- Propylsulfonic acid functionalized mesoporous silica catalysts for esterification of fatty acids
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The catalytic properties of 3 types of mesoporous silica SBA-15 (rope, rod and fiber), with 9.2 nm or 12.1 nm large mesopores, were examined with respect to their morphology and pore size. Commercially available Amberlyst-15 and the small pore sized MCM-41 were used for comparison. The catalysts were prepared by functionalization of the silica supports with propylsulfonic acid (Pr-SO3H) using post-synthesis grafting with 3-mercaptopropyltrimethoxysilane as a propyl-thiol precursor. All materials remained in a well-ordered hexagonal mesoporous structure after Pr-SO3H functionalization. The performance of the Pr-SO3H-functionalized mesoporous silicas was evaluated in terms of their catalytic activity in the esterification of oleic acid with short (methanol) and long (glycerol) chain alcohols, i.e., to test the effect of the pore size on the substrate conversion and product yield. The synthesized catalysts were highly active and the product composition could be tuned by selective choice of the mesopore size. The Pr-SO3H-functionalized rope-shaped SBA-15 gave the highest catalytic activity (in terms of the highest methyl oleate and triglyceride yields and oleic acid conversion level), which was higher than that obtained with the commercial Amberlyst-15 catalyst. A high acid amount, large specific surface area and a suitable pore size are the likely reasons for the high yield gained by Pr-SO3H-functionalized rope-shaped SBA-15 silica.
- Jeenpadiphat, Sirima,Bj?rk, Emma M.,Odén, Magnus,Tungasmita, Duangamol Nuntasri
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- Synthesis of the structured lipid 1,3-dioleoyl-2-palmitoylglycerol from palm oil
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Human milk fat contains 20-25% palmitic acid (16:0) and 30-35% oleic acid (18:1). More than 60% of the palmitic acid occurs at the sn-2 position of the glycerol backbone. Palm oil is a rich source of both palmitic and oleic acids. The structured lipid 1,3-dioleoyl-2-palmitoylglycerol (OPO) is an important ingredient in infant formula. OPO was synthesized from palm oil by a three-step method. In the first step, low-temperature fractionation was applied to palm oil FA, yielding a palmitic acid-rich fraction (87.8%) and an oleic acid-rich fraction (96%). The palmitic acid content was further increased to 98.3% by transforming palmitic acid into ethyl palmitate. In the second step, esterificalion of ethyl palmitate and glycerol catalyzed by lipase Novozym 435 under vacuum (40 mm Hg) was employed for the synthesis of tripalmitin. Finally, OPO was obtained by the reaction of tripalmitin with oleic acid catalyzed by Lipase IM 60. In this final step, the TAG content in the product acylglycerol mixture was 97%, and 66.1 % oleic acid was incorporated into TAG. Analysis of the FA composition at the sn-2 position of TAG showed 90.7 mol% of palmitic acid and 9.3 mol% of oleic acid. OPO content in the product TAG was ca. 74 mol%. Thus, an efficient method was developed for the synthesis of OPO from palm oil.
