Sciencemadness Discussion Board - chemiluminescence!!

chemiluminescence!!

Alexein - 27-10-2008 at 12:49

Hey all, after many failed attempts i was able to make chemluminescence with bis(trichlorophenyl) oxalate, some 9,10-bis(diphenylethynyl)anthracene dye and H2O2 and diethyl phthalate solvent. Sprinkle a bit of sodium acetate on top...

Synthesizing TCPO was a bitch....

Here it is with the lights on.

[img]http://www.xtremesystems.org/forums/attachment.php?attachmentid=87795&stc=1&d=1225084323[/img]

Lights off
[img]http://www.xtremesystems.org/forums/attachment.php?attachmentid=87796&stc=1&d=1225084323[/img]

The crystals in the bottom are *pure* TCPO. Hard to see, but you can tell that the the crystals themselves aren't glowing, but the surface is as the TCPO dissolves into the solvent and reacts.

there is enough in there to last a month (really, i've measured).

Picric-A - 27-10-2008 at 13:04

Nice work!! looks awsome!
Can you explain how you made your TCPO? seems interesting! i wana try!

Jor - 27-10-2008 at 13:13

React oxalyl chloride with trichlorophenol.

Oxalyl chloride is very expensive. You need PCl5 or TCT to make it. PCl5 hard to get and with low yields. TCT cheap, hard to get, but also very toxic.

Alexein - 27-10-2008 at 13:35

Start with 2,4,6-trichlorophenol and dissolve it in dry toluene or dry dichloromethane. "wet" solvents are ok but the yield will be reduced. Add one molar equivalent of a suitable organic base. I used triethylamine. stir until everything is dissolved.

chill the solution with ice and add in SLOWLY 0.5 mol equivalents of oxalyl chloride. Its going to heat up.... ALOT... so keep it stirring and chilled.

Once its all added remove the ice and let it warm to room temperature with continous stirring. I find purity increases if you let it stir overnight.

The TCPO is a fine white powder mixed with triethylamine hydrohloride at this point. Suction filter the mixture and keep the suction on to dry out the powder. Discard the filtrate.

pour water directly onto the white powder and wash out the triethylamine hydrochloride. Dry the powder again.

The powder is TCPO, its still pretty impure but usable. If you want nice big pure crystals (like the ones in the picture) you can dissolve TCPO in tetrahydrofuran, filter, and recrystalize.

Silverado7 - 27-10-2008 at 13:36

It's so beautiful... Great work!
Fascinating...

Picric-A - 27-10-2008 at 13:43

Thanks, will give that a try!
I will probably buy a small amount of Oxalyl chloride. It isnt THAT expencive... but its gonna be worth it

The only real chemiluminescence i have done is oxidation of luminol, TCCA + H2O2 and NaOH/H2O2 + Cl2... and they are boring

Alexein - 27-10-2008 at 14:57

I should also mention a couple of things:

I *STRONGLY* reccomend the solvent that you do your chemiluminescent reaction in be diethyl phthalate. The reaction is MUCH brighter and lasts MUCH longer than if you do it in tetrahydrofuran or acetonitrile. Other solvents don't even work.

DEP is also relatively non-toxic and fairly inexpensive.

Trichlorophenol is a known carcinogen. While this doesn't stop most of us here on science madness do please take precautions.

A list of good dyes to make all kinds of funky colors can be found in http://en.wikipedia.org/wiki/Lightstick I've personally tested BPEA (which is seen in the pictures) and DPA.

Ozone - 27-10-2008 at 16:00

I really like this one, it's a classic.

I have made this reaction work fine in EtOAc (although the yield and duration of light is minimal) using DNPO, bis-dinitrophenyloxalate. I used either perylene (expensive, turquoise) or rhodamine 6G (cheap, red-orange) for the dyes.

If you want your TCPO reaction to be its best, add some sodium salicylate (this is not required with DNPO because the higly EW DNP rings are good leaving groups).

Both dioctylphthalate (DOP) and the bis-2-ethylhexyl (frequently confused with DOP) analogue also work.

The reaction is carried out in toluene; you can add excess toluene and azeotrope out the water with a short forerun. This is essential when making DNPO with DNP, which is sold containing considerable water to reduce the risk of explosion (it is both toxic and potentially explosive; it goes right through nitrile gloves). Cool, then add the oxalyl chloride (mine says it can contain <0.5% phosgene). After a short induction period, the mixture outgasses. Close and stir overnight.

