Sciencemadness Discussion Board - aga Does Decarboxylation

aga Does Decarboxylation

aga - 14-9-2015 at 12:48

Appologies for arriving here, however it was inevitable, a bit like the common cold getting to you eventually.

Today 25g of salicylic acid had some fire under it in a distillation rig, following Nile Red's video to produce Phenol :-

https://www.youtube.com/watch?v=A0e0BDEE4Ic

Not having a 'short distillation setup' (which looks pointless) i just did this :-

It worked OK until the boiling flask got low on juice, and no more distillate came over, so i swapped from 250ml to a 50ml boiling flask and 25ml receiver :-

This didn't work either as the condensation front was having a hard time getting up to the stillhead, so i added some insulation :-

... which works fine !

Tomorrow vac distilling a couple of times to get a few g of Phenol.

Oh the Joy and smell of burnt plastic !

[Edited on 14-9-2015 by aga]

Little_Ghost_again - 14-9-2015 at 13:06

In the first pic isnt the thermometer a bit low?

aga - 14-9-2015 at 13:15

It would be for Scotland, yes, then i remembered where i was.

[Edited on 14-9-2015 by aga]

The Volatile Chemist - 14-9-2015 at 14:06

HAHAHA

Aga... just in case you actually didn't get what he meant, it's lower than the branch to your 'condenser', so the crossover vapor temp. wouldn't be accurate. Not that it matters too much.
Awesome synth, by the way. If I ever pick up some Salicylic acid, I'll try it. Where'd you get yours?

UC235 - 14-9-2015 at 16:50

Uh, you do know that Nile Red's video is from my writeup in prepub, right? That last bit of liquid might not have been phenol at all, but phenyl salicylate or xanthone. Did the temperature rise a lot when it passed over?

aga - 14-9-2015 at 22:28

Quote: Originally posted by The Volatile Chemist

just in case you actually didn't get what he meant, it's lower than the branch to your 'condenser' .... Salicylic acid ... Where'd you get yours?

Yes, i did know, which is why it's corrected later. I was concerned that condensate would block the thinner nozzle of the vac adapter (which i thought was why the short path condenser was full of hot water in the utoob vid) and didn't notice until later.

Ebay !

Quote: Originally posted by UC235

Uh, you do know that Nile Red's video is from my writeup in prepub, right? That last bit of liquid might not have been phenol at all, but phenyl salicylate or xanthone. Did the temperature rise a lot when it passed over?

I did not know that UC235. I'll have a good read in pre-pub when i've gotten to the point that i can understand some of the writings.

Seems like an excellent & simple synthesis for beginners.

Yes, the temperature shot up to 210 C briefly then fell to just under 100, at which point the distillation was stopped.

aga - 14-9-2015 at 23:38

First ever vac distillation

Sure goes fast !

Certainly won't forget to put boiling chips in the pot again.

Oscilllator - 15-9-2015 at 01:43

Quote: Originally posted by aga

Certainly won't forget to put boiling chips in the pot again.

Sure. Just like I'll never leave the stopcock open on my sep funnel again...

aga - 15-9-2015 at 08:34

Starting with 25g salicylic acid the result after third distillation was a paltry 4.7g of (presumably) phenol.

Seeing as it forms crystals, would not a simple recrystallisation be easier for purifying the stuff after the salicylic acid is decarboylated to phenol ?

Oh, for a Beginners experiment this is a terrible one.

Phenol is rather poisonous, carcinogentic, crosses the skin barrier easily and burns the skin.

http://www.atsdr.cdc.gov/mmg/mmg.asp?id=144&tid=27

Naturally i got a drop of the stuff on my leg, and it stings like crazy !

15 mins washing in the shower was recommended, so i did that.

Seems i should have some PEG knocking about in case of skin splashes (should have done that synthesis first i guess).

Symptoms of Phenol induced CNS damage include "nausea ... dizziness ... loss of consciousness, coma".

Thankfully this all home territory.

The Volatile Chemist - 17-9-2015 at 14:10

That's too bad. Have you tested it to see if it is phenol?
It seemed like an easy process... I know the feeling. I thought making some CaCl₂ from my reagents would be easy. Nope. Too many fumes, too many impurities in the HCl (The solution was bright YELLOW...) and the Plaster of Paris (I was going to filter out the Calcium Sulfate).

PHILOU Zrealone - 18-9-2015 at 16:32

Phenol is readily sublimable while salicylic acid is not...no need for distillation and consequent losses!

aga - 19-9-2015 at 11:27

Quote: Originally posted by The Volatile Chemist

I thought making some CaCl₂ from my reagents would be easy.

CaCl₂ is relatively easy with the right starting reagents.

Get some white sea shells from the beach (best) or some limestone (more impurities) and dissolve it in HCl.

Avoid chalk. Tends to be Calcium Sulphate and other random crap.

When i did the Limestone version, it stank of sulphates.

CaCl₂ will never dry in air - it deliquesces.

I just dumped the solution/paste straight onto the hotplate.

That was the easist way to near anhydrous.

