Talk:Acetone

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[edit] Discoverer

--209.23.238.183 10:57, 12 Sep 2004 (UTC)I need to know who discovered acetone. I need this for a report and have not been able to find it. Does anyone know?

I suspect the answer which you're seeking is Chaim Weizmann, who didn't actually discover it, but did discover a cheap method of making it for the British in WWI. Weizmann is also famous for being the first president of Israel. -- DrBob

[edit] Cleaning

Acetone seems to be good for cleaning glass and removing sticky adhesives from same. I wonder how good it is for thinning a touch up primer that is now too thick.. I do not know if acetone was originally an ingredient.

Acetone is a solvent with a high vapour pressure and low boiling point. If you add it to your primer, it will definately make it thinner and will likely disperse evenly, as it is miscible with every other common solvent. However you may get streaking when you try to apply your paint, as you might get a chromatographic effect when you apply it to paper -- it will take some of the ingredients which dissolve well in acetone but do not adsorb well to your surface and carry them farther than components of your primer which either adsorb well to the surface or are not very soluble themselves in acetone. Try a small amount first, then try a small patch, to see if you get the ratio right and if it affects performance. Sewercockroach 22:03, 12 July 2007 (UTC)

[edit] Structure

It appears that the picture of the chemical formula is broken, since it only shows 3 bonds and one Oxygen atom for me, and the chemical formula is much more complex.

This is a standard abbreviated diagram, commonly used in organic chemistry to avoid writing CH/CH2/CH3 over and over. To interpet such diagrams, everywhere there's an unlabelled vertex put a carbon atom, and any unused carbon valences get a hydrogen atom. Securiger 13:52, 14 Feb 2005 (UTC)
Well, to those people who have a basic knowledge of chemistry but aren't familiar with the conventions of organic chemistry it appears broken. This needs a link to a page telling people about this convention (is there such a page?)
~ender 2005-02-24 22:58:MST

The image that is displayed is the skeletal formula. It only shows the bonds between Carbon atoms, as well as other atoms or functional groups, with the exception of hydrogen. It is to show the basic shape of the molecule. Wherever there is a vertex without a label, it is a carbon atom.

DrBob, I'm interested in the cheap method of manufacture, where did you get the information on Weizmann?

-- ~ender, 2005-02-12 12:03:MST

[edit] From Talk:Propanone

I will be moving this page back soon to its original location as acetone. Wikipedia policy states that "use the style of the International Union of Pure and Applied Chemistry (IUPAC) for chemical names wherever possible, except in article titles, where the common name should be used if different, followed by mention of the IUPAC name." Acetone is such a common chemical and it is nearly always referred to by that name, even in chemical catalogues. IUPAC recognises this, and allows use of acetone as a name].

A Google search for acetone generates 1,100,000 hits. Propanone generates 41,000.

I will move the page back tomorrow once people have had a chance to comment. Walkerma 20:26, 12 May 2005 (UTC)

Most of the history for this page is to be found under the acetone page. No evidence was presented before the edit-move to support the claim that "Acetone is no longer the officially recognised name of propanone." Walkerma 04:49, 14 May 2005 (UTC)

I agree, acetone is the correct title. Just one comment, this appears to have been a cut-and-paste move with subsequent edits at this name, so whatever you do you will lose some page history. -- Securiger 13:49, 15 May 2005 (UTC)

[edit] Fuel additive

(* warning the following section is hearsay *)

In the last few months, there has been some discussion of acetone as an additive in gasoline and diesel to improve performance of those fuels [1]. However, there doesn't appear to be very much scientifically-gathered data out there to support this idea as of yet. In the past, acetone has been a well-known addition to racing fuel, though the recent discussions talk about using it in much lower quantities—fractions of one percent rather than, say, 20% or higher mixes. It's not really clear how the mixing of fuel to have 0.15% or 0.25% acetone can change much, other than primarily cleaning built-up residues out of an engine, unless it acts as a catalyst or something. (Note: evidence suggests the acetone acts as a mechanism to reduce surface tension of fuels. The result is a cleaner, more efficient burn [User:JKS]) Anyway, it's interesting, and I considered adding some notes to this article, but I decided against it for now since the current evidence is so limited. —Mulad (talk) June 29, 2005 00:26 (UTC)

