# Xylene? Compared to Toluene?



## WaynePaulette (Mar 23, 2011)

Hey guys,

I have seen and know of a couple people using toluene in their tanks as a thinning agent for silicone. Lowes didn't have it but they do have this stuff called Xylene. No idea exactly what it is. Even as a chemistry student in my 5th year i haven't even heard of this... Any ideas?

I looked at it online and it seems like a product of toluene? No clue.

Any ideas or suggestions on whether it would act the same way as toluene or not?

Thanks,
Wayne


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## frogparty (Dec 27, 2007)

xylene is almost identical to toluene, it just has 1 more methyl group off the benzene ring. It is a mix of 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene. 
Comparable to toluene, and is used as a thinner of paints when slower drying is required. Because it exists s a 3 isomer mix, the physical properties of each isomer contribute to how it behaves as a whole.


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## james67 (Jun 28, 2008)

never heard of xylene? its commonly used in amateur chemistry as well, in the process of alkaloid extractions.

james


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## wiedemey (Jan 23, 2010)

We use xylene to prepare histology slides for immunohistochemistry. While I haven't tried it with silicone its properties as an organic solvent should be similar to toluene (at least for our purposes; organic chemists may disagree). Just be careful with these solvents; they are toxic and flammable so make sure there is enough ventilation (we only use it in a fume hood).


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## frogparty (Dec 27, 2007)

james67 said:


> never heard of xylene? its commonly used in amateur chemistry as well, in the process of alkaloid extractions.
> 
> james


I was thinking the same thing. No offense to the OP, but as a 5th year chem student you should be able to just look at its structure and know a lot about the reactivity/properties of the molecule. Im not even done with my 1st year of organic chem and I can tell a lot about it. Sholdnt you be in analytical chem in your 5th year? past p-chem, past transition metal chem?


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## WaynePaulette (Mar 23, 2011)

I'm in my 5th as a dual major. My main major is physics. Not chemistry. Currently chemistry is my minor til i finish the physics which i have a year left. The scheduling between the two sciences is nearly impossible. I looked at it more after i posted the thread. The thread was posted during a research paper break. It is basically just the combination of all the isomers which just lowers the boiling point. It is basically the same as toluene just takes a little longer to evaporate. so as long as the silicone still hardens back up it shouldnt be a problem. But yes i have only done gen chems organics and analytical. Physics is a lot more. Which is why i dont have a problem hardwiring anything. 

Thanks for the help though.

Ill have tank updates soon. I just finished the clay background and planting. Just gotta get the pictures up.


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## MichelleSG (May 1, 2010)

The fact that both of these chemicals are available over the counter really just horrifies me. I'm a chemist and I won't touch them without the right gloves (yeah, I do research to find which gloves work with the nastiest of my chemicals) and in a fume hood. Paranoid? Yes. Also not into dying of cancer at age 40.


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## WaynePaulette (Mar 23, 2011)

I wear gloves when i work with anything. Usually if it isn't toxic its disgusting. So either one usually requires gloves. haha

Yeah you can get practically anything now adays though. FisherScientific! yay!

-Wayne


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## frogparty (Dec 27, 2007)

well if you find ergotamine tartrate for sale let me know


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## james67 (Jun 28, 2008)

frogparty said:


> well if you find ergotamine tartrate for sale let me know


frogparty: dont forget some safrole. 

james


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## Ed (Sep 19, 2004)

james67 said:


> frogparty: dont forget some safrole.
> 
> james


If your worried about safrole.. then you have a very bland diet...


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## frogparty (Dec 27, 2007)

james67 said:


> frogparty: dont forget some safrole.
> 
> james


Hell yeah, mix the two products together and you have what used to be my all time favorite way to spend an evening of live music and dancing!!!


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## james67 (Jun 28, 2008)

flippin......... 

james


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## frogparty (Dec 27, 2007)

when the wood grain on the bar is more interesting than the band you went to see.......


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## Ed (Sep 19, 2004)

you can't get enough to drink.. and your mouth is all dry and pasty...


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## frogparty (Dec 27, 2007)

thats why gummi bears were invented, really stimulates saliva prodction


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## andyrawrs (Aug 16, 2008)

MichelleSG said:


> The fact that both of these chemicals are available over the counter really just horrifies me. I'm a chemist and I won't touch them without the right gloves (yeah, I do research to find which gloves work with the nastiest of my chemicals) and in a fume hood. Paranoid? Yes. Also not into dying of cancer at age 40.


