"...benzene holds a special place in education. Generations of high school and university students have been introduced to the elegance of its structure and the profound mystery surrounding its stability."
Admire it from a distance.
"Benzene is classified as a carcinogen, which increases the risk of cancer and other illnesses, and is also a notorious cause of bone marrow failure. Substantial quantities of epidemiologic, clinical, and laboratory data link benzene to aplastic anemia, acute leukemia, bone marrow abnormalities and cardiovascular disease.
"...There is no safe exposure level; even tiny amounts can cause harm."
I want a better list than the IARC because their Group 1 has substances like benzine and asbestos along side things like Alcoholic beverages, Chinese-style Salted fish and processed meat.
oidar · 2m ago
The evidence is very strong for all of those. They should be in Group 1.
isoprophlex · 2h ago
Yeah, indeed it aint healthy... but that didn't stop me from smelling it just once in undergrad. I had to get at least one whiff of this iconic compount
kybernetyk · 1h ago
How does it smell?
cenamus · 1h ago
Sweet, but still kind of like hydrocarbon if I remember right. Definitely strang
pumnikol · 10m ago
Sweet? I'd rather liken it to period blood, but more metallic and kind of... vicious. Its smell is hardly comparable to its relatives xylene, toluene, ethyl benzene.
landl0rd · 1h ago
You can get a little dose and it's likely not going to hurt you. "No safe dose" doesn't mean "any dose is massively injurious". You smell it regularly when you pump gasoline.
Funny enough benzene used to be used (a hundred years ago) for aftershave and even for douches. I don't even want to think about what that did to those people's bodies.
When I studied organic chemistry in high school, everything was theoretical and done on paper. We had lab sessions for only inorganic chemistry.
chasil · 10m ago
In 1986, I made nylon, and I am 98% sure that we had benzene.
ncfausti · 1h ago
This.
When an alarming number of friends (all under 40 years old) from the same small neighborhood in my hometown were diagnosed with leukemia I started to look into the superfund site nearby. The pond that is connected to the stream that supplies the municipal wells in the area was still disgusting (with visible oily residue on the surface) nearly 15 years after the company, Congoleum, stopped operations and the plant was demolished. Soil testing some years earlier revealed benzene, which has been linked to AML.
cyberax · 1h ago
It's likely that benzene's danger is a bit exaggerated. Certainly don't smear it casually on yourself, but it's unlikely to be in the same league as something like acrylonitriles.
aszantu · 2h ago
Lots of sunscreen and other beauty products seem to be contaminated with benzene. Johnson & Johnson was caught a few times putting it in baby powder or something
dylan604 · 2h ago
J&J's baby powder situation was related to asbestos[0]. So it must be under your "or something" hand wavy qualifier. If you're going to sling dirt, at least make it accurate. The benzene use was in other products like sunscreen[1]
They mention the sunscreen in the other sentence of the post.
I gotta say, your post comes off (maybe I’m misreading it) as a bit critical, given that you seem to agree with the other poster as to the underlying problem (frequent contamination issues).
dylan604 · 1h ago
I'm critical of making correct accusations. Baby powder never had a bezene problem which was being implied. Baby powder definitely had issues, but different issues. J&J as a company definitely plays fast and loose with product ingredients vs health safety, but when making accusations, accuracy is important.
You wouldn't want chatGPT or claude to start saying that J&J was using benzene in baby powder after scraping HN for training data because we played it loose with facts would you? In fact, we call LLM incorrectness as hallucinating, so would you be less upset if I said that the other person was hallucinating?
bee_rider · 1h ago
Sure. I basically agree that their comment was sloppy, I just think for example:
> If you're going to sling dirt, at least make it accurate.
Something that might fit your sentiment better could be:
> It is right to sling dirt, but it is important to make it accurate.
There’s a ton of pro-corporate propaganda out there, so the good guys should stick together too.
hildolfr · 45m ago
Reinforcing the strength of a future corporate product by doing their fact checking for them has got to be one of the weakest reasons for correctness and precision I've ever come across.
Please use a better example for the virtues of being correct, there are heaps better reasons.
badgersnake · 53m ago
> You wouldn't want chatGPT or claude to start saying that J&J was using benzene in baby powder
That would be annoying, but since everyone checks their outputs against trusted sources, it wouldn’t be a major issue.
kccqzy · 3h ago
> Its peculiar behaviour, such as its surprising stability despite being highly unsaturated, hinted at a deeper mystery that would not be fully resolved until the mid-19th century with the proposal of its cyclic structure.
