Kinetics of enzymatic esterification of oleic acid and decanol for wax ester and evaluation of its physico-chemical properties

Rani, K. N. Prasanna; Neeharika, Tulasi Sri Venkata Ramana; Kumar, T. Prathap; Satyavathi, B.; Sailu, Ch.; Prasad, R. B. N.

doi:10.1016/j.jtice.2015.04.011

Cited by 31 publications

(13 citation statements)

References 19 publications

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“…The activation energy for cetyl caprate synthesis catalyzed by immobilized lipase was found to be 11.0 kcal/mol (45.99 kJ/mol), that in particular fall in between the scale of enzyme catalyzed reactions, proportionate to that reported in the literature [12,20]. The activation energy value for esterification of oleic acid and decanol using Novozym 435 as a catalyst in hexane medium is reported as 16.24 kcal/mol [21]. The ln K = −E a ∕RT + ln A minimal activation energy estimate indicates superior catalytic proficiency of immobilized lipase [22].…”

Section: Effect Of Temperaturementioning

confidence: 68%

Enzymatic synthesis of cosmetic grade wax ester in solvent free system: optimization, kinetic and thermodynamic studies

Jaiswal

Rathod

2019

SN Appl. Sci.

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The enzymatic synthesis of cetyl caprate, a cosmetic grade ester was studied by esterification of cetyl alcohol and capric acid using Fermase CALB™10000 under solvent free condition. The process parameters namely, temperature, enzyme loading, molar ratio, agitation speed have been investigated and optimized to attain maximum yield of cetyl caprate. The maximum yield of 91.9% was obtained in 80 min under optimized conditions of 50 °C temperature, 3% enzyme loading, capric acid:cetyl alcohol ratio of 1:3, and 200 rpm stirring speed. The enzyme operational stability study reveals that enzyme can retain its original activity for the synthesis of cetyl caprate and could be reused up to five to six times without any notable loss of catalytic activity. The kinetics of the reaction was derived by employing non-linear regression consideration, and the experimental results and kinetic evaluation showed that reaction obeys ping-pong bi-bi model. The kinetic parameters, V max = 21.886 M/min/g catalyst, K A = 1.194 × 10 −2 M, K B = 8.4512 M, K iA = 2.02 × 10 −2 M, K iB = 3.55 × 10 −4 M and SSE = 4.31 × 10 −5 measured from initial rate data were used to replicate experimental results with good agreement. The thermodynamic parameters, i.e., change in enthalpy, Gibb's free energy, change in entropy was evaluated at different operating temperatures. Thus, current research work strikes a significant imprint in the cosmetic industry by synthesizing green and natural product using biocatalysis under solvent free condition.

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Section: Effect Of Temperaturementioning

confidence: 68%

Enzymatic synthesis of cosmetic grade wax ester in solvent free system: optimization, kinetic and thermodynamic studies

Jaiswal

Rathod

2019

SN Appl. Sci.

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“…Upon optimization, the integrated rate equation associated to this mechanism would result in the form of a parametric equation (Equation (4)), which contains two parameters ( α and β ) and the constant rate of the direct reaction ( k 1 ) can be calculated using Equation (5) [ 63 ]:

where [ S p 0 ] and [ S k 0 ] are the concentrations of the palmitic acid and kojic acid, respectively, X is conversion (%), α is parameter related to equilibrium conversion ( K ), β is parameter related to rate constant ( k ), t is the reaction time.…”