- Chen, Ming-Lung,Vali, Shaik Ramjan,Lin, Jih-Yao,Ju, Yi-Hsu
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- RP-HPLC/MS-APCI analysis of branched chain TAG prepared by precursor-directed biosynthesis with rhodococcus erythropolis
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Reversed phase liquid chromatography-atmo-spheric pressure chemical ionization mass spectrometry (RP-HPLC/MS-APCI) was used to analyze both synthetic triacylglycerols (TAG) having 1-3 branched fatty acids (FA) in the molecule, and natural TAG prepared by precursor directed biosynthesis from valine, leucine and iso-leucine and the corresponding branched short-chain acids in cultivations of Rhodococcus erythropolis. The technique made it possible to identify and quantify TAG differing in a single branched-chain FA. Altogether 11 TAG were synthesized, out of which 8 were synthesized stereospecifi-cally. Branched-and straight-chain-TAG were separated and identified while TAG differing only in iso or anteiso FA could not be separated. The APCI mass spectra of iso-, anteiso-and straight-chain TAG were completely identical. The natural material was found to contain 19 TAG having at least one branched FA. Cultivation on six different substrates showed, apart from the presumed and common incorporation of precursors to iso-even, iso-odd and anteiso FA, also some unusual features such as an increase in the content of odd-FA after the addition of Val (attributed to catabolism of Val to propionate) or the appearance of branched monounsaturated FA. The two-sample paired t test, when applied to the TAG, showed that only the pair Val and isobutyrate differ in incorporation into FA-see, e.g. proportions of M/M/O and brM/brM/O (1.2:1.2 and 1.9:1.2, respectively). Also, incorporation of Val (isobu-tyrate) yielded only TAG having two branched FA in the molecule, whereas Leu and Ile (isovalerate and 2-methyl-butyrate) gave only TAG with a single branched FA in the molecule. AOCS 2010.
- Schreiberová, Olga,Krulikovská, Tereza,Sigler, Karel,?ejková, Alena,?ezanka, Tomá?
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- Optimization of Candida sp. 99-125 lipase catalyzed esterification for synthesis of monoglyceride and diglyceride in solvent-free system
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Esterification of glycerol and oleic acid catalyzed by lipase Candida sp. 99-125 was carried out to synthesize monoglyceride (MAG) and diglyceride (DAG) in solvent-free system. Beta-cyclodextrin as an assistant was mixed with the lipase powder. Six reaction variables, initial water content (0-14 wt% of the substrate mass), the glycerol/oleic acid molar ratio (1:1-6:1), catalyst load (3-15 wt% of the substrate mass), reaction temperature (30-60 °C), agitator speed (130-250 r/min) and beta-cyclodextrin/lipase mass ratio (0-2) were optimized. The optimal conditions to the synthesis of MAG and DAG were different: the optimal glycerol/oleic acid molar ratio, beta-cyclodextrin/lipase mass ratio, catalyst load and reaction temperature were 6:1, 0, 5%, 50 °C for MAG, and 5:1, 1.5, 10%, 40 °C for DAG, respectively. The optimal water content and agitator speed for both MAG and DAG were 10% and 190 r/min, respectively. Under the optimal conditions, 49.6% MAG and 54.3% DAG were obtained after 8 h and 4 h, respectively, and the maximum of 81.4% MAG plus DAG (28.1% MAG and 53.3% DAG) was obtained after 2 h under the DAG optimal condition. Above 90% purity of MAG and DAG can be obtained by silica column separation.
- Zhao, Yanjun,Liu, Junfeng,Deng, Li,Wang, Fang,Tan, Tianwei
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- Model studies and the ADMET polymerization of soybean oil
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Grubbs' ruthenium catalyst 2 has been employed in model studies of the acyclic diene metathesis (ADMET) polymerization of soybean oil. In the presence of 0.1 mol% of catalyst 2, the ADMET polymerization of ethylene glycol dioleate afforded the isomerized (E)-dioleate (27%), dimer (18%), trimer (13%), tetramer (7%), pentamer (5%), hexamer (4%), heptamer (4%), and 9-octadecene (21%). Only a trace of any intramolecular cyclized product was formed. Under the same conditions, glyceryl trioleate underwent ADMET polymerization to produce dimer, trimer, tetramer, pentamer, and monocyclic oligomers, with monocyclic oligomers predominating. The high number of repeat units in the monocyclic oligomers (n ? 6, 10, and 21) indicates that cross-linking occurs readily in this process. Based on our model system studies, we have examined the ADMET polymerization of soybean oil and succeeded in producing polymeric materials ranging from sticky oils to rubbers.
- Tian, Qingping,Larock, Richard C.