Well hey if we couldn't get our hands on toluene and certain strong acids how else could we make our favorite trinitrated compound?


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## randfp (May 4, 2006)

andyrawrs said:


> Well hey if we couldn't get our hands on toluene and certain strong acids how else could we make our favorite trinitrated compound?


Here's Toluene for you...Toluene, Quart by Sea Hawk Paints


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## frogparty (Dec 27, 2007)

andyrawrs said:


> Well hey if we couldn't get our hands on toluene and certain strong acids how else could we make our favorite trinitrated compound?


gimme DInitrated indole derivatives and I wont complain either.


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## SethDoty (Feb 7, 2010)

WaynePaulette said:


> Hey guys,
> I have seen and know of a couple people using toluene in their tanks as a thinning agent for silicone. Lowes didn't have it but they do have this stuff called Xylene. No idea exactly what it is.


I worked in the petrochemical industry for several years, specifically in paint manufacturing. Xylene is a major ingredient in a large number of enamel paints and also functions as a thinner or in a clean up role for those paints. Most likely it will work fine for your application.


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## WaynePaulette (Mar 23, 2011)

Thanks lol

I'm not sure what the side conversation was about haha. I got lost and didnt feel like going back to read it all.

I had a feeling Xylene would work adequately also.

Wayne


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## Ed (Sep 19, 2004)

SethDoty said:


> I worked in the petrochemical industry for several years, specifically in paint manufacturing. Xylene is a major ingredient in a large number of enamel paints and also functions as a thinner or in a clean up role for those paints. Most likely it will work fine for your application.


It is also a solvent used to seperate carotenoids in thin layer chromatography... (At least when I was in AP Bio). 

Ed


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## frogparty (Dec 27, 2007)

I was doing IR spectroscopy with 1,2-dimethylbenzene (xylene) today


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## andyrawrs (Aug 16, 2008)

frogparty said:


> I was doing IR spectroscopy with 1,2-dimethylbenzene (xylene) today


Speaking of which (I think this was already brought up today) what are the individual effects of o-xylene & say p- & m- xylene?


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## frogparty (Dec 27, 2007)

I don't think you can obtain it as just one isomer, I believe(maybe falsly) that it is only available in the 3 isomer mix. The structural differences would cause changes in boiling point, melting point etc. but changes in reactivity would be minimal.


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## andyrawrs (Aug 16, 2008)

frogparty said:


> I don't think you can obtain it as just one isomer, I believe(maybe falsly) that it is only available in the 3 isomer mix. The structural differences would cause changes in boiling point, melting point etc. but changes in reactivity would be minimal.


Oh but I thought you had just performed spectroscopy on o-xylene (1,2-dimethylbenzene)? Maybe I misunderstand haha. Yeah I thought there'd be some physical differences...but wouldn't the placement of the second methyl group affect the subsequent direction of a third substituent? -Alkyl groups ortho & para direct on aromatic rings. So in terms of addition & substitution actions the reactivity might be a little different but for elimination it should be about the same. And I would think its use as a paint-thinner relies mostly on elimination so we're set there. But wait that doesn't actually make that much sense...haha sorry about that


*Warning: Slight Orgo-nomenclature jargon! * 
Because para-xylene (1,4-dimethylbenzene) would direct say a nitro group to be ortho to one of the methyl groups to make as a primary product 1,4-dimethyl-2-nitrobenzene whereas ortho-xylene (1,2-dimethylbenzene) would direct a third substituent to ortho or para to one of the methyls to make both 1,2-dimethyl-3-nitrobenzene & 1,2-dimethyl-4-nitrobenzene? Meta-xylene would have its own effects I think...it should only make 1,3-dimethyl-4-nitrobenzene. The second carbon in the aromatic ring won't be substituted because there's too much steric hindrance. I'm not too sure either though haha. I'm sure in terms of paint-thinning its all about the same though 

Sorry about the names, I'm a little hazy about naming at the moment

I'm just soo excited to see anything we learn in school being useful! 

P.S. Sorry for hijacking this thread! But yes I would think xylene would be an efficient silicon thinner (is that what htis thread was about again?) though I'd wear nitrile? (any suggestions?) gloves and some good ventilation.


