Talk:Phenol/Archive 1

Phenol is NOT Sulfur Dioxide
Cautionary Note Phenol is NOT sulfur dioxide, although some government agencies may claim so:

http://www.atsdr.cdc.gov/mhmi/mmg115.html —Preceding unsigned comment added by 76.122.34.134 (talk) 00:01, 26 February 2009 (UTC)

Phenol as a natural factor in food
Please forgive my ignorance as I'm not a chemist, just a mom who's son is said to be intolerant to phenols. I see nothing on the wikipage about phenols being a natural component of foods and issues around phenol sensitivity. There are however, enzymes available to help digest phenols. Where can a person get more information on this? Thanks —Preceding unsigned comment added by 121.72.42.207 (talk) 18:53, 23 November 2008 (UTC)

Dear Mom,

I believe there has been some misunderstanding. While "phenol", the molecule this article mainly talks about, is also called many names (carbilic acid, etc) and is the compound used for making plastics, in medicine and in many other fields, a phenol, in general, is a molecule that has six carbons making a ring. It is similar to what happens with "sugar" (what you buy at the supermarket), and a sugar, which is any crystaline carbohydrate. There are plenty of phenols in food, meaning there are plenty of those six-carbon rings. In first place, there is an aminoacid, phenylalanine, which can be found in any protein, that has a phenolic ring. You can find phenols in wine, in the hormones your body produces, in medicines, in plants, and everywhere around us, in any organic material, just like you find sugars, fats (lipids) or proteins... Any organism has ways (pathways) to remove toxic compounds, that can come from the environment (xenobiotics) or also produced by the same organism (detoxification pathways). In a clinical paper written in 1996, McFadden proposes that "impaired sulfation of phenolic xenobiotics may be relevant to intolerance of phenol, tyramine, and phenylic food constituents, and it may be important in multiple chemical sensitivities and diet responsive autism". It appears that what some people call "intolerance to phenols" is a defect in this mechanism of detoxifying phenols in the body, a mechanism called xenobiotic sulfation. However, there are 3 mechanisms that detoxify phenol. If you want to find more info on the pathways, there is a review: available online: http://www.altmedrev.com/publications/3/3/187.pdf

93.188.137.23 (talk) 19:52, 7 June 2011 (UTC) Crisgil

Dear "mom",

Phenol is found very frequently in the environment, in cigarette smoke etc. I was astonished to learn that phenol is major ingredient in some cold medications! Check this one, for example:

http://www.atsdr.cdc.gov/mhmi/mmg115.html

Unfortunately, the article is messed up, the info on phenol is mixed up with information on sulfur dioxide.

Sincerely,

NdT

Phenol UV absorbance and fluorescence spectrums available
might be a good link to include.

Phillip SanMiguel (talk) 13:46, 19 March 2008 (UTC)

Phenol use in Nazi concentration camps
NightCrawler made the following change, which I have reversed:


 * Patients of Auschwitz and other concentration camps were often killed by phenol injections.


 * [ed: prior version was Patients of the Auschwitz I concentration camp hospital were often killed by phenol injections.]

Apart from referring to 'patients' of concentration camps (?) - an indication of slap-dash thinking - this change seems to have been made merely to support a change, also made by NightCrawler, to the Diana Rowden page, concerning the use of phenol on prisoners - the issue being whether or not certain prisoners injected with phenol at Natweiler concentration camp were still alive when placed in a crematorium oven.

Eye-witness testimony (quoted on Talk:Diana Rowden) suggests that they were indeed still alive, but NightCrawler wishes to deny this, although his/her grounds for doing so are not clear.

I have no issue with the statement that people were killed by phenol injection at more than one concentration camp. My concern is merely that the version prior to NightCrawler's change was more objective. Petermanchester 11:24, 13 Nov 2003 (UTC)

The administrators of the German Wikipedia have frozen the Phenol article in a version which does not include reference to this bit of history. In the German article discussion, they choose not to respond to the argument that the English Wikipedia does mention this as being relevant. I cannot understand why the relevance should be related to the language.--Bhuck 11:37, 23 December 2005 (UTC)wow sooooooo interesting i have no clue what the heck there talking about.

