Sulfonate Esters Research Articles

18F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an 18F‐Labeled Amino Acid**

AbstractIn the development of an efficient 18F‐labeling method for the synthesis of PET tracers, it is essential not only to improve the efficiency of [18F]fluorine incorporation into a carrier but also to minimize non‐radioactive side products from the precursor. Highly reactive sulfonate esters are promising precursors for 18F‐nucleophilic fluorination under mild conditions. However, the expected labeling efficiency from the precursor is often hampered by its competitive degradation due to coexisting bases during 18F‐fluorination. In this report, we designed a 2‐methyl‐6‐nitrobenzenesulfonate (2‐MeNs) ester as a precursor for 18F‐fluorination, in which the methyl group suppresses hydrolysis of the sulfonate ester via steric hindrance. An increase in labeling efficiency in the 18F‐labeling of a neopentyl labeling group was observed for the neopentyl 2‐MeNs ester compared with that of the 2‐nitrobenzenesulfonate ester. Ultimately, we achieved the automated synthesis of an 18F‐labeled amino acid using a neopentyl labeling group by using a 2‐MeNs ester as a precursor.

In Vitro and in Silico Studies of 3‐Hydroxyflavone‐Based Sulfonate Esters: Potent Acetylcholinesterase, Carbonic Anhydrase and α‐Glycosidase Inhibitors

AbstractIn this study, a novel series of sulfonate esters derived from 3‐hydroxyflavone was synthesized and their inhibitory effects on acetylcholinesterase (AChE), α‐glycosidase (AG), and carbonic anhydrase I and II (hCA I and II) enzymes were investigated using experimental and molecular docking analyses. The synthesis involved the reaction of 3‐hydroxyflavone with tosyl chloride, mesytl chloride, β‐naphthylsulfonyl chloride, and 8‐quinolinesulfonyl chloride. The characterization of each compound was confirmed by obtaining 1H NMR, 13C NMR and IR spectra. Furthermore, IC50 and Ki values for the synthesized compounds were calculated and compared to the clinical enzyme inhibitors. Our results showed that the synthesized compounds exhibited inhibition against the targeted enzymes, with Ki values ranging from 1.92 to 4.16 nM for AChE, 32.40 to 55.49 nM for AG, 9.45 to 65.53 nM for hCA I, and 76.62 to 163.33 nM for hCA II. The compound involved quinolinesulfonyl moiety demonstrated especially potent inhibition with IC50 values of 3.96 nM for AChE, 32.40 nM for AG, 9.50 nM for hCA I, and 76.62 nM for hCA II. The docking results aligned well with our experimental findings. The findings have promising implications for the development of novel inhibitors and drug discovery efforts in the future.

Вплив S-естерів тіосульфокислот на окремі біохімічні показники крові щурів

The effect of S-esters of thiosulfonic acids - S-ethyl-4-aminobenzenethiosulfonate (ETS), S-allyl-4-aminobenzenethiosulfonate (ATS) and S-allyl-4-acetylaminobenzenethiosulfonate (AATS) at doses of 50 and 100 mg/kg body weight in rats on some biochemical parameters of protein and lipid metabolism in rats was investigated. The study was conducted in two stages on white male laboratory rats of the Wistar line, weighing 190–210 g. During the first stage of the study, animals of all experimental groups were administered by 500 µL of oil solutions of thiosulfonate esters at 100 mg per kg of body weight for 21 days. In the second stage of the study, the dosage was reduced to 50 mg per kg of body. Throughout both stages of the study, rats were divided into a control group (I) and three experimental groups (II, III, IV), with 5 animals in each. Rats in group II received ETS with their food, while group III received ATS, and group IV received AATS, all in appropriate doses. The animals of the control group were similarly given 500 µL of oil once a day in their diet. After the decapitation of animals, the activities of alanine aminotransferase, aspartate aminotransferase, alkaline phosphatase, concentrations of total protein, urea, cholesterol and triacylglycerols were determined in blood plasma. As a result of the study, it was found that the use of sulfonic acid esters in the studied doses did not have a hepatotoxic effect on rats, as indicated by the normal activity of liver-indicating enzymes (ALT, ALP and alkaline phosphatase) in the blood plasma. In addition, sulfonic acid esters promoted protein synthesizing function, as evidenced by an increase in total protein concentration in the blood plasma and a decrease in urea – the end product of their decomposition. The studied esters had a positive effect on lipid metabolism, which was confirmed by a decrease in the concentration of triacylglycerol and cholesterol in the blood plasma, which, in turn, may contribute to the inhibition of the formation of their complexes in the liver - low-density lipoproteins. Probable changes in the concentration of total protein under the action of ETS and ATS and triacylglycerols under the action of ATS and AATS showed better effects of sulfonic acid esters at a dose of 100 mg/kg compared to a dose 50 mg/kg.

