Talk:Ionic liquid/Archive 1

Sense?
"Some salts are liquid at or below room temperature. Examples include pyridinium chloride, C5H6N+·Cl− that melts at 144.5 °C (292.1 °F)" When did 144.5°C become room temperature? -Dvrvm (talk) 06:41, 12 July 2010 (UTC)

Temperature in the Definition of ILs
In various contributions we have seen a variety of contributors indicating "ILs are only ILs at T < 100 C, or, at "room-temperature". It should be made known that this notion arises from at least two primary origins, with each being completely arbitrary.

The first comes from an introduction from Wilkes in the Welton and Wasserscheid edited book (2002), "Ionic Liquids in Synthesis". The use of T < 100 C was admittedly arbitrary, and put into use merely for service to the piece, in order to limit the discussion. Here is a direct quote from Wilkes' introduction (page 1),

"For purposes of discussion in this volume we will define ionic liquids as salts with a melting temperature below the boiling point of water. That is an arbitrary definition based on temperature, and says little about the composition of the materials themselves, except that they are completely ionic.  In reality, most ionic liquids in the literature that meet our present definition are also liquids at room temperature...".

The second source is largely due to Seddon and followers. QUILL has pushed/marketed this use of temperature in the definition to avoid having to include the rather large scope of work based on more than 150 years of "molten salts" research and therefore to appear as having created novel science, thereby ignoring previous literature precedent.

There is clearly no bona fide reason to include "temperature" in any definition of "ionic liquid". Some liquid salts form glasses, others form crystals with well defined melting points (as is the case for numerous molten salts). We would never consider making some arbitrary cut-off temperature for molecular liquids, under which we have a molecular liquid and over which we have ???, so please don't do this for ionic fluids, molten salts or "ionic liquids"! Liquid molten salts are just as ionic (and often even more ionic) than many of the glass forming modern liquid salts. —Preceding unsigned comment added by Kenisadick (talk • contribs) 12:47, 4 August 2009 (UTC)

Something wrong
The history page claims "ethanolamonium nitrate" (is it misspelled ethylamonium, or is it something different?) has a melting point of 52-55C. Later it shows the structure of ethylamonium nitrate, claiming its melting point to be 12C, but on the ethylamonium nitrate page it is given as 34C.

Something is not right. —Preceding unsigned comment added by 130.225.100.170 (talk) 09:57, 31 March 2008 (UTC)

Ethanolammonium nitrate is only the first ionic liquid found. I think only the confusion is in the melting point of ethyl ammonium nitrate. But both are different compounds —Preceding unsigned comment added by 203.199.205.25 (talk) 07:26, 5 April 2009 (UTC)

Ethanolammonium nitrate is 2-hydroxyethylammonium nitrate, which as pointed out above, is not ethylammonium nitrate. —Preceding unsigned comment added by Kenisadick (talk • contribs) 17:03, 7 July 2009 (UTC)

Bio Ionic
Someone must do a Wikipedia article on Bio Ionic.

added
I've added two paragraphs - one on solubility and one on exceptions to the generally accepted behaviour of ionic liquids. In order to fit these paragraphs into the text I have also made some, in my opinion, minor changes to the existing text. Hopefully I haven't made too much of a mess, but I'd appreciate if someone would check it.

I also feel that the list over "Leading" (now "Major") academic groups is somewhat biased towards research groups in English-speaking countries, which in fairness may be due to Seddon's influence. I would like this to be addressed in the future, with the inclusion of Héléne Olivier-Bourbigou and nobel laureate Yves Chauvin, as well as possibly some of the Chinese groups that are beginning to make themselves known. --Caohlin 04:07, 26 February 2006 (UTC)

Use in chemical demulsifiers is not mentioned
Ionic Liquids have another important application in the field of Demulsifying Agents used in the petroleum industry to break the salt water and crude oil emulsions. As oil fields mature, it is expected that the quantity of produced water will increase further, and heavier oils tend to form stronger emulsions. IL's will play an important role in advanced, molecularly designed demulsifiers. Amclaussen.

deleted
The "Suppliers" have been deleted, because there is absolutely now value. It's not clear if these ads are paid or not. Or we may list "Suppliers" everywhere ?

