Selective Production of Diacylglycerols Through Glycerolysis by Ionic Liquid: 1‐Butyl‐3‐Methylimidazolium Imidazolide as Catalyst and Reaction Medium

Huang, Ying-Si; Gao, Yuying; Zhong, Nanjing

doi:10.1007/s11746-015-2650-3

Cited by 25 publications

(21 citation statements)

References 21 publications

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“…The lipid profile was determined according to our previous RP‐HPLC method . Quantification and identification of compounds were described in detail in one of our previous studies .…”

Section: Methodsmentioning

confidence: 99%

“…Production of DAG has been studied extensively during recent years. Enzymatic glycerolysis of TAG was one of the primary reaction routes for DAG production, as its high time‐space cost efficiency as well as minimal glycidol fatty acid ester formation at low temperatures . DAG selectivity was a concern in glycerolysis, as glycerolysis of TAG was a two‐step reversible reaction and DAG was the intermediate product .…”

Section: Introductionmentioning

confidence: 99%

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Enhancing the Catalytic Performance of Candida antarctica Lipase B by Immobilization onto the Ionic Liquids Modified SBA‐15

Zhong

Cai

et al. 2018

Euro J Lipid Sci & Tech

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In this study, mesoporous silica SBA‐15 is modified by imidazole based ionic liquids (IL) with three different side‐chain length of cations and two different anions. Prepared supports (IL‐SBA‐15) are characterized by small‐angle powder X‐ray diffraction (XRD), X‐ray photoelectron spectroscopy (XPS) as well as Fourier transform infrared (FT‐IR), and then used to immobilize Candida antarctica lipase B (CALB). The enzymatic properties of the obtained IL‐SBA‐15‐CALB are evaluated, and the catalytic selectivity toward diacylglycerols (DAG) production in glycerolysis of triacylglycerols (TAG) reaction is also studied. Compared with the parent SBA‐15 immobilized CALB (SBA‐15‐CALB), the IL modification gives a maximum improvement of enzymatic activity from 1855 to 5044 U g−1; in addition, the selectivity toward the diacylglycerols (DAG) production also increases, with the DAG/MAG ratio increasing from 3.72 to 11.99, and the DAG content increasing from 53.6 to 67.2 wt%. Practical applications: Immobilization of lipases facilitates the separation of products and the recovery of lipases for reuse. The present study shows that CALB immobilized on the IL modified SBA‐15 is potential for DAG production through glycerolysis, due to its considerable reusability as well as its high glycerolysis activity and selectivity toward DAG production, it could be considered for practical applications. Glycerolysis of corn oil catalyzed by ionic liquids modified SBA‐15 supports CALB to produce diacylglycerols. SBA‐15 is modified by ionic liquids, and then employed as carrier for Candida antarctica lipase B (CALB) immobilization. The obtained solid lipases are used to catalyze glycerolysis for diacylglycerols (DAG) production. Compared with the parent SBA‐15 immobilized CALB (SBA‐15‐CALB), ionic liquids modification gives a maximum improvement of enzymatic activity from 1855 to 5044 U g−1; in addition, the selectivity toward the DAG production is also increased, with the DAG/MAG ratio increasing from 3.72 to 11.99, and the DAG content increasing from 53.6 to 67.2 wt%.

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“…The lipid profile was determined according to our previous RP‐HPLC method . Quantification and identification of compounds were described in detail in one of our previous studies .…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enhancing the Catalytic Performance of Candida antarctica Lipase B by Immobilization onto the Ionic Liquids Modified SBA‐15

Zhong

Cai

et al. 2018

Euro J Lipid Sci & Tech

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“…Glycerolysis of TG toward DG has been shown to be promoted by enzymes [13,14,11], ionic liquids [15], alkali metal hydroxides, alkoxides and hydrides [16][17][18]. Enzymatic glycerolysis entails problems derived from the high cost of the enzymes and from the low reaction temperature that might not produce the 1,3-DG isomer in high yields.…”

Section: Introductionmentioning

confidence: 99%

Diglyceride-rich oils from glycerolysis of edible vegetable oils

2018

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“…The lipid profile was determined with Reverse‐phase high performance liquid chromatography, procedures were performed in accordance with our previous method (Huang et al, ). Compounds were identified and quantified based on our previous study (Zhong et al, ).…”

Section: Methodsmentioning

confidence: 99%

Enzymatic Production of Diacylglycerols from High‐Acid Soybean Oil

Zhong

Kou

Zhao

et al. 2019

J Americ Oil Chem Soc

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In this study, high-acid soybean oil, with acid values (Av) ranging from 10 to 50, was enzymatically deacidified for diacylglycerol (DAG) production. The effects of glycerol amounts were studied intensively. The glycerol amount could be calculated theoretically based on the Av of the raw oil (1 mol glycerol with 2 mol oleic acid to form 1 mol DAG, and 1 mol glycerol with 2 mol soybean oil to form 3 mol DAG). A total of 60-62% of DAG could be obtained and the free fatty acid (FFA) content was reduced to 0.36-0.66%. Increased glycerol did not lead to DAG content improvement. However, the glycerol amount based on just the deacidification theoretical calculation (1 mol glycerol with 2 mol oleic acid to form 1 mol DAG) was not feasible to reduce the FFA content. Moreover, Novozym 435 was rather stable in the present reaction procedure, no loss of activity was observed after 10 consecutive uses.

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Selective Production of Diacylglycerols Through Glycerolysis by Ionic Liquid: 1‐Butyl‐3‐Methylimidazolium Imidazolide as Catalyst and Reaction Medium

Cited by 25 publications

References 21 publications

Enhancing the Catalytic Performance of Candida antarctica Lipase B by Immobilization onto the Ionic Liquids Modified SBA‐15

Enhancing the Catalytic Performance of Candida antarctica Lipase B by Immobilization onto the Ionic Liquids Modified SBA‐15

Diglyceride-rich oils from glycerolysis of edible vegetable oils

Enzymatic Production of Diacylglycerols from High‐Acid Soybean Oil

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