Rapid Biomolecular Trifluoromethylation Using Cationic Aromatic Sulfonate Esters as Visible-Light-Triggered Radical Photocages.

Described here is a photodecaging approach to radical trifluoromethylation of biomolecules. This was accomplished by designing a quinolinium sulfonate ester that, upon absorption of visible light, achieves decaging via photolysis of the sulfonate ester to ultimately liberate free trifluoromethyl radicals that are trapped by π-nucleophiles in biomolecules. This photodecaging process enables protein and protein-interaction mapping experiments using trifluoromethyl radicals that require only 1 s reaction times and low photocage concentrations. In these experiments, aromatic side chains are labeled in an environmentally dependent fashion, with selectivity observed for tryptophan (Trp), followed by histidine (His) and tyrosine (Tyr). Scalable peptide trifluoromethylation through photodecaging is also demonstrated, where bespoke peptides harboring trifluoromethyl groups at tryptophan residues can be synthesized with 5-7 min reaction times and good yields.

INFLUENCE OF THE MIXTURE VISCOSITY ON MECHANICAL ANISOTROPY AND PROCESSABILITY OF AN NBR-BASED RUBBER MIXTURE FOR ADDITIVE MANUFACTURING

ABSTRACT Rubber-based polymers with high carbon black content can be three-dimensionally (3D) printed using the additive manufacturing of elastomers process. However, high-viscosity materials limit printing resolution, making it difficult to produce fine structures and high-precision parts, especially two-component (2K) parts. The viscosity of a rubber compound used for rod seal applications was reduced and adjusted using Nipol® 1312 liquid rubber and the alkyl sulfonic phenyl ester Mesamoll® II as plasticizers to lower the torque level during extrusion when a reduced nozzle diameter of 0.4 mm is used in 3D printing. In addition, the flowability of the compound was enhanced prior to vulcanization of the part, which could increase the layer–layer bond and thus reduce the mechanical anisotropy typically induced by fused filament fabrication. Using a viscosity-optimized rubber compound, a 2K rod seal consisting of a thermoplastic polyurethane with elastomeric properties and an acrylonitrile rubber-based O-ring was produced and dynamically tested for leakage.

Mn(OAc)3-Promoted Sulfonation-ipso-Cyclization Cascade via the SO3- Radical: The Synthesis of Spirocyclic Sulfonates.

A radical sulfonation-ipso-cyclization cascade promoted by Mn(OAc)3·2H2O using functionalized alkynes or alkenes and potassium metabisulfite (K2S2O5) is reported. A total of 30 spirocyclic sulfonates were synthesized under mild conditions. We also demonstrate a modular synthesis approach in multiple steps for the preparation of various azaspiro[4,5]-trienone-based sulfonamides and sulfonate esters.

Molecular simulation and wetting study on the mechanism and capability of hydrophilic surfactants used as spray dust suppressants for dust reduction in coal mines

Coal dust prevention and control has always been a practical problem that needs to be solved urgently in coal mines. Based on spray technology, it has a good application prospect to achieve effective deposition of coal dust by adding surfactants. In this work, the wetting mechanism of three anionic surfactants at the water coal interface was found out from the molecular micro level and macro level through wetting angle test, sedimentation experiment, interfacial tension experiment and molecular dynamics simulation analysis. The results show that the electrostatic potential extremes of sodium sec alkyl sulfonate, sodium fatty acid methyl ester sulfonate and sodium a-alkenylsulfonate are 0.2399 a. u., 0.2430 a. u. And 0.2387 a. u. Respectively, which are greater than the electrostatic potential extremes of water 0.09157 a. u. It can be judged that the head groups of the three surfactants can produce hydrophilicity. The radial distribution function between the S atom and the O atom in the water in the hydrophilic group of the three surfactants has the same overall change trend, forming an obvious first peak and a weak second peak, with molecular diffusion coefficients of 4.633, 11.10, and 14.13 Å2/ps, respectively. The smaller diffusion coefficients correlated with stronger adsorption, which was consistent with contact angle measurements and a relative concentration analysis. The research results can provide reference for efficient evaluation of the wettability of surfactants.

