• N&PD Moderators: Skorpio | thegreenhand

/ethers other then diethyl and diisopropyl

Limpet_Chicken

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Oct 13, 2005
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how do other ethers fare up to diethyl ether and diisopropyl in terms of anaesthetic and/or recreational/intoxicant purposes?

What about the likes of ethoxyhyl ethylisopropyl, butyl/sec/iso/tert-butyl ? do unsaturated bonds affect potency? oral vs inhalational potential.

Lets just ignore dimethyl ether for now, i do have some but I use it for freezing mixtures and methyl...probably unhealthy, not going there, besides i need what i have.

But I love diethyl ether , DIPE or a mix of the two. Wondering how much scope there is for improvement. Sevo was nice for about seven breaths then out like a light. I think I'd like EtOEt with a low admixture of sevo or methoxyflurane. Anyone tried enflurane or desflurane?
 
Diphenyl ether STINKS!
I know this during the day my lab mate trying to dry it in refluxing apparatus with Na pieces, etc.
The floor is then unworkable (6 lab rooms in entire floor) for one whole day.... Idk about anasthetic potential tho.

(And by "stink" i smell diethyl ether as "nice" smell, even! Not much of my friend like Et2O smells like me)
 
Never used diphenyl ether. Hadn't really considered the aryl ethers, or heterocyclic rings even, although why I cannot really say, no logic to it, just hadn't really occurred to me. Was thinking really straight or branched-chain aliphatics, with or without degrees of unsaturation.

Something ideal would be of low (general) anaesthetic potency, but as euphoric as the likes of sevoflurane, high anaesthetic potency isn't a turnoff as long as its not of the type which simply produces unconsciousness.
What does diphenyl ether actually smell OF (as opposed to simply foul. I assume it was actually nasty smelling as opposed to simply penetrating and potently carrying)

I too, love the smell of diethyl ether. DIPE isn't bad either, but better for inhalation (better than orally that is, DIPE inhaled vs DIPE orally I mean) diethyl ether really does smell good enough to drink. Came up with my own cocktail recipe based on
diethyl ether as one of the most important ingredients actually. Sort of like a jagerbomb in theme, I call it a 'manhattan project'=D, the payload being a shot of EtOEt floated in the top of the drink, the rest being tesco own brand lime soda, cheap stuff,
being ideal for some reason, not found any better tasting alternative, along with vodka, and ''Care +'' brand codeine linctus (shocklingly, its actually flavored with chloroform. Even listed on the ingredients. Not sure why its in there, preservative maybe
? Theres enough in that codeine cough syrup to oil out in a greasy looking layer if one pours in the soda and the cough mixture without first adding the vodka.



Lol Pomzazed, something similar has happened to me when doing some work that involved diethyl ether fairly late in the evening, late enough all the people of slightly younger age than I, at the time, were coming back from
school. A then friend of mine came hammering on my door, yammering on asking 'what the hell is that stink? because I can smell it from all the way right down the other end of the road'

Christ knows what the house must have smelled like, because I'd been working in a room, with the door closed, wearing my gas mask of course, I hadn't realized it at the time, but it must have permeated the place pretty thoroughly. I love the smell of the stuff, but that former friend of mine looked like he'd just been mowed by a tank, it seemed to have hit him pretty thoroughly. Not in the anaesthetic sense, but the smell had certainly
slapped him one=D
 
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Divinyl ether seems to have some good properties compared to Et2O, at least according to Wikipedia. Ethyl vinyl ether is also mentioned in that wiki article.
 
From personal experience? have you tried the stuff?

Because I just read the wikipedia article and it seems to have nothing whatsoever to recommend it. Turning into plastic, degradation to acetaldehyde,difficult to regulate.....

Just going on the o-chem feaures, ethylvinyl ether sounds like it would be a far better bet with respects to stability, the lack of the second vinylic function would inhibit autopolymerization as theres no second reactive moiety for the intramolecular condensation to occur between.

But difficult to store, difficult to make, difficult to use, potentially toxic if it ages (although chances are with something like this most of it would end up getting used as a solvent (albeit divinyl ether would IMO likely be a crappy solvent due to the reactivity. After all what good to me (or anyone else for that matter) is a solvent which is likely to react with much that it might ever be used to dissolve :p)

Would this reactivity not also be somewhat likely to render the drug carcinogenic? if it can react with itself and other reactive functional groups, whats to stop it say, doing so with something more vital than its own other end. And couldn't this also deplete glutathione?