Section: Methodsmentioning

confidence: 99%

Kinetics and Optimization of Lipophilic Kojic Acid Derivative Synthesis in Polar Aprotic Solvent Using Lipozyme RMIM and Its Rheological Study

et al. 2018

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The synthesis of kojic acid derivative (KAD) from kojic and palmitic acid (C16:0) in the presence of immobilized lipase from Rhizomucor miehei (commercially known as Lipozyme RMIM), was studied using a shake flask system. Kojic acid is a polyfunctional heterocycles that acts as a source of nucleophile in this reaction allowing the formation of a lipophilic KAD. In this study, the source of biocatalyst, Lipozyme RMIM, was derived from the lipase of Rhizomucor miehei immobilized on weak anion exchange macro-porous Duolite ES 562 by the adsorption technique. The effects of solvents, enzyme loading, reaction temperature, and substrate molar ratio on the reaction rate were investigated. In one-factor-at-a-time (OFAT) experiments, a high reaction rate (30.6 × 10−3 M·min−1) of KAD synthesis was recorded using acetone, enzyme loading of 1.25% (w/v), reaction time of 12 h, temperature of 50 °C and substrate molar ratio of 5:1. Thereafter, a yield of KAD synthesis was optimized via the response surface methodology (RSM) whereby the optimized molar ratio (fatty acid: kojic acid), enzyme loading, reaction temperature and reaction time were 6.74, 1.97% (w/v), 45.9 °C, and 20 h respectively, giving a high yield of KAD (64.47%). This condition was reevaluated in a 0.5 L stirred tank reactor (STR) where the agitation effects of two impellers; Rushton turbine (RT) and pitch-blade turbine (PBT), were investigated. In the STR, a very high yield of KAD synthesis (84.12%) was achieved using RT at 250 rpm, which was higher than the shake flask, thus indicating better mixing quality in STR. In a rheological study, a pseudoplastic behavior of KAD mixture was proposed for potential application in lotion formulation.

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“…Tetramethylsilane (TMS) was used as the internal reference (δ 0.00). The high resolution mass spectra Wax esters are biodegradable, non-toxic, and are obtained from renewable sources [25] including vegetable oil crops such as olive [26], soya [27] and sunflower [28]. Similar esters of different chain lengths may also act as insecticides.…”

Section: General Experimental Procedures and Apparatusmentioning

confidence: 99%

Insecticidal Properties of a Highly Potent Wax Isolated from Dolichandra cynanchoides Cham

2016

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Bioassay-guided fractionation of an ethanolic extract of the aerial parts of Dolichandra cynanchoides Cham. (Bignoniaceae) led to the isolation of a natural wax with anti-insect activity against Spodoptera frugiperda (Noctuidae) and Epilachna paenulata (Coleptera). The compound was identified spectroscopically as an ester of a C27 fatty acid and a C25 alcohol, pentacosyl heptacosanoate (1). The effective doses of 1 for 50% feeding inhibition (ED 50 ) of S. frugiperda and E. paenulata were 0.82 and 8.53 µg/cm 2 , respectively, in a choice test, while azadirachtin showed ED 50 of 0.10 and 0.59 µg/cm 2 , respectively. In a no-choice test, both insects refused to feed on leaves treated with 1 at doses of 0.1 µg/cm 2 or greater inhibiting larval growth and dramatically reducing survival. The lethal doses 50 (LD 50 ) of 1 were 0.39 and 0.68 µg/cm 2 for S. frugiperda and E. paenulata, respectively. These results indicate that 1 has potential for development as botanical insecticides. Similar esters might be obtainable in large quantities as many edible crops produce wax esters that are discarded during food processing. Research on these materials could lead to the detection of similar waxes with insecticidal activity.

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Kinetics of enzymatic esterification of oleic acid and decanol for wax ester and evaluation of its physico-chemical properties

Cited by 31 publications

References 19 publications

Enzymatic synthesis of cosmetic grade wax ester in solvent free system: optimization, kinetic and thermodynamic studies

Enzymatic synthesis of cosmetic grade wax ester in solvent free system: optimization, kinetic and thermodynamic studies

Kinetics and Optimization of Lipophilic Kojic Acid Derivative Synthesis in Polar Aprotic Solvent Using Lipozyme RMIM and Its Rheological Study

Insecticidal Properties of a Highly Potent Wax Isolated from Dolichandra cynanchoides Cham

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