Talk:Fluorocarbon

message: "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)

message: 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)
replies: text: 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)
thread_title:  Chemistry of Ozone Depletion 

message: 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)
replies: text: 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)
replies: text: 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)
replies: text: 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)
replies: text: 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)
replies: text: 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)
replies: text: 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)
replies: text: 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)

text: 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)
replies: text: 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)
thread_title:  Integrity and Accuracy of Article 

message: 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)
replies: text: 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)
replies: text: 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)

text: 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)

text: 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)

text: 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)
replies: text: IUPAC is not a reference? Huh? --19:23, 8 November 2008 (UTC)
replies: text: Correct, IUPAC is not a reference currently cited as a source for the fluorocarbon page. -Shootbamboo (talk) 21:02, 8 November 2008 (UTC)
replies: text: 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)
replies: text: 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)
thread_title: Fluorocarbon definition for this page

message: 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)
replies: text: 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)
replies: text: 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)
thread_title: Classes of Fluorocarbons

message: 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)
replies: text: 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)
replies: text: 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 Wikipedia: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 Wikipedia:Dispute resolution. --Itub (talk) 05:17, 8 November 2008 (UTC)
replies: text: 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)
thread_title: Picture

message: 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)
replies: text: 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)
replies: text: 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)
replies: text: 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)
replies: text: 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)
replies: text: 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)
replies: text: In an effort to reach consensus, I will modify the fluorocarbon page. -Shootbamboo (talk) 13:45, 9 November 2008 (UTC)
thread_title: Chlorofluorocarbons and Fluorocarbon fishing line

message: 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)
thread_title: Confusion over biological role

message: 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)
thread_title: Unsourced material that appears misleading

message: 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)
replies: text: 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:
*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...
--Smokefoot (talk) 19:25, 8 November 2008 (UTC)
thread_title: Harmful and doubtful content

message: 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)
replies: text: 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)
replies: text: 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)
thread_title: Definition

message: 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 .  --Dirk Beetstra T C 15:39, 12 November 2008 (UTC)
replies: text: 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)
thread_title:  Contradiction 

message: 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)
thread_title:  Health and Environmental section - needs improvement 

message: 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)
thread_title:  Some issues 

message: :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)
thread_title:  This reaction seems wrong to me. Is it? 

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

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thread_title:  External links modified 

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thread_title:  External links modified 

message: 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)
replies: text: 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)
thread_title:  perfluoro-neopentane 

message: 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)
replies: text: 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)
thread_title:  And for mere mortals that means? 

message: 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  until a consensus is reached.  Mdewman6 (talk) 23:39, 26 May 2023 (UTC)
thread_title:  "[[:Deoxofluorinating agent]]" listed at [[Wikipedia:Redirects for discussion|Redirects for discussion]]