Sciencemadness Discussion Board

What did I make from bromoethane that smells fruity/flourescent?

alking - 8-9-2017 at 15:52

I've been trying to make some nn-diisopropyl-n-ethylamine. I made some bromoethane and reacted it with isopropylamine to make n-ethyl-n-isopropylamine. This was stripped of solvent and unreacted EtBr, basified, vacuum distilled, then fractionated to collect the product. The fraction was collected in a wider range than the target product, maybe 3C before and ~20C after.

This sat in a flask for about a week and I noted some salt forming on the bottom, presumably whatever EtBr remained further alkylating the amine. I go to use it today to make the final product and so I basify and vacuum distill it. After doing so I noticed a very distinctly sweet, soap/perfume like smell. I have made ethylsulfate before and that is the closest thing I can think of, in fact it smelled near identical. Any idea what this may be?

Metacelsus - 8-9-2017 at 20:17

What do you mean by "smells fluorescent"?

Loptr - 9-9-2017 at 09:04

Maybe floralescent?

alking - 9-9-2017 at 09:54

Floralescent, yes! I knew flourescent meant to glow/emit light, but I didn't know what word conveyed what I was trying to say, I'm glad you guys figured it out. It smells like flowers/laundry detergent or something fragrant.

clearly_not_atara - 9-9-2017 at 11:11

Acetaldehyde?

alking - 9-9-2017 at 15:13

You're probably right, that seems pretty likely. I guess it reacted with whatever oxygen was in the head space of the bottle and that would be why it was so noticeable as well.

Melgar - 10-9-2017 at 20:07

Fruity smells tend to be associated with esters, and esters tend to form easily in organic mixtures. If it's not ethyl acetate, it could be isopropyl acetate.

alking - 11-9-2017 at 05:13

I don't know what isopropyl acetate smells like, but it definitely doesn't smell like ethyl acetate, there's no vinegary smell at all.

Melgar - 13-9-2017 at 03:02

Quote: Originally posted by alking  
I don't know what isopropyl acetate smells like, but it definitely doesn't smell like ethyl acetate, there's no vinegary smell at all.

Ethyl acetate doesn't smell like vinegar either. It smells like nail polish. Any vinegar smell would be an acetic acid impurity.