khourygeo77 - 27-3-2018 at 07:40
Hello,
I'd like to make ethyl sulfate
However, I'd want to know how it can be prepared exactly. I know sulfuric acid should be mixed with ethanol
Also, I want to know the precautions I should take, and if this experiment will be of any danger?
Thank you for your responses
Magpie - 27-3-2018 at 08:11
Here's my attempt at diethyl sulfate. Read the whole thread.
https://www.sciencemadness.org/whisper/viewthread.php?tid=78...
khourygeo77 - 27-3-2018 at 15:41
Thank you. Ethyl sulfate is supposedly not too dangerous right? Not more dangerous than solvents such as HCL or methanol.
JJay - 27-3-2018 at 17:03
Diethyl sulfate is believed to be a potent human carcinogen, although that's never been proven. So far, few volunteers have stepped forward for human
trials.
Monoethyl sulfate (i.e. ethyl sulfuric acid) is not thought to be a carcinogen or much more toxic than something like acetic acid. Both ethyl sulfuric
acid and diethyl sulfate are sometimes referred to as ethyl sulfate, so it really depends on which one you are talking about.
Magpie - 28-9-2018 at 14:41
My 18" TC arrived so I ran this synthesis again. The equipment set-up was perfect and I ran it exactly per the procedure by Lynn and Shoemaker [Kodak
company, 1924]. The set-up can be seen in the attached pictures.
This run gave absolutely no diethyl sulfate. The 29mL of product showed no interface and failed the drop test with water. It did not smell of
peppermint but the lab smelled of ether. I now believe that the salt temperature of 155°-165°C called for in the procedure is too high. In my
previous attempt the early period of the run had a salt temperature that was too low. There I got a yield of 11.4g.
[Edited on 28-9-2018 by Magpie]
AJKOER - 29-9-2018 at 15:51
Wikipedia comment on preparation (see https://en.wikipedia.org/wiki/Diethyl_sulfate):
"It can be prepared by absorbing ethylene into concentrated sulfuric acid or by fuming sulfuric acid into diethyl ether or ethanol.[3]"
Looking at Wiki structure of the diethyl sulfate, it is basically:
(C2H4)-H-(SO4)-H-(C2H4)
which as the 1st preparation suggests, appending ethylene to each side of concentrated sulfuric acid (and does not employ fuming sulfuric acid
implying SO3 presence for the removal of H2O from C2H5OH, a more involved path).
I would suggest trying the ethylene acting on concentrated sulfuric acid path.
Note: In the presence of any hot water, diethyl sulfate rapidly decomposes into monoethyl sulfate and alcohol (see https://pubchem.ncbi.nlm.nih.gov/compound/Diethyl_sulfate#se...).
[Edited on 30-9-2018 by AJKOER]