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benzoate to benzene

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dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

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Apr 5, 2006, 11:06:25 PM4/5/06
to
There is now a big "hue and cry" that companies are "putting
benzene on our children's drinks" (soda).

Notwithstanding the fact that there are no documented cases of
benzene causing cancer (it cites to the bone marrow), are there
preservatives that would be suitable to the task that potassium
or sodium benzoate now serve?

David A. Smith

PS. hanson, I know you'll enjoy the chance to vent here...


Borek

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Apr 6, 2006, 4:13:28 AM4/6/06
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On Thu, 06 Apr 2006 05:06:25 +0200, dlzc1 D:cox <T:n...@nospam.com>> wrote:

> Notwithstanding the fact that there are no documented cases of
> benzene causing cancer (it cites to the bone marrow), are there

You mean they are lying to me since seventies? Shit.

While current hype is idiotic I think aromatic hydrocarbons where one of
the first compounds for which cancerogenity was proven - wasn't it some
skin cancer common between british chminey sweepers that made the case?
IIRC that was first time when "cancerogenity" appeared (even if I have no
idea how it was exactly called then).

Best,
Borek
--
http://www.chembuddy.com
http://www.ph-meter.info

H...@nospam.nix

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Apr 6, 2006, 8:19:44 AM4/6/06
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"Borek" <m.bor...@delete.chembuddy.these.com.parts> wrote in message
news:op.s7kugqvr26l578@borek...


I think you are pretty close, Borek. Those are some of the first references
I remember.

And I don't think there is any doubt at all about benzene being a
carcinogen.


dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

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Apr 6, 2006, 9:17:44 AM4/6/06
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<H...@nospam.nix> wrote in message
news:AH7Zf.64956$Jd.2...@newssvr25.news.prodigy.net...

>
> "Borek" <m.bor...@delete.chembuddy.these.com.parts> wrote in
> message
> news:op.s7kugqvr26l578@borek...
>> On Thu, 06 Apr 2006 05:06:25 +0200, dlzc1 D:cox
>> <T:n...@nospam.com>> wrote:
>>
>> > Notwithstanding the fact that there are no documented
>> > cases of benzene causing cancer (it cites to the bone
>> > marrow), are there
>>
>> You mean they are lying to me since seventies? Shit.
>>
>> While current hype is idiotic I think aromatic hydrocarbons
>> where one of the first compounds for which cancerogenity
>> was proven - wasn't it some skin cancer common between
>> british chminey sweepers that made the case? IIRC that
>> was first time when "cancerogenity" appeared (even if I
>> have no idea how it was exactly called then).

"carcinogenicity" or "carcinogen"

> I think you are pretty close, Borek. Those are some of the
> first references I remember.
>
> And I don't think there is any doubt at all about benzene
> being a carcinogen.

http://www.epa.gov/iris/supdocs/benz-sup.pdf
<QUOTE>
The best available human epidemiological data for evaluation of
cancer risk for benzene derive from studies of occupational
inhalation exposure.
<END QUOTE>

I read that wrong. Just because they concentrated on inhalation
exposure (est. 50% absorption), doesn't mean that oral exposure
(est. 100% absorption) doesn't end up with many of the same
issues.

http://www.epa.gov/ncea/pdfs/benzenef.pdf
<QUOTE>
Human epidemiologic studies of highly exposed occupational
cohorts have demonstrated that inhalation exposure to benzene can
cause acute nonlymphocytic leukemia and other blood disorders,
that is, preleukemia and aplastic anemia. Additionally, changes
in blood and bone marrow consistent with hematotoxicity are
recognized in humans and experimental animals.
<END QUOTE>

Notwithstanding my erroneous blanket statement, what other
chemicals can serve the same purpose as benzoate?

David A. Smith


Borek

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Apr 6, 2006, 11:17:21 AM4/6/06
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On Thu, 06 Apr 2006 15:17:44 +0200, dlzc1 D:cox <T:n...@nospam.com>> wrote:

>>> While current hype is idiotic I think aromatic hydrocarbons
>>> where one of the first compounds for which cancerogenity
>>> was proven - wasn't it some skin cancer common between
>>> british chminey sweepers that made the case? IIRC that
>>> was first time when "cancerogenity" appeared (even if I
>>> have no idea how it was exactly called then).
>
> "carcinogenicity" or "carcinogen"

Thnx. Polish words are sometimes derived from English or from some common
ancestor and usually spelling of English ones is obvious. Sometimes it is
not :(

> Notwithstanding my erroneous blanket statement, what other
> chemicals can serve the same purpose as benzoate?

Very good question. My take is that benzoates will be replaced, but in
10-20 years it will become obvious that the cure was worse than the
illness.

Madalch

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Apr 6, 2006, 1:50:22 PM4/6/06
to
> There is now a big "hue and cry" that companies
> are "putting benzene on our children's drinks"

Turning benzoic acid into benzene is not a reaction I would expect to
observe under biological conditions.

H...@nospam.nix

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Apr 6, 2006, 2:01:12 PM4/6/06
to

"Borek" <m.bor...@delete.chembuddy.these.com.parts> wrote in message
> Very good question. My take is that benzoates will be replaced, but in
> 10-20 years it will become obvious that the cure was worse than the
> illness.

The illness can be pretty bad.

But there might be alternative ways of sterilizing many food products which
may prove adequate without using chemical antimicrobials, among them
UV sterilization, ultrafiltration, flash heating etc.

It is my belief, perhaps incorrect, that a reasonably active reducing agent
is needed to convert benzoate to benzene. Omitting the ascorbic acid or
other reducing agents, or deactivating natural reductants might be adequate
to
prevent the problem in some types of food products.


dave e

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Apr 6, 2006, 2:31:12 PM4/6/06
to

benzoate and benzene are two entirely different compounds.

benzoate metabolism, seen here:
http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/misc/benzoate.html

does not produce benzene as an intermediate.

Dave

Anonymous via the Cypherpunks Tonga Remailer

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Apr 6, 2006, 2:55:41 PM4/6/06
to
> The best available human epidemiological data for evaluation of
> cancer risk for benzene derive from studies of occupational
> inhalation exposure.

There was something published in C&EN a while back (late 90s? early
2000s?) about the health and longevity of factory workers at benzene
facilities. After measuring exposures and throwing in the usual corrections
(smokers, etc), it turned out that the factory workers (who had demanded
the study to prove that they were being exploited by the companies) had
better health (fewer cancers) and longer lives than the general population.
It was STILL argued that the benzene was killing the workers. An avuncular
former participant in sci.chem commented that yes, it was killing them,
by making them live longer.

(Note: Benzene AIN'T good for you. That study showed that the factories
had lots of things in place to protect the workers from benzene exposures,
good health care, etc., etc., etc.)

Marvin

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Apr 6, 2006, 4:34:43 PM4/6/06
to
N:dlzc D:aol T:com (dlzc) wrote:
Sodium benzoate is derived from benzene, but it has
different chemical, physical, and pharmacologic properties.
It does not metabolize to benzene.

One of the common amino acids is phenylalanine. The word
"phenyl" designates a benzene ring. Phenylalanine is a
benzene derivative. It is in your most healthy diet. A few
people have a genetic disorder that requires htem to keep
this compound out of their diet as much as possible. It is
a very limited diet.

