Reduced Emulsion Stability Research Articles

Emulsion Stability and Rheological Properties of Emulsions Prepared with Ozonized Hazelnut Oil

In this study, physical and rheological characteristics of the emulsion stabilized with whey protein isolate (WPI) at a concentration of 0.25% (w/w) and containing ozone applicated hazelnut oil (OHO) were studied. The hazelnut oil was subjected to ozone gas exposure for durations of 1, 5, 30, 60, 180, and 360 min. The emulsions made with both control (HO) and OHO were analysed to assess emulsion properties. It was observed that as the duration of ozone application increased, the emulsion activity index (EAI) experienced a decrease. Specifically, ozone applications of 30, 60, and 180 min significantly reduced emulsion stability index (ESI). The creaming ratio of emulsions formulated with OHO for durations of 1, 5, 30, 60, and 180 min were found to be 23%, 20%, 18%, 16%, and 44%, respectively. Optical microscopy revealed that significant flocculated droplet formed in emulsions including OHO. The longer time the ozone application resulted that the emulsions exhibited more solid-like behaviour. Furthermore, differential scanning calorimeter (DSC) was utilized to assess the changes in the melting and cooling profiles of hazelnut oil after being applicated with ozone. An increase in ozone application duration led to the melting peaks broadening and shifting towards lower temperatures. Also, ozone application caused that the sharp exothermic crystallization shifted towards lower temperatures and become broader and less pronounced as the duration of the application increased.

Effect of surfactants on the interfacial behaviors of diacylglycerol-based solid lipid nanoparticles and physical stability of W/O emulsion

The influence of surfactants (Span 80, Span 60, PGPR and sodium caseinate) on the stability of W/O emulsions stabilized by diacylglycerol (DAG)-based solid Lipid nanoparticles (SLN) was investigated. DAG-based SLN showed phase separation at high NaCl concentration and acidic pH although the SLN-stabilized W/O emulsion was minimally affected. Span 80 increased the hydrophobicity whereas Span 60 increased the hydrophilicity of SLN. With concentration close to CMC, both Span surfactants caused detachment of SLN from interface and reduced emulsion stability. Nonetheless, addition of a small amount (0.1 wt%) of Span surfactants increased the interfacial modulus. The co-adsorption of SLN and PGPR at the oil-water interface promoted the formation of denser network structure and higher interfacial elasticity, which enhanced the emulsion rigidity and freeze-thaw stability. Sodium caseinate (NaCAS) showed intense competition with particles for adsorption at the interface and caused emulsion destabilization. Consequently, the NaCl release rate was directly influenced by the emulsion stability and the interaction between surfactants with SLN. The results have important implications for applying DAG nanoparticles as stabilizers in W/O emulsions with tailoring interfacial rigidity and water-soluble component release behaviors.

CO2-Switchable Emulsification and Demulsification of Pickering Emulsion Stabilized by Zirconium-Based Metal–Organic Frameworks

Stimuli-responsive Pickering emulsions have aroused considerable amounts of attention recently because of their potential for on-demand demulsification. Metal–organic frameworks (MOFs) are promising emulsifiers for the construction of Pickering emulsions due to their ultrahigh specific surface area, tunable porosity, and designable structures. However, CO2-responsive zirconium-based MOF-stabilized Pickering emulsions have been rarely reported up to now. Herein, a new series of amine-functionalized UiO-66-O-APTES were developed via the covalent post-modification of UiO-66-OH with different amounts of (3-aminopropyl)triethoxysilane (APTES) and were then applied to construct CO2-switchable Pickering emulsions. It was shown that UiO-66-O-APTES could emulsify toluene and water well to form an emulsion even at the content of 0.1 wt %. Significantly, the Pickering emulsion could be reversibly demulsified and re-emulsified by alternate CO2 and N2 bubbling under constant pressure. Mechanism results revealed that the CO2-switchable phase transition based on the formation of hydrophilic ammonium salts resulting from the reaction of APTES with CO2, which lowered the wettability of particles, reduced emulsion stability, and resulted in emulsion breaking. After CO2 was removed, the Pickering emulsion could be rebuilt by the reverse reaction. By using this strategy, a controllable and highly effective CuI-catalyzed cycloaddition reaction has been achieved, and the coupling of efficient condensation, product separation, and recovery of MOF catalysts has been demonstrated to give rise to a sustainable reaction process.

