Sciencemadness Discussion Board » Fundamentals » Reagents and Apparatus Acquisition » New synthesis of Ethanol Select A Forum Fundamentals   » Chemistry in General   » Organic Chemistry   » Reagents and Apparatus Acquisition   » Beginnings   » Responsible Practices   » Miscellaneous   » The Wiki Special topics   » Technochemistry   » Energetic Materials   » Biochemistry   » Radiochemistry   » Computational Models and Techniques   » Prepublication Non-chemistry   » Forum Matters   » Legal and Societal Issues

Pages:  1
Author: Subject: New synthesis of Ethanol
Picric-A
International Hazard

Posts: 796
Registered: 1-5-2008
Location: England
Member Is Offline

Mood: Fuming

New synthesis of Ethanol

I have just thought of a way to make pure (anhydrous) ethanol from nail polish remover.
THis ethanol is not to drink, it is just a usefull solvent in all aspects of chemistry.
First Ethyl Acetate (acetone free nail polish remover) is reacted with Sodium Hydroxide to produce ethanol and Sodium Acetate. Use Sodium hydroxide in exess so you make shure all the ethyl acetate is used up.
CH3CO2C2H5 + NaOH → C2H5OH + CH3CO2Na
Then simply add water to remove esters that may be produced (i thknk...) and distill to get rid off sodium acetate and other gunk that could be in the nail polish remover.

Does this look feasable? i guess it would be cheaper than buying vodka and distilling it which is what i do at the moment.

any imput welcome,
DJF90
International Hazard

Posts: 2266
Registered: 15-12-2007
Location: At the bench
Member Is Offline

Mood: No Mood

There are problems with that method. First off you need to introduce the sodium hydroxide as a solution, and so water becomes part of the mixture, meaning that the alcohol is not anyhdrous, and a fractionation column would be needed to seperate out most of the water from the formed ethanol.

A large aount of sodium hydroxide solution is needed in comparison to the amount of ester you're going to hydrolyse as the hydroxide should be fairly dilute (about 1-2M) to reduce the amount of damage that could occur to the glassware (sodium hydroxide doesnt like glass much when its hot or concentrated). This means that to hydrolise the EtOAc you need a big flask, at least if you're doing it in meaningful amounts.

Even if you can get lab grade EtOAC (I've seen it priced at about £15 for 2.5ltrs) after the energy bill to heat the reaction mixture its cheaper to just buy the cheapest vodka you can (£7 a liter is about as good as it gets here) and distill that.
MagicJigPipe
International Hazard

Posts: 1554
Registered: 19-9-2007
Location: USA
Member Is Offline

Mood: Suspicious

Not to mention that most nail polish removers (all that I have seen) contain a whole bunch of other shit besides ethyl acetate. Methyl/butyl acetate, propylene glycol and various other esters and solvents. So, at best it would be contaminated with MeOH and BuOH and MeOH cannot be removed with conventional lab equipment and techniques.

I also don't understand why anyone would distill EtOH from vodka when grain alcohol is already 95%, decently pure and much cheaper (per unit of EtOH) than any other liquor.

Why vodka? Why?

EDIT
Not to mention EtOAc seems to be cheap and readily available in my area. Certainly it must be almost as easy to obtain in other areas. Well, at least if you look well.

[Edited on 5-2-2008 by MagicJigPipe]

"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
Polverone
Now celebrating 18 years of madness

Posts: 3164
Registered: 19-5-2002
Location: The Sunny Pacific Northwest
Member Is Offline

Mood: Waiting for spring

Some locales don't permit the sale of azeotropic grain alcohol (Everclear, etc.). If it's not available nearby, distilling from the next-strongest source of unadulterated ethanol may be the best option.

