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VSEPR_VOID
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Some C60 Chemistry
As part of a project for school I am making aromatic amine C60 fullerene adducts. Here is some pictures of them.
Does anyone else have an interest in C60 chemistry? C60 has recently dropped in price, is very easy to make with a vacuum chamber and arc welder, has
colorful derivatives, and is a new frontier.
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Ubya
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i was planning in making some C60 as i have a vacuum chamber (and i will build the arc welder). it's interesting the fact that is a carbon allotrope
solubile in toluene and many other solvents
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fusso
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Remember to see if it can react with piranha soln!
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VSEPR_VOID
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Quote: Originally posted by Ubya  | | i was planning in making some C60 as i have a vacuum chamber (and i will build the arc welder). it's interesting the fact that is a carbon allotrope
solubile in toluene and many other solvents |
You cand find many papers on it that go into detail. All it requires in graphite rods, vacuum, and some He to use an an inert gas.
Further more, if you have a soxhlet extraction and purification is easy using chloroform or toluene
Imagine if we had a C60 sticky! If we had a member making C60 (you can make easily a gram a day) then we could all start C60 related projects.
[Edited on 16-11-2018 by VSEPR_VOID]
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12thealchemist
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I have several kilograms of soot which I plan to extract at some point in the distant future with a Soxhlet extractor with several solvents, gradually
decreasing in polarity, to extract the various soluble components, including fullerenes. I'm aware that these are likely present at less than 1%, but
1 kg @ 0.1% = 1 g, which is extremely valuable.
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VSEPR_VOID
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| Quote: Originally posted by 12thealchemist | | I have several kilograms of soot which I plan to extract at some point in the distant future with a Soxhlet extractor with several solvents, gradually
decreasing in polarity, to extract the various soluble components, including fullerenes. I'm aware that these are likely present at less than 1%, but
1 kg @ 0.1% = 1 g, which is extremely valuable. |
How was the soot generated? If it was generated by regular fullerene methods than it should be more than 10% C60. If it was made by burning wood in
air, or something similar, than the C60 should be in very small trace amounts (a lot less than 1%). In addition, you would have to consider the
organic residues that saturate the wood.
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12thealchemist
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Unfortunately, I don't know the origin of the soot. It was sold originally for gardening purposes, so it could be coal and/or wood soot. Either way,
even if it doesn't have fullerenes, it will probably contain something interesting.
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Mr. Rogers
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Does anyone know what the deal is with C60 Olive Oil? What is this about?
https://www.amazon.com/s/ref=nb_sb_noss?url=search-alias%3Da...
[Edited on 16-11-2018 by Mr. Rogers]
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VSEPR_VOID
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There was a paper a long time ago that provided evidence that C60 had some medicinal value scavenging radicals; health nuts jumped on it for its
mystical powers.
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Ubya
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| Quote: Originally posted by VSEPR_VOID | if you have a soxhlet extraction and purification is easy using chloroform or toluene
[Edited on 16-11-2018 by VSEPR_VOID] |
i did not think of using a soxhler extractor, but this is a good idea, one more reason to buy it
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VSEPR_VOID
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Yeah, you can even pack the soxhlet with activated carbon or alumina and purify the extract via chromatography. There are lots of papers out there. I
really want to make a C60 reactor one day.
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VSEPR_VOID
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This should be C60(C6H5CH2CH2CH2NH2)12
Just got done purifying it with IPA washings
It forms deep red solutions in hot IPA, chloroform, and phenylpropylamine.
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Tsjerk
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How did you prepare it?
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VSEPR_VOID
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I hopefully will have the paper out within the year. I am working with a real research lab. It was prepared using a very simple one-pot reaction
between the corresponding aromatic and C60 with a aluminium halide catalyst.
Purification has been the hardest part. Soon I will be using mass spectroscopy to confirm my product.
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Texium
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Well this thread isn't exactly "C60 Chemistry" then, is it? It's more like, "a couple pictures of a purported C60 derived compound that hasn't been
verified and some vague allusions to how it was made."
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fusso
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Did you mean: "C6H4"?
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Tsjerk
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| Quote: Originally posted by VSEPR_VOID | I hopefully will have the paper out within the year. I am working with a real research lab. It was prepared using a very simple one-pot reaction
between the corresponding aromatic and C60 with a aluminium halide catalyst.