Wood lignocellulosic stabilizers: effect of their characteristics on stability and rheological properties of emulsions

Lignocellulosic materials from the forest industry have shown potential to be used as sustainable hydrocolloids to stabilize emulsions for many applications in life science and chemical industries. However, the effect of wood species and recovery method on the product’s properties and ability to stabilize emulsions of isolated lignocellulosic compounds is not well understood. Hemicelluloses, abundant lignocellulosic side stream, exhibit differences in their water solubility, anionic character, lignin content, and degree of acetylation. Here, we explored stability and rheological properties of model emulsions (5% hexadecane and 1% stabilizer, w/w) stabilized by different grades of sprucewood galactoglucomannan (GGM) and birchwood glucuronoxylan (GX) hemicelluloses. The results were compared to known soluble, insoluble, charged, and non-charged cellulosic stabilizers, namely methyl cellulose (MC), carboxymethyl cellulose (CMC), anionic- and nonionic-cellulose nanocrystals (aCNC and dCNC). The results showed that GX emulsions were highly stable compared to GGM emulsions, and that deacetylation and lignin removal markedly reduced emulsion stability of GGM. Carboxymethylation to increase anionic characters enhanced the emulsion stabilization capacity of GGM, but not that of GX. Investigating flow behaviors of emulsions indicated that hemicelluloses primarily stabilize emulsions by adsorption of insoluble particles, as their flow behaviors were similar to those of cellulose nanocrystals rather than those of soluble celluloses. Understanding the impact of the variations in composition and properties of hemicellulose stabilizers to stabilize emulsions allows tailoring of their recovery processes to obtain desirable hydrocolloids for different applications.

Effect of monomer hydrophilicity on ARGET–ATRP kinetics in aqueous mini‐emulsion polymerization

AbstractActivators regenerated by electron transfer (ARGET) atom transfer radical polymerization (ATRP)‐based aqueous miniemulsion polymerization where the polymerization takes place in the stabilized monomer droplets is described. In this work, we compared styrene, n‐butyl methacrylate (nBMA) and tert‐butyl methacrylate (tBMA) and investigated the influence of their hydrophobicity on dispersity, molecular weight and particle stability based their partition coefficients (logP) (2.67, 2.23, and 1.86, respectively). Tetrabutylammonium bromide (TBAB) was used as a phase transfer agent for the controlled delivery of Cu2+‐Br/tris(2‐pyridylmethyl)amine (TPMA), a hydrophilic catalyst, into monomer droplets of varying hydrophobicity. The resulting dispersity and particle stability of each polymer is a function of its logP value, with the most hydrophobic monomer (styrene) displaying the narrowest dispersity and most control (Đ < 1.3), and the most hydrophilic polymer poly(tert‐butyl methacrylate) (PtBMA) having reduced emulsion stability, determined by the observation of aggregate formation. Selected polymerization parameters, including effects of total ascorbic acid feed concentration and the monomer concentration and their effects on dispersity are reported. The controlled polymerizations of hydrophilic monomers using ARGET‐ATRP in miniemulsion conditions and understanding the effect of monomer hydrophilicity on the emulsion stability will broaden the use of ARGET‐ATRP in emulsion polymerization for the synthesis of polymer‐grafted nanoparticles with hydrophilic corona.

Emulsification properties of bovine milk protein isolate and associated enzymatic hydrolysates

Oil-in-water (O/W) emulsions were prepared using bovine milk protein isolate (MPI) or MPI hydrolysates containing 1.60% (w/v) protein, 3.60% (w/v) lipid blend and 7.00% (w/v) lactose. The role of enzymatic treatment of MPI with Flavourzyme™, Neutrase™ and Protamex™ at two hydrolysis time points per enzyme [ranging in degree of hydrolysis (DH) from 15.6 to 37.1%] on the emulsifying properties was determined. All emulsion samples had mean fat globule size (d43) values < 1 μm after homogenisation. The hydrolysate containing emulsions displayed reduced emulsion stability under accelerated storage conditions, i.e., following an applied centrifugal force, and reduced heat stability at pH 7.0 compared with emulsions formed using intact MPI. The results demonstrated that hydrolysis reduced emulsion stability in the model system studied. Emulsion instability was hydrolytic enzyme dependent, increased with increasing DH and increasing content of peptides <1 kDa.