Oops, sorry--there was a lot of reverting back and forth, and I got confused about which was the protected version. Upon further reflection, I've also decided that there is probably a better place to discuss these issues than an article about phenol. Sorry to bother anyone (though so far, no one seems to have paid much attention, anyway).--Bhuck 13:58, 23 December 2005 (UTC)


 * I saw your message, I was just waiting for you to come round to my point of view ;-) I am sure that phenol was used in concentration camps for murdering inmates, as were many other chemicals. "Schindler's Ark" contains a passage about the euthanasia of ghetto hospital patients with hydrogen cyanide to save them from an injection of benzene. However, I can't say that I find this the most notable piece of information about the chemical compound. It can certainly be left out, and on the balance I think it should be. As for German wiki, there have their ideas and we have ours: the different language versions are not necessarily identical in scope, nor should they be! Physchim62 (talk) 17:13, 27 December 2005 (UTC)

The Mengele comment seems totally out of place in an otherwise well-written scientific article. Certainly as scientists you would have to ask yourself what the basis is for any claim. Keneally is not a source so much as an end-user. If it's so absolutely obvious that the statement is true, then it should be absolutely simplistic to find the source of the info. It's like saying salt is made of sodium chloride and not having the slightest idea what the basis is for that knowledge other than "everybody says so". On top of that, it's just jarring to run across it at the end of an article oriented towards science.

I am really wondering myself why this true KZ past is mentioned in combination with an article like phenol. Intrakardial Injektion with plain air are fullfilling the same purpose. More or less the Germans have learnt quite well about their past. This kind of implementing true facts, where they really do not belong, is in my personal point of view only there, to put still shame and guilt onto Germans and their historical past.

PS: Is their any given evidence about the exact amount of people beeing killed over this cruel and terrible way. Kind regards--Ekkenekepen 08:46, 19 October 2006 (UTC)

confirms injection in the heart but does not refer to a prior practice of injection in the arm. Jack Waugh (talk) 23:09, 3 January 2008 (UTC)

Dermabrasion??
Isn't phenol used for dermabrasion? H Padleckas 12:38, 11 Apr 2005 (UTC)
 * You bet, not only that, it was commonly used for cortorizing/sterilizing, I forget which, in dentistry before preferrable options became available. Will chase up some references and get back to you. GreatMizuti 14:28, 10 April 2006 (UTC)

Esterification
How readily does phenol form esters? Is there any special conditions that are required, like reflux or maybe an acid catalyst? Would it be easier to esterify it to a carboxylic acid than an alcohol? Can the reactant be a catalyst too? I assume it would be easier still to esterify with a diacid like oxalic acid? Lots of questions :) mastodon 23:24, 16 April 2006 (UTC)



Solubility in water
The article states that phenol has a solubilty of 8.3 g/100 mL water, but the chembox says that it has a solubility of 9.8 g/100 mL water. Which is correct? Jesse 02:57, 13 May 2006 (UTC)


 * I reckon that the 8.3 g/100 mL value is at 0°C and the 9.8 g/100 mL is at room temperature. Check it out online.  --Ben 08:08, 13 May 2006 (UTC).


 * I found a few sites that listed the solubility as 8% w/w at room temperature . I don't know where the 9.8 g/100 mL came from, but I changed the value in the chembox. Jesse 03:35, 26 May 2006 (UTC)


 * Since the anion is "highly water-soluble" the exact miscibility in water probably depends on pH. Phillip SanMiguel (talk) 13:46, 19 March 2008 (UTC)

More on Solubility in water
The article also states that above 40ºC Phenol is completely miscible in Water, that is incorrect, and a proof of that is that it doesn't cite a source. In a recent laboratory experience I had, we determined the critical temperature of dissolution for a phenol-water system to be about 68,6ºC, we may be wrong by some degrees, but NEVER by 28 whole degrees centigrades. I am going to remove that part of the article until somebody cites a reputable source. Pentalis 00:26, 16 October 2006 (UTC)

