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The Higher States of Bromine
- perl4ever 7y agoI've wondered if I should be nervous about brominated vegetable oil in food. I mean, it's not new or unusual, but I feel like if it was just invented, we'd all be rather skeptical, no?
- sansnomme 7y agoYou know, philanthropists really need to invest in higher level free education for non-CS sciences. We have tons of free resources with tremendously beautiful animations on data structures and state-of-the-art machine learning, but the same can't be said for bio and chemistry. This is holding back the biotech industry. People can't make educated judgements about stuff like Mercury Thiomersal because that level of organic chemistry understanding isn't covered well by existing resources like Khan Academy. Hacker News and Silicon Valley loves disruption and "Move fast break things" Uber-style. How about democratising medical education? The cheapest, fastest way to improve healthcare in developing countries is to break the whole "apprenticeship" gatekeeping system that plague medicine and pharmacy. There is no FDA in Africa to bring down the hammer on you making videos on low-cost quality control for orphan drug analogues when people are dying due to corruption, incompetence, and poor medical practices. The level of biochemistry knowledge on HN is amazingly poor, every thread on CRISPR and gene drives reads like the infamous parable of the blind men and an elephant.
- harimau777 7y agoI would love that! I'm researching materials for a project I'm working on so I've been reading a lot of chemistry articles on Wikipedia. I've noticed that there appears to be a set of known building blocks that chemists use to build solutions. Something like: - "Molecule bits" (rings, chains, functional groups, esters, etc.) that have known properties - Common processes for modifying/changing those bits (alkylation, calcination, ether cleavage, etc.) - A set of standard chemicals (alcohols, acids, solvents, emulsifiers, etc.) For example I often read things like: "In order to give a polymer higher temperature tolerance, chemists often add a benzine ring by calcinating the molecule using acetone."[1] While I'm sure that a professional chemist needs to be able to handle lots of edge cases, it seems to me that a lay person could get a lot of milage out of learning these standard building blocks. I'm going to have to look and see if I can find a good resource that explains them. [1] Note: All of this sentence is completely made up, I just intend it as an example.
- whatshisface 7y agoThat "good resource that explains them" would probably be an organic chemistry textbook.
- shagie 7y agoChasing links from the article's author... the category pharma 101: https://blogs.sciencemag.org/pipeline/archives/category/pharma-101 https://blogs.sciencemag.org/pipeline/archives/category/phar... https://blogs.sciencemag.org/pipeline/archives/2014/09/22/a_free_online_medchem_course https://blogs.sciencemag.org/pipeline/archives/2014/09/22/a_... - A Free Online Med-Chem Course The course appears to now be at https://www.coursera.org/learn/drug-discovery https://www.coursera.org/learn/drug-discovery
- perl4ever 7y agoIs thimerosal or biotech connected to the post you are responding to in some way?
- pbhjpbhj 7y ago>People can't make educated judgements about stuff like Mercury Thiomersal because [...] // Removing Thiomersal from vaccines didn't reduce ASD diagnoses. That seemed to be sufficient for me to form a judgement on it. But, AIUI it's not used in vaccines in the UK now anyway.
- longemen3000 7y agoYeah, the bromine ion has half life in the body of some weeks, and can cause some neurologic problems,but the body eventually expels it away. I would be worried, but is, not in my primary list of food risk
- pfdietz 7y agoBromine is now on the list of essential elements. It's necessary for proper synthesis of weird S=N bonds in collagen IV. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4144415/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4144415/
- longemen3000 7y agonice to know! well, so it enters in the same category of a lot of elements, good in small quantities, can kill you if you eat it too much.
- isoprophlex 7y agoMind you, there is no ionic bromine in brominated vegetable oil. There are carbon-bromine bonds in there, so it's toxicity is also dependent upon what your body does to those. Bromo alkanes are known alkylating agents. Some alkylating agents are carcinogenic. YMMV... https://en.m.wikipedia.org/wiki/Brominated_vegetable_oil https://en.m.wikipedia.org/wiki/Brominated_vegetable_oil
- baldeagle 7y agoBrominated veg oil is the thing that gives mountain dew the unique mouth feel, and sometimes light oil slick appearance once stale.
- big_chungus 7y agoWould you please elaborate on the "unique mouth feel" of mountain dew, for someone who hasn't had it?