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- FUNCTIONALISED MATERIALS, PROCESS FOR THE PRODUCTION AND USES THEREOF
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The invention relates both to processes for the production of functionalised materials containing alkyl sulfonic acids groups and their use as heterogeneous catalysts. The invention also relates to precursors of these new products and new organopolysiloxane sulfonic acids.
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Paragraph 0041; 0055
(2015/04/22)
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- PROCESS FOR PREPARING BIODEGRADABLE LUBRICANT BASE OILS
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The invention discloses an improved process for preparing fatty acid esters with 100 mol % selectivity suitable as biodegradable lubricant base oils, comprising contacting a fatty compound with an alcohol in presence of a solid, phosphonate catalyst having molecular formula: M(X)2-nYn.mH2O where X refers to phenyl phosphonate, Y refers to HPO42? or HPO32?, M refers to a metal or metalloid ion preferably taken from the group consisting of Zr, Zn, Cd, Al, Sn, La and Ce, the value of n varies from 0.2 to 1.8 and the value of m varies from 0 to 5, wherein the fatty compound is a fatty acid or fatty acid methyl or ethyl ester or vegetable oil or animal fat or their mixture thereof and alcohol is a monohydric alcohol with 6 to 22 carbon atoms or a polyol with at least two hydroxyl groups.
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Paragraph 0074; 0091
(2015/06/03)
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- Zirconium phenyl phosphonate phosphite as a highly active, reusable, solid acid catalyst for producing fatty acid polyol esters
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The application of zirconium phenyl phosphonate phosphite (ZrPP) as a solid acid catalyst for producing polyol esters by esterification of glycerol or trimethylolpropane with a fatty acid (C8-C18.1) is reported for the first time. ZrPP exhibits high catalytic activity and in particular, (di + tri) esters selectivity (92.3 mol%). These esters of polyols are known for their application as biolubricants. The catalyst prepared using phosphorous acid to phenyl phosphonic acid molar ratio of 3:1 was found superior. The influence of process parameters on activity and selectivity of the catalyst was investigated. ZrPP was reusable in at least three recycling experiments. Hydrophobicity due to exposed phenyl groups on the surface is the possible cause for superior esterification activity of this novel, solid catalyst.
- Varhadi, Poonam,Kotwal, Mehejabeen,Srinivas
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p. 129 - 136
(2013/07/26)
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- Synthesis of monoglycerides by esterification of oleic acid with glycerol in heterogeneous catalytic process using tin-organic framework catalyst
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Selective synthesis of monoglycerides by esterification of glycerol with fatty acids is a difficult reaction because of immiscibility of reagents and the formation of di- and tri-glyceride by-products. In this work a heterogeneous catalytic process was conceived in which the reactant mixture was homogenized using tert-butanol solvent. Candidate catalysts were screened in the reaction of oleic acid with glycerol. While under such reaction conditions zeolites were rather inactive, metal-organic frameworks and, especially, tin-organic frameworks were found promising. A tin-organic framework (Sn-EOF) was most active and achieved ≥98 % monoglyceride selectivity at 40 % conversion in catalyzing esterification of oleic acid with glycerol at a low reaction temperature of 150 C. Leaching of tin from Sn-EOF catalyst was suppressed by limiting the amount of oleic acid in the starting mixture. Characterization of the acid sites of Sn-EOF by pyridine-chemisorption and FTIR revealed Lewis acidity to be responsible for the catalytic activity.
- Wee, Lik H.,Lescouet, Tristan,Fritsch, Julia,Bonino, Francesca,Rose, Marcus,Sui, Zhijun,Garrier, Eva,Packet, Dirk,Bordiga, Silvia,Kaskel, Stefan,Herskowitz, Moti,Farrusseng, David,Martens, Johan A.