How were chemists in the early 19th century able to determine benzene must be highly unsaturated without knowing its structure? Did they simply combust it and measure the amount of water vapor and carbon dioxide produced?
jcranmer · 40m ago
There's a two step-process to stochiometry.
The first step, as people have elaborated below, is combust the compound and measure the weights of various oxides, which (after the atomic masses of the relevant elements were settled around the 1820s) lets you work out the empirical formula of an unknown molecule. For benzene, this would tell you that there is 1 C : 1 H, but this doesn't tell you if it's C₄H₄ or C₆H₆ or C₁₁₁H₁₁₁.
The second step is to determine the molar mass of your compound, which requires finding something that depends on the amount of substance but not the mass directly. (In modern times, this is primarily mass spec). Back in the 19th century, this is probably abusing the ideal gas law, which lets you compute the number of moles in a gas given the pressure, temperature, and volume of a vessel. Combine this with the mass of that container, and you know how much a mole weighs. If you get out, say, 77g/mol, and you know that the ratio is 1 C : 1 H, well, the only formula that makes sense is C₆H₆ (which should ideally have 78g/mol, but you might not get the right answer for various experimental reasons).
isoprophlex · 2h ago
What these early chemists accomplished with, to our eyes, extremely crude methods is astounding. Physical methods like weighing, burning and collecting residue; describing crystallization and precipitation behavior, even smelling (and sometimes tasting) was at one point a routine thing to do.
How cool, it's still in the ACS logo! Germans have the best names lol. Calibration apparatus.
sndean · 2h ago
Yeah an apparatus like that and work out that benzene had a very different carbon dioxide to water ratio than something like hexane.
Horffupolde · 1h ago
Yes.
joloooo · 1h ago
Interesting article. I have always viewed Benzene as a bogeyman of sorts. My parents both interacted with it often throughout my life. My dad was a chemical engineer for an oil company, and he often spoke of spills and incidents. As a kid, I never understood what it was, but the tone and urgency were always something scary.
I also strongly suspect my mother's Benzene exposures (nurse cleaning lab slides with Benzene and no PPE) led to me battling Langerhans Histiocytosis throughout my childhood.
I'll admit I know very little chemistry, but I think the article would've been much better for people like me of it included any specific examples at all of benzene uses. It's filled with assurances that it's important and used all over the place but I didn't find that very enlightening.
Benzene is used mainly as an intermediate to make other chemicals, above all ethylbenzene (and other alkylbenzenes), cumene, cyclohexane, and nitrobenzene. More than half of the entire benzene production is processed into ethylbenzene, a precursor to styrene, which is used to make polymers and plastics like polystyrene. Some 20% of the benzene production is used to manufacture cumene, which is needed to produce phenol and acetone for resins and adhesives. Cyclohexane consumes around 10% of the world's benzene production; it is primarily used in the manufacture of nylon fibers, which are processed into textiles and engineering plastics. Smaller amounts of benzene are used to make some types of rubbers, lubricants, dyes, detergents, drugs, explosives, and pesticides.
It's an important feedstock in the chemical industry but it is no longer used directly in household products. It used to be common in solvent/glue/grease remover formulations before the health hazard was widely appreciated.
andrewflnr · 37m ago
It's kind of hard to explain how widespread a usage like "solvent" is. A huge amount of chemical reactions are most convenient to do in a liquid, a liquid that can dissolve the materials you're working with. That's a solvent. Benzene can dissolve a lot of things, including some that are really hard to dissolve otherwise. So it can be used for a huge variety of reactions, but as the sort background player that you might not pay attention to unless you can't have it.
It's a little like asking "what are the uses of water in chemistry", where you're tempted to answer, "um, everything?" Not quite, but not that far off either. (And with more cancer of course.)
Edit: disclaimer, I'm not a chemist, just an interested layman.
_WhySoSerious_ · 3h ago
Kekule who dreamt of 6 serpents each eating others tail and discovered the hexavalent structure, meanwhile cries in a corner. No mention of Kekule in the article.
(I had the impression from somewhere else that his "reverie or day-dream" might have instead been a pipe dream — as in the literal pipe dream (opium?). But I can now find nothing to substantiate this at all so, maybe just ignore.)
For a tangent on Kekule, I really enjoyed Cormac McCarthy's essay The Kekule Problem - published in 2017 and apparently his first published work of non-fiction.
Omitting such an important story from the article feels sloppy.
For me, no other story from Chemistry is as fascinating as Kekule dreaming up Benzene’s molecular structure. An important reminder to me about the power of narrative and storytelling.
meepmorp · 1h ago
Yeah, and it's especially sad because they specifically mention that the structure was worked out later in the 19th century. Why not include a fun little detail like that?
