IBX is easily S tier, is such a clean oxidant - it + the thing you want oxidised in DMSO, stir at RT for ~ 30 mins then dilute with water, filter and extract with ether - it has helped me out of a few tight spots
Depends on the context. IBX/DMP are great for smaller scale academic/medicinal chemistry routes. For us process chemists not so much a S tier reagent :)
"Let's put it this way: during World War II, the Germans were very interested in using it in self-igniting flamethrowers, but found it too nasty to work with. It is apparently about the most vigorous fluorinating agent known, and is much more difficult to handle than fluorine gas. That’s one of those statements you don’t get to hear very often, and it should be enough to make any sensible chemist turn around smartly and head down the hall in the other direction."
When I was a lifeguard in high school, we just chlorinated our pool with a giant tank of cl2 (like the size of a liquid n2 tank), it was terrifying to change out.
why the fuck did they chlorinate the pool with chlorine gas? it's gonna be one hell of a desinfactant, but thry forgot they might desinfact you and you from the face of the earth
I've also been to a country where what I assume was a public water supply shed had a tank of chlorine gas *outside* viewable from the road, with some pipe going in. It terrified me.
It's a pretty low-brow joke and I would have thought I'd stop finding it funny, but "D for DMSO" and suchlike cracks me up a little every time. It's the deadpan delivery I think; it really complements the absurdist nature of these presentations.
my low broke joke with dmso: ever since someone introduced me into the DMSO song version of DVNO i can never listen to it normally without smiling and people are always creeped out, but explaining to them is way to hard and makes it just worse and even more funny for me.
I guess it's kinda funny to me because he talks about all this cool educated chemistry stuff with the jargon and anecdotes, and then justifies the placement with "starts with this letter" lol. I do think the bit has run its course tho
Fun fact: F is such a strong oxidizer NASA experimented with it as a rocket fuel. It was used with H and liquid Li and produced the highest specific impulse of any chemical rocket. However it was never used in practice because a failure means covering large areas, or even the launch site and accompanying engineers, in F and Li which is really bad for obvious reasons.
Anyone curious about rocket fuels is required to read Ignition! by John D Clark, 1972. Here is an excerpt from a section about fluorine: It can be contained in several of the structural metals: steel, copper, aluminum, etc. because it forms, immediately, a thin, inert coating of metal fluoride which prevents further attack. But if that inert layer is scrubbed off, or melted, the results can be spectacular. For instance, if the gas is allowed to flow rapidly out of an orifice or a valve, or if it touches a spot of grease or something like that, the metal is just as likely as not to ignite and a fluorine-aluminum fire is something to see. From a distance. [...] The development of large fluorine motors was a slow process, and sometimes a spectacular one. I saw one movie of a run made by Bell Aerosystems, during which a fluorine seal failed and the metal ignited. It looked as though the motor had two nozzles at right angles, with as much flame coming from the leak as from the nozzle. The motor was destroyed and the whole test cell burned out before the operators could shut down.
Fuming nitric acid is also a great oxidizer for rocketry, as is N2O4. ClF3 was once tried as an oxidizer, and had excellent performance, but it is of course truly evil and was not very popular. If you're interested in reading about the terrifying propellant chemistry that went on in the early days of rocketry, check out the book *Ignition!* by John D. Clark.
On the subject of rocketry, hydrogen peroxide decomposed with potassium permanganate catalyst deserves an honorable mention, not as an oxidiser but as a means of driving turbopumps for main fuel/oxidizer. Used in torpedoes, missiles, and the early days of rocketry, it's still used in the Soyuz rocket (1950s to present) to generate oxygen/steam at high pressure to drive the propellant pumps. In other words, the "elephant's toothpaste" reaction has engineering uses. Hydrogen peroxide has been used as an oxidiser in rocketry but the major use is catalytic decomposition for driving turbopumps, or as a monopropellant.
Oxone really should have been on the list! It’s high molar mass, i.e. large amounts are necessary, which is a downside but it’s very useful, non-toxic and even used in pools. Who doesn’t like pools? S-tier for me! (And it can even be purified to stay as reactive but using smaller amounts)
6:42 I'm thinking of the 2 times when a room mate in our students' dorm cleaned the mold in the shower and the whole hallway reeked of clorine gas. Not the typical pool smell, but real clorine. First I thought I was imagining things (why the heck would I smell clorine at home?) but then I checked the hallway and the shower and was greeted with a cloud. I opened all windows (they hadn't done that in the shower) and the backyard door before I furiously send some massages in our WhatsApp group. I remember how terrified they reacted, when I told them, that they produced real clorine gas. I don't know how the did it, but I guess they mixed different cleaners.
@@That_Chemist I have 2 budgies so I was quite worried that I could smell it in my room. I had to cover the slit beneath my door where the chlorine came through with a towel to protect them (at least a little).
It's easily done. Hypochlorite bleach and acid down the toilet at the same time. Hypochlorite will always have a big warning about this somewhere on the bottle.
Potassium permanganate and hydrogen peroxide solutions also make good post treatments for sealing trivalent chromium coatings. Any oxidising agent would really, but weak solutions of those mentioned agents are good. Edit: (conversion coatings on aluminium) I should’ve mentioned the substrate
Dupont at their Teflon plant outside of Parkersburg, WV uses 10% Fluorine Gas with 90% nitrogen in Small trailers. Gentlemen told me they actually wanted to use a higher ratio but anything higher than 10% caused issues. He went on to say if they had a trailer leak it would overwhelm the entire 50 acre site in 10 minutes. When they would need to unload the trailer it would be back up to an Overgrown Fume hood so they could connect the trailer in a sealed environment. This fume hood was actually located outside the building incase of a leak.
Potassium persulfate is a really convenient source of peroxysulfuric acid. I would use this sometimes as a way to clean out dirty, clogged up fritted glass filter funnels: Add some potassium persulfate to the funnel, pour some concentrated sulfuric acid in after it, and heat it up gently with an electric hot air heat gun until the persulfate crystals dissolve in the acid. Then just let the liquid dribble through the fritted glass, and on its way it will oxidize anything stuck in there. Really easy and very effective.