There was a stubby page titled "Ionic liquids" that I have redirected to this page. The previous content of that page is as follows:
 * Ionic Liquids are a class of ionic materials that are liquids at temperatures below 100°C. These ionic liquids can be made from uncountable combinations of organic and non-organic cations and anions. These ionic liquids are conductive and some can have some solubility for solid compounds that are solid due to hydrogen bonding, such as cellulose. Cellulose can be solublized up to 20% in the ideal ionic liquid. Any water present in cellulose and ionic liqid must be eliminated for there to be solubility.

If anyone can incorporate any of this information into "Ionic liquid," please do so. Tomgally 07:33, 11 Jun 2005 (UTC)

VOC
What's "VOC"? 212.201.44.249 12:23, 24 August 2005 (UTC)
 * VOC stands for Volatile Organic Compounds V8rik 14:28, 24 August 2005 (UTC)

toxic
I added the bit about aquatic toxicity, my research group currently is testing them, if I can I'll put up some of our relevant citations Helluo 05:13, 27 November 2005 (UTC).

historical context
Shouldn't the article have something about the history of these materials; who discovered them, and how? -- Cimon avaro; on a pogostick. 16:29, 5 March 2006 (UTC)

I've added a wee bit on the background. However, one should probably add better references on the origin and applications of haloaluminate ionic liquids. Or I'll do it when I can find more time. --Caohlin 15:18, 6 March 2006 (UTC)

The reference shown here for the first IL is wrong. The first article that contains an IL is found here: https://onlinelibrary.wiley.com/doi/full/10.1002/cber.18880210287 It is actually the article directly before the article of Gabriel and Weiner published in the same journal. — Preceding unsigned comment added by 141.14.233.246 (talk) 13:31, 17 April 2018 (UTC)

The relevant passage is this (german) "Beim Eindampfen einer mit Salpetersaure ubersattigten Vinyl-aminlösung verbleibt ein farbloser  Syrup, welcher beim Verweilen irn Exsiccator allmahlich zu einer  faserigen Krystallmasse erstarrt.   Diese wird mit wenig Alkohol verrührt, abgesogen, mit etwas Alkohol ausgewaschen und uber Schwefelsaure getrocknet. Die derartig erhaltenen, farblosen,  flachen Krystalle sind  hygroskopisch,  schmelzen bei 52-53' und  bestehen aus P-Oxathylaminnitrat, OH. CH2. CH2. NH2, HNO3" Basically: Concentration of a solution of vinylamine oversaturated with nitric acid yields a colorless viscous liquid. Drying in an exsiccator yields a solid. Washing with ethanol and drying over sulfuric acid yields flat, hygroscopic crystals with a melting point of 52 to 53°C. OH-CH2-CH2-NH2;HNO3

Unit conventions
People have added a space between the degree symbol and the temperature at least twice now. The convention, at least when submitting scientific articles, is that there is no space before nor after i.e. "34°C" is correct, whereas "34 °C" is 'incorrect'. --Caohlin 08:28, 17 May 2006 (UTC)

Ambiguity
"The influence of the group of Kenneth Seddon at Queen's university, Belfast, which has now turned into the first research centre dedicated to ionic liquids, QUILL, should also not be underestimated."

Does that mean anything? I'm not sure why this was added, if it has value because of the direction that this specific group is taking research in the field, perhaps that direction should be noted.

AndoSEKleton 16:27, 17 May 2006 (UTC)

The intention was to underline the importance of Seddon in a historical sense - it's my understanding that he spent a lot of time in the mid-late 90's attending conferences talking about ionic liquids. Also, a number of researchers active in the field have at one point been associated with his group or attribute the origin of their interest in ionic liquids to discussions with him such as Tom Welton (and via him, Paul J Dyson), Robin D. Rogers and John D. Holbrey. --Caohlin

I absolutely agree that this is worth noting in the article, I just think that a fuller explanation (such as the above) is more useful to and tonally consistent with the rest of the article. AndoSEKleton 18:34, 22 May 2006 (UTC)

Ken Seddon has not been the only proponent of low temperature molten salts and whilst his contributions to the field are significant, there has been some inconsistency if you read between the lines and follow the spin. I would also not call the achievements of QUILL pure academic research. I would recommend not to include Ken Seddon in the introduction of the article but rather have a separate section detailing the history of ionic liquids where Ken Seddon and others can be elaborated on. Hammertime909 (talk) 05:44, 6 October 2010 (UTC)

imidazolium ionic liquid
During some lab work I've achieved some confusing results. For instance when diethyl acetilenedicarboxylate and [1-hexyl-3-methylimidazolium][BF4] are mixed together, the solution colour changes from orange to dark red. Is this to be expected? Does it have anything to do with conjugation enhancement? or something just went wrong?


