Butyl Ester Research Articles

The influence of vegetable oils composition on separation of transesterification products, especially quality of glycerol

The paper describes the properties of glycerol produced by transesterification, especially the ester content in the glycerol phase (ester losses) including the distribution of esters according to higher fatty acids. Glycerol, produced by transesterification of oil as a side product – the polar glycerol phase, is an important chemical raw material. The decreasing of ester losses is important because it (i) increases the ester yield and especially (ii) decreases the cost of glycerol purification. The transesterification of oils (rapeseed, olive, palm, sunflower and Camelina Sativa) with various distributions of fatty acids was carried out by methanol, ethanol and butanol including different transesterification stopping. The losses of ethyl and butyl esters are much higher than losses of methyl ester (approximately 2–3x). The distribution of ethyl and butyl esters in the glycerol phase is the same as in the ester phase, whereas distribution of methyl ester is different and depends on the way of transesterification stopping. The reason is the different polarity of methyl esters, which depends on the type of fatty acid. The polarity increases with increasing of double bonds, i.e. the most soluble is methyl ester of linolenic acid in the glycerol phase.

Responses of 2,4-D resistant Brassica rapa L. biotype to various 2,4-D formulations and other auxinic herbicides

Brassica rapa L. is an important weed in winter wheat, barley, and other winter crops, and its control has become more difficult due to the development of resistant biotypes. The aim of this study was to record the presence of a B. rapa biotype resistant to 2,4-D herbicides and to evaluate the effect of different formulations of 2,4-D and other auxin herbicides on this biotype. Three independent dose-response experiments were conducted to evaluate: (i) the sensitivity of the resistant and susceptible B. rapa biotypes to increasing doses of 2,4-D, (ii) the sensitivity of the resistant biotype to different formulations of 2,4-D (butyl ester, dimethylamine salt, acid, and choline salt), and (iii) the sensitivity of the resistant biotype to other auxinic herbicides (picloram, dicamba, fluroxypyr, clopyralid and MCPA). The B. rapa resistant biotype showed a resistance index of 4.7, which means that, to achieve 50% inhibition of survival, the dose required needs to be approximately five-fold higher that required for the susceptible biotype. The GR50 of the resistant biotype for the different 2,4-D formulations marketed in Argentina was variable. The 2,4-D acid microemulsion formulation was the product that showed the highest control efficiency and biomass reduction. The resistant biotype was not susceptible to clopyralid, dicamba, or picloram, with maximum phytotoxicity of 25%, even when treated with four times the recommended dose and without biomass reduction, showing cross-resistance.

Organo-metallic pollutants of distillery effluent and their toxicity on freshwater fish and germinating Zea mays seeds

Anaerobically treated molasses-based distilleries spent wash is a major source of terrestrial and aquatic pollution due to the mixture of the various unknown organometallic compounds in discharged waste. The nature of pollutants present in effluent has to be characterized prior to the evaluation of their fate in the environment at various tropic levels. The absorption maxima (λmax) were obtained at 295 nm of pollutants present in spent wash which indicated that melanoidins are a major colorant along with other organic compounds. Abundantly identified compounds with GC–MS in effluent were found: 1,2,4,5-tetrahydro-2-methyl-3H-2-benzazepine-3-one, 6-(trifluoromethyl)-1H-imidazole [4,5-c] pyridine, 4,6-di-t-butyl-1H, 3H-thieno[3,4-c] thiophene, butanoic acid, trimethylsilyl ester, silane, (dodecyloxy)trimethylsilyl ester, 4-styryl [2,2] paracyclophane, 4-(p-cumylphenoxy) phthalonitrile, hexadecanoic acid, trimethylsilyl ester, butyl ester, and squalene. Some of these compounds are known with mutagenic and androgenic properties. The toxicity test of post-methanated distillery effluent (PMDE) showed direct toxic effects on catfish (Heteropneustes fossilis) even at 1% (v/v) concentration and caused degeneration of primary and secondary lamellae of the gill and the epithelial layer. Further, higher concentrations between 5 and 10% of PMDE showed loss of primary and secondary lamellae of gills, and liver catalase activity was also increased dramatically in H. fossilis, indicating the generation of oxidative free radicals. Similarly, inhibition of α-amylase activities in germinating Zea mays L. (Maize) seeds was also noted at 10% PMDE. This study confirmed the environmental toxicity of effluent with freshwater fish and Zea mays seeds.