Technical emulsifiers in aerosol whipping cream – Compositional variations in the emulsifier affecting emulsion and foam properties

Mono- and diacylglyceride emulsifiers (E471) are used in various food products like dairy whipping cream, ice cream and aerosol whipping cream. For aerosol whipping cream, which requires high emulsion stability and foaming properties over a shelf life of >6 months, the effect of compositional variation of E471 has not been investigated. In this study four E471 emulsifiers were used (0.2–1.0 g 100 g−1) to process aerosol whipping cream by two stage homogenisation at 4/1 MPa. After one week storage at 6 °C apparent viscosity and particle size distribution were measured. Samples were foamed by oversaturation with nitrous oxide and overrun, foam firmness, drainage and residual cream were determined. Saturated monoacylglycerides were shown to be most effective at emulsion and foam stabilisation. Unsaturated monoacylglycerides reduced emulsion stability and prevented foaming of the model system. Pickering stabilisation by singular fat globules is postulated as foam stabilisation mechanism in aerosol whipping cream.

Mechanisms and performance of cellulose nanocrystals Pickering emulsion chitosan coatings for reducing ethylene production and physiological disorders in postharvest ‘Bartlett’ pears (Pyrus communis L.) during cold storage

Pickering emulsion coating (CNCP-CH) composed of oleic acid (OA, 1, 2, and 3%, w/w), cellulose nanocrystal (CNC, 0.1, 0.3, and 0.5%, w/w), and 2% chitosan (CH) was optimized for high emulsion stability. It was found that OA concentration played significant role on emulsion stability. Increasing OA from 1 to 3% reduced emulsion stability ~43%, indicated by the thickness of separated cream layer in the emulsion. ‘Bartlett’ pears (Pyrus communis L.) coated by CNCP-CH containing 1% OA showed significantly reduced ethylene production than that coated with 2% and 3% OA at 1-month of accelerated cold storage at 1.7 °C. The superficial scald on pear peels was only observed on fruit coated by CNCP-CH with 3% OA, but not that with 1% or 2% OA. Therefore, CNCP-CH coating with 1% OA, 0.1% CNC, and 2% CH was suggested for delaying ripening and superficial scald of ‘Bartlett’ pears during the long-term cold storage.

Polypeptide Profile, Amino Acid Composition and Some Functional Properties of Calabash Nutmeg (Monodora myristica) Flour and Protein Products

AbstractThe aim of this work was to compare the physicochemical and functional properties of calabash nutmeg (Monodora myristica) seed protein flour with those of protein‐enriched products (albumin, globulin, and protein isolate). Defatted M. myristica seed flour (MMF) was used to prepare various protein products. A NaCl extract of MMF was dialyzed against water to obtain the soluble albumin fraction (MMA) and a precipitated globulin fraction (MMG). MMF was also extracted with NaOH, the extract adjusted to pH 4.0 and the precipitated proteins collected as the isolate (MMI). Non‐reducing gel electrophoresis showed that the MMF, MMG and MMI had similar composition that was dominated by 55 and 110 kDa polypeptides while MMA consisted mainly of smaller (&lt;35 kDa) polypeptides. However, under reducing conditions, the 110 kDa polypeptide was not observed. Amino acid composition revealed an Arg/Lys ratio that increased in the extracts (1.92, 2.28 and 2.11 for MMA, MMG and MMI, respectively) relative to that in MMF (1.85). MMA had 67.5–86.5% protein solubility in the pH 4.0–6.0 range while those of MMF, MMG, and MMI were 37.7–63.8, 2.7–69.4 and 3.8–55.1%, respectively. MMA, MMG and MMI were found to be better emulsifiers based on their smaller oil droplet sizes (8–14 μm) compared with the 14–33 μm for MMF emulsion. Maximum foaming capacity was highest for MMI (205%) when compared with MMA or MMG (150%) and MMF (89%). We conclude that protein enrichment led to significantly enhanced emulsion and foam‐forming properties but high solubility may have contributed to reduced emulsion stability.

Interfacial and Emulsion Stabilizing Properties of Indigenous Acidic and Esterified Asphaltenes

This article describes interfacial properties of acidic asphaltenes and their ability to stabilize emulsions. Asphaltenes extracted from crude oil were esterified with methanol to prevent ionization of carboxylic acid at high pH. Interfacial tension (IFT) between water and asphaltenes in xylene was significantly lower in basic than in acidic and neutral media, while the elasticity of the corresponding films was higher. These results are consistent with much more stable asphaltene-based emulsions in basic medium. For ester-asphaltenes, the IFT only showed a slight decrease under basic conditions and the interfacial elasticity was close to that in acidic solutions and only slightly higher than for neutral medium. While the asphaltene-stabilized emulsions showed a strong increase in stability in basic medium, this increase was much less for ester-asphaltene emulsions. Salt influenced the interfacial properties and generally reduced emulsion stability.

