Bmoore55
Hazard to Self
Posts: 85
Registered: 23-7-2018
Location: Texas
Member Is Offline
|
|
Newe YouTube Video: Methyl Iodide Synthesis with Aluminum Foil
I just uploaded a new video about my synthesis and analysis of Methyl Iodide using aluminum foil. Please have a watch and let me know what you think.
Cheers!
https://www.youtube.com/watch?v=zyd9GkxXDAk
|
|
|
CouchHatter
Hazard to Others
Posts: 146
Registered: 28-10-2017
Location: yes
Member Is Offline
|
|
Cool that you're putting yourself out there! If everything went according to plan it wouldn't be as entertaining. I liked the second half of the video
especially, equipment and processes I've only read about. Neat that you explain what youre doing to the samples and how it does or doesn't give you
data.
Typo in the video description. Still miles ahead of me, actually producing content! I'll look out for part 2.
|
|
|
j_sum1
Administrator
Posts: 6218
Registered: 4-10-2014
Location: Unmoved
Member Is Offline
Mood: Organised
|
|
I love the time you put into analysis. You are really fortunate to have that gear.
From my point of view, this is always a frustrating topic to teach my secodary students because it is required information but schools simply do not
have access to this gear in general. And the focus is always on the complexities under the hood rather than the magic of putting a sample in and
getting a result out that you then have to interpret.
Your presentation is short, functional and practical and keeps the whole thing alive. I will share this video with my students when the topic comes
up. And then the complexities address students' genuine response of, "That's amazing. How does it work?"
|
|
|
monolithic
Hazard to Others
Posts: 435
Registered: 5-3-2018
Member Is Offline
Mood: No Mood
|
|
Nice video. If you have the time, I'm sure many of us would also appreciate a video on just your desktop NMR. 
|
|
|
draculic acid69
International Hazard
Posts: 1371
Registered: 2-8-2018
Member Is Offline
|
|
10/10. Another great video.as good as any chemplayer video.
|
|
|
Bmoore55
Hazard to Self
Posts: 85
Registered: 23-7-2018
Location: Texas
Member Is Offline
|
|
Thanks for all the feedback. I plan on doing some videos about each piece of equipment in the future, especially the NMR.
|
|
|
G-Coupled
Hazard to Others
Posts: 287
Registered: 9-3-2017
Member Is Offline
Mood: Slightly triturated
|
|
Oh - very cool.
Please make some videos showing off your kit - especially your NMR - that'd be awesome. 
|
|
|
XeonTheMGPony
International Hazard
Posts: 1636
Registered: 5-1-2016
Member Is Offline
Mood: No Mood
|
|
Erf My sympathies on the volcano (Any one ells scream at the monitor: COOL IT!!! ?
Or slowly add the alu!
And yes very lucky to have such a nice array of testing, I dream of an FTIR if the dogs can kindly stop hurting them self's, or vehicles stop breaking
down! Or the Sheep testing the wires for voltage!
|
|
|
Bmoore55
Hazard to Self
Posts: 85
Registered: 23-7-2018
Location: Texas
Member Is Offline
|
|
Quote: Originally posted by XeonTheMGPony  | Erf My sympathies on the volcano (Any one ells scream at the monitor: COOL IT!!! ?
Or slowly add the alu!
And yes very lucky to have such a nice array of testing, I dream of an FTIR if the dogs can kindly stop hurting them self's, or vehicles stop breaking
down! Or the Sheep testing the wires for voltage! |
Hahaha I was screaming at myself after I made the volcano. Such a rookie mistake, but that’s what happens when you get excited and in a hurry!
Thankfully my ego was the only thing that was truly hurt. I am very fortunate to have the equipment that I do. I have been very blessed with providing
my analysis as a service, but I figured I should use it to show people the analytical side of chemistry. It’s not like anyone can stop my, these
machines are mine! Mwahahaha!
|
|
|
reactofurnace
Hazard to Self
Posts: 76
Registered: 17-7-2015
Member Is Offline
Mood: Volatile
|
|
Loved the video!! Very nice equipment you have access to!
|
|
|
Mateo_swe
National Hazard
Posts: 501
Registered: 24-8-2019
Location: Within EU
Member Is Offline
|
|
Nice video.
I like the analysis part and some accidents just reflects reality.
What would be the most valuable (not in money) analysis gear a hobbyist could get and use for an affordable amount of cash? (not including thin Layer
Chromatography).
A used GC?
|
|
|
chemplayer...