- taurath 7y agoIt has a slight "coating" effect, when compared to a normal effervescing carbonated beverage.
- saagarjha 7y agoWell, the oil slick is the brominated oil not doing its job…
- perl4ever 7y agoIs it really not in anything else? Seems like I have seen it in the ingredients for other things.
- twic 7y agoWell, it's banned in the European Union, so you could always move over the Atlantic and not have to worry about it. On the other hand, as a UK resident, i look forward to finally getting to try it next year!
- johnhess 7y ago"Things I wont work with" is a great concept that tech should borrow from chemistry. Some things, while they carry possible returns on investment, are simply not worth the risk. I wonder what "Things I wont work with" would be for tech. I can imagine particular technologies (e.g. predictive policing) or types of data (e.g. I refuse to put digitized therapist's notes on the internet).
- jeanlucas 7y agoI try to apply this to my own work, nowadays I work with financial software in South America, and I have the power to suggest what to use and what to avoid. I decided, and yet to know if it's a good idea or not, to instead of worrying about leaking data, not collect some types of data at all.
- rsynnott 7y ago> to instead of worrying about leaking data, not collect some types of data at all. Interestingly, this has probably been the main beneficial effect of the GDPR so far. Personal data has shifted from being a pure asset to a combo of asset and liability, causing some companies to just avoid collecting anything but the essentials.
- Jestar342 7y ago> I refuse to put digitized therapist's notes on the internet There is just no way that doesn't already happen all over the place already. The "things I won't work with" blog lists things that will actually kill you in horrible, mind bendingly painful ways. In Tech it's more like "things I won't work with because it might fail" or "is too difficult" or "might be a bit too unscrupulous"
- paranoidrobot 7y ago> In Tech it's more like "things I won't work with because it might fail" or "is too difficult" or "might be a bit too unscrupulous" For some of things, sure. But there are other things that do cause death, pain and suffering. If you wrote code that's used in military weapons, that's a more direct relationship. If you write code that's used to power gambling sites/devices, it's perhaps somewhat abstract - but there are a large number of people who are harmed because of how addictive these things are. If you write code that's used for managing high-interest loans (like the point-of-sales type of 'buy-now-pay-later' of loans) - then you're enabling the exploitation of people who by-and-large cannot afford the things they're being told they can have, and will spend a large portion of their life paying these loans off.
- OliverJones 7y agoI started out a biochemist before I discovered computers. This article is rofl funny. "invigorate itself all over the ceiling..." yeah, got the t-shirt. That's why they took away my bunsen burner and gave me a mouse. Seriously.... fellow programmers, designers, entrepreneurs. What are the things you won't work with? For my part: Web code written in any language without a well-integrated string data type. strcpy() is a target painted on my back if I did that. Anybody who claims they've got amazing new data- or media= compression technology and wants funding for it. Transferring peoples' data from a protected realm (like a HIPAA-covered pharmacy system) to an unprotected realm (like direct marketing).
- sansnomme 7y agoTo be fair, neural networks are very effective for (lossy) VR compression/representation. See: papers by Facebook Research.
- ben_w 7y ago> Anybody who claims they've got amazing new data- or media= compression technology and wants funding for it. Anyone whose business plan names an existing famous company — “Uber for aircraft”, “Facebook for political activists”, that sort of thing.
- Niksko 7y agoWhy? These sorts of descriptions are incredibly useful for getting people to understand your value proposition. Just because you mention this doesn't mean you're going to adopt Uber or Facebook's moral code.
- lightedman 7y agoWhat's more accurate, saying "Delivery for X" or "Uber for X"? In almost every spiel I've heard as an "Uber for X" it has been a delivery service. The usage of a pre-existing company name is meant to mislead people into using their service. This has been a common practice for a long time, which is one of the myriad reasons why we have things like trademark laws to curb such language in advertising (in which a sales pitch counts as such.) I've been guilty of the same thing roughly 15 years ago. Once I realized the wrong I was actually committing, I stopped. I've got a strong sense of justice/fairness, and the usage of another company's name to hawk your similar yet wholly unrelated service rang wrong with me once I understood the history behind the laws.
