Biolubricant Synthesis Research Articles

Biolubricant Synthesis by Additization and Chemical Modification from Lipid-Rich Brackish Coelastrella sp. Using a Biorefinery Approach

Biolubricant Synthesis by Additization and Chemical Modification from Lipid-Rich Brackish <i>Coelastrella</i> sp. Using a Biorefinery Approach

Extending the computational and experimental analysis of lipase active site selectivity.

Molecular docking is an important computational analysis widely used to predict the interaction of enzymes with several starting materials for developing new valuable products from several starting materials, including oils and fats. In the present study, molecular docking was used as an efficient in silico screening tool to select biocatalysts with the highest catalytic performance in butyl esters production in a solvent-free system, an eco-friendly approach, via direct esterification of free fatty acids from Licuri oil with butanol. For such purpose, three commercial lipase preparations were used to perform molecular docking studies such as Burkholderia cepacia (BCL), Porcine pancreatic (PPL), and Candida rugosa (CRL). Concurrently, the results obtained in BCL and CRL are the most efficient in the esterification process due to their higher preference for catalyzing the esterification of lauric acid, the main fatty acid found in the licuri oil composition. Meanwhile, PPL was the least efficient because it preferentially interacts with minor fatty acids. Molecular docking with the experimental results indicated the better performance in the synthesis of esters was BCL. In conclusion, experimental results analysis shows higher enzymatic productivity in esterification reactions of 1294.83μmol/h.mg, while the CRL and PPL demonstrated the lowest performance (189.87μmol / h.mg and 23.96μmol / h.mg, respectively). Thus, molecular docking and experimental results indicate that BCL is a more efficient lipase to produce fatty acids and esters from licuri oil with a high content of lauric acid. In addition, this study also demonstrates the application of molecular docking as an important tool for lipase screening to achieve more sustainable production of butyl esters with a view synthesis of biolubricants.

Branched saturated esters and diesters: Sustainable synthesis of excellent biolubricants

The enzymatic production of biolubricants with desirable properties such as high viscosity index and resistance to oxidation is investigated. These characteristics are ascribed to their branched structure and high molecular weight, as well as, to the absence of unsaturated bonds in the molecule. Solvent-free processes with moderate enzyme concentrations (up to 5% wt.) and reaching conversions of 95% or more, have been conducted. Firstly, up to fifteen branched esters and diesters, all of them saturated, are obtained from a branched acid, 2-methylhexanoic acid, and a variety of linear and branched alcohols and linear diols. Among them, three esters have viscosity indexes close to 200 or higher (1,10-decanediolyl 2-methylhexanoate, 1,12-dodecanediolyl 2-methylhexanoate and 2-octyl-1-dodecanoyl 2-methylhexanoate). For the synthesis of these compounds, optimization of biocatalyst concentration and temperature has been carried out, reaching conversions above 95% within operation times between 2 and 3.5 h.

Green Synthesis and Property Analysis of Biolubricants Based on Structural Variations

Green Synthesis and Property Analysis of Biolubricants Based on Structural Variations

Synthesis and characterization of eco-friendly bio lubricants from plant-based oils

Synthesis and characterization of eco-friendly bio lubricants from plant-based oils

Trimethylolpropane based biolubricant synthesis from sweet almond (Prunusamygdalus dulcis) seed oil for use in automotive applications.

This paper presents a synthesis of a sweet almond oil-based trimethylolpropane biolubricant and the evaluation of its temperature-dependent viscosity properties. The oil was converted into biodiesel by the transesterification process after extraction, refining, and acid-alkaline transesterification. After that, biolubricant was produced by further transesterifying biodiesel with trimethylolpropane at 105 oC at a ratio of 3.9:1 for a 60-minute reaction time with a potassium hydroxide catalyst concentration of 1 wt. %. According to the American Standard Test Methods (ASTM), the biolubricant's pour point and index of viscosity were determined to be 267.50 and -4 oC, respectively. The measured viscosities were 42.80, 30.18, 21.39, 12.25, and 8.90 cSt. cSt at 30, 40, 60, 80, and 100 °C, demonstrating an inverse relationship between temperature and lubricant viscosity. The difference between the FTIR spectra of the biodiesel and the biolubricant—1755.74 cm-1 versus 1743.96 cm-1—verifies the ester group. Sweet almond oil has a higher iodine content than unsaturated glycerides (9.52 g of iodine per 100 g of oil sample) and includes 53.478 % more unsaturated fatty acids than saturated fatty acids, and 71.725 % unsaturated fatty acids for biolubricant according to gas chromatographic data. Linoleic acid made up the majority of the fatty acids in the oil and synthetic biolubricant, with percentages of 31.44 and 45.93 %, respectively. Sweet almond biolubricant and oil contained palmitic, linoleic, and oleic acids. The biolubricant has the potential to function as light gear oil for automobiles because its characterization results correlate favorably with the ISO VG-32 criteria