 * Imidazolium salts are colourless when pure. I suspect the intial colour was due to an impurity, and this impurity reacted with the alkyne to give you the red colour.

Hydronium bisulfate?
Surely equimolar solutions of water and sulfuric acid or nitric acid were known long before the compounds discussed in this article? Why are they not considered ionic liquids? --Atemperman (talk) 19:11, 7 April 2008 (UTC)

They are not pointed out as ionic liquids because they do not fit in with the gospel of QUILL as being something new and different. It's politics and marketing, full stop. 35 M aqueous KCl is also an ionic liquid, and a good electrolyte, as is sea water. According to QUILL, some salts ARE ionic liquids because they fit in with the gospel that salts forming stable liquids only do so at T < 100C (arbitrary, completely), while other combinations do not. This is complete rubbish, temperature discrimination has absolutely no place in the definition. If the material is composed predominantly of ions, it is an "ionic liquid" or liquid electrolyte etc. Same common sense idea is already employed for molecular liquids. Imagine that we would say water is a molecular liquid, but acetone is not, based on some arbitrary temperature. —Preceding unsigned comment added by Kenisadick (talk • contribs) 17:12, 7 July 2009 (UTC)

Soaps
How come liquid soaps aren't mentioned anywhere on here? They're essentially salts of potassium cations and long-chain carboxylate anions, aren't they? Most commercial soaps aren't pure compounds, that's true, but couldn't you isolate one that was (e. g. potassium dodecanoate?) Also, they've been known for a far longer time than ethylammonium nitrate!

Stonemason89 (talk) 17:38, 16 August 2008 (UTC)


 * Sodium laurate (can't find potassium salt) is a solid. So, that won't be a RTIL. --Rifleman 82 (talk) 18:33, 16 August 2008 (UTC)


 * The article on soap says that sodium soaps are generally solid, while potassium soaps are generally viscous liquids (it doesn't mention why, though). Following the trend, rubidium and cesium soaps would be expected to be runnier liquids at RT. Whether this is actually true or not is an open question; I don't know of anyone actually washing their hands with Rb or Cs-based soaps. Stonemason89 (talk) 22:01, 16 August 2008 (UTC)

Aliphatic compounds
Isn't an olefin a type of aliphatic compound? If so how can they show different solubilities? 81.223.140.162 (talk) 11:33, 24 October 2008 (UTC)

Copy-edits
Enjoy and comments appreciated. Lfstevens (talk) 15:28, 15 June 2010 (UTC)

Cellulose Processing
I believe this section has been changed a few times in the past but somehow still retains erroneous statements like this:

'A more intensive exploitation of cellulose as a renewable feedstock has to date been prevented by the lack of a suitable solvent.' as of Wed August 25th 2010.

Cellulose IS intensively exploited without the use of ILs...granted a wider range of solvents and understanding of cellulose processing is now more accessable with ILs but solvents and the technology are certainly not lacking.

'IL now allows real cellulose solutions at technically useful concentrations.[25]' as of Wed August 25th 2010.

There are many solvent systems already known to 'dissolve' cellulose to technically useful concentrations....please refer to seminal texts, such as 'Comprehensive Cellulose Chemistry' by Klemm, Philipp, Heinze, Heinze & Wagenknecht. There has been several hundred years of cellulose chemistry before the field of ionic liquids started...or molten salts for that matter. Proper definition of 'solution' in these cases should also be adhered to.

Im not pointing any fingers but it seems that some people are using this page as a blatant advertisment for themselves. I would not be against this as there are publications of some quality cited but this should be done responsibly avoiding misinformation.

