Alcohol Ether Research Articles

Nickel-Catalyzed Removal of Alkene Protecting Group of Phenols, Alcohols via Chain Walking Process.

An efficient nickel-catalyzed removal of alkene protection group under mild condition with high functional group tolerance through chain walking process has been established. Not only phenolic ethers, but also alcoholic ethers can be tolerated with the retention of stereocenter adjacent to hydroxyl group. The new reaction brings the homoallyl group into a start of new type of protecting group.

Properties and Vesicle Formation in Mixed Systems of a Branched Anionic Carboxylate Surfactant and a Cationic Surfactant

Abstract Mixtu res of the anionic surfactant AEC7-Na (branched alcohol ether carboxylate) and the cationic surfactant didecylmethylhydroxyethylammonium chloride (DEQ) were systematically investigated. The results showed that the mixtures possess synergisms. The DEQ-AEC7-Na mixture with a mass ratio of 1:1 showed the best result in terms of surface activity, wettability and emulsifying performance. However, when the mass ratio m(DEQ):m(AEC7-Na) = 8:2, the foaming ability and foam stability of the individual surfactants are better. Vesicles smaller than 100 nm coexist with worm-like micelles as soon as a small amount of AEC7- Na is added to DEQ (m(DEQ):m(AEC7-Na) = 8:2). At m(DEQ):m(AEC7-Na) = 4:6 and 2:8, vesicles of approximate ly 80 nm were observed.

Synthesis and Properties of a Quaternary Ammonium Salt Gemini Surfactant with Diethyl Ether as the Spacer Group

Abstract A quaternary ammonium salt gemini surfactant (C12N)2O with diethyl ether as the spacer group was synthesized by dodecyl dimethyl amine and 2-chloroethyl ether. The structure of the product was confirmed by Fourier transform infrared spectra (FT-IR) and proton nuclear magnetic resonance spectra (1H NMR), which showed that the structure of the synthesized product was consistent with the theoretical structure. We tested the surface tension of (C12N)2O at 25°C and found the critical micelle concentration (CMC) was roughly 2 orders of magnitude lower than that of dodecyl trimethylamine chloride (DTAC). Gemini structure and the unique diethyl ether spacer group endowed the novel amphiphile excellent properties including low contact angle and high antistatic property. (C1 2N)2O showed good compatibility with alcohol ether sulfate (AES) and dodecylbenzene sulfonate (LAS) in surfactant mixed systems. When the ratio of (C12N)2O:AES was 1:4 and (C12N)2O:LAS 1:9, the emulsifying properties were preferable to single surfactant.

Predicting VLE and Odor Intensity of Mixtures Containing Fragrances with COSMO-SAC

In this study, vapor–liquid equilibria (VLE) of binary, ternary, and quaternary systems containing fragrances were predicted using COSMO-SAC. A model variant including multiple energies for the description of different hydrogen bonds (alcohol–alcohol, alcohol–ketone, alcohol–ether) was used. Based on equilibrium vapor compositions, odor intensity, and character of fragrance mixtures were calculated using Stevens’ power law for olfaction intensity scale and stronger component model for quality perception. Very good agreement between predicted and measured data was obtained with COSMO-SAC. Model predictions were similar to UNIFAC outcomes, but without using any binary interaction parameter. Based on these results, this study also indicates the possibility to use COSMO-SAC to predict VLE in mixtures that contain fragrances with missing UNIFAC parameters.

Synthesis of Fatty Alcohol Ether Carboxylic Ester Surfactant and its Performance in an Anionic/Non-Ionic Mixed System

A salt-type fatty alcohol ether carboxylic ester (AECE-Na) surfactant with both anionic and non-ionic characteristics was synthesised using a fatty alcohol ether (AEO) and succinic anhydride. Compared with traditional synthetic methods, neither irritating substances (chloroacetic acid and chloroacetate) nor precious metals (Pt and Pd) were used in the synthesis, which is a simple, economic, and green method. FT-IR and 1H NMR spectroscopies and MALDI TOF mass spectrometry were used to prove the molecular structure of the target product AECE-Na. In addition, the surface activities, intermolecular interactions, application properties, and aggregation behaviours of the individual systems (AEO and AECE-Na) and the anionic/non-ionic mixed system (AECE-Na/AEO) were investigated. The results showed that AECE-Na/AEO exhibits synergistic effects in terms of surface tension reduction efficiency, wetting, emulsification, foaming, and detergency compared with the individual systems.

