Sciencemadness Discussion Board - Phenol From Glow Sticks

Phenol From Glow Sticks

Chemistry Alchemist - 25-8-2011 at 07:39

In a glow stick chemical reaction, a tiny amount of phenol is produced from the reaction, now carnival time is coming up in a month and i can get 100 glow sticks for 10 dollars + more glow stick inside the show bag, if i do one big reaction (open am all up then combine together all at once) how do i safely extract the phenol and maybe as well the solvent if it hasn't all reacted

redox - 25-8-2011 at 08:09

Isn't this the fourth topic you have started today? Whatever, it doesn't matter.

I was under the impression that it was trichlorophenyl oxalate in most glowsticks (TCPO). So I suppose that you could salvage some 2,4,6-trichlorophenol by what you are suggesting.

Why do you want phenol? Do you have any use for it? You may have more luck running a diazotisation on aniline to phenol. Judging from your posts you watch Youtube videos a lot. The youtube user "myst32yt" has a pretty good video on the process. You might want to check it out.

[Edited on 25-8-2011 by redox]

Chemistry Alchemist - 25-8-2011 at 08:13

yeah its the 3rd post.... i like posting what i want to know, if i wanna do myst32YT version, i need aniline and i dont have it. i want phenol to make Phenolphthalein and i dont see any videos on extracting phenol with this method so i wanna try it out

Megamarko94 - 25-8-2011 at 08:15

you can get Phenolphthalein online... dont know if its worth making it....

Chemistry Alchemist - 25-8-2011 at 08:20

i like making things rather then buying, i just like teh science behind it all... it isnt science buying it online

Megamarko94 - 25-8-2011 at 08:24

Quote: Originally posted by Chemistry Alchemist

it isnt science buying it online

i completely agree with that but its just an indicator...

Chemistry Alchemist - 25-8-2011 at 08:26

yeah, if i had money and a supplier i would definitely buy it, but here in Australia, there isnt any chemical suppliers i have seen yet :/

Megamarko94 - 25-8-2011 at 08:34

yea i had the same problem untill i found local supplier..

Chemistry Alchemist - 25-8-2011 at 08:37

my local supplier is the local shops that i can buy the chemicals needed for what i do, people on youtube are always asking me wwhere i get all of them from and my answer is jjust the shops

The WiZard is In - 25-8-2011 at 09:56

Quote: Originally posted by Chemistry Alchemist

yeah, if i had money and a supplier i would definitely buy it, but here in Australia, there isnt any chemical suppliers i have seen yet :/

Phenolphthalein is (most likely was) used in OTC laxatives,
perhaps you could extract it.....?!

From El Merck Index 14th Edition.

Monograph Number: 0007243
Title: Phenolphthalein
CAS Registry Number: 77-09-8
CAS Name: 3,3-Bis(4-hydroxyphenyl)-1(3H)-isobenzofuranone
Additional Names: 3,3-bis(p-hydroxyphenyl)phthalide; a-(p
-hydroxyphenyl)-a-(4-oxo-2,5-cyclohexadien-1-ylidine)-o-toluic
acid; white phenolphthalein
Molecular Formula: C20H14O4
Molecular Weight: 318.32
Percent Composition: C 75.46%, H 4.43%, O 20.10%
Literature References: Prepn: A. Baeyer, Ber. 4, 658 (1871);
idem, Ann. 202, 36 (1880); M. Hubacher, US 2192485 (1940 to
Ex Lax). Reactions at various pH values: G. Wittke, J. Chem.
Educ. 60, 239 (1983). Polarographic analysis in aqueous soln:
M. M. Ellaithy et al., Farmaco Ed. Prat. 41, 326 (1986).
Subchronic toxicity studies: D. D. Dietz et al., Fundam. Appl.
Toxicol. 18, 48 (1992). Toxicology and carcinogenicity
studies: NTP Technical Report 465 (PB97-3390) 348 pp.
Comprehensive description of properties, clinical and laboratory
uses: F. J. Al-Shammary et al., Anal. Profiles Drug Subs. 20,
627-664 (1991).
Properties: White or yellowish white minute, triclinic crystals,
often twinned. mp 258-262°. d 1.299. Sol in 95% alcohol
and ether, slightly sol in chloroform. One gram dissolves in 12
ml alcohol, in ~100 ml ether. Almost insol in water. Sol in dil
solns of alkali hydroxides and hot solns of alkali carbonates
forming a red soln. pKa (25°C): 9.7. uv max (methanol):
205, 229, 276 nm (e 27261.147, 14692.144, 2006.369). Log P
(octanol/pH 7.4): 2.4. Shows color change from colorless in
acid range to purple at pH 8-9.
Melting point: mp 258-262°
pKa: pKa (25°C): 9.7
Log P: Log P (octanol/pH 7.4): 2.4
Absorption maximum: uv max (methanol): 205, 229, 276 nm
(e 27261.147, 14692.144, 2006.369)
Density: d 1.299