Biochemical and microbiological analyses of Burukutu (native beer) and a brand of factory-based lager beer (STAR)

Consumption of Burukutu (native beer) among the people of the area of study is a norm. The techniques applied in its production are crude and non scientific. As a result, undesirable compounds, which may themselves be toxic, could be produced as components of the ‘brew’. Also, microbes present may be pathogenic. Ten samples were aseptically collected. A composite of 2 ml portions of each of nine (9) Burukutu samples was prepared for microbial count and identification. In the case of organic metabolites and alcohol content, individual samples were analysed. Spectrophotometry was applied to determine the alcohol content; mass spectrometry method was used to identify the metabolites generated. Nutrient agar and indole test were applied for aerobic plate count and microbial identification. The results obtained revealed three isolates in all the samples thus: Escherichia coli, Bacillus species and Saccharomyces cerevisiae. The alcohol content ranged between 2.0-2.6% (v/v). Metabolites generated in both Burukutu and factory-based lager beer included glycerine, 1-pentanol, methanol, 1-glyceraldehyde, trimethylene oxide, 1-butanol, toluene, benzene acetic acid Propanoic acid, 2-hydroxy ethyl ester, Heptafluorobutyric acid, n-Pentyl ester, 4-butoxy-5,7-dinitrobenzo[1,2,5] Thiadiazole, Benzene acetic acid, 2 butyl ester, ethyl alcohol. Both Burukutu contain undesirable metabolites which may synergise with alcohol making it toxic to the system. Personal and environmental hygiene will help reduce levels of contaminants in alcoholic beverages otherwise pathogenic microbes could grow in the liquor being consumed.

Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and tert-butyl ester synthesis

Silver/manganese dioxide (Ag@MnO2) nanorods are synthesized and characterized by scanning electron microscopy, transmission electron microscopy, energy dispersive X-ray spectroscopy, X-ray powder diffraction, and X-ray photoelectron spectroscopy. It was discovered that Ag@MnO2 nanorods can realize hydrogen-borrowing reactions in high yields and are also effective for the synthesis of tert-butyl esters from aryl cyanides and tert-butyl hydroperoxide in a short period of time. Mechanistic experiments revealed that this catalytic system acts as a Lewis acid in hydrogen-borrowing reactions, while the synthesis of tert-butyl esters occurs through a radical pathway. This is the first report on the excellent catalytic activity of Ag@MnO2 nanorods as a catalyst.

Bench Motor Testing of Blended Fuels on their Basis

Alkaline transesterification of sunflower oil by n-butanol and ethanol on alkoxide-containing dried solutions of potassium hydroxide has been carried out. Complex character of spontaneous dividing of butanolysis products, accompanying with formation of three different species of glycerol layers, was observed. One of the later was found to be high-alkaline pure glycerol. Bench motor testing of biodiesel/diesel blends demonstrated slightly better power performance of butyl esters comparing with ethyl esters and regular decrease of harmful emissions (CO2, CO, NOx, CH) while increasing biodiesel fraction in mixture.

