Talk:Fluorocarbon

"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)

Movement of subsection
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)
 * I think the total article should be resorted, I will have a go. --Dirk Beetstra T  C 21:25, 20 June 2006 (UTC)
 * I like what you did there. Good job on being  bold.  I think that having the chemical properties before the preparations though is a better idea, so I'm just going to reorder that.  —Preceding unsigned comment added by Dawn Burn (talk • contribs)
 * Hi Dawn, thanks. Indeed, sometimes one has to be bold.  The article has improved a lot since I was there some days ago.  A little ordering and the addition of some (IMHO) missing sections should help to get this article to a higher status (I saw that Wim van Dorst assessed it this afternoon as 'start-class' ..  Your suggestion makes sense, that puts the chemical properties close to the biological role, which nicely fits together.  I'll leave you to it for now, I'll have a look, tomorrow!  See yu around!  --Dirk Beetstra T  C 22:08, 20 June 2006 (UTC)

Chemistry of Ozone Depletion
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)
 * Okay, I can't figure out how to link to the old version so learning that would be helpful, but I'm referring to the edit on June 22 by Mordacil.--Dawn Burn 03:34, 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)

Integrity and Accuracy of Article
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)
 * The significance of the carbon fluorine bond and the concept of fluorocarbons are closely related. I think it is a very narrow perspective to suggest that fluorinated pharmaceuticals are not fluorocarbons and I don't think it would be wise at all to remove the pharmaceutical content from this article.  Perhaps the article could benefit, though, from a clearer distinction between chemicals which derive most of their chemical properties from C-F bonds and those that derive fewer of their properties from C-F bonds.  -- Ed (Edgar181) 21:32, 2 November 2008 (UTC)
 * I maintain, from the secondary source, that pharmaceuticals are not fluorocarbons. Instead of your solution, I propose a short descriptive chemistry article on the carbon fluorine bond (with a section on its significance to pharmaceuticals and agrichemicals) and a separate page on altogether on fluorine chemistry/fluorocarbon chemistry - to get rid of the burdensome details average readers are subjected to at the bottom, and to provide space for mechanistic details significant to chemists. Thanks. -Shootbamboo (talk) 22:03, 2 November 2008 (UTC)
 * Thanks for checking, but I think that it would be unhelpful and even misleading to our readership to de-emphasize or semi-exclude C-F containing pharmaceuticals from this article. As indicated by the C&EN article, the chemistry profession is very proud of the F-containing pharmaceuticals.In fact I was planning to construct a table of C-F containing home-run drugs for this article. Pharmaceuticals are not fluorocarbons, but many fluorocarbons are pharmaceuticals.  You refer to David Lemal, who was a scholar in perfluorocarbons (he's the one that made C5(CF3)5-, I think).  Some perfluorocarbons are of medical significance as blood substitutes, but I dont know of any perfluorocarbon classifiable as a pharmaceutical. --Smokefoot (talk) 22:35, 2 November 2008 (UTC)
 * Okay, here's the word from on high: "Fluorocarbons: Compounds consisting wholly of fluorine and carbon." http://goldbook.iupac.org/F02459.html. We could consult the Wikichem group and aim for some consensus on an operational definition, since we have a perfluorocarbon, which IUPAC would view as redundant.--Smokefoot (talk) 22:44, 2 November 2008 (UTC)
 * Thanks for checking IUPAC on the definition of a fluorocarbon. I am behind Lemal's interpretation, and my previous proposals. I don't think there is problem of redundancy with the perfluorocarbon page and this page. I picture this page as functioning as a hub (like the fluoropolymer) page, except a much better one because this page actually describes the important characteristics/uses of the general classes. I think that is the best/most efficient use of this page for readers. -Shootbamboo (talk) 01:31, 3 November 2008 (UTC)
 * I think the IUPAC definition is reasonable, by analogy with terms such as hydrocarbon and oxocarbon. But, since there is already an article on perfluorocarbons, I don't think much needs to be changed here other than the title of the article. Perhaps fluorine-containing organic compound? Organofluorine chemistry? An article on the C-F bond would be interesting, but the title would suggest a narrower scope. --Itub (talk) 10:29, 4 November 2008 (UTC)
 * I agree with Itub that the article is generally okay. My main suggestion is that "fluorosurfactants" and "anesthetics" are applications, not functional classes based on chemical principles.  I tried to move these sections previously, but Shootbamboo reverted.  I support the proposal that Shootbamboo develop an article on the C-F bond.  I would be glad to help with that project.--Smokefoot (talk) 13:44, 4 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. 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. 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)