For proper anhydrous you'd have to melt it in a stream of dry argon or something.

The Volatile Chemist - 19-9-2015 at 14:08

"Strait onto the hotplate"??? :/ Sheesh...
I'll try that. (not onto the hotplate though, my hotplate's crappy as it is...)

IrC - 19-9-2015 at 14:38

Quote: Originally posted by aga

Seems i should have some PEG knocking about in case of skin splashes (should have done that synthesis first i guess).

I searched to no avail, why I wish such terms were always defined at least once in any thread. All I got was:

PEG or Peg may refer to:

Devices

Clothes peg, a fastener used to hang up clothes for drying
Tent peg, a spike driven into the ground for holding a tent to the ground
Tuning peg, used to hold a string in the pegbox of a stringed instrument
Piton, a metal spike that is driven into rock to aid climbing
PEG tube, a medical device, that is, a percutaneous endoscopic gastrostomy tube
Foot peg, a place to put one's foot on a vehicle such as a motorcycle

Science and computing

Peg (unit), a measure used in preparing alcohol, from 1 to 2 fluid ounces
Pegasus (constellation), a constellation named after Pegasus
Percutaneous endoscopic gastrostomy, a medical procedure
Polyethylene glycol, a chemical polymer

Parsing expression grammar, a type of formal grammar used in mathematics and computer science
PCI Express Graphics (PEG), a port for computer graphics cards

Recreation

Peg, a rule in the game of backyard cricket
Peg (fishing), an area set aside for an angler
Peg solitaire, a board game for one player
PEG: Pinnacle Entertainment Group, a game company

People

Peg, an abbreviation of Peggy (given name), itself a diminutive of the name Margaret.

Transportation

PEG, the National Rail code for Pegswood railway station
PEG, the IATA airport code for San Egidio Airport

Other uses

PEG or PEGA channels, public, educational, and government access cable TV channels in the United States
Peg (currency), or Fixed exchange-rate system, a system to value currencies
PEG ratio, price/earnings to growth ratio, a stock price analysis tool
"Peg" (song), a song by Steely Dan
Mnemonic peg system, a memory aid
Program for the Exceptionally Gifted, a program at Mary Baldwin College
Winnipeg, Manitoba, Canada, nicknamed "The Peg"
Treenails used in woodworking joints such as timber framing, holds joints together, particularly the mortise and tenon joint. Also called a peg, pin or dowel.

Somehow I get the feeling none of this wiki page covers what you meant except possibly 'Polyethylene glycol, a chemical polymer'. Even so I'm not sure what use this would be for Phenol skin poisoning. A common wire enamel stripper called Strip-X I used daily years ago was IIRC nearly pure Phenol and I had many problems from it, not the least of which were blinding headaches that made one wish a safe would land on it to put an end to the suffering. Damn near no information of the danger of working with Phenol was provided with the bottle so putting it on a towel and cavalierly running a wire through it for stripping was commonly done. Later study online of the danger of working with Phenol reminded me of the old 1800's books I read where untrained people toyed with HF, Ammonium Bifluoride, HCN and many other chemicals at home.

aga - 19-9-2015 at 15:00

As per the reference given in my 5th post in this topic, PEG refers to polyethylene glycol.

I assume you decided to Type a lot of crap rather than bother to read the rather important reference to the medical handling procedures where phenol poisoning is suspected.

Please, do not repeat this synthesis right now.

You might not survive, and despite this particular gigantic inbicilliosity, you're one of the good guys, and i'd rather that you live, and do some amazing chemistry one day.

IrC - 19-9-2015 at 15:49

I didn't type a lot of crap I copied and pasted it. I also did not read the very long link you posted as I have no need to do this experiment and decades ago learned the value of not accumulating chemicals I do not have an actual use for. Too many troublesome experiences in years past trying to safely dispose of hazardous chemicals I collected but never really needed taught me that. My complaint was merely directed towards using an abbreviation in a thread without at least defining it once. If I ever do any more amazing things in science this late in life I doubt it will involve chemistry. Most likely it will revolve around some combination of mega-volts, mega-amps, plasma, radiation and/or electro-gravitic UFO's. What chemistry I do now is related to such endeavors as it is required.

aga - 19-9-2015 at 23:49

Quote: Originally posted by IrC

the value of not accumulating chemicals I do not have an actual use for.

Very wise words IrC.

I'll dispose of ~50ml of chloroform today seeing as it has sat in a drawer for about a year.

aga - 20-9-2015 at 11:41

Chloroform all safely wafted away on the wind.

Now for the Phenol. Anyone any ideas of what to do to render it safe for disposal ?

Googling has returned hundreds of 'label it and put in the chem waste bin' which seems Lame considering that many of those papers were from academic labs.

Also, what was the brown tarry goo left over in the boiling flask ?

Has a post been deleted ? I feel sure there was some mention of using a 0.2mm orifice made from a glass pipe instead of boiling chips in vac distillations.

