Saturated Esters Research Articles

Gold catalyzed intramolecular hydroalkoxylation assisted ring opening of furans to the corresponding saturated γ-keto esters

A facile ring opening of furans in furyl propargyl alcohols to the corresponding saturated γ-keto esters is observed in the gold(III) chloride catalyzed reaction with MeOH. It is found that the ring opening of furan is driven by the intramolecular hydroalkoxylation. Mitigating the intramolecular hydroalkoxylation led to the expected conjugated enyne resulting from the dehydration.

Isobaric heat capacities of ethyl heptanoate and ethyl cinnamate at pressures up to 16.3 MPa

In this work, new experimental values for the isobaric molar heat capacities of ethyl heptanoate and ethyl cinnamate are presented at temperatures ranging from (305 to 387)K and under pressures up to 16.3MPa. The relative expanded uncertainty of the isobaric molar heat capacity is estimated to be less than 1%. The isobaric molar heat capacities of ethyl heptanoate and ethyl cinnamate rise with the increasing temperature and fall with the increasing pressure. Based on the experimental findings in our work and from the literature, the isobaric molar heat capacities of saturated fatty acid methyl esters and fatty acid ethyl esters are found to rise with the carbon number, while the isobaric molar heat capacity of aromatic ester ethyl cinnamate is lower than that of the saturated fatty acid ethyl ester with the same or less carbon number due to the unsaturation. A correlation is proposed for the isobaric molar heat capacities of ethyl heptanoate and ethyl cinnamate with a maximum absolute relative deviation of 0.5%.

Development of a skeletal multi-component fuel reaction mechanism based on decoupling methodology

A new coupled bio-diesel surrogate and primary reference fuel (PRF) oxidation skeletal mechanism has been developed. The bio-diesel surrogate sub-mechanism consists of oxidation sub-mechanisms of Methyl decanoate (MD), Methyl 9-decenoate (MD9D) and n-Heptane fuel components. The MD and MD9D are chosen to represent the saturated and unsaturated methyl esters respectively in bio-diesel fuels. Then, a reduced iso-Octane oxidation sub-mechanism is added to the bio-diesel surrogate sub-mechanism. Then, all the sub-mechanisms are integrated to a reduced C2–C3 mechanism, detailed H2/CO/C1 mechanism and reduced NOx mechanism based on decoupling methodology. The final mechanism consisted of 68 species and 183 reactions. The mechanism was well validated with shock-tube ignition delay times, laminar flame speed and 3D engine simulations.

Conversion of dried Aspergillus candidus mycelia grown on waste whey to biodiesel by in situ acid transesterification

This study reports optimization of the transesterification reaction step on dried biomass of an oleaginous fungus Aspergillus candidus grown on agro-dairy waste, whey. Acid catalyzed transesterification was performed and variables affecting esterification, viz., catalyst methanol and chloroform concentrations, temperature, time, and biomass were investigated. Statistical optimization of the transesterification reaction using Plackett–Burman Design showed biomass to be the predominant factor with a 12.5-fold increase in total FAME from 25.6 to 320mg. Studies indicate that the transesterification efficiency in terms of conversion is favored by employing lower biomass loadings. A. candidus exhibited FAME profiles containing desirable saturated (30.2%), monounsaturated (31.5%) and polyunsaturated methyl esters (38.3%). The predicted and experimentally determined biodiesel properties (density, kinematic viscosity, iodine value, cetane number, TAN, water content, total and free glycerol) were in accordance with international (ASTM D6751, EN 14214) and national (IS 15607) standards.

ChemInform Abstract: Nickel‐Catalyzed Reductive Heck Type Coupling of Saturated Alkyl Halides with Acrylates and Oxabenzonorbornadiene.