PGP Key and corresponding e-mail address
DJF90
International Hazard

Posts: 2266
Registered: 15-12-2007
Location: At the bench
Member Is Offline

Mood: No Mood

Thanks polverone. We don't have grain alcohol over here in the UK, and if we do I've never seen it. I think the strongest alcoholic beverage I have seen in the supermarkets is vodka, which would be the most economic thing to distil the ethanol out of right?
MagicJigPipe
International Hazard

Posts: 1554
Registered: 19-9-2007
Location: USA
Member Is Offline

Mood: Suspicious

Supermarkets?? Wow, just 5 years ago my state got the balls to start allowing wine sales at grocery stores. Gas stations: beer/flavored drinks only grocery stores: beers and wine only. The ONLY place allowed to sell liquor (except restaurants and bars) is liquor stores here.

What's the rationale for not selling Everclear (I buy Gem Clear which is much cheaper at less than $15 a liter. Still expensive, though, because of the liquor tax)? I just don't understand why not. I wonder how illegal it would be to ship liquor from the US to the UK or vice versa? "There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer DJF90 International Hazard Posts: 2266 Registered: 15-12-2007 Location: At the bench Member Is Offline Mood: No Mood Thats an interesting thought. It might not be illegal, so long as the correct tax is paid on it... I think the main problem is that we dont have liquor stores or an equivalent MagicJigPipe International Hazard Posts: 1554 Registered: 19-9-2007 Location: USA Member Is Offline Mood: Suspicious I know Absinthe can be shipped legally from the UK to the US. The US (or my state at least) just recently started allowing a drink with wormwood (sort of like alcoholic Red Bull is what it tasted like to me) to be sold. "There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer DJF90 International Hazard Posts: 2266 Registered: 15-12-2007 Location: At the bench Member Is Offline Mood: No Mood Yeah absinthe could be purchased here, havent seen it in the shop but I know its available online Thing is that its more expensive than just buying the cheapest vodka available and distilling it. Methylated spirits is a much better bet, as it its cheap and readily available in the hardware stores, but a good fractionation column is needed to provide adequate separation. Still purchasing glassware in portions off of ebay, just need a condensor and a receiver bend and I shall be sorted, already got a 45cm vigreux (fairly cheap too ) MagicJigPipe International Hazard Posts: 1554 Registered: 19-9-2007 Location: USA Member Is Offline Mood: Suspicious I don't think even a "good" column would acheive decent separation of EtOH and MeOH with just one distillation. You'd probably need several even with an extremely efficient setup. I found a 300mm Vigreux for 23USD. Is that good? "There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer DJF90 International Hazard Posts: 2266 Registered: 15-12-2007 Location: At the bench Member Is Offline Mood: No Mood Yeh I would think so... Over here a brand new 300mm vigreux with 24/29 joints is in excess of £60 ($90?)
MagicJigPipe
International Hazard

Posts: 1554
Registered: 19-9-2007
Location: USA
Member Is Offline

Mood: Suspicious

That's more like $118 USD.$23 USD is about 11.66 pounds.

[Edited on 5-2-2008 by MagicJigPipe]

"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
chemrox
International Hazard

Posts: 2953
Registered: 18-1-2007
Location: UTM
Member Is Offline

Mood: LaGrangian

EtOH is routinely mixed with MeOH here to make "denatured alcohol." The reason is its very difficult to separate the two. Distilling nail polish, ethylacetate, liquor, all seem extremely costly compared with brewing the stuff from grain, sugar, and/or dried fruit. If its that hard to get where you are, can you get E85 fuel? With that you can separate the alcohol (I think).

"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
MagicJigPipe
International Hazard

Posts: 1554
Registered: 19-9-2007
Location: USA
Member Is Offline

Mood: Suspicious

E85 still has 15% gasoline which is all kinds of crap.

Fermentation requires some knowhow and an initial investment. Distilling liquor would be simpler for small amounts, IMO. Even if you can't get PGA (pure grain alcohol).

I remember back when I was a teenager I used to drink PGA straight, occasionally. We used it as a dare sometimes. Or something you had to do if you lost a bet. As in, "when we drink tonight, you have to drink PGA straight if you ..."

Some people are dumb and don't realize that a shot of PGA contains the same amount of alcohol as 3 shots of normal liquor. Then they proceed to drink the same volume of PGA that they would normal liquor. A friend of mine did that and almost died. He turned gray. How can people be so ignorant?