Abstract PS18-46: Inhibition of breast cancer stem cells in 2- and 3-dimensional culture by novel salinomycin analogs

Abstract Breast cancer remains one of the leading cancers among women and an estimated 90% of breast cancer deaths are due to metastasis. Cancer stem cells (CSCs) are a sub-population of cancer cells which are responsible for its initiation, progression and metastasis. CSCs are resistant to conventional chemo- and radio-therapies and therefore therapeutic strategies targeting CSCs hold great potential for novel advances in cancer treatment. Salinomycin (SAL) is a naturally occurring polyether ionophore antibiotic which was shown to effectively target breast CSCs. A library of 17 novel SAL analogs was synthesized and screened to identify compounds with improved selectivity against breast cancer stem cells. SAL analogs were either single modified esters or amides in the C1 position or double-modified C20-oxo derivatives. Eight single- and two double-modified analogs were more potent (IC50 range of 1.13 ± 0.19 to 3.93 ± 0.39 µM) towards the breast cancer cell line MDA-MB-231 compared to parent SAL (IC50 of 4.90 ± 1.60 µM). These analogs induced DNA fragmentation suggestive of apoptotic cell death. Compounds 2 (butyl ester analog of SAL) and 17 (double-modified C20-oxosalinomycin with benzhydroxamic acid) have been chosen for follow-up screening due to their improved activity and selectivity versus parent SAL. This included clonogenic assays to assess the ability of the compounds to affect cell renewal, and wound healing assays to assess cell migratory properties. In both assays, compound 17 showed superior properties over SAL. Furthermore, analog 17 showed improved targeting of breast CSCs in both cell monolayer and organoid culture as assessed in assays measuring the CD44+/CD24- stem cell sub-population. Analogs and parent compound were further studied examining (ADP-ribose) polymerase (PARP) cleavage and Bcl-2 levels by immunoblotting. All three compounds induced loss of 116 kDa PARP expression within 48h, with the highest effect induced by analog 17. In addition, treatment with compound 17 caused a decrease in Bcl-2 expression as early as 24 h. Select analogs were next screened against the NCI-60 Human Tumor Cell Line Panel. The described above double-modified analog was found to be more potent than SAL towards all 6 breast cancer cell lines in the panel as well as other tumor types. The present findings highlight the therapeutic potential of SAL analogs towards breast stem cells and support further research and clinical development of these compounds. Funding: The present study was funded by grants (to AM and TCC) from the Arkansas Breast Cancer Research Program. Testing was performed by the Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, http://dtp.cancer.gov. Citation Format: Alicja Joanna Urbaniak, Megan R. Reed, Michał Antoszczak, Michał Sulik, Adam Huczyński, Robert L. Eoff, Melanie C. MacNicol, Timothy C. Chambers, Angus M. MacNicol. Inhibition of breast cancer stem cells in 2- and 3-dimensional culture by novel salinomycin analogs [abstract]. In: Proceedings of the 2020 San Antonio Breast Cancer Virtual Symposium; 2020 Dec 8-11; San Antonio, TX. Philadelphia (PA): AACR; Cancer Res 2021;81(4 Suppl):Abstract nr PS18-46.

Molecular dynamics simulation of the formation of methane hydrates in the presence of KHIs

Poly(N-vinylpyrrolidone) (PVP) and PVP-A were selected as typical kinetic hydrate inhibitors (KHIs) to simulate the inhibition processes of methane hydrate formation, where PVP-A is obtained by introducing butyl ester groups into the PVP molecule. The results show that KHIs do not significantly delay the formation of the first complete hydrate cage, but inhibit the nucleation of methane hydrate by retarding the formation and growth of the labile clusters and reducing the stability of newly formed hydrate cages. The steric effect and H-bond between inhibitor molecules and the labile clusters are not the main reasons for inhibiting methane hydrate nucleation. The formation of hydrate cages can be effectively inhibited by KHIs during the nucleation stage, but ineffective in the rapid growth stage. Moreover, PVP and PVP-A exhibit dual-functionality, i.e., disturbing H-bonding between water molecules and the movement of methane and water.