Carbon-Based Solid Acid Catalyzed Esterification of Soybean Saponin-Acidified Oil with Methanol Vapor for Biodiesel Synthesis

In this study, carbon-based solid acids were used to catalyze the esterification of soybean saponin-acidified oil (SSAO) with methanol vapor for the synthesis of biodiesel. The esterification conversion under different conditions was determined, and the catalyst components were determined using acid-base titration, elemental analysis, and inductively coupled plasma spectroscopy. The results showed that the conversion of SSAO under the optimal esterification conditions (i.e., catalyst loading of 6 wt%, methanol/oil molar ratio of 50:1, reaction temperature of 76 °C, and reaction time of 4 h) was 98.9%. The conversion was still higher than 80% after the catalyst was reused for four batches. The methanol vapor esterification (MVE) effectively mitigated the leaching of sulfonic acid groups and the production of sulfonate esters, while the activated white clay adsorption can significantly reduce the metal ion content in SSAO, which weakens its ion exchange with sulfonic acid groups. MVE for biodiesel synthesis is less costly compared to liquid methanol esterification because of the high recovery of methanol and the improved catalyst stability. Therefore, the addition of methanol in the form of vapor in the carbon-based solid acid-catalyzed esterification system is an effective way to maintain the catalyst activity and reduce the production cost of biodiesel.

Photoinduced One‐Electron Oxidation of Estrone Derivatives: A Combined Steady‐State and Time‐Resolved Spectroscopy Investigation

AbstractA detailed investigation of the photophysics and of the redox properties of a set of selected estrone carboxylate and sulfonate esters was carried out by means of steady‐state and time‐resolved spectroscopies. The observed dual fluorescence was assigned to an efficient intramolecular energy transfer from the aromatic moiety to the carbonyl group. On the other hand, the photoinduced monoelectronic oxidation of R−OX in the presence of persulphate anion is followed by mesolytic fragmentation of the so generated radical cation into the corresponding phenoxyl radical with rate constant values (kfrag) of 104–105 s−1, that depend on the X−O bond dissociation energy values.

Emulsion Formation in Palm Oil Methyl Ester Sulfonate Surfactant to Light Crude Oil

The Enhanced Oil Recovery method is a method that can be attempted to increase the recovery of petroleum. One of the materials that can be used is Methyl Ester Sulfonate surfactant from palm oil, as a vegetable surfactant whose raw materials are widely available in Indonesia. In this study, the compatibility test of Methyl Ester Sulfonate surfactant was carried out on light crude oil type T samples. The study was carried out with various surfactant concentrations, starting from 0.25%, 0.3%, 1%, 1.5%, and 2%. In the aqueous stability test, the results obtained for all clear conditions for the surfactant concentration were measured for 3 days in an oven with a temperature of 60oC. Whereas in the phase behavior test, good results of the upper phase emulsion were obtained at concentrations of 0.3%, 1%, 1.5%, and 2%. The volume of the top phase emulsion ranges from 25% to 37.5%. (Normal). From the results of this study, it can be concluded that for the crude oil sample T, palm oil MES surfactant is stable for use as a surfactant injection fluid, with a surfactant concentration composition that produces a fairly large upper phase emulsion of around 25% - 37.5% at a surfactant concentration of 0.5% - 2%.