Formation and functional attributes of electrostatic complexes involving napin protein isolate and anionic polysaccharides

The formation of electrostatic complexes involving a napin protein isolate (NPI) and carboxylated alginate (AL) and sulfated (κ-, ι-, λ-type carrageenan) (CG) polysaccharides was investigated at a biopolymer mixing ratio of 10:1 (NPI/polysaccharide) as a function of pH (4.0–12.0) using turbidity and electrophoretic mobility. The functionality of the ensuing complexes was tested on the basis of their solubility, emulsion stability and foaming capacity and stability relative to NPI alone. Complexation follows two pH-dependent structure forming events associated with the formation of ‘soluble’ and ‘insoluble’ complexes. Soluble and insoluble complexes for NPI–AL, NPI–κ-CG, NPI–ι-CG and NPI–λ-CG mixtures occurred at pHs 7.1 and 6.2, 8.6 and 7.0, 9.5 and 9.3, and 9.0 and 8.7, respectively. Complexation resulted in a shift in net neutrality from 5.0 for NPI alone to pH 4.2, 3.7, 3.2 and 2.3 in the presence of κ-CG, ι-CG, λ-CG and AL, respectively. Solubility and foaming capacity of NPI were reduced with the addition of polysaccharide. Foaming stability was similar for NPI–κ-CG and NPI–λ-CG mixtures relative to NPI, but increased and decreased for NPI–ι-CG and NPI–AL mixtures, respectively. Emulsion stability was found to be similar for all mixtures relative to NPI, except for the NPI–ι-CG mixture which had reduced emulsion stability.

Response surface methodology for optimization of the mucilage extraction process from Pereskia aculeata Miller

In this report, a process for hydrocolloid extraction from Pereskia aculeata Miller (Barbados gooseberry), popularly known in Brazil as Ora-pró-nóbis (OPN), was developed. In the process, several operations, such as extraction, pressing, filtration, precipitation, grinding and drying, were required. The independent variables evaluated to determine the optimum extraction conditions were the ratio of water:raw material and the extraction temperature. The significant results at each stage were analyzed using the response surface method. The conditions that presented the highest precipitate yield, highest pH value, highest hue value (clear product), highest filtrate viscosity and minimum flow rate value were a water:raw material ratio of 2.46–3.70 L/kg and an extraction temperature between 54.6 and 80 °C. Using the optimized process, gums were prepared at different concentrations and the centesimal composition, mineral content, viscosity and emulsion formation capacities were analyzed. The stability of these emulsions was evaluated at room temperature and at 80 °C. The emulsion formation capacity of the product was verified as being proportional to the increase of the powder concentration. The OPN gums obtained at a solution concentration of 1 g/100 mL presented an emulsion formation capacity of 83%, and the increase in temperature reduced emulsion stability. The powdered product obtained was found to be close to yellow in color with high protein content and with functionalities that can be used in the food industry.

Lutein-enriched frankfurter-type products: Physicochemical characteristics and lutein in vitro bioaccessibility

This paper reports a study of the physicochemical characteristics of lutein-enriched frankfurter-type products with two fat levels, and the lutein in vitro bioaccessibility in these products. In general, the high-fat products possessed better emulsion stability and greater hardness and chewiness than low-fat samples. For each fat level, the addition of lutein extract in olive oil reduced emulsion stability in meat products. The presence of lutein reduced the lightness and increased the redness of samples. Lutein was highly stable upon in vitro digestion, with overall recovery of over 84% at the end of the duodenal phase and very low isomerisation. Micellarisation was high but depended on the fat content, ranging from 29–34% (for the low-fat sample) up to 73–81% of the amount initially present (for the high-fat sample). Storage (22 days at 4 °C) did not significantly affect lutein content or bioaccessibility. Our results support the suitability of meat products as lutein carriers and as a means to increase the systematic intake of lutein.