Christopher Specker

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Apr 6, 2006, 4:50:12 PM4/6/06
to
Marvin wrote:
>
>
> One of the common amino acids is phenylalanine. The word "phenyl"
> designates a benzene ring. Phenylalanine is a benzene derivative. It
> is in your most healthy diet. A few people have a genetic disorder that
> requires htem to keep this compound out of their diet as much as
> possible. It is a very limited diet.

This makes me wonder, do those same people have problems with tyrosine
as well? Food often has warning labels about phenylalanine, but I've
never seen warnings for tyrosine. The only difference is a hydroxyl group.

It's safe to say the presence of one small functional group can make a
HUGE difference in the toxicity or carcinogenicity of a substance.

The Sceptical Chymist

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Apr 6, 2006, 4:52:59 PM4/6/06
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<H...@nospam.nix> wrote in message
news:IHcZf.55852$F_3....@newssvr29.news.prodigy.net...

>
> "Borek" <m.bor...@delete.chembuddy.these.com.parts> wrote in message
>> Very good question. My take is that benzoates will be replaced, but in
>> 10-20 years it will become obvious that the cure was worse than the
>> illness.
>
> The illness can be pretty bad.
>
> But there might be alternative ways of sterilizing many food products
> which
> may prove adequate without using chemical antimicrobials, among them
> UV sterilization, ultrafiltration, flash heating etc.
>

Won't do any good. Benzoate conserves foods innoculated by the consumer
during use (eg each time you stick a spoon in your jar of mayonnaise).

Kostas Polyzonis

--
The strongest argument against Intelligent Design is the existence of its
proponents

--
To reply by private email, change invalid to gr


Jimchip

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Apr 6, 2006, 7:22:47 PM4/6/06
to

Maybe I can add 'a little' in order to clear 'a little' of this up. Benzene,
C6H6, is pretty well documented as a *leukemia* inducer. Like a lot of this
kind of data, the final 'decision' about it was based on the 'fact(s)' that
poor souls (my 'brothers and sisters') who worked with benzene itself in
high exposure environnments had a 'statistically higher' incidence of
leukemia.

I'm 'guessing' that "the skin cancer common between british chminey
sweepers" is associated with the polyaromatic hydrocarbons (PAH's) of which
benzo-a-pyrene and it's oxide are a notorious example of what happens when
the concept 'intercalator' means something to a human life.

I did read the whole thread, so far, so I will add that 'benzoic acid' and
many derivatives or 'relatives' should not be 'lumped-in' or 'grouped' (it's
not official "functional-group" that I'm thinking with that-----^ term) with
the 'bad' ones I described above. I'll mention one other compound that has
the 'benzoic acid' root as an example: PABA, para-aminobenzoic acid. It's
not 'bad' in any way (except maybe 'overdose' (which would include H20)).

'Us' humans get folic acid in our diet, hopefully, but PABA is a part of it.

--
"and one can 'play games' with PABA analogues in order to 'mess-up' those
*evil* bacteria (exception: not the ones that help me digest *my food*, of
course:) Note to myself: must keep 'friendly bacteria happy' by not 'lumping
them in).............. *DEATH* to evil bacteria!

Jimchip

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Apr 6, 2006, 7:32:37 PM4/6/06
to
On 2006-04-06, The Sceptical Chymist <poly...@otenet.invalid> wrote:
>
><H...@nospam.nix> wrote in message
> news:IHcZf.55852$F_3....@newssvr29.news.prodigy.net...
>>
>> "Borek" <m.bor...@delete.chembuddy.these.com.parts> wrote in message
>>> Very good question. My take is that benzoates will be replaced, but in
>>> 10-20 years it will become obvious that the cure was worse than the
>>> illness.
>>
>> The illness can be pretty bad.
>>
>> But there might be alternative ways of sterilizing many food products
>> which
>> may prove adequate without using chemical antimicrobials, among them
>> UV sterilization, ultrafiltration, flash heating etc.

Well, there are always (hopefully :) ) 'alternatives'...

> Won't do any good. Benzoate conserves foods innoculated by the consumer
> during use (eg each time you stick a spoon in your jar of mayonnaise).

I disagree with "Won't do any good". I agree with "Benzoate conserves
foods.." (antioxidants)

> Kostas Polyzonis

Jimchip

> --
> The strongest argument against Intelligent Design is the existence of its
> proponents

--
I like that sig :)----^

Ron Jones

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Apr 6, 2006, 7:51:50 PM4/6/06
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Marvin wrote:
> N:dlzc D:aol T:com (dlzc) wrote:
>>
> Sodium benzoate is derived from benzene, but it has
> different chemical, physical, and pharmacologic properties.
> It does not metabolize to benzene.

Really!?! I would have started from toluene. Benzoic acid has 7 carbon
atoms not 6, if you must start from a hydrocarbon then oxidation (with
permanganate) of toluene is the way to go. It's easily excreated - which is
why the exposure level of toluene is high - toluene is fairly rapidly
metabolized to benzoic acid, and is eliminated by the kidneys.


--
Ron Jones
Process Safety & Development, Alfa Aesar Avocado Lancaster UK
Don't repeat history, see unreported near misses in chemical lab/plant
at http://www.crhf.org.uk
Only two things are certain: The universe and human stupidity; and I'm
not certain about the universe. ~ Albert Einstein


dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

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Apr 6, 2006, 8:05:50 PM4/6/06
to
Dear Borek:

"Borek" <m.bor...@delete.chembuddy.these.com.parts> wrote in
message news:op.s7ld27mm26l578@borek...


> On Thu, 06 Apr 2006 15:17:44 +0200, dlzc1 D:cox
> <T:n...@nospam.com>> wrote:
>
>>>> was first time when "cancerogenity" appeared
>>>> (even if I have no idea how it was exactly
>>>> called then).
>>
>> "carcinogenicity" or "carcinogen"
>
> Thnx. Polish words are sometimes derived from
> English or from some common ancestor and
> usually spelling of English ones is obvious.
> Sometimes it is not :(

<QUOTE>
"The problem with defending the purity of the English language is
that the English language is as pure as a crib-house whore. It
not only borrows words from other languages; it has on occasion
chased other languages down dark alley-ways, clubbed them
unconscious and rifled their pockets for new vocabulary."
<END QUOTE>
-- James Nicoll

>> Notwithstanding my erroneous blanket statement,
>> what other chemicals can serve the same purpose
>> as benzoate?
>
> Very good question. My take is that benzoates will
> be replaced, but in 10-20 years it will become
> obvious that the cure was worse than the illness.

Thanks.

David A. Smith


dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

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Apr 6, 2006, 8:09:41 PM4/6/06
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Dear Madalch:

"Madalch" <tres...@gmail.com> wrote in message
news:1144345822.7...@e56g2000cwe.googlegroups.com...

The benzene is either present in the "syrup", formed when the
syrup and the water are mixed, or is formed in situ on the shelf
(or in transit). I didn't intend to imply any macroscopic
lifeform would "downconvert" it.

David A. Smith


dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

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Apr 6, 2006, 8:15:05 PM4/6/06
to
Dear HLS:

<H...@nospam.nix> wrote in message
news:IHcZf.55852$F_3....@newssvr29.news.prodigy.net...


