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"Fluorocarbons are polymers" - in first paragraph - surely this is incorrect - things like PTFE are polymers, but hexafluoroethane for example, is not a polymer! Unless I'm missing something obvious, this should be changed.
86.17.152.192 15:45, 8 April 2006 (UTC)
Personally, I think most people who look up Flurocarbons are not going to be wanting the chemical preparations right off the bat. I think that moving that subsection to the bottom (before references) would increase accessibility and readability. Thoughts? -- Dawn Burn 20:49, 20 June 2006 (UTC)
Smokefoot reverted the edits on pollution saying that the chemistry was unsound. Since it was drawn from the reference article, falls in line with what I recall, and is also supported by Ozone depletion, I'm curious as to why the chemistry is not sound. -- Dawn Burn 03:29, 24 June 2006 (UTC)
Here's my thinking. The contracted section by Mordacil described incorrect chemistry (unbalanced equations for starters, and slang) and the topic is authoritatively covered in ozone depletion, a link to which I included. Also the present article already mentioned CFC's, which again (conveniently using balanced equations even) describes the reactions relevant to ozone depletion). The present report is not about CFC's, per se. Otherwise do we want to expand each subsection that touches on an ancillary topic, probably doing so would make the report unwieldy, weakening the impact. IMHO. Also more glaring gaps exist still in this report than rehashing material already twice described elsewhere. Underdeveloped topics: pharmacology, methods to introduce C-F bonds remains underdeveloped. For the environmetal enthusiast, under "Pollution effects"- what is the biochemistry underpinning the concerns about the persistency of fluorocarbons?-- Smokefoot 03:46, 24 June 2006 (UTC)
Overall, the integrity of this article has been compromised by confusing the significance of the carbon-fluorine bond in fluorine chemistry with the concept of fluorocarbons. Specifically, PHARMACEUTICALS ARE NOT FLUOROCARBONS - Lemal 2004 Perspective on Fluorocarbon Chemistry: "Fluorine is present in a large and ever increasing number of pharmaceuticals and agrichemicals, typically as an occasional fluoro or trifluoromethyl substituent on a hydrocarbon derived molecule. Devoted as it is to fluorocarbons, the present paper does not deal with this very important aspect of fluorine chemistry." Fluorocarbons, by contrast, have there physio/chemical properties altered when compared to hydrocarbons, as Lemal states, "fluorocarbons are remarkably volatile" and "low surface energies are the reason that fluorocarbon-based textile and carpet finishes are both oil and water repellent, that fluorocarbon-based fire fighting foams spread easily over the surface of a burning hydrocarbon liquid." The pharmaceutical content must be excised. Can someone change the picture to exclude pictures H&I? Thanks. - Shootbamboo ( talk) 21:03, 2 November 2008 (UTC)
Notice how far we are from the original dispute template I put up (which was taken down before the dispute was resolved, in my mind). That doesn't seem right, but I'm new to this, could someone clear up that policy for me? Basically from everyone's discussion, I was correct in applying it, pharmaceuticals are not fluorocarbons, therefore I will be putting the pharmaceutical content under my post here, in anticipation for (IMHO) the C-F bond page. I also plan on starting a new talk section for the editors who could only shift the debate from my original dispute instead of addressing it. Thanks. - Shootbamboo ( talk) 00:19, 5 November 2008 (UTC)
--Pharmaceuticals and Agrichemicals-- The carbon-fluorine bond are commonly found in pharmaceuticals and agrichemicals because it is generally metabolically stable and fluorine acts as a bioisostere of the hydrogen atom. An estimated one fifth of pharmaceuticals contain fluorine, including several of the top drugs. [1] Examples include 5-fluorouracil, fluoxetine (Prozac), paroxetine (Paxil), ciprofloxacin (Cipro), mefloquine, and fluconazole.
