Production of conjugated linoleic acids through KOH-catalyzed dehydration of ricinoleic acid

Chem Phys Lipids. 2002 Oct;119(1-2):23-31. doi: 10.1016/s0009-3084(02)00052-x.

Abstract

Production of conjugated linoleic acids (CLA) using castor oil as starting material involves conversion of ricinoleic acid to methyl 12-mesyloxy-octadec-9-enoate (MMOE) followed by dehydration. This process usually uses 1,8-diazabicyclo-(5.4.0)-undec-7-ene (DBU) as an expensive dehydrating reagent. The present study reports that potassium hydroxide (KOH) can serve as a dehydrating reagent in replacement of DBU. The results showed that conversion of MMOE to CLA catalyzed by KOH was an efficient reaction, with a 77% conversion efficiency at 80 degrees C. The CLA isomeric profile produced in KOH-catalyzed dehydration reaction was similar to that catalyzed by DBU. The CLA mixture produced in KOH-catalyzed dehydration of MMOE at 80 degrees C contained 72% 9c,11t-18:2 and 26% 9c,11c-18:2 while in that catalyzed by DBU, 9c,11t-18:2 and 9c,11c-18:2 accounted for 78 and 16%, respectively. It was found that the temperature of dehydration was an important factor in the determination of CLA isomer composition and yield of conversion. Elevating the temperature from 78 to 180 degrees C decreased not only the conversion efficiency but also production of total c,t-18:2 and c,c-18:2 isomers regardless of dehydration catalyzed by either DBU or KOH. It is concluded that KOH may replace DBU as a dehydrating reagent in conversion of MMOE to CLA when the reaction conditions are optimized.

MeSH terms

  • Castor Oil / chemistry
  • Catalysis
  • Hydroxides / chemistry*
  • Indicators and Reagents / chemistry
  • Isomerism
  • Linoleic Acid / chemistry*
  • Potassium Compounds / chemistry*
  • Ricinoleic Acids / chemistry*

Substances

  • Hydroxides
  • Indicators and Reagents
  • Potassium Compounds
  • Ricinoleic Acids
  • Castor Oil
  • Linoleic Acid
  • ricinoleic acid
  • potassium hydroxide