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Ethyl Acetate?

smaerd - 23-1-2010 at 14:19

Totally new here, so if I am doing it wrong let me know! I'm fairly new to chemistry and have a lot to learn. I recently purchased a chromatography column(liquid) and was thinking about doing some practicing with it. For the eluent I plan on using a Ethyl Acetate as part of a binary solvent mixture.

I used the search function perhaps I should have looked further but I got three pages of "diethyls" and plenty of other "acetates" hehe.

Buying ethyl acetate won't have the FDA at my door or anything right? Wouldn't be a big deal but I just don't wanna get arrested for buying chemicals or something stupid.

How do people run columns with this when it costs 5 dollars per 30 mL?

I've looked into 'synthesis' and it seems really easy, however no distillation apparatus is available

. I was told it is a main constituent in some non-acetone nail-polish removers, but it appears there are many other compounds which could dirty up the whole reason of running a column.

Any ideas on how/where to procure relatively cheap, fairly pure ethyl acetate for the at home experimenter? :cool:

Thanks so much!

[Edited on 23-1-2010 by smaerd]

[Edited on 23-1-2010 by smaerd]

entropy51 - 23-1-2010 at 14:50

The FDA wouldn't care if you filled your swimming pool with EtOAc. I think you have FDA confused with DEA. I doubt DEA would care either. Local cops, well...

You can find a cheaper source than $5 per ounce, for sure. Many threads here have mentioned companies that sell to individuals, at least sometimes. Spend some time looking at old threads.

If you want to make it, you will have to distill. Enter the phrase "preparation of ethyl acetate" in google and lots of preps come up. It is a favorite experiment in college chemistry.

Magpie - 23-1-2010 at 14:55

Quote: Originally posted by smaerd

Buying ethyl acetate won't have the FDA at my door or anything right? Wouldn't be a big deal but I just don't wanna get arrested for buying chemicals or something stupid.

How do people run columns with this when it costs 5 dollars per 30 mL?

Why whould the FDA care? You need to get your three letter agencies straight.

$5/30mL? That's redickerous! Who sells it for that?

Welcome to ScienceMadness.

smaerd - 23-1-2010 at 16:24

Thank you for such prompt replies! An active community, excellent!

Who sells EtOAc for 5/30mL -> ebay fails.

Ahhh so 'Preparation' is more likely the proper word for what I have been seeking. I knew synthesis didn't sound right. Thanks for the tip!

DEA, FDA, it's all the same to me. A big group of people taking my tax dollars assuming I can't make decisions for myself.

Thanks for the welcome! I have a feeling I will learn a lot here. It feels homely

.

Off to do some research. Zoooom

Namaste.

entropy51 - 23-1-2010 at 16:57

Quote: Originally posted by smaerd

DEA, FDA, it's all the same to me. A big group of people taking my tax dollars assuming I can't make decisions for myself.

Well. I sorta think someone who doesn't know how to make EtOAc probably shouldn't presume to decide which medications he should be allowed to put into his body if he gets sick. Before there was an FDA people died from taking "medicine" sold in the stores.

You seem rather proud of your ignorance. I'm guessing that with that 'tude that you will fit right in here.

[Edited on 24-1-2010 by entropy51]

smaerd - 23-1-2010 at 17:31

Hey hey hey, let's not get super judgemental about someone we don't know anything about. I am not proud of my ignorance, I apologize for making such a generalized statement.

I never said I didn't know how to make it I said I don't have the equipment at home and was wondering if maybe someone had another way.

But thanks again, much love, I'm here to learn that is all. If I am wrong please correct me, I stand by this

.

[Edited on 24-1-2010 by smaerd]

starman - 23-1-2010 at 19:16

Ethyl acetate can be had commercially at fairly reasonable prices.I think I paid about $70-$80 for 5 litres.That was part of a 2 pack system for bostik rubber adhesive,and was purchased in Australia,where everything seems to be twice the price.
However if you're serious about getting into chromatography,you either need the means to purify commercial grades(distillation apparatus is a must) or you shell out for analytical grade solvents.

crazyboy - 23-1-2010 at 19:25

http://store.hvchemical.com/browse.cfm/4,90.html

rrkss - 28-1-2010 at 21:15

Ethyl Acetate is easy to prepare but until you know a little about organic chemistry lab technique, I'd stay away from the synthesis since you will be working with concentrated acids at higher temperatures. To buy it should not be that difficult. Take a look at sources such as ebay and such. Its not a controlled chemical and has many uses such as nail polish remover and adhesive remover to name a couple. Heck I use it at home to remove the glue residue from labels I've peeled off of containers.

rrkss - 29-1-2010 at 21:44

In case you are interested and up for the challenge I'm gonna post my preparation of ethyl acetate. I did this reaction small scale today but you can scale up accordingly.