Optimization of the process variables on biodegradable industrial lubricant basestock synthesis from Jatropha curcas seed oil via response surface methodology

The synthesis of biolubricants from renewable feedstocks is currently gaining attention. Over 95% of the market is comprised of lubricants made from petroleum. Due to their limited biodegradability and high eco-toxicity, lubricants generated from petroleum constitute a significant environmental hazard. As pollution levels increase and oil supplies decline, there is a rising need to develop biobased alternatives. Manufacturing cleaner fuel products will mitigate the negative environmental impact of greenhouse gas emissions, which contribute to global warming. Jatropha curcas seed oil is an efficient renewable feedstock for biolubricant synthesis. This study optimized the process variables on biodegradable lubricant basestock production from J. curcas seed oil. A central composite design was used to maximize the chemical interaction between J. curcas methyl ester and ethylene glycol (EG) as a polyol. A total of 20 experimental runs were done to examine reaction temperature, time, and the ethylene glycol to fatty acid methyl ester (EG-to-FAME) molar ratio. A statistical model indicated that the maximum conversion yield of jatropha biolubricant (JBL) would be 92.48% under the following optimum reaction conditions: 128.95°C, 202.40 min, and ethylene glycol to fatty acid methyl ester (EG-to-FAME) molar ratio of 3.87:1. At these optimum conditions, an average jatropha biolubricant (JBL) yield of 94.12% was achieved under experimental conditions, and this value was well within the range predicted (92.48%) by the model. The quadratic model predicted the biolubricant output (R2 = 0.9919). The synthesized biolubricant met the requirements of Viscosity Grade 46 (ISO VG 46) set by the International Organization for Standardization.

A novel hybrid biocatalyst from immobilized Eversa® Transform 2.0 lipase and its application in biolubricant synthesis

In this study, a Taguchi experimental design was used for optimzing the immobilization of the lipase Eversa® Transform 2.0 (EVS) onto a hybrid support consisting of chitosan (CHI) and agarose (AGA), with glutaraldehyde (GLU) used as the support activator. The biocatalyst obtained was characterized by X-Ray Diffraction (XRD), Fourier Transform Infrared Spectroscopy (FTIR), Thermogravimetry (TGA), Energy Dispersive Spectroscopy (EDS), and Scanning Electron Microscopy (SEM). The optimized reaction conditions (60 min, 5 mM ionic strength, 1% GLU concentration, and 5 mg protein load per g of support) resulted in a highly active biocatalyst (74.39 ± 0.48 U/g) and delivered an immobilization yield of 74.20 ± 0.28%. The biocatalyst produced was observed to lose only 15.3% of its activity after 61 days of storage. The activity was also observed to increase by 96.70% ± 0.76, 27.34% ± 2.34, and 84.35% ± 1.68 in the presence of the organic solvents hexane, cyclohexane, and methanol, respectively. Additionally, the byocatalist showed more pronounced activity at temperatures above 50 °C and was still able to retain approximately 30% of it at 70 °C. These values were found to be higher at alkaline pHs, as the activity of Eversa® 2.0 Transform saw an increase of up to 140% at pH 9. The desorption tests performed did not reveal any enzymatic detachment from the support. The novel biocatalyst also showed promising ester-lubricating properties. Furthermore, the in silico study revealed a binding affinity of −5.1 kcal/mol between oleic acid and the enzyme, suggesting that the combination of the substrate and the lipase was more stable and therefore, suitable for esterification.

Chemical transformation of Jojoba oil and Soybean oil and study of their uses as bio-lubricants

Bio-based lubricants have traditionally piqued interest as a supplement to mineral oil-based lubricants in response to rising environmental pollution concerns and declining petroleum assets. This paper discussed the synthesis of bio-lubricants from vegetable oils such as soybean (SOY), and jojoba (JOJ) oil using chemical transformation methods such as epoxidation of the carbon-carbon double bonds in the structure of their already high resistance to air oxidation using a combined catalyst of Amberlite IR 120 and peroxide catalyst with high yield (80 %), followed by transesterification, ring-opening of vegetable oils, and finally acetylation of the hydroxylated obtained products. The rheological and tribological characteristics of the compounds produced were examined to validate their suitability as bio-lubricants using FT-IR, 1H NMR, and TGA techniques. These results demonstrate the possibility of an environmentally sustainable method for producing bio-lubricants.