Effect of Inorganic Solids, Wax to Asphaltene Ratio, and Water Cut on the Stability of Water-in-Crude Oil Emulsions

The formation of stable water-in-crude oil emulsions during petroleum production and refinery may create sever and costly separation problems. It is very important to understand the mechanism and factors contributing to the formation and stabilization of such emulsions for both great economic and environmental development. This article investigates some of the factors controlling the stability of water-in-crude oil emulsions formed in Burgan oil field in Kuwait. Water-in-crude oil emulsion samples collected from Burgan oil filed have been used to separate asphaltenes, resins, waxes, and crude oil fractions. These fractions were used to prepare emulsion samples to study the effect of solid particles (Fe3O4) on the stability of emulsions samples. Results indicate that high solid content lead to higher degree of emulsion stability. Stability of emulsion samples under various waxes to asphaltenes (W/A) ratios have also been tested. These tests showed that at low W/A content, the emulsions were very stable. While at a wax to asphaltene ratio above 1 to 1, the addition of wax reduced emulsion stability. Stability of emulsion samples with varying amount of water cut has also been investigated. Results indicated that stability and hence viscosity of emulsion increases as a function of increasing the water cut until it reaches the inversion point where a sharp decline in viscosity takes place. This inversion point was found to be approximately at 50% water cut for the crude oils considered in this study.

Effects of protein level and fat/oil on emulsion stability, texture, microstructure and color of meat batters

Beef meat batters formulated with increasing protein level (10–15%) and containing 25% beef fat were compared to batters prepared with 25% canola oil. Emulsion stability of the canola oil treatments was higher (less separation during cooking) at the 10–13% protein level compared to the beef fat treatments. However, above 13% protein this was reversed and the canola oil treatments showed high fat and liquid separation, which did not occur at all in the beef fat treatments. This indicates differences in stabilization of fat versus oil in such meat emulsions. Hardness of the cooked meat batters showed significantly ( P < 0.05) higher values when the protein level was raised, and was higher in canola oil than in beef fat meat emulsions at similar protein levels. Products’ chewiness were higher in the canola oil treatments compared to the beef fat emulsions. Lightness decreased and redness increased in canola oil batters as the protein level was raised. The micrographs revealed the formation of larger fat globules in the beef fat emulsions compared to the canola oil meat emulsions. The canola oil treatment with 14% protein started to show fat globule coalescence, which could be related to the reduced emulsion stability.

Influence of heat processing on functional properties of Australian wattle seed ( Acacia victoriae Bentham) extracts

Whole wattle ( Acacia victoriae Bentham) seed was extracted with water before or after a soaking/heat treatment regime designed to destroy its protease inhibitors. The yield, composition and physical properties of these extracts were measured and they were then subjected to an analysis of their functional properties, which included emulsion and foam formation and stabilization, solubility at different pH values and gelling ability. Processing of soaked wattle seed at 100 °C for 30 s led to a much reduced extract yield and viscosity at both pH 4 and 7, decreased its water-soluble carbohydrate content but increased its protein content, and solubility under alkaline conditions. Processing of wattle seed before extraction also led to increased emulsion droplet size and reduced emulsion stability, the differences being more pronounced in emulsions formed with 20% oil compared with 50% oil-in-water emulsions. Comparatively, the emulsions formed using extract from non-processed wattle seed were very stable at both 20% and 50% oil levels, especially at pH 7 where the enhanced viscosity of the extract predominated. All extracts had very low foaming capacity, and gelation did not occur in any of the samples even at 10% (w/v) extract concentration.

Effects of petroleum resins on asphaltene aggregation and water-in-oil emulsion formation

Abstract Asphaltenes from four crude oils were fractionated by precipitation in mixtures of heptane and toluene. Solubility profiles generated in the presence of resins (1:1 mass ratio) indicated the onset of asphaltene precipitation occurred at lower toluene volume fractions (0.1–0.2) than without resins. Small-angle neutron scattering (SANS) was performed on solutions of asphaltene fractions in mixtures of heptane and toluene with added resins to determine aggregate sizes. Water-in-oil emulsions of asphaltene–resin solutions were prepared and separated by a centrifuge method to determine the vol.% water resolved. In general, the addition of resins to asphaltenes reduced the aggregate size by disrupting the π–π and polar bonding interactions between asphaltene monomers. Interaction of resins with asphaltenic aggregates rendered the aggregates less interfacially active and thus reduced emulsion stability. The smallest aggregate sizes observed and the weakest emulsion stability at high resin to asphaltene (R/A) ratios presumably corresponded to asphaltenic monomers or small oligomers strongly interacting with resin molecules. It was often observed that, in the absence of resins, the more polar or higher molecular weight asphaltenes were insoluble in solutions of heptane and toluene. The addition of resins dissolved these insolubles and aggregate size by SANS increased until the solubility limit was reached. This corresponded approximately to the point of maximum emulsion stability. Asphaltene chemistry plays a vital role in dictating emulsion stability. The most polar species typically required significantly higher resin concentrations to disrupt asphaltene interactions and completely destabilize emulsions. Aggregation and film formation are likely driven by polar heteroatom interactions, such as hydrogen bonding, which allow asphaltenes to absorb, consolidate, and form cohesive films at the oil–water interface.