Pathomorphological changes in the testicles of goats in acute anaplasmosis

The aim of the research was to study pathomorphological changes in the testicles of goats in acute anaplasmosis. Diagnosis of anaplasmosis in sick goats was carried out taking into account the characteristic clinical signs and studies of peripheral blood smears. Blood smears after fixation in alcohol ether were stained according to Romanovsky-Giemsa by hematoxilin and eosin. For histological examination, pieces of testicles and appendages of testicles of 0.5 cm thick were selected, which were fixed in an 8% neutral aqueous solution of formalin. The resulting material was poured into paraffin according to the generally accepted method. Histological sections of 5-8 microns thick were made from the obtained paraffin blocks and stained with hematoxilin and eosin using the method of Van Gieson and Mallory. Micro photos were made with a series of rendered images on the basis of Olimpus 2000. The study revealed the following changes: the spermatogenic epithelium has desquamation, in the lumen of the convoluted seminiferous, there were tubules protein detritus, exfoliated cells of seminiferous epithelium and macrophages. Sertolli cells were in a state of vacuole dystrophy and necrosis. In the interstitial tissue around arterial vessels and convoluted seminiferous tubules, focal accumulation of lymphoid-macrophage infiltration was found. Endocrine cells located in the interstitial were in a state of vacuole dystrophy and necrosis. Thus, in goats older than 6 months with acute anaplasmosis in the testicles, pathomorphological changes are characteristic of acute parenchymal orchitis.

Pengaruh variasi unsur Gd pada struktur kristal superkoduktor Y-358 (Y3-XGdxBa5Cu8O18- δ)

Abstract - Research on the effect of Gd element variations on the Y-358 (Y3-xGdxBa5Cu8O18-δ). Superconducting crystal structure has been carried out. In this study the samples were held in a magnetic stirrer for 24 hours, calcined using a temperature of 600 ° C for 3 hours and sintering using a temperature of 900 ° C for 10 hours. The results of XRD characterization showed sharp peaks that indicate the occurrence of crystallization well. And each sample has the same functional group at a certain wave number. The functional groups found in each sample were Mono Aromatic, Para Aromatic, Ether Alcohol Anhydride, Esters, Nitro Carboxylic Acid (N = O), Alkyl CH (Stretching), Phenol Alcohol, OH Carboxyl Acid (alcohol, phenol, hydrogen bonds).

Effect of Si/Al Ratio on the Catalytic Activity of Two‐Dimensional MFI Nanosheets in Aromatic Alkylation and Alcohol Etherification

AbstractZeolite catalysts with pronounced two‐dimensional (2D) morphologies, specifically 2D MFI nanosheets composed of multilamellar stacks of MFI nanosheets, are hypothesized to offer accessibility advantages in catalytic reactions involving large, bulky molecules. The Si/Al ratio of zeolite catalysts is an important parameter determining their performance. However, the effect of Si/Al ratio on catalytic reactivity is not well understood in 2D zeolite catalysts. To provide further insight into this issue, the catalytic performance of 2D MFI nanosheet materials with different Si/Al ratios is compared using the liquid phase Friedel‐Crafts alkylation of mesitylene with benzyl alcohol & the self‐etherification of benzyl alcohol that occurs in parallel, both of which are catalyzed by Brønsted acid sites. The turnover frequency (TOF) of the catalysts is found to decrease with decreasing Si/Al ratio, with the etherification reaction being the main contributor to this trend. When the same reaction is carried out in the presence of a bulky poison, 2,6 di‐tert‐butylpyridine (DTBP), to selectively deactivate the external acid sites, only the etherification reaction of benzyl alcohol takes place in the micropores of the 2D MFI catalyst and the effectiveness factor is found to decrease with decreasing Si/Al ratio. The single component adsorption isotherms of benzyl alcohol show that the uptake normalized per acid site decreases with decreasing Si/Al ratio. Thus, increasing the density of acid sites in the micropores by decreasing the Si/Al ratio makes it more difficult for the reactant molecules to access them, as demonstrated by the decrease in TOF and the effectiveness factor. While the micropore reactions (benzene alkylation, alcohol etherification) showed a clear trend with Si/Al ratio, the reaction catalyzed on the external surface (mesitylene alkylation) did not, showing distinct differences in reactivity.