Should be mentioned: Concentrated perchloric acid will explode when heated. I once tried to clean a bit of expensive glassware with perchloric acid. Put the apparatus filled with the acid in a microwave. I thought I was being careful by trying 'only' 20s first. About 10s in, the whole thing exploded. An interesting oxidizer is ferrate salts. Iron really does not like being in the +6 oxidation state. It is a stronger oxidant than permanganate. A new manufacturing process has recently been developed, so it's not as expensive as it used to be. A promising industrial application is as a lethal oxidizer in water purification. Since it reduces to rust in water, a film of rust settles in the water, trapping particulates and sinking them to the bottom of the container. Since it's only iron, unlike permanganate or chlorine, it's nontoxic. A big con is that it decomposes in water, esp. acidic solutions, and it's mildly hygroscopic. Keep it dry, or keep it alkaline.
Yess!!! The DMSO is a mild oxidant but perfect when is a methionine in the reaction and you have to make a cys-cys breach in a solution also to conserve the cys in a reduced state
tier lists are so cool and fun to watch and educational, thank you. unfortunately i can not help you with ideas for tier lists since im not too deep into the subject, only introductory lab courses, hmm i believe you already did solvents right? glassware as well i believe, damn.... something in the realm of physical chemistry or inorganic chemistry? those lanthanides with relativistic effects on their electrons do sound cool tbh.... thank you for everything :)
I got to use Potassium Ferricyanide in my undergrad analytical chem class. We used it with glucose oxidase to measure glucose. No idea if it is a good oxidizer, but I used it.
FINALLY I KNOW WHAT THESE ARE NOW, I'm a FedEx driver and I deliver to a hospital every day. I'd say maybe once or twice a week I have to go through a special procedure to deliver hazardous materials to them, and most commonly it has a big "oxidizer" label on it
hey cut him some slack..... lysome was the first thing that popped into my mind... at least he didn't say it if he didn't know , right? .... I was going to look it up but you beat me to it.
Singlet oxygen is so reactive it's essentially always a short-lived intermediate, usually in photochemistry, in my experience. What is anyone doing that involves gathering up a significant amount of it all at once?
Definitely make more Toxic videos! they're great. Data fraud doesn't get nearly enough attention, even within academia. Hopefully raising awareness can help prevent it
I have several (working) antique violet ray units, basically a hand held "medical" tesla coil, and as such creates ozone during use. They had different electrodes to use depending on what part of the human body they were "treating" and it could cure all... For example, did you have breathing problems? Here's a twin nozzled adapter that allows you to breathe lovely ozone in through each nostril! Because 3 oxygen molecules are better than 2 right! 😳
Interesting and thanks. Noticed that you mention Chlorine a couple of times. There's a sort of trick that you can do with Ferric Chloride. An older one, been around since at least the 1930s. If you heat up this material to about 70 degrees C or so, you get a sort of equilibrium that goes: Ferric Chloride Ferrous Chloride. An acquires solution of this material will work nicely to etch copper printer circuit boards. You get cuprous chloride and ferric chloride. If you pour off the liquid, while still warm, you can rinse off your board. I suppose there might be an equivalent for iodine, and I've looked, but have yet to find any. Have yet to get around and trying this last.
i love this video, because I‘m looking for oxidants to screen for my research… what about Bi(NO3)3 * 5 H2O, oxone, Mn(OAc)3? Reductant tiers would also be cool!
How about yellow Mercuric Oxide? We use it sometimes for preparing aryldiazomethanes from hydrazides. I started opting for using manganese dioxide but it's a bit harder to make in sufficiently active form, but it's much healthier alternative.
Persulfate is necessary to make polyacrylamide gels which are necesary to run western blots, so without we don't have the best tool we have for visualizing and measuring proteins. We use the ammonium salt tho, no idea if it matters.
dude love the videos, I wanna hear more about your grad school experience and more about you, is there a possibility you'll make videos about that stuff?
Hi there, next couple days I ll start my first job as an analytical chemist...I'll be dealijg a lot w HPLC and GC.. I love watching ur channel..keep u p the good work
Benzoyl peroxide at least used to be used in special effects pyro to simulate a smoky gasoline deflagration. Sounds a bit sketchy but I've never heard about any industry incidents with it, despite everything about film making usually being more than a little slapdash when it comes to process and safety.
It really is cool, in that it boils at 216K. O2F2 fans simply must read www.andrew.cmu.edu/user/jklein2/O2F2.pdf - Dr. A.G. Streng's study of, as Derek Lowe puts it, mixing O2F2 with everything you wouldn't mix it with. As to ClF3, John Clark claims it "consistently lives up to its reputation." Which would be nice if its reputation was "well, it's not QUITE as bad as nuclear weapons..."
N2O4 seems like it might be worth a mention as well. For a long time it was used with UDMH as a rocket fuel because it's an excellent oxidizer and it's stable to store. It's also extraordinarily nasty stuff, but hey, there's always a downside. 8-)
@@johannesgutsmiedl366 Many in the US and Europe. N204/MMH is used in most bipropellant thrusters including for CST-100, Dragon and Dragon v2, X-37b, Orion. Japanese HTV uses bipropellant thrusters. Many commercial satellites use bipropellant thrusters, either alone or in combination with hydrazine monopropellant RCS or electric station keeping.
The only thing I heard about 3-chloroperoxybenzoic acid as to why we use it over just the plain peroxybenzoic acid is due to how much more stable it is when that chloride atom is added at the 3 position. I'm not sure WHY this creates stability, but I do know that the shelf stability and degradation rate is orders of magnitude better than just peroxybenzoic acid
@@That_Chemist yeah, it’s even described on some sites as “indefinitely stable if stored under proper temperatures and conditions.” So I think that’s the main reason. Regular PBA will degrade over time even with the best storage conditions. Also, it’s worth pointing out that most 3-chloroperoxybenzoic acid is actually not a pure solid. It’s sold as something like 75% 3-chloroperoxybenzoic acid by weight with 25% 3-chlorobenzoic acid and water as the remaining weight. This co-crystallizes into a mixed composition solid hydrate and that is what is sold commercially. I believe this also has a stabilizing effect. Sorta like how perchloric acid loses a lot of its more dangerous properties if diluted to 70% or lower.