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p. 356 - 363
(2013/05/21)
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- PALM OIL ENRICHED IN UNSATURATED FATTY ACIDS
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A process for producing a food oil containing at least 50% monounsaturated fatty acids from palm oil is disclosed. Fatty acids are released from palm oil glycerides, such as by fat-splitting. The free fatty acids (FFA) are separated to obtain a fraction enriched in unsaturated palm fatty acid. This fraction is subject to a condensation reaction with glycerol to form an oil comprising mainly triglycerides (triacylglycerols). The condensation reaction is catalyzed by an enzyme.
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Paragraph 0067; 0068
(2013/06/06)
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- MgO-based catalysts for monoglyceride synthesis from methyl oleate and glycerol: Effect of Li promotion
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The synthesis of monoglycerides (glyceryl monooleates) by heterogeneously catalyzed glycerolysis of an unsaturated fatty acid methyl ester (methyl oleate) was studied on MgO and Li-promoted MgO catalysts. Several MgO-based catalysts with different Li loadings were prepared by incipient wetness impregnation and characterized by XRD, N2 physisorption, and FTIR and TPD of CO 2 among other techniques. Promotion of MgO with lithium, a basic promoter, affected the textural and structural properties of the resulting oxides so that more crystalline MgO phases with decreased surface area were obtained at increasing Li contents. Furthermore, the addition of Li generated new strong base sites because of formation of dispersed surface Li2O species, and thereby increased the total base site density of parent MgO. Li-containing MgO catalysts efficiently promoted the glycerolysis reaction, achieving high monoglyceride yields (70-73%) at 493 K. The initial monoglyceride formation rate increased linearly with the Li content on the sample following the enhanced overall catalyst base strength. Although conversions at the end of the run were ≈100% for all the catalysts, the monoglyceride selectivity slightly decreased with the Li loading, probably as a consequence of the less surface affinity for glycerol adsorption that facilitates competing monoglyceride re-adsorption and transformation to diglycerides by consecutive glycerolysis or disproportionation reactions.
- Ferretti,Apesteguía,Di Cosimo
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experimental part
p. 146 - 153
(2012/02/01)
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- Production of acylglycerol esters
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The present invention relates to the production of oil and fat containing acylglycerol esters including diacylglycerols, medium-chain and long-chain fatty acid triacyglycerols comprising esterification reaction between an acyl group donor and an acyl group acceptor in the presence of a heterogeneous chemical catalyst consisting of an ion-exchange resin preparation to obtain a reaction fluid that is further subjected to dehydration and at least one separation method, thus producing diacylglycerols and/or medium-chain and long-chain fatty acid triacyglycerols at a high yield in a short period of time.
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Page/Page column 11-12
(2011/12/22)
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- Glycerol acyl-transfer kinetics of a circular permutated Candida antarctica lipase B
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Triacylglycerols containing a high abundance of unusual fatty acids, such as γ-linolenic acid, or novel arylaliphatic acids, such as ferulic acid, are useful in pharmaceutical and cosmeceutical applications. Candida antarctica lipase B (CALB) is quite often used for non-aqueous synthesis, although the wild-type enzyme can be rather slow with bulky and sterically hindered acyl donor substrates. The catalytic performance of a circularly permutated variant of CALB, cp283, with various acyl donors and glycerol was examined. In comparison to wild-type CALB, butyl oleate and ethyl γ-linolenate glycerolysis rates were 2.2- and 4.0-fold greater, respectively. Cp283 showed substrate inhibition by glycerol, which was not the case with the wild-type version. With either ethyl ferulate or vinyl ferulate acyl donors, cp283 matched the performance of wild-type CALB. Changes in active site accessibility resulting from circular permutation led to increased catalytic rates for bulky fatty acid esters but did not overcome the steric hindrance or energetic limitations experienced by arylaliphatic esters.
- Laszlo, Joseph A.,Yu, Ying,Lutz, Stefan,Compton, David L.