 * As someone with a personal subscription to JFC (and I run reactions with fluorocarbons!), I'd like to say I support the idea to remove things that do not meet the IUPAC definition. It is true that the definition has become blurred, because work on fluorous biphasic systems often use fluorine-rich compounds that are not true fluorocarbons.  I think Itub's suggestion of organofluorine chemistry (currently a redirect) is great - this is the true home for articles on fluorine-containing pharmaceuticals and the like.  It is ridiculous that organofluorine chemistry should redirect to fluorocarbon - it's as if the word organic chemistry was a redirect to hydrocarbon - the subject is SO much bigger than fluorocarbons alone. Walkerma (talk) 16:37, 7 November 2008 (UTC)
 * Walkerma, thanks for participating in the discussion. Please see my comments below under --Fluorocarbon definition for this page-- on why I find your view naive (and ultimately harmful) for Wikipedia. Thanks! -Shootbamboo (talk) 04:41, 8 November 2008 (UTC)

Fluorocarbon definition for this page
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)
 * Just to be clear, what is, according to you, the "commonly accepted working scientific definition of this term"? --Itub (talk) 06:47, 5 November 2008 (UTC)
 * Lemal, in the abstract, labels them as "organic molecules with carbon skeletons and fluorine "skins."" In the first sentence after the history section, he says "with fluorine "skins" covering the carbon skeletons, fluorocarbons differ dramatically from their hydrocarbon counterparts in properties and chemical behavior." If you would like a .pdf copy of the file, leave an email and I will send it to you when I can, I am looking at a hard copy now. Thanks. -Shootbamboo (talk) 01:47, 7 November 2008 (UTC)


 * Consensus not achieved. The fluorine component is essential to the efficacy of the many pharmaceuticals, so I really think that we need a strong discussion in this article about the significance of C-F-containing compounds as pharmaceuticals and in agriculture, in fact I think that these sections should be larger.  I am disappointed by Shootbamboo's persistence, but I cannot argue with the effectiveness of this approach.  I will be in only intermitent editing contact for a while, so enjoy the freedom to edit away.  It is editing approaches like yours that make Wikipedia an unpleasant experience, at least for me.--Smokefoot (talk) 13:44, 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.


 * Carbon-fluorine bond. Currently redirecting to fluorocarbon. Should be a relatively short article on the physical properties of the bond itself (bond lengths, dissociation energies, hybridizations, that type of stuff). Discussion of fluorine-containing compounds (including drugs) belongs in organofluorine chemistry (or organofluorine compound).
 * Organofluorine compound. Doesn't exist. Should redirect to or from organofluorine chemistry (see below).
 * Perfluorocarbon. Currently contains compounds containing C and F only. Note that this matches the IUPAC definition of fluorocarbon. It should be renamed to fluorocarbon and start from the IUPAC definition, but also mention the "Lemal definition" and say that the term is also used for many other organofluorine compounds where it is considered that their properties largely arise from their "fluorine skin" (vague as that is).
 * Fluorocarbon. Contains all sorts of organofluorine compounds, including "IUPAC-" and "non-IUPAC" fluorocarbons and drugs. Should be renamed to organofluorine compound or organofluorine chemistry. The section about the C-F bond could be summarized and the details split off and expanded into Carbon-fluorine bond.
 * Organofluorine chemistry. Currently redirects to fluorocarbon. Should instead contain what is currently in fluorocarbon or redirect to organofluorine compound.

