High-yield synthesis of wax esters catalysed by modified Candida rugosa lipase

Guncheva, Maya; Zhiryakova, Diana

doi:10.1007/s10529-007-9554-8

Cited by 26 publications

(7 citation statements)

References 15 publications

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“…A similar route towards wax esters was developed by Guncheva and Zhiryakova. 174 An interesting and somewhat sophisticated application of immobilised enzymes for the production of renewables is the synthesis of phytosterol esters. Zheng et al immobilised Candida rugosa lipase on mixed-mode silica particles via hydrophobic and cation-exchange interaction, in order to catalyse the esterification of phytosterols to free fatty acids (see Scheme 5).…”

Section: Non-fuel Usages Of Fats and Oil Productsmentioning

confidence: 99%

Immobilised enzymes in biorenewables production

et al. 2013

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Oils, fats, carbohydrates, lignin, and amino acids are all important raw materials for the production of biorenewables. These compounds already play an important role in everyday life in the form of wood, fabrics, starch, paper and rubber. Enzymatic reactions do, in principle, allow the transformation of these raw materials into biorenewables under mild and sustainable conditions. There are a few examples of processes using immobilised enzymes that are already applied on an industrial scale, such as the production of High-Fructose Corn Syrup, but these are still rather rare. Fortunately, there is a rapid expansion in the research efforts that try to improve this, driven by a combination of economic and ecological reasons. This review focusses on those efforts, by looking at attempts to use fatty acids, carbohydrates, proteins and lignin (and their building blocks), as substrates in the synthesis of biorenewables using immobilised enzymes. Therefore, many examples (390 references) from the recent literature are discussed, in which we look both at the specific reactions as well as to the methods of immobilisation of the enzymes, as the latter are shown to be a crucial factor with respect to stability and reuse. The applications of the renewables produced in this way range from building blocks for the pharmaceutical and polymer industry, transport fuels, to additives for the food industry. A critical evaluation of the relevant factors that need to be improved for large-scale use of these examples is presented in the outlook of this review.

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Section: Non-fuel Usages Of Fats and Oil Productsmentioning

confidence: 99%

Immobilised enzymes in biorenewables production

et al. 2013

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“…The driving force for this research has been the possibility of preparing esters which mimics the naturally occurring waxes of commercially interest. This is due to the depletion and expensive supply of naturally occurring wax esters such as beeswax, jojoba oil, and sperm whale oil [9]. Alternative production process using renewable resources such as palm oil could be developed.…”

Section: Introductionmentioning

confidence: 99%

Optimization and kinetic study on the synthesis of palm oil ester using Lipozyme TL IM

Basri

Kassim

Mohamad

et al. 2013

Journal of Molecular Catalysis B: Enzymatic

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a b s t r a c tEnzymatic synthesis of palm oil esters (POE) was carried out via alcoholysis of palm oil (PO) and oleyl alcohol (OA) catalyzed by Lipozyme TL IM. The optimum reaction conditions were: temperature: 60 • C; enzyme load: 24.7 wt%; substrate ratio: 1:3 (PO/OA), impeller speed: 275 rpm and reaction time: 3 h. At the optimum condition, the conversion of POE was 79.54%. Reusability study showed that Lipozyme TL IM could be used for 5 cycles with conversion above 50%. The alcoholysis reaction kinetic follows the Ping-Pong Bi-Bi mechanism characterized by the V max , K m(PO) , and K m(OA) values of 32.7 mmol/min, 0.3147 mmol/ml and 0.9483 mmol/ml, respectively. The relationship between initial reaction rate and temperature was also established based on the Arrhenius law.

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“…[7] In addition, as biolubricants they exhibit excellent performance. Enzymatic processes [11][12][13] are still under development today, and very few companies are interested in this process. However, their isolation from sperm whales is currently prohibited.…”

Section: Introductionmentioning

confidence: 99%

“…For this purpose enzymatic or chemical processes using a variety of vegetable oils are the subject of researches. Enzymatic processes are still under development today, and very few companies are interested in this process. Therefore, homogenous or heterogeneous‐catalyzed chemical synthetic methods (esterification, transesterification, and alcoholysis) maintain its popularity.…”

Section: Introductionmentioning

confidence: 99%

Improved Sustainable Ionic Liquid Catalyzed Production of Symmetrical and Non‐Symmetrical Biological Wax Monoesters

Yıldırım

Mudaber

Öztürk

2018

Euro J Lipid Sci & Tech

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Biological wax esters are important commercial products used in various industrial and medicinal fields. These valuable compounds can be synthesized via several chemical and enzymatic reactions which have some advantages and more disadvantages. In particular, many strong acid catalysts cause undesirable structural changes in unsaturated fatty acids molecules. In the present study, easily accessible 1‐hexadecyl‐3‐sulfoimidazolium chloride as an ionic liquid is screened as a mild Brønsted acid metal free catalyst for the chemical esterification, or transesterification, of equimolar amounts of long chain fatty acids or fatty acid methyl esters, respectively, with fatty alcohols in a solventless medium. The various parameters affecting the yield of the wax ester are optimized, catalyst reuse studies, and large scale synthesis are also carried out. According to this alternative practical and green process, a series of wax esters (17 examples) are produced readily in good to excellent yields. There is no undesirable geometric cis‐trans isomerization in unsaturated fatty acids under the reaction conditions used. The catalyst is also quite effective when triglycerides are converted directly to the wax esters via transesterification reaction. Practical Applications: With an effortless and environmentally friendly method developed in this study, various wax esters can be synthesized as valuable industrial materials. In order to synthesis these esters, there is not any restriction for starting compounds. The most important aspect of the developed procedures is that metallic or strong aggressive acidic catalysts are not used compared to existing procedures. It is possible to carry out large‐scale syntheses of esters with high yields. In the present study, a series of industrial and medical important wax esters are synthesized from renewable sources in a solvent‐free environment using IL‐catalyzed environmentally friendly methods.

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High-yield synthesis of wax esters catalysed by modified Candida rugosa lipase

Cited by 26 publications

References 15 publications

Immobilised enzymes in biorenewables production

Immobilised enzymes in biorenewables production

Optimization and kinetic study on the synthesis of palm oil ester using Lipozyme TL IM

Improved Sustainable Ionic Liquid Catalyzed Production of Symmetrical and Non‐Symmetrical Biological Wax Monoesters

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