Talk:Trinitrotoluene

Instruction manual

Should this article really include instructions on how to make TNT? User:Ajayfahlman User:Tannin: Do you know that "adsorb" is a word, what it means, and that it's not the right word meant here? It's not a common word, certainly, so I'm thinking you might not have realized it could be right. It refers to accumulating liquid or gas on the surface, which is an important thing where explosives are involved. -- John Owens 10:27 Mar 31, 2003 (UTC)

I'm no chemist, John, so you may well be right. Change it back if you think it best. Tannin

68.231.184.131 (talk) 23:24, 5 November 2008 (UTC)Maybe. But, TNT is difficult, requires many steps. Any home bomber already knows of much easier substances that can be home made, anyway.68.231.184.131 (talk) 23:24, 5 November 2008 (UTC)

As the guy above me said, TNT is a hard compound to make. With the current "Instructions" given, it still takes about 2-3 hours of hard calculations, and a good deal of experimenting, to get it right. Unless one is a good chemist, there is a pretty good chance one would mess up alot,, and do bodily harm to themselves in the process. Wertyu739 (talk) 13:50, 5 September 2011 (UTC)

Combustion energy compared to fat/sugar

The combustion energy comparaison to fat and sugar per unit of mass is dubious at best as it doesn't count the mass of oxygen needed to extract energy from sugar and fat... JidGom 14:21 2 Jun 2003 (UTC)

I'm not actually going to do the stoichiometry right now (bother me later if you really want to know), but I'm pretty sure that sugar and fat are still more efficient if you count in the sugar. -Smack 06:36 7 Jun 2003 (UTC)

Thanks to Google I found hints about heating energy of TNT. I insert them again.

Pale yellow solid

Trinitrotoluene (TNT) is a pale yellow crystalline, aromatic hydrocarbon compound that melts at 81 °C (178 °F). It was consumed by the ancient Chinese with the belief that it would grant spiritual enlightenment. However, Chinese emperor Xang Tsui Chow forbade the pale yellow compound because he believed it was the reason for the yellow taint of his people's skin and hoped that outlawing it would make his people look more like the superior cultur residing in Europe. Today, Trinitrotoluene is known as an explosive chemical and is a part of many explosive mixtures, such as when mixed with ammonium nitrate to form amatol. It is prepared by the nitration of toluene (C6H5CH3), it has a chemical formula of C6H2(NO2)3CH3. In its refined form, Trinitrotoluene is fairly stable, and unlike nitroglycerine, it is relatively insensitive to friction, blows or jarring, and, therefore, makes it an ideal part of ones daily consumption plan. It does not react with metals or absorb water, and so is very stable for storage over long periods of time. It is often stored as fat after human consumption and later may act to supply a surprising and explosive amount of energy. Modern physicians recommend that people consume at least 6 to 8 cups of refined Trinitrotoluene per week in order to maintain a sufficient energy level.

The specific combustion energy of TNT is 4.6 MJ/kg, hence 1 kt TNT = 4.6 TJ (terajoule), 1 Mt TNT = 4.6 PJ (petajoule).

Non-nuclear explosives release less energy per kilogram than everyday products like coal (30 MJ/kg), wood (10 MJ/kg), fat (38 MJ/kg) or sugar (17 MJ/kg); they do, however, release their combustion energy much more rapidly.

Keep the vandalism its slightly amusing Rjstott 10:41, 6 Apr 2004 (UTC)

68.231.184.131 (talk)TNT is made with Toluene, not benzine.68.231.184.131 (talk) 23:17, 5 November 2008 (UTC)

Lead section revision?

The third paragraph of the lead section (begins with "Amounts of TNT are used as energy...") doesn't seem to me to be appropriate for a lead-in. While it's useful information it doesn't lead in to anything. Also, since it's not a very long article the lead-in should be less than 3 paragraphs anyway, perhaps this paragraph can be moved to its own section further down the page? 192.76.80.75 07:11, 11 Dec 2004 (UTC)

SMILES?

What is the SMILES depiction for TNT?

