Detonationology
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Synthesis of Hexane from Cellulose/Glucose
I been looking to order some hexane to use as a solvent for some time now, when I began to question the possibility of synthesizing it from
cellulose/glucose. I found some good articles, such as a report on Iridium-Catalyzed Hydrosilylative Reduction of Glucose to Hexane(s) and another regarding Catalyst Pair Converts Cellulose Directly To Hexane, but I was curious if a strong reducing agent such as LiAlH4 would work? Does anybody know of
any other novel synthesis' of Hexane?
“There are no differences but differences of degree between different degrees of difference and no difference.” ― William James
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MrHomeScientist
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That would be pretty interesting to convert cellulose to something more useful so easily. That catalyst would be difficult to obtain I'm sure. Also
the second link mentions an intermediate reaction between glucose and the hydrogen atmosphere. But if the product floats on top of the water layer,
wouldn't that block access to the hydrogen?
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Amos
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Quote: Originally posted by MrHomeScientist  | | That would be pretty interesting to convert cellulose to something more useful so easily. That catalyst would be difficult to obtain I'm sure. Also
the second link mentions an intermediate reaction between glucose and the hydrogen atmosphere. But if the product floats on top of the water layer,
wouldn't that block access to the hydrogen? |
Stir/aerate?
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battoussai114
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I'm pretty sure this would be done in a slurry bubble column reactor so you have a nice interface between the liquid, gas and the catalyst. And in
such reactor the products floating is not a problem as the hydrogen enters the bottom of the column while the heterogeneous catalyst is suspended in
the liquid.
[Edited on 24-9-2015 by battoussai114]
Batoussai.
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aga
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Can somebody do an experiment please ?
Preferreably more than 1 somebody.
Edit:
At least define the experiment so some chem bitch whore like me can do it for you.
[Edited on 24-9-2015 by aga]
It frustrates me that there is so much Brain on this forum and so little Doing.
It's just amazingly Strange (to me).
You know how, want to, and do not Do.
[Edited on 24-9-2015 by aga]
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fusso
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I was thinking about oxidizing all OHs to C=O 1st, then reduce to alkane by Zn/H+, but will dichromate break C-C bonds?
[Edited on 23/05/18 by fusso]
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Dr.Bob
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I worked in biofuels for a short time. This (conversion of cellulose to anything useful) type of work is 1) industrial type chemistry, 2) not cost
effective, and 3) requires high temps and pressures that are not practical at home. I'm not trying to rain on anyone's parade, making biodiesel with
MeOH/NaOMe is a doable task at home, although currently very cost effective, but quite doable. So is making ethanol for fuel (with the permits to
avoid being arrested by the feds).
But most other processes require insanely impractical equipment. I have seen some of the chemistry, most loses money in a big way. Most of the
pilot plants built so far have closed due to poor yields, poisoned catalysts, and lost money. Maybe one day they will come up with better solutions,
or more likely we will learn to bio-engineer plants to produce more useful chemicals directly. That is the direction that I see happening.
If you want hydrocarbon solvents, I would find a good OTC source, like gasoline, white gas, kerosene, starter fluid, etc, and fractionate it. I work
in a real lab by day, and even we can't afford iridium catalysts for most reactions.
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Sulaiman
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A friend of mine recently (a few years ago) researched lignin degrading microbial enzymes,
I think that most of her work involved replication of procedures,
and there seems to be lots of literature,
but as there is not a new .com explosion I guess it isn't commercially viable yet.
And there are cellulases, so some kind of fermentation may be viable
[Edited on 23-5-2018 by Sulaiman]
CAUTION : Hobby Chemist, not Professional or even Amateur
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Melgar
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If you want hexane, I'd recommend distilling it from gasoline before I'd recommend whatever crazy route it looks like you're thinking of trying.
Really though, your best bet might be to go to a few hardware and auto parts stores, then look at the aerosol cans that they have for removing grease
or cleaning electronics or brakes or whatever. Hexane is common in those. Then release most of the can's pressure by spraying it while holding it
upside down. Then turn it right side up and it will trickle out instead of spray out, and it'll be easier to collect. If the pressure ends up going
to zero entirely, so no more is coming out, check and see if you can squeeze the can a little with your hand, indicating pressure is low. Cans can be
punctured to let out the remaining contents, but needless to say, this can potentially be very dangerous.
Attempting to use LiAlH4 to make hexane is... what's the best term to use? How about just "no". Just remove that thought from your head. No need to
say why, there are too many reasons.