>
> "Borek" <m.bor...@delete.chembuddy.these.com.parts> wrote in
> message
>> Very good question. My take is that benzoates will be
>> replaced, but in 10-20 years it will become obvious that
>> the cure was worse than the illness.
>
> The illness can be pretty bad.
>
> But there might be alternative ways of sterilizing many
> food products which may prove adequate without using
> chemical antimicrobials, among them UV sterilization,
> ultrafiltration, flash heating etc.
>
> It is my belief, perhaps incorrect, that a reasonably
> active reducing agent is needed to convert benzoate
> to benzene.

Would lime-softened water (pH of 10.4 or higher) be suitable to
act as a reducing agent? Some bottled water manufacturers don't
use reverse osmosis... and they bottle soda also.

> Omitting the ascorbic acid or other reducing agents, or
> deactivating natural reductants might be adequate
> to prevent the problem in some types of food products.

Ascorbic acid can act as a reducing agent? Not attacking, just
curious...

David A. Smith


luc...@sbcglobal.net

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Apr 6, 2006, 11:17:37 PM4/6/06
to

"Jimchip" <jim...@ifthisisavalidhostname.com> wrote in message
news:123b98l...@news.supernews.com...

> I disagree with "Won't do any good". I agree with "Benzoate conserves
> foods.." (antioxidants)
>


Benzoate is not an antioxidant. Antioxidants generally fall into 2 or 3
classes--sacrificial reductants that destroy hydroperoxides that form as the
result of autoxidation of organics (phosphites and thioethers are one
example of this class, being rather easily oxidized to phosphates and
sulfoxides/sulfones respectively) and radical traps that kill the radical
chain reactions that typically characterize autoxidation cycles (BHT, BHA
and various hindered amine oxides and nitroxyl radicals like TEMPO are in
this class, since the hindered radicals are good radical traps that don't
propagate radical chain reactions). Benzoate doesn't do either of these
reactions especially well. As far as I know, it is also not an
antimicrobial. My understanding is that its sole function is to inhibit
growth and multiplication of yeasts and perhaps also bacteria. That's how
the winemaking and beer brewing books that I read describe it, anyhow. As
someone else mentioned, its primary advantage is that it does continue to
control microbial growth long after production. I don't know of any other
simple compounds that do this well with low human toxicity, but I'm sure if
there's enough economic incentive, it will happen.

Several years ago, do you remember the benzene scare in some brand of French
snob-water (Evian, Perrier, I'm not sure which.) You would not believe the
time and money we went through to show this wasn't coming from the plastics
used to make the bottles, down to and including sub-ppm catalyst residues in
those bottles that had a remote chance to decomposing to give benzene.
Turned out their souce spring was contaminated, but the point is, an
unfortunate coincidence like that is all that needs to happen to get people
to panic over the unlikely but plausible conversion of some ingredient like
benzoate into a carcinogen like benzene. If you think about the industrial
inhalation studies with benzene (8+ hours per day for up to 30 years
breathing ~grams of benzene per hour, causing a relatively small increase in
the incidence of leukemia), it's pretty ridiculous to worry about the tiny
amount of benzene that might come from sub-percent levels of benzoate
undergoing a minor side-reaction to give sub-percent yields of benzene.

By the way, in response to the comment about needing a strong reductant to
reduce benzoate to benzene, that's not correct. It's probably
thermodynamically favorable with just about any reductant--the release of
CO2 gas would drive the equilibrium. The kinetics of the reaction is the
issue, and a sufficiently reactive catalyst will do the reaction with some
pretty mild reductants. For example, if you compared the heats of
formation, you might find that even a very mild reductant like formic acid
is a strong enough reductant thermodynamically. The point is the kinetics,
and the presence of a catalyst for the reaction, is what matters. I suspect
that some biological system is a likely culprit--i.e., some bacterium that
is for some reason able to metabolize benzoate to benzene. I have the
impression that, often reactions that require C-C bond cleavage under mild
and selective conditions like this are done most effectively by biological
systems.

Eric Lucas


luc...@sbcglobal.net

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Apr 6, 2006, 11:31:25 PM4/6/06
to
It just occurred to me that decarboxylation of benzoate to benzene is not a
redox reaction. Write a balanced equation:

C6H5CO2- + H+ --> C6H6 + CO2

No reductant needed, just an acid. Mechanism could go something like this:
protonate ipso carbon, and decarboxylate. Having said that, I don't think
I'm familiar with any aromatic decarboxylations like this as synthetically
useful reactions (even with very electron rich arenes that protonate easily
on C). However, that doesn't mean it can't occur as a small side reaction
over a long shelf storage life, to generate low levels of benzene--and all
it requires is the presence of a sufficient concentration of a general acid
catalyst. Since biological (read: food) systems are heavily buffered with
CO2/HCO3-, phosphate and other buffers, (and in fact, fruit juices and pops
even have a pretty high concentrations of specific acids that can act as
catalysts, considering their pH often runs as low as 2 - 3), this provides a
high concentration of a variety of general acid catalysts that could induce
this reaction.

Still, the potential exposure in this case is orders of magnitude lower than
exposure levels in occupational benzene leukemia studies.

Eric Lucas
<luc...@sbcglobal.net> wrote in message
news:lRkZf.8977$4L1....@newssvr11.news.prodigy.com...

Madalch

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Apr 7, 2006, 3:41:27 AM4/7/06
to
> I don't think I'm familiar with any aromatic decarboxylations like this
> as synthetically useful reactions.

Carboxylic acids can generally be decarboxylated to give hydrocarbons
by strong heating with calcium oxide.

> However, that doesn't mean it can't occur as a small side reaction
> over a long shelf storage life,

It also doesn't mean that it does.

|||new...@nezumi.demon.co.uk

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Apr 7, 2006, 4:39:49 AM4/7/06
to
>Several years ago, do you remember the benzene scare in some brand of French
>snob-water (Evian, Perrier, I'm not sure which.)

Perrier, but at least their product was naturally contaminated and they
were very responsible about fixing it.

OTOH Dasani managed to turn potable London tapwater into something that
was not fit for human consumption by adding artificial mineral salts
due to formation of bromate impurities in their designer brand product-
leading to an ignominious withdrawal from the Euoprean market. The
water board quality control labs could not believe their luck when they
analysed it.

> You would not believe the
>time and money we went through to show this wasn't coming from the plastics
>used to make the bottles, down to and including sub-ppm catalyst residues in
>those bottles that had a remote chance to decomposing to give benzene.
>Turned out their souce spring was contaminated, but the point is, an
>unfortunate coincidence like that is all that needs to happen to get people
>to panic over the unlikely but plausible conversion of some ingredient like
>benzoate into a carcinogen like benzene. If you think about the industrial
>inhalation studies with benzene (8+ hours per day for up to 30 years
>breathing ~grams of benzene per hour, causing a relatively small increase in
>the incidence of leukemia), it's pretty ridiculous to worry about the tiny
>amount of benzene that might come from sub-percent levels of benzoate
>undergoing a minor side-reaction to give sub-percent yields of benzene.

However, the measured benzene concentrations in a few products were way
too high compared to drinking water standards - around 30ppb found in
the worst (interesting clue that they are mostly low calorie no added
sugar fruit juice based things). The WHO approved level in drinking
water is 10ppb. Most soft drinks tested clean but some showed slow
conversion of benzoate into benzene - mechanism as yet unclear. I would
not want 30ppb benzene in childrens soft drinks YMMV.

