Chemistry:Acetoacetamide

From HandWiki

Acetoacetamide is an organic compound with the formula CH
3COCH
2CONH
2. It is the amide of acetoacetic acid. It is produced by treating diketene with aqueous ammonia[1]

It results from degradation of the sweetner acesulfame potassium.[2]

Acetoacetanilide (CH
3COCH
2CONH
2) is the N-phenyl derivative of acetoacetamide. It is also prepared from diketene.[3] It and various derivatives are used in the production of organic pigments called arylide yellows, one example being Pigment Yellow 74. Many analogues have been prepared.[4] To make the dyes, acetoacetanilides are coupled to diazonium salts, "azo coupling".[5]

Acetoacetylation with diketene followed by diazo coupling. The ketohydrazone tautomer is shown.

References

  1. ↑ Miller, Raimund; Abaecherli, Claudio; Said, Adel; Jackson, Barry (2001). "Ketenes". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a15_063. ISBN 978-3-527-30385-4. 
  2. ↑ George, V.; Arora, S.; Wadhwa, B. K.; Singh, A. K. (August 2010). "Analysis of multiple sweeteners and their degradation products in lassi by HPLC and HPTLC plates". Journal of Food Science and Technology 47 (4): 408–413. doi:10.1007/s13197-010-0067-4. ISSN 0022-1155. PMID 23572661. 
  3. ↑ Williams, Jonathan W.; Krynitsky, John A. (1941). "Acetoacetanilide". Organic Syntheses 21: 4. doi:10.15227/orgsyn.021.0004. 
  4. ↑ Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3. 
  5. ↑ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371




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