Hazard to Others
Posts: 191
Registered: 25-4-2016
Location: Away from the secret island
Member Is Offline
Mood: No Mood
|
|
You do it just as well! Thanks for sharing the video and really enjoyed seeing someone trying this, as well as seeing some very very very very nice
equipment and I'm quite jealous!
|
|
|
Texium
Administrator
Posts: 4508
Registered: 11-1-2014
Location: Salt Lake City
Member Is Offline
Mood: PhD candidate!
|
|
Truly fantastic! Looks like you're living the dream with the perfect convergence of work and hobby.
While the analysis part was very well explained, I have one nitpick regarding the first part of the video. You refer to the aluminum as a catalyst,
which is incorrect. Since the aluminum is used in a stoichiometric amount and is consumed in the reaction, it is a reagent, not a catalyst. If it was
a catalyst, you wouldn't need to use a stoichiometric amount, and it would theoretically still be present as aluminum metal after the reaction is
over. It would also be nice to see some more discussion of the chemistry that is happening here, but I realize that this reaction is still not very
well-understood.
The following is somewhat speculative since I don't have definitive data to back me up, but what is most likely happening in this reaction is
analogous to the reaction that uses red phosphorus. The aluminum and iodine are reacting to produce aluminum iodide in situ, which reacts with the
methanol to produce methyl iodide and hypothetically aluminum hydroxide. The reason this reaction is more cumbersome and low-yielding than
the version using red phosphorus is that the byproducts in the phosphorus reaction remain soluble, while the aluminum compounds formed will clump up
and limit the reaction of the iodide/hydroxide intermediate. PI3 will readily give up all three of its iodines to leave behind
H3PO3. AlI3 gives up its first iodine to form AlI2OH, which is undoubtedly going to crash out of solution.
If you're lucky, a second iodine will react, but now that the mixture is heterogeneous, it's going to be a lot slower.
The elemental analysis that you showed for the solid byproduct supports this. If you take the percent mass compositions and divide by molar mass of
each element, you can get a crude molar ratio of the elements present. The oxygen to iodine molar ratio is roughly 2:1, so you probably have something
like Al(OH)2I as your main byproduct. While the ratio of aluminum to oxygen is just about 1:1, this can probably be chalked up to there
being excess aluminum metal present (which you can clearly see in the video, so not surprising). Exactly what compound(s) is/are formed here is likely
more complicated. Aluminum iodide itself exists as a dimer and there are numerous configurations of aluminum oxide-hydroxides, plus you still had bits
of aluminum metal in there too, so it isn't surprising that the XRD was unhelpful.
Edit: I should also note that I did a Sci-Finder search for anything on basic aluminum iodide, but it only turned up a few patents related to
anti-perspirant production that were very useless.
[Edited on 5-24-2020 by Texium (zts16)]
|
|
|
Bmoore55
Hazard to Self
Posts: 85
Registered: 23-7-2018
Location: Texas
Member Is Offline
|
|
| Quote: Originally posted by Mateo_swe | Nice video.
I like the analysis part and some accidents just reflects reality.
What would be the most valuable (not in money) analysis gear a hobbyist could get and use for an affordable amount of cash? (not including thin Layer
Chromatography).
A used GC? |
Honestly any kind of chromatography can be quite a cumbersome thing to keep up with. It is simply a personal thing for me, but I prefer FTIR to start
if possible. It has some of the widest application and compared to a GC there is a fraction of the maintenance cost. GC is really only a requirement
if you are dealing with identifying one compound in a complex mixture or if you are dealing with gases.
|
|
|
Bmoore55
Hazard to Self
Posts: 85
Registered: 23-7-2018
Location: Texas
Member Is Offline
|
|
| Quote: Originally posted by chemplayer... | | You do it just as well! Thanks for sharing the video and really enjoyed seeing someone trying this, as well as seeing some very very very very nice
equipment and I'm quite jealous! |
A review from the mighty Chemplayer! This is truly an honor! I have been a big fan of yours for quite a while, I even made a bitchute account to keep
up with your latest work. Can't wait for your next video, thanks again!
|
|
|
Bmoore55
Hazard to Self
Posts: 85
Registered: 23-7-2018
Location: Texas
Member Is Offline
|
|
| Quote: Originally posted by Texium (zts16) | Truly fantastic! Looks like you're living the dream with the perfect convergence of work and hobby.
While the analysis part was very well explained, I have one nitpick regarding the first part of the video. You refer to the aluminum as a catalyst,
which is incorrect. Since the aluminum is used in a stoichiometric amount and is consumed in the reaction, it is a reagent, not a catalyst. If it was
a catalyst, you wouldn't need to use a stoichiometric amount, and it would theoretically still be present as aluminum metal after the reaction is
over. It would also be nice to see some more discussion of the chemistry that is happening here, but I realize that this reaction is still not very
well-understood.