Reasonably balanced report on the BBC UK website.

http://news.bbc.co.uk/1/hi/health/4864226.stm

Seems drinks get worse close to their sell-by date so it looks like a
slow in-vitro reaction that is catalysed by one or more of the
additives common to the drinks where detectable levels of benzene have
been found. Acidic fruit juices with a lot of citric, tartaric,
ascorbic acids and some non-sugar sweetener perhaps.

Regards,
Martin Brown

Jimchip

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Apr 7, 2006, 11:34:34 AM4/7/06
to
On 2006-04-07, <luc...@sbcglobal.net> <luc...@sbcglobal.net> wrote:
>
> "Jimchip" <jim...@ifthisisavalidhostname.com> wrote in message
> news:123b98l...@news.supernews.com...
>
>> I disagree with "Won't do any good". I agree with "Benzoate conserves
>> foods.." (antioxidants)
--------------^^^^^^^^^^^^^

>
>
> Benzoate is not an antioxidant.

OK [sorta] but my message was to the OP [and, of course, any other
'brain-damaged-idiot' who still writes on USENET] but I will agree that *my*
message was "..., brutish, and short".

The little dressing up *I* just did ^UP THERE^ was to show that
'(antioxidants)' was (and is and will be what I call a "parenthetical".)

I was *not* claiming that "Benzoate conserves foods" = 'antioxidants', I was
merely mentioning, "parenthetically" another 'key-word' that could be
helpful. (((((these stupid symbols are for 'some-thing' aren't they?)))))


> Antioxidants generally fall into 2 or 3
> classes--sacrificial reductants that destroy hydroperoxides that form as the
> result of autoxidation of organics (phosphites and thioethers are one
> example of this class, being rather easily oxidized to phosphates and
> sulfoxides/sulfones respectively) and radical traps that kill the radical
> chain reactions that typically characterize autoxidation cycles (BHT, BHA
> and various hindered amine oxides and nitroxyl radicals like TEMPO are in
> this class, since the hindered radicals are good radical traps that don't
> propagate radical chain reactions). Benzoate doesn't do either of these
> reactions especially well. As far as I know, it is also not an
> antimicrobial. My understanding is that its sole function is to inhibit
> growth and multiplication of yeasts and perhaps also bacteria. That's how
> the winemaking and beer brewing books that I read describe it, anyhow. As
> someone else mentioned, its primary advantage is that it does continue to
> control microbial growth long after production. I don't know of any other
> simple compounds that do this well with low human toxicity, but I'm sure if
> there's enough economic incentive, it will happen.

Frankly, (although I will read 'iT', I have not,) It looks like a
'copy-paste-job' [You know 'that one' 'up there' and 'below'- just post the
ref...)

Jimchip

--
"Thank you, 'Eric' for your contribution to my electron-burning
"hyper-hypothesis" that people don't pay attention. (I'm not saying you
can't 'THIMK', mind you:)

Marvin

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Apr 7, 2006, 11:50:32 AM4/7/06
to
N:dlzc D:aol T:com (dlzc) wrote:
<snip>

>
> Would lime-softened water (pH of 10.4 or higher) be suitable to
> act as a reducing agent? Some bottled water manufacturers don't
> use reverse osmosis... and they bottle soda also.
No. And anyone who is that concerned about his health
shouldn't be drinking sodas anyway.

Chris Cooksey

unread,
Apr 7, 2006, 12:06:27 PM4/7/06
to
In article <123d2i4...@corp.supernews.com>, Marvin
<phys...@cloud9.net> writes
Seems to me that if you reduce benzoate you get benzyl alcohol then
toluene. In order to get benzene, decarboxylation is required. May
be enzymes will do that.

Anyway, more health scares from the UK:

http://www.food.gov.uk/enforcement/alerts/2006/apr/candcbenzene

--
Chris Cooksey

Jimchip

unread,
Apr 7, 2006, 3:42:00 PM4/7/06
to
On 2006-04-07, <luc...@sbcglobal.net> <luc...@sbcglobal.net> wrote:
> It just occurred to me that decarboxylation of benzoate to benzene is not a
> redox reaction. Write a balanced equation:
>
> C6H5CO2- + H+ --> C6H6 + CO2

Think of a Grignard synthesis of benzoic acid:

C6H5MgX + CO2---> --->
H+

> No reductant needed, just an acid. Mechanism could go something like this:
> protonate ipso carbon, and decarboxylate. Having said that, I don't think
> I'm familiar with any aromatic decarboxylations like this as synthetically
> useful reactions (even with very electron rich arenes that protonate easily
> on C). However, that doesn't mean it can't occur as a small side reaction
> over a long shelf storage life, to generate low levels of benzene--and all
> it requires is the presence of a sufficient concentration of a general acid
> catalyst. Since biological (read: food) systems are heavily buffered with
> CO2/HCO3-, phosphate and other buffers, (and in fact, fruit juices and pops
> even have a pretty high concentrations of specific acids that can act as
> catalysts, considering their pH often runs as low as 2 - 3), this provides a
> high concentration of a variety of general acid catalysts that could induce
> this reaction.
>
> Still, the potential exposure in this case is orders of magnitude lower than
> exposure levels in occupational benzene leukemia studies.
>
> Eric Lucas

[snippage]

--
Chemistry can be fun.
I fell on my head as a child and, as it turns out, Chemistry is the only
thing I could learn how to do.
(and I *hated* 'piano lessons' but it made me a better typist :)

H...@nospam.nix

unread,
Apr 7, 2006, 4:49:36 PM4/7/06
to
. As far as I know, it is also not an
> antimicrobial. My understanding is that its sole function is to inhibit
> growth and multiplication of yeasts and perhaps also bacteria.

Well what the fuck do you think an antimicrobial is limited to doing?

It inhibits a number of different microbes, but only at decreased pH.


H...@nospam.nix

unread,
Apr 7, 2006, 4:53:35 PM4/7/06
to

"N:dlzc D:aol T:com (dlzc)" <N: dlzc1 D:cox T:n...@nospam.com> wrote in
message news:7aiZf.12783$kT4.6417@fed1read02...

> Would lime-softened water (pH of 10.4 or higher) be suitable to
> act as a reducing agent? Some bottled water manufacturers don't
> use reverse osmosis... and they bottle soda also.

I would not think that high pH water would function this way. Temperature
and increased pH can however promote decarboxylation under some
conditions.

> > Omitting the ascorbic acid or other reducing agents, or
> > deactivating natural reductants might be adequate
> > to prevent the problem in some types of food products.
>
> Ascorbic acid can act as a reducing agent? Not attacking, just
> curious...

Ascorbic acid acts as a reducing agent. Very much so. And the
conversion of benzoate or benzoic acid in the presence of ascorbic
acid is documented.

H...@nospam.nix

unread,
Apr 7, 2006, 5:07:42 PM4/7/06
to

"Jimchip" <jim...@ifthisisavalidhostname.com> wrote in message
news:123b98l...@news.supernews.com...
> I disagree with "Won't do any good". I agree with "Benzoate conserves
> foods.." (antioxidants)
¨
Benzoic acid is recognized as as preservative under certain conditions.
Primarily, it is active at decreased pH values, around 3.5. It is active
against
a number of microorganisms, BUT realize that it is also used as a
biodegradation
standard in some of the OECD tests. It should be reproducibly 100%
biodegradable
in 28 day assays using natural microorganisms found in seawater.

Propionate is normally used in baking as a mold retarder, etc. It is
active at a much wider pH range, but is not normally used to supplant
benzoic acid or benzoate totally.

