Production of propylene glycol fatty acid monoesters by lipase-catalyzed reactions in organic solvents

Fatty acid monoesters of propylene glycol (1,2-propanediol) are good water-in-oil emulsifiers. These esters were synthesized enzymatically to overcome the problems associated with chemical processes. APseudomonas lipase was added to reaction mixtures containing propylene glycol and various acyl donors (fatty acids, fatty acid ethyl esters, fatty acid anhydrides and triglycerides) in organic solvents, and the mixtures were shaken at 30°C. The products were analyzed by gas chromatography. The yield of monoesters was affected by the acyl donors, organic solvents, temperature, water content, pH memory and reaction time. The anhydrous (lyophilized) enzyme and fatty acid anhydrides were best for monoester production. The optimum pH ranges were 4–5 and 8–10. The yields of propylene glycol monolaurate, monomyristate, monopalmitate, monostearate and monooleate with 50 mM fatty acid anhydrides as acyl donors were 97.2, 79.6, 83.7, 89.7 and 93.4 mM, respectively; those with 50 mM fatty acids as acyl donors were 37.3, 28.7, 28.7, 35.3 and 36.2 mM, respectively. The yields of propylene glycol monopalmitate, monostearate and monooleate with 50 mM triglycerides as acyl donors were 87.4, 65.1 and 83.2 mM, respectively.     

分散因素对氯乙烯微悬浮聚合的影响及对策

本文对氯乙烯微悬浮聚合中影响氯乙烯分散的诸因素:乳化剂及其助剂,氯乙烯以及分散系统自聚等进行了分析,并针对目前生产中出现的问题提出相应对策。     

耐温耐盐乳状液驱替体系性能研究

对合适HLB值的乳化剂进行了筛选和评价,优选了具有较强稳定性能的乳状液。静态测试结果显示乳状液具有较好的耐温和耐盐性能,随着矿化度的提高,其稳定性能略有降低,但是幅度不大。该乳状液体系具有很高的黏度,渗流阻力能够提高140倍左右,说明乳状液体系能够在高温高盐条件下取得很好的驱替效果。驱替实验还表明乳状液滴与孔喉的匹配性决定了乳状液在多孔介质中的运移能力。     

氧化蜡乳液的研制

采用自制氧化蜡研制氧化蜡乳液,考察了乳化剂的质量分数、乳化温度、搅拌速率、乳化时间等因素对乳液性能的影响,确定了制备氧化蜡乳液的复合乳化剂质量分数以及乳化工艺。实验结果表明,当氧化蜡质量分数15%、乳化剂质量分数3%、乳化剂的亲水亲油平衡值约为12.0、乳化温度85℃、搅拌速率800r/min、乳化时间35min时,可得到稳定性好、分散性为一级的乳白色的氧化蜡乳液。     

强化作用在重油催化裂化中的应用

对常渣及其添加表面活性剂后的强化油进行了催化裂化反应对比实验研究,结果表明,由于表面活性剂对催化裂化反应的强化作用,改善了原料油与催化剂的接触状况,提高了原料的转化深度。在相同反应条件下,强化油的转化率比常渣高4～6个百分点,汽油产率提高2～5个百分点,液化气产率提高3个百分点左右,液收率增加4～6个百分点,干气产率增加近2个百分点,柴油产率下降1～2个百分点,焦炭产率下降2个百分点。在近似转化率下,强化油作为原料时的产品选择性优于常渣。     

Enzymatic synthesis of sugar esters and their potential as surface-active stabilizers of coconut milk emulsions

Sugar esters are compounds with surfactant properties (biosurfactants), i.e., capable of reducing the surface tension and promote the emulsification of immiscible liquids. On the other hand, as with all emulsions, coconut milk is not physically stable and is prone to phase separation. Therefore, the aim of this work was to evaluate the synthesis of fructose, sucrose and lactose esters from the corresponding sugars using Candida antarctica type B lipase immobilized in two different supports, namely acrylic resin and chitosan, and evaluate its application in the stabilization of coconut milk emulsions. The enzyme immobilized on chitosan showed the highest yield of lactose ester production (84.1%). Additionally, the production of fructose ester was found to be higher for the enzyme immobilized on the acrylic resin support (74.3%) as compared with the one immobilized on chitosan (70.1%). The same trend was observed for the sucrose ester, although with lower percentage yields. Sugar esters were then added to samples of fresh coconut milk and characterized according to their surface tension, emulsification index and particle size distribution. Although the microscopic analysis showed similar results for all sugar esters, results indicated lactose ester as the best biosurfactant, with a surface tension of 38.0 N/m and an emulsification index of 54.1%, when used in a ratio of 1:10 (biosurfactant:coconut milk, v/v) for 48 h experiments.     