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)


 * From the conversation here, it seems that there could be two separate articles. One being a general article about fluorinated organic compounds and the chemistry of the C-F bond (including discussions about pharmaceuticals, agriculturual chemicals, etc.) The second being a more specific article about fully flourinated organic compounds - whether this one should be titled "perfluorocarbon" or "fluorocarbon" doesn't matter too much to me (but since IUPAC uses fluorocarbon, that seems to be the way to go, contrary to my earlier statement above).  As it turns out, this is very close to the current situation.  We have one general article, located at fluorocarbon and one more specific article located at perfluorocarbon.  I suggest the following:  move fluorocarbon to organofluorine compound (or other suitable name, with appropriate redirects) then move perfluorocarbon to fluorocarbon.  This is close to what Itub suggests above, except that I would include the content he's suggesting to put in "Carbon-fluorine bond" in the one main article with other general information about flourine containing organic compounds.  -- Ed (Edgar181) 12:46, 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)
 * Fluorocarbon: As is - Colloquial fluorocarbons
 * Perfluorocarbon: As is - True IUPAC fluorocarbons (the prefix "per" is an effective mechanism of saying true fluorocarbon in my mind)
 * Carbon-fluorine bond: Should describe background, biological role, significance to fluorocarbons, pharm & agrichem (P&A). It seems shortsighted to not feature P&A content there, because editors will want to feature the benefits of the C-F bond to that page regardless of what we say. The fluorine chemistry page should be the place of more technical content.
 * Fluorine Chemistry: reactions featured at bottom of this article should be placed there.

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)
 * Thanks for contributing again. No problem. I think the fluorocarbon fishing line nails it though. Any regular person is going to type into google fluorocarbon. We should give them the best working scientific definition. I think Lemal does it beautifully (secondary source)! I'm sorry, but Itub is not a source for the fluorocarbon page, and he hasn't brought any important secondary sources to the discussion. (Are you guys buddies?) IUPAC is not a reference! Also see my chlorofluorocarbon point below. C'mon man you're so close to seeing the light! Call a spade a spade. Am I really going to have to waste my time to try and get other people to comment here to say a chlorofluorocarbon is a fluorocarbon? Be intellectually honest with us! Thanks! -Shootbamboo (talk) 15:50, 8 November 2008 (UTC)
 * IUPAC is not a reference? Huh? --19:23, 8 November 2008 (UTC)
 * Correct, IUPAC is not a reference currently cited as a source for the fluorocarbon page. -Shootbamboo (talk) 21:02, 8 November 2008 (UTC)
 * And that's a severe deficiency. It's like not citing the BIPM in the kilogram page (well, maybe not as bad, but still bad). --Itub (talk) 07:01, 9 November 2008 (UTC)
 * I am about to cite IUPAC, but I do so with a great measure of hesitancy, 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 the technical of the technical to the article. 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. -Shootbamboo (talk) 13:52, 9 November 2008 (UTC)

Classes of Fluorocarbons
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 with my edit here. 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)
 * Yes, I can help you understand my problem with the classification system that you continue to impose. Chemists typiically classify compounds based on their stoichiometry or on their structure (functional groups, aromatics, etc).  Many different structural or stoichiometric classes of compounds could be surfactants or lubricants or anesthetics, which are classifications based on some sort of application or property.  Sometimes chemicals are classified by applications or properties, but it is pretty strange to mix the two classification systems. --Smokefoot (talk) 13:44, 5 November 2008 (UTC)
 * Despite the length of your post, I don't think you talked specifics. Nevertheless, I renamed the section as Types to eliminate your concerns. -Shootbamboo (talk) 01:33, 7 November 2008 (UTC)

