Chromatography Forum

I need a procedure that I can follow, so I can separate ethyl acetate from nail polish remover. Yes, I have read about GC but unfortunately, my school does not have a GC instrument. Also, is there a special indicator for ethyl acetate, and how would i be able to tell the amount in the solution ( nail polish remover). Ive looked this up hundreds of times, and nothings helped.
Some help would be GREATLY APPRECIATED

Unless you have some instrumentation available, you would have to separate the ethyl acetate from everything else in the mix. If there are multiple volatile componetns, you may have to do a fractional distillation and perhaps some additional chemical steps. Do you have any instrumentation avaialble to you?

There is no simple indicator for ethyl acetate.

Do you know the other ingreedients in the nail polish remover?

The thing is , I only have simple instrumentation available, so I was thinking of possibly finding the boiling point of the other ingredients in the nail polish remover, then gradually increasing the temperature until the ethyl acetate is left , which I am assuming has the highest boiling point ( Im about to research the boiling points right now.)

The other ingredients in the nail polish remover are :
Isopropyl Alcohol, Dibutyl Adipate, Caprylic Capric Triglyceride , Benzophenone- 3 ; Cl 26100 ( D& C #17)

If certain ingredients have higher boiling points than ethyl acetate, what chemical steps would you recommend doing to separate the final ingredients?

Thank you

Following your list of ingredients, the challenge here is to separate ethylacetate and 2-propanol. A simple destillation setup vith a vigreux column might do the job. Even better is to instll an Antlinger column head on top of the vigreux column and regulate the ratio between the reflux and the destillate. A constant temperature at the columnhead of 77°C should indicate the presence of pure ethylacetate.

The bad news is that isopropanol and ethyl acetate form an azeotrope. It is 77% ethyl acetate and boils slightlly higher than ethyl acetate by itself. Thus, a distillation would give ethyl acetate until the ethyl acetate was sufficently depteted that the azeotrope would come over in the still. Unless, of course, the isopropanol would be in excess, in which case the azeotrope would distill followed by isopropanol.

While the other compunds present boil at higher temperatues than isoporopanol, there may be a significant portion of these in the mix. If there is a clean break in the distillation after the azeotrope or isopropanol, you may be able to determine the composition of the distilled portion with a hydrometer and the total mass of the combined isopropanol and ethyl acetate by weight. I would not bother with the vigreux column. I would just do a simple distillation until the temperature rose to the boiling point of isopropanol - at which point the distillation is immediately stopped.

We would have to keep an eye out for azeotopes with the the higher boilers, but my immediate expectiation is that there should not be much.

In your initial post you aske for a chromatograpy method. If you do not have a GC, it would have to be an LC system. Whlie there are other forms of chromatography, you need to be able to detect the compund of interest - and without instrumentation, detecting the ethyl acetate in a way that you could quantitate it would be tough - at best. An HPLC system would have a detector that could be used for quantitation. If you were to use an open chromatographic column, you would have to wash the nail polish remover through in some liquid - an the ethyl acetate would have to be measured in that liquid. Evaporation of solvent woul most likely result in loss of the ethyl acetate, so again that takes us back to instrumentation.

With no GC, I figure it would be less likely to have an NMR handy... That would be so easy.

It's a pity about the minor ingredients. In a high-school lab with nothing more sophisticated than a thermometer and a balance, I'd be tempted, with simple solvent mixtures, to see if I could determine the mix by boiling point, density, or a combination of the two, using comparison to known mixtures.

We did some qualitative organic analysis in high school. There exist books on this.

I was thinking about a hydrometer, assuming that the high boilers would be present at low concentration. But looking on line, I discovered that some of the esters are included between 1 and 5%. And that could be enough to affect specific gravity.

I do wonder where this project came from. But then again, I can think of some that came along in the work place that rather exceded the labs apparent equipment capability - so we had to become creative.

just an idea:
are there any ester specific derivatization reagents out there, to form a product that then could be assessed with a (UV)-VIS-photometer?

or do a serie of steps and a combination of differnt group specific reactions

or maybe something in this way:
- separate the lower boiling compounds such as EtAc and Isospropanol from the rest by "distillation". Never mind of the purity as long as there are no other esters present.
Use a defined volume of nail polish remover (used later for calculation) -> Goal: less complex mixture, at its best, only of EtAc and a sec. alcohol.

- do a basic hydrolysis of the ester at high pH (eg. with NaOH). Use a volumetric amount of NaOH.

- titrate the excess of NaOH with an acid like HCl or similar

- calculate the (molar) amount of acetic acid formed during the hydrolysis = molar amount of EtAc

- calculate the volume (or mass) of EtAc after distillation and calculate the ration of EtAc in your initial sample volume
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or use the mixture after the distillation for the reaction with some derivatization reagents for esters (if there are some).

Or if you have an infrared spectrometer, maybe you could use the C=0 signal (or some other) for quantitative assessment.

But GC (or NMR) would still be the techniques of choice for such a problem

PS:
or do the hydrolysis on the whole mixture (or after pre-distillation to get rid of the glycerine-ester) and try to measure the produced acetat-ion by ion-chromatography or trap and release the anions formed on an ion-exchange resing and do some potentiometric titration.
Don't know about the pKa of adipic acid, but even if one is close to acetate, adipic acid is a binary acid and should give two titration steps, so it should still be possible to calculate the acetate present.

Could you do this by TLC? Once you have a separation you can spot standards of different concs to find the LOD (fixed loading TLC). It's a fiddle but you only need a UV lamp and a jam jar.

Could you do this by TLC?

That would be a good choice for non-volatiles, but wouldn't work for ethyl acetate.

I'd suggest that the "bottom line" on this is that it really is not a suitable student project for a lab without instrumentation.