Dilute potassium permanganate in alkaline solution is excellent for cleaning glassware. After I adopted it I only need to use sulfochromic mixture in some very exceptional instances. I use it far more often than any other oxidant. S tier for me.
It can sure make a vehicle traverse 1320 feet of pavement very quickly, sometimes leaving a trail of molten aluminum that used to be the pistons. Great oxidizer and refrigerant.
In my case, monopersulfate is in S tier since it can oxidize amino group on furazan or azoles directly to azoxy linkage, nitro group or produce n-oxides.
I would think that mCPBA is more stable against decomposition on its own and thus is more convenient to store that's why it's used instead of other peroxybenzoic acids. J. Org. Chem 1964, 29, 7 pp. 1976 - 1979 has an article praising mCPBA-s stability in different solvent conditions as being remarkable so maybe that's it.
DMP is the best if you want to make aldehydes/ketones - great selectivity, easy to workup and purify afterwards. Downsides - relatively expensive, decomposes.
you can make it yourself in a research context, and it can be repurified with Ac2O if the stuff you have decomposes a bit - just use a solvent that dissolves DMP but not IBX
Oxygen is an automatic S tier, because we breathe it. So is ozone, the less stable brother of oxygen, which is also used in disinfection. So is fluorine, the oxidant of oxygen. Chlorine is S tier, as it's used for disinfection. Bromine is S tier, as it's the "scary cool liquid element". Iodine is S tier, as it's used in disinfection of wounds. So, basically, all (non-radioactive) halogens are an automatic S tier from me. Water is an S tier, because we live with it. t-Butyl hypochlorite is a B, as it's spontaneously flammable. Sodium hypochlorite is B, as it's unstable. Chlorine trifluoride is an automatic, unforgettable, S+, so is chlorine pentafluoride. Perruthenate looks cool with ruthenium(VII), so A tier. Chromyl chloride and chromyl chloride are A tier, but dimanganese heptoxide is an S tier, both as an oxidant, and as an explosive. Selenium dioxide is F, as it smells bad. Tetraacetoxylead/lead tetraacetate is a C, as it's a lead compound. DMSO is a B/C tier, because of the garlic smell if absorbed by skin. DDQ is an E tier, as it releases hydrogen cyanide. Dibenzoyl peroxide is used (2-4%) in skin care products, so an automatic A tier. 3-chloroperbenzoic acid, mCPBA, is an A tier. So is perbenzoic acid, although that melts at 40-42°C. Osmium tetroxide is a C tier, as it's toxic, smells bad, and was claimed to be used by the al-Qaeda in 2004. Though, we can't forget that it's a good oxidant and a good reagent to make 1,2-diols from alkenes.
The 1st time I used m-CPBA, I quenched with NaHCO3. During the column chromatography, I felt painful and stupid. If anyone sees this, I recommend you to use Na2CO3 because the basicity of NaHCO3 is not enough. During the extraction and sepration, the organic acid will stay in the organic phase, and they can't be separated by chromatography.
I listened to this whole thing and I don't know if the OG Kno3 was mentioned! Back in the day anarchist cookbook go to! Made many a... device from that.
I just got stuck on that, thinking about things to do with my Te, would Tellrillic(bad spelling) acid work the same, and what about chirality and allylic position, how does that work? makes me think of going for my MCSE and being told that tokens in token ring networks go counterclockwise while showing a picture of an Ethernet thinnet 'T' connector ..... what is convention and what is physics?
I once worked in a lab where they had a teflon ampule with ClF3. It was behing a glass shield with big sign " DO NOT TOUCH" on it. And behind it was another glass shield with even bigger "DO NOT FUCKING TOUCH" on it. Chemists are memers.
Ammonium cerium nitrate is such a good oxidant. It's powerful but like...pretty well behaved. If you aren't stupid with it it's not that dangerous despite being really efficient.
Ah, organic sulfides....LOVE'em! Incidentally, I invented what I believe to be the very best perfume ever produced. It employs a skatole base scent in a mercaptan carrier. I call it, "Fecal Fantasy." I don't understand it, but I haven't received any offers from manufacturers to produce & market it.... :(
0:55 my poor boy DMSO💀aside from the smell and emission of carbon monoxide, the Swern oxidation's byproducts are gases and water-soluble ions only so the separation is relatively simpler
Fun fact: Sodium perborate used to be (and perhaps still is) the principle ingredient in persil washing powders because it hydrolyses to release hydrogen peroxide as the active bleaching agent. In fact the name persil derives from “PERborate” and “SILicate”.
I think IBX should rank higher, because it is really good at oxidizing alcohol groups to aldehydes or ketones. Low solubility in solvents like acetonitrile and a easy work up via chromatography leads to very good yields and high purity. Nice mechanism btw 😁
It is a little volatile tho-an easy way to prank new interns is asking them to determine its melting point(via the device and in small amounts ofc). Decomposes explosively :D
@@That_Chemist the one i used wasn't prepared by me and stored for 5 years in a fridge 😅 Still worked great though, although it was not pretty to look at. Always worked in like 2,5 eq eccess and did the workup directly after stopping the reaction. Thin layer chromatography was used for monitoring.
Would appreciate folks thoughts on peroxycarboxylic acids, particularly any thoughts on safe handling and avoiding common dangers. Primarily peracetic acid. I am starting to work with peracetic at 30%+ (w/w) and don't have any safety instructions from my PI (industrial research, not academic setting). I've done my own research, but would love some firsthand anecdotal accounts from some lab rats and not just vendors.