Take off the solvent and bring up the residue in chloroform. Filter this and retain the solid. Mine worked fine (as a chemiluminescent probe) as-is. Make sure all of the chloroform is removed b/c it will quench your phosphorescence.

Also, oxalyl chloride in EtOAc with dye and added H2O2 will also work. The esterification only serves to make the oxalyl moiety easier to handle.

Cheers,

O3

Alexein - 27-10-2008 at 16:22

Yeah, Sodium Salicylate works too.

I used sodium acetate because it was onhand. It works just as well IMHO.

Now comes in blue

Alexein - 29-10-2008 at 16:49

Same chemiluminescent reaction but with 9,10-diphenylanthracene to give a blue color.

Lights on.
[img]http://www.xtremesystems.org/forums/attachment.php?attachmentid=88027&stc=1&d=1225323034[/img]

Lights off.
[img]http://www.xtremesystems.org/forums/attachment.php?attachmentid=88028&stc=1&d=1225323034[/img]

I like this one better cause you can see the crystals and the "glow layer" as they dissolve.

bfesser - 29-10-2008 at 19:07

Why 2 vials?

Alexein - 29-10-2008 at 20:15

Old saying: "why not?"

The dyes stain BADLY and the trichlorophenol waste is a known carcinogen. Also, as the reaction progresses, carbon dioxide is produced and tiny droplets that were stuck on the rim of the cap push out around the vial and get on the outside.

i left some vials around (singles) for a month and when i picked them up some of the contents had leaked out to the outside and onto my hand. I was not too happy that a carcinogenic substance that's proven to go through skin was on me.

So I double vial. haven't had a single accident since. One of my older samples had leaked out but the spill was entirely contained within the outer vial.

[Edited on 10-30-2008 by Alexein]

Klute - 30-10-2008 at 09:09

Very beautifull! Pretty impressive, the pictures are really well taken.

I agree with you for the douible-vial. Never too precautious.
It's a pity oxalyl chloride cna't be reaplace dby soemthing more easily obtained.

JohnWW - 30-10-2008 at 09:46

A very good do-it-yourself means of emergency lighting without electricity or fuel. And just in time for Halloween, too.

Alexein - 30-10-2008 at 10:07

Yeah, I got enough stuff here to fill a 20 gallon plastic bucket.

I'm going to load it up with the green stuff, put a radioactive label on it, cart it around my school and scare the crap outta my buddies and my teachers

Sure its freaking expensive.... but its going to be so worth it.....

UnintentionalChaos - 30-10-2008 at 21:24

Any reason for the use of dinitrophenol and not say, picryl groups? I imagine the picryl would be a much better leaving group, no? Would the reaction proceed too quickly because of this? Is the picric acid strongly colored enough to interfere? Or would the threat of explosion make it not even close to worth it?

What about home-brew tribromophenyl oxalate? IIRC tribromophenol is astoundingly easy to make. The oxalyl chloride not so much.

Alexein - 31-10-2008 at 07:29

I think explosion danger is an issue. In theory the picryl groups would work very well.

I made the trichlorophenol derivative cause i knew i would bung up my first few attempts and i didn't want to have any possibility of explosions from my screw ups.

I suppose tribromophenol would also work. The reaction works with just straight phenol so anything better than that would have to work.

Getting the oxalyl chloride was the expensive part. But easier for me than making/handling PCl5 or cyanuric chloride precursors.

Alexein - 5-11-2008 at 13:09

This awesome paper details instructions on how to make a great deal of chemiluminescent reactions, not just peroxylates.

Chances are, if you can't obtain materials for one type you might be able to get materials for another type.

equally awesome is that it details mechanisms for how each one works. (or at least what the best proposed mechanisms are.)

Its a must have for anyone interested in chemiluminescence.

[Edited on 11-5-2008 by Alexein]

Attachment: Demonstrations of Chemiluminescence.pdf (1.4MB)
This file has been downloaded 7171 times

Klute - 5-11-2008 at 14:48

Thank you very much! Indeed a very complete and informative paper!

Alexein - 25-11-2008 at 21:27

I know i'm kicking a dead horse by reviving this thread but i wanted to post a video of TCPO crystals i made.