Mulad- I'm not a fuel scientist though I am an organic chemist, so I have acetone instead of blood running through my veins! The science on the website you cite seems suspect to me- if you could change vapour pressure like that you could lower the boiling point of water in a similar way, and I don't think you can. I'd guess that acetone helps dissolve traces of water that might otherwise cause the engine to run less well. Pure gasoline or diesel can only dissolve a tiny amount of water, but rather more if acetone is added- there are commercial additives for gasoline that work the same way. That's my guess. Please let us know if some scientific studies are done on this. Walkerma 29 June 2005 05:12 (UTC)

Walkerma- if you can lower the surface tension of a liquid, it will vaporize more readily. And one way to reduce the molecular cohesion of a substance is to introduce a surfricant. So, the question is, is acetone really a sufricant? Brontus

From what I'm gathering, the common recommendation is about 3-5 oz per 10 Gallons of fuel. Found this on Fark, but I'm not trusting it enough to put my life to it: http://peswiki.com/index.php/Directory:Acetone_as_a_Fuel_Additive -- also, some of the links they're showing are dead and forward to unnecessary sites.. so don't bother with those. I did find that in general an interesting, if not accurate read on the subject of using acetone for fuel additives, however. Rickz0rz September 7, 2005 06:17 (UTC)

GS- I've run experiments in my Ford Expedition. I went from 12-12.5 MPG to 15.25MPG. The primary reason for individuals NOT finding success with Acetone in fuel has been the overuse of it. the above recommendation of 3-5 oz per 10 gallons likely would cause a decrease in fuel economy for many vehicles. If you're interested in trying this, start at 1oz and work your way up slowly. Also, be sure to use 100% acetone. My vehicle received the 18%+ efficiency gain with only 1.25 oz per 10 gallons.


A CLOSER LOOK:

In a popular article quoted above, Mr. Louis Lapointe states that greater combustion efficiency is achieved through the lowering of surface tension of the fuel by the addition of acetone (a ketone) or methyl ethyl ketone resulting in a significant increase in fuel economy and lower exhaust emissions. Many aftermarket fuel additive companies have claimed significant mileage increases through better combustion as well. Both gasoline and diesel, comprised of non-polar hydrocarbons, already exhibit very low surface tension. C8, for example has a surface tension of 21.80 dyne-cm compared to water at 72 dyne-cm at 25 degrees centigrade. As a liquid is heated there is a corresponding decrease in surface tension up to the point at which the liquid vaporizes. In a warm, well running engine, the fuel is in vapor phase during the combustion cycle leaving surface tension no part to play as surface tension pertains to liquids, not gasses. During the compression stroke of a direct injection diesel engine, the temperature of the intake air is typically in excess of 1000°F (from compression) before the fuel is injected at more than 20,000 psi while, in gasoline engines, the fuel is vaporized in the ports before entering the cylinders. Needless to say, during the ignition process, the greatly increasing temperatures and resulting turbulence vaporize any fuel that may still be in atomized form. The bulk of the vaporized hydrocarbons that do not oxidize are generally in regions of the cylinder which tend to remain at temperatures too low to support combustion and in areas where the mixture is too lean for the vapor to ignite; an example would be the space between the piston and cylinder wall just above the top compression ring. This amount of unburned fuel, though, is quite small, ranging from 1% to 2% in modern gas and diesel engines. Those that would say that fuel is still burning after leaving the cylinder need to remember that exhaust temperatures measured in the exhaust manifold run between 1000F to 1400F while running at full power when the exhaust is at it’s hottest. These temperatures are far below a gasoline or diesel flame (>3500). Combustion efficiency is affected to a far greater extent by the physics inherent in engine design than by chemistry.