You cannot protect an idiot. Whatever food you package, you cannot
prevent misuse and secondary contamination. What you must do is present
a safe product to the end user. He can kill himself with it if he wishes.

I found references to the conversion of benzoic acid or benzoate to benzene
when in contact with ascorbic acid (Vitamin C). Whether you like the
chemistry
or not (and I am no expert in this area), someone seems to have found this
to
happen.

Simple reduction would probably lead to toluene, as another poster has
suggested.

Decarboxylation might well lead to benzene. And then, there might
be other paths to leukemia.

I don't intend to stay up nights and worry about it.


hanson

unread,
Apr 7, 2006, 5:58:39 PM4/7/06
to
"Jimchip" <jim...@ifthisisavalidhostname.com> wrote in message
news:123dg48...@news.supernews.com...

> Eric <luc...@sbcglobal.net> <luc...@sbcglobal.net> wrote:
>> It just occurred to me that decarboxylation of benzoate to benzene
>> is not a redox reaction. Write a balanced equation: [1]

>> C6H5CO2- + H+ --> C6H6 + CO2
>
[Jichimp]

> Think of a Grignard synthesis of benzoic acid:
> C6H5MgX + CO2---> ---> H+
> Chemistry can be fun.
> I fell on my head as a child and, as it turns out,
> Chemistry is the only thing I could learn how to do.
> (and I *hated* 'piano lessons' but it made me a better typist :)
>
[hanson]
.... ahahaha... yeah, yeah, jim, you are right on many counts
especially about line 4... ahahaha...
>
Eric, afa your comments [1] and [2], you are right and there
are preparative methods for decarboxilations for aromatics,
simply by "cooking" them in 93% H2SO4 or in conc. H3PO4.
IR deCO2ing Pyrazine tetra carboxylic acid into pyrazine
mono carboxylic acid splitting off 3 CO2/mole in a foaming
2 hrs process and the yield was surprisingly good. There is
no discernable reason that this method should not work
for/on C6H6COOH. Naturally for economic reasons it will
never be carried out, except for high school lab demos.

On a related enviro note since so many posters here worry
about the POTENTIAL dangers of benzene first instead of
the issue at hand, ... but most of them being unholy greenies, ...
and certainly being the ones that don't even know how
benzene smells... ahahahaha....

... I though do agree with them that a constant, long term,
8 hrs/day exposure to C6H6 fumes may cause health issues.
But so does every other aromatic VOC in the long run. But,
their green paranoia is severely overrated because anyone
who forces himself to inhale/stay at a place where there are
these pungent, acrid, cough invoking and migraine producing
fumes of aromatics present, is even more stupid then are the
green shits who try to save them via/with their permit charges,
user fees and enviro surtaxes.... but OTOH do make sure that
the chemical stays available for use... so that these illbegotten
phony green shits can take advantage and make money off
the situation. Case in point:

Long ago, when I visited LA quite often I saw an enviro warning
poster at the gas pump, issued by order of the local Aeolian
enviro agency, signed by chief green fart , named Flatu Lenz,
that said:
=== "This brand of gasoline contains benzene as an octane
enhancing additive from which you may POTENTIALLY get
cancer if you sit 24/7 for 75 (!) seventy-five years next to the
running gas pump nozzle." ===

.... ahahaha... No wonder Eric Gisin said in his memorable post
in news:d8j4d...@enews1.newsguy.com... that
********** "Fucking greens should be shot...." *************
Thanks for the laughs, guys.... ahahahaha....
ahahaha... ahahanson
>
[Eric]


>> No reductant needed, just an acid. Mechanism could go something like this:
>> protonate ipso carbon, and decarboxylate. Having said that, I don't think

>> I'm familiar with any aromatic decarboxylations like this as synthetically [2]

luc...@sbcglobal.net

unread,
Apr 7, 2006, 7:48:05 PM4/7/06
to

<H...@nospam.nix> wrote in message
news:AfAZf.56094$F_3....@newssvr29.news.prodigy.net...


The usual context in which I use the term "antimicrobial" is that it kills
microbes. However, that may be an unnecessarily narrow definition. Mea
culpa.

Eric Lucas


Marvin

unread,
Apr 8, 2006, 11:23:43 AM4/8/06
to
> How far does it go? To benzene? Under physiological
conditions? Under conditions in a soda can?

dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

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Apr 8, 2006, 3:44:17 PM4/8/06
to
Dear Marvin:

"Marvin" <phys...@cloud9.net> wrote in message
news:123flbr...@corp.supernews.com...


...
>> Ascorbic acid acts as a reducing agent. Very much
>> so. And the conversion of benzoate or benzoic acid
>> in the presence of ascorbic acid is documented.
>>
> How far does it go? To benzene? Under
> physiological conditions? Under conditions in a soda
> can?

Very low pH. Presence of light (helps). You find neither in a
body.

http://www.cfsan.fda.gov/~dms/benzltr.html

Plenty more with Google.

David A. Smith


Marvin

unread,
Apr 9, 2006, 11:18:21 AM4/9/06
to
The letter confirms my belief that many people worry about
things that matter less than other things they can do
something about. In the case of soft drinks, the national
problem is the obesity that is caused to a significant
extent by the empty calories in soft drinks and other
suger-rich foods. Those who switch to artificial sweeteners
are then given alarmist warnings about those substances.

I was diagnosed with type 2 diabetes two years ago. I
quickly lost 25 pounds and have kept my weight down, mainly
by eating sugar-free and reduced sugar foods. I check my
blood sugar levels, and they are rarely high. My A1c levels
are well into the normal range. And so is my cholesterol.
My biggest medical problem so far this year was having too
much wax in my ears. I don't feel deprived of foods I like.

dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

unread,
Apr 9, 2006, 1:11:25 PM4/9/06
to
Dear Marvin:

"Marvin" <phys...@cloud9.net> wrote in message

news:123i9dv...@corp.supernews.com...


> N:dlzc D:aol T:com (dlzc) wrote:

...


>>>How far does it go? To benzene? Under
>>>physiological conditions? Under conditions in a soda
>>>can?
>>
>> Very low pH. Presence of light (helps). You find
>> neither in a body.
>>
>> http://www.cfsan.fda.gov/~dms/benzltr.html
>>
>> Plenty more with Google.
>

> The letter confirms my belief that many people worry
> about things that matter less than other things they
> can do something about.

Everyone wants a bad guy. No one wants to believe that if there
is a bady guy, it is themselves.

> In the case of soft drinks, the national problem is the
> obesity that is caused to a
> significant extent by the empty calories in soft
> drinks and other suger-rich foods. Those who
> switch to artificial sweeteners are then given
> alarmist warnings about those substances.

There are competing brands. There is a driver to the "alarmist
warnings", just as there is a driver to "diet colas will help you
to lose weight".

> I was diagnosed with type 2 diabetes two years
> ago. I quickly lost 25 pounds and have kept my
> weight down, mainly by eating sugar-free and
> reduced sugar foods. I check my blood sugar
> levels, and they are rarely high. My A1c levels are well into
> the normal range. And so is my
> cholesterol. My biggest medical problem so far
> this year was having too much wax in my ears.
> I don't feel deprived of foods I like.

"All things in moderation." Sounds like good advice.