<object width="425" height="344"><param name="movie" value="http://www.youtube.com/v/cVQ9jjdU0l8&hl=en&fs=1"></param><param name="allowFullScreen" value="true"></param><param name="allowscriptaccess" value="always"></param><embed src="http://www.youtube.com/v/cVQ9jjdU0l8&hl=en&fs=1" type="application/x-shockwave-flash" allowscriptaccess="always" allowfullscreen="true" width="425" height="344"></embed></object>
Plenty of chemiluminescence videos out there. But i don't think any of them have crystals *that* big.

Sorry for the picture quality.

[Edited on 11-26-2008 by Alexein]

Klute - 26-11-2008 at 02:13

Very nice!

Ozone - 26-11-2008 at 22:51

The picryl moiety (TNPO) may be too good of a leaving group. The DNPO works without the salicylate (or acetate) promoter because it is a better leaving group than TCP. DNPO is also much less stable on storage (stored dry, under N2 or made as needed).

I imagine that TNPO would be even more unstable leading back to picric and oxalic acids (the explosive hazard should not exceed that of picric acid*, unless metals are present).

*dry picric acid can be a bit "hairy".

Cheers,

O3

raiden - 27-11-2008 at 22:47

That stuff is BEAUTIFUL! I will have to give it a go if I can procure the supplies.

Alexein - 28-11-2008 at 07:22

Quote:

Originally posted by raiden
That stuff is BEAUTIFUL! I will have to give it a go if I can procure the supplies.

Post pictures if you can.

You planning to make your own oxalyl chloride or buying it?

I'm currently scrapping together enough cash to get more chemicals and make more of the TCPO. I'll post a full video of how to do it eventually.

[Edited on 11-28-2008 by Alexein]

Formatik - 13-2-2009 at 20:58

I've found two videos, both are quite interesting. The first is description of the method also using TCPO, NaOAC, BPEA dye, and 30% H2O2, but using EtOAC as a solvent. Then the second is a scale-up done in a 2 L pop bottle:

http://www.youtube.com/watch?v=kH19EIf5GtE

http://www.youtube.com/watch?v=mUCdGMeTveM

Sedit - 13-2-2009 at 21:39

Question Alexein,....or who ever may have the needed information.
Can these type of chemiluminescence have the ability to be used in a laser?

It would boil down to how many excited stated the molecule has.
Does it have just the lower state or is there a higher state that it can achieve and the drop to the lower to release the photon... if that makes sence

I know there are chemical laser being used by the military by these are excited dimmer lasers that are mostly useful for FIR.

BTW Nice work, glow sticks and such always where my favorite.. but that may be cause of all those years being chemicaly confused in clubs.

Alexein - 14-2-2009 at 15:45

Quote:

Originally posted by Formatik
I've found two videos, both are quite interesting. The first is description of the method also using TCPO, NaOAC, BPEA dye, and 30% H2O2, but using EtOAC as a solvent. Then the second is a scale-up done in a 2 L pop bottle:

http://www.youtube.com/watch?v=kH19EIf5GtE

http://www.youtube.com/watch?v=mUCdGMeTveM

O_o

o_O

Those are MY videos!!!

I find it hilarious ya found them.

I didn't post them here since i wanted to wait until i had a video on synthesis of TCPO.

Ah well, cat's outta the bag now

Quote:

Originally posted by Sedit
Question Alexein,....or who ever may have the needed information.
Can these type of chemiluminescence have the ability to be used in a laser?

It would boil down to how many excited stated the molecule has.
Does it have just the lower state or is there a higher state that it can achieve and the drop to the lower to release the photon... if that makes sence

I've thought of that too. But to be honest, i really don't know. A population inversion needs to be obtained but i don't think it's possible to pump enough dye molecules fast enough to obtain one.

But i'm not an expert on lasers, might be doable.

Hats off to anyone that can.

[Edited on 2-14-2009 by Alexein]

Sedit - 14-2-2009 at 19:26

Im not to bad with lasers and I answered my own question through a little searching. The short answer is no.

Now there may be a possibility of this being capable of being pumped by a short pulse TEA or eximer laser but alot of that depends on wether or not the fluid is transparent to the wavelength that the higher state generates...

Point being even if so there are easyer ways to go about generating this sort of laser and population inversion would just be to hard if not impossible because I feel these may want to stay in the lower energy level for to long amount of time kind of like phosphor substances.

Formatik - 15-2-2009 at 12:54

Quote:

Originally posted by Alexein

O_o

o_O

Those are MY videos!!!