In a 100 mL roundbottom, I added one boiling stone. Following this I added the following reagents.

30 mL of 95% acetic acid
22 mL of 95% ethanol
1 mL of 96.5% Sulfuric Acid

I proceeded to reflux that for one hour.

After the reflux I let the roundbottom cool. Then added a 300 mm vigruex column and fractionally distilled the product out of the reaction flask.

You get 3 fractions. The first fraction comes over around 74 C depending on your altitude. This fraction is ethyl acetate + any residual unreacted alcohol. Your second fraction is water which comes over around 100*C and your last fraction is acetic acid.

Obviously you stop the distillation when the second fraction starts to come over.

Then I took the product and did a workup with 10 mL of satuarated Sodium Bicarbonate Solution. As expected, I did not have any residual acetic acid in the product evidenced by lack of bubbling. Then I did another workup with 10 mL of saturated CaCl2 solution in a seperatory funnel to remove any residual Ethanol (you can substitute a type 4A molecular sieve for this step). Then I dried my product with anhydrous copper sulfate and put it into another 100 mL roundbottom with a boiling stone for distillation.

After a second distillation, I had 27 mL of ethyl acetate which is about an 80% yield. My yield probably was higher but I did lose some product in the workup due to ethyl acetate's slight solubility in water.

entropy51 - 30-1-2010 at 07:51

rrkss, what was the boiling range on the second distillation? Thanks.

80% isn't bad on this scale!

rrkss - 30-1-2010 at 09:27

I did not put a thermometer in the simple distillation when I purified the compound after drying so I can't tell you but if I had to guess it would have come over at around 75 degree Celsius.

[Edited on 30-1-2010 by rrkss]

MagicJigPipe - 30-1-2010 at 14:04

There is a company in my area that sells EtOAc. The only problem is the smallest size is 5 gallons. I have "sold" some (really just acted as a middle-man) before to a member and it worked out fine. It's been a long time so I can't really remember the price but I know it was pretty cheap ($40-$50 for 5 gallons?)

I'm not sure if I'll do it for someone that is new here but...

If you just look around you will find something. And, if you want I'll give you their phone number. They will ship to other states for a reasonable fee (but I'm not sure if they can say, take a credit card over the phone; you would need someone to give them the cash).

[Edited on 1-30-2010 by MagicJigPipe]

smaerd - 31-1-2010 at 11:05

Thanks so much for the offer. The experiment kind of failed, so this is no longer near urgent. However in the future I may need to ask for that number! That's a very good price.

User - 10-2-2010 at 09:57

Quote:

In a 100 mL roundbottom, I added one boiling stone. Following this I added the following reagents.

30 mL of 95% acetic acid
22 mL of 95% ethanol
1 mL of 96.5% Sulfuric Acid
[Quote]
I proceeded to reflux that for one hour.

After the reflux I let the roundbottom cool. Then added a 300 mm vigruex column and fractionally distilled the product out of the reaction flask.

You get 3 fractions. The first fraction comes over around 74 C depending on your altitude. This fraction is ethyl acetate + any residual unreacted alcohol. Your second fraction is water which comes over around 100*C and your last fraction is acetic acid.

Today i did the same synthesis with slight adjustments.

70ml 80% acetic acid.
50ml 96% EtOH (distilled from raw source, not really pure)
2.2ml 98% SA
2.0gr Sodium acetate (anhydrous)

All the reagents where added to a 250 ml erlemeyer.
This was refluxed at boiling point for 30 min under heavy stirring.
Heat turned off.

Next, the reflux condenser was swapped for a vigreux (70cm).
A normal distillation set-up was build.
The heat was turned on and solution brought to boiling.

The first liquid came over at 68 degrees C.
Around 100ml of product was collected.
The heat was turned off when the temp in the head dropped.