What are the reasons you suggested possible superiority to EtOEt/DIPE ?
 
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^ I haven't tried vinyl ether, but I know that it has a much lower blood-gas partition coefficient that ethyl ether, and therefore the induction of "anesthesia" happens faster. Ethyl ether is an inhalant with very slow induction, and you have to breath it in large concentrations to get high fast. This is unpleasant because it irritates mucous membranes and causes excessive salivation.
 
dont use divinyl please, for the sake of crosslinking/alkylation of membrane structures! (More than aliphatic bromides!)

I have ALOT (>50 Litre) of divinyl ether to use in polymer(esp polyester) reactive blending.
They crosslink the OH of polyester effectively inside a twin-screw extruder thus giving higher MW and physical properties of that polymer.


For other ethereal things, I had try
Diethyl Ether: eh surely.. Like it except reeking smell for days from body (forbid working)
THF with little success.(smell is bearable...ok tho)
2-methyl THF is no better albeit more sharp smell
Decafluorodiethyl ether (all H are F): just sniff it and get penetrating and somewhat choking smell so i stopped there.
1,4-dioxane: just sniff it and nothing happens, i never huff that due to carcinogenicity
 
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Yeah, probably better to leave divinyl ether alone... Found some articles that claim sevoflurane is partially degraded to fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether , which is a toxic alkylating agent (possibly because of the vinyl group): http://www.ncbi.nlm.nih.gov/pubmed/8831812 .

I'm not saying that it's particularly good for you to huff any solvents, by the way, but you probably knew that already.
 
Yeah polymath, i know. It was a past experiences during the teens days...
Do diether counts?

I have smelled alot of dioxolanes (1,3-ether in five membered ring)
(All "dioxolane" below are "1,3-dioxolane" but i omitted it)
like 2,2-dimethyldioxolane; 2-ethyl-2-methyldioxolane, 2-phenyldioxolane, 2-methyl-2-phenyldioxolane; 2,2-pentamethylenediyldioxolane (spiro-structure with cyclohexane there); 2,2-tetramethylenediyldioxolane(spiro cyclopentane there)
etc.(more than 20 analogs changing R,R' at 2,2 position to several alkyl/cycloalkyl/aryl/heteroalkyl/heteroaryl)

(P.S. Even plain dioxolane does NOT smell any tint of formaldehyde which is hydrolysis product, seems rather stable.)

They either dont have psychiatric effect or too low of a dose, but i dont plan to huff those thing unless have a good reason to try

Do mixed ether count (for example the 2,2-dimethyloxazolidine) has -O- and -NH- in five membered ring?
This smell so minty and nice, and unlike its reactant (ethanolamine, acetone). Seems stable for year in dry place.
 
I'm not saying that it's particularly good for you to huff any solvents, by the way, but you probably knew that already.

Isn't that more of a myth though? What exactly would be the mechanism for brain damage from inhalant use other than hypoxia if used carelessly (not enough oxygen breathed in). Of course, n-hexane is metabolized into a nasty substance, but that's just an exception rather than the rule. As far as I know, diethyl ether is fairly harmless. Toluene has some mechanism for neurotoxicity, although I don't remember it off the top of my head. Other than that, can't think of much.
 
Isn't that more of a myth though? What exactly would be the mechanism for brain damage from inhalant use other than hypoxia if used carelessly (not enough oxygen breathed in). Of course, n-hexane is metabolized into a nasty substance, but that's just an exception rather than the rule. As far as I know, diethyl ether is fairly harmless. Toluene has some mechanism for neurotoxicity, although I don't remember it off the top of my head. Other than that, can't think of much.

It's probably not as neurotoxic as it's said to be, and most people who have gotten significant neurological damage from toluene had a history of almost daily use for several years. Butane and propane are more likely to cause cardiac arrhythmias that can lead to sudden death. A lot of the neurotoxicity of ethyl alcohol may be a result of the excitotoxicity that takes place during hangover/withdrawal, but I'm not sure if the same applies to water insoluble solvents like toluene.
 
That article on sevoflurane, I can't quite decide weather to think increased availability of sulfhydryl donors would be a good thing or not. Acetylcysteine sounds as though it might actually increase toxicity.
milk thistle probably wouldn't hurt, mind you. How about other relatives of sevo? halothane is of course, out, given the potential for metabolism to fluoride and accompanying toxicity.