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scheme or table
p. 175 - 180
(2012/07/01)
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- Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides
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A trifluoroacetate-catalyzed opening of the oxirane ring of glycidyl derivatives bearing allylic acyl or alkyl functionalities with trifluoroacetic anhydride (TFAA), provides an efficient entry to configurationally homogeneous 1(3)-acyl- or 1(3)-O-alkyl-sn-glycerols. Selective introduction of tert-butyldimethylsilyl- (TBDMS), or triisopropylsilyl- (TIPS) transient protections at the terminal sites within these key intermediates secures 1(3)-acyl- or 1(3)-O-alkyl-3(1)-O-TBDMS (or TIPS)-sn-glycerols as general bifunctional precursors to 1,2(2,3)-diacyl-, 1(3)-O-alkyl-2-acyl- and 1,3-diacyl-sn-glycerols and hence triester isosters. Incorporation of a requisite acyl residue at the central carbon of the silylated synthons with a subsequent Et3N·3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment at the stereogenic C2-centre of the monosilylated glycerides; (ii) replacement of the silyl moiety by a short- or long-chain carboxylic acid residue by means of the acylating agent: tetra-n-butylammonium bromide (TBABr)-carboxylic acid anhydride (CAA)-trimethylsilyl bromide (TMSBr); and (iii) removal of the trichloroacetyl replacement, provides pure 1,3-diacyl-sn-glycerols. The TBABr-CAA-TMSBr reagent system allows also a one-step conversion of 1,2-diacylglycerol silyl ethers into homochiral triglycerides with predefined asymmetry and degree of unsaturation. These compounds can also be accessed via a two-step one-pot approach where the trichloroacetyl derivatives of 1,2(2,3)- or 1,3-diacyl-sn-glycerols serve as triester building blocks for establishing the third ester bond at preselected C3(1)- or C2-positions within the glycerol skeleton at the very last synthetic stage. In all instances, the target compounds were produced under mild conditions, in high enantiomeric purity, and in practically quantitative yields. The Royal Society of Chemistry 2007.
- Stamatov, Stephan D.,Stawinski, Jacek
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p. 3787 - 3800
(2008/10/09)
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- Widely useful DMAP-catalyzed esterification under auxiliary base- and solvent-free conditions
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With regard to atom economy and E-factor, catalytic condensation of carboxylic acids with equimolar amounts of alcohols is the most desirable. Although several highly active dehydration catalysts have been reported, more efficient alternatives are still strongly needed because the dehydrative esterification of tertiary alcohols, phenols, acid-sensitive alcohols, amino acids, and hardly soluble alcohols has never proceeded satisfactorily. Here we report new insights into the classical DMAP-catalyzed acylation of alcohols: surprisingly, only a 0.05-2 mol % of DMAP can efficiently promote acylation of alcohols with acid anhydrides under auxiliary base- and solvent-free conditions to give the corresponding esters in high yields. Furthermore, we achieved the recovery and reuse of commercially available polystyrene-supported DMAP without using any solvents. These serendipitous findings provide widely useful and environmentally benign esterification methods, which might be more practical and reliable than catalytic dehydrative condensation methods, in particular, for the less reactive alcohols which hardly condense with carboxylic acid directly.
- Sakakura, Akira,Kawajiri, Kimio,Ohkubo, Takuro,Kosugi, Yuji,Ishihara, Kazuaki
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p. 14775 - 14779
(2008/09/17)
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- Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
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1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.