100 ml of near saturated NaCl/tap water was prepared.
50 ml of this solution was added to the collected product in a sep. funnel.
The funnel was turned up side down degassed etc.
This was done one more time with the rest of the NaCl solution.

The Ethyl acetate was left over night in a desiccator.
A total of 65ml where obtained.

-The yield isnt bad considering the amount of water present in the reaction.
-The sodium acetate was added as an attempt to suck up moisture.
I might try to saturate the solution with it next time.
Considering this is such a cheap chem it could be used to up the yield where low % acetic is available.

*edit*
Sorry I forgot to mention that it EA did not respond to a test with sodiumbicarbonate.
Lol , somehow I like the smell.

[Edited on 10-2-2010 by User]

bbartlog - 10-2-2010 at 10:13

But your sodium acetate will react with the sulfuric acid (yielding sodium sulfate and acetic acid), so you have to add excess acid or else just start with the sodium sulfate. In the reaction you just did, you would have had ~4g of H2SO4 (~40mmol) and ~25mmol of sodium acetate, so at least you didn't neutralize all your acid. The sodium sulfate that is produced does take up water, but only below 30C (so it's not an effective way to remove water from the reaction as it takes place...). If you want to dehydrate I'd go with MgSO4 or CaSO4 instead of sodium acetate / sodium sulfate.

rrkss - 10-2-2010 at 10:43

Quote:

100 ml of near saturated NaCl/tap water was prepared.
50 ml of this solution was added to the collected product in a sep. funnel.
The funnel was turned up side down degassed etc.

This is counterproductive as you loose product unneccessarily washing it with water. I only do a wash with bicarbonate because my reagent in excess was Acetic Acid.

I dry my product with 4a molecular sieves (absorbs ethanol and water). The sieves can be regenerated in an oven after the organics have first been evaporated off (to prevent an explosion). You can substitute 3a molecular sieves but you won't remove the ethanol only the water.

I agree with the previous poster, remove the sodium acetate. You are only destroying your catalyst with that and not really removing water. You still got product which was great. I like the smell of the ester as well.

entropy51 - 10-2-2010 at 10:45

Quote:

The first liquid came over at 68 degrees C.

What was the boiling range? EtOAc boils at 77 C. There are binary and ternary azeotropes with H2O and EtOH at about 70 C. The usual prep is to wash the crude distillate with saturated CaCl2 to remove H2O and EtOH (as rrkss did) and then redistill, collecting the fraction near 77 C. EtOAc tenaciously holds H2O and yours my still be wet. But maybe that's OK for your uses.

User - 10-2-2010 at 11:02

Yep thanks for the reply's.

That temp surprised me as well, the ratio of the collected product was +/- 60/40 ethyl acetate/EtOH
Ill take the boiling point as a double check.

I will do a second distillation run and see how much product i will obtain.
This stuff i cheap as dirt for me so.

Plenty of CaCl2 and anhydrous NaCO3 lying around.
Ill dehydrate the ethyl acetate and do some measurements.

*edit*

Can someone tell me why the acetic acid itself doesn't catalyse the reaction?

[Edited on 10-2-2010 by User]

rrkss - 10-2-2010 at 11:23

Another thing is to run your reflux a little bit longer. 30 minutes will give you some product but not at its full potential. At least an hour though the industry standard is 4 hours. This is organic chemistry and organic reactions do tend to run slower than most of their inorganic counterparts.

User - 10-2-2010 at 11:25

Yes i know that refluxing longer would be good for the yield.
This was just a crude quick and dirty test, it will be scaled up later.

[Edited on 10-2-2010 by User]

rrkss - 15-2-2010 at 20:51

Well I just reran my synthesis and upon the second distillation, I did add a thermometer. It came over at exactly 77 degrees Celsius.

entropy51 - 16-2-2010 at 07:43

Good Job!

bbartlog - 16-2-2010 at 09:32

Quote:

Can someone tell me why the acetic acid itself doesn't catalyse the reaction?

