Synthesis of cocoa butter equivalent by lipase‐catalyzed interesterification in supercritical carbon dioxide

Liu, Kuan-Ju; Cheng, Hao-Yuan; Chang, Rey-Chang; Shaw, Jei‐Fu

doi:10.1007/s11746-997-0257-z

Cited by 42 publications

(19 citation statements)

References 13 publications

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“…Thus, lipase-catalyzed reactions in SCCO 2 have been carried out for such reactions as hydrolysis of tripalmitin (5) and canola oil (6); alcoholysis of cod liver oil (7) and palm kernel oil (8); glycerolysis of soybean oil (9); synthesis of oleoyloleate from oleic acid (10)(11)(12); acylation of glucose with lauric acid (13); thioesterification between oleic acid and butanethiol (14); transesterifications of milk fat with canola oil (15); tristearin with palm oil (16); palm oil with stearic acid (SA) (17); triolein with ethyl behenate and behenic acid (18,19); triolein with SA (20) and propyl acetate with geraniol (21); and randomization of fat and oils (22).…”

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confidence: 99%

Lipase‐catalyzed esterification of stearic acid with ethanol, and hydrolysis of ethyl stearate, near the critical point in supercritical carbon dioxide

Nakaya

Nakamura

Miyawaki

2002

J Americ Oil Chem Soc

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The effect of pressure on the lipase-catalyzed reaction in supercritical carbon dioxide (SCCO 2 ) was investigated for the esterification of stearic acid (SA) with ethanol and the hydrolysis of ethyl stearate (ES) near the critical point, ranging from 6 to 20 MPa in pressure and 35 to 60°C in temperature. The esterification rate of SA began to increase near the critical point and kept increasing steadily with an increase in pressure, reflecting the increase in SA solubility in SCCO 2 . The hydrolysis rate of ES showed a maximum at a pressure near the critical point. When the reaction was carried out with an initial overall ES concentration below its solubility limit in SCCO 2 , the maximum pressure shifted along the extended line of the gas-liquid equilibrium in the supercritical region in the pressure-temperature phase plane. This seems to be related to the singular behavior of some properties in SCCO 2 along this line reported in the literature. These results show the importance of pressure, as well as temperature, as a parameter to control enzyme reactions in SCCO 2 .

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confidence: 99%

Lipase‐catalyzed esterification of stearic acid with ethanol, and hydrolysis of ethyl stearate, near the critical point in supercritical carbon dioxide

Nakaya

Nakamura

Miyawaki

2002

J Americ Oil Chem Soc

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“…Novozym (<0.05% v/v), 97,98 lipase IM-20 (5% v/v). 99 Reductions in reaction rate were found with increasing hydrophobicity of solvents. 82 The principal drawback to the use of SCFs is the requirement of specialised equipment that can withstand high pressures which has an associated increase in cost on plant scale.…”

Section: Methodsmentioning

confidence: 97%

Recent trends in whole cell and isolated enzymes in enantioselective synthesis

Milner¹,

Maguire²

2012

Arkivoc

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Modern synthetic organic chemistry has experienced an enormous growth in biocatalytic methodologies; enzymatic transformations and whole cell bioconversions have become generally accepted synthetic tools for asymmetric synthesis. This review details an overview of the latest achievements in biocatalytic methodologies for the synthesis of enantiopure compounds with a particular focus on chemoenzymatic synthesis in non-aqueous media, immobilisation technology and dynamic kinetic resolution. Furthermore, recent advances in ketoreductase technology and their applications are also presented.Keywords: Biocatalysis, kinetic and dynamic kinetic resolution, Baker's yeast, ketoreductases General IntroductionAsymmetric synthesis is the preferential formation of one stereoisomer of a chiral target compound to another; when scientists at GlaxoSmithKline, AstraZeneca and Pfizer 1 examined 128 syntheses from their companies, they found as many as half of the drug compounds made by their process research and development groups are not only chiral but also contain an average of two chiral centres each. 2In 2006 just 25 % were derived from the chiral pool and over 50 % employed chiral technologies. 1In order to meet regulatory requirements enantiomeric purities of 99.5 % were deemed necessary by the FDA. 3 This is one of the biggest challenges which face chemists today, primarily due to the recognition of the fact that different enantiomers of the same compound can interact differently in biological systems. As a consequence, the production of single enantiomers instead of racemic mixtures has become an important process in the pharmaceutical and agrochemical industry. Several routes can lead to the desired enantiomer including transition metal-, [4][5][6] organo-5,7-10 and bio-catalysis [11][12][13][14][15] and these have been thoroughly reviewed in the literature. 16,17 2. Biocatalysis IntroductionBiocatalysis involves the use of enzymes or whole cells (containing the desired enzyme or enzyme system) as catalysts for chemical reactions. A timeline of historic events in biocatalysis and biotechnology is outlined in Table 1. [18][19][20] Reviews and Accounts Novel methodologies for discovering industrial enzymes based on genomic sequencing and phage display (discussed further in Section 1.3), 21,22 as well as highly effective optimisation tools based on chemical, physical and molecular biology approaches, 23 have improved the access to biocatalysts, increased their stability, and radically broadened their specificity. 24This greater availability of catalysts with superior qualities including the use of new bioengineering tools contributed significantly to the development of new industrial processes. Biocatalytic methodologies for organic synthesis were outlined by Woodley et al. in three categories: established, emerging and expanding chemistries as depicted in Figure 1. 25 Enzyme classesBy the late 1950s it had become evident that the nomenclature of enzymes without any guiding authority, in a period when the...

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“…Enzymatic interesterification is becoming a more attractive method to convert cheap oils such as olive pomace oil, soya bean oil, rape seed oil, lard, tallow, etc. to high-value-added products and modified fats Liua et al, 1997;Macrae, 1983;Miller et al, 1991;Pomier et al, 2007;Xu, 2003). Furthermore, enzymatic interesterification has milder reaction conditions and produces less waste than the chemical alternative.…”

Section: Enzymatic Conversionsmentioning

confidence: 99%