[woelen]

Benzene is a carcinogen, while toluene is not. This is for sterical reasons. The benzene molecule is flat and this shape allows it to slip into the crevices of DNA molecules/structures, where it affects the reproduction. Toluene is a flat molecule with a thick blob attached to it (the -CH3 has a tetraedal shape) and this makes it next to impossible for the molecule to go to those places, where benzene molecules can go. This makes toluene (and also xylenes) much less harmfull. The same is true for many other substituted benzene derivatives, such as benzoic acid, which as a -COOH, substituted for one of the H's.

[AWK]

Yeah benzene is quite nasty. I think the body has trouble hydrolising it therefore has trouble excreting it. Alternate solvents such as toluene are supposed to be better as the body has an easier time hydrolising and excreting it.

This is not a problem of hydrolysis, but  an oxidation

[mike]

This is not a problem of hydrolysis, but  an oxidation

oops thanks

[jdurg]

I think the acid in your stomach will degrade most of those structures before its ever a health problem. Is benzene a carcinogen?

I can remember one text book describe it as the mother of all carcinogens, i can't remember which but if you do a search for "mother of all carcinogens" virtually all results using that quote are with regards to benzene.

I have only heard that statement in regards to benzo-alpha-pyrene which is just a conglomeration of three benzene rings into one master structure (I believe).  VERY nasty stuff and only tiny quantities of it can cause cancerous growths.

[pantone159]

benzo-alpha-pyrene which is just a conglomeration of three benzene rings into one master structure

Benzo[a]pyrene has Five rings. 

A poor attempt to draw the structure (* = aromatic ring):

       *   *
*   *   *

[science2000]

hmm... so if i pour vinegar into coke which contains sodium benzoate... then add vitamin c for the catalyst would i get benzene? trace amounts? hmm so i guess if its true then the moral of the experiment would be don't eat salt and vinegar chips and down it with coca-cola, then eat an orange? hahaha... what are some other combination of foods that can turn into a plate of nasty carcinogens? hmm i wonder if this is an illegal topic. My intention was to let people know to be more safe.

Not even LiALH4 is strong enough of a reducing agent to reduce a benzoate salt to benzene. If that is how people feel benzene exists in cola, because of reduction by weakly reducing ascorbate salts, then it would be very impossible for even trace amounts of benzene to exist in cola. Some people will believe anything if they are ignorant of basic chemistry.

[billnotgatez]

science2000 or anyone-

I am curious. Did you read the papers and links mentioned in previous posts on this thread?

[limpet chicken]

If you want benzene, extracting it from cola, possible or not,  isn't going to give you good yields, if any, just decarboxylate sodium benzoate (sold dirt cheapo as food preservative, etc.) with NaOH, and distill off the benzene, (carefully, its the leukaemogen from hell), then redistill it from calcium chloride, or MgSO4.

[science2000]

No, I really haven't, billnotgatez. Why, has it been proven that trace amounts of benzene exist in cola? I thought it was just a wild theory.

[billnotgatez]

Benzene Production from Decarboxylation of Benzoic Acid in the Presence of Ascorbic Acid and a Transition-Metal Catalyst
J. Agric. Food Chem., VOl. 41, No. 5, 1993

I was curious is someone had read the above paper and could interpret it for us.

It appears that there was at least one study that showed above drinking water limits in soft drinks, but it has yet to be reported as replicated. They are talking parts per billion.

I have noticed on rare occasion when drinking diet caffeine free cola that there is an off taste. Since the product contains little in the way of food value it is hard to believe that it is biological degradation. One then wonders if there is a chemical process causing this off taste effect.

I wonder how hard it is to test parts per billion benzene content in cola. If it were easy enough then it would be great if citizen scientist across the world tested a small amount collected when imbibing their favorite cola.


It seems the limit in drinking water is 5 or 10 parts per billion and I wonder if 1 part per billion is carcinogenic.

[Will]

From what I've read, you will need to drink more than 20 litres of a drink containing benzene at 10 ppb to equal the amount of benzene you would breathe from city air in a day. Maybe we should all go around the city wearing respirators! Yay, I'm finally a Full Member .

[science2000]

There's probably many more things we're exposed to that's carcinogenic when you're talking about benzene in the ppb's. That must be the least of our worries.

[Borek]

Benzo[a]pyrene has Five rings. 

A poor attempt to draw the structure (* = aromatic ring):

       *   *
*   *   *