The answer is probably because the author hasn't taken organic chem and so never heard the story.
carbocation · 2h ago
This does seem like an important omission.
gavinray · 1h ago
I immediately "Ctrl+F" for "Kekule" and saw nothing on the page. Disappointing.
When I read a "History of Organic Chemistry" textbook, Kekule and Benzene were essentially the springboard.
andygeorge · 2h ago
I was a kid when there was a Benzene spill up where I lived at the time (Duluth, MN). I remember having to evacuate to our aunt's house out of town. My dad stayed at home doing yardwork until he felt "a little lightheaded" and finally joined us.
Seattle’s Gas Works Park has some strange equipment to address the benzene contamination. Bold move to make industrial sites into parks (it is one of the best in Seattle though!)
The article talks about the wonders of bucky balls and nanotubes - does anyone know what useful stuff has come out of those yet? I think I heard there's some work on nanotubes coming up on transistors in the next gen of chips?
Not sure what bucky balls and other fullerenes are being used for? (I remember originally there was talk of lubricants?)
bell-cot · 1h ago
> does anyone know what useful stuff has come out of those yet?
Quip: Every chemical researcher's #1 need is for research funding, no?
k__ · 35m ago
I did an internship at a chemical laboratory once.
The older folks told me that they aren't allowed to use the awesome stuff anymore.
Back in the days, they would use Benzene for everything, the only stuff that would get the lab floors clean at the end of the day.
Same with asbestos, leaded fuel, and whatnot. Compounds that are perfect for their use cases, yet highly toxic.
pumnikol · 6m ago
One of my elderly colleagues once told me that at the end of each day, they'd put all the lab coats in a big vat of benzene to clean them. The next day, they took them out, let them dry for a short while and then just put them on again. I think it was in the early 80s? He did develop cancer later.
jabl · 42m ago
I remember in high school chemistry (or physics?) we had a wooden model of the benzene ring with the ground state molecular orbitals. Diameter about 30cm.
euroderf · 43m ago
Benzene must've been examined down to the nth degree in quantum analysis. Maybe there's an article ?
Brajeshwar · 3h ago
I realize the article is asking for a login (a free account). Here is the Archived link
I've read that back in the day chemists used to nearly bathe in this stuff. Now it's rarely used in instructional chem labs. Heck as an undergrad in the 90's we were using Potassium Dichromate as an oxidizer. I spilled some on me and it ate through my lab coat and shirt beneath it. Probably should have had an apron on too...
groos · 1h ago
I once pulled on a glass pipette too hard and got benzene in my mouth. This was 36 years ago, still doing well :-)
scottlawson · 2h ago
I love articles like this that give the context and history to important but not often talked about molecules. I enjoyed this as much as the "chemicals I will never work with" series.
divbzero · 2h ago
It amazes me that the same person who discovered benzene also discovered electromagnetic induction and Faraday’s laws of electrolysis.
ipdashc · 2h ago
> and Faraday’s laws of electrolysis
Wow, what are the chances he discovers something with a name like that?
nanna · 1h ago
And wasn't Faraday also a self-taught amateur whose maths was so poor that he couldn't even do trigonometry?
A beacon of hope for those of us without doctorates in physics out here...
Admire it from a distance.
"Benzene is classified as a carcinogen, which increases the risk of cancer and other illnesses, and is also a notorious cause of bone marrow failure. Substantial quantities of epidemiologic, clinical, and laboratory data link benzene to aplastic anemia, acute leukemia, bone marrow abnormalities and cardiovascular disease.
"...There is no safe exposure level; even tiny amounts can cause harm."
https://en.wikipedia.org/wiki/Benzene#Health_effects
Funny enough benzene used to be used (a hundred years ago) for aftershave and even for douches. I don't even want to think about what that did to those people's bodies.
When an alarming number of friends (all under 40 years old) from the same small neighborhood in my hometown were diagnosed with leukemia I started to look into the superfund site nearby. The pond that is connected to the stream that supplies the municipal wells in the area was still disgusting (with visible oily residue on the surface) nearly 15 years after the company, Congoleum, stopped operations and the plant was demolished. Soil testing some years earlier revealed benzene, which has been linked to AML.
[0]https://www.reuters.com/investigates/special-report/johnsona...
[1]https://www.jnj.com/media-center/press-releases/johnson-john...
I gotta say, your post comes off (maybe I’m misreading it) as a bit critical, given that you seem to agree with the other poster as to the underlying problem (frequent contamination issues).