Picture
Picture removed due to non-fluorocarbon content. I would love for it to return without the pharmaceuticals.
 * I think it's unconstructive to start removing content from the article when there is ongoing discussion/disagreement about the scope of this article. -- Ed (Edgar181) 12:51, 7 November 2008 (UTC)
 * Thanks for keeping an eye out for constructive edits. I don't think I am trying to be "unconstructive" though. The thing that put a bad taste in my mouth was having the dispute template I applied removed, even after the disputed material was reapplied! I am relatively new, so if you could give me some background on etiquette (at my talk page) I would love to learn. Thanks. -Shootbamboo (talk) 03:48, 8 November 2008 (UTC)
 * It is quite plainly the wrong template, because no one has categorized this page under Category:Pharmaceuticals. For more information about what that means, see Categorization. I didn't replace it with a better template because I find those templates lame and unnecessary, but if you add one that at least makes sense I won't remove it. As for etiquette, the general convention is: 1) first reach a consensus; 2) then do major disputed edits to an article. So far the consensus doesn't seem to go your way; everyone else who has posted in this page disagrees with you. If you are interested in more information you can look at Dispute resolution. --Itub (talk) 05:17, 8 November 2008 (UTC)
 * Thank you for clearing up for me why the template was wrong. Better late than never. However, I sharply disagree. Pharmaceuticals are not fluorocarbons, and everyone, including you, agrees to that fact. Do you define the dispute differently? To circumvent these temporary concerns I will edit the Fluorocarbon page. Thanks. -Shootbamboo (talk) 06:37, 8 November 2008 (UTC)

Chlorofluorocarbons and Fluorocarbon fishing line
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)


 * Exactly. CFCs are fluorocarbons only when the term is used loosely (which of course is perfectly fine in some contexts). But strictly speaking, they are not fluorocarbons any more than amines are hydrocarbons or alcohols are oxocarbons. What you call "insane logic" is what I simply call logic, consistency, and following the recommendations of the most authoritative source regarding chemical nomenclature. --Itub (talk) 15:01, 8 November 2008 (UTC)
 * What is the role of an encyclopedia? According to your definition fluorocarbon fishing line is not a fluorocarbon. Don't stick your head in the IUPAC sand. What is the role of an encyclopedia? Thanks. -Shootbamboo (talk) 16:01, 8 November 2008 (UTC)


 * To inform accurately. It should start from a precise and authoritative definition and then go on to the loose uses, pointing the reader to another article if needed. --Itub (talk) 19:32, 8 November 2008 (UTC)
 * And Wikipedia attempts to inform accurately by using the principle of verifiability, which I have done on the page. Can you please elaborate on fluorocarbon fishing line? Thanks. -Shootbamboo (talk) 21:10, 8 November 2008 (UTC)


 * Like Walkerma replied in another thread, this can be included as an example of the looser use of the term. This is certainly not the first case of industry, marketing, or popular use deviating from more formal usage. Some examples: LSD is popularly called "acid" despite not being particularly acidic, maybe because acid is the only word in the name that people know how to pronounce; halogen lightbulbs are not made of halogen (although they do contain halogens); Liquidmetal is not really liquid; tin foil is usually not made out of tin; pencil lead is not made of lead; lead crystal is not exactly crystalline; tear gas is not a gas... --Itub (talk) 07:21, 9 November 2008 (UTC)
 * In an effort to reach consensus, I will modify the fluorocarbon page. -Shootbamboo (talk) 13:45, 9 November 2008 (UTC)

Confusion over biological role
In an attempt to unwind the harm (IMHO) caused by this edit this edit 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)

Unsourced material that appears misleading
I deleted this material "Prior to the Montreal Protocol, CFCs, such as Freon and chlorodifluoromethane were used as cleaning solvents." with this edit in an attempt to unwind the harm (IMHO) caused by this edit 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 so the statement was deleted, for being terribly naive(IMHO). Thanks. -Shootbamboo (talk) 17:07, 8 November 2008 (UTC)

