Sciencemadness Discussion Board - phenol

phenol

kclo4 - 29-1-2005 at 22:54

whare can i get phenol

BromicAcid - 29-1-2005 at 23:05

Chemical suppliers, google, froogle, extration from sore throat spray, reaction of benzene with fentons reagent, reaction of a dizonium salt with hydroxide, I think there is a decarboxylation method to phenol via benzoic acid in the presence of some catalyst (a copper one I think), hydrolysis of acetylsalicylic acid follwed by recovery of the salicylic acid and decarboxylation.

Some off the top of my head, may be wrong

I put as much effort in to answering this as you did of posting it, you can find products containing pheonl by searching.

kclo4 - 29-1-2005 at 23:31

Sorry my internet is a peace of shit it is connected at 28.7 kbps and to make it all better we have a virus that keeps bringing up about : blank but I have been trying

Internet terrorist should burn in hell

garage chemist - 30-1-2005 at 06:00

Can salicylic acid be decarboxylated via the same procedure as benzoic acid, e.g. by heating sodium salicylate with NaOH/Ca(OH)2?

Decarboxylation of plain SA proceeds much too slow, and a part of the SA just sublimates.
It starts smelling like phenol after a short time, but this doesn't mean anything.

Esplosivo - 30-1-2005 at 07:18

Yes it can, the phenol product does have a brownish tinge though due to aerial oxidation and polymerization of the formed quinones. This is usually done qualitatively during analyses of organics, but I think it can be carried out on larger batches. I think it would be better to use multiple small batches than using one large batch - yields will probably show an increase. Sodalime you mentioned is probably better than NaOH alone. Hope this helps.

kclo4 - 30-1-2005 at 11:54

When BENZOIC ACID decomposes it emits toxic vapors and gas including phenol, benzene, and carbon monoxide according to msds so couldn’t you then bubble the gases from the decomposed acid threw sulfuric acid then react it with NaOH to get all the benzene to phenol

or would that change the phenol to somthing elts

Mumbles - 30-1-2005 at 18:50

That is why you don't decarboxylate straight benzoic acid. You decarboxalate the sodium salt with NaOH. It runs much cleaner.

Quote:

...then react it with NaOH to get all the benzene to phenol

BTW, benzene doesn't react with NaOH to produce phenol.

Cloner - 1-2-2005 at 15:09

According to the dangerouslaboratories site, salicylic acid does decompose into phenol during picric acid formation, in the stage of sulfonation. Unfortunately, it is not as easy as heating it to 150 degrees with sulfuric acid to obtain the well known dark sticky liquid that will contain phenol in sulfonated form.

uchiacon - 6-11-2009 at 21:17

Guys, does anybody know a common use or industrial use for it?
I came up with phenol resins, but the fuckers won't sell me any because the company forbids it.

Pharmacies are no go, chemical suppliers want $133 for 500g, so I'm going to try podiatry, but I doubt they use pure phenol.

Any other ideas gus?

not_important - 6-11-2009 at 21:40

These days it's either chemical suppliers, or industrial uses where they'll sell you a tanker car of it. If you have access to a time machine, you could by carbolic acid readily; make sure you bring along appropriately dated money.

It's still used for radical skin peels, but that's most likely a expensive medical product. Remember that if you do find a source such as that, it's not that difficult to purify the phenol.

If you don't need much then your best bet is to decarboxylate sodium salicylicate, as mentioned above.

If you need a lot, then fusion of benzenesulfonic acid with KOH or mixed NaOH/KOH is likely better. Of course if you can't buy benzene then you're back to making it via decarboxylation.

kmno4 - 6-11-2009 at 23:18

Phenol is very cheap reagent. For 1 kg of phenol of good quality (white or very little pink) you should give no more than ~20 american dollars (not 40 as I have written earlier, little problems with recalculations...

).

[Edited on 7-11-2009 by kmno4]

Eclectic - 7-11-2009 at 09:03

Heating ASA, Methyl Salicylate, Salicylic Acid with 92-96% H2SO4 should get you p-hydroxybenzenesulfonic acid. You can probably use that for most synths that call for phenol in sulfuric acid, or dilute and steam distill to recover pure phenol.

Does anyone know if benzenesulfonic acid would distill (190 C) from benzoic acid in hot sulfuric acid as a decarboxilation solvent? Perhaps with a little copper as catalyst?

[Edited on 11-7-2009 by Eclectic]

uchiacon - 7-11-2009 at 13:49

Oh, so when making trinitrophenol you can use salicylic acid instead of acetylsalicylic acid? I read up about synth of aspirin from salicylic, and it required acetic anhydride(narcots manufacture) and 85% phosphoric acid. Aspirin is 8 times the price in New Zealand as in other countries. Courtesy to monopolies.

The chemical supplier was telling me that the phenol was high analytical grade. Around $100USD for 500g lol. However I may not have a choice to buy from him, none of the industrial users want to sell me any.