Just casually working with elemental chlorine and shitloads of HF at a semiconductor facility. It's kinda nice to walk under thin gas lines with oxygen, boron trichloride, elemental chlorine and a bunch of other stuff, not always toxic/corrosive, but definitely not very good if something goes wrong. Am i afraid of this stuff? Absolutely not, just do not punch holes in HF tanks and do not vent chlorine into cleanrooms😅 Some day someone dropped an 80l acetone barrel while carrying it around, so we suddenly had a nice friendly atmosphere in there😂 It took almost 4 hours to fully drain/evaporate and to ventilate the building
Macrophages / other professional phagocytes produce lysosomes filled with degradative chemicals and enzymes that fuse with phagosomes containing whatever the cell decided to eat, and those fuse to form phagolysosomes where the actual digestion of the threat takes place. i know they've got hydrogen peroxide, but I'm not certain about sodium hypochlorite.
idk if this is a good link or not, but you can check it out - www.chlorine.org/human-immune-system-uses-chlorine-bleach-active-ingredient-kill-bacteria/
We have like….an entire KILO of CrO3 in my lab and it’s terrifying. Although throw a bit in some water and acidify it’s and you’ve got instant chromic acid. Cleans glass Frits like NOBODYS business tho, nothing even comes close to doing that cleaning as well as chromic acid despite the toxicity
Yeah I just want to say I love your channel I know nothing about chemistry but watching Tier List makes me learn about the names of the chemicals..... this might sound stupid to you but is there an oxidizer that doesn't contain oxygen and would even be called an oxidizer ?? Luv from the Netherlands 👊🏾
No davis reagent on this list? It's a great reagent to oxidize alpha carbons besides a carbonyl group resulting in a alpha hydroxy carbonyl. Also I would put manganese heptoxide in F tier. I cant think of any use of it in the lab.
Perchloric acid kinda covers the solid perchlorates as well. I recently made some LiClO4 from HClO4 and LiCO3. Apparently it's the most energy dense perchlorate and is awesome for rocket engines except it's crazy hygroscopic and has to be sealed so it doesn't just dissolve itself with atmospheric moisture. Think I'll build a little engine with it.
Isnt the combination of H2O2 and H2SO4 the peroxymonosulfuric acid? You are certainly a many times better chemist than I am, but I considered this to be identical.
When photo masks are made, they start with a layer of chromium on quartz. Then they apply photoresist and expose it with light to make a pattern in the photoresist. Then they etch the chromium to create a pattern, which is used as a template to make chips.
I would be interested to know if anyone can shine some light, for an amateurs perspective, what is aluminum blacking/stain/darkening? AVE and This Old Tony did a video recently. I've had similar experience and seeing people handle metal stains and darkening chemicals like it's water!?! Curious about danger Factor sometimes it boils like it's hydrogen peroxide when you dip a piece of metal into the solution??? "Will it black an entire aluminum part" that should be the name of the episode
IBX is easily S tier, is such a clean oxidant - it + the thing you want oxidised in DMSO, stir at RT for ~ 30 mins then dilute with water, filter and extract with ether - it has helped me out of a few tight spots
Depends on the context. IBX/DMP are great for smaller scale academic/medicinal chemistry routes. For us process chemists not so much a S tier reagent :)
"This is an evil chemical. It burns sand." I always refer to the article "Sand Won't Save You This Time" whenever someone mentions ClF3.
"Let's put it this way: during World War II, the Germans were very interested in using it in self-igniting flamethrowers, but found it too nasty to work with. It is apparently about the most vigorous fluorinating agent known, and is much more difficult to handle than fluorine gas. That’s one of those statements you don’t get to hear very often, and it should be enough to make any sensible chemist turn around smartly and head down the hall in the other direction."
It once burned through 1 foot of concrete and 3 feet of gravel after a large spill. 😧
@@joeylawn36111 It also happily burns asbestos
The great comment of how to handle an accident involving ClF3 - “I have always recommended a good pair of running shoes.” -Dr John D. Clark
Originally from the book "ignition".
"Ozone smells the way a lethal radiation dose feels." -Ex&F
Yeah
Smells like an old slot car track.
The arcing of the contact brushes generated lots of ozone.
When I was a lifeguard in high school, we just chlorinated our pool with a giant tank of cl2 (like the size of a liquid n2 tank), it was terrifying to change out.
why the fuck did they chlorinate the pool with chlorine gas?
it's gonna be one hell of a desinfactant, but thry forgot they might desinfact you and you from the face of the earth
@@VerbenaIDK Chlorine gas pool chlorinators are very common on public pools.
I've also been to a country where what I assume was a public water supply shed had a tank of chlorine gas *outside* viewable from the road, with some pipe going in.
It terrified me.
Only capitalism would make high schoolers change giant tanks of Cl2
@@gliiitched this is a really dumb take.
It's a pretty low-brow joke and I would have thought I'd stop finding it funny, but "D for DMSO" and suchlike cracks me up a little every time. It's the deadpan delivery I think; it really complements the absurdist nature of these presentations.
my low broke joke with dmso: ever since someone introduced me into the DMSO song version of DVNO i can never listen to it normally without smiling and people are always creeped out, but explaining to them is way to hard and makes it just worse and even more funny for me.
B for Bromine
@@contomo5710 what about DMSO version of YMCA?
@@NoNameAtAll2 even harder to explain, also somehow doesnt fit the vibe
I guess it's kinda funny to me because he talks about all this cool educated chemistry stuff with the jargon and anecdotes, and then justifies the placement with "starts with this letter" lol. I do think the bit has run its course tho
Fun fact: F is such a strong oxidizer NASA experimented with it as a rocket fuel. It was used with H and liquid Li and produced the highest specific impulse of any chemical rocket. However it was never used in practice because a failure means covering large areas, or even the launch site and accompanying engineers, in F and Li which is really bad for obvious reasons.
Anyone curious about rocket fuels is required to read Ignition! by John D Clark, 1972. Here is an excerpt from a section about fluorine:
It can be contained in several of the structural metals: steel, copper, aluminum, etc. because it forms, immediately, a thin, inert coating of metal fluoride which prevents further attack. But if that inert layer is scrubbed off, or melted, the results can be spectacular. For instance, if the gas is allowed to flow rapidly out of an orifice or a valve, or if it touches a spot of grease or something like that, the metal is just as likely as not to ignite and a fluorine-aluminum fire is something to see. From a distance.
[...]
The development of large fluorine motors was a slow process, and sometimes a spectacular one. I saw one movie of a run made by Bell Aerosystems, during which a fluorine seal failed and the metal ignited. It looked as though the motor had two nozzles at right angles, with as much flame coming from the leak as from the nozzle. The motor was destroyed and the whole test cell burned out before the operators could shut down.
Chlorine trifluoride also gives out hot HF gases when it reacts with any moisture. Like in air or on your skin
Kinky
I think part of the reason mcpba is more popular is its high melting point. Perbenzoic acid melts at ~40 degrees whereas mcpba melts at 90 or so.
