Quantitative enzymatic production of 1,6‐diacyl sorbitol esters

Arcos, José A.; Bernabé, Manuel; Otero, Cristina

doi:10.1002/(sici)1097-0290(19981005)60:1<53::aid-bit6>3.0.co;2-#

Cited by 29 publications

(10 citation statements)

References 16 publications

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“…4,12 It is also noteworthy that the percentage of conversion decreased for all the sorbitol to stearic acid molar ratios after 24 h (Table II). This could have been caused by water absorption by the system due to long reaction times.…”

Section: Scheme 2 Effect Of Molar Ratio Of Sorbitol and Stearic Acidmentioning

confidence: 86%

“…lipase. 12 Arcos et al 4 have used acetone as solvent for the synthesis of 1,6-diacylsorbitol derivatives.…”

Section: Effect Of Organic Solventsmentioning

confidence: 99%

“…Among these, the fatty acid esters of sorbitol are the second largest class of carboxylic acid esters employed as surfactants. 4 Their preparation by purely chemical means requires high-energy consumption (acid catalysis and reaction temperatures of 225-250 °C) and results in the formation of toxic and colored by-products. Even preferential acylation of primary over secondary hydroxyl groups can rarely be carried out efficiently with free sugars or sugar alcohols.…”

Section: Introductionmentioning

confidence: 99%

“…Even preferential acylation of primary over secondary hydroxyl groups can rarely be carried out efficiently with free sugars or sugar alcohols. [3][4][5] New enzymatic methods involving lipases and proteases are being employed in micro-aqueous/organic media for synthesis of such esters.…”

Section: Introductionmentioning

confidence: 99%

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Novel biocatalytic esterification reactions on fatty acids: synthesis of sorbitol 1(6) - monostearate

Gulati¹,

Arya²,

Malhotra³

et al. 2003

Arkivoc

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Dedicated to Professor Sukh Dev on his 80th birthday (received 16 Jan 03; accepted 06 May 03; published on the web 08 May 03) AbstractAspergillus terreus lipase has exhibited novel capability of catalyzing esterification reaction between fatty acids (C 4 -C 18 ) and primary, secondary and tertiary monohydric alcohols. Although, the lipase efficiently catalyzed the esterification of saturated stearic acid (C 18:0 ), it failed to accept the monounsaturated oleic acid (C 18:1 ) as the substrate which is also a C 18 acid, but has a double bond. Thus, this enzyme has a great potential to be used as a selective catalyst for the separation of almost identical saturated and unsaturated fatty acids in their mixtures. Extending this work, highly efficient and regioselective conversion of sorbitol to its 1(6) -monostearate has been achieved by Aspergillus terreus lipase -mediated esterification in n-hexane. Ninety four per cent conversion to the ester was achieved in 12 h on optimizing four physico-chemical factors, i.e. molar ratios of substrates, temperature, solvent and water activity. Aspergillus terreus lipase immobilized on Accurel was efficient in the synthesis of sorbitol stearate and was reused three times without any significant decline in its activity, yields were further enhanced to 96 % on using the immobilized enzyme.

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Section: Scheme 2 Effect Of Molar Ratio Of Sorbitol and Stearic Acidmentioning

confidence: 86%

“…lipase. 12 Arcos et al 4 have used acetone as solvent for the synthesis of 1,6-diacylsorbitol derivatives.…”

Section: Effect Of Organic Solventsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Novel biocatalytic esterification reactions on fatty acids: synthesis of sorbitol 1(6) - monostearate

Gulati¹,

Arya²,

Malhotra³

et al. 2003

Arkivoc

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“…Then the solvent was removed by evaporation in a vacuum oven for 3 h at 40 °C. Purification of the esters was accomplished by column chromatography using a column (1.6 cm diameter, 50 cm height) packed with silica gel (25 g of silica gel in 100 ml of chloroform) 17. The flow rate was adjusted to 1.3 ml min −1 using a peristaltic pump (EYELA microtube pump M‐3, Rikakikai Co, Ltd, Tokyo, Japan).…”

Section: Methodsmentioning

confidence: 99%

Production and characterisation of enzymatically produced lauric acid esters of fructose

Şekeroğlu¹,

Fadı́loğlu

İbanoğlu

2002

J Sci Food Agric

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Lauric acid esters of fructose were produced using immobilised lipase (EC 3.1.1.3; Novozym 435). A molecular sieve was used to shift the reaction towards the synthesis. The mono-, di-and higher esters of lauric acid with fructose were obtained and analysed qualitatively and quantitatively by highpressure liquid chromatography (HPLC). At a 5:1 molar ratio of lauric acid to fructose the amounts of monoester, diester and higher esters produced were 37, 53 and 98 mg respectively after 96 h of reaction time. After purification of the products by column chromatography the hydrophile/lipophile balance (HLB) values of fructose monolaurate and fructose dilaurate were found to be 8.95 and 5.3 respectively and their critical micelle concentration (CMC) values were calculated as 7.20 Â 10 À5 and 6.40 Â 10 À5 M respectively. The CMC values of esters obtained from the conductivity curve and the surface tension curve were significantly (P < 0.05) similar to each other. It was found that when the concentration of surfactant was increased from 0.25 to 0.50% (w/v), stabilisation of the emulsion also increased. Fructose dilaurate showed better stability than the other esters. Separation of the phases reached 70% within 30 h for the emulsion prepared with 0.50% (w/v) of this ester.

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Continuous enzymatic esterification of glycerol with (poly)unsaturated fatty acids in a packed-bed reactor

Arcos

Garcı́a

Hill

2000

Biotechnol. Bioeng.

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Enzymatic synthesis of mono‐, di‐, and triacyglycerols from (poly)unsaturated fatty acids (linoleic, oleic, and conjugated linoleic acids) has been studied as a solvent‐free reaction in a packed‐bed reactor containing an immobilized lipase from Mucor miehei. The extents of the esterification reactions of interest are primarily determined by the molar ratio of glycerol to fatty acid because the presence of excess glycerol as a immiscible phase is responsible for reducing the activity of the water produced by the esterification reactions. For molar ratios of fatty acid to glycerol of less than 1.5, the percentage of the fatty acid esterified decreases quasi‐linearly with an increase in this molar ratio. By appropriate manipulation of the fluid‐residence time, one can control the relative proportions of the various acylglycerols in the effluent stream. At the outlet of the reactor, one observes excellent spontaneous separation of the glycerol and acylglycerol/fatty acid phases. At 50°C and a fluid residence time of 1 hour, as much as 90% of the fatty acid can be esterified when the molar ratio of fatty acid to glycerol is 0.33 or less.

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Quantitative enzymatic production of 1,6‐diacyl sorbitol esters

Cited by 29 publications

References 16 publications

Novel biocatalytic esterification reactions on fatty acids: synthesis of sorbitol 1(6) - monostearate

Novel biocatalytic esterification reactions on fatty acids: synthesis of sorbitol 1(6) - monostearate

Production and characterisation of enzymatically produced lauric acid esters of fructose

Continuous enzymatic esterification of glycerol with (poly)unsaturated fatty acids in a packed-bed reactor

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