I find it hilarious ya found them.

I didn't post them here since i wanted to wait until i had a video on synthesis of TCPO.

Ah well, cat's outta the bag now

The irony of it all. Well, you can always repost since I didn't find out how to embed them properly. They'll be discovered a second time. Anyways, that soda bottle is one phat glowstick. It puts all the glowstick wannabes to shame.

a_bab - 1-6-2009 at 04:44

Would pentachlorophenol work instead of trichloro?

Does anyone have a synth for the oxalyl chloride (starting from PCl5 and oxalic acid)? It sounds like a dangerous reaction to me.
LATER EDIT: Thanks to Sauron and others I found out it can be done fairy easy. Not something for indoors though, unless having a *good* fumehood. 50% doesn't bother me; I only need a few grams.

And Alexein, where did you get the TCPO synth from? What other phenol derivatives could work?

[Edited on 1-6-2009 by a_bab]

UnintentionalChaos - 1-6-2009 at 10:29

Quote: Originally posted by a_bab

Would pentachlorophenol work instead of trichloro?

Skimming the interwebs,

Pentachlorophenol:
pKa=4.74

2,4-dinitrophenol
pKa=4.08

This suggests that yes, you probably can use pentachlorophenol, although as mentioned earlier, the trichlorophenol has some advantages over the dinitrophenol, which this would be similar to.

[Edited on 6-1-09 by UnintentionalChaos]

Formatik - 1-6-2009 at 22:50

Here's some compounds that produce chemiluminescence 1 to 1.4 times more intensely than luminol: http://cat.inist.fr/?aModele=afficheN&cpsidt=827324

I wonder if p-phthalic acid (from PETE) can be nitrated to also yield a chemiluminescent compound after similar treatments as with nitro-o-phthalic acid.

Rich_Insane - 2-6-2009 at 21:58

I'm just curious of how this mechanism works. Obviously what happens is a photon is given off somewhere in the reaction of a low wavelength, but what is the reaction?

According to here it's like:

So what's going on is that the part connecting the trichlorophenols is folding in on itself, then that byproduct reacts with the fluorophor (the anthracene dye) to give off light in the form of a photon.

Basically the ring-like molecule is exciting the fluorophor.

Am I right?
[Edited on 3-6-2009 by Rich_Insane]

[Edited on 3-6-2009 by Rich_Insane]

The Fountain of Discordia - 3-6-2009 at 14:36

Quote: Originally posted by Alexein

Quote:

O_o

o_O

Those are MY videos!!!

If that be the case, I owe ya thanks. Until I rediscovered my interest in chemistry, I had no idea of what I wanted to do in life. Your videos helped rekindle that interest.

Ozone - 3-6-2009 at 16:40

IIRC, the peroxide oxidizes the TCPO to yield the dioxetane which spontaneously decomposes to yield 2CO2 and hv (which is in the UV range). The UV-hv excites the fluorophore and the resulting emission is visible.

If you balence the equation you will find the staight oxalyl chloride will work just fine. The diester is just to make it easier to handle/store. I have tested it with straight oxalyl chloride and it works fine.

Cheers,

O3

Rich_Insane - 3-6-2009 at 20:01

Thanks!

The reaction is beautiful; Is this the reaction used in most glowsticks?

The main barrier for me is TCPO, but how would one obtain the anthracene dye? Is it a common flurophor? Can others be used, since the light is emitted directly from the reaction?

a_bab - 3-6-2009 at 21:07

Read the whole thread:http://en.wikipedia.org/wiki/Lightstick (dyes listed).

Even rhodamine G would work.

How To Make TCPO

Alexein - 3-6-2009 at 23:12

Hi guys

Here's how to make TCPO:
(I can't seem to embed the video though.)

http://www.youtube.com/watch?v=ViJknvEEEOA

Sorry for the late update, i've been busy.

[Edited on 6-4-2009 by Alexein]

Jor - 4-6-2009 at 08:11

Very interesting.
I want to make this sometime as well. As soon as I have enough money I will buy 25mL of oxalyl chloride.

I however, want to avoid the trichloropehnol as it is very environmentally unfriendly and a carcinogen.
So I need 2,4-dinitrophenol. At the moment I can buy 25g of 2-hydroxy-3,5-dinitrobenzoic acid cheaply. Will this decarboxylate easily, by heating with NaOH or something else?