If I'm also correct, phenol can't air freight? So I can't get it from America. I'm going to try more industrial users, but I doubt any will give me any.

entropy51 - 7-11-2009 at 14:19

Diazotize aniline in dilute H2SO4, let it warm up, and steam distill out the phenol. Works every time.

entropy51 - 8-11-2009 at 15:37

Might Oil of Wintergreen (methyl salicylate) be cheaper than aspirin? I once bought a large bottle in a pharmacy. It might be available in an aromatherapy shop. Or as horse liniment at a farm store. It might be a major ingredient in an OTC product for muscle soreness. Just a thought.

If you can get that you can hydrolyze with aqeous base at reflux and acidify to get salicylic acid. If need be you could decarboxylate to phenol or use it directly.

uchiacon - 9-11-2009 at 21:09

Well guys, I, for once, have actually exhausted all possible suppliers of phenol. I found several actually, all willing to sell me 200L of 90% phenol solution. Below that they would not go, and I've phoned 16 companies in total.

I'm actually surprised, I managed to find pentaerythritol, conc sulfuric, 70% nitric, cheap labware and many hard to obtain chemicals, but I just can't get phenol. The only suppliers of Methyl salicylate are pharmacies, selling it at about $20 for 100mls. Aspirin is ridiculously over priced, coming in at $5NZ for 15g acetylsalicylic acid, and after purification that will usually be reduced to 7-10g. If there is anybody else in New Zealand who has found a cheap source of any of these materials, I'd really love to know, I've been phoning arond these goddam companies for days.

Halp

Eclectic - 10-11-2009 at 02:39

http://www.gonative.co.nz/shop/Essential+Oils/Wintergreen+es...

garage chemist - 11-11-2009 at 02:33

If salicylic acid is too expensive for you, you can go via benzene.
Grind sodium benzoate together with NaOH, dry distill with strong heat, fractionate distillate to get benzene.

Then either nitrate, reduce, diazotise and steamdistill,
or sulfonate with conc. H2SO4 (reflux, slow reaction) and fuse sodium benzenesulfonate with NaOH.

Can you get benzoic acid for a reasonable price?

There is also an industrial method for phenol production that employs oxidative decarboxylation of benzoic acid with copper salts as catalyst. This directly gives phenol instead of benzene.
These are the patents for the process:

Dow Chemical, US 2 727 926, 1954 (W. W. Kaeding, R. O. Lindblom, R. G. Temple).
Dow Chemical, US 2 954 407, 1957 (W. H. Taplin).
Dow Chemical, US 3 235 588, 1962 (C. W. Weaver).

uchiacon - 11-11-2009 at 19:05

Well yes, I can get salicylic acid, but would I have to acetylise it for use in TNP manufacture?

I also found somebody who could sell Nonylphenol, could I change that into phenol? Looks like theres just a Carbon chain that I'd need to snap and I'd have phenol.

[Edited on 04-07-09 by uchiacon]

bbartlog - 12-11-2009 at 07:42

Quote:

Well yes, I can get salicylic acid, but would I have to acetylise it for use in TNP manufacture?

Note sure what you mean. Acetylating salicylic acid gives you aspirin. I would expect phenol to be part of the TNP synthesis (though I actually don't know anything about it) which means you would want to decarboxylate the salicylic acid, not acetylate it.

Quote:

I also found somebody who could sell Nonylphenol, could I change that into phenol? Looks like theres just a Carbon chain that I'd need to snap and I'd have phenol.

This is like saying you just need to pluck the head off a parking meter. Carbon chains are strong. I don't see any clean and easy way to just split off the alkane under kitchen chemistry conditions, it looks like a job for a petroleum cracking plant. I could imagine a stepwise attack on the end of the chain (oxidize, decarboxylate, repeat) but that's hardly a practical way to remove nine carbon atoms.

uchiacon - 12-11-2009 at 13:22

Hm, well I might be able to get some last leads on this phenol, but it isn't looking promising. I will probably have to go with salicylic acid, but I'll need to find a synth somewhere, I don't think I'm as advanced as you lot to be able to calculate whats needed.

I dunno, maybe after 5-6hours combined(throughout the week) of searching, I might be able to find a bit. Fingers crossed. Although, I did find a small supplier who can sell me a glass aspirator for $38NZ, so I'm pretty happy about that. My last metal aspirator was eaten away by acid, even when the seller told me it should be fine.

[Edited on 04-07-09 by uchiacon]

bbartlog - 12-11-2009 at 13:42

The patents garagechemist posted (esp. the oldest one) look pretty good, actually. The main aim of the first one is to replace a carboxyl with a hydroxyl group (they're trying to turn benzoate into phenol); which, if applied to salicylate, would give you catechol instead of phenol. *However*, they also mention that the benzoate decarboxylation proceeds to benzene if no oxidizing agent is supplied (e.g., no air), so trying their method on salicylic acid, anaerobically, might get you a decent yield of phenol. The conditions they cite are quite mild as such things go, very stovetop friendly.
I'm actually in the process of doing various experiments with aspirin / salicylic acid myself, including some attempts to synthesize phenol (there is a thread in 'Beginnings'). So far I haven't gotten anywhere close to decent yield, though I did produce a couple grams of calcium phenate last night. I'll post once I've made an attempt with a copper catalyst; I have a couple grams of copper carbonate I'm not using for anything else...