- samatman 7y agoThis entire series is a treasure. I'll share my favorite, just for the phrase "Satan's kimchi" alone: https://blogs.sciencemag.org/pipeline/archives/2010/02/23/things_i_wont_work_with_dioxygen_difluoride https://blogs.sciencemag.org/pipeline/archives/2010/02/23/th...
- ce4 7y agoThe articles from that series have been discussed a couple times here already, it used to be hosted somewhere else. Nice to still see them (the first search's original links are dead though, available under the new domain): https://hn.algolia.com/?&query=pipeline.corante.com%2Farchives&type=story https://hn.algolia.com/?&query=pipeline.corante.com%2Farchiv... https://hn.algolia.com/?query=http%3A%2F%2Fblogs.sciencemag.org%2Fpipeline%2Farchives&type=story https://hn.algolia.com/?query=http%3A%2F%2Fblogs.sciencemag....
- HeWhoLurksLate 7y agoI can't even figure out what to say about that. That was worth the read. Thanks!
- rpeden 7y ago"Sand won't save you this time" is another great read from the series: https://blogs.sciencemag.org/pipeline/archives/2008/02/26/sand_wont_save_you_this_time https://blogs.sciencemag.org/pipeline/archives/2008/02/26/sa...
- Nextgrid 7y agoAnother gem I highly recommend reading is his post on selenophenol: https://blogs.sciencemag.org/pipeline/archives/2012/05/15/things_i_wont_work_with_selenophenol https://blogs.sciencemag.org/pipeline/archives/2012/05/15/th... > The biggest stinker I have run across. . .Imagine 6 skunks wrapped in rubber innertubes and the whole thing is set ablaze. That might approach the metaphysical stench of this material.
- api 7y agoA long time ago I found this series and LOL'ed and then had to email him a link I found to an experiment in using fluorine instead of oxygen in a rocket as an oxidizer. It resulted in the highest specific impulse ever recorded for a chemical fuel and would be awesome were it not for the exhaust being pure hydrofluoric acid.
- prox 7y agoYou mean “launch the rocket,everyone dies” awesome?
- pfdietz 7y agoI believe the highest Isp with fluorine is Li/H2/F2 tripropellant, in which the exhaust is mostly hydrogen and lithium fluoride.
- api 7y agoWell I guess if you need a flame thrower in hell...
- carapace 7y agoDr. Peter Plichta figured out how to make silane fuel, basically replacing carbon with silicon. > Before the 1970s, silanes were considered unsuitable for use as fuels, because they instantaneously self-combust at room temperature. Not satisfied to leave it at that however, Plichta went to work and succeeded in producing longer-chained silanes that appeared as clear, oily liquids and were stable at room temperature. ~ https://www.offgridquest.com/energy/turning-sand-into-fuel-silicon-oil-as-an https://www.offgridquest.com/energy/turning-sand-into-fuel-s... It burns nitrogen and the reaction is so energetic the flames are lighting. https://www.plichta.de/plichta/ https://www.plichta.de/plichta/ http://www.rexresearch.com/plichtasilane/plichta.html http://www.rexresearch.com/plichtasilane/plichta.html
- userbinator 7y agoThe related linked article at https://blogs.sciencemag.org/pipeline/archives/2005/12/17/how_not_to_do_it_bromine https://blogs.sciencemag.org/pipeline/archives/2005/12/17/ho... is also well worth reading.
- tectonic 7y agoThey're all amazing. Here are past issues: https://blogs.sciencemag.org/pipeline/?s=things+I+won%27t+work+with https://blogs.sciencemag.org/pipeline/?s=things+I+won%27t+wo...
- shoghicp 7y agoBetter link pointing to the category, includes more results https://blogs.sciencemag.org/pipeline/archives/category/things-i-wont-work-with https://blogs.sciencemag.org/pipeline/archives/category/thin...
- phkahler 7y agoFrom the comments: At least in the States you can have potassium bromate added to the flour in your bread. They say bromine stands in for iodine, which is critical for many things.
- annoyingnoob 7y agoHigher States of Management. I'm like a cat, feed me and let me do my own thing and I will keep bringing you dead bugs. I promise to crap only in the sandbox.