--Biological role-- Despite thousands of naturally-occurring organic compounds containing chlorine and bromine, there are only a handful of natural fluorocarbons. [2] They have been found in microorganisms and plants, but not animals. The most common natural fluorocarbon is fluoroacetic acid, a potent toxin found in a few species of plants. Others included ω-fluoro fatty acids, fluoroacetone, and 2-fluorocitrate which are all believed to be biosynthesized from fluoroacetic acid. Content moved from Fluorocarbon page. - Shootbamboo ( talk) 00:25, 5 November 2008 (UTC)
Someone above in "Integrity..." has suggested that this page be renamed. I vehemently disagree. I find such a suggestion dangerous, and an attack on the commonly used definition of fluorocarbons - see Lemal's application of the term - secondary source - above. I think proponents of this stance would simply cite the IUPAC definition in such a closed minded way (which, strikingly, editors knee-jerked for the most liberal interpretation at first [IMHO]) that it destroys the commonly accepted working scientific definition of this term. While IUPAC is instructive, encyclopedias are not written based simply on technical definitions. Lemal provides the commonly used definition from his application of the word. Thanks. - Shootbamboo ( talk) 00:47, 5 November 2008 (UTC)
I had already read the article, thanks. Yet I have a number of concerns: 1) this is not the only paper on fluorocarbons ever published. I'm sure others use slightly different definitions. How much fluorine do you need to have a "skin"? Most of the examples in the paper are perfluorinated compounds, but he also discusses many partially fluorinated cases and even some monofluorinated hydrocarbons. The line is blurry; it is like distinguishing an "organic" compound from an "inorganic" compound (i.e., a combination of "I know it when I see it" with a waste of time). 2) The fact that he didn't include drugs could also be interpreted as an easy way of narrowing the scope of the paper, rather than a categorical definition of what fluorocarbons are. However, I agree that drugs are not usually called fluorocarbons, in my opinion because there are so many things going on in the usual drug molecule (with many other functional groups and stereochemistry present) and the fluorine atom(s) are generally only behind a relatively small part of the function of the molecule. 3) Yet, my most important concern, we still haven't agreed what the scope and title of this article should be. There are basically two approaches: narrow the scope, or broaden the title. But to make things clear we need to consider all the articles involved. I'm going to list them below along with a brief description of what they "currently" contain (at least before your latest changes to this articled) and what I think they should contain. I would appreciate if y'all could write a similar list so we can be on the same page.
Hope this helps. In the meantime there is still no consensus to delete stuff from this article so I will revert the deletion again. Cheers, Itub ( talk) 05:52, 7 November 2008 (UTC)
I strongly disagree. I strongly support the definition of fluorocarbon to that commonly used by chemists because secondary sources are the heart of Wikipedia. Again, I find it irresponsible to hold on to the IUPAC definition, because average readers don't care about IUPAC definitions. Itub, see my recent page edits for an explanation of why (basically) I had removed the content previously. And thank you for the time you spent spelling out your ideas for the future of many pages. Here is my vison:
Itub, thanks for offering a "grandview" place to start for this discussion. However, I think your approach makes a something out of nothing ("skin" "issue"). Overall, I think my plan is more efficient, in that it will be easier to carry out by editors, and more readable for everyone. Imagine someone who was purchasing fluorocarbon fishing line. If they want to see what fluorocarbon is, I think the page in its current state (minus the details at the bottom) is constructed with them in mind. Which, isn't that what Wikipedia is for? While IUPAC definitions are instructive, I do not believe encyclopedias are meant to be stomping grounds for Chemists holding on to IUPAC definitions. Thanks! - Shootbamboo ( talk) 03:38, 8 November 2008 (UTC)