Quoting Chevron Oil: “Combustion catalysts may be the most vigorously promoted diesel fuel aftermarket additive. However, the Southwest Research Institute, under the auspices of the U.S. Transportation Research Board, ran back-to-back tests of fuels with and without a variety of combustion catalysts. These tests showed that a catalyst usually made "almost no change in either fuel economy or exhaust soot levels." While some combustion catalysts can reduce emissions, it is not surprising that they don't have a measurable impact on fuel economy. To be effective in improving fuel economy, a catalyst must cause the engine to burn fuel more completely. But there is not much room for improvement. With unadditized fuel, diesel engine combustion efficiency is typically greater than 98%. Ongoing design improvements to reduce emissions are likely to make diesel engines even more efficient.” http://www.chevron.com/products/prodserv/fuels/bulletin/diesel/L1_toc_rf.htm]

“Incomplete burning of fuel is insignificant in modern cars. Fuel combustion today typically exceeds 98 percent.” John Heywood, professor of mechanical engineering at MIT and an authority on internal-combustion engines.

Using the above figures, if the addition of acetone / methyl ethyl ketone (or any other additive) to the fuel was to produce even 100% combustion, with zero unburned hydrocarbon emissions (which it will not), we would only realize an additional 1% - 2% increase in thermal energy. The diesel engine is about 50% thermally efficient, (gasoline 30%) with 50% of the energy of the fuel available to turn the engine while the other 50% is being shed primarily as heat from the radiator and exhaust. This would leave an increase of .5% to 1% of usable energy that could be applied to overcoming friction in transmission, wheels, radiator fan, etc. and increasing mileage. Assuming our mileage averaged 18mpg, we would realize 18mpg + .5% to 1% = 18.09mpg – 18.18mpg in theory with the practical amount a fraction of that. Assuming acetone addition would provide 100% combustion efficiency, (and there is no scientific evidence to support the assumption that it increases efficiency at all), and not factoring in loss to friction in drive train, etc., the resultant theoretical increase of far less than 0.1mpg would be so negligible so as not to be measurable. Statements such as “Most fuel molecules are sluggish with respect to their natural frequency. Acetone and/or methyl ethyl ketone has an inherent molecular vibration that "stirs up" the fuel molecules, to break the surface tension” are pure pseudoscience and are not found in the nomenclature of chemistry. As a recent study by Cummins Diesel demonstrates, fuel mileage can be affected up to 30% by driving habits alone. How many are expecting to see an increase in mileage after the addition of acetone or methyl ethyl ketone? How much is this expectation affecting driving habits? And how many people are going to report it if they saw no increase and how many will become discouraged and just "forget the whole thing"? How do we account for the people that report a decrease?

[edit] Context?

"Acetone is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances."

Anyone have information on the specific reason it is listed as a precursor? Are there any particular drugs that people use acetone in making? --Head of the Caligula Appreciation Society 09:36, July 19, 2005 (UTC)

This statement is near the end of the beginning introduction:

Acetone is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[1]

It would be useful not to have this just be dropped in there without explanation and context. Why is it a narcotic / psychotropic substance, who are the people that abuse it, what are its effect on humans, how does this (solvant abuse?) affect the nervous system to produce the 'high'? If it is just solvant abuse then a link there would be good but I am not sure in what context this chemical is 'illicit' but that is my guess.--ShaunMacPherson 12:59, 12 August 2005 (UTC)

I think the key word here is precursor. It isn't a "drug" in itself, it is simply used to make drugs. Of course most things can! You can still buy acetone at many hardware stores in the US (I think!), so I don't think it's considered a serious problem. I tried following the links, and although I found what the convention is, I found no link that tells me the meaning of the phrase "Table II precursor." I can only guess that if you are a Bolivian farmer who has 10 tonnes of acetone in the barn you can now get arrested for it.
Personally I hate having this awkward phrase in the opening section of the article (and several other articles), but I left it in because I assumed it was of great topical interest. I had also noticed the slant of interest in Wikipedia- many psychedelic substances have had full-length articles for a long time, while major commodity chemicals like sodium sulfate had nothing at all! However in light of the fact that
  • It spoils the flow of the article, and
  • If one clicks on the given links to find out what the phrase means, you come to a dead link. (Since it is an incomprehensible phrase by itself, it probably shouldn't be there at all.)
Therefore I'm moving this phrase down to "Uses" (it is NOT a fundamental property or use of acetone), and linking to a definition of precursor. If you have any other suggestions, please give them here. Walkerma 15:10, 12 August 2005 (UTC)
Update – I removed the confusing phrase from the article altogether. Reasons are twofold:
  • The definition of what "Table II Precursor" means is unclear. I requested a definition here, but after several months there has been no response.
  • Until the first point is clarified I can't be sure, but as I understand it acetone is NOT an illicit drug like heroin (it's available in most hardware stores in the US over the counter), merely that it can be used (probably as a solvent) for making a major drug. That is probably true of most major organic solvents, and it is not an unusual feature of acetone. Until some explanation is provided of how acetone in particular needs this information, I think it is merely confusing, alarmist and unnecessary. Walkerma 16:58, 1 November 2005 (UTC)
    • Indeed, acetone is listed in table II of the said Convention, as a "chemical frequently used in the illicit manufacture of narcotic drugs" and not as a precursor per se. This may lead to regulatory restictions on the sale of large quantities of acetone in various jurisdictions, but for the time being I know of none in the jurisdiction in which I am resident (France, which controls the supply of various table I substances including, for example, acetic anhydride). I support the removal of the information from the article until such time as we can provide a balanced overview of the regulations concerning the supply of chemicals in the major English-speaking countries. Physchim62 (talk·RfA) 18:39, 1 November 2005 (UTC)