A stepwise docking and molecular dynamics approach for enzymatic biolubricant production using Lipase Eversa® Transform as a biocatalyst

Biolubricants have gained a notable market share in the last decade due to the increased interest in replacing petroleum-based lubricants in various applications. Biolubricants are produced by using renewable raw materials such as vegetable oils, and enzymes such as lipases . The latter can be used as catalysts for biolubricant synthesis, which renders these processes environmentally friendly. Among the several innovations enabled by enzymatic engineering tools, the lipase Eversa® Transform 2.0 stands out as a genetically-modified and low-cost enzymatic formulation that has shown high activity in the production of biodiesel , fatty acids, and biolubricants. In addition to enzymatic engineering, advanced computational tools, such as docking and molecular dynamics, can also be powerful allies in the development of competitive products that impart low negative impact in the environment. These simulation tools enable the elucidation and understanding of reaction mechanisms, cut reagent costs, and inform choices regarding materials and conditions to be used in related industrial processes. Thus being, this work proposed the analysis and modeling of the synthesis reactions of biolubricants derived from oleic acid via the use of n-octanol and isoamyl alcohol, with lipase Eversa® Transform 2.0. Molecular dockings showed that the predominant interactions between the ligands and the amino acid residues that make up the active site of the enzyme and its surroundings were of Van der Waals and hydrophobic nature. Through simulations via molecular dynamics, it was found that these interactions were responsible for the stability of the lipase-ligand complex, given the low number of hydrogen bonds formed during the simulations. Furthermore, the low variation in the position of the lipase-ligand complexes comparatively to their initial conformations over the production stages attested that the chosen docking poses were adequate to describe the ligand conformations in the region of the active sites of the enzyme. These results also provide a structural view of the interactions between lipase Eversa® and the fatty esters used as lubricants, and confirm the potential in the use of these alcohols in this process. Finally, an in vitro validation showed improved results of esterification activity of the lipase with isoamyl alcohol. This hinted that the substrate that was in closer conformation and that showed shorter and more stable hydrogen bonds with the active sites of the enzyme demonstrated better use potential for the biolubricant production system that has been proposed. • The synthesis of biolubricant was evaluated through docking and molecular dynamics studies. • Most interactions of the lipase-ligand complex are Van der Waals or hydrophobic. • The interactions provided the stability of the lipase-ligand complex. • Docking positions exposed the conformations of the ligands in the lipase active site.

Esters from castor oil functionalized with aromatic amines as a potential lubricant

AbstractVegetable oils are very promising alternatives to fossil lubricants due to their abundance, low cost, excellent performance, and environmental friendliness. Due to its multifunctional structure, castor oil is an excellent precursor in the synthesis of new biolubricants. However, it showed poor thermal‐oxidative stability and a higher pour point. This study used castor oil fatty acids prepared by transesterification (EHRO), epoxidation (TEPO), and oxirane ring opening with the aromatic amines aniline (ANIL) andp‐anisidine (ANIS). The chemical structure of these oils was verified by1H and13C NMR analysis, and mass spectrometry. Measurements show that the presence of an aromatic amine increases the viscosity resulting in 172 (ANIL) and 199 (ANIS) cSt at 40°C, but reduces viscosity index to 16 and 1, respectively. In addition, the amine groups can scavenge radicals increasing their thermal and oxidative stability. These products do not oxidize copper, and tribological analysis reveals that ANIS has the lowest torque with wear equivalent to commercial mineral lubricant NH‐140.

Transesterification of methyl oleate for sustainable production of biolubricant: Process optimization and kinetic study

Trimethylolpropane fatty acid triester (TFATE) is a promising biolubricant as an environmentally friendly substitute to conventional mineral-based lubricants. However, the issues of extensive energy consumption from vacuum maintenance and feedstock saponification caused by strong alkaline catalysts exist in current TFATE-based biolubricant synthesis. Here, sustainable production of biolubricant was achieved with methyl oleate (MO) from non-edible oil sources as the feedstock and moderate alkaline K2CO3 as the catalyst. Nitrogen gas stripping method instead of vacuum was adopted for methanol removal. The effects of agitation speed, N2 flow rate, catalyst amount, MO to trimethylolpropane (TMP) molar ratio and temperature on MO conversion and TFATE selectivity were examined. The TFATE selectivity reached 95.6% under the optimized conditions. Leaching tests indicated neglectable K2CO3 dissolution in reaction products. The kinetic parameters for the three consecutive transesterification reactions were calculated. In addition, the synthesized biolubricants exhibit low acid value and volatility, moderate iodine value, superior thermal stability, and good rheological and frictional properties.