> Air is super convenient to handle
Love the vids for these moments
The similarity between hydrogen peroxide and FOOF is more surprising than it should be.
Fuming nitric acid is also a great oxidizer for rocketry, as is N2O4. ClF3 was once tried as an oxidizer, and had excellent performance, but it is of course truly evil and was not very popular.
If you're interested in reading about the terrifying propellant chemistry that went on in the early days of rocketry, check out the book *Ignition!* by John D. Clark.
Cool, thanks!
Maybe post a link to it in the discord so other people can enjoy it :)
On the subject of rocketry, hydrogen peroxide decomposed with potassium permanganate catalyst deserves an honorable mention, not as an oxidiser but as a means of driving turbopumps for main fuel/oxidizer. Used in torpedoes, missiles, and the early days of rocketry, it's still used in the Soyuz rocket (1950s to present) to generate oxygen/steam at high pressure to drive the propellant pumps. In other words, the "elephant's toothpaste" reaction has engineering uses.
Hydrogen peroxide has been used as an oxidiser in rocketry but the major use is catalytic decomposition for driving turbopumps, or as a monopropellant.
I really can imagine an hydrazine - ClF3 rocket. Rocket and chemical weapon at same time
The concrete was on fire!
Great book.
Oxone really should have been on the list! It’s high molar mass, i.e. large amounts are necessary, which is a downside but it’s very useful, non-toxic and even used in pools. Who doesn’t like pools? S-tier for me!
(And it can even be purified to stay as reactive but using smaller amounts)
yes. easy to generate using germicidal lamps and/or spark gaps.... and don't you have to be at a low pressure to create singlet oxygen?
@@petevenuti7355 You are confusing oxone and ozone I think. Very similar names.
@@zockertwins yup, I was moving too quick, multitasking too much earlier today. Not quite squirrel gone plaid but... Yeah , easy error....
6:42 I'm thinking of the 2 times when a room mate in our students' dorm cleaned the mold in the shower and the whole hallway reeked of clorine gas. Not the typical pool smell, but real clorine. First I thought I was imagining things (why the heck would I smell clorine at home?) but then I checked the hallway and the shower and was greeted with a cloud. I opened all windows (they hadn't done that in the shower) and the backyard door before I furiously send some massages in our WhatsApp group. I remember how terrified they reacted, when I told them, that they produced real clorine gas. I don't know how the did it, but I guess they mixed different cleaners.
Yikes
@@That_Chemist I have 2 budgies so I was quite worried that I could smell it in my room. I had to cover the slit beneath my door where the chlorine came through with a towel to protect them (at least a little).
It's easily done. Hypochlorite bleach and acid down the toilet at the same time. Hypochlorite will always have a big warning about this somewhere on the bottle.
Bleach/Javel (Sodium hypochlorite) reacts with acidic drain/toilet cleaners to release Chlorine gas.
Potassium permanganate and hydrogen peroxide solutions also make good post treatments for sealing trivalent chromium coatings. Any oxidising agent would really, but weak solutions of those mentioned agents are good.
Edit: (conversion coatings on aluminium) I should’ve mentioned the substrate
Thanks for the addition of names it really helps.
I figured it would be nice for non-experts
Dupont at their Teflon plant outside of Parkersburg, WV uses 10% Fluorine Gas with 90% nitrogen in Small trailers. Gentlemen told me they actually wanted to use a higher ratio but anything higher than 10% caused issues. He went on to say if they had a trailer leak it would overwhelm the entire 50 acre site in 10 minutes.
When they would need to unload the trailer it would be back up to an Overgrown Fume hood so they could connect the trailer in a sealed environment. This fume hood was actually located outside the building incase of a leak.
dang that is scary
Potassium persulfate is a really convenient source of peroxysulfuric acid. I would use this sometimes as a way to clean out dirty, clogged up fritted glass filter funnels: Add some potassium persulfate to the funnel, pour some concentrated sulfuric acid in after it, and heat it up gently with an electric hot air heat gun until the persulfate crystals dissolve in the acid. Then just let the liquid dribble through the fritted glass, and on its way it will oxidize anything stuck in there. Really easy and very effective.
16:38 Because it's just using air/
it's great, it's free, it's there.
This man is spitting bars, as they say.
lmao
I wouldn't put oxygen in the S tier, it can destroy too many things. Too many of my copper nanoparticles syntheses have failed because of it :(
Should be mentioned: Concentrated perchloric acid will explode when heated. I once tried to clean a bit of expensive glassware with perchloric acid. Put the apparatus filled with the acid in a microwave. I thought I was being careful by trying 'only' 20s first. About 10s in, the whole thing exploded.
An interesting oxidizer is ferrate salts. Iron really does not like being in the +6 oxidation state. It is a stronger oxidant than permanganate. A new manufacturing process has recently been developed, so it's not as expensive as it used to be. A promising industrial application is as a lethal oxidizer in water purification. Since it reduces to rust in water, a film of rust settles in the water, trapping particulates and sinking them to the bottom of the container. Since it's only iron, unlike permanganate or chlorine, it's nontoxic. A big con is that it decomposes in water, esp. acidic solutions, and it's mildly hygroscopic. Keep it dry, or keep it alkaline.
interesting!
Yess!!! The DMSO is a mild oxidant but perfect when is a methionine in the reaction and you have to make a cys-cys breach in a solution also to conserve the cys in a reduced state
tier lists are so cool and fun to watch and educational, thank you. unfortunately i can not help you with ideas for tier lists since im not too deep into the subject, only introductory lab courses, hmm i believe you already did solvents right? glassware as well i believe, damn.... something in the realm of physical chemistry or inorganic chemistry? those lanthanides with relativistic effects on their electrons do sound cool tbh....
thank you for everything :)
I got to use Potassium Ferricyanide in my undergrad analytical chem class. We used it with glucose oxidase to measure glucose. No idea if it is a good oxidizer, but I used it.