The following is somewhat speculative since I don't have definitive data to back me up, but what is most likely happening in this reaction is
analogous to the reaction that uses red phosphorus. The aluminum and iodine are reacting to produce aluminum iodide in situ, which reacts with the
methanol to produce methyl iodide and hypothetically aluminum hydroxide. The reason this reaction is more cumbersome and low-yielding than
the version using red phosphorus is that the byproducts in the phosphorus reaction remain soluble, while the aluminum compounds formed will clump up
and limit the reaction of the iodide/hydroxide intermediate. PI3 will readily give up all three of its iodines to leave behind
H3PO3. AlI3 gives up its first iodine to form AlI2OH, which is undoubtedly going to crash out of solution.
If you're lucky, a second iodine will react, but now that the mixture is heterogeneous, it's going to be a lot slower.
The elemental analysis that you showed for the solid byproduct supports this. If you take the percent mass compositions and divide by molar mass of
each element, you can get a crude molar ratio of the elements present. The oxygen to iodine molar ratio is roughly 2:1, so you probably have something
like Al(OH)2I as your main byproduct. While the ratio of aluminum to oxygen is just about 1:1, this can probably be chalked up to there
being excess aluminum metal present (which you can clearly see in the video, so not surprising). Exactly what compound(s) is/are formed here is likely
more complicated. Aluminum iodide itself exists as a dimer and there are numerous configurations of aluminum oxide-hydroxides, plus you still had bits
of aluminum metal in there too, so it isn't surprising that the XRD was unhelpful.
Edit: I should also note that I did a Sci-Finder search for anything on basic aluminum iodide, but it only turned up a few patents related to
anti-perspirant production that were very useless.
[Edited on 5-24-2020 by Texium (zts16)] |
I 100% agree about saying "Aluminum Catalyst" being incorrect. I guess it's obvious I don't write a script? I am still working with the residue left
after distillation to try and figure out what it actually contains. I think my original elemental analysis could be off since there is some unreacted
aluminum remaining in the solid which could throw off my numbers. I have found out that the residue is soluble in distilled water and leaves behind
unreacted aluminum. I also found out that the material that dissolves is likely reactive. I cleaned my vacuum fritt with distilled water followed by
some acetone so it would dry and when I emptied the vacuum flask the acetone and whatever was still in the water must have reacted because it caused
the liquid to go from a deep red to an almost transparent yellow color. And when I tried pouring this into my waste container it caused my eyes to
burn even when I was wearing my proper PPE. I plan on showing some of this in my next video, I am just working on my analytical approach and other
benchtop experiments to try and flesh out what the solid could be. If I am making Aluminum Iodide in situ with the original experiment then there
should be some remaining since my original experiment had these components in excess. Either way it is something I am still working on. I may have to
go back and try the XRD again once I reproduce my experiment with more of a focus on the material in the distillate flask rather than the MeI.
|
|
|
Texium
Administrator
Posts: 4508
Registered: 11-1-2014
Location: Salt Lake City
Member Is Offline
Mood: PhD candidate!
|
|
Perhaps you could see if you can get the water soluble part of the solids to crystallize, and retry the XRD with that.
Keep in mind that if there is aluminum iodide present, adding water will convert it to the hydrate, which has an entirely different crystal structure.
Like aluminum chloride, the anhydrous compound is a covalently bound Al2I6 dimer while the hydrate is an ionic compound of the
Al(H2O)63+ cation and iodide anions. Once it hydrolyzes it can’t be converted back to the anhydrous form.
|
|
|
Bmoore55
Hazard to Self
Posts: 85
Registered: 23-7-2018
Location: Texas
Member Is Offline
|
|
| Quote: Originally posted by Texium (zts16) | Perhaps you could see if you can get the water soluble part of the solids to crystallize, and retry the XRD with that.
Keep in mind that if there is aluminum iodide present, adding water will convert it to the hydrate, which has an entirely different crystal structure.
Like aluminum chloride, the anhydrous compound is a covalently bound Al2I6 dimer while the hydrate is an ionic compound of the
Al(H2O)63+ cation and iodide anions. Once it hydrolyzes it can’t be converted back to the anhydrous form.
|
Hahaha we are thinking the same thing! I have already dried out the aqueous solution and I am just trying to get some other work out of the way so I
can run the dried solid. It does look fairly crystalline so I am hopeful it will work in the XRD this time. Fingers crossed that I see something.
|
|
|
Justin Blaise
Hazard to Self
Posts: 82
Registered: 5-10-2011
Location: Parts Unknown
Member Is Offline
Mood: No Mood
|
|
Very nice video. The analysis portion was great. How does one acquire such sophisticated analytical equipment?
|
|
|
Cou
National Hazard
Posts: 958
Registered: 16-5-2013
Member Is Offline
Mood: Mad Scientist
|
|
very ncie might try this x)
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
