, but nothing yet beats the neodymium sulfate crystals. There is a topic I found on the Sciencemadness forums and it involves extracting the Nd from solution by precipitating it out via an oxalate. I've not found too much info on Nd, but I guess I wasn't searching incredibly hard either. I didn't realize that Nd is less soluble in near boiling water than it is in cold!

[@mwilson14]

I posted a short video on my channel of the results from my neodymium extraction experiment using oxalic acid. I'll be making a how-to video on the subject in the future. kzbin.info/www/bejne/roDGXnuordeVnJo

[@RushilFernandes]

Thanks for posting. It's always fun to watch organic synthesis videos. I would like to ask, however, why you don't use TLC to monitor the progress of your reactions. It would make things so much easier IMHO. I spent my PhD constantly doing column chromatography and TLC and for some reason I haven't seen a single KZbin chemistry person do either.

[@RobsMiscellania]

I was similarly dissatisfied with the lack of chromatography on KZbin as well, so I decided to equip myself and I will shortly be producing videos for my channel. I will be presenting organic synthesis with applications to medicinal chemistry and will be prominently featuring the use of TLC and column/flash chromatography. Since I plan on making series of videos of multistep syntheses, it will sometimes be required for me to purify a compound I have synthesized in order for the next step of the synthesis to take place successfully. I will also be using melting point, refractive index, and colorimetry where applicable in order to more fully characterize these sets of compounds. I hope you'll join me for some exciting chemistry! I plan to begin with an example of the Sandmeyer reaction shortly after the beginning of the new year.

[@user-ns7ng6xm3p]

پس چیشد محتوای ویدئو شیمی که گفتی ​@@RobsMiscellania

[@samwheller]

Hope all is good. Feel like, given the era, fate might have given us Doug's Lab > Cody's Lab had things continued.

[@ScienceWithJames]

Great video, as always, Doug.

[@feIps_]

Not again Doug. I have a heart, you know?

[@Christopher.Marshall]

Doug, in another video not too long before this one you said you were going to produce videos more frequently but you haven't followed through. When can we expect to see more of your chemistry?

[@LockeSoriku]

Great video. Seems as though I arrived after the end. Hopefully, he returns.

[@mihneasimionescu2022]

It has been two years... what happened to Doug? He was my favorite teacher...

[@tmd9412]

He got married and moved to somewhere without internet

[@Correct_Opinion]

We miss you :(

[@drkaranmannan]

10:21, Doug, you're an artist. ( you'll probably catch the reference...)

[@cvabds]

I love your vídeos, i need them, NileRed does pretty good explanation and video editing, hope you get your patreons UP, you should do some promotion of your channel somewhere.

[@buttmeister]

I did enjoy it and your videos are very educational so i became a patreon thanks

[@repomandan07]

Love that opening for your patreon supporters.

[@pyromen321]

Hey Doug, mind if I ask what you do for a living? I'm unsure if you work in a chemistry-related field or if chemistry is simply one of your hobbies

[@seanm3644]

I'm also curious about this

[@DougsLab]

I work in the automobile airbag industry, which has a lot to do with mechanical engineering but also the chemistry of explosives and propellants, which is my major field of study.

[@oliverrapp93]

Doug's Lab heyyyy make some azides

[@thenewbgamer6416]

He answered this. He is alive... [Things intensify]

[@brandonhemphill6816]

@@thenewbgamer6416 yeah 4 years ago

[@bearcatben4762]

I can't believe its been more than a year now

[@miabobeea2644]

"as I'll be showing in some upcoming videos" gdi Doug

[@miabobeea2644]

I hope he's okay...

[@andrewandrei3062]

@@miabobeea2644 I hope that too

[@jpdemer5]

Melting the product is a poor way to get rid of water, and of course it's not effective at all for removal of sulfuric acid. Water can remain dissolved in the liquid ester, where it has negligible vapor pressure, whereas there is no place for it in the crystalline material, from which it will readily evaporate. You will get much better results drying crystalline material in the dessicator. I'd add cold water to the reaction mixture, stir for a minute, then filter, to minimize the amount lost as a methanol solution. Dissolve again in fresh methanol, add cold water, and repeat. That should get most of the acid out.

[@System32F]

when washing the end product you need to clean the crystals really good you did not mixed the water with the impacted lumps of product, you should turn off the vacuum and thoroughly mix then turn the vacuum on and if purity is essential you should do it again

[@hobbyhyper]

I think Doug ate his dimethyl oxalate...

[@hongbitter7142]

More videos Doug! We need more

[@cognitivedissonancer]

Doug's mysterious disappearances cannot but remind me of Twin Peaks.

[@mrchangcooler]

He's going, he's going, and he's gone ladies and gentlemen. It was a good little run while it lasted.

[@zugzwang9954]

I did some snooping and found a few online profiles under his own name, with a few flickers of activity in mid-late 2018, months after this video. So good news since I'm pretty sure he isn't dead, but it's a shame he chose to disappear without any explanation like this.

[@ScienceWithJames]

Links?

[@Prchemist06]

It has been 2.5 years you made new science videos Plz sir come back and make new video😑

[@Curiosity_Cars]

hes played minecraft since this video aired.. so most like busy with family.

[@greenjames]

How do you know

[@verdatum]

I miss you, and your videos.

[@AtlasReburdened]

We miss you, Doug. I hope Chicago didn't get you.

[@arjunyg4655]

we miss you Doug!