SMILES depiction is simply an image, molecule formula. The SMILES code for TNT is Cc1c(N(=O)=O)cc(N(=O)=O)cc1N(=O)=O

Isomers

This article doesn't really talk about the isomers, but Collier's New Encyclopedia (1921) had this to say:

"There are three compounds of this name, all having the same chemical constitution, but differing in the arrangement of the nitro groups in the molecule. These three are known respectively as A, B, and Γ trinitrotoluene. The most important of the three is A or symmetrical trinitrotoluene, which forms the constituent of the explosive well known as TNT. B and Γ trinitrotoluene, when fused with sodium sulphide and sulphur, yield dyes which give a deep khaki-brown shade. Most of the TNT used for explosive purposes contains small amounts of the B and Γ isomers, but for some purposes a very pure TNT is required..."

—Mike 09:23, Jan 9, 2005 (UTC)

I suspect that those alpha, beta, and gamma designations have since been replaced by the numbers appearing in this article, identifying the one under discussion as 2,4,6-trinitrotoluene. Here's a source which also lists 2,4,5-trinitrotoluene as well as 3,4,5- and 2,3,4- and 2,3,6- varieties. [1]

Gene Nygaard 10:12, 9 Jan 2005 (UTC)

Thus with the mass–energy equivalence at 90 PJ/kg, 1 Mt TNT corresponds to 47 grams?

What is a nuclear physics concept such as mass-energy equivalence doing in an entry about the combustion energy of TNT? This is highly confusing. Someone asks: 'A million tonnes is equal to 47 grams? What?!'

Osgoodelawyer 16:25, 15 August 2005 (UTC)

Detonating TNT

Can someone elaborate on what is meant exactly by "dificult to detonate"? There is this amusing story on the net: Finally, there is the case of explosives scientist who fabricated an ash tray from cast TNT and kept it on his office desk for the use of visitors, only revealing its nature after they had extinguished a cigarette in it with no untoward results.

Commking November 2, 2005 "

Also, I don't think the page clearly outlines what is needed to actually cause TNT detonation, which would probably be normally found on such a page, no? 71.59.91.78 (talk) 03:57, 27 December 2007 (UTC)

You can detonate TNT easily, using any fire.Agre22 (talk) 02:42, 18 August 2008 (UTC)agre22

68.231.184.131 (talk) 23:19, 5 November 2008 (UTC)No you cannot. It takes a large #8 miltary blasting cap or a primer to insure TNT's conplete detonation.68.231.184.131 (talk) 23:19, 5 November 2008 (UTC)

Chemical infobox

Chemical infobox? Important subject. --Member 03:28, 4 December 2005 (UTC)

User:Guest 15 December 2005

One problem with TNT is that it's a Carbon rich explosive. Thus, the detonation of pure TNT tends to release the excess Carbon as a sooty (black) smoke. Addition of Ammonium Nitrate (thus producing Amatol) provides the extra Oxygen needed to push the stoichometry closer to the ideal value, thus releasing less soot. This can be important in battlefield applications since the sooty smoke from pure TNT may obscure potential targets.

Conflict

Seems as though there's a conflict with the IUPAC names in the sidebar and the main article. Are there two accepted IUPAC names or is this a mistake? Either way, it should be cleared up, and I don't know the right way to do so. Blutpanzer 03:45, 1 March 2006 (UTC)

Recipe for TNT

This section should be removed. See WP:NOT. Isopropyl 21:52, 11 April 2006 (UTC)

The synthesis is done in a stepwise procedure. First toluene is nitrated with a mixture of sulfuric and nitric acid. Even lower-concentrated acid mixtures are capable of doing the first and second introduction of a nitrogroup. The nitrogroups decrease the reactivity of the toluene drastically, because they are electron-withdrawing groups. After separation the mono- and dinitrotoluene is fully nitrated with a mixture of nitric acid and oleum (sulfuric acid with up to 60% dissolved SO₃), this mixture is far more reactive and is capable of introducing the last nitrogroup. The waste acid from this process is used for the first step of the reaction in industrial synthesis.