Biolubricant production via esterification and transesterification processes: Current updates and perspectives

The growing concern and limitations for existing lubricants have driven the need for biolubricants, extensively proposed as the most suitable and sustainable lubricating oils. Biolubricants are generally synthesized from various bio-based sources, including vegetable oils, microbially derived oils, waste cooking oil, etc. They are promising commodities and advantageous to mineral-based analogues due to their exceptional properties like their lubricity, biodegradability, reduced toxicity, and reduced volatility. Yet, their utilization as lubricants is constrained due to their relatively poor cold-flow and thermo-oxidative stability uncertainties even after being chemically modified. Hence, many chemical modification pathways have been reported to overcome this limitation, with the most exploited approaches being esterification and transesterification. This modification pathway enhanced the thermo-oxidative stability and the cold-flow properties of these bio-based oils, increased the yield, and enhanced the quality of the lubricants. With this in mind, this paper reviews up-to-date works conducted in this area and critically report the advancement in esterification and transesterification production of biolubricants. The study further reviews the latest published literature, current updates, and future perspectives related to the synthesis of biolubricants. Also, the review highlights the significant factors that govern the entire reaction process, selection criteria of renewable feedstocks, and the tribological performance of biolubricants.

Synthesis of Novel Biolubricants from Waste Cooking Oil and Cyclic Oxygenates through an Integrated Catalytic Process

Synthesis of Novel Biolubricants from Waste Cooking Oil and Cyclic Oxygenates through an Integrated Catalytic Process

The Catalysed Transformation of Vegetable Oils or Animal Fats to Biofuels and Bio-Lubricants: A Review

This review paper summarizes the current state-of-the-art of the chemical transformation of oils/fats (i.e., triacylglycerols) to the use of biofuels or bio-lubricants in the means of transport, which is a novelty. The chemical transformation is necessary to obtain products that are more usable with properties corresponding to fuels synthesized from crude oil. Two types of fuels are described—biodiesel (the mixture of methyl esters produced by transesterification) and green diesel (paraffins produced by hydrogenation of oils). Moreover, three bio-lubricant synthesis methods are described. The transformation, which is usually catalysed, depends on: (i) the type and composition of the raw material, including alcohols for biodiesel production and hydrogen for green diesel; (ii) the type of the catalyst in the case of catalysed reactions; (iii) the reaction conditions; and (iv) types of final products. The most important catalysts, especially heterogeneous and including reaction conditions, for each product are described. The properties of biodiesel and green diesel and a comparison with diesel from crude oil are also discussed.

Enzyme-catalyzed synthesis and properties of polyol ester biolubricant produced from Rhodotorula glutinis lipid

Biolubricants do not cause the environmental pollution resulting from the manufacturing and use of mineral-based lubricants, but the commonly adopted chemical method of preparing biolubricants using expensive vegetable oils as raw materials is still environmentally and economically unsatisfactory. In this study, R. glutinis lipid with a high oleic-acid content was esterified with trimethylolpropane (TMP) by using the Candida sp. 99–125 enzyme in a solvent-free system, and the effect of the microbial oil with the high oleic-acid content on the performance of resulting biolubricants was investigated. The purpose of this study was to solve the problems of pollution caused by the chemical synthesis of biolubricants and of the uneconomical use of vegetable oils as raw materials. Further, this study aimed to improve the performance of biolubricants by using the microbial lipid with a high oleic-acid content. As a result of optimization of the reaction conditions, the yield of trimethylolpropane fatty acid triester (TFAT) reached 89.5%. The synthesized biolubricants had excellent low-temperature lubrication performance (pour point=−45 °C), and the physicochemical performance reached the ISOVG-46 grade. The results of the high-frequency reciprocating friction test (HRFT) show that the products have better tribological properties than mineral-based lubricants of the same viscosity grade (friction coefficient=0.085; average wear scar diameter=187 µm).

RSM and Artificial Neural Networking based production optimization of sustainable Cotton bio-lubricant and evaluation of its lubricity & tribological properties

Depletion of mineral reservoirs along with health and environmental concerns have led to a greater focus on bio-lubricants. The purpose of this study was to analyze and optimize the reaction conditions of the transesterification process for cotton biolubricant synthesis by using Response Surface Methodology (RSM). In RSM, Rotatable central composite design was selected to examine the effect of reaction input factors on the yield of cotton bio-lubricant during the transesterification process. ANOVA analysis showed that temperature was the most significant factor followed by time, pressure and catalyst-concentration. Optimum reaction conditions obtained by RSM for maximum TMP tri-ester (cotton bio-lubricant) yield of about 37.52% were 144 °C temperature, 10 h time, 25 mbar pressure, and 0.8% catalyst-concentration. RSM predicted results were successfully validated experimentally and by artificial neural networking. About 90%–94% cotton seed oil bio-lubricant was obtained after purification and its physiochemical, lubricity and tribological properties were evaluated and found comparable with ISO VG-46 and SAE-40 mineral lubricant. Hence, cottonseed oil is a potential source for the bio-lubricant industry.