I'm no expert, but I believe that the problem is that acetic acid just isn't strong enough. In order for the reaction to take place, the ethanol needs to be protonated to form an oxonium ion. Since the conjugate acid of ethanol C2H5(H2O+) has a pKa of -2, you want an acid that has a pKa lower than that to protonate ethanol. Acetic acid (a weak acid) has a pKa of 4.8, where sulfuric acid has a pKa of -3.
I expect that HCl is also strong enough but since it's more volatile, possibly results in some volatile products via side reactions (ethyl chloride), and isn't as hydrophilic as sulfuric acid, it wouldn't be quite as suitable.

rrkss - 16-2-2010 at 10:01

The mechanism involves the carbonyl C=O on the acetic acid being protonated. In order to do that effectively, you need a strong acid like sulfuric acid. Ethanol can also act like an acid and the reaction will run just extremely slowly hence we add the sulfuric acid to speed things up greatly.

gardenvariety - 16-2-2010 at 21:22

Since you mentioned the FDA, I'll assume you're in the States. A good OTC supply of ethyl acetate is nail polish remover, at about 70ish% concentration. One distill gets you the acetate/ethanol/water azeotrope, perhaps you can dry it and break the azeotrope from there.

chemrox - 16-2-2010 at 22:00

@rrkss-"This is counterproductive as you loose product unnecessarily washing it with water. I only do a wash with bicarbonate because my reagent in excess was Acetic Acid."

I would anticipate a lot of foaming doing this. With a simple esterification reaction like this, involving alcohol and acid, I wouldn't wash at all. I'd run the distillation with a frax column as mentioned several times. Reflux for 30 mins should be plenty. Acetic just isn't a strong enough acid to catalyze the reax. Hence the SA. This could also be base catalyzed. I wonder how NaOH would work? Or a tiny bit of CaH? With NaOH you'd have Na-acetate in solution and also some Na-ethoxide in eq. with NaOH/Ethanol. I think they all would work. Why don't you try them all and report back with comparative yields? That would be a good beginning experiment.

rrkss - 17-2-2010 at 00:26

Quote: Originally posted by chemrox

@rrkss-"This is counterproductive as you loose product unnecessarily washing it with water. I only do a wash with bicarbonate because my reagent in excess was Acetic Acid."

I would anticipate a lot of foaming doing this. With a simple esterification reaction like this, involving alcohol and acid, I wouldn't wash at all. I'd run the distillation with a frax column as mentioned several times. Reflux for 30 mins should be plenty. Acetic just isn't a strong enough acid to catalyze the reax. Hence the SA. This could also be base catalyzed. I wonder how NaOH would work? Or a tiny bit of CaH? With NaOH you'd have Na-acetate in solution and also some Na-ethoxide in eq. with NaOH/Ethanol. I think they all would work. Why don't you try them all and report back with comparative yields? That would be a good beginning experiment.

The bicarbonate wash is because a little acetic acid comes over when you stop the fractional distillation at the temperature drop (though the second fraction is mostly water). Not much foaming at all. A second CaCl2 wash is also needed if you don't own type 4A molecular sieves to remove unreacted ethanol.

Base catalyzed reaction would work but I prefer acid since etched glass and frozen joints aren't my idea of a fun time.

smaerd - 15-1-2011 at 16:44

Well I finally got around to doing this. As many months have passed haha.

I did a simple distillation of nail polish remover. The distillate came over at about 71*C, so I am assuming there is an azeotrope with water? That or my thermometer is wrong(just kidding)

.

I prepped 10 grams of CaCl2 which is precipitating right now. I was assuming the azeotrope was with ethanol while it was distilling, which is why I whipped some up really quick.

Would a fractional distillation clean this azeotrope up and get it boiling clean at ~77*C? If not I'm assuming it will still suffice for the purposes I am using it for. Thanks for any advice.

bbartlog - 15-1-2011 at 17:16

Quote:

Would a fractional distillation clean this azeotrope up

No, you can't break an azeotrope with fractional distillation.
Ethyl acetate forms azeotropes with both water and ethanol.
I think rrkss' suggestion (CaCl2 to remove ethanol and water) sounds good.

smaerd - 15-1-2011 at 17:40

Excellent thanks bbartlog! Good thing I've got some ready

.

Seriously recommend the nail polish remover distillation over ordering GAA and esterification. (edit: thought I had a 50ml receiving rbf, it was actually 100ml hehe)It's around 60-70% concentration EA and is VERY affordable. The remaining goo left on the flask is simply cleaned with 4-5 mls of acetone.