FINALLY I KNOW WHAT THESE ARE NOW, I'm a FedEx driver and I deliver to a hospital every day. I'd say maybe once or twice a week I have to go through a special procedure to deliver hazardous materials to them, and most commonly it has a big "oxidizer" label on it
That chemist not recalling phagolysosome is hilarious.
hey >:(
hey cut him some slack..... lysome was the first thing that popped into my mind... at least he didn't say it if he didn't know , right? .... I was going to look it up but you beat me to it.
Singlet oxygen is so reactive it's essentially always a short-lived intermediate, usually in photochemistry, in my experience. What is anyone doing that involves gathering up a significant amount of it all at once?
mixing bleach and H2O2
at lower temps, it exists for longer
@@That_Chemist No, I meant for what purpose. Seems way more convenient to make it photochemically unless you're doing something very specific.
I was just thinking about the red light in some high voltage discharge... didn't even know of it's existence as an intermediate before.....
10:56 *googles how to make singlet oxygen*
as one does
Definitely make more Toxic videos! they're great. Data fraud doesn't get nearly enough attention, even within academia. Hopefully raising awareness can help prevent it
I hope so!
What about FOOF?
Not only is it a powerful oxidizer, it decomposes to F2 and O2 so you get a triple oxidation whammy.
I have several (working) antique violet ray units, basically a hand held "medical" tesla coil, and as such creates ozone during use. They had different electrodes to use depending on what part of the human body they were "treating" and it could cure all... For example, did you have breathing problems? Here's a twin nozzled adapter that allows you to breathe lovely ozone in through each nostril! Because 3 oxygen molecules are better than 2 right! 😳
3 oxygens are too many
Interesting and thanks. Noticed that you mention Chlorine a couple of times. There's a sort of trick that you can do with Ferric Chloride. An older one, been around since at least the 1930s. If you heat up this material to about 70 degrees C or so, you get a sort of equilibrium that goes: Ferric Chloride Ferrous Chloride. An acquires solution of this material will work nicely to etch copper printer circuit boards. You get cuprous chloride and ferric chloride. If you pour off the liquid, while still warm, you can rinse off your board. I suppose there might be an equivalent for iodine, and I've looked, but have yet to find any. Have yet to get around and trying this last.
i love this video, because I‘m looking for oxidants to screen for my research… what about Bi(NO3)3 * 5 H2O, oxone, Mn(OAc)3? Reductant tiers would also be cool!
My uni professor introduced us to both TPAP and CAN in our final year, pretty cool oxidants
same for MnO2, lol, he was trying to show off a bunch of rarer agents.
How about yellow Mercuric Oxide? We use it sometimes for preparing aryldiazomethanes from hydrazides. I started opting for using manganese dioxide but it's a bit harder to make in sufficiently active form, but it's much healthier alternative.
Persulfate is necessary to make polyacrylamide gels which are necesary to run western blots, so without we don't have the best tool we have for visualizing and measuring proteins. We use the ammonium salt tho, no idea if it matters.
dude love the videos, I wanna hear more about your grad school experience and more about you, is there a possibility you'll make videos about that stuff?
potentially
ClF3 is excellent for lighting concrete on fire.
I'll write in my will to add that to my ashes.... 🔥 burn twice
and test engineers
I don't know why, but i find these videos so calming that I often watch them as ASMR
So what I’m hearing is that I should do a podcast
@@That_Chemist I'm not much of a podcast watcher but perhaps
You sir have just gained a sub! Taking the best subject in college (Orgo) and making it even better!
Welcome aboard!
Suggestion: Tetranitromethane!
It isn't really used often, but an absolute monster of an Oxidizer!
From formal point of view the strongest one-electron oxidizing agent is F2.
Looks like Tyranosaurus Rex in redox reactions.
Hi there, next couple days I ll start my first job as an analytical chemist...I'll be dealijg a lot w HPLC and GC.. I love watching ur channel..keep u p the good work
Awesome
Benzoyl peroxide at least used to be used in special effects pyro to simulate a smoky gasoline deflagration. Sounds a bit sketchy but I've never heard about any industry incidents with it, despite everything about film making usually being more than a little slapdash when it comes to process and safety.
I really don’t know too much about the chemistry of pyrotechnics but that’s really interesting
6:05 woah I only ever thought of hydrogen gas as a reducing agent but I guess it's all relative
I missed dioxygen difluoride. It oxidzes and is structured F-O-O-F. How can any Oxidizer ever be cooler?
It really is cool, in that it boils at 216K.
O2F2 fans simply must read www.andrew.cmu.edu/user/jklein2/O2F2.pdf - Dr. A.G. Streng's study of, as Derek Lowe puts it, mixing O2F2 with everything you wouldn't mix it with.
As to ClF3, John Clark claims it "consistently lives up to its reputation." Which would be nice if its reputation was "well, it's not QUITE as bad as nuclear weapons..."
I mean krypton difluoride directly oxidizes gold to Au2F10 which is pretty cool. And also just a stronger oxidizer than foof.
@@MrDJAK777 I'd like to know where they manufacture krypton difluoride so I can maintain a safe distance!
N2O4 seems like it might be worth a mention as well. For a long time it was used with UDMH as a rocket fuel because it's an excellent oxidizer and it's stable to store. It's also extraordinarily nasty stuff, but hey, there's always a downside. 8-)
There are still a bunch of N2O4/MMH+UDMH powered rockets in operation, just none in the US or Europe anymore :)
@@johannesgutsmiedl366 Many in the US and Europe. N204/MMH is used in most bipropellant thrusters including for CST-100, Dragon and Dragon v2, X-37b, Orion. Japanese HTV uses bipropellant thrusters. Many commercial satellites use bipropellant thrusters, either alone or in combination with hydrazine monopropellant RCS or electric station keeping.
Potassium ferricyanide is also one of the components of cyanotype sensitizer and Prussian blue is a lovely pigment.
The only thing I heard about 3-chloroperoxybenzoic acid as to why we use it over just the plain peroxybenzoic acid is due to how much more stable it is when that chloride atom is added at the 3 position. I'm not sure WHY this creates stability, but I do know that the shelf stability and degradation rate is orders of magnitude better than just peroxybenzoic acid
Useful to know!
@@That_Chemist yeah, it’s even described on some sites as “indefinitely stable if stored under proper temperatures and conditions.” So I think that’s the main reason. Regular PBA will degrade over time even with the best storage conditions.