Efficient Synthesis of Hydrothermally Stable Mesoporous Aluminosilicates Using Trace Amounts of an Anionic Surfactant as a Co-Template

Mesoporous aluminosilicates (MAs) with excellent hydrothermal stability have been a growing interest because of their potential application in face-centered cubic. The process of improving the P123 utilization efficiency and reducing the water consumption is an important issue for the synthesis and application of MAs. In this study, trace amounts of alcohol ether sulphate (AES) being the co-template were introduced into high P123 concentration to synthesize MAs. The water consumption is reduced 77.3%, and P123 utilization efficiency is increased 1.2 times in comparison to that of the conventional method. In high P123 concentration solution, micelle aggregates were formed without AES, resulting in the formation of less ordered MAs. However, well-dispersed micelles were formed in the presence of AES, which is beneficial for the subsequent assembling process. In addition, the micellar state corresponding to different AES contents and the influence on physicochemical properties of MAs were discussed.

Impact of Selected Cosmetic Ingredients on Common Microorganisms of Healthy Human Skin

Human skin is a complex ecosystem and is host to a large number of microorganisms. When the bacterial ecosystem is balanced and differentiated, skin remains healthy. However, the use of cosmetics can change this balance and promote the appearance of skin diseases. The skin’s microorganisms can utilize some cosmetic components, which either promote their growth, or produce metabolites that influence the skin environment. In this study, we tested the ability of the Malassezia species and some bacterial strains to assimilate substances frequently used in dermal formulations. The growth capability of microorganisms was determined and their lipase activity was analyzed. The growth of all Malassezia spp. in the presence of free acids, free acid esters, and fatty alcohols with a fatty chain length above 12 carbon atoms was observed. No growth was observed in the presence of fatty alcohol ethers, secondary fatty alcohols, paraffin- and silicon-based substances, polymers, polyethylene glycols, quaternary ammonium salts, hydroxy fatty acid esters, or fatty acids and fatty acid esters with a fatty chain length shorter than 12 carbon atoms. The hydrolysis of esters by Malassezia lipases was detected using High Performance Thin Layer Chromatography (HPTLC). The production of free fatty acids as well as fatty alcohols was observed. The growth promotion or inhibition of bacterial strains was only found in the presence of a few ingredients. Based on these results, formulations containing microbiome inert ingredients were developed.

Effect of foaming agent on physical and mechanical properties of alkali-activated slag foamed concrete

Alkali-activated slag cement has the characteristics of high viscosity, quick hydration, setting and hardening, and high strength, which are suitable for the preparation of foamed concrete. Three foaming agents of sodium α-olefin sulfonate (AOS), sodium dodecyl sulfate (K12) and sodium alcohol ether sulphate (AES) with the same foam stabilizer of silicone resin polyether emulsion FM-500 (MPS) were used to prepare foam. The three foam properties are similar and foam stability of AOS and K12 is better than that of AES. Effective foam ratio is put forward to express stability of foam in paste slurry. Effective foam ratio and porosity has a great effect on dry apparent density of water glass-activated slag foamed concrete. With the increase of foam content, effective foam ratio of AES decreases obviously, while that of K12 and AOS show a slight decrease. At low foam content, AES can better reduce the dry apparent density. Increase foam content of AOS and K12 appropriately may reduce dry apparent density. Rsd and compressive strength of foamed concrete with AOS foam is the highest. When porosity is similar, average pore size and pore size distribution has a great effect on thermal conductivity and mechanical properties of AAS foamed concrete. Average pore size of O3 is smaller than that of K3 and E3. O3 also shows the narrowest air-void size distribution with the majority of the voids smaller than 400 μm. Average roundness of three type foam is much the same. Foam stability is the main factor affecting pore structure of AAS foamed concrete. AOS can be preferred to prepare AAS foamed concrete.