Derivative Type: Yellow Phenolphthalein
CAS Registry Number: 8053-05-2
Literature References: Produced in the mfg process prior to
final purification of white phenolphthalein. Contains yellow
bodies which impart characteristic color. Review of chemistry
and use as a laxative: M. H. Hubacher, S. Doernberg, J. Am.
Pharm. Assoc. Sci. Ed. 37, 261 (1948).
Properties: d420 1.290-1.296. mp 255-260°. One gram
dissolves in 12 ml alcohol, in 102 ml ether.
Almost insol in water. Sol in dil solns of alkali hydroxides and
hot solns of alkali carbonates forming a red soln. pKa (25°C)
: 9.7. uv max (methanol): 205, 229, 276 nm (e 27261.147,
14692.144, 2006.369). Log P (octanol/pH 7.4): 2.4. Shows
color change from colorless in acid range to purple at pH 8-9.

Melting point: mp 258-262°
pKa: pKa (25°C): 9.7
Log P: Log P (octanol/pH 7.4): 2.4
Absorption maximum: uv max (methanol): 205, 229, 276 nm
(e 27261.147, 14692.144, 2006.369)
Density: d 1.299

Derivative Type: Yellow Phenolphthalein
CAS Registry Number: 8053-05-2
Literature References: Produced in the mfg process prior to
final purification of white phenolphthalein. Contains yellow
bodies which impart characteristic color. Review of chemistry
and use as a laxative: M. H. Hubacher, S. Doernberg, J. Am.
Pharm. Assoc. Sci. Ed. 37, 261 (1948).
Properties: d420 1.290-1.296. mp 255-260°. One gram
dissolves in 12 ml alcohol, in 102 ml ether. Solns show a slight greenish fluorescence.

Melting point: mp 255-260°
Density: d420 1.290-1.296

CAUTION: Phenolphthalein is reasonably anticipated to be
a human carcinogen: Report on Carcinogens, Eleventh Edition
(PB2005-104914, 2004) p III-214.
Use: A 1% alcoholic soln as an indicator in titrations of mineral
and organic acids and most alkalies.
Therap-Cat: Cathartic.
Therap-Cat-Vet: Has been used as a laxative.
Keywords: Laxative/Cathartic.

not_important - 25-8-2011 at 19:55

For another method Try Google:

phenol from salicylic acid site:http://www.sciencemadness.org

ab5000 - 27-8-2011 at 12:10

Making it from Aspirin tablets is simplier.
First, extract the acetylsalycilic acid from the tablets: dissolve them in IPA, filter and crystallise adding cold water (about 5 times the IPA).
Then hydrolyse the ASA to salicylic acid with HCl (refluxing for 30 minutes).
Now just decompose the SA by rapidly heating it and it'll give you phenol.

redox - 27-8-2011 at 12:28

Quote: Originally posted by ab5000

Making it from Aspirin tablets is simplier.
First, extract the acetylsalycilic acid from the tablets: dissolve them in IPA, filter and crystallise adding cold water (about 5 times the IPA).
Then hydrolyse the ASA to salicylic acid with HCl (refluxing for 30 minutes).
Now just decompose the SA by rapidly heating it and it'll give you phenol.