Purification has been the hardest part. Soon I will be using mass spectroscopy to confirm my product. |
It won't hurt anyone explaining what you did.
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VSEPR_VOID
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| Quote: Originally posted by Tsjerk | | Quote: Originally posted by VSEPR_VOID | I hopefully will have the paper out within the year. I am working with a real research lab. It was prepared using a very simple one-pot reaction
between the corresponding aromatic and C60 with a aluminium halide catalyst.
Purification has been the hardest part. Soon I will be using mass spectroscopy to confirm my product. |
It won't hurt anyone explaining what you did. |
Okay, sorry for the confusion
10 mL of an aromatic amine (aniline or phenylpropylamine for example) was placed into a glass tube with 50 mg of anhydrous aluminium chloride and 50
mg of C60.
The tube was sealed then agitated for 2 hours to mix the reaction components well. The tube was left to react for 3 days.
After 3 days the color was a very dark red.
Washing with water, to remove the catalyst, and work up and evaporation with chloroform left a thick residue containing the amine and C60 adduct.
This was then purified via recrystlization with hot 99.5% ISPA (3 mL for ever 0.5 g of residue). Upon cooling the ISPA with ice, the precipitate was
collected then washed with fresh ice cold ISPA.
Attached is a paper on purifying C60 soot with a soxhlet extractor.
Attachment: A simple Soxhlet chromatographic method for the isolation of pure fullerenes C60 and C70.pdf (998kB)
This file has been downloaded 434 times
No, here is the molecule https://www.sigmaaldrich.com/catalog/product/aldrich/p32406?...
[Edited on 18-11-2018 by VSEPR_VOID]
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DrP
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| Quote: Originally posted by VSEPR_VOID | I hopefully will have the paper out within the year. I am working with a real research lab. It was prepared using a very simple one-pot reaction
between the corresponding aromatic and C60 with a aluminium halide catalyst.
Purification has been the hardest part. Soon I will be using mass spectroscopy to confirm my product. |
Let us know how that goes. :-) The mass spec and the paper. :-) Good luck. :-)
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VSEPR_VOID
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I will. It will find its way into the prepublications.
I also want to try out the same reaction but with aromatic alcohols and carboxylic acid in place of the amines.
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DrP
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I am afraid I do very little chemistry like this - C60 has always fascinated me though since I first heard about it in the 1980s and then learnt
about some of it's chemistry at uni in the 90s. I expect we know so much more about it now than we did then.
If I remember rightly (which I probably don't) - does it react with other atoms as if it was an atom with valence II? I seem to remember that it can
accept or donate 2 electrons... something like that - this was over 20 years ago so I am probably not remembering it correctly or we have moved on
from then and learnt more. Please excuse my total lack of knowledge about it - I just find the structure interesting as a new allotrope of carbon.
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VSEPR_VOID
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C60 behaves as a super electron deficient polyalkene. It undergoes a variety of reactions to form many adducts. For example, C60 is very reactive with
grignard reagents.
Most reactions with C60 are driven forward because of strain relief from the double bonds becoming single bonds. This however, can be counter acted by
the eclipsing of the added groups causing more steric strain. An example of this is polyhydrogenated C60. C60H60 is not stable and does not form, but
C60H36 is the most stable hydrogenated derivative. It has just enough 1,2 additions (which reduce the strain caused by double bonds) to counteract the
strain from eclipsed hydrogens.
C60, in addition to having a very reactive exterior, has endohedral chemistry as well. Because of steric hindrance, the inside of C60 acts as a sort
of chemical Feriday cage. As a result, exotic or reactive species (such as nitrogen radicals) can be trapped inside and studied.
Right now a lot of research is being conducted on opening holes in the C60 cage, inserting an element or molecule inside, then closing that hole.
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fusso
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Yes I know I mean the R-C6H5 should lose 1 H when it react with C60 in
a friedel craft to form C60-C6H4-R isnt it?
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walruslover69
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How do you control the number of adducts that attach to the C60?
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Tsjerk
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What is the solubility of C60 in the solvent anyone would typically use for a soxhlet?
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