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Subject:
From:
James Fischer <[log in to unmask]>
Reply To:
Informed Discussion of Beekeeping Issues and Bee Biology <[log in to unmask]>
Date:
Thu, 4 Aug 2016 07:12:35 -0400
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A few inaccuracies, first some chemistry issues:
 
Richard said:

> Butyric anhydride does not react with oxygen in the air.  
> ...one molecule of butyric anhydride reacts with one 
> molecule of water in either air or water
 
Yes the word "anhydride" should be self-explanatory. And yes, one removes
water if one were to try to make the anhydride from the acid, but the
reaction of the anhydride with the air can be described equally well as
either "hydrolysis" or "oxidation".  Mere semantics, I guess.  But one would
have to show a far smaller reaction in a far lower moisture atmosphere to
conclude that the oxygen and hydrogen has to be specifically provided in the
form of water to react.   As far as I know, very low humidity has never made
butyric anhydride less effective or less stinky.  
 
> Butyric acid is not one of the byproducts
> it is the only product of such hydrolysis.
 
Volatile organic compounds are also produced by the reaction (the very foul
odor). The proof is that butyric acid is far less foul-smelling than the
anhydride, despite the much lower vapor pressure of the anhydride, which
(for most substances) would tend to reduce the "evaporation", and hence the
fume level. This is the reason why the anhydride is what is sold, rather
than the acid.  
 
> Nor does it act as a corrosive when reacting with oxygen in water.  
> What actually happens is one molecule of butyric anhydride reacts with one
molecule 
> of water in either air or water and forms two molecules of butyric acid.  
 
The word "CORROSIVE" is featured in very large bold print on every MSDS for
the chemical.
It is a class 8 Corrosive Liquid under CFR 49 Section 172 (the shipping
regulations).
If one gets some in one's eye or on one's skin, one will find out exactly
how corrosive.  

Randy said:

> and as far as human safety, it is a naturally-occurring 
> molecule in your stomach contents
 
This is not an good argument for safety at all. Stomach acid also contains
hydrochloric acid and formaldehyde in significant amounts.  By the same
logic, those two chemicals would somehow be "safe".  A chemical's appearance
in stomach acids is not a glowing endorsement of "safety".

Peter said:

>  Butyric acid is listed by the FDA as a synthetic flavoring substance that
is generally recognized as safe (GRAS).

Butyric acid's CAS number is 107-92-6  Butyric anhydride's is 106-31-0.
They are two very different chemicals.  The EPA has no "Tolerance" for
Butyric anhydride in food any more, and the FDA does not list it on the
"generally recognized as safe" (GRAS) list.  This means that it simply is
not allowed in food at all, and under the FDA's adulteration rules, one may
not even bring such a substance in close contact with food.   The EPA really
did expect everyone to stop using the chemical, as they said in their notice
Revoking the "exemption from the requirement for a tolerance" for butyric
anhydride: 

"the existing stocks of the chemicals are presumed to have been exhausted
more than a year ago, giving ample time for any treated food to clear trade
channels."

http://web.archive.org/web/20030429143659/http://www.epa.gov/pesticides/tole
rance/tolrev.htm
http://tinyurl.com/gvugneh

http://web.archive.org/web/20030528155501/http://www.epa.gov/fedrgstr/EPA-PE
ST/1998/January/Day-21/p1356.htm
http://tinyurl.com/zzrhtoe

(In the above, the government calls the chemical "Butanoic Anhydride", which
is a synonym. Same CAS number.)

So, what part of "no food use" is the Bee-L debate team debating here?


Medhat said:

> In the USA and Canada there is no Maximum Residues 
> limit (MRL) for butyric acid in honey. Few years ago the 
> Canadian Food Safety agency (CFIA) wanted to regulate 
> it but after discussion with the industry and proofing 
> its use in other products they dropped there request.

Not sure how Canada's CFIA works, but I do know that Canada adopts a lot of
US EPA rules unchanged.  Here in the USA, the FDA allows a certain specific
list of things in food, and anything not specifically allowed is prohibited.
The EPA can publish a "tolerance", same as a maximum residue limit,  but
when the RPA "exemption from the requirement for a tolerance" for butyric
anhydride was revoked in 1998, so there simply is no legal food use for the
anhydride, as the FDA has never allowed it even in a "close proximity to
food" or "close contact" with food.

The manufacturer has been very sneaky about mislabeling the anhydride as the
acid.  Quite a few people call it "acid" rather than "anhydride", even in
this discussion.  The cancellation of the EPA's registration of the
substance (it used to have the EPA pesticide registration number 8426-2)
means that they've been making the stuff for 28 years after having their
registration was cancelled, using this confusion to their advantage.

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