Harmful and doubtful content
And again, with this harmful(IMHO) edit 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)
 * Many mono- and difluorinated organic compounds indeed behave physically like the corresponding hydrogen compounds. The impact of the C-F bond just is overwhelmed by the properties imparted by the rest of the molecular structure. Since this concept might be difficult to appreciate, I mentioned fluorouracil, whose physical properties seem pretty similar to uracil's.  Now in terms of reactivity, uracil and its 5-fluoro derivative are quite different - hence the breakthrough in pharmacology.  With regard to the definition business: I support Itub's proposed layout and distribution of material.  Here is my condensation of Itub's to-do list (setting aside the redirects).  Most editors think that the current article should remain rather broad, at least until the new articles have been constructed.

To-do list: --Smokefoot (talk) 19:25, 8 November 2008 (UTC)
 * Carbon-fluorine bond, a relatively short article on the physical properties of the bond itself ...
 * Perfluorocarbon. renamed to fluorocarbon ...properties largely arise from their "fluorine skin"...
 * Organofluorine chemistry. Contains all sorts of organofluorine compounds, including "IUPAC-" and "non-IUPAC" fluorocarbons and drugs...

Actions taken, Actions to be taken
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)
 * Carbon-fluorine bond a must, i agree a relatively short article
 * Fluorine chemistry Journal of Fluorine Chemistry anyone?
 * Perfluorocarbon - rewritten to include not just to include fluoroakanes, but also fluoroalkenes and fluoroalkynes.
 * Not quite what I thought we had agreed to:
 * 1) Carbon-fluorine bond. ... relatively short article...
 * 2) Perfluorocarbon. ... start from the IUPAC definition, but also mention the "Lemal definition" and say that the term is also used for many other organofluorine compounds where it is considered that their properties largely arise from their "fluorine skin"....
 * 3) Fluorocarbon. ...dhould be renamed to organofluorine compound... section about the C-F bond could be summarized and the details split off ...