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## frogparty (Dec 27, 2007)

Oh, I met in general it would be hard to purchase just the 1,2-dimethylbenzene. I was merely running IR SPEC on it as part of a series of IR tests with other different molecules, and learning how to further interpret IR spec readouts, especially in the thumbprint region below 1200. If you are in a lab, then yes its easy to obtain, much easier than 100%ethanol(got any orange juice?) 
Yes the placemrnt of the second methyl group absolutely affects the bonding locations of any substituents through limitation of the nucleophilic attack(I believe) limiting it to small, strong bases like the methoxide ion I think. I agree that an E2 or E1 mechanism wouldnt change that much. 
IM only in 2nd quarter O-CHEM. We havent discussed nitro and ortho yet. Im just on to alkene and alkyne reactions now. So I expect that Ill be learning benzene ring chemistry soon, with the alternating double/single bonds(I know about electron smearing, Im just saying that when we write reaction mechanisms we treat it like it actually has alternating single and double bonds)

Naming is so tedius. Why do we need IUPAC, common, AND industrial naming? its bullshit, lets just keep IUPAC and discard the need for the rest


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## Ed (Sep 19, 2004)

andyrawrs said:


> P.S. Sorry for hijacking this thread! But yes I would think xylene would be an efficient silicon thinner (is that what htis thread was about again?) though I'd wear nitrile? (any suggestions?) gloves and some good ventilation.


Nitrile should work to prevent penetration of xylene. Its been too long for me to remember the ins and outs of the chemistry. 

Ed


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## andyrawrs (Aug 16, 2008)

frogparty said:


> Oh, I met in general it would be hard to purchase just the 1,2-dimethylbenzene. I was merely running IR SPEC on it as part of a series of IR tests with other different molecules, and learning how to further interpret IR spec readouts, especially in the thumbprint region below 1200. If you are in a lab, then yes its easy to obtain, much easier than 100%ethanol(got any orange juice?)
> Yes the placemrnt of the second methyl group absolutely affects the bonding locations of any substituents through limitation of the nucleophilic attack(I believe) limiting it to small, strong bases like the methoxide ion I think. I agree that an E2 or E1 mechanism wouldnt change that much.
> IM only in 2nd quarter O-CHEM. We havent discussed nitro and ortho yet. Im just on to alkene and alkyne reactions now. So I expect that Ill be learning benzene ring chemistry soon, with the alternating double/single bonds(I know about electron smearing, Im just saying that when we write reaction mechanisms we treat it like it actually has alternating single and double bonds)
> 
> Naming is so tedius. Why do we need IUPAC, common, AND industrial naming? its bullshit, lets just keep IUPAC and discard the need for the rest


Ahhhhh okay I understand now haha my bad. Oh benzene & aromaticity reactions is an excellent chapter  It's been one of my favorites so far (but seeing as we don't learn nearly as fast or as much as a university course I'm not sure how much that means) 

When you get to benzenes, it turns out that its aromaticity (which is the "electron-smearing" you were talking about from molecular orbital theory) makes it too stable for a leaving group to completely dissociate, and the sp2 hybridization makes it too planar plus its a ring, preventing backside attack for E2. Or did I switch those two? Haha idk. 

Benzenes don't like to eliminate because they would give up alot of stability through aromaticity and the reaction would be endergonic. They like to substitute through a mechanism called Electrophilic Aromatic Substitution or occassionally Nucleophilic Aromatic Substitution...but all that good stuff is to come for you  jealous. I would think you are right that a strong base would be needed for elimination, although for substitition certain catalysts let benzenes react relatively fast with nitration or basic alkylation or acylation etc. Damn I need to read up again on Sn1 & E1 and all htat good stuff...

The class at our school doesn't do photospectroscopy until the last chapter so I really wouldn't know anything about that  We did a little something with that in AP Chem though I think...I don't remember

Haha yeah 100% ethanol would be kinda hard to get...I suppose you could distill Everclear though, lol? Which is already like 75%...not telling anyone to do so, though! 

You're so right about the naming, man! QFT. Although IUPAC is kinda a pretentious organization, and they've even made new implementations to their own system recently. (2-propanol --> propan-2-ol). Common names will always be there just like me calling facial tissues Kleenex's, it's so much more convenient sometimes. It's easier to say isopropyl alcohol than to say propan-2-ol. But industrial naming is absolutely ludicrous. 

lol that orange juice comment made me crack up. It reminded me of a certain fungi forum and certain teks...


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## frogparty (Dec 27, 2007)

I used to be a mod for a certain fungi forum several years ago...good times


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