Enzymatic synthesis of some Wax‐esters

Abstract

The Mucor miehei lipase, immobilized on a macroporous anion-exchange resin (Lipozyme TM), was used to catalyze esterification and interesterification for the synthesis of wax-esters. The first series of saturated esters, from 20 to 28 carbon atoms, were obtained with more than 80% yield. These esters are liquid up to 24 carbon atoms. Monounsaturated wax-esters from 28 to 36 carbon atoms, were synthesized with yields greater than 70%. With few exceptions all these compounds are liquid up to 34 carbon atoms. Attempts of alcoholysis involving the ricinoleyl chain, revealed the remarkable selectivity of Lipozyme. Primary esters were found to be the sole reaction products (yields from 79 to 81.5%). It was possible to prepare diesters from octanediol and suberic acid with good yields (84-92%). Unfortunately yields were moderate in the synthesis of monoesters. 1,2-alkanediol monolaurates were easily and selectively synthesized, but with a low yield. A fair amount of secondary ester was found besides the expected primary ester. A mechanism involving an equilibrium between both esters via a cyclic intermediate accounted for the acyl migration.

Synthesis and characterization of some long‐chain diesters with branched or bulky moieties

“…Some other patent syntheses (21,22) of compounds such as the present ones have been reported. Nonpatent syntheses include some compounds with neopentylglycol as diol (23), compounds derived from α,α-dimethylalkanoic acids and polyols (24), esters from dodecanedioic acid, and mono-alcohols (25) as well as the enzymatic synthesis of related wax esters (26). Besides their synthesis, the mass spectrometric behavior of compounds similar to the present ones was studied, including esters of neopentyl glycol (27), other esters of polyols of neopentane (28)(29)(30)(31)(32)(33), the decomposition products of neopentylglycol dilaurate (34), and ethane (35,36) and propanediol (35) diesters.…”

Renewable feedstocks for lubricant production

“…Thus, wax esters have been obtained in high yield by esterifi cation of FAs with longchain alcohols [308,[315][316][317][318][319][320][321][322][323][324] and in moderate to good yields by interesterifi cation (alcoholysis) of TAGs or natural fats and oils with long-chain alcohols [318,320,322,[325][326][327]. For example, wax esters having compositions approaching that of jojoba were prepared in high yield via lipase (Novozym 435 and papaya)-catalysed esterifi cation of Crambe FAs with Camelina alcohols or Camelina FAs with Crambe alcohols [308].…”

“…For example, wax esters having compositions approaching that of jojoba were prepared in high yield via lipase (Novozym 435 and papaya)-catalysed esterifi cation of Crambe FAs with Camelina alcohols or Camelina FAs with Crambe alcohols [308]. Wax esters have also been prepared by lipase-catalysed alcoholysis of alkyl esters of fatty acids with long-chain alcohols [323,328,329].…”

Physico-chemical properties of wax esters synthesised from corresponding alcohols using hydrobromic acid and hydrogen peroxide action

“…In the recent past, wax esters have been synthesized by enzyme-catalyzed reactions [12][13][14][15][16][17]. Primary aliphatic alcohols, R-CH 2 OH, react with H 2 O 2 under mild conditions in a two-phase liquid-liquid system with ethylene dichloride as a solvent in the presence of Br 2 or HBr to yield selectively the corresponding ester [18].…”