Copenhagen - 20-6-2010 at 18:43

Quote: Originally posted by Eclectic

Heating ASA, Methyl Salicylate, Salicylic Acid with 92-96% H2SO4 should get you p-hydroxybenzenesulfonic acid. You can probably use that for most synths that call for phenol in sulfuric acid, or dilute and steam distill to recover pure phenol.

Does anyone know if benzenesulfonic acid would distill (190 C) from benzoic acid in hot sulfuric acid as a decarboxilation solvent? Perhaps with a little copper as catalyst?

[Edited on 11-7-2009 by Eclectic]

Hello all. I would like to introduce myself and say hi to all since this is my first. You have a very respectable site and I enjoy the level of accessible scientific discussion available here.

Here is a little about me:

I’m a college student. I like to read and search for the subtleties that explain why things work the way that they do. I’m not a big fan of spewing out useless facts for the purposes of mental maste… I mean self gratification. I believe that facts should be boiled down to their simplest components. I try to feel for their essence by reading carefully and cross referencing. I don’t try to rote memorize chemistry, I try to see how everything is connected. I’d rather understand the “boring” basic stuff and apply it to a more advanced purpose than to memorize a sexy fact and ad hoc a reason for why it is. I can be better sure that I understand by asking a question not asked of me, making my hypothesis and then searching the textbooks to see if I’m right. If I’m right then maybe I understand. I don’t like it when the answer is told to me before I have a chance to think it through. A question that I get the answer for without thinking is a wasted question. For this reason I’m a big fan of UTFSE but to be honest I’d rather UTFLC because I’m already ADD.

If I really understand then maybe I can think of my own questions and I can carefully test them with careful planning and cross-referencing and performing a quantitatively and scientifically performed experiment. I think that your site embodies this approach. You guys exemplify what to me is the spirit of science.

I have come to appreciate the attention to detail that is required to perform an experiment. When done properly I believe that when a scientist makes a mistake he/she should most times know right away that his/her experiment is ruined rather than for him/her to have to wait hours later and see his/her botched results. This way when the results deviate from theory he can be more certain that a phenomena not accounted for in the planning of the procedure has exerted its influence. It’s very fulfilling to be able to cautiously set up an experiment let it run while confident that, by adherence to proper form it will turn out as planned. I’m not an expert but I believe that chemistry is a beautiful science. I can be mistake prone sometimes but I don’t make the same mistake twice, well at least not in the same exact way.

Anyways, sorry for being long winded.

To Eclectic:

I think so according to my first attachment. It says that a number of phenolic compounds with electron-withdrawing groups can be converted in this way. Heated to above 200C with copper benzoate salt. The third paper that is attached also says that cupric benzoate is the key compound to catalyze this reaction. The paper, like so many others, does not give the catalytic ratio. Below the first reference I’ve attached one that does mention the ratio. Although, this is for benzene conversion to phenol. I only can see the first page in lieu of an abstract so I don’t know the ratio.

I’m with you on your suggestion of doing an acid-catalyzed sulfonation/decarboxylation followed by a desulfonation by heating and passage of steam. I want to use my glassware and it shouldn’t get chewed up this way. I am going to attempt this route using Acetylsalicylic acid and sulfuric acid. I’m going to mix acetylsalicylic acid with 95% sulfuric acid and heat to 90 degrees Celsius under reflux. Then I will use to stoichiometry adjust the volume of the reaction mixture such that the sulfuric acid concentration is around 74%. I will heat to 130 C or boiling and steam distill phenol.

I was going to attempt the benzoic acid + copper route for phenol first but I will do this experiment instead since I haven’t procured any benzoic acid yet. I was going to start with the ratio from the benzene to phenol conversion as my starting point and run a number of trials with various mole % ratios for the cupric benzoate.

Attachment: DecarboxylationSalicylicAcids.MDI (398kB)
This file has been downloaded 886 times

Attachment: BenzeneToPhenol.pdf (248kB)
This file has been downloaded 1382 times

Attachment: PhenolCopper.pdf (496kB)
This file has been downloaded 1440 times

zed - 22-6-2010 at 01:50

Huh? Try looking for it under the name carbolic acid. Maybe your farm supply company will have it.

Nasty stuff phenol. If it contacts bare skin, it will burn the living crap out of you. Meanwhile, you will have no idea you have been afflicted.

It's a powerful local anesthetic. You feel no immediate pain, but huge blisters form at point of contact.

It's cousin eugenol, found in clove oil, is sometimes used to numb toothache pain.

Pheew! I went out looking for phenol. The common Chemical Companies are asking a hundred bucks a pound for it. Unreasonable.

[Edited on 23-6-2010 by zed]