I will try to do implement these changes. --Smokefoot (talk) 21:58, 8 November 2008 (UTC)
 * What did I agree to? -Shootbamboo (talk) 22:30, 8 November 2008 (UTC)
 * Not sure what you have agreed to, but Itub's proposal was favored by the rest of the editors, including Walkerma, who has more more experience in editing than all of us combined as well as being active in the field of organofluorine chemistry. Status report:
 * We now have a page on organofluorine chemistry, based on an early incarnation of fluorocarbon. It remains very rough because of all the jostling the past several days.
 * We soon will have a separate page on the carbon-fluorine bond.
 * What remains is a merger of the content in the current article on fluorocarbon and perfluorocarbon.--Smokefoot (talk) 22:44, 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)
 * Smokefoot and I are both looking ahead to work on the carbon-fluorine bond and organofluorine chemistry. I want to work on perfluorocarbon to get it to describe not only fluoroalkanes, but also fluoroalkenes and fluoroalkynes, which I indicated on its talk page. Thanks. -Shootbamboo (talk) 00:56, 9 November 2008 (UTC)
 * Actually, Smokefoot, I think you greatly undervalue your experience, and that and other WP:Chem members, all very experienced editors. At WP:Chem we have a very good tradition of mutual respect and working together to reach consensus.  My impression was that consensus was reached here.  I think that cordiality explains why most active editors remain active after two or more years - something quite rare on WP!  I was assuming that things like the fishing line would be dealt with as examples of the deviation from the "official" definition.  Sorry I can't participate in the writing, though I may be able to provide some pictures and some irritating comments. Cheers, Walkerma (talk) 03:18, 9 November 2008 (UTC)
 * Walkerma, are you honestly going on the record that it is responsible as an encyclopedia to treat fluorocarbon fishing line as not a fluorocarbon based upon an IUPAC definition of fluorocarbon that goes against the best secondary source for this article, keeping in mind that secondary sources (and not IUPAC) are the heart of Wikipedia/encyclopedias? Thanks. -Shootbamboo (talk) 12:29, 9 November 2008 (UTC)
 * Yes, I am; Wikipedia depends on authoritative references. I suspect that Lemal would be horrified to see his definition used as a means to undermine the IUPAC consensus (IUPAC definitions often take years of discussion between subject-experts). It is clear that the IUPAC definition carries much more weight.  Walkerma (talk) 02:47, 10 November 2008 (UTC)
 * Wow, have you read Lemal's article? It says things like "fluorcarbons serve as vascular implants, inhalation anesthetics". Have you seen the structure of an anesthtetic lately? They are ethers. Ethers contain oxygen. Why then would Lemal be horrified if he called them fluorocarbons? -Shootbamboo (talk) 03:01, 10 November 2008 (UTC)
 * Fair point - I read the article at the time, I only glanced over it yesterday, and medical uses are completely outside my area of interest. You are absolutely right that in that sentence he refers to partially fluorinated compounds as "fluorocarbons".  I do note, though, that in the following paragraph he refers to HFCs as "fluorocarbon derivatives" and he uses phrases like "fluorocarbons and derived substances" and "highly fluorinated polymers".  But you're right, he wouldn't be "horrified". Walkerma (talk) 05:30, 10 November 2008 (UTC)
 * Walkerma, you make good points, I have also been thinking about how Lemal referred to HFCs as fluorocarbon derivatives, while he also referred to anesthetics as fluorocarbons and how that should/could be incorporated into the page layout. Thanks. -Shootbamboo (talk) 03:43, 11 November 2008 (UTC)
 * Also, a website selling fishing line is not an authoritive source on a chemical definition, any more than this site should be used to define anion. Walkerma (talk) 02:50, 10 November 2008 (UTC)
 * What we are calling the "IUPAC definition" is just as secondary as yours; it was also published in a journal article. But it has the additional advantage that it was an article about nomenclature, published by people specializing in nomenclature, as opposed to a vague definition given in passing in a chemistry article. --Itub (talk) 12:31, 9 November 2008 (UTC)
 * In an effort to reach consensus, I will modify the fluorocarbon page. -Shootbamboo (talk) 13:45, 9 November 2008 (UTC)

IUPAC Definition
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)
 * Your understanding is wrong. Technical articles are not supposed to be "non-technical". Yes, they should be as accessible as possible, but never at the expense of accuracy and completeness. --Itub (talk) 17:27, 9 November 2008 (UTC)
 * By the way, how is IUPAC's definition "too technical"? It's not as if they defined fluorocarbons in terms of relativistic quantum mechanics. If anything, their definition is easier to follow because it is clear and unambiguous. In case anyone is interested, here is the definition given by the Oxford Dictionary of Chemistry, another respected tertiary (or however you want to count it) source: "Compounds obtained by replacing the hydrogen atoms of hydrocarbons by fluorine atoms. Their inertness and high stability to temperature make them suitable for a variety of uses as oils, polymers, etc. See also chlorofluorocarbon, halon." --Itub (talk) 11:02, 10 November 2008 (UTC)
 * My concern is that editors would want to use the IUPAC definition only. IUPAC is a tertiary source from chemists on high, and while they are important, their definition is not used in common life (fluorocarbon fishing line). My impression is that Wikipedia is written for people who come at things from a common life perspective. I think we have a unique perspective on IUPAC because we are chemists. If Joe the Plumber buys fishing line that says fluorocarbon he might type that into google. Joe doesn't care if some highly organized chemists have defined fluorocarbon in a way that makes his fluorocarbon fishing line non-fluorocarbon (to him that is over-technical). Sure, to us it is amazingly simple:all carbon and fluorine. But to him that is senseless. His package says fluorocarbon. So I have been obstinate in fighting for the general definition, because that is how it is used in reliable secondary sources (Lemal). (But not without a degree of complexity, as Walkerma has noted above, and I have been wrestling with that). Thanks. -Shootbamboo (talk) 03:54, 11 November 2008 (UTC)
 * I decided to search for books mentioning fluorocarbon fishing lines because honestly I had never heard about them. Curious result: I rapidly found dozens of books about fishing that mention it, but none about chemistry. What does that indicate? In my opinion, only fishermen and the people who market the product call it that way (maybe they decided that the chemical terms were too difficult to pronounce). But this is a chemistry article, not a fishing article. But I should emphasize that in any case the fishermen could readily find their polymers anyway under my proposal. I've never said we should completely exclude all mention of HFCs and other "non-IUPAC" fluorocarbons from this article; only that they should be moved to a broader article and the reader referred there. Something roughly equivalent to "Fluorocarbons are compounds made of C and F.[IUPAC, Oxford, etc.] Broader definitions also include 'highly fluorinated' compounds even if they contain other elements because they derive their unique properties from their 'F skin'.[Lemal] See organofluorine compound for more types of compounds that may fall under the broader definition. Some examples of compounds falling under the broader definition include anesthetics, fluoropolymers such as those used in fluorocarbon fishing lines, surfactants, etc."
 * I'm sorry if Joe doesn't care about scientific standards and organizations, but we should, as authors of an encyclopedia that attempts to be respectable. It's the same story with the planet article; Joe probably doesn't care either, but the authoritative definition, the one that is given greatest weight, is the one from the International Astronomical Union. --Itub (talk) 06:40, 11 November 2008 (UTC)