Ozone - 4-6-2009 at 16:11

I'd rather work with TCP. It's less toxic. 2,4-DNP is nasty stuff that can decouple electron transport after dermal absorption...after it has gone through your gloves.

I made DNPO as a fast chemiluminescent probe, and it works well-But-the nitro groups make the rings much more electron withdrawing and this makes the compound far more labile. This is good (for a probe), because it is fast and does not a require salicylate (or other) kicker. This is bad because it is not as stable on storage. It glows brighter than TCPO, but for less time.

And your waste is a very nice acute poison that is probably also hell on plants.

Either works, take care,

O3

garage chemist - 5-6-2009 at 00:43

Jor, the 2,4-dinitrophenol is made by nitrating chlorobenzene to 2,4-dinitrochlorobenzene (see Gattermann or other organic chemistry lab book) followed by refluxing in NaOH solution until homogenous.
Acidifcation then directly precipitates the dinitrophenol.

a_bab - 5-6-2009 at 23:50

Some questions:

1. is there a specific, "official" synth for TCPO? (a link to a doc, or a reference). I'm interested in this as I'd rather work with 2,4 DNP witch I already have (as an indicator); I hate the idea of working with carcinogens like halogenated phenols (I have access to pentachloro-phenol). So maybe there are safer alternatives. Would TNP work?

2. as for the solvent where the chemoluminiscent reaction takes place, can it be reused? Maybe distilled?

Ozone - 6-6-2009 at 12:27

Pick your poison:

2,4,6-TCP LD50 (oral, rat): 820 mg/kg (http://msds.chem.ox.ac.uk/TR/2,4,6-trichlorophenol.html); anticipated carcinogen (Merck).

pentachlorophenol LD50 (oral, rat): 146 mg/kg, may be absorbed through skin, more toxic in solvent (Merck). "Clear evidence links PCP exposure with carcinogenic activity in test mice. Limited evidence links PCP with carcinogenicity in humans. One study links PCP with Hodgkin's disease on the basis of a single family's case history and with the occurrence of the disease in carpentry and lumber workers in the United Kingdom (7). The World Health Organization publication cautions against the any conclusions based on such limited data"(http://pmep.cce.cornell.edu/profiles/extoxnet/metiram-propox...).

2,4-DNP LD50 (oral, rat): 30 mg/kg, readily absorbed through intact skin (Merck). Lowest published lethal dose: 4.3 mg/kg (http://msds.chem.ox.ac.uk/DI/2,4-dinitrophenol.html).

Cheers,

O3

Jor - 6-6-2009 at 16:56

How could trichlorophenol be synthesised? It indeed seems safer than 2,4-DNP, although the latter is used by bodybuilders in quite high doses to boost their performances. So a little should't harm, but well I will go for TCP.
I'd like to start from salicylic acid if possible, but if needed I can also use phenol.

I have been thinking of buying all the things I need in a few months. 25mL oxalyl chloride (Aldrich, 20 EUR), 100 or 500mL triethylamine (Acros, the 500mL is only 7 EUR more expensive). Can anyone name some other interesting uses for wich i can use triethylamine? Otherwise I just buy 100mL as I don't like buying excess amounts. Toluene, I need to buy that as well. Can this be dried by refluxing over sodium?

The dye is the biggest problem. The only cheap suitable dye is Rhodamine B wich gives a red chemiluminescence. Is this just as bright as the one in the video?

The solvent diethylphtalate might be porblematic. I will have to make it myself from ethanol and phtalic anhydride. Is a catalyst needed, like H2SO4 or p-toluenesulfonic acid ?
Or I could ofcourse use ethyl acetate, but it is said to perform less well and for a shorter time.

And can trichlorophenol be effeciently destroyed? It's tricky to bring it in as waste, as it will be burned and I don't think the trichlorophenol will burn and thus enter the environment.
Would the boiling in NaOH-trick replace one or more chlorine's by -OH ?
Or maybe a very strong reducer will do the trick? I have some pretty good ones including hypophosphite.

[Edited on 7-6-2009 by Jor]

UnintentionalChaos - 6-6-2009 at 18:28

TEA is a great general purpose base for mopping up acid formed during reactions. I wonder if pyridine (Which I know you own) would be an acceptable substitute in this case. Probably. It may even improve the reaction by forming an intermediate N-acyl pyridinium species.