Hammertime909 (talk)

Commutator
These liquids can be used instead of mercury in commutators of electric motors.--84.232.141.36 (talk) 17:34, 7 April 2011 (UTC)

Big edit
I removed a lot of wording from the article today, in the process of separating real applications from potential applications. The sections on processing of cellulose, algal biomass, pulp etc was filled with short well-intentioned essays about why these developments would be good. Similar discussions were compressed. I will soon go back and re-examine the section on nuclear processing which looked to be the subject of some citation spamming. I have nothing against the area but I figured that readers deserve to see a difference between real applications and potential ones and, further, readers done need what appeared to be moralizing about why clean and green is good. If other readers feel concerned about my edits, please leave a note or if you are very concerned, revert what I did or am about to do. --Smokefoot (talk) 00:16, 8 May 2015 (UTC)

External links modified
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 * Added archive https://web.archive.org/20090312011018/http://www.bioniqs.com:80/applications_plastics.php to http://www.bioniqs.com/applications_plastics.php

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External links modified
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I have just added archive links to 1 one external link on Ionic liquid. Please take a moment to review my edit. If necessary, add after the link to keep me from modifying it. Alternatively, you can add to keep me off the page altogether. I made the following changes:
 * Added archive http://web.archive.org/web/20090718210309/http://www.sigmaaldrich.com/etc/medialib/docs/Aldrich/Brochure/al_material_matters_v2n2.pdf to http://www.sigmaaldrich.com/etc/medialib/docs/Aldrich/Brochure/al_material_matters_v2n2.pdf

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Its a big area: report from Chemical Abstracts
Here are some data from Chemical Abstracts Service, as of March, 2017: --Smokefoot (talk) 20:45, 7 March 2017 (UTC)
 * almost 33,000 reports have appears on "ionic liquids"
 * 3245 appeared in 2016 alone.
 * more than 700 reviews have appeared.

Smokefoot_Censorship_Thought_Police
After adding a very brief comment to the "characteristics" section, that indicates ILs hydrolyse in water, and included the reference to Gordon Driver, Smokefoot, Thought Police Extraordinaire, has twice removed this. And I have twice undone that, and will continue to do so.

Smokefoot takes this action under the exaggerated premise that it is somehow "inappropriate" for anyone to cite primary journal sources, when many of the existing entries in the bibliography, are from "primary journal sources".

I then received a "warning" from Smokefoot to "be careful". Thanks Smokefoot, for your concern for my safety, but if there is a wiki page on ILs at all, it should at least try to keep up with the accuracy of the established scientific record, and continuous removal of such important knowledge and information from the ILs "characteristics" section, only indicates you are acting in your own vested interests and not on behalf of practitioners.

As far as I understand it, this is "wiki"pedia, not "smokefoot"pedia. Perhaps you are more tuned to starting your own blog, where you can faithfully portray whatever narrative you wish.

Stop interfering with the information flow. Reading64
 * Thanks for the note.  There is no intrinsic interest on my behalf in suppressing information flow, of course.  There is however authentic interest - indeed a commitment - of the Wikipedia community to facilitate readability of articles.  We obviously could cite the other 3000+ references from the year your paper appeared.  Doing so however would wreck that article. So encouraging such behavior is counterproductive. This "reference bloat" is the reason for many guidelines, such as WP:SECONDARY, WP:NOTJOURNAL, WP:RECENTISM, etc.  A lot of new editors dont like these guidelines, initially because they don't appreciate the nature of the problem. --Smokefoot (talk) 16:05, 8 March 2017 (UTC)

35,463 References to IL's and counting
As of today, 35,463 reports, patents, papers have appeared on "ionic liquids". Of these, 791 are classified by SciFinder as "Reviews". Of those reviews, 372 have appeared since 2012. Given the abundance of reviews, it should be easy for anyone interested in helping readers, to build their content around them, vs inserting primary references.--Smokefoot (talk) 15:39, 7 November 2017 (UTC)

poly(ionic liquid)s
Not only the section poly(ionic liquid)s should be expanded but also a wikipedia page should be created because poly(ionic liquid)s become more popular than ionic liquids. poly(ionic liquid)s have the ionic properties of ionic liquids. Many of the works on ionc liquids including those cited and discussed in this wikipedia page are actually about poly(ionic liquids). — Preceding unsigned comment added by 2A00:23C4:1A02:9300:D06:DED1:4A12:3086 (talk) 17:39, 16 November 2017 (UTC)
 * Thank you for your comments and advice. Please help find some WP:SECONDARY sources (reviews) focused on poly(ionic liquid)s. Also please help to define the polyionic liquids. As I mentioned above >370 reviews have appeared on IL's recently.  So there must be some good citations that we are missing.--Smokefoot (talk) 19:02, 16 November 2017 (UTC)