- Rosu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Yamane, Tsuneo
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p. 839 - 843
(2007/10/03)
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- Enzyme, medium, and reaction engineering to design a low-cost, selective production method for mono- and dioleoylglycerols
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The selective enzymic production of mono- and diolein (MO, DO) was optimized at high yields. A comparative study of the following distinct enzymic reactions was conducted: ethyl oleate glycerolysis, triolein (TO) glycerolysis, and direct esterification. Solvent-free systems were compared with media that contained different solvents. Native, modified (with polyethylene glycol), and immobilized lipases were used. Mechanical resistance, the support effect on enzyme and glycerol dispersion and on process reproducibility, and hydrophilicity of the support were considered in the process optimization. We report the use of an immobilized lipase on an inorganic support (Celite), which has high activities in both solid-phase glycerolysis (99% reaction conversion) and esterification (100% conversion). The optimum conditions for the distinct reactions were compared by considering their selectivities, conversions, yields, and cost of the substrates. We found less costly and more selective processes in the absence of solvents for glycerolysis of triolein and direct esterification. Although glycerolysis was the most interesting process to produce diolein, esterification was better for monoolein preparation with this biocatalyst. The esterification reaction yielded 93 wt% of MO, in the absence of either TO or oleic acid (OA), at low cost because of the 100% reaction conversion. Similar costs of the substrates (10.6 and 10.1 $/g) were necessary to obtain 67 and 80 wt% of DO in esterification and glycerolysis, respectively. The glycerolysis conversion was 96%. In esterification, the product mixture was impure, with a high amount of residual OA due to the low conversion (59%). The high activity of PSL-Celite in these solid-phase reactions has an advantage over the reactions with nonimmobilized lipases due to the ease of enzyme recovery. The absence of organic solvents reduces the need for solvent removal from the reaction mixtures.
- Arcos,Otero
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p. 673 - 682
(2007/10/03)
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- Characteristics of Lipase Modified with Water-soluble Acylating Reagents and Its Esterification Ability
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Lip was modified with various hydrophobic groups, such as Z, Boc, lauroyl, and palmitoyl, using water-soluble acylating reagents.The chemical modification enhanced the dispersibility of Lip in organic solvents, and changed the substrate selectivity, which depends on the length of the carbon chain of triglycerides in hydrolytic reactions.As for the synthesis of triglycerides, Z-modified Lip catalyzed this reaction faster than unmodified Lip.Z-, Boc-, and fatty acid-modified Lips also catalyzed diverse esterification reactions including that of ethyl eicosapentaenoate, lactose oleate, and cholesterol oleate, and the yields of these reactions increased depending on the carbon number of the introducing group.
- Takahashi, Yoshinori,Tanaka, Kaori,Murakami, Mototake,Kawanari, Masami,Kawasaki, Yoshihiro,et al.
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p. 809 - 812
(2007/10/02)
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- 1H-Nuclear magnetic resonance spectroscopic studies of saturated, acetylenic and ethylenic triacylglycerols
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The 1H-NMR spectroscopic properties of 15 synthetic homologous saturated triacylglycerols of type AAA and 16 mixed saturated triacylglycerols of type ABA and AAB have been studied. Triacylglycerols containing short-chain fatty acids (2:0-6:0) are readily identified. Triacylglycerols containing medium- and long-chain fatty acid components are not differentiated. From the analysis of 19 acetylenic triacylglycerols of type AAA, ABA and AAB (containing positional isomers of acetylenic fatty acids), it is only possible to characterize triacylglycerols with acyl groups containing the acetylenic bond at the Δ2-Δ5 position. 1H-NMR analysis could not confirm the positions (α- or β-acyl) of the acetylenic acids in mixed triacylglycerols. In the study of 22 ethylenic triacylglycerols of type AAA containing positional isomers of (Z)- or (E)-ethylenic acids, molecules containing an ethylenic bond in the Δ2 position of the acyl chains were readily characterized, as the ethylenic protons in the α- and β-acyl chains were fully resolved. Triacylglycerols containing an unsaturated center at the position were characterized by the shifts of the 2-H protons. The spectra of the remaining triacylglycerol molecules were very similar and the position of the ethylenic system could not be determined by this technique.
