13038-47-6Relevant articles and documents
Production of conjugated linoleic acids through KOH-catalyzed dehydration of ricinoleic acid
Yang, Lin,Huang, Yu,Wang, Han Qing,Chen, Zhen-Yu
, p. 23 - 31 (2002)
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°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°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°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.
Suhara
, p. 1702 (1967)
Transformation of Methyl Linoleate to its Conjugated Derivatives with Simple Pd(OAc)2/Lewis Acid Catalyst
Senan, Ahmed M.,Zhang, Sicheng,Qin, Shuhao,Chen, Zhuqi,Yin, Guochuan
, p. 1481 - 1489 (2017/11/03)
With the rapid depletion of fossil resources, the exploitation of biomass to partly replace fossil resources as the source of carbon in the chemical industry constitutes a promising alternative for the near future. This work introduces catalytic transformation of vegetable oil, i.e., methyl linoleate, to its conjugated esters by a simple Pd(OAc)2/Sc(OTf)3 catalyst, which has extensive applications in industry. It was found that adding non-redox metal ions like Sc(III) to a simple Pd(OAc)2 catalyst can effectively improve its isomerization activity in toluene/t-BuOH solvent, whereas Pd(OAc)2 alone is inactive. Preliminary mechanistic investigations together with previous studies suggested that the in situ-generated heterobimetallic Pd(II)/Sc(III) dimer serves as the key species for methyl linoleate isomerization, and the reaction proceeds by [1,3]-hydrogen shift mechanism involving a formal Pd(II)/Pd(IV) cycle.
Sustainable and efficient methodology for CLA synthesis and identification
Moreno, Maria,Gomez, M. Victoria,Cebrian, Cristina,Prieto, Pilar,De La Hoz, Antonio,Moreno, Andres
, p. 2584 - 2594 (2013/02/23)
Microwave-assisted organic synthesis and continuous-flow techniques have been successfully employed for the preparation of conjugated linoleic acids (CLA), compounds with high health beneficial effects. A good production rate of CLA was obtained. A sustainable methodology for the differentiation of both positional and geometrical CLA isomers (diene), based on the analysis by NMR spectroscopy of the resulting Diels-Alder cycloadducts with an appropriate dienophile, was developed.