Burning of TCP would generate chlorinated dibenzodioxins, so that is completely out of the question. Skimming around, it looks like fenton's reagent is not terribly effective on chlorophenols. Perhaps fusion with NaOH/KOH eutectic is in order.

[Edited on 6-7-09 by UnintentionalChaos]

Alexein - 7-6-2009 at 03:05

Quote: Originally posted by a_bab

Some questions:

1. is there a specific, "official" synth for TCPO? (a link to a doc, or a reference). I'm interested in this as I'd rather work with 2,4 DNP witch I already have (as an indicator); I hate the idea of working with carcinogens like halogenated phenols (I have access to pentachloro-phenol). So maybe there are safer alternatives. Would TNP work?

2. as for the solvent where the chemoluminiscent reaction takes place, can it be reused? Maybe distilled?

1. The reference at the end of the video is the "official" prep... although what exactly do you mean by "official"?

2. Yes, in fact i vacuum distill the solvent for reuse on a regular basis. The water bearing azeotrope comes off quickly and the solvent itself comes off after with excellent recovery.

As for the TCP vs. DNP argument, I really don't know which one is better. I used TCP because i was afraid of the lower LD50 and explosive properties of DNP. At the time i first started i wasn't confident enough in my abilities as a chemist to handle it safely. If you muck around with DNP all the time and know it like the back of your hand then go for it.

But i will say this: two years ago I made 40grams of extra large and pure TCPO crystals by careful crystalization from THF. Even today, that same sample (stored in an air-tight container) is as brilliant and potent as the day i made it. I still toss a few crystals into a fresh reaction mixture every week after hours for fun and it still reliably gives me light.

So i can attest to its stability and longevity.

Ozone - 7-6-2009 at 07:56

Here's a .zip containing 5 papers. The best one is probably Mohan's (from American Cyanamide) from 1974 (It is the one I used the first time I made the stuff).

There is some controversy surrounding the dioxetane-to-light step. In one of the papers, it appears that a dye-radical cation might exist briefly with the CO2 radical anion. While this suggests the possibility of dye stimulation via intersystem cross, it does not necessarily rule out photochemical (UV) excitation.

Hope this works, it might be too big. If it is, I'll upload a few manually.

[edit] hmm. It barfed up the zip (too big) and does not want to eat the Mohan paper, either (1.7 mb)? I'll try again.

[edit] "page not displayed". I'll try a smaller one (1.38mb).

[edit] nope, same thing. Try a smaller one yet (57.8 kb).

Cheers,

O3

[Edited on 7-6-2009 by Ozone]

Attachment: Hadd DNPO-TCPO mechanism and kinetics.pdf (58kB)
This file has been downloaded 1312 times

Ozone - 7-6-2009 at 08:23

Oh well, here are screens of the Mohan paper. Sorry about the low quality, but they will get you by.

Cheers,

O3

Ozone - 7-6-2009 at 08:31

Same problem, for the Shakhashiri 1981 paper

.

Cheers,

O3

ItalianChemist - 19-2-2011 at 12:49

The TCPO obtained still smells like 2,4,6-TCP?
I also tried it and when I added oxalyl chloride a lots of white smokes appeared...

[Edited on 19-2-2011 by ItalianChemist]

jamit - 8-3-2017 at 08:53

Does anyone know how much oxalyl chloride is needed to make TCPO, if you start with approx. 8g of 2,4,6 - TCP? I'm asking this because I have conflicting answers: Laffle on youtube list 1.7ml of oxalyl chloride whereas thomsci suggests 10ml. both start with 8g of TCP. Am I missing something? thanks.

Ozone - 9-3-2017 at 07:52

I calculate 1.74 mL.

O3

Sulaiman - 9-3-2017 at 13:03

eBay.uk does not sell the ingredients so I've no idea on pricing
but I guess that oxalyl chloride is cheaper/easier to buy than TCP,
in which case, the excess may be to force the reaction equilibrium for better TCPO yield ?

jamit - 10-3-2017 at 10:11

Quote: Originally posted by Ozone

I calculate 1.74 mL.

O3

thanks Ozone, but can I ask how you came up with that answer. I can't seem to calculate it using stoichiometry.

Ozone - 10-3-2017 at 13:35

Stoichiometry will give you the mass of oxalyl chloride. Use the density to calculate mL: 1.48 g/cc.

O3