Initial Analysis of The Characteristics of Sweet Orange (Citrus Sinensis) Peel Essential Oils as an Alternative Surfactant in The Tertiary Oil Recovery Method

Surfactant flooding is one of the types of EOR that reduces the surface tension between two immiscible fluids. The essential oil of sweet orange peel (citrus sinensis) contains a methyl ester group found in the pectin of sweet orange peel, so it has the potential as a raw material for making Methyl Ester Sulfonate by transesterification and sulfonation processes using H2SO4 reactants. This research is focused on testing the MES characteristics of the essential oil of orange peel in the form of density, viscosity, pH, acid number, and compatibility tests. The results of testing the characteristics of the essential oil of sweet orange peel obtained a density of 0.9 g/cm3, a viscosity of 1.36 cP, a neutral pH of 7, and an acid number of 3.048%, so based on these characteristic values the MES of the essential oil of orange peel was included in the initial screening. Alternative MES. Based on the surfactant compatibility test with a concentration scenario of 0.1%, 0.3%, 0.5%, 0.7%, and 1% in brine with a salinity of 15,000 ppm, the best is the 0.1% surfactant scenario. However, all scenarios qualify for compatibility. Certain surfactant solutions are not clear or cloudy, but that does not mean they cannot be injected

Strategy of Choosing Templates in Molecular Imprinting to Expand the Recognition Width for Family-Selectivity.

The class-selective molecular-imprinted polymers (MIPs) have shown the recognition ability to multiple targeted molecules through using one or multiple templates. However, choosing the right templates, the core problem, still lacks a systemic guide and decision-making. In this work, we propose a strategy of selecting templates through expanding the recognition width for the improvement of class-selectivity. First, three families of genotoxic impurity (GTI) were selected as model objects, and the spatial size and binding energy of each GTI-monomer complexes were obtained and compared by computational simulation. The two indexes of energy width (WE) and size width (WL) were introduced to compare the similarity and differences on the two recognition factors, binding strength and spatial size, among these GTIs in each family. Through shortening the width to increase similarity on binding energy and size, the dual templates in the aromatic amines (AI) family and sulfonic acid esters (SI) family were successfully selected. Correspondingly, the prepared dual-template MIPs in the two GTI families can simultaneously recognize all the GTIs comparing with that of single template MIP, respectively. Meanwhile, through comparing the adsorption capacity of the selected template and its analogues in one GTI family, the recognition efficiency of the dual-template MIPs was higher than that of the single-template MIP. This indicates that though using the selected right templates, the higher class-selectivity and the larger recognition width can be realized. Thus, this work can solve the problem of blind template selection, and provide the useful theoretical guidance for designing family-selective molecular imprinting.

Comparing the performances of different sulfonating agents in sulfonation of methyl esters synthesized from used cooking oil

Abstract Methyl ester sulfonate (MES) is considered as an efficient and novel surfactant used as main active ingredient in cleansing products. MES is often produced via sulfonation of methyl ester (ME) with sulfonating agent. In this study, ME was synthesized from used cooking oil (UCO) via transesterification and then sulfonated to produce MES using two different sulfonating agents (chlorosulfonic acid (CSA) and sodium bisulfite (NaHSO3)). The influence of various factors (temperature, sulfonating agent/ME molar ratio and time) on MES yield was investigated. Analysis of optimal MES samples was carried out using different techniques (GC-FID, FTIR and 1H NMR). The maximum MES yield of 88.2 % was achieved with CSA/ME molar ratio of 1.2:1 at 70 °C for 3 h while the highest MES yield of 79.4 % was obtained with NaHSO3/ME molar ratio of 1.2:1 at 90 °C for 3 h. FTIR and 1H NMR analyses revealed the presence of methyl (CH2− asymmetric and CH2− symmetric stretching vibrations), esters (C=O, C–O, and O–CH3), and sulfonate (S=O) groups in MESCSA and MESNaHSO3 samples, thereby affirming the desired product. Surface tension analysis showed that the MESCSA and MESNaHSO3 have low critical micelle concentrations of 0.079 g/L and 0.14 g/L, respectively while the corresponding surface tensions were 51.9 mN/m and 30.94 mN/m for MESCSA and MESNaHSO3 respectively.

Ethene-1,1-disulfonyl Difluoride (EDSF) for SuFEx Click Chemistry: Synthesis of SuFExable 1,1-Bissulfonylfluoride Substituted Cyclobutene Hubs.