Method for the Preparation of N‐protected β‐Cyano L‐alanine Tertiary Butyl Esters

AbstractHere we report a simple, efficient and scalable one‐pot procedure for the synthesis of N‐protected β‐cyano L‐alanine tertiary butyl esters from N‐protected L‐asparagines. Reaction of N‐protected L‐asparagines with 2.2 equivalents of (Boc)2O and catalytic amount of N,N‐dimethylamino pyridine (DMAP) in tertiary butanol at room temperature resulted N‐protected β‐cyano L‐alanine tertiary butyl esters. We also synthesized N‐protected β‐cyano L‐alanines from the obtained crude N‐protected β‐cyano L‐alanine tertiary butyl esters without column chromatography on gram scale in good yields. Control experiments gave the corresponding nitrile acids over the tertiary butyl esters. Later, we synthesized nitrile containing dipeptides by coupling N‐Boc‐β‐cyano L‐alanine 4 a with amino acid methyl ester hydrochlorides.

Characterization of a novel lipase from Bacillus licheniformis NCU CS-5 for applications in detergent industry and biodegradation of 2,4-D butyl ester

Enzymatic degradation has become the most promising approach to degrading organic ester compounds. In this study, Bacillus licheniformis NCU CS-5 was isolated from the spoilage of Cinnamomum camphora seed kernel, and its extracellular lipase was purified, with a specific activity of 192.98 U/mg. The lipase was found to be a trimeric protein as it showed a single band of 27 kDa in SDS-PAGE and 81 kDa in Native-PAGE. It was active in a wide range of temperatures (5–55 °C) and pH values (6.0–9.0), and the optimal temperature and pH value were 40 °C and 8.0, respectively. The enzyme was active in the presence of various organic solvents, metal ions, inhibitors and surfactants. Both crude and purified lipase retained more than 80% activity after 5 h in the presence of commercial detergents, suggesting its great application potential in detergent industry. The highest activity was found to be towards medium- and long-chain fatty acids (C6-C18). Peptide mass spectrometric analysis of the purified lipase showed similarity to the lipase family of B. licheniformis. Furthermore, it degraded more than 90% 2,4-D butyl ester to its hydrolysate 2,4-D within 24 h, indicating that the novel lipase may be applied to degrade organic ester pesticides.

Cytostatic Activity and Ligand-Receptor Interaction Energy of the Novel Russian-Produced Gestagen Gestobutanoil and its Metabolites

With the aim of clarifying the cytostatic effect of the Russian-made gestagen gestobutanoil (17α-acetoxy-3β-hydroxy-6-methylpregna-4,6-dien-20-one butyl ester), which is a member of an original group of transformed gestagens containing an ester substituent in place of the 3-keto group, the cytostatic activities of its metabolites (17α-acetoxy-3β-hydroxy-6-methylpregna-4,6-dien-20-one (AMP-17) and megestrol acetate) and a reference agent (progesterone) were studied in uterine cervical tumor line HeLa. Complex formation by these steroids with progesterone receptor binding sites was evaluated by computer modeling (docking) by determination of the interaction energy of the partner molecules. The cytostatic activity of gestobutanoil was greater than that of reference compound and may be associated with the formation of its active metabolites. Conformations of the gestobutanoil-receptor complex with binding energies significantly different from those of complexes with progesterone, AMP-17, and megestrol acetate were demonstrated; this may be the cause of changes in the affinity of gestobutanoil for progesterone receptors and modulation of its biological activity.

Interfacial modification enabled room temperature solid-state lithium–metal batteries

Lithium solid-state batteries (SSBs) with tantalum doped Li7La3Zr2O12 (LLZT) inorganic ceramic electrolytes have been attracting much interest for its extraordinary lithium ionic conductivity, non-flammability, and wide electrochemical window. However, poor solid–solid contact between the electrodes and electrolyte results in large interfacial resistance, which hinders its normal operation and practical application. Herein, triethylene glycol diacetate-2-propenoic acid butyl ester (TEGDA-BA) based gel polymer electrolytes (GPE) were fabricated and coated on both sides of spark plasma sintering (SPS)–derived LLZT pellet. GPE introduction not only provides intimate contact between solid electrolyte and electrodes but also avoids side reactions such as reduction of LLZT by lithium anode. Moreover, symmetric Li cell markedly reduced interfacial resistance and exhibited a critical current density up to 1.0 mA cm−2 at room temperature (25 °C), and it can also stably cycle at 0.5 mA cm−2 for over 277 h without Li dendrite formation. The assembled solid-state LiNi0.5Co0.2Mn0.3O2 (NCM523)/GPE–LLZT–GPE/Li battery exhibits high initial capacity (163.5 mAh g−1) at 0.2 C. This work provides a facile method to reduce the interfacial resistance and demonstrates durable high-energy solid-state lithium metal batteries suitable for practical application.

