Author Topic: Proper forming of peracetic acid  (Read 2372 times)

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strangespice

  • Guest
Proper forming of peracetic acid
« on: May 28, 2000, 01:44:00 AM »
The info to prepare peracetic is hard to find.

Perhaps one of you serious fellows would care to help?

What I know;

1% H2SO4: GAA....stir 24h
A journal said to heat the GAA up to 50 deg before adding 35% H202... is this kosher?

I dont want a fucking space shuttle.

Anyway....supposedly a longer time to form the epoxide is needed as well. 48 h vs 18 or so.....


What I dont;

ratio of this hyped up GAA to H202
if the pinacolone rearrangement steps are the same... I dont know why they wouldn't be.

*&^%$#

strangespice

  • Guest
Re: Proper forming of peracetic acid
« Reply #1 on: May 28, 2000, 07:01:00 PM »
In the Aldrich catalog, it gives a warning about 32% peracetic acid exploding on heating.....

so I assume you wont heat it...(!)

......but really, I am going to have to pester you all on every board until someone coughs it up...I know its floatin' around out there... its not like I havent looked.

Organicum(my best text) gives perbenzoic prep, pertungstic prep, but no peracetic.

Search engine yields SHIT.

C'mon

*&^%$#

hey_man

  • Guest
Re: Proper forming of peracetic acid
« Reply #2 on: May 28, 2000, 07:12:00 PM »
Doing a search on Rhodium's info site produces the following...


Documents 1 - 8 of 8 matches, best matches first.
 
[peracetic.oxidation.txt]
Subject: Peracetic acid oxidation of isosafrole From: rschaap@unixg.ubc.ca (Jessica Robin Schaap) Date: 1996/04/07 I've searched the ADC archives and haven't found anything on the peracetic acid oxidation ...

http://rhodium.lycaeum.org/chemistry/peracetic.oxidation.txt

- 40k - 1999-02-01

[mdp2p.patent.txt]
... Phenylpropanones are known to be prepared by oxidation (using peracids, such as performic or peracetic acid) of Phenylpropenes, to give an intermediate glycol (via epoxide), which is successively converted ...

http://rhodium.lycaeum.org/chemistry/mdp2p.patent.txt

- 11k - 1999-02-01

[safrole.eugenol.txt]
... of isoeugenol to form the intermedate diol which is dehydrated to MVK; and b.) the reaction of peracetic acid with isoeugenol to form the epoxide, which is then hydrolyzed to the diol, and lastly dehydrated ...

http://rhodium.lycaeum.org/chemistry/safrole.eugenol.txt

- 35k - 1999-02-01

[wacker.nitrites.txt]
... a process for producing DMPA by reacting 1-(3,4- dimethoxyphenyl)propylene with peroxides such as peracetic acid, followed by treating the resultant diol type products with acidic substances such as zinc ...

http://rhodium.lycaeum.org/chemistry/wacker.nitrites.txt

- 36k - 1999-02-01

Preparation and Use of ( )-p-2,8-menthadien-1-ol
... operations are easily carried out. In a later paper (Reference 183) the cis- isomer is prepared by peracetic acid oxidation of ( )-delta4-Carene, but it is not clear whether this is a practical method ...

http://rhodium.lycaeum.org/chemistry/thc/page9.html

- 9k - 1999-09-01

[guest.phenylacetone.txt]
... by means of the oxidation of isoeugenol-methylether by organic peracids (performic acid or peracetic acid), to yield an intermediate diol which is subsequently converted into a ketone by acidic hydrolysis ...

http://rhodium.lycaeum.org/chemistry/guest.phenylacetone.txt

- 18k - 1999-02-01

Rhodium: Chemistry Archive
... * MDP2P from Safrole via MDP2Pol * Purification of MDP2P via its NaI complex Peracid methods * Peracetic acid oxidation of isosafrole to MDP2P? * Performic acid oxidation of isosafrole with DCM as solvent ...

http://rhodium.lycaeum.org/chemistry/index.html

- 27k - 1999-09-07

[guest.eugenol.txt]
... by means of the oxidation of isoeugenol-methylether by organic peracids (performic acid or peracetic acid), to yield an intermediate diol which is subsequently converted into a ketone by acidic hydrolysis ...

http://rhodium.lycaeum.org/chemistry/guest.eugenol.txt

- 38k - 1999-05-05





Artful_Dodger

  • Guest
Re: Proper forming of peracetic acid
« Reply #3 on: May 29, 2000, 09:13:00 PM »
Ouch...feel like a school kid busted for not doing his homework  :)


Nutmeg238

  • Guest
Re: Proper forming of peracetic acid
« Reply #4 on: June 01, 2000, 05:25:00 PM »
I found this in US patent 2,692,271.
Column 3 lines 6-32:
 
Although peracids generally may be emplyed as epoxidizing agents,
it will be found, as a practical matter, that peracetic acid will
be the epoxidizing agent generally employed, and that acid has
been used throughout the examples given hereinafter.  The peracetic
acid may be effectively prepared by reacting acetic acid with aqueous
hydrogen peroxide in the presence of about 1% sulfuric acid as a
reaction catalyst.  The reaction proceeds with glacial acetic acid
or aqueous acetic acid.  The hydrogen peroxide may be the commercial
27.5% or 100 volume product or may be aqueous solutions of high
peroxide content as, for instance, 50% to 90% H2O2.  Peracetic acid
may similarly be prepared by reaction of acetic anhydride with hydrogen
peroxide by oxidation of aldehydes, U.S. patent 2,314,385, or by the
method described in U.S. patent 2,490,800 issued December 13, 1949,
to Greenspan.
When employing the resultant peracetic acid as the epoxidizing agent,
it is necessary to neutralize any strong acid, e. g. sulfuric acid,
present as catalyst from its formation.  This may be done either by
neutralizing the sulfuric acid content with an alkali, such as caustic
soda, or by buffering the solution with a material such as sodium
acetate.

Image replaced by text to facilitate archiving.
Edited by Nutmeg238 6/20/00.

-----------------------

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Application Files

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(a) After a patent has been issued or a statutory invention
registration has been published, the specification, drawings,
and all papers relating to the case in the file of the patent
or statutory invention registration are open to inspection by
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Nutmeg238

  • Guest
Re: Proper forming of peracetic acid
« Reply #5 on: June 03, 2000, 09:26:00 AM »
Also, they give an example in US patent 2802025 where CH3COOOH is made from CH3COOH, H2O2 and H2SO4 which are allowed to come to equilibrium in 12 to 16 hr.  See also US patent 5098598 which discusses the stability of percarboxylic acids and US patent 4168274 which discloses a continuous epoxidation process which uses aqueous and organic phases.  Also, search class 562 subclasses 2, 4 and 6 which covers percarboxylic acids and epoxidation.  You can search it online at

http://www.uspto.gov

or if you're near the patent office go there and you can search all the way back to patent number 1. If you're near a patent office in another country they might have US patents.........