Sciencemadness Discussion Board - Looking for Long Chain Alcohols or Ketones

Looking for Long Chain Alcohols or Ketones

VSEPR_VOID - 8-7-2018 at 20:07

I am looking for long chain alcohols and ketones. Does anyone have any recommendations on what to looks for? Alkenes and aryl compounds will not do.

So far I have considered and found sources for:
n-butyl alcohol
t-butyl alcohol

Methyl ethyl ketone
acetone

j_sum1 - 8-7-2018 at 22:48

I don't think any of these qualify as long chain.
You did not specify what application you want them for. It might be that you have to make them yourself -- time to learn about Grignards.
As a starting point you might want to look at some of Nurdrage's recent videos where he produced some branched long-chain alcohols for his sodium production experiments. Then, if you feel this kind of technique is within your reach, do a bit of reading on the background theory and practice. Then prepare your equipment and go for it.

unionised - 9-7-2018 at 01:22

You can simply buy them
https://en.wikipedia.org/wiki/Cetostearyl_alcohol

What do you want them for?

wg48 - 9-7-2018 at 02:10

Cetostearyl Alcohol from ebay uk £11/kg.

VSEPR_VOID - 9-7-2018 at 03:38

Quote: Originally posted by j_sum1

I don't think any of these qualify as long chain.
You did not specify what application you want them for. It might be that you have to make them yourself -- time to learn about Grignards.
As a starting point you might want to look at some of Nurdrage's recent videos where he produced some branched long-chain alcohols for his sodium production experiments. Then, if you feel this kind of technique is within your reach, do a bit of reading on the background theory and practice. Then prepare your equipment and go for it.

I would like the application to be kept a secret for now but expect a publication in a month or two, but it involve avoiding Grignards- no gringards can be used.

Cetyl alcohol looks like a great option. I think that it might be perfect.

Metacelsus - 9-7-2018 at 05:06

Behenyl alcohol (22 carbons) would be even longer, and is also commercially available (although I can't find any of the pure compound on Ebay, just skin creams that contain it).

VSEPR_VOID - 9-7-2018 at 09:32

Purity is a bonus. I think that cetyl alcohol will do. That leaves us with ketones. MEK is the longest chained ketone I can find.

What about secondary alcohols I might able to oxidize to ketones?

unionised - 9-7-2018 at 09:44

Dehydrate the cetyl alcohol, and rehydrate the alkene to get the 2-ol
Or convert it to a grignard and then react that with acetaldehyde.

You should be able to get MIBK and diacetone alcohol, but how useful those are depends on what you seek to do.

VSEPR_VOID - 9-7-2018 at 10:41

http://www.prepchem.com/synthesis-of-diacetone-alcohol/

Diacetone alcohol would be great but it seems a bit difficult to make. I want what I am working on to the accessible to other amateurs. Barium hydroxide, anhydrous potassium carbonate, and dry acetone is a bit too much to ask. It does however have the added bonus of being a tertiary alcohol, which might prove useful in other regards.

Are there any OTC or online sources of Methyl isobutyl ketone? That seems promising.

As a side note I found this well searching: https://www.ebay.com/itm/MEKP-Methyl-Ethyl-Ketone-Peroxide-H...

I did not know you could buy that.

JJay - 9-7-2018 at 11:44

I've had a heck of a time finding n-butanol in OTC products, and I think I will have to buy it.

walruslover69 - 9-7-2018 at 12:00

I believe calcium hydroxide could be substituted for barium hydroxide in the diacetone alcohol synthesis. You would still need a soxhlet extractor though.

VSEPR_VOID - 9-7-2018 at 12:09

Quote: Originally posted by JJay

I've had a heck of a time finding n-butanol in OTC products, and I think I will have to buy it.

I have about a liter of it right now but I need to get more. The only source I had is sold out on Amazon and I am afraid of them not restocking. Apart from that you can import it from the UK (maybe someone can set up a group buy its ~50 USD for 5 liters + shipping from the UK to US). There is also isobutyl acetate and other esters that are in some products.

Quote: Originally posted by walruslover69

I believe calcium hydroxide could be substituted for barium hydroxide in the diacetone alcohol synthesis. You would still need a soxhlet extractor though.

I have a pressure equalizing funnel that I could use instead. NerdRage, the chemistry prophet it seems, did a video on it. If that is indeed the case I should try it. I will also have to try using sodium carbonate in lieu of potassium carbonate. Acetone is cheap enough that any yield is acceptable. When/if I do it I will make a separate publication about it.

[Edited on 9-7-2018 by VSEPR_VOID]

CobaltChloride - 9-7-2018 at 12:30

At least where I live, n-butanol is present in a couple of OTC products:
-as a denaturant in some brands of rubbing alcohol
-as a major component in some brands of nitrocellulose resins thinner/ general paint thinner
Maybe you could also find it in these sources

JJay - 9-7-2018 at 12:55

Quote: Originally posted by CobaltChloride

At least where I live, n-butanol is present in a couple of OTC products:
-as a denaturant in some brands of rubbing alcohol
-as a major component in some brands of nitrocellulose resins thinner/ general paint thinner
Maybe you could also find it in these sources

It's not hard to find chemical suppliers who are willing to sell it, but it's hard to find anyone willing to ship it as a consumer commodity, and I'd rather not pay a hazmat fee for it.

VSEPR_VOID - 9-7-2018 at 23:01

Quote: Originally posted by JJay

Quote: Originally posted by CobaltChloride

It's not hard to find chemical suppliers who are willing to sell it, but it's hard to find anyone willing to ship it as a consumer commodity, and I'd rather not pay a hazmat fee for it.

https://www.ebay.com/itm/n-Butanol-99-4-ACS-5-Litre-Butyl-Al...

This is the best source I can find. I would be happy to do a group buy on it. shipping it. I could do with a few litters of it so all I need is someone in the UK who is willing to forward it to me.

walruslover69 - 10-7-2018 at 07:03

After looking into it alittle more it seems there are a lot of catalysts for the condensation reaction with aceteone to produce diacetone alcohol. I read that molecular sieves can also work. Calcium hydroxide is still not a bad choice. Using molecular sieves will produce some mesityl oxide through the dehydration reaction but since acetone is cheap yield isn't that big of a concern. You could also just use magnesium sulfate to dry the acetone. Pretty much anything will work.

[Edited on 10-7-2018 by walruslover69]

CobaltChloride - 10-7-2018 at 07:19

Actually, barium hydroxide is a lot more soluble than calcium hydroxide, so that isn't the reason they use Ba(OH)2

walruslover69 - 10-7-2018 at 07:37

Ya, I probably should have checked that. It must just be that its a stronger base.

VSEPR_VOID - 10-7-2018 at 11:19

The literature says that I would need to reflux the acetone for 100 hours. I will have to figure out how to do that. I have work and don not want to leave a boiling flask of highly flammable gas and liquid in my house. I do not have any calcium or barium hydroxide but I am sure I could order some quick lime or make it from calcium chloride (which I also need to buy).