Phenol fumes?
I work in an environmental laboratory and work directly with phenol crystals. Phenol plays a part in the chemical procedure for ammonia testing ( which I carry out). I have been working in close proximity with phenol pumping into a drain, in an enclosed room, however the drain has been faulty for approx 2 months and pungent smells/fumes and spills are frequent. Is this exposure likely to be dangerous? I am particularly concerned about the inhalation as skin to skin contact is rare as i wear appropriate protective gear. ( on a side note from another discussion i saw, 8.3g/100ml is the correct capacity of phenol to dissolve in liquid.)
 * One of the R-phrases for phenol is : Toxic: danger of serious damage to health by prolonged exposure through inhalation, in contact with skin and if swallowed.  I don't think it is a good idea to work under the conditions you describe.  Your employer should fix the problem immediately. --Ed (Edgar181) 13:24, 18 May 2006 (UTC)


 * In the laboratory I work in, part of our standard operating procedure for any form of phenol is that it be worked with exclusively in a fume hood. This is based off of the risk assessment of inhalation danger.  As Edgar181 points out, you may want to discuss it with your employer.  Chances are there's an OSHA regulation about this. Dcteas17 01:10, 18 August 2006 (UTC)


 * Phenol has a threshold limit value of 5 ppm, making it one of the more harmful compound to breathe on my list here, similar to con. hydrochloric acid, carbon disulfide, and sulfur dioxide. No way you should be making ANY habit out of breathing this stuff. Second, you can get in serious trouble for flushing so much down the drain. It should be treated as hazardous waste and disposed of through a professional waste handler. Awaspaas 03:38, 29 October 2006 (UTC)

Lip balm?
Isn't (wasn't) phenol used in lip balm/chapstick? If so, perhaps there should be a link. --User:Haligonian1 10:24, 6 June 2006 (UTC)


 * It and camphor are still used in Carmex, which is a little disturbing to me since phenol is a pretty nasty poison and camphor is an irritant. Awaspaas 03:41, 29 October 2006 (UTC)

>>>Unfortunately, yes. In a whole lot of cold medications NdT —Preceding unsigned comment added by 76.122.34.134 (talk) 02:53, 11 February 2009 (UTC)

It is also the only current active ingredient in chloraseptic spray in a volume of 1.4%. —Preceding unsigned comment added by 24.118.133.205 (talk) 03:14, 12 March 2009 (UTC)

Treatment for hemorrhoids and snoring
phenol is used as an injection into internal hemorrhoids to shrink/shrivel/cauterize them. Also its being used in somnoplasty/snoring procedures, injected under the skin of the soft palate to cause a subdermal wound, which when it heals, the scar tissue that forms stiffens the soft palate, reducing snoring.

Inductive effect
The statement about inductive effects being responsible for phenol's acidity makes no sense. The only reason it is acidic is due to p orbital overlap which delocalizes the negative charge over the ring, stabilizing the phenoxide ion. In fact, it's oxygen's inductive effect that attenuates the delocalization, making phenol a relatively WEAK acid, not a stronger acid compared to aliphatic alcohols. I think the original author had those confused. That sentence should be fixed or removed. awaspaas
 * Edited article to reflect above. Awaspaas 03:30, 29 October 2006 (UTC)

Sorry, but this is not correct yanamad 03:20, 14 March 2007 (EST)


 * Well, leave it to Dave Evans to make the rest of us chemists feel stupid! Is that theory published?Awaspaas 16:34, 2 April 2007 (UTC)

Consider toluene. It is not very acidic at all (pKa ≈ 40, see ). Phenol is much more acidic (pKa ≈ 10). What you're saying is without oxygen's inductive effect, phenol would be a stronger acid. How can this be the case? Toluene's methyl group doesn't have much of an inductive effect, yet it is not a stronger acid than phenol. Quite the opposite, in fact.

Ben 16:50, 2 April 2007 (UTC)

Cats?
Is the statement about phenol being toxic to cats necessary? It seems rather trivial, since phenol is exceedingly toxic to not only cats, but most forms of life. Unless there is evidence that phenol is a significant killer of cats (such as antifreeze with pets), this statement merely trivializes the severe toxicity associated with phenol ingestion or contact. Dcteas17 05:41, 19 January 2007 (UTC)

Cats2?
The juxposition of toxicit to cats just following it's use as a Nazi murder weapon seems sureal if not sinister. Glad to know that cats rank up there with Jews, Gypsies, Homosexuals, Slavs and Pols. ;)