This was the text befor the exact manual and it was good to understand but not to redo it, and you are right!--Stone 12:29, 12 April 2006 (UTC)

i think its a mixture of carbon, nitric acid, and sulfer
the nitric acid can be made with the following formulas
NH3(g) + O2(g) → NO(g) + H2O(g)
NO(g) + O2 <=> NO2(g) delta H > 0 (means jou must put energie in it to go this way
NO2(g) + H2O(l) → HNO3(aq) + NO(g)

Done Dan100 (Talk) 21:17, 26 June 2006 (UTC)

German translating

I'm translating the German version because someone liked the diagrams... Bob

Okay...I'm stuck...I got down to the end of the history section (decided the English history was better) and got stumped in the present production section.

Anyone wanna take over? Bob 14:25, 12 June 2006 (UTC)

IUPAC name

The IUPAC name has been 'corrected' by 72.37.183.24, however it can be further improved by decreasing the numerals! The correct numerals for trinitrotoluene are 2,4,6- (as the toluene methyl is numbered 1), BUT when using benzene as the base molecule this no longer applies. In the case the nitro- groups should be numbered 1,3,5-, and as the previous editor points out, there is no ambiguity if the methyl- group is not numbered: giving methyl-1,3,5-trinitrobenzene (see also [2]). -- MightyWarrior 10:01, 21 June 2006 (UTC)

move specific combustion energy?

It would seem appropriate to add the value of the specific combustion energy (4.6 MJ/kg) to the "Characteristics" section of the text and to the "Characteristics" section of the table in the right-hand column. For an explosive, the specific combusion energy is arguably as important a characteristic as the density and the explosive velocity. Also, anyone with basic numeracy skills who wants to know the equivalent of a "megaton" or "kiloton" in CGS units is then spared the task of having to scan all the way to the end of the article and click through on the "megaton" link. -- Piperh 14:44, 11 February 2007 (UTC)

combustion energy

I see some discussion here of combustion energy. I am curious about the number at the Megaton page. Does anyone understand the 651 cal/g number cited there? I asked the author of the reference for a citation and an explanation. He replied, but he provided neither. The following reference looks useful. It puts the TNT energy value (heating value) at 3575 cal/g, and the detonation energy at 1093 cal/g. The 651 cal/g certainly looks bogus. http://www.osti.gov/energycitations/servlets/purl/3648-Pc0V6C/native/3648.PDF In particular the above says "An explosion energy of 3575 Cal/g was measured by calorimetric methods-in agreement with thermodynamic equilibrium calculations of the “Heat of Combustion” for TNT (based on the CHEETAH code [55]). Thus, the explosion-induced mixing of the TNT products with oxygen deposited an additional 2482 Cal/g of exothermic energy as a consequence of the turbulent combustion process. In the popular literature, this is known as “after-burning” in TNT explosions (see Dewey [56])." Jqwilliams007 (talk) 00:25, 10 September 2008 (UTC)

This is also the reason that a shift was made from straight TNT to amatol mixtures. Norm Reitzel (talk) 02:10, 1 February 2009 (UTC)

Extremely Similar to NationMaster Encyclopedia

There are some extremely similar sections and word choices to the NationMaster Encyclopedia's page on Trinitrotoluene. I am not sure if that was copied from wikipedia or wikipedia from there or maybe a common source they both used. Somebody should look into it. The URL is http://www.nationmaster.com/encyclopedia/Trinitrotoluene thegreatco (talk) 23:07, 17 December 2008 (UTC)

Ought be featured

I think it's about time this becomes a featured article. Jourdy288 (talk) 19:55, 4 February 2009 (UTC)

Incorrect Diagram?

It appears that the structural diagram of TNT is missing a methyl group at the top, as pointed out MIT Professor of Solid-State Chemistry Donald Sadoway in a recent lecture (See 49:22) 18.238.6.107 (talk) 06:42, 26 November 2009 (UTC)

Seems fine to me. The hydrogen atoms on the terminal CH3 are not expanded. --Rifleman 82 (talk) 07:29, 26 November 2009 (UTC)

It's not missing - but the shorthand (any non-noted point or terminus is a carbon) as opposed to just omitting the hydrogens, is not the clearest way to diagram it. A lot of chemists don't like that shorthand in diagrams. It's accepted in carbon ring diagrams, on the ring, but elsewhere seems to be discouraged. A methyl group hung off the ring should probably be labeled as such.