Well alkanes in general, at least small, volatile ones that might be huffable (speaking purely on the ability to BE huffed, due to physical characteristics, I.e sufficient volatility to actually form a breathable vapor, rather than big, bulky things that are more like waxes than volatile gases or liquids, not of any intention I have to actually try them) and I'm sure as shit not about to go upstairs and grab me some toluene. Thats just...ew, regardless of toxicity or not.
Lower alkanes sensitize the myocardium to adrenaline release, so any sudden start, even relatively minor ones can trigger arrythmias.

Might just be doing some ether later though. (EtOEt/iPrOiPr mixture is ready on the lab shelves for something, although it turns out I do not now actually need it for the crystallization of what it was going to be used for, as the compound in question turned out looking pristine without its intervention (don't you just love it when projects turn out looking absolutely perfect after the first couple of rounds of crystallization....got myself some lovely looking, almost quartz-clear great big chunky crystals of my latest project being worked on after a long, long long slow multiple rextylization..almost too good to react further, rather than send 'em off to a gem cutter for mounting=D)

Not done ether via the inhalational route in a few years, only orally but just the smell of it always triggers memories of previous times on the stuff for some reason.
 
Mmmmmmmhhhmm, I love that smell! good job nobody else is at the house today for the entire place reeks of EtOEt/DIPE=D Unfortunately I had to redistil the stuff, so the smell has permeated through the entire house :p
 
Inhalational ether is one of those drugs where you think it'd be a gay old time, but then you somehow end up getting quite sick tasting ether on your breath and smelling it on your person for the next 12 hours. Yucky.

Please note that diisopropyl ether is a notorious peroxide former when in contact with air, especially when distilled it can leave explosive residues. Best to dispose of it by controlled incineration or store it on iron sulfate or something like that....
 
Its my fault for not saying so, I should have made it clear that I was NOT permitting the pot to boil dry. I don't do it with diethyl ether or THF, and I CERTAINLY do not do so when presiding over a roiling, bubbling still pot full of diisopropyl!! thats tantamount to blasphemy, and may if one is unfortunate, send one to much the same place:p

By 'getting quite sick' do you mean that in the context of becoming ill in the physiological sense sekio? or the psychic? (as in 'Mariae Iesu, lacrimosa mater, fuckin' well fed up of etherial belches') kind of getting sick. Sick of, rather than sickened by?
I daresay though, that actually I really quite like the smell and taste of it (either one, or both, I'd sooner drink diethyl ether though if I'm only going to be drinking one of them, the difference is not massive, but it does have its...well....different differences=D Most obvious to me is 'mouth-feel', DIPE feeling oilier...same...etherial-ness, but its like the oral equivalent of what it feels like if you rub your fingertips against each other after having gotten naphtha on your hands, more so than EtOEt does (and NO, I do not drink petroleum 'ether' or inhale it either, ever, save for catching the smel of it in the air, which is the closest I ever have, do, or will come to inhaling it...yuck what a thought! EtOEt on the other hand thats perfectly acceptable, quite tasty enough to be used in the mixing of drinks, if the right mixers and spirits, and in my own recipe, codeine cough syrup, theres one OTC, if hard to find these days, in tthe UK, thats scented, quite surprisingly enough, chloroform of all the shit one might find in cough mixtures. Quite surprised to find that. Its only in the one (called 'care +') brand of codeine linctus, but theres enough in it to oil out in a blob if a soft drink is added to it. Lime soda, cheap tesco own brand shit, is the best for it IMO, and it tastes really quite good, the chloroform gives it a very pleasant sweet, highly aromatic flavor and scent. I don't use chloroform, ever, as an intoxicant, but am content enough to like the taste when it happens to be there already
in the form of said codeine cough syrup. I only use my own chloroform however, for dissolving things or as a reactant. But its always been a favourite lab-smell, as has dichlor, but that lacks the sweet undertones present in CHCl3 and smells a a lot harsher, not unpleasant but doesn't smell like something that should be [is] appetizing to the palette, not that I've ever tasted any, deliberately or accidentally, don't plan to either:p)



(not a synth discussion intended there btw, I do not even actually have a product in mind. Was solely thinking in the most generic of terms, although the basic 'it' running through my noggin at the time was a hydride reduction of a substrate, although THF is more commonly used in many cases, as it forms a complex with E.g LAH', )
alternatively when the point is reached which breaks equilibration between the consumption of substrate/reagents and formation of unwanted byproducts via TLC monitoring])