Do you have a reference for the decomposition of salicylic acid? I have been searching, but I can't find anything. It seems like a great way to phenol.

ab5000 - 27-8-2011 at 12:51

Quote: Originally posted by redox

Quote: Originally posted by ab5000

Do you have a reference for the decomposition of salicylic acid? I have been searching, but I can't find anything. It seems like a great way to phenol.

In fact I read about the SA thermal decomposition on the Internet, but I never searched for a reference.
Anyway i found one: Marek Wesołowski, Thermal decomposition of salicylic acid and its salts. Unfortunately i can't access it because the site that hosts it is down: http://linkinghub.elsevier.com/retrieve/pii/0040-6031(79)85001-7
Hopefully it'll be back soon

#maverick# - 28-8-2011 at 21:17

phenol can be made from by heating SA with CaO

Dr.Bob - 29-8-2011 at 11:47

Quote: Originally posted by Chemistry Alchemist

In a glow stick chemical reaction, a tiny amount of phenol is produced from the reaction, now carnival time is coming up in a month and i can get 100 glow sticks for 10 dollars + more glow stick inside the show bag, if i do one big reaction (open am all up then combine together all at once) how do i safely extract the phenol and maybe as well the solvent if it hasn't all reacted

redox is correct, the only phenol would be 2,4,6-trichlorophenol, and that would only be found in the used glow sticks, which you might be able to find really cheap after a concert or other event. It is rather toxic and smelly, I believe, as it is one of the compounds that has been found in small amounts in some medicines after pallets treated with it where used to store the products and the plastic bottles absorbed it.

But there is no useful amount of phenol in glow sticks. There are other ways to make it or find it, so I would look at the threads on that as a starting point.

Bob

Chemistry Alchemist - 1-9-2011 at 21:58

How would i be able to remove it from the remains of a glow stick? im thinking about doing a large scale reaction from this so i can get good results

#maverick# - 1-9-2011 at 22:32

it wouldnt be worth the effort you would next to nothing, unless u extract that little glass tub prior to breaking it, that has concentrated peroxide but depending on the brand it might be contaminated

Chemistry Alchemist - 1-9-2011 at 22:58

Yeah, im planning on cutting open the tube and mix the chemicals once all out of the tube... is the hydrogen peroxide 30% and is it mixed with anything?

#maverick# - 1-9-2011 at 23:08

i tested some and was around 18%, mines was contaminated but it might differ by brand, honestly the h2o2 is the only thing worth even extracting make sure u use disposable labware cuz the green goo is a pain in the ass to get off glassware

Chemistry Alchemist - 1-9-2011 at 23:25

the organic solvent that is in the glass tube, is it possible to extract that aswell or is it too hard to get the dye out of the solvent?

#maverick# - 2-9-2011 at 00:49

H202 is in da glass tube

Chemistry Alchemist - 2-9-2011 at 01:17

the dyes make a colored solution when dissolved into the solvent... in the glow sticks i get, the glass tube has the colored solution while the plastic tube is the clear solution

#maverick# - 2-9-2011 at 01:31

O ok. Mines was the glass tub had clear solution. Take a bit of the clear solution and mix with mno2 if gas evolution is observed then that's the h202

Chemistry Alchemist - 2-9-2011 at 01:42

How can i test the concentration of the H2O2?

#maverick# - 2-9-2011 at 02:31

Use an amount like 1 ml add mno2 And lead the o2 gas to an inverted graduated cylinder filled with water. Actually if u look up zhmapper on utube he has a vid on it

Chemistry Alchemist - 2-9-2011 at 05:12

oh, yeah i dont have a graduated cylinder?

Chemistry Alchemist - 6-9-2011 at 22:32

i just broke open 4 used orange glow sticks, and mixed it with water in a beaker... 3 layers formed, one with a lower density with water, then there was the water and then a heavier density liquid... the bottom one has the dye still in it, so what would be the top layer? it is a clear liquid...