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How would you go about synthesising a fatty acid amide, preferably by means of a high-yield reaction. Please provide an explanation that I, as a grade 12 chemistry graduate, could understand.

I am familiar with:

  • Fatty acids
  • Carboxylic acid
  • Equilibrium reactions & constants
  • Amide groups
  • Amines
  • Alkanols
  • Esterification

If you need to use terms I may be unfamiliar with, it would be nice if you could explain them or provide a link to an explanation.

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This is very similar to your other question on amide synthesis: chemistry.stackexchange.com/questions/2751/…. Could these be combined into one question? –  Ben Norris Dec 12 '12 at 0:16
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1 Answer 1

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Schotten-Baumann Reaction

I found the solution to my question and it is the Schotten-Baumann reaction which takes an acyl chloride (which can be synthesised from a carboxylic acid via the methods detailed in the next section) and an amine to form an amide, a hydrogen chloride.

enter image description here (1)


[Net reaction: $ RCOCl+NH_2 R' \rightarrow RCONHR' + HCl $]


Synthesis of Acyl Chlorides

To create acyl chlorides from carboxylic acids the following three reactions will suffice:

$ RCOOH (l) + PCl_5 (s) \rightarrow RCOCl (aq) + POCl_3 (aq) + HCl (g) $

$ 3 RCOOH (l)+ PCl_3 (s) \rightarrow 3 RCOCl (aq) + H_2 PO_3 (aq) $

$ RCOOH (l) + SOCl_2 (s) \rightarrow RCOCl (aq) + SO_2 (g) + HCl (g) $

(2)


Reference List (APA style)

  1. Schotten-Baumann Reaction Schotten-Baumann Conditions (n.d.). Retrieved December 22 2012 from http://www.organic-chemistry.org/namedreactions/schotten-baumann-reaction.shtm.
  2. Clarke, J. (2004). CONVERTING CARBOXYLIC ACIDS INTO ACYL CHLORIDES (ACID CHLORIDES). Retrieved December 22 2012 from http://www.chemguide.co.uk/organicprops/acids/pcl5.html.
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