Benzene hydroxide/hydroxy benzene/phenyl hydroxide
When searching the above terms this page does not come up... thought this could be a common mistake made by someone with limited knowledge of organic chem when searching the wiki and that these terms should lead to the phenol page incorrect as they are. Am going to make the change, please advise if you feel this move is a bad one. --Marshmellis (talk) 10:26, 20 May 2008 (UTC)


 * The reason these terms do not redirect to Phenol is because they are either wrong or very rare. "Benzene hydroxide" is just plain wrong. Hydroxybenzene (no space) is already given in the phenol article as an alternate name. "Phenyl hydroxide" is a rare alternative. As a chemist with over 35 years experience, I have never heard this term. I would suggest not adding them to Wikipedia since this would lead to them being picked up by search engines like Google and giving them more creedence than they deserve. Silverchemist (talk) 19:34, 20 May 2008 (UTC)


 * Thanks for the feedback silver, I have only really done high school and first year uni chemistry so I wasn't too sure how appropriate my edits would be... which redirects do you think should be kept and which should be ditched? I fully agree with the notion of incorrect nomenclature gaining more creedence than it should as a result of redirects such as these, I thought perhaps a qualifier could be added to the article?
 * My thoughts were that the above terms (incorrect as they are) are an easy conclusion to arrive at as the name for this compound. Someone wondering about what effect adding an -OH onto benzene might have may not be able to find this information without these redirects, however it is necessary to reinforce that the nomenclature they have arrived at is indeed incorrect. It seems to me that an appropriate solution would be a qualifier within the article outlining the appropriate and inappropriate names for phenol, or even a page for "benzene hydroxide" that basically says "you're wrong, you might be looking for this". Thoughts? PS please excuse the essay, I do tend to be too verbose :P --Marshmellis (talk) 00:41, 21 May 2008 (UTC)


 * "Hydroxybenzene" may be worth adding. As for someone looking for derivatives of benzene (eg. "What would you get if you add X to benzene?"), that is already a section in the benzene article. Perhaps it would be a better idea to expand this section of the benzene article than to start new pages.Silverchemist (talk) 01:52, 21 May 2008 (UTC)


 * I had a look at some related pages i.e. toluene and aniline (the other two of the three named benzene derivatives on the benzene page) and found that toluene says "Toluene, also known as methylbenzene or phenylmethane" while aniline says "Aniline, phenylamine or aminobenzene is an organic compound". It seems to me that these three pages should have a similar approach to synonyms, for consistency's sake. If phenol does indeed have markedly different naming conventions to the other two this certainly needs to be explained. I recognise that benzene hydroxide is incorrect, and should not have a place anywhere in the article however if one follows the convention used in the other two articles (which seems appropriate to me) it would produce something like "Phenol, also known as hydroxybenzene, phenylhydroxide or by its old name of carbolic acid is a toxic, colourless crystalline solid with a sweet tarry odor" as the leading sentence of the article. Either this or a change to the other two articles to achieve cohesion seems to me a good course of action. What are your thoughts on this? --Marshmellis (talk) 04:28, 22 May 2008 (UTC)
 * Me again :S was just wondering how I should be going about deleting the "hydroxybenzene" redirect I made, should I just delete something this trivial or should I recommend deletion? Please excuse my newbieness :) --Marshmellis (talk) 04:36, 22 May 2008 (UTC)
 * Just popped my head in- re the naming- to my knowledge phenol is not known as hydroxybenzene or phenylhydroxide, hence the absence. I've just added carbolic acid. Freestyle-69 (talk) 00:39, 24 October 2008 (UTC)

prebiotic phenol
I am not sure the assertion that "the implications of prebiotic phenol are questionable at best" is apparent based on the references given. I also fail to see what relevance hydroxylation of phenylalanine has to the implications of abiotic phenol, and it incorrectly draws the reader to an unsupported conclusion. We could discuss this further if desired.

I suggest deletion of the "Hydrothermal chemistry" section unless someone would like to explore it more thoroughly and lucidly without original research.