David A. Smith


Simon Dobbs

unread,
Apr 9, 2006, 1:13:06 PM4/9/06
to
On Fri, 7 Apr 2006 21:53:35 +0100, H...@nospam.nix wrote
(in article <jjAZf.56096$F_3....@newssvr29.news.prodigy.net>):

> Ascorbic acid acts as a reducing agent. Very much so. And the
> conversion of benzoate or benzoic acid in the presence of ascorbic
> acid is documented.

it's well documented as oxidative decarboxylation of a carboxylic acid which
is, surprise surprise, an oxidative process. Biochemically NADH is the
reducing agent usually, but there is no reason why oxidised vitamin c in a
drinks can can't oxidise benzoic acid., itself becoming reduced. The
prescence of oxidised vitamin c in an aqueous envirnment should come as no
surprise.

Simon Dobbs

unread,
Apr 9, 2006, 4:14:16 PM4/9/06
to
On Sun, 9 Apr 2006 18:13:06 +0100, Simon Dobbs wrote
(in article <0001HW.C05EFF32...@news.demon.co.uk>):

> NADH is the
> reducing agent

of course, that should read NAD+ is the oxidising agent.

Bruce Sinclair

unread,
Apr 9, 2006, 7:24:03 PM4/9/06
to
In article <Seb_f.135$AB3.58@fed1read02>, "N:dlzc D:aol T:com \(dlzc\)" <N: dlzc1 D:cox T:n...@nospam.com> wrote:
(snip)

>
>"All things in moderation." Sounds like good advice.

I prefer Arnold Beckman's version of this ...
"Practice moderation in all things - including moderation (there's nothing
wrong with a little excess once in a while)"

I reckon what he's saying is, worrying about what you eat will likely do you
more harm than what you eat - I certainly believe that. :)


Bruce

----------------------------------------
I believe you find life such a problem because you think there are the good
people and the bad people. You're wrong, of course. There are, always and
only, the bad people, but some of them are on opposite sides.

Lord Vetinari in Guards ! Guards ! - Terry Pratchett

Caution ===== followups may have been changed to relevant groups
(if there were any)

Bruce Sinclair

unread,
Apr 9, 2006, 7:25:12 PM4/9/06
to
In article <s1iZf.12781$kT4.6554@fed1read02>, "N:dlzc D:aol T:com \(dlzc\)" <N: dlzc1 D:cox T:n...@nospam.com> wrote:

(snip)

><QUOTE>
>"The problem with defending the purity of the English language is
>that the English language is as pure as a crib-house whore. It
>not only borrows words from other languages; it has on occasion
>chased other languages down dark alley-ways, clubbed them
>unconscious and rifled their pockets for new vocabulary."
><END QUOTE>

Another fine terry pratchett quote IIRC :)

Steven

unread,
Apr 10, 2006, 9:10:08 AM4/10/06
to
Hey, who the hell told you that benzene is formed from benzoate, when
used as preservative????? It seems that you do not understand the
meaning of benzoate.... Benzene is not formed from benzoate when the
latter is used as a preservative. When there are reports about benzene
found in foods, the benzene content has other sources, for example
contamination through machinery contact, and lubicants, or when the
food is taken near from busy streets or areas with petrochemical
activity....

Simon Dobbs

unread,
Apr 10, 2006, 9:54:15 AM4/10/06
to
On Mon, 10 Apr 2006 14:10:08 +0100, Steven wrote
(in article <1144674608.6...@u72g2000cwu.googlegroups.com>):

you haven't been following the news

> FDA re-opens probe into benzene contamination of soft drinks
>
> By Chris Mercer
>
>  
>
>
>
>
>  
> Get the latest Market Reports on

>  


>
> 2/15/2006 - US food safety authorities have re-opened an investigation closed

> 15 years ago into soft drinks contaminated with cancer-causing chemical
> benzene, following evidence the industry has failed to sort out the problem.
>
> A chemist at the Food And Drug Administration (FDA) said testing in recent
> weeks had revealed some soft drinks contaminated with benzene at levels above

> the legal limit for water set by the US and Europe.
> Benzene is listed as a poisonous chemical shown to increase the risk of
> leukaemia and other cancers.
> The FDA was originally alerted in 1990 to the problem of benzene in soft
> drinks triggered by the preservative sodium benzoate. It never made the
> findings public, but came to an arrangement with the US soft drinks
> association that the industry would łget the word out˛.
> But in recent months, internal documents and private tests have begun to
> surface, supported by claims from a former chemist for Cadbury Schweppes, who

> is now keen to blow the whistle on the health risk involved. He and a US
> lawyer commissioned new tests that have now prompted the FDA to re-open the
> case.
> These independent tests, performed by a laboratory in New York, found benzene

> levels in a couple of soft drinks two-and-a-half-times and five times above
> the World Health Organisation limit for drinking water (10 parts per
billion).
> The FDA now confirms it has found a similar problem in its own follow-up
> testing. łThere were a few isolated products that have elevated levels. We
> certainly want to make sure there is some reformulation,˛ said an FDA
chemist.
> The problem is caused by two common ingredients ­ sodium benzoate and
> ascorbic acid (vitamin C) ­ which can react together to cause benzene
> formation. It is considered completely separate from other outbreaks of
> benzene contamination due to faulty packaging in the 1990s.
> The two ingredients are still used together in a wide range of soft drinks
> across the world.
> The FDA was first alerted to the problem in December 1990 by Cadbury
> Schweppes and Australian drinks group Koala Springs, according to an internal

> FDA memo.
> This prompted FDA testing that led the US Department of Health and Human
> Services to report, again in an internal memo: łBenzene formation occurs at
> part per billion (ppb) levels in some food formulations containing sodium
> benzoate and ascorbic acid [vitamin C].˛
> These findings were discussed in a meeting between the FDA and National Soft
> Drinks Association (NSDA), representing the likes of Coca-Cola, PepsiCo and
> Cadbury Schweppes. The internal minutes from this meeting report that the
> companies, through the NSDA, łexpressed concern about the presence of benzene

> traces in their products and the potential for adverse publicity associated
> with this problem˛.
> But Greg Diachenko, an FDA chemist who helped to co-ordinate the FDA testing
> for benzene in 1990/91 and who took part in negotiations with the industry,
> said: łSoft drinks manufacturers told us [at the time] that they would get
> the word out and they were reformulating.˛
> Legal action was not taken, he said, because the industry was already
> reformulating. This, he added, meant that any risk to consumers would be very

> short-term because risk analysis in the US works on the basis of lifetime
> exposure to a substance.
> The FDA did more tests in the US in 1993 and found no problem. But, added
> Diachenko: łIt is probable and likely that there were some people who did not

> get the message or that it was lost in the course of time.˛
> Any soft drink companies founded since 1993, for example, could be outside of

> the loop and not know about the potential Śfixes'.
> Plus, the FDA, as a US authority, only checked drinks available in the US.
> Diachenko said he was not sure how many other regulatory authorities had been

> told about the potential for benzene formation from sodium benzoate and
> ascorbic acid.
> An article flagging up the problem was published in the public journal, the
> Journal of Agricultural and Food Chemistry, in 1993.
> According to Diachenko at the FDA, if authorities outside the US had not seen

> the information they might not know, and that could mean more soft drinks
> containing benzene in their areas.
> More than 1,500 soft drink products containing sodium benzoate and ascorbic
> acid or citric acid have been launched across Europe, Latin America and North

> America since January 2002.
> Glen Lawrence, another chemist who conducted benzene testing for the FDA back

> in 1990-1991 and a co-author of the 1993 journal article, has also confirmed
> to BeverageDaily.com that sodium benzoate and ascorbic acid do react to form
> benzene in soft drinks.
> His study showed that ascorbic acid initially reacted with metals, such as
> iron or copper, found in the water to create Śfree radical' particles known
> as hydroxyl radicals.
> Sodium benzoate, meanwhile, breaks down into benzoic acid when placed in
> acidic conditions, such as in a soft drink.
> The hydroxyl radical attacks the benzoic acid, removing the carbon dioxide
> from it and leaving benzene in its wake. Lawrence's study said this reaction
> could take place łunder conditions prevalent in many foods and beverages˛.