Short Chain (≤C4) Esterification Increases Bioavailability of Rosmarinic Acid and Its Potency to Inhibit Vascular Smooth Muscle Cell Proliferation

Rosmarinic acid is a natural phenolic acid and active compound found in many culinary plants, such as rosemary, mint, basil and perilla. Aiming to improve the pharmacokinetic profile of rosmarinic acid and its activity on vascular smooth muscle cell proliferation, we generated a series of rosmarinic acid esters with increasing alkyl chain length ranging from C1 to C12. UHPLC-MS/MS analysis of rat blood samples revealed the highest increase in bioavailability of rosmarinic acid, up to 10.52%, after oral administration of its butyl ester, compared to only 1.57% after rosmarinic acid had been administered in its original form. When added to vascular smooth muscle cells in vitro, all rosmarinic acid esters were taken up, remained esterified and inhibited vascular smooth muscle cell proliferation with IC50 values declining as the length of alkyl chains increased up to C4, with an IC50 of 2.84 µM for rosmarinic acid butyl ester, as evident in a resazurin assay. Vascular smooth muscle cells were arrested in the G0/G1 phase of the cell cycle and the retinoblastoma protein phosphorylation was blocked. Esterification with longer alkyl chains did not improve absorption and resulted in cytotoxicity in in vitro settings. In this study, we proved that esterification with proper length of alkyl chains (C1–C4) is a promising way to improve in vivo bioavailability of rosmarinic acid in rats and in vitro biological activity in rat vascular smooth muscle cells.

Fuel-grade sunflower oil butyl esters: synthesis, purification, oxidation stability

Current paper deals with production, purification and oxidative stability enhancement of fuel-grade sunflower oil butyl esters as more ecological alternative of methyl esters as biodiesel. The oil feedstock, used in this study, included refined sunflower oil (acid value – 0.05 mg KOH/g; 25.3 % of oleic and 61.2 % of linoleic acids) and wasted frying high-oleic sunflower oil (acid value – 1.20 mg KOH/g; 6.1 % of linoleic and 81.7 % of oleic acids). Butanolysis was carried out using potassium butoxide, obtained from KOH and alcohols via original patent-pending method, under mild reaction conditions (alcohol-to-oil molar ratio – 4.5-5.0, 15°C, 1.4-1.6 %еq. KOH of butoxide, 20-30 min). High molar yield of butyl esters (93-96 %) was achieved, while glycerol and vast majority of alkaline catalyst formed the separate reaction products phase mainly in the course of reaction. Ester enriched phases were purified in order to obtain fuel-grade butanol-based biodiesel. Samples after removing of butanol under vacuum followed by water washing and drying were characterized by not enough high butyl esters content (about 94-95 %), as well as higher than allowed content of unconverted glycerides. Vacuum distillation as final purification step allowed fitting butyl esters samples composition within the requirements for biodiesel fuel. Distilled samples contained about 99 % of butyl esters, 0.4-0.5 % of monoglycerides and almost no n-butanol, glycerol, di- and triglycerides. Oxidative treatment (110°C, 6 h, air bubbling) revealed the high oxidation stability of the sample, originated from wasted high-oleic oil, due to the predominance of oleic acid in its fatty acid composition. The sample, obtained from refined sunflower oil (mainly linoleic acid in fatty acid composition), demonstrated very low stability. Addition of at least 2000 mg/kg of antioxidant 2,6-di-tert-butyl-4-methylphenol was shown to be able to improve this characteristic to the level of biodiesel requirements.