EDIT
Chemrox, I think that is the way most EtOH is denatured. EtOH denatured with MeOH is very common.

[Edited on 5-2-2008 by MagicJigPipe]

"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
evil_lurker
International Hazard

Posts: 767
Registered: 12-3-2005
Location: United States of Elbonia
Member Is Offline

Mood: On the wagon again.

Speaking from experience, you need at least a 300mm packed hempel to get even halfway decent seperation from 40% alcohol.. even then you'd do good to average 85-88% over the course of a second run.

A 300mm vigreux would do good to hit 80% IMO.

Not all chemicals are bad. Without chemicals such as hydrogen and oxygen, for example, there would be no way to make water, a vital ingredient in beer.
MagicJigPipe
International Hazard

Posts: 1554
Registered: 19-9-2007
Location: USA
Member Is Offline

Mood: Suspicious

Well, then why can't someone just supply pure grain alcohol? If I thought it would be perfectly legal I would do it. But the alcohol laws in this country are so complex and convoluted one would almost need a lawyer to do it right.

Damn congress and the ATF (BATFE? BATF? What the hell are they now, anyway? I think Sauron mentioned ATFE.)

It no longer includes "bureau" in the name? Is that some sort of lame attempt to distance itself from "bureaucracy"?

"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
not_important
International Hazard

Posts: 3873
Registered: 21-7-2006
Member Is Offline

Mood: No Mood

It's not just the US Federal government, although they do come into play for alcohol entering the USA and distillation (oops - and exporting http://www.ttb.gov/ ).

According to http://en.wikipedia.org/wiki/Alcohol_laws_of_the_United_Stat... there are a number of state and local level laws.

 Quote: Florida Sale, processing, or consumption of any liquor or spirit of greater than 153 proof is illegal. West Virginia 6% ABV Cap on Beer. No Sunday liquor sales. No sale of 95% ABV spirits allowed in Morgantown or Huntington (and soon statewide).
MagicJigPipe
International Hazard

Posts: 1554
Registered: 19-9-2007
Location: USA
Member Is Offline

Mood: Suspicious

Oh, it's worse here. No Sunday alcohol sales, period. No liquor sales past 11 o'clock on weekdays and no beer sales past 1am on any day.

Only bars are allowed to sell alcohol on Sunday or past 1am. And even those places have some kind of Sunday limit I think. People actually make decent money here by buying alcohol and selling it to alcoholics and rich drinkers on Sunday for double to price.

The alcoholics usually don't think ahead and are out of alcohol on Sunday. The Sunday sellers take advantage of this fact.

I wonder how long until PGA is illegal here. I suppose it wouldn't hurt to buy a few gallons when I get the chance. It's basically the only source of 95% non-denatured EtOH available to the average citizen.

I did some reading and apparently very few exceptions are given for companies to avoid the liquor tax on pure EtOH. Apparently, even pharmaceutical companies must use denatured EtOH (to avoid the tax) for synthesis as long as it doesn't appear in the final product.

[Edited on 5-3-2008 by MagicJigPipe]

"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
Hazard to Others

Posts: 226
Registered: 25-4-2008
Member Is Offline

Mood: Sunlight on a pure white wall.