Effect of high pressure on the emulsifying behaviour of β-lactoglobulin

The influence of high pressure (up to 800 MPa) on the emulsifying behaviour of β-lactoglobulin has been investigated at neutral pH. Fine oil-in-water emulsions (0.4% w/w β-lactoglobulin, 20% v/v oil) made with the pressure-treated protein were found to give substantially larger droplets than those made with the native protein. Visual creaming behaviour and changes in average droplet size have been monitored as a function of storage time. There is a consistent trend of decreasing emulsifying efficiency and (especially) reduced emulsion stability with increasing applied pressure and treatment time. The results are interpreted in terms of pressure-induced unfolding of β-lactoglobulin in aqueous solution, which leads to a loss of emulsifying efficiency due to protein aggregation, despite the increase in surface hydrophobicity, which is confirmed here experimentally. In contrast, high pressure treatment of the corresponding emulsions prepared with the native protein induces only a slight reduction in emulsion stability as reflected in the average droplet size. It appears that the structure of partially unfolded β-lactoglobulin in the adsorbed monolayer at the surface of the emulsion droplets may be relatively unaffected by the pressure treatment.

Herbicide-Oil-Water Emulsions

Oil-water emulsion stability was determined for crop origin and refinement of seed oils and their methyl esterified fatty acids (methylated seed oil) as influenced by emulsifiers and herbicides. Oil-in-water emulsion stability of one-refined, degummed, and crude seed oils was affected by the emulsifier. However, emulsion stability of methylated seed oil was not affected by the refinement of the seed oil used to produce the methylated seed oil or by the emulsifier. Oils without emulsifiers or emulsifiers alone added to formulated herbicide-water emulsions reduced emulsion stability depending upon the herbicide and emulsifier. Further, emulsion stability of formulated herbicides plus oil adjuvants was influenced by the oil type, the emulsifier in the oil adjuvant, and the herbicide. Oil-in-water emulsions improved or were not affected by increasing concentration of the emulsifier in the oil. However, T-Mulz-VO at a concentration greater than 10% with soybean oil or 5% with methylated soybean oil reduced emulsion stability with sethoxydim. Emulsion stability of herbicides with adjuvants depends upon the herbicide, the emulsifier, emulsifier concentration, and the crop origin, type, and refinement of oil.

Preparation and surfactant properties of diglycerol esters of fatty acids

AbstractFatty acid mono‐ and diesters of diglycerol constitute the major portion of commercial polyglycerol esters; hence, their composition influences the performance of the latter as emulsifiers. The correlation of structure of the fatty acids in the mono‐ and diesters with surfactant properties is of interest. Linear diglycerol was isolated from polymerized glycerol by acetonation, fractional distillation and regeneration. Diglycerol mono‐ and diesters of undecenoic, lauric, stearic, oleic and ricinoleic acids were prepared by reacting diglycerol and fatty acids in a refluxing mixture of acetonitrile‐tetrahydrofuran (75:25) in the presence of p‐toluenesulfonic acid and molecular sieves. Mono‐ and diesters were separated by silica gel column chromatography, and their purities were ascertained by thin layer chromatography and determination of saponification value. The structures were confirmed by periodic acid oxidation, chemical‐ionization mass spectrometry and 13 C‐NMR spectroscopy. Surfactant properties of the esters were determined. Monoesters showed higher ability in surface tension reduction, emulsification and foaming than the diesters. Short‐chain fatty acid esters showed better surfactant properties than the long‐chain fatty acid esters. The presence of a central double bond in the lipophilic part of the monoesters reduced emulsion stability. The presence of a hydroxy group in acyl chain retarded foaming and surface tension reducing power.