We present the synthesis of 1,1-bis(fluorosulfonyl)-2-(pyridin-1-ium-1-yl)ethan-1-ide, a bench-stable precursor to ethene-1,1-disulfonyl difluoride (EDSF). The novel SuFEx reagent, EDSF, is demonstrated in the preparation of 26 unique 1,1-bissulfonylfluoride substituted cyclobutenes via a cycloaddition reaction. The regioselective click cycloaddition reaction is rapid, straightforward, and highly efficient, enabling the generation of highly functionalized 4-membered ring (4MR) carbocycles. These carbocycles are valuable structural motifs found in numerous bioactive natural products and pharmaceutically relevant small molecules. Additionally, we showcase diversification of the novel cyclobutene cores through selective Cs2 CO3 -activated SuFEx click chemistry between a single S-F group and an aryl alcohol, yielding the corresponding sulfonate ester products with high efficiency. Finally, density functional theory calculations offer mechanistic insights about the reaction pathway.

Ethene‐1,1‐disulfonyl Difluoride (EDSF) for SuFEx Click Chemistry: Synthesis of SuFExable 1,1‐Bissulfonylfluoride Substituted Cyclobutene Hubs

AbstractWe present the synthesis of 1,1‐bis(fluorosulfonyl)‐2‐(pyridin‐1‐ium‐1‐yl)ethan‐1‐ide, a bench‐stable precursor to ethene‐1,1‐disulfonyl difluoride (EDSF). The novel SuFEx reagent, EDSF, is demonstrated in the preparation of 26 unique 1,1‐bissulfonylfluoride substituted cyclobutenes via a cycloaddition reaction. The regioselective click cycloaddition reaction is rapid, straightforward, and highly efficient, enabling the generation of highly functionalized 4‐membered ring (4MR) carbocycles. These carbocycles are valuable structural motifs found in numerous bioactive natural products and pharmaceutically relevant small molecules. Additionally, we showcase diversification of the novel cyclobutene cores through selective Cs2CO3‐activated SuFEx click chemistry between a single S−F group and an aryl alcohol, yielding the corresponding sulfonate ester products with high efficiency. Finally, density functional theory calculations offer mechanistic insights about the reaction pathway.

Aminofluorosulfonylation of β,γ-Unsaturated Hydrazones with Sulfur Dioxide and N-Fluorobenzenesulfonimide: Accessing Pyrazoline-Functionalized Aliphatic Sulfonyl Fluorides

An efficient aminofluorosulfonylation strategy was developed for the synthesis of various pyrazoline-functionalized aliphatic sulfonyl fluorides using β,γ-unsaturated hydrazones with sulfur dioxide and NFSI as the starting materials under mild conditions. The sulfonyl fluoride products could be successfully transformed into the corresponding sulfonate esters and amides via the sulfur(VI) fluoride exchange (SuFEx) click reactions. Preliminary mechanistic investigations demonstrate that the reaction operates through a radical cyclization/SO2 insertion/fluorination cascade process.

Artificial Intelligence Techniques and Response Surface Methodology for the Optimization of Methyl Ester Sulfonate Synthesis from Used Cooking Oil by Sulfonation.

Herein, the impacts of sulfonation temperature (100-120 °C), sulfonation time (3-5 h), and NaHSO3/methyl ester (ME) molar ratio (1:1-1.5:1 mol/mol) on methyl ester sulfonate (MES) yield were studied. For the first time, MES synthesis via the sulfonation process was modeled using the adaptive neuro-fuzzy inference system (ANFIS), artificial neural network (ANN), and response surface methodology (RSM). Moreover, particle swarm optimization (PSO) and RSM methods were used to improve the independent process variables that affect the sulfonation process. The RSM model (coefficient of determination (R2) = 0.9695, mean square error (MSE) = 2.7094, and average absolute deviation (AAD) = 2.9508%) was the least efficient in accurately predicting MES yield, whereas the ANFIS model (R2 = 0.9886, MSE = 1.0138, and AAD = 0.9058%) was superior to the ANN model (R2 = 0.9750, MSE = 2.6282, and AAD = 1.7184%). The results of process optimization using the developed models revealed that PSO outperformed RSM. The ANFIS model coupled with PSO (ANFIS-PSO) achieved the best combination of sulfonation process factors (96.84 °C temperature, 2.68 h time, and 0.92:1 mol/mol NaHSO3/ME molar ratio) that resulted in the maximum MES yield of 74.82%. Analysis of MES synthesized under optimum conditions using FTIR, 1H NMR, and surface tension determination showed that MES could be prepared from used cooking oil.