Atatepilot (talk) 02:22, 5 August 2008 (UTC)

Phenol is NOT blue/green or aqua when pure it is a white/crystalline solid! Check most images of phenol to see this. —Preceding unsigned comment added by 82.228.42.45 (talk) 06:54, 1 May 2011 (UTC)

Chemical burns
Should this be expanded? Thanks to an idiot I went to college with I suffered a bad phenol burn, and it was very different from the usual chemical burn fare (delayed action, waiting until it gets under the skin to start burning, making the skin above it white and ready to peel off like wet tissue paper and feeling more like a really bad nettle sting than an actual burn). 78.151.220.203 (talk) 07:32, 25 September 2008 (UTC)
 * Why not. Phenol is rather unusually in it's mode of action. It numbs the skin so fast that you rarely feel any contact, it then proceeds to attack the skin without any pain. Also it is passing through the skin and not doing the rest of you any good. People who have fell into drums of just molten phenol, are dead by the time you can get them out.  I was always told that covering the area of one thigh with phenol could well be fatal.   Ron h jones  (Talk) 22:21, 5 March 2009 (UTC)
 * Some people have a sensitivity to phenol. Also, urushiol is a type of phenol (see Phenols) which is the active ingredient in the skin irritant (causes a skin rash) in poison ivy.  Chemical compounds within a class of compounds such as phenols often have similar properties.  H Padleckas (talk) 02:43, 17 March 2010 (UTC)

reference to carbolic acid in a famous blues song
I'm not sure where to put this, but my research on a song called "Sold it to the Devil," which was recorded by many blues singers including Clara Smith, John D. Twitty, Merline Johnson, and Casey Bill Weldon, has brought to light a memorable verse that is relevant for this entry. Here's Twitty's version:

I’ve sold my soul, sold it to the devil, and my heart done turned to stone / I’ve sold my soul, sold it to the devil, but he won’t let me alone / Said I’m hateful and I’m evil, I carries a Gatling gun / I drink carbolic acid, be darned if I will run / But I’ve sold it, I have sold it, sold it to the devil, and my heart done turned to stone

Make of that what you will! 74.229.164.106 (talk) 21:16, 30 January 2009 (UTC)

Phenol in embalming
I didn't site any sources when adding information about embalming in the uses section of phenol, but I figured I should explain. I'm a student of mortuary science (funeral directors/embalmers/morticians) and for all anatomical embalming we use HIGH concentration solutions of phenol. Its probably the best preservative from a standpoint of preserving a body so that it wont decompose, but distorts features to the point of making identity of individuals unrecognizable. I think the important chemical reactions that take place alter the structure of amino acids in the body. —Preceding unsigned comment added by 24.118.133.205 (talk) 03:20, 12 March 2009 (UTC)

Aqueous Phenol
Is used for solvent welding nylon parts.--69.154.215.29 (talk) 07:01, 21 June 2009 (UTC)

glow stick phenol
I had glow stick fluid on my hand and the phenol in the fluid gone into my eye. I urgently washed it off. Are glow sticks dangerous? Wikieat (talk) 17:31, 28 November 2009 (UTC)

Edits of March 2010
The article is undergoing some major edits. Readers are welcome to revert or critique the process. I removed a paragraph: "Under laboratory conditions mimicking hydrothermal circulation ... may be relevant to the origin of life", which seems fine for a blog but not a broad overview of a basic industrial chemical. The sections on its solvation (a student essay?) and use as a WWII poison seem disproportionately long. On the other hand, the reactivity is only lightly discussed. We have almost no history. Too many refs are to primary literature, we have too few overviews of phenol (e.g. Ullmann's), and several refs are to .com sources.--Smokefoot (talk) 20:32, 14 March 2010 (UTC)

why phenols are not included in alcohols though they have OH group?

Qualified person needs to edit?
I'm slightly confused. I am by no means a chemist but in the last section of "production" - Oxidation of Toluene, where does the sulphur come from? I don't see it anywhere on the left side of the reaction. — Preceding unsigned comment added by 72.226.92.108 (talk) 02:00, 7 October 2011 (UTC)

Tautomerism self-contradiction
I'm no chemist, but the following paragraph appears to state an unacknowledged self-contradiction. The first claim (very minimal tautomerism) is more nuanced than the second (no tautomerism), so at a wild guess I would assume the first claim is more correct. I would prefer if a qualified editor were to handle this (or explain my error here), but if there is no activity over the next few months then I may simply excise the last sentence.

