US EPA

1518487 

Journal Article 

Review 

Derivatization of carbonyl compounds with 2,4-dinitrophenylhydrazine and their subsequent determination by high-performance liquid chromatography 

Uchiyama, S; Inaba, Y; Kunugita, N 

2011 

Yes 

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
ISSN: 1570-0232
EISSN: 1873-376X 

879 

17-18 

1282-1289 

English 

20970389 

10.1016/j.jchromb.2010.09.028 

WOS:000291131900010 

http://://WOS:000291131900010
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Derivatization of carbonyl compounds with 2,4-dinitrophenylhydrazine (DNPH) is one of the most widely used analytical methods. In this article, we highlight recent advances using DNPH provided by our studies over past seven years. DNPH reacts with carbonyls to form corresponding stable 2,4-DNPhydrazone derivatives (DNPhydrazones). This method may result in analytical error because DNPhydrazones have both E- and Z-stereoisomers caused by the CN double bond. Purified aldehyde-2,4-DNPhydrazone demonstrated only the E-isomer, but under UV irradiation and the addition of acid, both E- and Z-isomers were seen. In order to resolve the isometric problem, a method for transforming the CN double bond of carbonyl-2,4-DNPhydrazone into a C-N single bond, by reductive amination using 2-picoline borane, has been developed. The amination reactions of C1-C10 aldehyde DNPhydrazones are completely converted into the reduced forms and can be analyzed with high-performance liquid chromatography. As a new application using DNPH derivatization, the simultaneous measurement of carbonyls with carboxylic acids or ozone is described in this review. 

Derivatization; Carbonyl compounds; Carboxylic acids; 2,4-Dinitrophenylhydrazine; Isomerization; Reductive amination; Ozone