Synthesis, antioxidant, and anticholinesterase activities of novel N‐arylsulfonyl hydrazones bearing sulfonate ester scaffold

AbstractIn this research, two new series of N‐arylsulfonyl hydrazone compounds (14–25) possessing a sulfonate moiety were synthesized and characterized by elemental analysis and various spectroscopic techniques including fourier transform infrared (FT‐IR), 1H‐, and 13C nuclear magnetic resonance (NMR). These compounds synthesized as target molecules (14–25) were tested for their in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition activities and antioxidant potential. The antioxidant capacities of the tested molecules were determined by four different assays. The IC50 values of the screened molecules were determined in the range of 60.14 ± 0.25–84.81 ± 1.09 μM against AChE and in the range of 70.11 ± 0.67–93.60 ± 0.47 μM against BChE. In the AChE assay, 4‐hydroxybenzaldehyde‐based compound 25 (60.14 ± 0.25 μM) showed the highest activity in comparison to rivastigmine (501 ± 3.08 μM). This compound (71.42 ± 0.19 μM) is also one of the compounds with the highest activity against BChE. In the BChE assay, 2‐hydroxybenzaldehyde‐based compound 19 (70.11 ± 0.67 μM) indicated the highest activity in comparison to rivastigmine (19.95 ± 0.20 μM). In antioxidant activity studies, the tested molecules showed lower activities than the standard compounds (butylated hydroxytoluene and α‐tocopherol). Consequently, some novel compounds can be used as potential inhibitor candidates in future studies.

Design, synthesis, crystal structure, and antimicrobial activities of new quinazoline derivatives containing both the sulfonate ester and piperidinylamide moieties.

To discover more efficient antimicrobial agents in agriculture, a series of new quinazoline derivatives bearing both sulfonate ester and piperidine-4-carboxamide moieties were synthesized and assessed for their antimicrobial effects. All of the target compounds were fully characterized by proton (1 H) nuclear magnetic resonance (NMR), carbon-13 (13 C) NMR, and high-resolution mass spectroscopy (HRMS), and compound III-6 containing a 3-bromophenyl substituent was clearly confirmed via single-crystal X-ray diffraction analysis. The bioassay results indicated that some compounds displayed noticeable inhibitory effects in vitro against Xanthomonas oryzae pv. oryzicola (Xoc). Further measurements of median effective concentration (EC50 ) values showed that compound III-17 bearing a 4-methoxyphenyl group had the best anti-Xoc efficacy (EC50 = 12.4 μg mL-1 ), far better than the commercialized bismerthiazol (77.5 μg mL-1 ). Moreover, this compound also demonstrated good protection and curative activities in vivo against rice bacterial leaf streak caused by Xoc. Compound III-17 had a good potential for further development as a new bactericide for controlling Xoc. © 2023 Society of Chemical Industry.

Performance and deactivation mechanism of a carbon-based solid acid catalyst in the esterification of soybean saponin acid oil

In this study, a bamboo charcoal-based solid acid catalyst (BC) was generated by one-step carbonization and sulfonation at 150 °C for 4 h in the presence of sulfuric acid. The BC was characterized by Fourier transform infrared spectrometry, elemental analysis, X-ray powder diffraction, and Brunauer-Emmet-Teller specific surface area analysis. The BC had a specific surface area of 4.54 m2/g, pore volume of 0.0142 cm3/g, and acid density of 1.476 mmol/g. Subsequently, the catalytic activity and deactivation mechanism of the BC in the esterification of soybean saponin acid oil (SAO) and methanol were investigated. The results showed that the conversion yield of esterification reached 98.28% under optimal reaction conditions (i.e., catalyst addition of 10 wt%, methanol/oil molar ratio of 10:1, temperature of 65 °C, and time of 8 h). The conversion yield decreased as reuse batches increased, and was below 80% after three batches. The loss of sulfonic acid groups from the BC occurred mainly in the first esterification batch, caused by residual sulfuric acid leaching and chemical derivatization of sulfonic acid groups. In the second to fourth esterification batches, chemical derivatization was the main reason for deactivation, where the generation of sulfonate esters and exchange of metal cations with hydrogen ions accounted for more than 75% of the chemical derivatization loss. Therefore, without impurity purification of SAO, reducing the amount of sulfonate ester generated on the catalyst was found to be essential for increasing the reuse performance of the BC and reducing the cost of biodiesel production.