Comparative study on the surface activity and adsorption behavior of linear fatty alcohol ether carboxylic ester with fatty alcohol ether

The linear fatty alcohol ether carboxylic ester (A12/14EC9E-H/A12/14EC9E-Na) surfactants were successfully prepared from the raw materials fatty alcohol ether (A12/14EO9) and succinic anhydride with a green and efficient one-step method. The chemical structure of A12/14EC9E-H was characterized by Fourier transform infrared (FT-IR), 1H-Nuclear magnetic resonance (1HNMR) and Matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF-MS). In addition, a comparative study on the surface activity and adsorption behavior at the air/water interface of A12/14EC9E-H, A12/14EC9E-Na and A12/14EO9 was carried out via various measurements. The results showed that the nonionic surfactant A12/14EC9E-H displayed better surface activity, stronger wetting ability and faster diffusion rate at the air/water interface than the nonionic surfactant A12/14EO9. Furthermore, the adsorption mechanism of A12/14EC9E-H, A12/14EC9E-Na and A12/14EO9 is the mixed diffusion-kinetic adsorption.

Synthesis of Biomass-Derived Ethers for Use as Fuels and Lubricants.

Ethers synthesized from biomass-derived compounds have exceptional properties as fuels, lubricants, and specialty chemicals and can serve as replacements for petroleum-derived products. Recent efforts have identified heterogeneous catalysts for the selective synthesis of ethers from alcohols, aldehydes, ketones, furans, esters, olefins, carboxylic acids, and other molecules derived from biomass. This Review highlights the scope of etherification reactions and provides insights into the choice of catalysts and reaction conditions best suited for producing targeted ethers from the available starting materials. First, the properties of ethers for specific applications and the methods by which synthons for ether synthesis can be obtained from biomass are discussed. Then the progress that has been made on the synthesis of ethers via the following methods is summarized: direct etherification of alcohols; reductive etherification of alcohols with aldehydes or ketones; etherification of furanic compounds, esters, and carboxylic acids; and the addition of alcohols to olefins. Next, the mechanisms of these reactions and catalyst properties required to promote them are discussed, with the goal of understanding how reaction conditions can be tuned to optimize catalyst activity and selectivity towards desired ethers. The Review closes by examining the tradeoffs between catalyst selectivity, activity, stability, and reaction conditions required to achieve the most economically and environmentally favorable routes to biomass-derived ethers.

Esterification of oat-hull cellulose

The influence of the composition of the working mixed acid, mass ratio, and nitration temperature and time on the properties and yield of cellulose nitrates from an unconventional feedstock such as the large-tonnage grain-processing residue, oat hulls, was studied. Experimental statistical models were constructed on the basis of a series of experiments. They enable the properties of cellulose nitrates to be predicted as a function of the mixed acid composition and conditions of the nitration process. The mixed acid composition and the mass ratio of mixed acid to cellulose were found to have the primary effect on the properties of cellulose nitrates, while the nitration temperature and time had no noticeable effect on the final result. Under the optimum synthetic conditions, pilot batches of cellulose nitrates were produced, which corresponded to Colloxiline-N in the main properties: mass fraction of nitrogen was 12.08–12.18%, viscosity was 12–15 mPa s, and the solubility in an alcohol—ether mixture was 98%. The correspondence of the synthesized samples to Colloxiline-N was confirmed by FTIR spectroscopy. The cellulose nitrates derived from the unconventional feedstock may find practical use in manufacturing ballistic powder and composite explosives.