[Edited on 16-1-2011 by smaerd]

The WiZard is In - 15-1-2011 at 18:25

Quote: Originally posted by gardenvariety

Since you mentioned the FDA, I'll assume you're in the States. A good OTC supply of ethyl acetate is nail polish remover, at about 70ish% concentration. One distill gets you the acetate/ethanol/water azeotrope, perhaps you can dry it and break the azeotrope from there.

Ethyl acetate is commonly used in insect killing jars (K or Na cyanide
works a lot better, though traditionally black cyanide was used.)

Try www.Bioquip.com.

NB- Requires the onerous Hazmat Shipping charge.

[Edited on 16-1-2011 by The WiZard is In]

smaerd - 15-1-2011 at 18:54

It says here to use K2CO3 or Na2SO4 for drying ethyl acetate
http://delloyd.50megs.com/moreinfo/drying.html

So I think I'll do a drying run with K2CO3 for removal of water, then a run with CaCl2 for ethanol/isopropyl(both alcohols were in the MSDS and ingredients).

[Edited on 16-1-2011 by smaerd]

rrkss - 15-1-2011 at 19:55

The easiest way to remove the ethanol is shake it with a saturated solution of CaCl2 and H2O. What I do is mix 20 grams of CaCl2 with 20 mL of water and put that in a sep funnel with the EtOAc and shake for a few minutes. Then let the layers seperate and drain the top layer over some anhydrous CaCl2 for drying. Distill the dried product and it should come over at 77 degrees. Done it many times.

smaerd - 15-1-2011 at 20:29

Thanks for the advice it really means a lot

. Man at home chemistry is so much fun!

rrkss - 16-1-2011 at 09:28

It is, I just removed grease from one of my ties using some EtOAc, saved on a dry cleaning bill :-).

smaerd - 16-1-2011 at 20:40

I'm having a devil of a time drying this stuff. I took your advice rrkss, I ended up losing maybe 30mls of the total solution so I assumed that was the alcohol component. Still distilling over at 70*C.

Here's what I did:
Using 150mL's of distillate from non-acetone primary ingredient EtOAc nail polish remover.

first I prepared CaCl2 from CaCO3 + HCl. Filtered away contaminants(insoluble CaCO3), weighed the water solution at 33mLs it weighed approx 55grams so I figured the experiment was done correctly(expected about a 20G yield). Evaporated CaCl2 soln down to approx 20mLs, and washed/seperated the solution in a sep funnel. Ignorantly tried distilling immediately after, Came over at still 70*C.

Bought some Drive-way deicer(90%-100% CaCl2). Crushed pellets with mortar and pestle, dried in an over for a half an hour at 300*F/~150*C. Approximately 50grams(my scale can be dodgy). Added the EtOAc directly to powdered CaCl2(hopefully anhydrous?) and mixed thoroughly. Some of powder appeared to be 'dry' after several minutes.

Filtered, then ran distillation. Still coming over at 70*C?

Is the problem not using anhydrous CaCl2? How can I prepare it from CaCl2 'Pellets'? Or do I need to keep doing washes?

Edit - Upon completing the distillation there was a CaCl2 ppt in the boiling flask. I am guessing the problem here isn't the alcohol it's the water? this website says that the azeotrope between EtOAc and water is 70.3*C. So this will be suitable for the purposes I need it for. Even though I'm OCD about purity.
http://www.solvent--recycling.com/azeotrope_1.html

[Edited on 17-1-2011 by smaerd]

peach - 17-1-2011 at 02:56

Interesting topic.

Shame you're not in the UK, I could post you some E.acetate and some dry CaCl2.

But half the fun is making it yourself and learning along the way!

There a thread about drying CaCl2 here

smaerd - 17-1-2011 at 10:55

I cooked crushed drive-way de-icer(CaCl2 90-100% conc.) in an evaporating dish directly over stove flame for 30 minutes(stirring every 5 minutes with a glass stirring rod). Quickly covered it with aluminum foil and allowed it to cool for 15 minutes. it lost 1.7grams of water. So it's pretty close to anhydrous.

I then dried 80mls of impure EtOAc with 28.3 grams of CaCl2. It distilled over at 70*C. It must be a water azeotrope There can't possibly be that much ethanol in it. I'll try a K2CO3 dry after this. If that fails I guess I'll have to deal with what I've got until I can afford to buy pure ethyl acetate. Thanks everyone.