 Quote: Originally posted by MagicJigPipe Supermarkets?? Wow, just 5 years ago my state got the balls to start allowing wine sales at grocery stores. Gas stations: beer/flavored drinks only grocery stores: beers and wine only. The ONLY place allowed to sell liquor (except restaurants and bars) is liquor stores here. What's the rationale for not selling Everclear (I buy Gem Clear which is much cheaper at less than $15 a liter. Still expensive, though, because of the liquor tax)? I just don't understand why not. I wonder how illegal it would be to ship liquor from the US to the UK or vice versa? I had asked someone knowledgeable in the topic why Everclear (Grain Alc. 95%) was not allowed to be sold in New York--the reason he stated was that too many people did not understand that it was not to be taken pure, and would get alcohol poisoning quite easily. A direct correlation was found between the sale of Everclear and deaths related to ethanol intoxication, so it was legislated. He did indicate that while it was not sold in civilian liquor stores, military bases likely still carried it for sale on base, and any quartermaster should be able to requisition it. Though he seemed to think this may change soon as well. A bit of my photography (usually chemisty/physics inspired): ShadowWarrior4444.deviantart.com/gallery Sauron International Hazard Posts: 5351 Registered: 22-12-2006 Location: Barad-Dur, Mordor Member Is Offline Mood: metastable MJP, what makes you think absinthe can be shipped legally from anywhere into the US? While absinthe is not illegal to possess in USA it is illegal to manufacture it, or import it. The FDA and ATFE frown on it. It is true that since the EU has legalized absinthe again, a lot of absinthe has been bootlegged into the US and no one has gotten very upset about it. But, that does not mean that it is legal to import. Furthermore absinthe tends to be expensive. I recommend 151 proof rum if yu can't get Everclear or Diesel or other 95% potable spirits in your state. If you can't get that look for 100 proof vodka. Only then try the 80 proof vodka. Sic gorgeamus a los subjectatus nunc. MagicJigPipe International Hazard Posts: 1554 Registered: 19-9-2007 Location: USA Member Is Offline Mood: Suspicious I just assumed it was legal since it is advertised so blatantly in catalogs and such. I know just recently a friend of mine ordered it from a major catalog (it was a kit that came in a SS box with SS shotglasses and swizzlesticks I think). I hardly drink anymore but I did taste it and I must say it is definitely an aquired taste. Not bad, though, for "hard" liquor. I could have sworn the "word around town" is that alcohol containing wormwood was "legal" again because of the new wormwood "beer" they started selling in my state. Perhaps it's on a product by product basis? Guess, I'll do some research on the FDA rulings. "There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer ordenblitz National Hazard Posts: 259 Registered: 18-7-2004 Location: Northwest Member Is Offline Mood: Bohr'd Has anyone here tried the proposed reaction: CH3CO2C2H5 + NaOH → C2H5OH + CH3CO2Na ? I have, several times, in various concentrations with lab grade reagents and it did not work at all. MagicJigPipe International Hazard Posts: 1554 Registered: 19-9-2007 Location: USA Member Is Offline Mood: Suspicious I've often thought about this reaction as a way of getting relatively pure and cheap EtOH, however, the word is it is not practical. Never tried it... I think you need water for the reaction to proceed. Has anyone tried it? "There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think, free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer shadow Hazard to Self Posts: 52 Registered: 17-10-2007 Member Is Offline Mood: No Mood After wasting many hours distilling liter after liter of 40 proof(20%) vodka, I finally switched to everclear 151 proof, 200 proof not being legal here, and had much better productivity. But, its$18 for 750 ml, nets around 566ml final product.
So for \$32 and a couple of hours watching a thermometer, you might get a liter, if you keep it out of your face.
After reading this thread however, I'm not sure how pure it is, and may do density tests. I plan to purify it anyway, I need it dry.

Pulverulescent
International Hazard

Posts: 792
Registered: 31-1-2008
Member Is Offline

Mood: Torn between two monikers ─ "hissingnoise" and the present incarnation!

If by dry, you mean anhydrous, shadow, you're in for an uphill battle!

AFAIK, bits of calcium metal are required to remove the last 5% of H20!

Why would you want it dry, anyway?---Just curious?

P
Pages:  1

 Sciencemadness Discussion Board » Fundamentals » Reagents and Apparatus Acquisition » New synthesis of Ethanol Select A Forum Fundamentals   » Chemistry in General   » Organic Chemistry   » Reagents and Apparatus Acquisition   » Beginnings   » Responsible Practices   » Miscellaneous   » The Wiki Special topics   » Technochemistry   » Energetic Materials   » Biochemistry   » Radiochemistry   » Computational Models and Techniques   » Prepublication Non-chemistry   » Forum Matters   » Legal and Societal Issues