Experimental investigation of the wetting ability of surfactants to coals dust based on physical chemistry characteristics of the different coal samples

To select suitable surfactant as water-spray additive to improve dust suppression efficiency, six types of coal sample (lignite, long flame coal, non-caking coal, gas coal, coking coal, and anthracite) were selected from some typical mining areas in China, the influence of the physical chemistry characteristics of coal samples on the wetting ability of surfactants to the coals dust was investigated. Their proximate composition, ultimate content, chemical structure, surface morphology, pore structure parameters, and contact angle were determined. Three kinds of anionic surfactants – Sodium Alcohol Ether Sulphate (AES), Sodium Alpha-Olefin Sulfonate (AOS), Fatty Acid Methyl Esters Ethoxylate Sulfonate (FMES) – and one kind of nonionic surfactant – Coco Diethanolamide (CDEA) – were selected to carry out sedimentation experiments on the coal samples dust, to explore the main factors influencing the wettability of the coal samples dust. Among these factors, pore size is the main factor determining the wettability of coal dust, the contact angle decreases linearly (R2 = 0.96) with pore size increase. The experimental results demonstrate that the following factors produce correspondingly increased wettability: higher moisture content, lower carbon content, higher oxygen content, more oxygen-containing functional groups, and increased pore size. In addition, the wettability of the six types of the coal samples dust shows a high-low-high trend with metamorphic degree increase, lignite has the strongest wettability, and the coking coal with the highest degree of metamorphism in the selected bituminous coal sample has the weakest wettability. Moreover, compared with nonionic surfactants, anionic surfactants have stronger wetting ability, but the same anionic surfactants have different wetting abilities to coal dust with different metamorphic degrees. AOS has stronger wetting ability to the dust of long flame coal, non-caking coal, and anthracite; AES has stronger wetting ability to the dust of lignite and coking coal; and FMES has stronger wetting ability to the dust of gas coal. The research results provide a theoretical basis for different coal mines to select suitable surfactants as water-spray additives to improve dust suppression efficiency.

The Effect of Mixed Organic Solvents Extract of Trachyspermum ammi with Different Concentrations on the Body Weight of Mice

Background and Aim. In traditional medicine, the use of Trachyspermum ammi, commonly known as 'Ajwain', is recommended to improve digestive function of the stomach and has effects on body weight. The present study aims to determine the effect different concentrations of mixed organic solvents extract (MOSE) of Trachyspermum ammi on mice compared with control group.
 
 Materials and Methods. This experimental-interventional study was performed on mice weighing an average of 21 gr, selected through random allocation method. The mice were divided into four groups of 24 (one control group and three case groups), receiving 0.5, 1 and 2% concentrations or density of MOSE of Trachyspermum ammi (0.001 mg/kg). First, the dried fruit of Trachyspermum ammi was powdered and then, it was extracted using various organic solvents including petroleum ether, chloroform, ethyl acetate and ethyl alcohol. The extract was fed to the mice for 14 days and their weight was controlled every day.
 
 Results. The hypothesis of diversity in the weight gain of mice among the four groups after 15 days was significant; weight gain in control group was significantly higher than other groups (p<0.05). In addition, comparing the weight gain of the mice that received different concentrations of MOSE of Trachyspermum ammi (0.5, 1 and 2%) did not show a significant difference (p<0.05).
 
 Conclusion. The use of Trachyspermum ammi plant can not be effect on body weight compared to the control group. This could not be a suitable way to weight change through diet.