A review on bio-lubricant production from non-edible oil-bearing biomass resources in Iran: Recent progress and perspectives

Lubricants are among the largest drivers of global oil demand in the world. The negative environmental impacts resulting from the entry of direct mineral lubricants necessitates the application of bio-lubricants as an excellent alternative to mineral lubricants. The main resources of bio-lubricants are edible/non-edible oils. The use of edible oils as the primary feedstock for bio-lubricant production in developing countries like Iran is being faced with several controversial challenges including the high dependence of the country to edible oils import, the high price of edible oils, the crisis of food shortage, and the negative impact of edible oils on energy security. The application of non-edible oils as a sustainable bio-lubricant resource plays a critical role in lubricant industries. This review provides an overview on bio-lubricant production with a description of various kinds of non-edible feedstocks. A detailed description of different non-edible resources in Iran (e.i. castor, jatropha, microalgae, waste oil/fat, bitter almond, ailanthus, camelina, and waste fish oil) including the characterization, distribution, climate, and quality analysis are presented. Various kinds of chemical modification methods focused on improving the quality of bio-lubricants have been also discussed. This review delivers a comprehensive overview of bio-lubricant synthesis by discussing applications, recent trends, and challenges in this field. The information provided in this study can be of assistance with the researchers and experts involved in the lubricant industry take an effective step to address the challenges ahead in the cleaner lubricants production by relying on sustainable oily resources. Overall diagram. • Recent advances in bio-lubricants production and applications were discussed. • Potential non-edible oils in Iran were introduced for bio-lubricant production. • Non-edible oils have the potential for practical application in engineering systems. • Waste oil/fats have a promising prospect for bio-lubricant production.

Immobilization of Eversa® Transform via CLEA Technology Converts It in a Suitable Biocatalyst for Biolubricant Production Using Waste Cooking Oil.

The performance of the previously optimized magnetic cross-linked enzyme aggregate of Eversa (Eversa-mCLEA) in the enzymatic synthesis of biolubricants by transesterification of waste cooking oil (WCO) with different alcohols has been evaluated. Eversa-mCLEA showed good activities using these alcohols, reaching a transesterification activity with isoamyl alcohol around 10-fold higher than with methanol. Yields of isoamyl fatty acid ester synthesis were similar using WCO or refined oil, confirming that this biocatalyst could be utilized to transform this residue into a valuable product. The effects of WCO/isoamyl alcohol molar ratio and enzyme load on the synthesis of biolubricant were also investigated. A maximum yield of around 90 wt.% was reached after 72 h of reaction using an enzyme load of 12 esterification units/g oil and a WCO/alcohol molar ratio of 1:6 in a solvent-free system. At the same conditions, the liquid Eversa yielded a maximum ester yield of only 34%. This study demonstrated the great changes in the enzyme properties that can be derived from a proper immobilization system. Moreover, it also shows the potential of WCO as a feedstock for the production of isoamyl fatty acid esters, which are potential candidates as biolubricants.

Comparative Study of Methods of Chemical Modification of Dehydrated Castor oil for Synthesis of Biolubricant

Vegetable oil blends are the emerging alternative feedstocks, which are being used to synthesize environment friendly lubricants. This work focuses on the Comparison of the methods of chemical modification, which are used for the biolubricant synthesis and also compares the resultant behaviour characterized on their thermal stability and viscosity. The biolubricant products are synthesized using two chemical modification methods. Method 1: Epoxidation of vegetable oil followed by transesterification of epoxidized oil. Method 2: Preparation of methyl esters (Transesterification) followed by epoxidation of methyl esters. Biolubricant derived from method 1 shows better thermal stability (Tonset = 338 ºC) compared to method 2 (Tonset = 205 ºC). The viscosity indices and pour point values of the products were found to be 222; 4.6 ºC and 216; 6.0 ºC, respectively. Thus, the biolubricant derived from first method showed better physio-chemical properties and were comparable and a blend of non edible oil and waste cooking oil acts as potential basestock for biolubricant synthesis.