But anyhow. If the ether ether has to begin with,or diisopropyl ether, THF and other ethers besides contain a low concentration of peroxide/hydroperoxides in it when you started work doing whatever is that one might use those different etherS) for, such as, if its not being ingested at the time, solvent purposes for syntheses, for extractions of products from sources within the realms of the natural world, as a quick'n'dirty cryogen in the case of dimethyl ether; and if the mildly peroxidized ethers are allowed to boil away, this of course, concentrates the solution of etherial hydroperoxides and peroxides to unacceptable levels, and potentially dangerous ones. The peroxides that form on oxidation are extraordinarily sensitive primary/contact explosives that need very little provocation before exploding. And considering that in general, the formation of fiendish, bastardly touchy contact HEs/unstable primaries is bad news, having it take place in a bottle of, or worse, a glass reaction vessel, and at that, one full of flammable solvents in the case of the bottles of ethers, where its got the chance to evaporate and peroxides form in screw-threads of container lids.

Doesn't take much working out what happens when some poor unlucky (and/or incautious/negligent/unaware) git is caught unawares and tries to open the crusty old bottle of ether thats been sat on the lab shelves some uni student years before the next person to come upon that particular old solvent. It turns from old forgotten surplus to requirements, crusty-arsed solvent, to a crusty old bottle of, no longer EtOEt or iPrOiPr but to Certifiablefucking-O-Nightmare and a nasty as hell job for some poor janitor who has to mop up the student and clean the bone fragments out of the lab sinks' plumbing when the drains get blocked later post pouring of student or other worker down there one too many times.

Else lets that now highly concentrated rxn vessels peroxide-rich solvent dregs then boils down enough for the operator to find out 'how much is too much' the hard way

I am well aware of the notoriety of DIPE due to its propensity for peroxide formation. One is meant to check it for peroxides rigorously, at least every three months, compared with diethyl ether, where one can get by with yearly, or so I have read. I tend to be pretty intentionally underconfident where ethers and their potential for leaving unwanted behind fare-well ''presents'', of the kind that go 'WhUMPPP!' in the night when one opens the giftwrap' and the giver of said little 'gifts' decides they have been slighted by not having been bothered to take notice of the giving, and treat it accordingly, having gone to all that effort to give one some shiny brand-spanking new peroxides AND hydroperoxides only to be ignored and left without so much as a peek at what's behind door number one*




(*Not impossibly what used to be doorframe, windows and part of the walls;))


Old bottles of even diethyl ether are best disposed of IMO, by taking them out into the middle of nowhere, with the greatest delicacy, putting the container down with the gentlest of kid-gloves, and taking a shot with a rifle. Or alternatively, building a
woodpile up around it, covering it in petrol or similar, white spirit, something dirt cheap and too crappy to use as a solvent, pouring a long trail of same, lighting the end and retiring to a good long distance away just in case the stuff IS peroxidized.
Never actually had one explode, but I either make or buy what I need, when I need it, and have around at most enough for a couple more reactions of whatever kind so as to have used it all up before it ends up being a caged devil straining to get out
and rip my face off :p I have read a few horror-stories about old crusty ass bottles of THF and EtOEt that actually did explode, and seen a picture once of ground zero where one went off, and the devastation left behind...jesus H. Uni or some other professionally-funded and owned lab, and just as well because someone's home lab is unlikely to be insured, and assuming no terrible injuries in such a setting, that would be devastating in more than simply the sense of physical damage, but also in the sense of losing thousands of pounds worth of one's most treasured possessions.

When I DO need to strip ether, I make sure to test it for peroxides right the very moment before it is due to be gotten rid of, and if present, treat for same. And also, I add a bit of a higher-boiling solvent such as an alkane, which the ether can then be removed from and the product isolated by means of freeze precipitation, HCl gassing, etc. etc.

I've a question actually sekio, is it safe to let dimethyl ether boil off to dryness? because its stored in pressurized vessels, and it is so volatile as to have a sub-zero centigrade BP, volatile as butane or similar in practice at any rate, and dissappears before one's eyes. I use it sometimes for cooling reactions down, in freezing mixtures, and it works pretty well by all accounts. Is it at all likely to peroxidize so quickly in such a setting as to make its evaporation dangerous?

And also, whilst I know its meant to be pretty prone to peroxidation, how often should one test THF?
 