- m0zg 7y agoReminds me of "Ignition!", which is, if nothing else, a very entertaining read. Those dudes out of necessity had to work with every dangerous and explosive chemical known (and discovered a few in the process). At one point in order to boost the thrust of engine they _sprayed liquid mercury_ into the nozzle. Unsuccessful tests often meant that the building housing the rocket motor would be demolished by explosion, often simply because some chemical ran the wrong way in the tubing due to pressure differential or some newly discovered rocket fuel or oxidizer had a reaction with some minuscule contamination in the fuel or oxidizer line. There were also some proposed fuels (butyl mercaptan) that smelled so foul, they had to evacuate buildings, but that did not stop them from experimenting with them in a wooden shack 200 yards away from the main building.
- pfdietz 7y agoThey didn't spray mercury into the nozzle; it was injected into the thrust chamber itself with the fuel and oxidizer. The point was to maximize "density impulse" (specific impulse x density of propellants). Using zinc would have been much less dangerous.
- wnkrshm 7y agoMy favorite story is the lemon oil (limonene) test - they did an engine test with it because of political pressure and according to the author, the desert smelled like lemon for 2 months after that.
- twic 7y agoThere's a link in the comments to some nutter who does mildly horrifying syntheses on YouTube, like this one for chromyl chloride: https://www.youtube.com/watch?v=saANxD0cqy0 https://www.youtube.com/watch?v=saANxD0cqy0
- girvo 7y agoNileRed is great fun to watch - but his clean up processes are sometimes a bit horrifying to watch knowing he’s doing it alone and at home with a semi-stocked amateur lab haha
- sq_ 7y agoWow. I just watched that one and his toilet paper moonshine video. I can’t believe he’s doing all of this in a home lab!
- emikulic 7y agoThese days he rents a commercial space. He's done videos on setting it up. It's NurdRage that lost his lab and is doing stuff in his bathroom again.
- zdkl 7y agoSpeaking of horrifying home chemistry, Australia is well represented with Explosions&Fire/Extractions&Ire https://www.youtube.com/channel/UCVovvq34gd0ps5cVYNZrc7A/videos https://www.youtube.com/channel/UCVovvq34gd0ps5cVYNZrc7A/vid...
- ComputerGuru 7y ago@dang and co: The old title with “things I won’t work with:” is both the name of a series HN is familiar with and presenting in TFA as the category the post was made under; perhaps it should be returned?
- dang 7y agoWe tend to remove names of series, as well as names of sites and other repetitive markers from titles, in the interest of keeping things unpredictable. An unpredictable HN is a good HN. The fact that this is a "Thing I Won't Work With" instalment shows up immediately in both the article and the comments, so the information is only one hop away. Also, the article being at #1 is a strong clue that the content is interesting to more than just chemistry specialists. It's generally good for HN if not everything reveals its secrets right away, and readers have to work a little (https://hn.algolia.com/?dateRange=all&page=0&prefix=false&query=by%3Adang%20%22work%20a%20little%22&sort=byDate&type=comment https://hn.algolia.com/?dateRange=all&page=0&prefix=false&qu...). When you have to do a tiny bit of work before getting the dopamine hit of pattern-matching, it seems to put the brain in a slightly less predictable state. Before we changed the title, the thread was mostly about the series, not the specific article. That's poorer for discussion quality, which gets more predictable and less varied as topics get more generic. (For lots of explanation of that phenomenon, see https://hn.algolia.com/?dateRange=all&page=0&prefix=false&query=by%3Adang%20generic%20discussion&sort=byDate&type=comment https://hn.algolia.com/?dateRange=all&page=0&prefix=false&qu... and https://hn.algolia.com/?dateRange=all&page=0&prefix=true&query=by%3Adang%20lists%20common&sort=byDate&type=comment https://hn.algolia.com/?dateRange=all&page=0&prefix=true&que...) If anyone wants to read (a lot) more about title changes on HN, some recent things are https://news.ycombinator.com/item?id=21617954 https://news.ycombinator.com/item?id=21617954 and https://news.ycombinator.com/item?id=20429573 https://news.ycombinator.com/item?id=20429573.
- ComputerGuru 7y agoThank you for the explanation -which you did not have to provide. I have learned something new today! Thank you to you, Scott, and everyone else for keeping this site so wonderfully curated.
- nitrogen 7y agoI noticed that all of these reactions are performed at very low temperatures. Could there be enough chemistry for life at these very low temperatures?