Support Itub's proposal. I think this strikes a nice balance. Firstly, let me apologise that I'm too busy to get into this discussion too deeply, so I haven't read everything involved in detail, though I did read over Lemal's perspective again before commenting. This also explains my (rather pompous sounding) "drive-by" comment above, I was running from one meeting to another. I think we need to use the IUPAC definition as the starting point, then perhaps comment how things have grown from there. I think that at one time the IUPAC definition was easier to work with - perfluorinated compounds were made by complete fluorination of hydrocarbons, and highly-but-not-fully fluorinated compounds were not common. Nowadays we have functionalised highly fluorinated compounds used for fluorous biphasic systems - often invoking the "60% rule" (you need 60% by mass F to dissolve preferentially in a fluorous solvent). Also, due to the environmental concerns about pure fluorocarbons, we now have environmentally friendlier things like hydrofluorocarbons (DuPont?), perfluoroketones (from 3M) and perfluoropolyethers such as Galden (Ausimont)., and these things have much in common with simple fluorocarbons. For example - perfluoro-N-methylmorpholine, which I use, has essentially no basic properties, and to all intents and purposes it behaves in the lab rather like perfluoro(methylcyclohexane). We also have poly-HFCs used for "fluorocarbon" fishing line. So I fully understand how terms can be blurred, but it's also wrong just to dismiss the IUPAC definition completely. Itub's approach does this beautifully, and it clarifies things nicely, separating non fluorocarbon content into a separate article. Shoving an entire class of compounds under the "C-F bond" article seems wrong; the bonding article should be able to focus on bonding - the structure, properties and effects of the C-F bond, not on compounds that happen to contain C-F bonds. However, I'd like to hear other opinions on this subject, I'll ask around. Shootbamboo, thanks for getting this debate going - I confess, I wanted to discuss the scope of our organofluorine articles for a while, and instead I buried my head in the sand! Walkerma ( talk) 09:20, 8 November 2008 (UTC)
Smokefoot, can you help me understand your problem with fluorosurfactants being labeled as a class of fluorocarbons because of a lack of "chemical principles." I have already tried to address your concern regarding chemical principles - where you first expressed them as structure and stoichiometry [1] with my edit here [2]. I specified the structure/function relationship, "fluorosurfactants have a polyfluorinated "tail" and a hydrophilic "head" and they are potent surfactants because they concentrate at the liquid-air interface due to their lipophobicity." Yet you continue the argument? Are you taking the POV that physical properties are not the result of chemistry? I think you may have a point to make, but at this point I can't see anything productive. - Shootbamboo ( talk) 01:11, 5 November 2008 (UTC)
Picture removed due to non-fluorocarbon content. I would love for it to return without the pharmaceuticals.
I just wanted to point out the name of Chlorofluorocarbons. Chlorofluorocarbons. Fluorocarbons. Fluorocarbons. What is motivating this insane logic that seeks to reclassify a chlorofluorocarbon as not a fluorocarbon? And why is it so deep and entrenched in Wikipedia editors with chemistry backgrounds? Thanks! - Shootbamboo ( talk) 14:51, 8 November 2008 (UTC)
In an attempt to unwind the harm (IMHO) caused by this edit [3] this edit [4] was performed because the section lead in sentence was not specific about the real point of intellectual curiosity the authors are after - Here it is, from Murphy 2003 "fluorine cannot be incorporated into organic compounds via the haloperoxidase reaction (Neidleman and Geigert, 1986) since the redox potential required for the oxidation of fluoride is much greater than that generated by the reduction of hydrogen peroxide. Therefore the mechanism by which C–F bonds are formed biologically is of considerable interest." Thanks. - Shootbamboo ( talk) 16:43, 8 November 2008 (UTC)
I deleted this material "Prior to the Montreal Protocol, CFCs, such as Freon and chlorodifluoromethane were used as cleaning solvents." with this edit [5] in an attempt to unwind the harm (IMHO) caused by this edit [6] because the sentence implies (without sourcing) that CFCs are not used as solvents anymore. However, here is a secondary source showing evidence for black markets for CFCs [7] so the statement was deleted, for being terribly naive(IMHO). Thanks. - Shootbamboo ( talk) 17:07, 8 November 2008 (UTC)
And again, with this harmful(IMHO) edit [8] the idea was put forth that fluorocarbons can behave very similarly to hydrocarbons. "Flurocarbons with fewer C-F bonds behave very similarly to hydrocarbons..." I find this statement unsourced, harmful, and doubtful: thus up for deletion. Fluorocarbons are distinguished (in the secondary source) by their sharp physical/chemical properties when compared to hydrocarbons. I would also point this rogue(IMHO) editor to the above IUPAC definition of fluorocarbons that other editors are currently arguing for. No-one on this talk page would agree that "fluorocarbons...behave very similarly to hydrocarbons." Considering it was the same editor who cited the IUPAC definition who made this statement... I can't help but be disappointed by these juxtaposed contributions. Thanks. - Shootbamboo ( talk) 18:33, 8 November 2008 (UTC)
To-do list:
-- Smokefoot ( talk) 19:25, 8 November 2008 (UTC)
I just created an organofluorine page, because everyone can agree on the definition of it, so it can be broad.