On the topic of peroxides, the saving grace of modern chemical suppliers is that they will supply solvents like diethyl ether with at least a few ppm of stabiliser (BHT in the case of diethyl ether) which acts to help prevent peroxide formation for a while (hence the need to check & restabilise or dispose of it after ~12 months of storage). So, ethers forming peroxides in this day and age usually only occurs if you store freshly distilled stuff.

THF can form peroxides just like diethyl ether. Technically, so can isopropanol, though... :p It's my understanding that water helps prevent peroxide formation to a degree, but I wouldn't rely on it.
More info - http://www.ehs.uconn.edu/Chemical/Peroxide-FormingCompounds-FactSheet.pdf

And also, whilst I know its meant to be pretty prone to peroxidation, how often should one test THF?
Once every 6 months?

I've a question actually sekio, is it safe to let dimethyl ether boil off to dryness?

Should be. Just be sure to do so somewhere away from any source of spark/ignition and in good ventilation. On paper you could displace a portion of the oxygen in a room if you released enough dimethyl ether quickly enough.
Doing it indoors is sort of asking to turn a whole room into a fuel-air explosive and should be strongly advised against....

Dimethyl ether doesn't form peroxides like diethyl ether[ref]: the radical species that is the precursor for the hydroperoxide is effectively a primary radical (terminal CH3 on an alkyl chain) which is one of the hardest-to-form and least favorable species. (as compared to the secondary alpha-hydrogen positions on diethyl ether or the tertiary alpha-hydrogen positions on DIPE).

---

If we're talking solvent smells, the only solvents I find tolerable for long periods of time are diethyl ether, ethyl acetate and the lower alcohols.
Having to breathe larger quantities of diethyl ether vapors makes me physically want to gag and stimulates nausea/vomiting. Same with DCM or chloroform.

Benzene smells very acrid and sharp to me, whereas chloroform and dichloromethane a sickly characteristic odor - i don't characterize it as either pleasant or sweet. Chloroform is more tolerable than DCM, but I still would not call it "sweet" at all.
Iodopentane smells like swimming pool chemicals. Prenyl alcohol smells like a really cheap felt marker pen.
Hexanes/pet-ether smells pretty "mild", but I do my best to not breathe too much of that stuff (genetic damage via its metabolic product 2,5, hexanedione)
Toluene smells nice and aromatic, but gives me a headache when there's more than a trace. Xylene reminds me of ourdoor pool deck sealant, and smells distinct from toluene.
Dimethylformamide is slightly "fishy". DMSO is pretty mild unless you get some on you, or really heat it in a reaction ..
Acetic acid and acetic anhydride.... those get a fume hood, 'nuff said. :)
 
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Yeah I have actually read about IPA exploding. I cannot say I worry too much about it though, its not really what one could call an infamous source of destructive potential.
Funny EtOEt does that to you, personally I love the smell/taste of the stuff. DMF is usually only fishy if it contains traces of the corresponding amines afaik.


As for inhibitors in ether, yes, true, but it depends where you get them from. The supplier I use for most everything supplies her ether/THF etc uninhibited. I'd prefer it a lot if it were supplied w/ inhibitor.
DMSO I've little experience with really, its such a high boiling solvent that I avoid it whenever humanly possible, because one then has to bugger about going to all that effort to strip it off afterwards.
By swimming pool chemicals I presume you mean hypochlorite or similar? funnily enough, NaOCl has to be one of the foulest things I ever work with in terms of how I find the stink of it. Its gutwrenching, makes my insides do backflips just thinkng about it, without ever being anywhere near any, the thought goes right through me, like wool, or the texture of wooden ice lolly sticks *shudder*..ew!
Your definitely not wrong about AcOH and Ac2O. Tolene is..tolerable, neither really pleasant nor really unpleasant. Xylene I think smells alright, quite pleasant in fact..possibly because of all the paint thinners in the workshop my old man used to have before he had to give up work because of my mothers disabilities.

IPA and EtOAc..how can you possibly find those pleasant...jesus H! hate the smell of IPA especially, ethyl acetate I just don't much like. Reminds me a bit of tolly or slightly less so, of xylene. IPA though is gag-worthy in much the same way you find ether. I take it you'd not be accepting an invitation to an ether-drinking pissup then:p

Tell you one I really can't stand though, and thats propionyl chloride. Nasty stale musty sweaty kind of smell to it. The HCl fumes are by the way really, I figure its probably propionic acid from hydrolysis. For some reason it reminds me of a petting zoo, one with goats, if goats went stale if not used quickly enough=D and if said goats past their sell-by-dates had instead of hooves, feet on which to place socks, which they could then forgo washing for a month or so of playing foot/hoof-ball. Why, I don't quite know, well the feet bit yes, propionibacteria are responsible for staleness in sweat, at least partly, and cheesy rancid feet.


