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Amide with erucic acid and formaldehyde

Amide with erucic acid and formaldehyde - Chemistry Forum

Amide with erucic acid and formaldehyde - Chemistry Forum. Discuss chemical reactions, chemistry.


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  #1  
Old 08-18-2003, 05:39 PM
Brewbeaker
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Default Amide with erucic acid and formaldehyde



Trying to make erucimide and wonder if pressure is required. Is so how much.
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  #2  
Old 08-18-2003, 10:59 PM
Brewbeaker
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Default Amide with erucic acid and ammonia

[Only registered users see links. ] (Brewbeaker) wrote in message news:<37d39293.0308180939.4478d75a@posting.google. com>...

Sorry folks. had formaldehyde on the brain.

I want to make erucamide. I think you need gaseous ammonia and erucic
acid. The question is does it require pressure and if so how much.

Can't reply to your email Larry.
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  #3  
Old 08-19-2003, 01:09 PM
Larry Smith
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Default Amide with erucic acid and ammonia


"Brewbeaker" <[Only registered users see links. ]> wrote in message
news:37d39293.0308181459.191b7da4@posting.google.c om...
news:<37d39293.0308180939.4478d75a@posting.google. com>...

Wonder why? Others have complained lately that my email doesn't seem to be
valid. (It is)

Simple reference literature sometimes would lead one to believe that amides
are more easily formed than they actually are.
Formation of an ammonium salt with the acid, followed by thermal breakdown
of the salt to yield the amide, works pretty
easily when both reactants have relatively high boiling points.

However, when one of them, as the ammonia, has a low boiling point, thermal
degradation of the salt also releases some of the lighter material.

Holding pressure can help in a reaction such as the one you have chosen.

A good example is the commercial production of dimethylamide of tall oil
fatty acids. Pressure can help, but you also need to recover the amine
lost when the water is distilled away, and return it to the reaction ( for
economy as well as regulatory reasons). (If you just started with the 1:1
molar amine salt and drove it to the amide, your conversion would be very
low...below 50%, in a one pass scheme.)

If you use an excess of the amine or ammonia, then you can - to some
degree - improve the reaction and reduce the production of side reaction
products which could arise in some cases.

If you wanted high conversions quickly, you might convert the acid to the
acyl halide and react that with ammonia. Again, you might also get some
byproducts
which you may want to remove.

I realize this is very general, and you may be able to find syntheses which
will promise better results.



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  #4  
Old 08-20-2003, 06:14 PM
Larry Smith
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Default Amide with erucic acid and ammonia

Almost agree with you, but not quite. Have done it this way, but making the
methyl ester can also be time consuming, slow to go to completion. I did
some work on this a couple of years ago, and quickly came to the conclusion
that this reaction might not be the best way to go for commercial production
in the facilities we had.

In the lab, you can prepare it in a number of ways. In a plant, constraints
posed by equipment, economy, and environment often limit one's choices.




"Eric Lucas" <[Only registered users see links. ].net> wrote in message
news:NrB0b.106619$[Only registered users see links. ].worldnet.att.net...
the



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  #5  
Old 08-21-2003, 01:31 PM
Larry Smith
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Default Amide with erucic acid and ammonia

This process is relatively widely used to produce methyl esters.

From what I of know of the process, a little more than methanol and
methoxide are required. Our guys in Australia worked on this a good bit
, using cocotriglycerides, but couldn't get the purity and conversion they
needed, and there wasn't enough economic elastic in the market to allow
further purification. I think they missed a trick, which I could not divulge
because of a confidentiality agreement.

I have never tried to produce the amide directly from a triglyceride, mainly
because of the secondary processes to remove the (unwanted) glycerine,
ammoniated residuals, etc from the product. Have you done this, and is it
a reasonable commercial synthesis?



"Frank Martin" <[Only registered users see links. ].au> wrote in message
news:bi0qle$jtt$[Only registered users see links. ].au...
which
commercially
seem
(
to
syntheses


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  #6  
Old 08-25-2003, 11:38 AM
Bob Burns
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Default Amide with erucic acid and ammonia

WE transesterified high erucic rapeseed oil with NaOMe, then distilled to
separate the esters.

--
Bob Burns
Mill Hall PA
email [Only registered users see links. ]


"Frank Martin" <[Only registered users see links. ].au> wrote in message
news:bi0qle$jtt$[Only registered users see links. ].au...
which
commercially
seem
(
to
syntheses


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