- dnautics 7y agoI do think derek lowe is a bit too paranoid about HF. I've worked with HF before, and with a proper setup (negative pressure, calcium carbonate filter, teflon equiment) it is really quite reasonable to handle. I would entrust a conscientious first year grad student to it (as I was entrusted). I only screwed up once [1], and the consequence was we lost about 1/8 of our calcium carbonate filter column. You can tell because the section that has most recently been expended is warm on the outside of heavily shielded carbonate vessel). [1] the screw up was I had left the HF open (but not pulling) for 20 minutes instead of 5.
- omar_a1 7y agoI think you're not paranoid enough about HF. It doesn't wash off, and is small enough to pass through skin to form insoluble mineral precipitate with calcium in bone and blood, which can result in amputations from dead tissue. It's one of the few acids capable of eating through silicates in glass or rock. Even at lower concentrations, you still need specialized gloves, apron, and ideally a face shield, in addition to standard PPE. Source: worked with HF for 3 years.
- refurb 7y agoAgreed. If I had to choose splashing my arm with a concentrated acid, I would choose sulfuric or nitric acid over HF. Unlike the other acids that just burn the surface of the skin, HF rapidly penetrated the skin and can mess up your potassium levels. Plus tissue destruction is much deeper.
- dnautics 7y agoThat's why you keep calcium carbonate salve around. Also you're more vigilant around hf. I've spilled conc sulfuric and nitric acid on my lab coats. HF will never get that close, as safe equipment is in a closed loop but not that complex or byrdensome (it's not like explosives research for example) There are some idiots that use open air HF for etching. That is a very bad idea. I should clarify by open in the description I meant valve open. The system was still closed.
- jdnier 7y agoHere's the full list of "Things I Won't Work With" articles: https://blogs.sciencemag.org/pipeline/archives/category/things-i-wont-work-with https://blogs.sciencemag.org/pipeline/archives/category/thin...
- sandworm101 7y ago>> ...a willingness to do things like redistill anhydrous HF, and you will at all times want to be suited up like you’re going to going to spay a velociraptor. Best chemistry-related description since the one in Ignition about running shoes as vital lab equipment.
- fuzzfactor 7y agoKeep in mind the risk with just regular liquid elemental bromine. Seems like a heavy red nasty fuming liquid because it is. Concentrated nitric acid is heavy too, has aggressive red fumes of its own kind but it is a clear liquid. And you can pipet nitric acid. But you can't pipet bromine. If you try it, you might think so at first since bromine can be drawn up in to the pipet like any other liquid, but once you remove the pipet from the source bottle, it expells itself from the pipet before any transfer can be made. With nature at work, it begins destroying anything it had come in contact with, while the majority of the carefully measured quantity rapidly evaporates and instantly triggers the evacuation instinct with great encouragement. Even when handled under a fume hood, where most of it goes up the hood, people at the other end of the lab will be out the door in less than one second after the first whiff. Don't ask me how I know but there was this graduate student who was a little bit of a loose cannon . . .
- isoprophlex 7y agoThanks for reminding me of this undergrad student who tried to recover the product of a bromination... By sticking the reaction mixture, bromine and all, on a rotavap. Outside a fumehood.
- dschuler 7y agoHow do you move it around if you can't use a pipette? Or if you say "well, you can't", do you know how the manufacturer gets it in the bottle?
- saagarjha 7y agoSome precise pouring, maybe?
- fuzzfactor 7y agoThings like this you try not to spill a drop. Sometimes more is spilled, take a look at this, where a noticeable release in Shandong was being filmed from a _safe_ distance when it got worse fast and filming continued whilst fleeing. Footage was then stabilized by a reddit viewer: https://gfycat.com/aggravatingagileherring https://gfycat.com/aggravatingagileherring >Xinhua News Agency, Jinan, May 9 (Reporter Zhang Zhilong) The reporter learned from relevant departments of Shouguang City, Shandong Province that at around 14:00 on May 9, the bromine tank of Shouguang Yumeng Chemical Co., Ltd. was tilted, and part of the bromine leaked. Short-term red smoke band. No casualties. > After the accident, Shouguang City safety supervision, environmental protection and other departments immediately rushed to the scene to assess the disposal. At present, the site has been disposed of and the cause of the accident is under investigation. > It is understood that chemical bromine is a red-brown fuming liquid that has strong irritating and corrosive effects on the skin and mucous membranes. Google translation of source http://www.xinhuanet.com/2018-05/09/c_1122808340.htm http://www.xinhuanet.com/2018-05/09/c_1122808340.htm Glad only a small part of it overflowed, wouldn't want a significant incident. What you see here is just the spill, not a result of chemical reaction or other runaway condition.