Phenol exhibits keto-enol tautomerism with its unstable keto tautomer cyclohexadienone, but only a tiny fraction of phenol exists as the keto form. The equilibrium constant for enolisation is approximately 10−13, meaning that only one in every ten trillion molecules is in the keto form at any moment.[11] The small amount of stabilisation gained by exchanging a C=C bond for a C=O bond is more than offset by the large destabilisation resulting from the loss of aromaticity. Phenol therefore exists entirely in the enol form.[12] — Preceding unsigned comment added by 129.6.153.104 (talk) 23:36, 19 September 2012 (UTC)
 * looks ok to me, very very minimal tautomerization. --Smokefoot (talk) 23:46, 19 September 2012 (UTC)

"Exposure may result in death and the effects may be delayed."
What does that even mean? This has to be the most poorly-phrased sentence on this page.

38.112.19.2 (talk) 16:50, 15 October 2012 (UTC)
 * Who knows? I tried to repair.  Thanks for pointing out the problem.  --Smokefoot (talk) 22:30, 15 October 2012 (UTC)

Rename to Phenol (molecule)
I propose renaming this article to Phenol (molecule). This is to avoid confusion with the class of organic compounds, phenols. You can see in What links here that a lot of the pages listed there actually refer to the group of molecules, not the phenol molecule itself. This is because many editors put this markup: ... the group of phenols

They intend to link to the phenols article, but instead end up linking to the phenol article, which is the wrong one.

Maybe a disambiguation page could also be created at Phenol? — Preceding unsigned comment added by Llightex (talk • contribs)
 * If the problem is that some incoming links point to the wrong article, the best solution is to fix the incoming links. The solution you suggest, renaming this article and making this title a disambiguation page, will just make the problem worse:  instead of some of the incoming links needing to be fixed, all of the incoming links will need to be fixed because they will all need to be disambiguated.  -- Ed (Edgar181) 21:28, 24 August 2014 (UTC)

External links modified
Hello fellow Wikipedians,

I have just added archive links to 1 one external link on Phenol. Please take a moment to review my edit. If necessary, add after the link to keep me from modifying it. Alternatively, you can add to keep me off the page altogether. I made the following changes:
 * Added archive https://web.archive.org/20120318234817/http://www.para-gen.com/paragen/publications.htm to http://www.para-gen.com/paragen/publications.htm

When you have finished reviewing my changes, please set the checked parameter below to true to let others know.

Cheers. —cyberbot II  Talk to my owner :Online 10:26, 27 August 2015 (UTC)

Experts: Ester-phenols in Reconquista River article?
The Reconquista River article mentions ester-phenol as a pollutant and links the second Alf of the word to this article.

Is this valid terminology? Is it an important distinction, ester-phenols vs. phenols? Or is it a typo and should be two separate terms? Thanks! Geekdiva (talk) 21:52, 30 April 2016 (UTC)

A simple chemistry question
Hi, this is the wrong place to ask this but I don't know where else, so any pointers would be welcome. I'm a programmer trying to learn chemistry. It says "[phenol can be produced by] direct oxidation of benzene with nitrous oxide, a potentially "green" process:" How come this reliably produces a *single* -OH stuck on the benzene ring, and not in various numbers scattered all over the ring? thanks 92.29.224.107 (talk) 19:43, 24 September 2017 (UTC)
 * Well you have almost answered your own question by posing so well. I am a chemist and I dont know the exact answer but I do know the two likely options: (1) Because that single OH communicates its presence throughout the rest of the molecule.  Chemists say that the first OH "deactivates" the ring toward further reaction with N2O. (2) one common way chemical engineers (people who implement chemistry) conduct reactions is at low conversion/high yield such that they convert only a few percent of the benzene to phenol, pull the phenol out of the mix, then recycle the benzene for another engagement with a small amount of N2O.  --Smokefoot (talk) 01:06, 25 September 2017 (UTC)
 * Both of those explanations make sense - thank you!

J. H. Kellogg
Should the application of carbolic acid endorsed by J.H. Kellogg (of the cereal) be mentioned under History on this page? 😖

Reference (for example): https://www.theatlantic.com/magazine/archive/2018/12/the-sex-recession/573949/ Henk Poley (talk) 16:51, 18 November 2018 (UTC)
 * It's not noteworthy in regards to the history of phenol. It's just trivia.  -- Ed (Edgar181) 19:36, 18 November 2018 (UTC)