Formation of corn fiber gum-milk protein conjugates and their molecular characterization

Corn fiber arabinoxylan is hemicellulose B isolated from the fibrous portions (pericarp, tip cap, and endosperm cell wall fractions) of corn kernels and is commonly referred to as corn fiber gum (CFG). Our previous studies showed that CFG isolated from corn bran (a byproduct of corn dry milling) contains very little protein and is an inferior emulsifier for oil-in-water emulsion systems as compared to corn fiber gum isolated from corn fiber derived from the corn wet-milling process. The protein deficient CFG isolated from corn bran was covalently conjugated with byproducts of cheese processing, β-lactoglobulin (β-LG) and whey protein isolate (WPI) using an economical food-grade Maillard-type heating reaction for the purpose of increasing their commercialization potential as a food emulsifier and soluble nutritional additive in beverages. The formation of the CFG-protein conjugates has been confirmed by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). It has also been demonstrated that CFG-protein conjugates are capable of producing fine emulsions with better stability than either CFG or protein alone. The molecular characterization of CFG-protein conjugates was performed by high-performance size-exclusion chromatography (HPSEC) coupled to on-line multi-angle laser light scattering and viscometric detection. The analysis by HPSEC revealed that CFG-protein conjugates had higher weight-average molar mass (M_w, 340-359 kDa) and polydispersity (M_w/M_n, 1.74) than the corresponding unconjugated CFG (M_w, 290 kDa and M_w/M_n, 1.35). The z-average root-mean-square radius of gyration (R_gz) of CFG-protein conjugates was slightly higher (30.5-33.5 nm) in comparison to CFG (29.5 nm) but their weight-average-intrinsic viscosity (η) remained unchanged (about 1.32 dL g⁻¹). The Mark-Houwink exponent “a” of conjugates (0.40) was lower than the unconjugated CFG (0.53) indicating the formation of a more compact structure after conjugation with protein. These findings should benefit the beverage industry, which can use this information to produce a high quality emulsifier from the low-value byproducts of corn dry milling and cheese processing.     

The influence of macromolecular architecture on the critical aggregation concentration of large amphiphilic starch derivatives

A range of hyperbranched emulsifiers were prepared by reaction between starch and 2-octen-1-yl succinic anhydride (OSA, commonly used in the food industry), under slightly basic conditions in water, leading to starches bearing hydrophobic OSA groups randomly distributed along the chains. By using different starch backbones and varying the amount of OSA during the synthesis, amphiphilic OSA-modified starches were obtained that formed aggregates in water and having controlled structural parameters. These parameters were characterized using ¹H NMR, multiple-angle laser light scattering and size-exclusion chromatography. The critical aggregation concentration (CAC) was measured for samples with different levels of OSA modification, of macromolecular size and degree of starch branching. Increasing the dispersity in macromolecular size and/or degree of OSA substitution noticeably decreased the CAC. The results are interpreted in terms of the branching structure and conformation of the modified starches: all findings can be understood in terms of the various influences of molecular size, composition and flexibility. The structural factors affecting the CAC of large hyperbranched surfactants are found to be similar to those seen with smaller and simpler branched synthetic surfactants.     

Production and Emulsifying Effect of Polyglycerol and Fatty Acid Esters with Varying Degrees of Esterification

Esters with acyl groups can be formed by the esterification of polyglycerol. The purpose of the present study was to produce fatty acid esters [hexanoic (caproic), octanoic (caprylic), decanoic (capric), dodecanoic (lauric), tetradecanoic (myristic), hexadecanoic (palmitic), octadecanoic (stearic)] and polyglycerol (average number‐of degrees of polymerization of 5) with varying degrees of esterification and to examine their emulsifying properties. A number of fundamental catalysts of polyglycerol acylation reactions by methyl esters of carboxylic acid were studied, and sodium methoxide was found to be the best choice. The temperature rate of transesterification increased from 180 to 220 °C with the fatty acid chain alkyl residue. Synthesized mono‐, di‐, tri‐, tetra‐, and heptaesters of various fatty acids and polyglycerol provided the highest hydroxyl values from 15 to 815 mg KOH g^?1 and saponification values from 82 to 321 mg KOH g^?1. The emulsifying properties were assessed for all polyglycerol and fatty acid esters, with results showing maximum emulsifying effect for tri‐ and tetraesters of capric, lauric, and caprylic acids. Regardless of the hydrophilic–lipophilic balance value (HLB) of polyglycerol esters and carboxylic acid, a 4:1 ratio of sunflower oil to water formed a water‐in‐oil type emulsion. When mixing oil and water in a 1:1 ratio, mono‐ and diesters of polyglycerol formed an oil‐in‐water type emulsion, heptaesters formed a water‐in‐oil type emulsion, and tri‐ and tetraesters formed both of types of emulsions, depending on the length of the acid hydrocarbon radicals.     

Designing emulsion droplets of foods and beverages to enhance delivery of lipophilic bioactive components – a review of recent advances

Lipophilic bioactive compounds such as lipids, vitamins and phytochemicals serve important antioxidant, functional, nutritional and structural roles in the human body. Colloidal systems such as emulsions are particularly suitable matrices for the protection and delivery of these compounds. This article summarises the principal lipophilic bioactives important for human health and challenges associated with their delivery. It discusses the compositional and physical characteristics of emulsions in relation to bioactive delivery, and chemical stability aspects to consider when engineering efficient emulsion delivery systems. The literature shows that aspects such as oil type, droplet size, interfacial composition and solubilisation capacity impact bioactive availability and that their effects are bioactive specific. Therefore, emulsions must be tailored to the bioactives delivered. Much of the present knowledge is based on in vitro studies, and more data from animal and human models are required to better understand the relationship between emulsion characteristics and bioavailability of lipophilic bioactives.