Biogenic zinc oxide nanoparticles-enhanced biosynthesis of lignans and neolignans in cell suspension cultures of Linum usitatissimum L

Zinc oxide nanoparticles (NPs) have emerged as a novel elicitor for enhanced biosynthesis of secondary metabolites in in vitro plant cell cultures. The current study was aimed to explore elicitation abilities of ZnO-NPs for enhanced accumulation of lignans and neolignans in cell cultures of Linum usitatissimum. We optimized concentration of zinc oxide NPs before carrying out a full-fledged experiment. Subsequently, an optimum dose of 100 mg/l was introduced into the culture medium on day 0, days 0 and 15, and finally days 0 and 25. We observed that repeated elicitation stimulated various parameters and physiological responses in Linum usitatissimum cell cultures than one-time elicitation. Repeated elicitation of cell cultures on day 0 and 15 resulted in highest fresh weight (412.16 g/l) and lignans production (secoisolariciresinol diglucoside 284.12 mg/l: lariciresinol diglucoside 86.97 mg/l). Contrarily, repeated elicitation on day 0 and 25 resulted in highest DW (13.53 g/l), total phenolic production (537.44 mg/l), total flavonoid production (123.83 mg/l) and neolignans production (dehydrodiconiferyl alcohol glucoside 493.28 mg/l: guaiacylglycerol-β-coniferyl alcohol ether glucoside 307.69 mg/l). Enhancement in plant growth and secondary metabolites accumulation was several fold higher than controls. Furthermore, a linear relationship existed between total phenolic and flavonoid contents which in turn was correlated with higher antioxidant activities.

Mechanical properties of renewable plasticizer based on ricinoleic acid for PVC

Expoxy acylated ricinoleic acid binary alcohol ether ester (EARABAEE) is a kind of novel bio-based environmental-friendly plasticizer. EARABAE was synthesized from ricinoleic acid and binary alcohol ether and it's chemical structure was characterized by FT-IR, 1H NMR, ESI-TOF-MS. EARABAEE was mixed with the poly(vinyl chloride) (PVC) and mechanical property was investigated. The static mechanical property tests indicated that the PVC film plasticized by epoxy benzoylated ricinoleic acid ethylene glycol butyl ether ester (2c) has better tensile strength and the film plasticized by epoxy acetylated ricinoleic acid propylene glycol methyl ether ester (3d) has higher elongation at break. The dynamic mechanical property was evaluated by balanceable torque and mixing process energy, Haake rheometer tests showed that the 3d-plasticized PVC film has bigger balanceable torque and mixing process energy. In addition, the proportion of 3d and DOTP markedly affected the dynamic mechanical property. When the 3d content was more than 25%, the balanceable torque and mixing process energy decreased significantly with the 3d content increased.

Study on the properties and self-assembly of fatty alcohol ether carboxylic ester anionic surfactant and cationic surfactant in a mixed system

Mixed system A12–14EC9E-Na/DEQ exhibits excellent surface activity, application properties, and interesting self-assembly behaviors.

Enhanced production of lignans and neolignans in chitosan-treated flax (Linum usitatissimum L.) cell cultures

Abstract Linum usitatissimum is a source of pharmacologically active lignans and neolignans. An effective protocol has been established for the enhanced biosynthesis of lignans and neolignans in cell cultures of Linum usitatissimum by using chitosan addition. Gene expression analysis of monolignols (PAL, CCR and CAD), lignans (DIR, PLR and UGT) and neolignans (PCBER) biosynthetic genes by RT-qPCR as well as monolignol biosynthetic PAL, CCR and CAD enzyme activities evidenced a stimulation following chitosan treatment. Validated reverse phase high-performance liquid chromatography coupled to diode array detection was used to quantify secoisolariciresinol diglucoside (SDG) and lariciresinol diglucoside (LDG), dehydrodiconiferyl alcohol glucoside (DCG) and guaiacylglycerol-β-coniferyl alcohol ether glucoside (GGCG) showed that chitosan treated cell cultures had better accumulation of these metabolites. Maximum enhancements of 7.3-fold (28 mg/g DW) occurred for LDG, 3.5-fold (58.85 mg/g DW) in DCG and while the least enhancement of 2-fold (18.42 mg/g DW) for SDG was observed in 10 mg/l chitosan treated cell cultures than to controls. Furthermore, same concentration of chitosan also resulted in 1.3-fold increase in antioxidant activity. Compared to the lignans and neolignans accumulations observed in wild type and RNAi-PLR transgenic flaxseeds, chitosan-treated cell cultures appeared to be a very effective production system for these compounds.