[edit] Uses in drugs production

Acetone and other solvents are uses in purification of hundred of compounds, because diferent solvents are diferent partition coeficient for each substance. One simplest example: a solution of iodine and water can be almost completely separed adding toluene and mixing. Toluene dissolves most iodine and much less remain in water, and toluene is separed as a other layer. Most alkaloids (cocaine, cafeine, heroin, etc) are extrated from plants with solvent and purified with sequential solvent extrations of remaining solutions.

[edit] A Properties Database

Thanks for these data. I will try to put any new ones on the Acetone_(data_page) when I get a chance. Walkerma 18:14, 21 February 2006 (UTC)

Freezing Point: -94.7C Flash Point: -18C Flash Point Method: CC Autoignition Temp: 465C Explosive Limits:

  Lower: 2.2 % 
  Upper: 13 %

Refractive Index: 1.355 Density: 0.784 g/cm3

  Density Temp:  25C

Vapor Density: 2 Vapor Pressure: 30.8 kPa

  Vapor Press. Temp:  25C

Constants of Antoine Equation P = 0.13332210 exp[A - (B/(C+T))], where P is Vapor Press.(kPa) and T is Temp. (C):

  A:  7.02447 
  B:  1161 
  C:  224

Viscosity: 0.3029 cP Surface Tension: 22.68 mN/m Acid Dissociation Constant, pKa: 24.2 Donor Number, DN: 17 kcal/mol Cubic Expansion Coefficient: 12.5 Polarity Parameter, ET(30): 42.2 kcal/mol Acceptor Number, AN: 14.8 10-4C-1 Specific Heat: 29.85 cal/mol K Thermal Conductivity: 0.000428 cal/s cm K Heat of Combustion: 30.82 MJ/kg Dielectric Constant: 20.56 Water Solubility: infinite Hildebrand Solubility Parameter: 10 cal1/2 cm-3/2 Hansen Solubility Parameter:

  dD:  15.5 
  dP:  10.4 
  dH:  7

Henry's Law Constant: 0.0000388 atm m3/mol Evaporation Rate Butyl Acetate=1: 6.6 UV Absorption Maxima: 270 nm (in MeOH)

Health & Safety Threshold Concentrations Threshold Limiting Value - 8h time-weighted average

  ACGIH: 750 ppm  NIOSH: 250 ppm  OSHA: 1000 ppm 
  ACGIH: 1780 mg/m3  NIOSH: 590 mg/m3  OSHA: 2400 mg/m3

Maximum Concentration for a Continuous Exposure of 15 min. STEL

  ACGIH: 1000 ppm     OSHA: 1000 ppm 
  ACGIH: 2380 mg/m3     OSHA: 2400 mg/m3

Maximum 30 min. Exposure Concentration

  NIOSH-IDLH: 2500 mg/m3  48,400 mg/m3

Odor Threshold: 13 ppm

Toxicity LD50

  Oral: 5800 mg/kg     Dermal: 20000 mg/kg

Route of Entry: Inhalation, Ingestion, Skin Contact Target Organs: Respiratory System, Skin, Liver, Kidney Carcinogenicity:

