Related Experiment Video
Updated: Apr 27, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Formation of monochloropropane-1,2-diol and its esters in biscuits during baking
Burçe Ataç Mogol1, Céline Pye, Warwick Anderson
1Department of Food Engineering, Hacettepe University , Beytepe, 06800 Ankara, Turkey.
Abstract:
The formation of free monochloropropane-1,2-diol (3-MCPD and 2-MCPD) and its esters (bound-MCPD) was investigated in biscuits baked with various time and temperature combinations. The effect of salt as a source of chloride on the formation of these processing contaminants was also determined. Kinetic examination of the data indicated that an increasing baking temperature led to an increase in the reaction rate constants for 3-MCPD, 2-MCPD, and bound-MCPD. The activation energies of formation of 3-MCPD and 2-MCPD were found to be 29 kJ mol(-1). Eliminating salt from the recipe decreased 3-MCPD and 2-MCPD formation rate constants in biscuits by 57.5 and 85.4%, respectively. In addition, there was no formation of bound-MCPD in biscuits during baking without salt. Therefore, lowering the thermal load or limiting the chloride concentration should be considered a means of reducing or eliminating the formation of these contaminants in biscuits. Different refined oils were also used in the recipe to test their effect on the occurrence of free MCPD and its esters in biscuits. Besides the baking process, the results also confirmed the role of refined oil in the final concentration of these contaminants in biscuits.
More Related Videos
Related Concept Videos
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Esters to β-Ketoesters: Claisen Condensation Mechanism
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