You wouldn't want chatGPT or claude to start saying that J&J was using benzene in baby powder after scraping HN for training data because we played it loose with facts would you? In fact, we call LLM incorrectness as hallucinating, so would you be less upset if I said that the other person was hallucinating?
> If you're going to sling dirt, at least make it accurate.
Something that might fit your sentiment better could be:
> It is right to sling dirt, but it is important to make it accurate.
There’s a ton of pro-corporate propaganda out there, so the good guys should stick together too.
Please use a better example for the virtues of being correct, there are heaps better reasons.
That would be annoying, but since everyone checks their outputs against trusted sources, it wouldn’t be a major issue.
How were chemists in the early 19th century able to determine benzene must be highly unsaturated without knowing its structure? Did they simply combust it and measure the amount of water vapor and carbon dioxide produced?
The first step, as people have elaborated below, is combust the compound and measure the weights of various oxides, which (after the atomic masses of the relevant elements were settled around the 1820s) lets you work out the empirical formula of an unknown molecule. For benzene, this would tell you that there is 1 C : 1 H, but this doesn't tell you if it's C₄H₄ or C₆H₆ or C₁₁₁H₁₁₁.
The second step is to determine the molar mass of your compound, which requires finding something that depends on the amount of substance but not the mass directly. (In modern times, this is primarily mass spec). Back in the 19th century, this is probably abusing the ideal gas law, which lets you compute the number of moles in a gas given the pressure, temperature, and volume of a vessel. Combine this with the mass of that container, and you know how much a mole weighs. If you get out, say, 77g/mol, and you know that the ratio is 1 C : 1 H, well, the only formula that makes sense is C₆H₆ (which should ideally have 78g/mol, but you might not get the right answer for various experimental reasons).
No comments yet
https://en.wikipedia.org/wiki/Kaliapparat
I also strongly suspect my mother's Benzene exposures (nurse cleaning lab slides with Benzene and no PPE) led to me battling Langerhans Histiocytosis throughout my childhood.
https://en.wikipedia.org/wiki/Langerhans_cell_histiocytosis
Benzene is used mainly as an intermediate to make other chemicals, above all ethylbenzene (and other alkylbenzenes), cumene, cyclohexane, and nitrobenzene. More than half of the entire benzene production is processed into ethylbenzene, a precursor to styrene, which is used to make polymers and plastics like polystyrene. Some 20% of the benzene production is used to manufacture cumene, which is needed to produce phenol and acetone for resins and adhesives. Cyclohexane consumes around 10% of the world's benzene production; it is primarily used in the manufacture of nylon fibers, which are processed into textiles and engineering plastics. Smaller amounts of benzene are used to make some types of rubbers, lubricants, dyes, detergents, drugs, explosives, and pesticides.
It's an important feedstock in the chemical industry but it is no longer used directly in household products. It used to be common in solvent/glue/grease remover formulations before the health hazard was widely appreciated.
It's a little like asking "what are the uses of water in chemistry", where you're tempted to answer, "um, everything?" Not quite, but not that far off either. (And with more cancer of course.)
Edit: disclaimer, I'm not a chemist, just an interested layman.
https://i.imgur.com/EGyYmkX.jpg
https://www.nytimes.com/1988/08/16/science/the-benzene-ring-...
(I had the impression from somewhere else that his "reverie or day-dream" might have instead been a pipe dream — as in the literal pipe dream (opium?). But I can now find nothing to substantiate this at all so, maybe just ignore.)
EDIT: perhaps I was reading too much into this page from the Golden Book of Chemistry: https://www.slideshare.net/slideshow/the-golden-book-of-chem...
For me, no other story from Chemistry is as fascinating as Kekule dreaming up Benzene’s molecular structure. An important reminder to me about the power of narrative and storytelling.
The answer is probably because the author hasn't taken organic chem and so never heard the story.
When I read a "History of Organic Chemistry" textbook, Kekule and Benzene were essentially the springboard.
https://en.wikipedia.org/wiki/1992_Nemadji_River_train_derai...
Edit: better link https://apps.ecology.wa.gov/cleanupsearch/site/2876
Original link was older 2005 report: https://apps.ecology.wa.gov/cleanupsearch/document/1509
Quip: Every chemical researcher's #1 need is for research funding, no?
The older folks told me that they aren't allowed to use the awesome stuff anymore.
Back in the days, they would use Benzene for everything, the only stuff that would get the lab floors clean at the end of the day.
Same with asbestos, leaded fuel, and whatnot. Compounds that are perfect for their use cases, yet highly toxic.
https://archive.is/X1iHZ
Wow, what are the chances he discovers something with a name like that?
A beacon of hope for those of us without doctorates in physics out here...