Alternately, heptane is virtually identical in its solvating properties and the only major difference is a somewhat higher boiling point. And heptane
is what's left over when you distill the diethyl ether (very valuable solvent) out of starting fluid. Starting fluid is perhaps 70-80% n-heptane, and
I've started using it a lot more in recent years just due to the fact that it comes as a byproduct of obtaining ether.
The first step in the process of learning something is admitting that you don't know it already.
I'm givin' the spam shields max power at full warp, but they just dinna have the power! We're gonna have to evacuate to new forum software!
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zed
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Ummm. A few years back, the sharpies, were out, trying to sell pilot plants, to produce fuels based on Levulinic acid Esters. Made from cellulose.
But, a quick survey, showed that such esters, were currently either very expensive or unavailable.
If it's so great, why isn't anyone selling the stuff?
It just wasn't a financially viable approach.
Excepting the part, where you send in a big check, as a retainer, for them friendly, slick talking strangers, to start the design work.
The designing and building parts, are practical money makers for the designers. That is where the practicality ends.
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VSEPR_VOID
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| Quote: Originally posted by Melgar | If you want hexane, I'd recommend distilling it from gasoline before I'd recommend whatever crazy route it looks like you're thinking of trying.
Alternately, heptane is virtually identical in its solvating properties and the only major difference is a somewhat higher boiling point. And heptane
is what's left over when you distill the diethyl ether (very valuable solvent) out of starting fluid. Starting fluid is perhaps 70-80% n-heptane, and
I've started using it a lot more in recent years just due to the fact that it comes as a byproduct of obtaining ether. |
I believe that Explosions&Fire on YoutTube made a video on that and had some success.
Within cells interlinked
Within cells interlinked
Within cells interlinked
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CaptainPike
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Fractionate some naphtha? This I have done, if you live in the US you can get it at any hardware store. If you're lucky, you might find Sunnyside
Light naphtha, it has more lower boiling point hydrocarbons.
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Bert
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I have a gallon can of "Bestine Rubber Cement Reducer". It is a technical grade of n-heptane.
Look at the SDS for Colman camping fuel sold by the gallon at Wal-Mart, etc. It is mostly cyclohexane.
Rapopart’s Rules for critical commentary:
1. Attempt to re-express your target’s position so clearly, vividly and fairly that your target says: “Thanks, I wish I’d thought of putting it
that way.”
2. List any points of agreement (especially if they are not matters of general or widespread agreement).
3. Mention anything you have learned from your target.
4. Only then are you permitted to say so much as a word of rebuttal or criticism.
Anatol Rapoport was a Russian-born American mathematical psychologist (1911-2007).
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unionised
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The idea of reducing glucose to hexane is interesting, but it seems unlikely to be practical.
If I want a fairly volatile, alkane solvent I use cigarette lighter fuel (Zippo fuel).
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JBSC
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to aga
to aga: if you want to see experiments then go to my channel on youtube or BITchute. I do stuff. I do not just talk about it. But i am learning
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subskune
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glucose can be converted to sorbitol (hexanehexol) quite easily, maybe a process similar to here:
http://www.sgc.se/ckfinder/userfiles/files/SGC198.pdf
can be created to convert the hexanhexol to hexane (similar to the conversion of the glycerol to propane in the article).
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aga
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Cheers. I found it, but religion really isn't my thing.
https://www.youtube.com/watch?v=TY6u0Krdphg
[Edited on 25-6-2018 by aga]
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roXefeller
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| Quote: Originally posted by Bert | I have a gallon can of "Bestine Rubber Cement Reducer". It is a technical grade of n-heptane.
Look at the SDS for Colman camping fuel sold by the gallon at Wal-Mart, etc. It is mostly cyclohexane.
|
When I look it up it seems that cyclohexane might be one of the lesser components. Given the reported boiling point, it seems to be mostly n-heptane.
Attachment: ColemanSDS.pdf (221kB)
This file has been downloaded 363 times
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unionised
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| Quote: Originally posted by roXefeller | | Quote: Originally posted by Bert | I have a gallon can of "Bestine Rubber Cement Reducer". It is a technical grade of n-heptane.
Look at the SDS for Colman camping fuel sold by the gallon at Wal-Mart, etc. It is mostly cyclohexane.
|
When I look it up it seems that cyclohexane might be one of the lesser components. Given the reported boiling point, it seems to be mostly n-heptane.
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Easy to check; put it in the fridge.
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Texium
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Thread Moved
25-6-2018 at 10:46 |
BaFuxa
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This winter I needed hexane to extract some extractives from some wood, I obsessed over hexane ( the n-hexane is quite expensive to buy actually) and
in the end I just distilled the hexane isomers 50-68°C from gasoline and they did the job, it is just one non-polar molecule amongst many.
Potential counts for nothing until realized.
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