- nullc 7y agoIf you enjoy reading about crazy chemistry, I recommend the book "excuse me sir, would you like to buy a kilo of isopropyl bromide?" a 70's era autobiography by a chemist. https://archive.org/details/gergel_isopropyl_bromide https://archive.org/details/gergel_isopropyl_bromide
- dekhn 7y agoI still clearly remember using bromine in high school chemistry lab... horrible fumes. "Do not pipette by mouth".
- lostmyoldone 7y agoMy high school teacher in chemistry was a bit of an original. Dedicated and ambitious, and maybe a little bit crazy. In our 2nd and 3rd year we did quite 'serious' organic synthesis labs, including bromination of benzene, which of course included elemental bromine. The teacher did ration it out in out small stoppered round bottom flasks, but then we all did the synthesis in teams of two/three. He was still very serious on security, and I guess his main reason for including that lab was to make sure that all his students had understood the seriousness of chemical dangers. If you had done anything even slightly out of line in any lab, but especially that one, you would absolutely have been sent home, and probably been advised that maybe experimental organic chemistry wasn't for you. Right or wrong, but that's the story about how I got to work with elemental bromine in high school at the age of 16 or 17.
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- fuzzfactor 7y agoIt can be an interesting head start at a young age. I went to experimental school having more progressive and well equipped labs than supposedly others at the time. Everything was new and advanced, we were the guinea pigs. Not toxically by any intention, just behaviorally for the most part. I got to the university early and had excellent professors, ended up interning when I was 20 at a leading research fluorochemical and silicochemical plant that had been a startup from one of them years earlier. By the time I got there they had a fluorine trailer on site, at times the only live one in North America back then, so "no insurance for you". We stocked experimental silanes, silazanes, fluoromonomers, and things like fluorides of xenon in the main chemical room if they were under a few kilos. Osmium tetroxide too, but only a few grams. But there was another building with the real nasty stuff on the shelves, where every single one of them was something most chemists would never want to see the bottle open. Especially if they were the poor soul that had to do it the previous time. Too bad a lot of the compounds would eat through the bottle cap within a faily predictable period of months or years according to the material, so somebody was going in there fairly regularly to accomplish cap replacement as needed anyway. You could tell when something was coming out more agressively than normal when you walked by the building. It was easy to smell since it was built with the cinder blocks turned sideways for ventilation, just like the numerous systhesis labs scattered safe distances from each other, all far from the heavy concrete blast embankment which faced off into the woods. Only the labs didn't have actual doors in their four doorways. It didn't go without saying that 4 ways out still might not be enough for a single chemist, and you can't have any obstacles in your way. Firefighting training included extinguishment through the flow-through walls into the dummy lab from the outside, which was just a lab that had gone out of control but not been completely destroyed. The agressive chemical storage had secure doors but it was still gagging you with its smell-through open walls. How much worse could it get to actually go inside? Well there was the thiophosgene. You think plain phosgene is bad, this is not your everyday phosgene. It was rough, once you got to know it, largely seemed like one of the main stench culprits. The bottle stayed in the room, measurement was done right there. You had to put on a disposable suit to protect you from the outer suit which was assumed to be contaminated from previous tasks. Full face respirator and shield, rubber boots and spats, multiple glove layers to open the crate, dig into the vermiculite for the can, open with sparkproof tools, dig into more vermiculite for the bottle of ugly red liquid its damn self. Any access to thiophosgene called for full replacement of the bottle cap, can, crate, and vermiculite, so it could hopefully be left alone as long as possible undisturbed afterward. Once opened and repacked, that room smelled about ten times worse than normal for a couple weeks even though the thiophosgene was sealed up like that. Anyway, I have lived by my teenage decision but accept it as immature, I don't recommend such toxic or dangerous work to others and carry on partially because I want to use any unfair advantage for myself & others to handle risky things more responsibly or not at all.