Not that I go huffing them (well not apart from diethyl and diisopropyl ethers) for the purpose of intoxication, but just in the sense of generally having detected them by the means of their odors, favourites by far (so far) have to be EtOEt/DIPE, chloroform, xylene and acetonitrile. And especially nitromethane, nitroethane, benzaldehyde (without ring substitution that is, just plain bog-fucking-standard benzaldehyde). A knoevanagel where the aldehyde is benzaldehyde smells almost good enough to drink (not recommended however. And even less so given that LC's typical solvent for the knoevanagel is MeOH=D IPA is good for it, but that fucking stinks like shit floating down the river Styx [not OF shit, like shit, big difference]) thats two of his favourite of all smells in the lab, in the same pot (the nitroalkane du jour, and benzaldehyde)

I'm not sure quite what the product was, back then I wasn't equipped to characterize is thoroughly enough to make an accurate determination, other than some basic tests, like trying to form oximes, bisulfite adducts etc), but once, many years ago when I was just a bit down the way of my chosen paths, hobbies-wise*, but what at the time I'd been trying to do, was to synthesize some TNT, only to find I'd run out of conc. HNO3 to do the usual mixed acid route to it, so naturally an alternative was sought, and what was done, was to try an in-situ nitration using conc. sulfuric, which I had plenty of left to try with, and ammonium nitrate. Tried it at room temperature, intending to go with a long rxn time. Didn't get what I was after, but rather
a mixture of something crystalline, which may have been, but was IMO, far more likely one or more isomers of mono/dinitrotoluene, in which, due to the other product, I quickly lost interest in. A yellowish, oily-looking liquid that smelled like benzaldehyde crawled up the arse hole of a huge, industrial sized block of marzipan, dressed in not fig leaves, but a suit of cherry laurel leaves for 'modesty's sake, and died, going to marzipan factory hell. Even on a relatively small scale (a drinking cup measure of toluene, not that the nitration was done in a coffee mug haha, no, it was only used for something to pour the tolly into so as to get a good idea of scale and not use more than I wanted, at that age, EVERY last scrap of ALL my reagents, including solvents, and even most reaction byproducts was saved, cleaned, redistilled for solvents, and rxn byproducts saves, separated if needs be and kept until I could find another use for them, because I'd only JUST even gotten a bank account with a card and checkbook, and my funds were way too limited for my liking so meticulous pennypinching, scrimping and saving were the order of the day; NaCl was about the only thing I didn't bother recycling. Lol before I realized how little was there to be had, I even tried isolating the pyridine from methylated spirits, and I'd save KCl, KOH, NaOH even, ammonium salts I'd recycle the NH3 from those, hack the lead oxides/sulfate out of car batteries, until I both had enough for my uses,
and I realized that those same car batteries could be turned into what was to me back in those days, a lot of money by trading them in at the scrap yard, not that the money usually ever even made it home, instead going straight to the hardware stores and automotive stores for ether, chlorates, ethylene glycol, NaOH, ammonium sulfate, HCl and conc. sulfuric. The furthest it ever usually got was to the pharmacies within walking distance for acetone, permanganate, epsom salts, clean bicarb, iodine tincture and other such things to keep my insatiable childhood curiosity occupied [now no different other than the sources of, the scale, quality and types of reagents, and insatiable adult curiosity. I'm absolutely not so much as an attosecond changed, save for being more learned and a lot better at it than I was then=D Nor do I ever entertain the possibility of my being, or doing otherwise. Only in my worst possible, or damned close to it, nightmares.