Also, it’s worth pointing out that most 3-chloroperoxybenzoic acid is actually not a pure solid. It’s sold as something like 75% 3-chloroperoxybenzoic acid by weight with 25% 3-chlorobenzoic acid and water as the remaining weight. This co-crystallizes into a mixed composition solid hydrate and that is what is sold commercially. I believe this also has a stabilizing effect. Sorta like how perchloric acid loses a lot of its more dangerous properties if diluted to 70% or lower.
Dilute potassium permanganate in alkaline solution is excellent for cleaning glassware. After I adopted it I only need to use sulfochromic mixture in some very exceptional instances. I use it far more often than any other oxidant. S tier for me.
I find that a typical KOH/water/isopropanol baths work best
20:35 We've had one, yes. But what about second osmium tetroxide?
Methyl ethyl ketone peroxide --- used often initiation polymer resin
You should do protecting groups next
I second this!!!
Yeah maybe
The semiconductor industry uses a lot of ClF3 for cleaning purposes. On the other hand they seem to use every nasty compound ever invented.
I heard a talk on fluorinated etchants - it’s super interesting!
N2O is by far my fav oxidant. its also really easy to make on the spot
Don't make me laugh.
It can sure make a vehicle traverse 1320 feet of pavement very quickly, sometimes leaving a trail of molten aluminum that used to be the pistons. Great oxidizer and refrigerant.
chlorine trifluoride!!!! glad it was included
In my case, monopersulfate is in S tier since it can oxidize amino group on furazan or azoles directly to azoxy linkage, nitro group or produce n-oxides.
22:39 It's thought that peroxymonosulfuric acid is the active ingredient in piranha solution.
I'm missing one of ChemicalForce's favorites: potassium superoxide.
I would think that mCPBA is more stable against decomposition on its own and thus is more convenient to store that's why it's used instead of other peroxybenzoic acids. J. Org. Chem 1964, 29, 7 pp. 1976 - 1979 has an article praising mCPBA-s stability in different solvent conditions as being remarkable so maybe that's it.
DMP is the best if you want to make aldehydes/ketones - great selectivity, easy to workup and purify afterwards. Downsides - relatively expensive, decomposes.
you can make it yourself in a research context, and it can be repurified with Ac2O if the stuff you have decomposes a bit - just use a solvent that dissolves DMP but not IBX
Oxygen is an automatic S tier, because we breathe it. So is ozone, the less stable brother of oxygen, which is also used in disinfection. So is fluorine, the oxidant of oxygen.
Chlorine is S tier, as it's used for disinfection. Bromine is S tier, as it's the "scary cool liquid element". Iodine is S tier, as it's used in disinfection of wounds. So, basically, all (non-radioactive) halogens are an automatic S tier from me.
Water is an S tier, because we live with it.
t-Butyl hypochlorite is a B, as it's spontaneously flammable. Sodium hypochlorite is B, as it's unstable.
Chlorine trifluoride is an automatic, unforgettable, S+, so is chlorine pentafluoride.
Perruthenate looks cool with ruthenium(VII), so A tier.
Chromyl chloride and chromyl chloride are A tier, but dimanganese heptoxide is an S tier, both as an oxidant, and as an explosive.
Selenium dioxide is F, as it smells bad.
Tetraacetoxylead/lead tetraacetate is a C, as it's a lead compound.
DMSO is a B/C tier, because of the garlic smell if absorbed by skin.
DDQ is an E tier, as it releases hydrogen cyanide.
Dibenzoyl peroxide is used (2-4%) in skin care products, so an automatic A tier.
3-chloroperbenzoic acid, mCPBA, is an A tier. So is perbenzoic acid, although that melts at 40-42°C.
Osmium tetroxide is a C tier, as it's toxic, smells bad, and was claimed to be used by the al-Qaeda in 2004. Though, we can't forget that it's a good oxidant and a good reagent to make 1,2-diols from alkenes.
PCC is great but dealing with it for a column is a nightmare... I only used it once and then switched to DMP 😂
Is hydrogen peroxide toxic when it's diluted to like 8%? I'm trying to find a chemical to get rid of my mold problem that does not contain chlorine.
The 1st time I used m-CPBA, I quenched with NaHCO3. During the column chromatography, I felt painful and stupid. If anyone sees this, I recommend you to use Na2CO3 because the basicity of NaHCO3 is not enough. During the extraction and sepration, the organic acid will stay in the organic phase, and they can't be separated by chromatography.
It’s also good to quench the remaining Peracid with sulfite
I listened to this whole thing and I don't know if the OG Kno3 was mentioned! Back in the day anarchist cookbook go to! Made many a... device from that.
SeO2 oxidation is also known as Riley oxidation and it works wonders! Can we do a series on Top 50 named reactions?
I just got stuck on that, thinking about things to do with my Te, would Tellrillic(bad spelling) acid work the same,
and
what about chirality and allylic position, how does that work?
makes me think of going for my MCSE and being told that tokens in token ring networks go counterclockwise while showing a picture of an Ethernet thinnet 'T' connector ..... what is convention and what is physics?
I'm terrible with names, I would have had a hard time with that if I continued biochemistry studies....
My dad used to use potassium permanganate to disinfect drinking water because it was relatively cheap for him and water was really dirty in India.
I once worked in a lab where they had a teflon ampule with ClF3. It was behing a glass shield with big sign " DO NOT TOUCH" on it. And behind it was another glass shield with even bigger "DO NOT FUCKING TOUCH" on it. Chemists are memers.
Man this gives me motivation to finish my chem degree
Ammonium cerium nitrate is such a good oxidant. It's powerful but like...pretty well behaved. If you aren't stupid with it it's not that dangerous despite being really efficient.
Ah, organic sulfides....LOVE'em! Incidentally, I invented what I believe to be the very best perfume ever produced. It employs a skatole base scent in a mercaptan carrier. I call it, "Fecal Fantasy." I don't understand it, but I haven't received any offers from manufacturers to produce & market it.... :(
Ozone tubes in series multiple 10g tubes
Wtf you dont even understand it turns water into goo
I hardly ever comment, but again, you should be on the safety third podcast. WITH NIGEL THERE! We'd all love to hear you all talk!!!