More importantly, though it's technically correct (professor exaggerated for effect), it's obscure and harder for normal people to understand. "What's that line for?" and "there's no atom there" are obvious questions a non-expert would ask. If the diagram confuses non-experts it's a very poor choice for Wikipedia.

I put the image back to the PNG we had before, that has the explicit methyl group. Georgewilliamherbert (talk) 09:26, 26 November 2009 (UTC)

I'd say it's a matter of personal preference more than anything else, and to say that "a lot of chemists don't like [it]" is perhaps an exaggeration. I personally find terminal -CH3 or -Me untidy and distracting, especially when you have a lot of them in a molecule. Especially so for t-butyl and isopropyl groups. Every field has its terminology and this is ours... so I really don't see a big deal.

I watched Sadoway clip, and for a third year chemistry student (guessing from the course code) not to understand this ... and for Sadoway to dismiss an *accepted* convention as incorrect is bewildering. --Rifleman 82 (talk) 17:41, 26 November 2009 (UTC)

Implied C in a skeletal formula is an IUPAC-blessed standard, not just a shorthand/jargon used by those in the field. When/whether to use it is a matter of preference and different fields may have different conventions, and it might make things more or less confusing depending on what the purpose of drawing the structure is. But if the question is "what is the structure, where are the C?" and a student who has taken more than the first week or two of an orgo course can't answer that correctly, he needs to go back and figure out why he doesn't remember even this most basic level of structure diagramming. Now I could WP:AGF and say "well, he's just guessing" but that's a pretty bad basis for...well, anything in science. If it really matters, it's really important to figure out what it means by the widely used standard in which it's drawn. Now all that said, this particular structure is likely viewed by lots of schoolkids and non-college students (TNT seems like a popular/common lay-reader subject), so making it more explicit is fine by me. OTOH, the immediately adjacent 3D-balls one has all C and H visible for easy comparison to help interpret the skeletal one. DMacks (talk) 18:47, 26 November 2009 (UTC)

You said:

Implied C in a skeletal formula is an IUPAC-blessed standard, not just a shorthand/jargon used by those in the field.

I am not a chemist, though I've had a few years of chemistry at university and I do come from a long line of chemists of some sort or another on my Mother's side. I understand who IUPAC are, I have my college chemistry textbooks and CRC, I do various chemical reaction work for rocket propulsion and explosive chemistry on and off.

I also do a lot of science writing for normal people, of various flavors, on and off.

There is no contradiction between implied C as a blessed standard, and it being jargon. In my opinion, both are true.

The general public who have enough experience with chemistry to know what skeletal formulae look like can be expected to "get" that there's carbon there where the lines join. But a random sampling of 3 educated people last night (one biochemist/neurobiologist, two computer scientists) were confused, though they all guessed correctly what it was.

If we are confusing educated readers, we're doing something wrong...

Georgewilliamherbert (talk) 21:21, 26 November 2009 (UTC)

In the interests of defending Wikipedia's honor (as it were), however, I did just email the professor a note including the following:

"From Leigh, Favre, and Metanomski's 1997 edition of "Principles of Chemical Nomenclature" we find skeletal formulae for benzene and related rings with attached methyl or other carbon chain groups represented as line segments (wihtout explicit "C" or "CHx") on:

pp 15, diagram 25

pp 76, diagrams 5 and 6

pp 87, diagrams 11, 12, and 13

The structural formula definition on pp 11 explicitly allows this:

"In organic chemistry, structural formulae are frequently presented as condensed formulae. This abbreviated presentation is especially useful for large molecules. Another way of presenting structural formulae is by using bonds only, with the understanding that carbon and hydrogen atoms are never explicitly shown."

Pointing out that IUPAC allows this, and yet still using a diagram which more people will immediately understand, are not contradictory.

Happy Thanksgiving, everyone! Georgewilliamherbert (talk) 22:27, 26 November 2009 (UTC)

Thanks for that. Please keep us updated? --Rifleman 82 (talk) 02:29, 27 November 2009 (UTC)

In Wikipedia:Manual of Style (chemistry)/Structure drawing it says

• The use of explicit methyl groups in the following cases is a stylistic choice, and both forms are generally acceptable on Wikipedia:
  • methyl groups attached to a ring or as branches in a longer carbon chain;
  • methyl groups at the end of a carbon chain.