Bruce Sinclair

unread,
Apr 10, 2006, 7:06:14 PM4/10/06
to
In article <0001HW.C0602217...@news.demon.co.uk>, simon...@froglet.net wrote:
>On Mon, 10 Apr 2006 14:10:08 +0100, Steven wrote
>(in article <1144674608.6...@u72g2000cwu.googlegroups.com>):
>
>> Hey, who the hell told you that benzene is formed from benzoate, when
>> used as preservative????? It seems that you do not understand the
>> meaning of benzoate.... Benzene is not formed from benzoate when the
>> latter is used as a preservative. When there are reports about benzene
>> found in foods, the benzene content has other sources, for example
>> contamination through machinery contact, and lubicants, or when the
>> food is taken near from busy streets or areas with petrochemical
>> activity....
>you haven't been following the news
>> FDA re-opens probe into benzene contamination of soft drinks

If you are drinking soft drinks then a tiny amount of benzene should be the
least of your worries :)

dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

unread,
Apr 10, 2006, 9:54:52 PM4/10/06
to
Dear Steven:

"Steven" <ste...@chemie.fu-berlin.de> wrote in message
news:1144674608.6...@u72g2000cwu.googlegroups.com...


> Hey, who the hell told you that benzene is formed from
> benzoate, when used as preservative????? It seems
> that you do not understand the meaning of benzoate....

Benzene is known to be formed from benzoate in the presence of
(at least) ascorbic acid.

The level of benzene increases in the drink over time.

The drink may be initially contaminated, but there is more to it.

David A. Smith


Steven

unread,
Apr 11, 2006, 7:00:10 AM4/11/06
to

N:dlzc D:aol T:com (dlzc) wrote:

> Benzene is known to be formed from benzoate in the presence of
> (at least) ascorbic acid.
>
> The level of benzene increases in the drink over time.
>
> The drink may be initially contaminated, but there is more to it.
>
> David A. Smith

Hi David,

Thanks for the hint. Intersting to read about this. But to be honest,
the amount of benzene formed is at a level, where you can't consider
this to be a serious problem. Benzene content in the environment in air
through traffic etc. is very probably more serious. About the formation
of benzene from benzoate in the presence of ascorbic acid, the only
possible pathway of formation is a radical process. But Ascorbic acid
is probably not the initiator, but only the mediator of the radical
process. Thus, it may be possible that the initiator for radicals may
be light (conditions of storage) or other radical formation processes.
Ascorbic acid itself serves also as a radical scaveger, not a radical
initiator. That's just to note....

Steven

unread,
Apr 11, 2006, 7:22:46 AM4/11/06
to
Just for an additional note: benzoate is not used as an antioxidant (it
can't be used as this anymway), but it has an (killing) effect on
microorganisms, and thus it is used as a preservative (but not as a
preservative with antioxidant activity).

Message has been deleted

Steven

unread,
Apr 11, 2006, 8:04:30 AM4/11/06
to
Also you need to consider the conditions when this process occurs. You
need light and low pH values (below pH 3.5). In normal cases soft
drinks do not have such a low pH value, but of course there are many
ingredients inside soft drinks, which are acids, e.g. huge amounts of
phosphoric acids or even ascorbic acid. But these acids are not put
inside in pure form, mainly as a salt (ascorbic acid as sodium
ascorbate) or as a buffered solution. A soft drink may have a pH below
7, but not below pH 5 (in contrast to soda drinks, which are more
alkaline, pH > 7). When you drink your soft drink, it is mixed with the
hydrochloric acid present in your stomach (there you may find pH values

even below 2 in some instances). There might occur radical
decomposition processes inside the bottle even above pH 3.5 (according
to Nernst' law), but the extent how this might happen is very low.....
Normaly, and here I speak for myself, I do not drink 5-year-old soft
drinks, which were stored in sunlight. I guess you will vomit those
either..... Also: there is printed a durability date (can be used
until....... or: Do not use
after.......).

dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

unread,
Apr 11, 2006, 9:15:57 AM4/11/06
to
Dear Steven:

"Steven" <ste...@chemie.fu-berlin.de> wrote in message

news:1144757070....@z34g2000cwc.googlegroups.com...


> Also you need to consider the conditions when this
> process occurs. You need light and low pH values
> (below pH 3.5). In normal cases soft drinks do not
> have such a low pH value, but of course there are
> many ingredients inside soft drinks, which are acids,
> e.g. huge amounts of phosphoric acids or even
> ascorbic acid. But these acids are not put inside in
> pure form, mainly as a salt (ascorbic acid as sodium
> ascorbate) or as a buffered solution. A soft drink may
> have a pH below 7, but not below pH 5 (in contrast to
> soda drinks, which are more alkaline, pH > 7).

Carbonic acid (CO2 "dissolved" in water) can drive the pH down to
about 4. Plenty of that in soda, even fruit soda.

> When you drink your soft drink, it is mixed with the
> hydrochloric acid present in your stomach (there you
> may find pH values even below 2 in some instances).
> There might occur radical decomposition processes
> inside the bottle even above pH 3.5 (according to
> Nernst' law), but the extent how this might happen is
> very low.....
> Normaly, and here I speak for myself, I do not drink
> 5-year-old soft drinks, which were stored in sunlight.

How would you know where they were stored? The age, sure.

> I guess you will vomit those either..... Also: there is
> printed a durability date (can be used until....... or:
> Do not use after.......).

Thanks for the response. My real concern was is there a handy
substitute to replace benzoate? Those manufacturers that added
it to their products are now going to be scrambling for options.
Decreasing shelf life is probably not an option, even if they
could have sterilized their product beforehand.

Put on refrigerated racks in a health food store is not always
the beginning one would seek for one's products. It is more
commonly the end.

David A. Smith


Art Ickles

unread,
Apr 12, 2006, 9:42:32 AM4/12/06
to
N:dlzc D:aol T:com (dlzc) wrote:

> > "Steven" <ste...@chemie.fu-berlin.de> wrote in message
> >

> > Hey, who the hell told you that benzene is formed from
> > benzoate, when used as preservative????? It seems
> > that you do not understand the meaning of benzoate....
>

> Benzene is known to be formed from benzoate in the presence of
> (at least) ascorbic acid.

So far, the earliest work on soda samples that I can find appears to be
due to a group of radicals in Brooklyn, NY.