[Edited on 17-1-2011 by smaerd]

[Edited on 17-1-2011 by smaerd]

Ethyl acetate - Home Chemist Popular Science

The WiZard is In - 17-1-2011 at 13:49

January 1946
http://tinyurl.com/4mrt4y9 Page 199 R.

---
Byda - drying acetone has been discussed here before.

http://www.sciencemadness.org/talk/viewthread.php?tid=4488

This from the news group Sci.chem

http://tinyurl.com/47qfdvw

djh
----
From the Outer Limits of Experimentalism...

The car was 3.15 meters long, 1.15 meters tall
and weighed 308kgs... Constructed out of motorcycle
parts and with a body made of pig's blood,
chicken feathers and shellac, the Feszival
was smelly, but it worked.

The Marvellous Magyar Micocars
How Hungry circumvented Stalin and had a bit of fun
The Economist 18xii10

starman - 17-1-2011 at 14:01

Just a thought smaerd,are you sure your thermometer is sitting far enough down in the adapter?

smaerd - 17-1-2011 at 16:03

Speaking of thermometers... Mine just broke! The stupid o-ring that was holding it somehow expanded. I hear a thud, snap, and it fell right into the boiling flask... On the bright side now I have some mercury? Gotta order a new thermometer, guess I should invest in a thermometer clamp as well.

[Edited on 18-1-2011 by smaerd]

peach - 17-1-2011 at 16:20

Mine has done something similar.

At one point, I started undoing it before removing the adaptor and it fell into a 600mm vigreux column, snapping one of the pins off.

I had that thermometer for many years and many experiments after, but it developed a split in the column; a big one. I tried freezing it and vibrating it back into a solid column then, on closer inspection, found a hairline crack in the bulb. So that was the end of it's life and, like you have there, I have a little blob of mercury to remember it by.

I found an old, plain test tube and siliconed it in there to amuse people with - as most people born in the last few decades haven't ever seen it in person, and it is a very odd thing to look at and feel sliding around in the tube like liquid lead. People always want to play with it when I put it in front of them.

Point being, you're not the first person to manage that (I know at least one other guy on here, besides myself, has done it recently).

Some lessons you only learn through experience!

[Edited on 18-1-2011 by peach]

UnintentionalChaos - 17-1-2011 at 16:23

Quote: Originally posted by peach

At one point, I started undoing it before removing the adaptor and it fell into a 600m vigreux column, snapping one of the pins off.

I knew you worked on a fairly large scale, but damn!

peach - 17-1-2011 at 16:29

Quote: Originally posted by UnintentionalChaos

Quote: Originally posted by peach

At one point, I started undoing it before removing the adaptor and it fell into a 600m vigreux column, snapping one of the pins off.

I knew you worked on a fairly large scale, but damn!

I've really gone to town on the out of place units today.

rrkss - 17-1-2011 at 16:44

if the azeotrope is water, you should see two layers form when you distill the ethyl acetate. My guess is maybe its azeotroping with the isopropylnol since the CaCl2 should have removed the Ethanol and the water if it was anhydrous. You do decant the EtOAc from the CaCl2 before distillation do you?

smaerd - 17-1-2011 at 17:01

@peach : Awe man if it took out my vigreux I'd be very upset(esp a 600mm one). Sounds like I got away from this pretty clean. RIP to our thermometers hehe. Served us well. Your right this mercury is pretty neat

.

Besides this give me an excuse to have a thermometer clamp.

WAIT? Is that your picture or did you digitally modify mine? haha edit - oh I get it you took a picture of your Hg sample overtop of your screen haha.

@rrkss: Yes I was decanting prior to distillation and doing a quick filtration. There were no obvious layers in any of the distillates. When I added CaCl2 though and shook the whole solution turned a murky calcium white/gray. Which isn't really typical of other solvents I've dried. Normally the drying agent wouldn't linger in soln for more than a few moments. Perhaps a finer filtration will help, I'll try a vac filtration with proper paper instead of gravity filtration and coffee filters

[Edited on 18-1-2011 by smaerd]

UnintentionalChaos - 17-1-2011 at 17:53

I see your mercury and raise you more mercury.