[@GLITCH_-.-]

I like the speed you're talking at! :D Sometimes I have to speed up a video because the dude is unbearable slow. Your speed is perfect. :) One question: Can you put a hose on the faucet or would that kill the vac? I never used an aspirator, but I think that could work. On the other hand, you probably would have thought of this before me. (Sentence seems clumsy... I'm german) :P

[@DC_DC_DC_DC]

Distelzombie Centzon Totochtin maybe just a slope or slide so it doesn't hit the sink

[@GLITCH_-.-]

yea, that would work. :)

[@ElizabethGreene]

Someone should make a beaker that is slightly tapered outward so it's easier to remove products like the big cake at 7:35

[@siberianstuntman3344]

That's why we need more chemical engineers

[@陈逸民]

where are you?

[@thenewbgamer6416]

Im glad to see a 或那个 caring for Doug.

[@Spycyzygy]

Rip Doug again

[@jozefnovak7750]

Super! Thank you very much!

[@walterbunn280]

This is a good synthesis. The only thing I'd do a little differently is use hydrochloric acid instead of sulfuric acid. Hydrochloric acid won't contaminate the end product, and the methanol will be a bit more reactive than with sulfuric acid.

[@Spycyzygy]

Unless you mean bubbling in HCl gas, adding store bought HCl would add loads of water and destroy yield

[@walterbunn280]

@@Spycyzygy Actually this got me to thinking about the chemical reference I was thinking about. I wonder if the reference was actually comparing hcl (gas) to sulfuric acid (aqueous). The book lists hcl as being 3-4 times faster, but it doesn't mention state of the acid. I'll hafta dig around and look at it. The book lists hcl as being more disruptive towards hydroxide bonds, because the anion is smaller than the sulfuric acid, but the dehydrating action of the sulfuric acid could easily offset that. If they're comparing different states though, that'd account for the improved yield.

[@sugarbooty]

@@walterbunn280 Interesting thoughts indeed

[@Guido125]

> If you want to see more of these videos, please press the subscribe button. Not working D:

[@theginginator1488]

Really cool video! I thought the liquid would be way more viscous than it was

[@snowdaysrule]

Ay we have the same fritted vacuum filtration funnel! 150ml #3 medium porosity haha

[@FantomZap]

I'm sad, where'd Doug go again?

[@Cristi0986]

I miss you man.i whant video

[@dhawthorne1634]

Taking this way further than Nurdrage did. I always wished he'd shown how to do this from scratch.

[@jordanandrews6479]

Come back, Doug! This shit is mint

[@doppler3237]

where did he go?

[@alexfish3070]

"We'll talk about that in the next video".......

[@hopeforescape884]

I miss you its been 3 years... 😢

[@science_and_anonymous]

LETS SEE A VIDEO DEVOTED TO SOLVENTS!!!

[@XC2long4u]

Could you do a video on hardware? Cheap glass vs expensive glass, different brand mantles etc.

[@mistertheguy3073]

Hey, I love chemistry too!

[@keymaster2108]

Make a video on Distillation of kerosene. I know it seems basic but very little info is available about this on the web

[@zelaboratorium8753]

where are the promissed videos doug ? we miss you :,(

[@sundayjohn5619]

Pls, doug, i want to know how to prepare molybdenum oxalate and nickel oxalate. Thanks

[@geeder9086]

What is "transistorification"? Is that how transistors are made -- LOL. Thanks for another excellent video!

[@matthewcncsutton5283]

Hope to see more videos some time doug

[@SD-fw9li]

Oh heck yeah

[@ggggosebssp]

What with all that upcoming videos, I watched all of tour videos already and I want more

[@h.Freeman]

Someone got caught cooking mithemfetimeen

[@jamesg1367]

Nice. If there's residual H2SO4, is it an issue wrt your intended experiments?

[@DougsLab]

Not if I use an excess of the required catalyst, which is strongly basic! *hint*

[@jamesg1367]

I can hazard a guess. Maybe this: onlinelibrary.wiley.com/wol1/doi/10.1002/cctc.201300209/full Or maybe this: page-one.live.cf.public.springer.com/pdf/preview/10.1007/BF00910842

[@EthnobotanikFAQ]

I guess the product will glow :D ohh he already revealed it..

[@user21XXL]

N(Et)3 ?

[@TheBackyardChemist]

You might want to take care when chlorinating phenol, I read somewhere it might form small amounts of highly toxic TCDD as a side product.

[@johnblacksuperchemist2556]

GREAT VIDEO

[@iocus_54roudachevski3]

Doug pls come back

[@leonardomarinovic3492]

Are you ok?

[@b-rad3937]

When are you coming back buddy

[@guytech7310]

Looks like he moved to a rural area with only dial up internet. Thus making it impossible to upload. Last post he made was in 2019 on sciencemadness (user: Praxichys). I would guess he not coming back anytime soon :(

[@gmglabs5395]

I think I know what you have got planned for the dimethyl oxalate... I remember reading a bunch of old DuPont patents relating to it lol.

[@AntiProtonBoy]

We love chemistry, too, internet friend.

[@lilalexbmx]

And he's gone

[@drewlew18]

Please come back Doug :)

[@Guido125]

Hope you're doing ok! I miss your videos.

[@emmepombar3328]

Hey Doug, are you alright? We are missing your awesome videos.

[@tmd9412]

He got married and moved to somewhere without internet