Gardner LK, Lawrence GD
Benzene Production from Decarboxylation of Benzoic Acid in the Presence
of Ascorbic Acid and a Transition Metal Catalyst.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 41 (5): 693-695 MAY 1993
KeyWords: RADICALS
Address: LONG ISL UNIV, DEPT CHEM, BROOKLYN, NY 11201 USA

Maybe even radical communists, although their work has been cited by others,
including:

Scotter, MJ; Castle, L
Chemical interactions between additives in foodstuffs: a review
FOOD ADDITIVES AND CONTAMINANTS, 21 (2): 93-124 FEB 2004

Adams, JB
Food additive-additive interactions involving sulphur dioxide and ascorbic
and nitrous acids: A review
FOOD CHEMISTRY, 59 (3): 401-409 JUL 1997

Aruoma, OI
Assessment of potential prooxidant and antioxidant actions
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 73 (12): 1617-1625 DEC 1996

Muller, CJ; Fugelsang, KC
Antioxidants in Food - Another Look
AMERICAN JOURNAL OF CLINICAL NUTRITION, 60 (3): 456-457 SEP 1994


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Bob M

unread,
Apr 12, 2006, 4:22:49 PM4/12/06
to
Look at site www.molab.co.nz
There is something on the topic.

Bob M

Steven

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Apr 12, 2006, 5:32:02 PM4/12/06
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N:dlzc D:aol T:com (dlzc) schrieb:

> Carbonic acid (CO2 "dissolved" in water) can drive the pH down to
> about 4. Plenty of that in soda, even fruit soda.

Yes, normally you are right with that, but then it is not a "soda" in
the meaning of the definition of soda. "Soda" is the short cut for
sodium (bi)carbonate, the bicarbonte is mainly present in the region
between 6,8 to 8,0, that's slightly alkaline. The higher the pH, the
more the bicarbonate ion is deprotonated to yield carbonate anion
(present in solutions pH > 8). The content of dissolved CO2 is not
equal to "soda", that means that a drink with a high CO2 content does
not automatically mean that it is soda drink. A soda drink always taste
a little bit like a soap, thus it is slightly alkaline. The content of
dissolved carbon dioxide in water is the highest in slightly acid
medium, that's right. Also consider that there is a difference between
physically dissolved carbon dioxide and chemical bound (the "real"
carbonic acid). There is always only a very small content of real
(chemical) carbonic acid, the most of the carbon dioxide is only
disolved physically, just an intermediate status between the
unprotonated and protonated from of carbon dioxide (pressure
dependend). And if you have a soft drink where a lot of carbon dioxide
was put in with pressure, and there is a pH below 6, then this is not a
soda drink - it is just a soft drink, with a high content of physical
bound carbon dioxide. This is often confused by people, because the
content of carbon dioxide in a drink does not automatically mean that
this is a soda. But I also know how exact definitions change with time
to time by using the words in everyday context, and what the normal
people understand with soda or carbonic acid is far away from the
definitions in most cases.

> > Normaly, and here I speak for myself, I do not drink
> > 5-year-old soft drinks, which were stored in sunlight.
>
> How would you know where they were stored? The age, sure.
>
> > I guess you will vomit those either..... Also: there is
> > printed a durability date (can be used until....... or:
> > Do not use after.......).
>
> Thanks for the response. My real concern was is there a handy
> substitute to replace benzoate? Those manufacturers that added
> it to their products are now going to be scrambling for options.
> Decreasing shelf life is probably not an option, even if they
> could have sterilized their product beforehand.

Why are you concerned on the benzoate? The amount of benzene formed by
decarboxylation is very low, and you have much more concentrations of
carcinogens in all your environment. Even you have benzoate in your
body, without drinking any soft drinks with additional benzoate as
preservative. The carcinogens are present all over and everywhere. You
can't eliminate any carcinogen from your environment, that's just the
risk of your life. Even oxygen can be considered as a "(bi)radical",
thus being a potential carcinogen. But you need oxygen for your
breathing, as long as you are alive... . Live itself is a risk.... .
And when you drink a soft drink, which smells ugly, this might be a
natural indicator that there a some compounds present, which are not
health promoting. Thus you will not drink all of the soft drink......
And getting older shows also that your body was in contact which much
radicals, carcinogens, and many other......

Steven

Borek

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Apr 12, 2006, 7:27:09 PM4/12/06
to
On Tue, 11 Apr 2006 14:04:30 +0200, Steven <ste...@chemie.fu-berlin.de>
wrote:

> ascorbate) or as a buffered solution. A soft drink may have a pH below
> 7, but not below pH 5 (in contrast to soda drinks, which are more

No idea what the definition of soft drink is, but it seems to me that many
drinks have pH lower then 5 just for taste. pH of beer is about 4.1 -
hardly soft drink, but for sure not something very acidic. Coca Cola is
about 4 too, these are CO2 saturated, but IIRC fruit juices may fall below
4 as well - and without carbonic acid.

Best,
Borek
--
http://www.chembuddy.com
http://www.ph-meter.info

Steven

unread,
Apr 12, 2006, 7:44:56 PM4/12/06
to
Fruit juices have more acidity through the content of fruit acids (for
example also ascorbic acid can be considered to be one of them).
Acidity in Coca Cola is mainly due to phosphoric acid and other acidic
contents. There is just a lot of carbon dioxide inside by pressure, but
it bubbles out of the solution very quickly, because the saturation
point for maximum content of carbon dioxide is not in that pH. The
carbon dioxide is only dissolved by pressure (physically disolved). A
cola is good example for a "carbonized" soft drink, but not a soda
drink.

dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

unread,
Apr 12, 2006, 9:52:04 PM4/12/06
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Dear Steven:

"Steven" <ste...@chemie.fu-berlin.de> wrote in message

news:1144877522....@u72g2000cwu.googlegroups.com...

Thanks for that.

...


>> > I guess you will vomit those either..... Also: there is
>> > printed a durability date (can be used until....... or:
>> > Do not use after.......).
>>
>> Thanks for the response. My real concern was is
>> there a handy substitute to replace benzoate? Those
>> manufacturers that added it to their products are now
>> going to be scrambling for options. Decreasing shelf
>> life is probably not an option, even if they could have
>> sterilized their product beforehand.
>
> Why are you concerned on the benzoate? The
> amount of benzene formed by decarboxylation is very
> low, and you have much more concentrations of
> carcinogens in all your environment.

...
> And getting older shows also that your body was in
> contact which much radicals, carcinogens, and many
> other......

My concern is:
1) for the children (and parents) that will be brainwashed into
thinking this is a problem, and
2) the companies that will suffer the lawsuits. I have ridden
with 3 or 4 companies down the tubes, and I hate to see people
out of work.

There are (at least) two companies involved. They are being sued
for exposing children to benzene levels in excess of that allowed
by (USA) federal standards. When lawyers get involved, any sort
of reasonable-ness can be seen to leave the scene.

There are a host of products that depend on benzoate to
control/limit biogrowth in the product. If there is a known
alternative, the manufacturer(s) haven't got a leg to stand on.
If there is not a known alternative, then they have a chance in
court. The interaction between benzoate and ascorbic acid has
been known for some long time, so "due diligence" isn't a defense
in court.

When they finish with benzoate, I expect Science will be required
to develop an arsenic-less cow.

David A. Smith


dlzc1 D:cox T:net@nospam.com N:dlzc D:aol T:com (dlzc)

unread,
May 10, 2006, 8:23:46 PM5/10/06
to
To the Group:

One of the major "clear soda" manufacturers in the USA has come
out with a "Fresh" configuration of their drink, that contains
citrate rather than benzoate. They have only six "all natural"
ingredients. Maybe they'll change their name to Six-Up?

David A. Smith


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