Thanks. - Shootbamboo ( talk) 20:32, 8 November 2008 (UTC)
I will try to do implement these changes. -- Smokefoot ( talk) 21:58, 8 November 2008 (UTC)
Itub still hasn't answered a basic question to elaborate on fluorocarbon fishing line. Editors on this page have not even agreed to the working definition of fluorocarbon (despite a definition provided by a reliable secondary source). How then can you say a merger of content is appropriate? - Shootbamboo ( talk) 23:23, 8 November 2008 (UTC)
As I indicated above, I am about to made a good faith effort to reach consensus by modifying the fluorocarbon page by inserting the IUPAC definition. I am very hesitant to do so, because from my understanding, Wikipedia articles that deal with technical content are supposed to remain approachable and non-technical, and I find inserting IUPAC only adds to the technical of the technical to the article. I also want to warn all editors involved, that I will resist any effort to subsume to perfluorocarbon page into the fluorocarbon page, as the term perfluorocarbon is the common term for true IUPAC fluorocarbons. I am also (pessimistically) concerned that my IUPAC definition edit is simply being used as a trap that unleashes a bad faith swath of editing, (subsuming perfluorocarbon content, etc.) If that is the case, I am afraid I will no longer see the wisdom of inserting this technical content. Also, I am passionate about the necessity of the short organofluorine article, that draws the distinction between pharmaceuticals and fluorocarbons. My edits have probably inflamed tensions. I understand this debate here has become passionate, and I hope we can work towards good faith consensus. I will be making this edit in good faith, and I hope to be pleasantly surprised later today, with good faith from other editors as I will leaving the computer for a great deal of time today. I also intend to contribute to the carbon-fluorine bond page in short order, which I also find essential. Thank you everyone. - Shootbamboo ( talk) 14:29, 9 November 2008 (UTC)
POV issues being raised over definition. To make my position clear (edit did it poorly), I don't think the manufacturers consulted Lemal to define their product, it is "the" definition, not one isolated source. - Shootbamboo ( talk) 03:33, 10 November 2008 (UTC)
OK, the first sentence of the head says "Fluorocarbons are organofluorines that contain only carbon and fluorine." (underline added). Then later in the article there is mentioning of chlorofluorocarbons, (CFClCF2)n polymer, and some other compounds which also contain C-Cl, C=O, etc. bonds. That seems like a clear contradiction to me, and hence I have tagged this article with {{ contradict}}. -- Dirk Beetstra T C 15:39, 12 November 2008 (UTC)
++++ Clarification +++++
I am an environmental chemist and am in the process of identifying which perfluorinated compounds and which fluorinated compounds need to be considered as potential contaminants to groundwater in my case. I think you have to think of these definitions in terms of what you learned years ago in math or logic where you compared two sets of numbers.
In our case instead of sorting even and odd numbers we are sorting compounds by their traits.
Perfluorinated compounds have carbons that are "saturated" with fluorine atoms. What this means is that every bond except those used to bind the carbon to another carbon or element that holds the carbon chain together are used to bind that carbon to fluorine atoms. The example given in my old Organic Chemistry text (Kemp and Velaccio) uses the following compound to explain this. Perfluoro tertbutyl bromide
CF3 | CF3 - C - H | CF3
C = a carbon atom, F = a fluorine atom, Br = bromine atom.
Perfluoro means that each of the carbons bound to fluorine have 3 fluorines bound to them (hence CF3) since they only have one bond to another carbon (if they had a carbon to carbon double bond or were bonded to two carbons they would only be able to bond to two fluorines, but would still be refered to as perfluoro). The perfluoro name is used for a "functional group" or a building block in chemistry. If you think of this compound as a bunch of legos and the CF3 group was one kind of lego and the bromide (Br) was another, you could replace one of the perfluoro groups on this compound, but it would still be called a perfluorinated compound because it included the perfluoro functional group.
Perfluoro tert buyl bromide is more broadly defined as an organofluorine compound as well as a fluorine compound. The difference between these last two definitions is that organofluorine compounds include compounds with not just perfluoro functional groups, but also compounds that only have one or two fluorines in the whole compound. Fluorine compounds is even broader a definition that includes inorganic fluorine compounds like stanous fluoride what we use to treat our teeth.