Evaluation of actinomycetes isolated antimicrobial metabolites as potent inhibitor of multidrug resistant organisms

With the increased metabolic diversity and adaptability, microorganisms are capable of living in diverse environmental conditions. Various microorganisms present in natural environment are resistant to some of the current antibiotics that has lead to discovery of new antibiotic compounds. Soil organisms have been paid a great attention and are recognized as a good source of antibiotic compounds. Actinomycetes are well known for their importance as bioactive metabolites in different sectors. Present study was carried out via isolation of actinomycetes from rhizospheric soil from four different locations of Rajasthan and the isolation was performed on Actinomycetes Isolation Agar (AIA) medium. In this study AIA10 isolate was screened for their antimicrobial potential against five selected microbial pathogens viz . Staphyloccocus aureus , Pseudomonas aeruginosa , Klebsiella pneumonia , Proteus vulgaris and Bacillus subtilis . After Solvent extraction, crude extracts of benzene and ethyl acetate were tested for antibacterial activity. GC-MS technique identified the presence of major components like Heptadecane at retention time (RT) - 18.131 (5.07 %), Heneicosane at RT - 20.935 (14.63 %), Hexadecanoic acid, Butyl ester at RT - 25.611 (4.92 %), Eicosanoic acid, 2,3-Bis(Acetyloxy)Propyl ester at RT - 32.509 (8.15 %), 9-Octadecenoic acid (Z)-, 2,3-Bis(Acetyloxy)Propyl ester at RT - 34.978 (34.32 %) in benzene crude extract. In ethyl acetate extract major compounds identified were, Pentadecanoic acid at RT - 6.25 (21.251 %), N-Hexadecanoic acid at RT - 22.527 (12.79 %), Eicosanoic acid at RT - 23.788 (14.18 %), Hexadecanoic acid, 2-Hydroxy-1-(Hydroxymethyl) Ethyl ester at RT - 29.593 (5.59 %), Octadecanoic acid, 2,3-Dihydroxypropyl ester at RT - 33.182 (3.50 %) and 5,11,17, 23-Tetratert Butyl pentacyclo [19.3.1.1~3,7~.1~9,13~.1~15,19~]Octacosa1(25),3(28),4,6,9(27),10,12,15(26),16,18,21, 23-Dodecaene-25,26,27,28 Tetrol at RT - 54.152 (9.92 %). Primary screening was tested and the activity was observed against S. aureus and P. vulgaris. In secondary screening, benzene and ethyl acetate extract was found active against S. aureus , at inhibition zone IZ = 10 and 20 mm, respectively. The study conducted proposes these actinomycetes as a potent source for antimicrobial metabolites.

1H-NMR based lipid profiling of Gossypium hirsutum seed oil at different developmental stages

1H-NMR spectroscopy is emerging as powerful robust analytical technique in analyzing bio constituents present in plants. It offers non-invasive method for identification and quantification of several Phyto-constitutes in a single step without much pre-processing of the samples. In the present study, 1H-NMR spectroscopy-based lipid profiling was performed on Gossypium hirsutum seeds, which were collected at different developmental stages. 1H-NMR study reveals the presence of sterols, butyl ester of fatty acids, free fatty acids (FFA), triacyl glycerides (TAG), monounsaturated fatty acids (MUFA), polyunsaturated fatty acids (PUFA) and saturated fatty acids (SFA) at different percentage at different developmental stages. The 1H-NMR result demonstrates the presence of high concentration of FFA in early developmental stage and increased concentration of TAG at maturation stage. The 1H-NMR results suggest that stage III of seed development can be identified as turning point, as at this stage sterols and butyl ester of fatty acids becomes insignificant followed by high accumulation of TAG.