Good video, balanced tier list 👍👍
0:55 my poor boy DMSO💀aside from the smell and emission of carbon monoxide, the Swern oxidation's byproducts are gases and water-soluble ions only so the separation is relatively simpler
8:49 this guy is scary in that it burns anything and everything
Fun fact: Sodium perborate used to be (and perhaps still is) the principle ingredient in persil washing powders because it hydrolyses to release hydrogen peroxide as the active bleaching agent. In fact the name persil derives from “PERborate” and “SILicate”.
Same with sodium percarbonate.
I think IBX should rank higher, because it is really good at oxidizing alcohol groups to aldehydes or ketones. Low solubility in solvents like acetonitrile and a easy work up via chromatography leads to very good yields and high purity. Nice mechanism btw 😁
It is a little volatile tho-an easy way to prank new interns is asking them to determine its melting point(via the device and in small amounts ofc). Decomposes explosively :D
I tried decomposing it thermally but it didn't do anything crazy - even though I made mine using bromate
@@That_Chemist the one i used wasn't prepared by me and stored for 5 years in a fridge 😅
Still worked great though, although it was not pretty to look at. Always worked in like 2,5 eq eccess and did the workup directly after stopping the reaction. Thin layer chromatography was used for monitoring.
Would appreciate folks thoughts on peroxycarboxylic acids, particularly any thoughts on safe handling and avoiding common dangers. Primarily peracetic acid. I am starting to work with peracetic at 30%+ (w/w) and don't have any safety instructions from my PI (industrial research, not academic setting). I've done my own research, but would love some firsthand anecdotal accounts from some lab rats and not just vendors.
Just casually working with elemental chlorine and shitloads of HF at a semiconductor facility. It's kinda nice to walk under thin gas lines with oxygen, boron trichloride, elemental chlorine and a bunch of other stuff, not always toxic/corrosive, but definitely not very good if something goes wrong. Am i afraid of this stuff? Absolutely not, just do not punch holes in HF tanks and do not vent chlorine into cleanrooms😅
Some day someone dropped an 80l acetone barrel while carrying it around, so we suddenly had a nice friendly atmosphere in there😂 It took almost 4 hours to fully drain/evaporate and to ventilate the building
XeF2 > F2 its a Solid, you can weigh it and you have all the benefits of fluorine + noble Gas compound credits ;D
Macrophages / other professional phagocytes produce lysosomes filled with degradative chemicals and enzymes that fuse with phagosomes containing whatever the cell decided to eat, and those fuse to form phagolysosomes where the actual digestion of the threat takes place. i know they've got hydrogen peroxide, but I'm not certain about sodium hypochlorite.
idk if this is a good link or not, but you can check it out - www.chlorine.org/human-immune-system-uses-chlorine-bleach-active-ingredient-kill-bacteria/
Rozen's reagent is an excellent O atom transfer reagent.
Shlomo is a character
1:49 And it can etch stone!
How about urine? Here in Seattle the homeless sometimes urinate on people's doors or sidewalks and it really does a number to some of the materials.
I've only really used ozone to kill persistent fungi/amoebas in biochem labs, lol.
Osmium tetroxide should be higher because it can easily be used catalytically, so the price and toxicity is a lot less of a problem.
We have like….an entire KILO of CrO3 in my lab and it’s terrifying. Although throw a bit in some water and acidify it’s and you’ve got instant chromic acid. Cleans glass Frits like NOBODYS business tho, nothing even comes close to doing that cleaning as well as chromic acid despite the toxicity
Yikes
What about Ammonium Perchlorate or Dinitrogen Tetroxide? Those a very popular oxidizers.
+ honorable mention: Ammonium Dinitramide.
don’t mind me, just a very lost economist passing through
Yeah I just want to say I love your channel I know nothing about chemistry but watching Tier List makes me learn about the names of the chemicals..... this might sound stupid to you but is there an oxidizer that doesn't contain oxygen and would even be called an oxidizer ?? Luv from the Netherlands 👊🏾
Yes! Chlorine would be an example of one :)
Oxidation just means the loss of electrons
No davis reagent on this list? It's a great reagent to oxidize alpha carbons besides a carbonyl group resulting in a alpha hydroxy carbonyl. Also I would put manganese heptoxide in F tier. I cant think of any use of it in the lab.
yeah I wanted to include an oxaziridine but it was already pretty full
Did I miss Ammonium Perchlorate? I’ve used probably 100 lbs in high power rocket motors
Perchloric acid kinda covers the solid perchlorates as well. I recently made some LiClO4 from HClO4 and LiCO3. Apparently it's the most energy dense perchlorate and is awesome for rocket engines except it's crazy hygroscopic and has to be sealed so it doesn't just dissolve itself with atmospheric moisture. Think I'll build a little engine with it.
Isnt the combination of H2O2 and H2SO4 the peroxymonosulfuric acid?
You are certainly a many times better chemist than I am, but I considered this to be identical.
I’m not sure if it definitely forms caros acid from mixing the two
Ceric ammonium nitrate is used to etch chromium in the semiconductor industry. CZcams wouldn't exist without it!
It's part of the photolithography process. This video explains it well. czcams.com/video/foMT8gLYxBY/video.html
When photo masks are made, they start with a layer of chromium on quartz. Then they apply photoresist and expose it with light to make a pattern in the photoresist. Then they etch the chromium to create a pattern, which is used as a template to make chips.
Could you to the same (probably a shorter video) and focus on oxidizers for rocket fuel ?
Sorry, not a synthesis chemist. Does nitrous acid form diazonium salts from substituted amines, or just from NH2 groups?
just from NH2 groups - if you have an NHR group, it will form NR-N=O
ammonium perchlorate?
Can anyone tell me plz what do mean those A,B,C and the S in the headings?
I would be interested to know if anyone can shine some light, for an amateurs perspective, what is aluminum blacking/stain/darkening? AVE and This Old Tony did a video recently. I've had similar experience and seeing people handle metal stains and darkening chemicals like it's water!?! Curious about danger Factor sometimes it boils like it's hydrogen peroxide when you dip a piece of metal into the solution???
"Will it black an entire aluminum part" that should be the name of the episode