PHILOU Zrealone - 20-9-2015 at 14:10

Bis repetita:
Sublimation of warmed reaction mixture on a cold glass surface will deposit only the sublimated phenol and not the salicylic or biphenyl or tarry material.

aga - 20-9-2015 at 14:24

Noted the first time.

Quam ob causam dixisti repetere? Ego experiri.

After that, how to destroy it, as in render safe for disposal ?

NaOH ?

IrC - 20-9-2015 at 20:31

Quote: Originally posted by aga

Noted the first time.

Quam ob causam dixisti repetere? Ego experiri.

After that, how to destroy it, as in render safe for disposal ?

NaOH ?

https://en.wikipedia.org/wiki/Phenol

"Phenol is easily neutralized by sodium hydroxide forming sodium phenate or phenolate, but it being weaker than carbonic acid cannot be neutralized by sodium bicarbonate or sodium carbonate to liberate carbon dioxide

C6H5OH + NaOH → C6H5ONa + H2O"

aga - 21-9-2015 at 07:39

Couldn't face the cleanup again, so just destroyed the phenol instead.

The IrC approach to making & keeping nasty stuff you don't immediately need is really very sensible.

Also saves space.

I'll remember the sublimation tip PHILOU Z, thanks.

The Volatile Chemist - 22-9-2015 at 18:39

The brown tarry goo was: tar.
In o-chem, from what little I've done and seen, tar forms because of decomposition when working at high heat all the time. One synth on versuchschemie for making angelase from fructose and HCl made what looked to be 100 grams of tar from the sugar's decomposition. I guess it's just commonlace, and why distillation is necessary a lot of the time.

HeYBrO - 23-9-2015 at 03:36

could of made phenolphthalein instead of wasting it...

aga - 23-9-2015 at 08:56

Waiting on some DCM to arrive to try to make pthalic anhydride from some gloves.

Will make the required phenol after i've got the other reagents for phenolpthalein.

macckone - 23-9-2015 at 20:07

https://www.youtube.com/watch?v=Vlh0YDRmZ0I

Bakelite?

HeYBrO - 25-9-2015 at 04:46

Quote: Originally posted by aga

Waiting on some DCM to arrive to try to make pthalic anhydride from some gloves.

Will make the required phenol after i've got the other reagents for phenolpthalein.

You don't need DCM, just use isoprapanol, or methanol as blogfast used i think.

aga - 25-9-2015 at 10:56

DOH !

(marches off to shed to dunk gloves in methanol ...)

j_sum1 - 25-9-2015 at 14:16

DCM is a simple distillation from paint stripper. You can even do it straight from the can.

blogfast25 - 25-9-2015 at 14:32

Quote: Originally posted by aga

Waiting on some DCM to arrive to try to make pthalic anhydride from some gloves.

With a BP of barely 40 C you need to use iced water for any refluxers/condensers.

The Volatile Chemist - 9-10-2015 at 11:42

Sheesh, that really is low. I use ice water usually, but I don't salt it (I don't know how much of a difference it would make) because my pump claims that it only works in fresh water (ie, not salt water like in marine aquariums).

Little_Ghost_again - 9-10-2015 at 11:49

Quote: Originally posted by The Volatile Chemist

Sheesh, that really is low. I use ice water usually, but I don't salt it (I don't know how much of a difference it would make) because my pump claims that it only works in fresh water (ie, not salt water like in marine aquariums).

what about adding antifreeze or maybe some IPA to lower the temperature.

kt5000 - 14-10-2015 at 12:19

Our college lab uses a chiller filled with antifreeze that's looped out to the condensor. It seems to work quite well. IPA would be a less toxic solution, though.

aga - 14-10-2015 at 12:25

Quote: Originally posted by blogfast25

With a BP of barely 40 C you need to use iced water for any refluxers/condensers.

New Soxhlet arrived today (donated the last one to a local Uni)

The DCM does not pass through any volume of these cut up vinyl golves, so the Soxhlet did not work at all.

Probably better to boil & reflux.

Trying it with merely Cold water was Interesting - the DCM at the top was refluxing from the heat of the incoming DCM stream

Reached the 3rd bulb of the Allhin condenser.

With Ice added, it did the same, just in the first, and half of the second bulb..

Edit:

Abandoned the attempt for now.

Cleanup was a bitch - the DCM makes these gloves into a mush that sticks to the glass like crazy.

[Edited on 15-10-2015 by aga]

kt5000 - 15-10-2015 at 15:55

I'm finding that polymer goos are a pain to clean up as well. I've dusted off my plans to extract something useful from that paint stripper. It left a mess in the test tubes. I can't imagine trying to scrub it out of a boiling flask. Hot methanol managed to dissolve a lot of it.

arkoma - 28-10-2015 at 17:14

OMG I have missed you nutters

Oscilllator - 28-10-2015 at 19:00

Quote: Originally posted by arkoma

OMG I have missed you nutters

He's Back! What took you so long?

Syntropymancer - 14-12-2015 at 18:08

Quote: Originally posted by UC235

And most, not all, of his videos are redone versons of both yours and myst, nothing against him he makes good videos, but I think he should be more apt to cite you guys