Biological activity of benzoxazolinone and benzoxazolinthione derivatives

The article presents the herbicidal, defoliating, fungicidal properties of the synthesized derivatives of benzoxazolinones and benzoxazolinethions. It was shown that 3-alkylbenzoxazolinones, 3-alkyl-6-halobenzoxazolinones and 2-alkylthiobenzoxazoles exhibit herbicidal action during the growing season of plants, and they also cause cotton leaves to drop up to 70%. It was found that 3-alkylbenzoxazolinones and 2-alkylthiobenzoxazoles exhibited fungicidal activity against the pathogen, Fugarium oxyporum and Verticillum dahlia. Among them, 2-methylthiobenzoxazole inhibited spores of the fungi Verticillum dahlia by 96.4% and benzoxazolyl-2-carbamic acid butyl ester by 65%. These compounds exhibit fungicidal action against the pathogens of powdery mildew on cucumbers - Erysiphe cichoraceorum and powdery mildew on wheat - Erysiphe graminis, approaching the control Karatan. Apparently, these compounds are chemicals of contact action.

Methods for producing butyl acetate

Butyl acetate is a universal solvent widely used in various industries, such as the leather and pharmaceutical industries. The article describes the ways to obtain butyl acetate in various ways: in-line and continuous. The material balance of the production of this product is also given. Butyl acetate (acetic acid butyl ester) is the most common solvent in the production and use of paints and varnishes.Dissolves cellulose ethers, oils, fats, chlorinated rubbers, vinyl polymers, carbiol resins, etc. The addition of butyl acetate together with a small amount of butyl alcohol prevents whitening of the lacquer films. It is a fragrant substance that is part of fruit essences and perfume compositions. It is used in the tanning industry as tannin.

Castor Epoxy Fatty Acid Alkyl Ester Estolides as Bioplasticizers for Poly(Vinyl Chloride)

AbstractEpoxy fatty acid alkyl ester estolides were synthesized from castor oil to be used as biobased plasticizers for poly(vinyl chloride) (PVC) as a safer replacement for phthalate plasticizers. Initially, castor oil was transesterified with methanol or n‐butanol to quantitatively yield castor fatty acid alkyl esters. Acetylation of hydroxyl function with acetic anhydride led to the formation of estolide. The unsaturation was epoxidized, resulting in a bifunctional epoxy fatty acid alkyl ester estolide. The bioplasticizers were compounded with PVC and were evaluated for their functionality and compared with commercial phthalate plasticizer diisononyl phthalate (DINP) and nonphthalate 1,2‐cyclohexanoic acid diisononyl ester (DINCH). The bioplasticizers showed excellent gelation, efficiency, and compatibility, as well as plastisol viscosity and thermal properties, comparable to or better than the plastisols prepared with commercial controls DINP and DINCH. The volatility of the methyl ester was inferior to the butyl ester. Both compounds showed low water resistance properties. Further evaluation of the butyl ester under tropical conditions of high temperature and humidity confirmed limited compatibility. This indicates that the castor epoxy fatty acid ester estolides would be better suited for applications that do not come in contact with water for prolonged periods, such as flooring, artificial leather, wiring, or wall coverings.

Obtaining High‐Paraffin‐Content Oil Depressants

AbstractA depressor action composition was prepared for lowering the pour point of high‐paraffin oils based on butanol and cotton soap stock fatty acids (FA), mainly a C16–C18 distillate fraction. The possibility of using cotton soap stock FA for their esterification with butyl alcohol and ester production based on them is shown. A scheme for preparing the depressor action reagent “BEG‐1” based on the esterified FA, monoethanolamine, and cotton soap stock is proposed. When the BEG was introduced into the samples of high‐paraffin oil taken directly from the group metering device, a decrease in the paraffin crystal size and shape was observed, i.e. their almost complete dissolution, which was accompanied by a change in the viscosity of the samples. Compositions having high surface‐active properties, thermodynamic resistance, and stability were prepared. The paraffin crystal morphology, crystal structure, and shape change were studied. The data obtained are of value for the pipeline transport of hydrocarbons, as the use of the proposed depressor action reagent for high‐paraffin oils can significantly reduce the viscosity of the oil in the pipeline, helping to reduce the energy costs associated with heating the oil for its pumping.