Definition
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)
 * I agree in principle with Itub's proposal and with all the experienced chemists which have commented on this page that fluorocarbon should follow a strict definition per IUPAC, per analogy to hydrocarbon, and per common sense. Looser definitions should refer to organofluorine and/or perfluorocarbon (the latter including polyfluorinated compounds per cited 60% rule; maybe creating something like polyfluorinated compound). What is the problem with that and why do we need all this drama? What a waste of time and bytes :-( Cacycle (talk) 23:59, 11 November 2008 (UTC)
 * I agree too, in principle, to allow this page to have the IUPAC definition. I have opposed it in practice (from the look of the perfluorocarbon page) and because editors seemed obstinate in lump everything else into the organofluorine chemistry page, while arguing the organofluorine page is unnecessary. I propose the term Polyfluorochemicals to get all the other "fluorocarbons" that aren't IUPAC fluorocarbons, and I see the page perfluorocarbon as ultimately as pointless and only a redirect to fluorocarbon. Thanks. -Shootbamboo (talk) 00:20, 12 November 2008 (UTC)

Contradiction
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)
 * Absolutely right, I'll clean up those leftovers now, and label non-fluorocarbons as fluorocarbon derivatives. Thanks. -Shootbamboo (talk) 00:22, 13 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)

Health and Environmental section - needs improvement
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)

Some issues
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)

This reaction seems wrong to me. Is it?

 * 2 N(C6H13)3 + 90 HF →  6 C6F14 + 2 NF3 + 81 H2

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)

Merger proposal
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 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)
 * Closing, given opposition and lack of support over 23 months. Klbrain (talk) 15:34, 3 January 2018 (UTC)

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perfluoro-neopentane
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)
 * ACD/Labs Percepta predicts a boiling point of 39.5±8.0 °C at 760 mmHg for perfluoroneopentane. --Leyo 09:09, 1 February 2021 (UTC)

And for mere mortals that means?
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)
 * Well it is a technical subject but I agree that the intro is too focused on nomenclature. That aspect can be addressed but you're still stuck with a hard-core chemistry article.  --Smokefoot (talk) 18:07, 24 September 2022 (UTC)

"Deoxofluorinating agent" listed at Redirects for discussion
The redirect [//en.wikipedia.org/w/index.php?title=Deoxofluorinating_agent&redirect=no 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  until a consensus is reached. Mdewman6 (talk) 23:39, 26 May 2023 (UTC)