- Lie Ken Jie, Marcel S.F.,Lam
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p. 155 - 171
(2007/10/03)
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- Water-based pesticidal composition
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A water-based pesticidal composition contains 100 weight parts of substantially water-insoluble pesticide and 1.7-200 weight parts of a surface active agent. The surface active agent contains Component A and Component B at weight ratio of A/B=80/20-20/80. Component A is polyalkylene glycol ether derivative of polyethylene polyamine shown by the following general formula and having molecular weight of 20,000-100,000: STR1 where R1, R2, R3 and R4 are selected from the group consisting of hydrogen, alkyl group with 1-4 carbon atoms, alkanoyl group with 2-18 carbon atoms, alkenoyl group with 2-18 carbon atoms and polyoxyalkylene glycol group containing oxyethyne unit and oxypropylene unit at weight ratio of (oxyethyne unit/oxypropylene unit=)100/0-50/50, at least one of R1, R2, R3 and R4 being the polyoxyalkylene glycol group, and n is an integer 2-250. Component B includes one or more selected from the group consisting of partial esters of polyhydric alcohol selected from sorbitol, sorbitan, glycerine and polyglycerine and unsaturated aliphatic acid with 16-22 carbon atoms and ethylene oxide adducts of such partial esters.
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- Fat Hydrolysis and Esterification by a Lipase from Humicola lanuginosa
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The hydrolysis and esterification by a thermostable lipase from Humicola lanuginosa No. 3 were investigated.Both reactions occurred readily at temperatures between 45-50 deg C.Esterification by the enzyme with glycerol was observed to be specific towards fatty acids with carbon numbers of C12-C18.Lauric acid esters with different alcohols such as primary alcohols, terpene alcohols, etc., were also synthesized readily.Esterification by the enzyme was adversely affected by the water content (optimum, ca. 7percent), however, the hydrolysis rate increased rapidly with increasing water content (optimum, ca. 60percent).The enzyme showed increased activity in organic solvent-aqueous reaction systems.Nevertheless, hydrolysis in complete organic phase reactions was found not to be feasible.Hydrolysis at a higher temperature (50 or 55 deg C) in a solvent free phase was almost the same as that in organic solvent-aqueous phase reactions.The components of glycerides varied considerably during hydrolysis, whereby esterification resulted in a higher quantity of mono- and diglycerides (about 40percent), compared to in the case of hydrolysis, for which the value was about 10-20percent.
- Omar, Ibrahim Che,Nishio, Naomichi,Nagai, Shiro
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p. 2153 - 2160
(2007/10/02)
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- Blends of lanolin wax and esters of aliphatic polyols and fatty acids
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Blends of the hard wax fraction obtained from the fractionation of lanolin and an ester derived from an aliphatic polyol or ether polyol and fatty acid are suitable substitutes for U.S.P. anhydrous lanolin and can be substituted therefore in cosmetic formulations (creams, lotions, etc.) without detracting from the properties of the system.
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- Positional specificity of purified milk lipoprotein lipase
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Highly purified lipoprotein lipase from bovine milk has been incubated with emulsified 1,3 dioleoyl 2 [1 14C]oleoyl [3H]glycerol, and the reaction products have been separated by thin layer chromatography on silicic acid impregnated with boric acid. There was an appreciable accumulation of monoacylglycerol, preponderantly of the 2 configuration. The 1(3) monoacylglycerol found must have been formed by isomerization from the 2 isomer. A small but constant amount of 1,2(2,3) diacylglycerol was found among the reaction products, but no 1,3 diacylglycerol. In incubations of albumin bound 1(3) monooleoylglycerol and 2 monooleoylglycerol with the enzyme, glycerol was produced by hydrolysis of the 1(3) isomer exclusively. In the incubations with trioleoylglycerol substrate, glycerol thus must have been obtained by hydrolysis of 1(3) monoacylglycerol formed by isomerization from the 2 isomer. The main reaction sequence was triacylglycerol → 1,2(2,3) diacylglycerol → 2 monoacylglycerol ? 1(3) monoacylglycerol → glycerol. The enzyme thus has a specificity for position 1(3) of the acylglycerols.
- Nilsson-Ehle,Egelrud,Belfrage,Olivecrona,Borgstroem
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p. 6734 - 6737
(2007/11/03)
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