  IRAC: N  NTP: N  OSHA: N

Mutagenic Properties: N

Effect on Environment Biological Oxygen Demand, BOD:

  5-Day Test: 0.85 g/g

Chemical Oxygen Demand, COD: 1.92 g/g Theoretical Oxygen Demand, ThOD: 2.21 g/g Biodegradation Probability: days-weeks Bioconcentration Factor: -0.4 Soil Adsorption Constant: 1.26 Octanol/Water Partition Coefficient: -0.24 Hydroxyl Rate Constant: 2.26E-13 cm3/molec s Urban Ozone Formation: 0.01 Montreal Protocol: N

[edit] Section removed

I have removed the section "Use as a cleaning solvent" from the article because I think it has minimal significance, it is written in an unencyclopedic style, and it comes across more as instructions on how to clean lab glassware than as a description of acetone itself:

Due to the relatively polar properties of acetone and its high rate of vaporization, it has been used in many university labs as a cleanser for substances in test tubes after working with all manner of organic substances (e.g. cyclohexane, cyclohexene). Acetone is squirted directly from a bottle containing the substance onto the glassware and is (usually) drained into a specially marked organic waste bucket. Acetone is particularly useful because it is inexpensive, is moderately polar allowing it to dissolve a wide range of organic substances, and evaporates quickly. However, care should be used when cleaning test tubes with acetone as acetone is readily absorbed through vinyl or latex gloves and will come in contact with skin where it is absorbed into the skin. If an excessive amount of acetone is splashed onto gloves, remove gloves immediately and wash hands with water before donning a new pair of gloves. Due to its high volatility, acetone evaporates quickly. A quick way of drying wet glassware is to rinse the inside surfaces of the freshly washed item with acetone. Since acetone is miscible with water, any water present will be removed as the acetone is poured out. The remaining film of acetone (containing traces of water) will evaporate quickly on the bench or inside an oven. Also, if you want to speed up the evaporation of the acetone, you can blow the glassware with compressed air underneath a fume hood.

In my opinion, the article could use some expansion in terms of the use of acetone as a solvent and cleaner, and perhaps portions of this section can be used for that purpose. --Ed (Edgar181) 12:47, 6 February 2007 (UTC)

The exceedingly common use fo acetone as a cleaning agent in laboratories should definitely be mentioned. Sewercockroach 22:03, 12 July 2007 (UTC)

[edit] Azeoptropic Information

Azeotropic data should be either mentioned on the Acetone main page or the data page. Acetone doesn't form azeotropes with dichloromethane or water, but it does with hexane(s) according to http://www.solvent--recycling.com/azeotrope_1.html. Sewercockroach 22:03, 12 July 2007 (UTC)

[edit] Change redirect from Nail polish remover

I believe a distinct article should be created for nail polish remover, as not all nail polish remover is a solution of acetone. In fact, many manufacturers avoid acetone nowadays, and some use nitroethane I've heard.

68.19.26.57

[edit] "Safety" section is useless.

What are "incompatibilies," chemically speaking? This section needs expansion/explanation. —The preceding unsigned comment was added by 71.100.182.201 (talk) 11:02, August 22, 2007 (UTC)

Might also be a good idea to reiterate its flammability here 161.115.50.8 01:41, 2 November 2007 (UTC)

User 71.100.182.201: Regarding "incompatibilities". Acetone is a relatively inert chemical and an excellent organic solvent; for this reason, it is used to clean organic laboratory equipment. However, one should avoid using acetone if said glassware is contaminated with bromine, as the resulting reaction will yield bromoacetone gas, a lachrymatory substance. (References: Wikipedia; Macroscale and Microscale Organic Experiments ). Murphy2010 (talk) 05:49, 10 February 2008 (UTC)

If you're working with bromine in the first place, you better be able to handle ordinary chemicals safely. --Rifleman 82 (talk) 08:05, 10 February 2008 (UTC)

[edit] Toxicology sections makes bold statements with zero citations.

I added "citation needed" links but according to:

http://www.des.state.nh.us/factsheets/ehp/ard-ehp-7.htm

at least some of the statements therein are inaccurate. —Preceding unsigned comment added by 67.170.12.20 (talk) 19:35, 11 May 2008 (UTC)