What I am getting at is that the terms you use to discuss these compounds is important. It is important to understand which class of compounds we are talking about. If we don't define exactly what we are talking about we will be confused about the issues. Not all fluorine compounds are created equal, and not all of them will be as toxic as a result.
amac1962 —Preceding unsigned comment added by 65.249.41.17 ( talk) 19:18, 22 January 2009 (UTC)
After reading the article, I don't feel the Environmental section has adequate references. For example, fluorocarbons are mentioned as being a greenhouse gas, but if it is a greenhouse gas, then shouldn't there be a Kyoto-style Global warming potential associated with it?
How are the environmental effects of fluorocarbons comparable to CFCs?
rhyre ( talk) 13:36, 27 December 2009 (UTC)
This page has a number of issues that I intend to address. Firstly, fluorocarbons are not ozone depletors, as they do not contain chlorine or bromine (as the linked page says!). They do not bioaccumulate - that is fluorosurfacts, another class of compounds.
The manufacture section needs to go with the perfluoroalkanes section, as it relates specifically to them. The example images ned to go inside the relevant sections.
Probably needs something about aluminum smelting. Links to pages about specific compounds and uses (eg Liquid breathing). F2Andy ( talk) 14:51, 16 May 2014 (UTC)
I have updated the page significantly, collecting all the bits about perfluoroalkanes together, and adding an applications sections. For the health and environment, I have added refs showing they do not bioaccumulate or ozone deplete.
I removed all references to non-fluorocarbons, including the section of fluoropolymers (some fluoropolymers are fluorocarbons, most are not, and there was already a bit about PTFE under perfluoroalkenes).
This leaves the perfluoroalkenes and perfluoroalkynes section a bit bare, but it is not an area I know. Also it includes hexafluorobenzene, which is not a perfluoroalkenes and perfluoroalkynes, and technically should be in a perfluoroaromatic section. F2Andy ( talk) 12:56, 19 May 2014 (UTC)
Number of hydrogen atoms on the left side is 13 * 3 * 2 + 90 = 78 + 90 = 168. But there are only 81 * 2 = 162 hydrogen atoms on the right side. — Preceding unsigned comment added by Ersagun ( talk • contribs) 15:00, 29 September 2015 (UTC)
There is a huge overlap in the content of this page and that of Perfluorinated compound. The disambiguation page PFC lists both, which puzzles this reader. I don't know which is the better title to preserve (making the other a redirect), but I hope that discussion can occur in just one place, so I suggest Talk:Perfluorinated compound#Merger proposal as that place. Sminthopsis84 ( talk) 12:53, 6 February 2016 (UTC)
I disagree. Fluorocarbons contain only carbon and fluorine, perfluorinated compounds contain other elements too (and the first paragraph of each page makes this clear, as far as I can see). The latter are organised in section 2 by their functional group. Fluorocarbons are special because they have no functional group. F2Andy ( talk) 08:52, 11 August 2016 (UTC)
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Is this compound known to be liquid or solid at standard conditions? I wonder because I would expect it to be gaseous, but the article explicitly states that there are only five gaseous perfluorocarbons, not including this one.
It seems to be a more obscure compound than the other small-chain perfluorocarbons, and I haven't found any information about its physical properties as of now. But since the boiling points of most perfluoroalkanes are very close to those of their respective parent hydrocarbon, I would have expected C(CF3)4 to be gaseous at STP, like neopentane. -- 91.15.31.233 ( talk) 00:11, 1 February 2021 (UTC)
Two sentences into the introduction and it goes ”Compounds with the prefix perfluoro- are hydrocarbons, including those with heteroatoms, wherein all C-H bonds have been replaced by C-F bonds.“ Sorry what? I came here to learn about my guitar strings. Perhaps someone can write a few sections that don’t require a degree in chemistry to understand. 2001:9E8:4619:3400:54B5:CCD4:7815:2528 ( talk) 09:37, 24 September 2022 (UTC)
The redirect
Deoxofluorinating agent has been listed at
redirects for discussion to determine whether its use and function meets the
redirect guidelines. Readers of this page are welcome to comment on this redirect at
Wikipedia:Redirects for discussion/Log/2023 May 26 § Deoxofluorinating agent until a consensus is reached.
Mdewman6 (
talk)
23:39, 26 May 2023 (UTC)
Is there a reason this massive area of concern regarding perfluoroalkyls is completely missing? Jonny36 ( talk) 18:38, 27 July 2024 (UTC)