I didn't know at the time, as I'd no internet connection, not sure there even WAS an internet at the time, if there was then it was certainly in its very primitive stages...my computer ran MS-DOS at the time, and somewhat later on, windows 3.1:p not that I've many bad things to say about DOS, I still use DOSbox quite a lot, although far prefer the real thing. So textbooks were my teachers, my first Kanner's school didn't have a proper science teacher, the only specialist teacher in the whole school
was for IT, and even he taught me nothing I did not already know. And the only chemistry class during my entire time at that school, was watching someone drop iodine tincture on a potato. Once. From as far away as they could get it...never letting
the students anywhere near either the iodine, or even the fucking potato! Which is quite likely what spurred me on to spend all the money I had on as many bottles of iodine tincture, some peroxide and some sulfuric acid the moment I got home, and spending from the time I returned home from rounding up my purchases, to the very moment I had to step out of the front door of the house to the waiting minibus to take me to 'school' again, and carefully fractionating off the other ingredients until I'd managed, to my delight, to see/own some I2 in the elemental state for the very first time, not bought, but prepared by my own two hands, which is what mattered the most to me at that age, not simply the acquisition; but rather the having learned from it in the process because I'd done it. Unfortunately, I'd not realized how volatile it is, so you can imagine how PISSED and upset I was after getting home from school the next day, having been on the edge of my seat all day, itching to get home and try the next thing on my to-do list, MeI starting from scratch, only to find what I'd worked all my free time the previous day, and into the night without a break and without sleeping, and finding it gone. Or rather, relocated, to stain the everfucking bejeeszis out of one of my reagent cabinets, not to mention part of my bedroom wall. Although that was of secondary, minor irritation compared to discoloring the reagent cupboard:p

Anyhow at the time, I wasn't at all familiar with its physical properties, but now, I suspect that the yellow oily liquid from my failed attempt at in-situ production of TNT, had been in actual fact, nitrobenzene, and the crystalline solids para-nitrotoluene and/or 2,4-dinitrotoluene. The liquids I guess could have been one or a mixture more likely of the ortho- and meta- isomeric nitrotoluenes, but those are meant to have a weak smell, although nevertheless of bitter almonds. Or perhaps oxidation of some of the toluene occurred and produced benzaldehyde itself. Never actually smelled pure redistilled nitrobenzene, as its toxic as buggery and something only handled whilst wearing a gas mask. Bar, if it was indeed one of the unintended products of that attempt at nitrating tolly using a nitrate salt instead of HNO3. Faint, it was not, though, even a very small quantity left out in the open, was sufficient to fill the entire room with the most overpowering, although quite delicious scent of marzipan or benz. One of these days I'll have to have another go at it, not aiming for TNT, already found out that didn't work, but so I can actually thoroughly characterize whatever the devil the mixture of compounds that do result contains.



*(mycology excluded, as I got an extremely, extremely early head start there thanks to, for some reason there being textbooks available for my perusal and use in teaching myself to read [3yo, according to my old man, was when I was gotten a copy of Phillips' after exhausting everything in the others, and finding ones with drawings etc. completely unsatifactory. I was really chuffed, that much I DO remember even at that age, because it has plenty of details on the microscopy, and I was allowed, as long as I was careful with it, to use my dad's old microscope. And when I say old, I mean 'big, chunky, heavy-as-all-hell article, formed out of solid brass or bronze. Its still
around somewhere AFAIK although I haven't used it in decades, especially as I now have a very nice new one I bought myself as a treat when I had a couple of hundred quid I could afford to spend on something other than the essentials in life. And by that I mean the kind of essentials that one puts in one's mouth in order to supply the rest of the attached meat with sufficient protein, carbohydrate and fat to keep it able to make use of the kind of essentials-in-life that one generally puts in RBFs and other flasks, test tubes etc. and shiny new condensers, Kipp gas generators, sep funnels, Sohxhlets [granted one can make do without a soxhlet, but it was nice to get one all the same]still flasks, dessicators [albeit my dessicator was a gift from my old man, as was my autoclave and my vacuum pump. Hes not a chemist, not at all, but he knows his son, and he knows the kind of things that he likes to receive most, if a gift is to be given..he knows how to please, that he does, if he decides to do so then he usually hits the bullseye. My b/day opportunity has gone this year, but methinks for xmas I'm going to be angling for a cryostat..either that or a sonoacoustic laser,although I'd rather try and build the latter, the cryostat on the other hand
is something I've been wanting for AGES] and other such non-consumable, reusable essentials)

Least favourite/worst are IPA, ethyl acetate, GAA (if that counts), MEK and worse, MiBK. Minty but somehow awful at the same time.

I can't imagine using Ac2O without proper ventilation, at least not without a good mask with acid gas filters. Even GAA isn't great, especially if its being strongly heated. Leaves the area stinking like the aftermath of an airstrike on a chipshop=D
 
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