Bring IT!

smuv - 17-1-2011 at 22:58

This thing is gonna go viral.

peach - 18-1-2011 at 03:30

smaerd - 18-1-2011 at 08:18

Hahahaha I love this forum

497 - 10-6-2011 at 05:23

Well, I don't want to turn this into a dick sizing competition... but I got you all beat! Fortunately it did not come out of thermometers, though I've broken more than my fair share of them. Heheh.. I suppose its only a matter of time before some lucky bastard blocks half the picture with their 76 pound flask full of it...

On a more relevant note, according to google saturating impure EtOAc with CaCl2 (I'd leave excess in the still pot) and distilling it directly should break the azeotropes with water and alcohols. I suspect you may get better results that way.. With a bit of alcohol contamination, you could have way more water in your EtOAc than you bargained for and still no phase separation. Trying to get that out by letting it sit on CaCl2 then filtering may be ineffective, or at least inefficient. Of course you'll still have to dry it more thoroughly after distilling from the CaCl2 solution, but at least there should only be a small amount of H2O/EtOH to deal with.

I wonder what other additives could be used besides CaCl2? There's a lot of options.. Maybe a nonionic hygroscopic compound like glycerol or glycol could work well? With a liquid hygroscopic agent there would be no limitation on the concentration and you could afford to use a lot. At least they're very cheap, OTC and reusable. Oh, or use both CaCl2 and glycol/glycerol!

I'm going to attempt to distill some nail polish remover soon so I'll try to post my results.

Does anybody know where to get the damn current MSDSs for "Cutex" brand non-acetone nail polish remover? I searched high and low, and never found anything but the acetone based one and some really old ones that don't correspond to the ingredients listed on the bottle.. I couldn't find an MSDS for the generic Kroger brand version either (which is methyl acetate based according to the bottle.) It's strange because normally I've found MSDSs for common consumer products are very easy to get. I suppose I'll find out the concentrations of the important stuff soon enough..

Phosphor-ing - 10-6-2011 at 05:45

I had to get MSDS on everything at our office. The products that were generic store brands I had to call the number on the bottle to get them to fax the MSDS. Publix in particular doesn't have them online. They will gladly send them to you if you tell them the sku # (the number below the bar code).

rrkss - 12-6-2011 at 14:41

I've always shaken my impure EtOAc with a saturated CaCl2 solution and distilled after seperation giving me a good clean product pretty much free from EtOH. I 1 mL of H2O for every gram of CaCl2 I use and it has always worked well for me.

497 - 16-6-2011 at 00:12

I got it backwards in my last post, the Cutex stuff has methyl acetate and the kroger product is ethyl acetate. The kroger stuff also has a bunch of ethanol in it so it makes it a real pain in the ass to purify. Cutex gives a nice clean 95% AcOMe 5%H2O azeotrope which is easily dried with MgSO4 or CaCl2. Unfortunately Cutex is only 30-40% AcOMe.. Comes to about 30-40$/liter of AcOMe. Not too bad I guess.. Also if you wanted it you get a good 250-350ml of monobutyl diethylene glycol from it, but the purification of that would probably be tougher. I wonder how suspicious people would get seeing someone buying 10 or 20 bottles of nail polish remover?

Does anyone know of a good ethyl acetate source besides nail polish remover?

sulfuric acid is the king - 15-9-2020 at 05:34

Can Ethyl Acetate be used for nitroparaffin extraction?

njl - 15-9-2020 at 06:05

Wow, what a revival. Uhh, extraction from what?

sulfuric acid is the king - 15-9-2020 at 06:42

Mostly water, traces of nitric/nitrous acid...
Will ethyl acetate form some azeotrope with nitroalkanes, or will it be just efficient like diethyl ether.
I try to avoid ether...

njl - 15-9-2020 at 08:32

ethyl acetate has an azeotrope with water. My first recommendation is to start by distilling your nitroalkanes out of what I'm assuming was the nitration mixture, then you can dry the distilled product with either a desiccant, brine/salt wash, or further distillation.

sulfuric acid is the king - 15-9-2020 at 12:09

Yea but for micro scale and with nitroalkanes that have boiling point near that of water that's practically impossible.
I need it for analysis, first extraction, than evaporation, hexane is very bad, it forms azeotrope.
Diethylether, i would need to make it, but it is hard in relatively hot climate..
Ethyl Acetate is only solution (yea i don't have access to DCM)...
I think benzene would also work, but it's carcinogenic...