So it seems to be down to the editor's choice. I usually keep them in, unless the molecule is so big/complex that they get in the way.  Ronhjones  ^(Talk) 23:03, 26 November 2009 (UTC)

Google blurb error

When I search trinitrotoluene the wikipedia header summary has the formula wrong. It's the only place I see the error and it's the omission of the parens and everything inside them. I don't know much about HTML protocols but it may be that the computer is reading the parens as a comment and thus hiding it. Does anyone know how to enter this information so this omission doesn't occur? I hope this entry makes sense. —Preceding unsigned comment added by Alanyostsj (talk • contribs) 06:28, 17 June 2010 (UTC)

Efficient Concussion

This line was written with the assumption that the reader knows what it means; It should be expanded to explain the meaning (or linked to an explation). (It seems to mea if you hit it with a hammer, the stuff will blow up.)174.25.42.71 (talk) 20:49, 22 November 2010 (UTC)A REDDSON

Correct Chemical Formula

Just so everyone knows, the given image with the skeletal formula is quite wrong. You forgot the CH3. There are many images that have the complete formula. —Preceding unsigned comment added by 178.191.191.13 (talk) 02:00, 13 December 2010 (UTC)

It's a perfectly standard formula as per Wikipedia:Manual of Style (chemistry)/Structure drawing - the showing of explicit methyls is a stylistic choice.  Ronhjones  ^(Talk) 01:29, 19 January 2011 (UTC)

Dynamite?

The line divorcing dynamite from TNT is not Quite correct. Most military dynamite Is TNT (no commercial is, though.)70.176.118.196 (talk) 01:45, 25 March 2011 (UTC)

Poor Oxygen Balance?

Something should be mentioned regarding why TNT is often blended with an oxidant. It is because it has a low oxygen balance, that is, when TNT detonates it either leaves some unburned carbon or some unburned methane gas. This is seen as a black cloud and/or yellow flames on a TNT detonation. Composition "B" contains some RDX, a positive-oxygen-balance explosive that provides a little extra oxygen, to help TNT's efficiency.70.176.118.196 (talk) 01:45, 25 March 2011 (UTC)

WWII?

TNT was rarely used in WWII. Except for some demolition work. i.e, military dynamite, RDX and PETN were mostly used. TNT was the mainstay of WWI.70.176.118.196 (talk) 01:45, 25 March 2011 (UTC)

The NFPA 704 diagram is wrong

TNT must be heated greatly, or have a strong initiation source to explode. It melts at 82C and explodes at a higher temperature. This puts it at 3 for instability, and at 1 (or maybe 2 if the ignition temperature is less than 93C) for flamibility. Why does it say 4 for both! — Preceding unsigned comment added by 11cookeaw1 (talk • contribs) 04:30, 9 April 2011 (UTC)

• This sounds like a flip answer, but as a professional chemist, I am being completely serious. NFPA diagrams are created and applied by bureaucrats, not chemists nor explosives professionals. Everyone knows that TNT is dangerous, right? So clearly, it must represent a very large danger. A little less cynical, the NFPA diagrams reflect what might happen, and in a fire, TNT is clearly a major hazard. A documented plant explosion was caused by a worker tossing a cigarette butt that caused a burlap sack containing TNT to smoulder, resulting in a fire and subsequent explosion (See Urbanski, Chemistry and Technology of Explosives). Because TNT melts at below the boiling point of water, it can be present as liquid in a water-doused fire situation; the liquid is flammable in the presence of absorbative material (cf Candle). The "4" ratings are probably excessive, but considering the consequences of a fire and explosion, not entirely unwarranted. Norm Reitzel (talk) 13:11, 2 August 2011 (UTC)

Force

Im looking this up for a school project and couldnt find how much force is exerted can any body help me? — Preceding unsigned comment added by 74.195.11.217 (talk) 16:13, 3 December 2011 (UTC)