The Heck reaction is a well-established transition-metal catalyzed reaction for coupling alkenes with sp2 alkyl halides to give novel unsaturated compounds. Herein we report an analogous Heck-inspired, simple efficient coupling of sp3 alkyl halides with electron-withdrawing alkenes to form reductive coupling products where saturated esters are obtained. A range of acrylates were coupled with sp3 alkyl halides in the presence of Ni(PPh3)2Cl2 catalyst, Zn metal powder, CH3CN solvent, and water, at 80 °C to form the reductive Heck type saturated ester products in good yields. This strategy was further extended to couple oxabenzonorbornadiene with the alkyl halides resulting in ring opening to give rise to bicyclic alcohol products. The mechanism for both the reactions appears to be the usual oxidative-addition driven alkene insertion reaction where the water appears to act as the protonating agent.

Novel Epoxy Resins with Unsaturated Ester Chains Derived from Sodium Lignosulfonate

SummaryNovel epoxy resins with unsaturated ester chains (maleate, M‐series) were synthesized from sodium lignosulfonate and maleic anhydride. Epoxy resins with saturated ester chains (succinate, S‐series) were also synthesized from succinic anhydride. Thermal properties of the obtained epoxy resins were studied by differential scanning calorimetry (DSC) and thermogravimetry (TG). The glass transition temperatures (Tg's) increased with increasing ligosulfonate content in epoxy resins for both M‐ and S‐series. Tgvalues of epoxy resins in M‐series were ca. 15 °C higher than those in S‐series. The activation energies of curing reaction in M‐ and S‐series were ca. 59.6 and 66.1 kJ mol−1, respectively. Thermal degradation temperatures (Td's) were almost constant at 350 °C regardless of lignosulfonate contents in epoxy resins in both M‐ and S‐series. Mass residues at 500 °C increased with increasing lignosulfonate contents in epoxy resins in both M‐ and S‐series.

Influence of the Support Material on the Activity and Selectivity of Ru–Sn–B Catalysts for the Selective Hydrogenation of Methyl Oleate

The influence of the kind of support (Al2O3, SiO2, and TiO2) on the catalytic activity and selectivity of Ru–Sn–B catalysts for the hydrogenation of methyl oleate to oleyl alcohol was studied. The results show that the most active and selective catalyst for producing oleyl alcohol is Ru(1%)–Sn(2%)–B/Al2O3. This was attributed to the catalyst having a favorable surface Sn/Ru ratio (∼2). The SiO2-supported Ru–Sn–B catalyst had a good activity and hydrogenated both C═C double bonds and the C═O group, thus producing stearyl alcohol with a high yield. It however deactivated, to a great extent, its final conversion being lower than that of the bimetallic catalysts supported on Al2O3 and TiO2. The TiO2-supported catalyst had a high selectivity to saturated methyl esters because it hydrogenated C═C double bonds but had little activity for hydrogenation of the C═O group.

Three step auto-tandem catalysed hydroesterification: Access to linear fruity esters from piperylene

A convenient and selective access to saturated hexanoic esters via hydroesterification of piperylene with synthesis gas and methanol is presented. This is the first three step auto-tandem hydroesterification, which is 100% atom economic proceeding under mild conditions. Our optimisations revealed Pd2(dba)3/1,2-dtbpmb as the best catalytic system. Besides, the reaction also tolerates several alcohols, which offers a broad range of fruity esters. In addition, we present insights into the reaction sequence, investigating whether the reaction proceeds via two- or three-step reaction cascade.

Biodiesel Production by Direct In Situ Transesterification of an Oleaginous Tropical Mangrove Fungus Grown on Untreated Agro-Residues and Evaluation of Its Fuel Properties

Recent research has focused on use of waste agro- residues for growth of oleaginous microbial biomass as renewable feedstock for biodiesel. However, pretreatment of lignocellulosic biomass into fermentable sugar is necessary for microbial growth, increasing production costs. An oleaginous fungal isolate from the tropical mangrove wetlands, IBB G4, identified as Aspergillus candidus was assessed for its growth on waste agro-residues viz., banana peel, copra meal, corn cob, grape stalks and sugarcane bagasse,which had not been given any thermo-chemical or enzymatic pre-treatment. The resulting fungal biomass was subjected to in situ (direct) acid transesterification for fatty acid methyl esters (FAME) extraction. Maximal FAME production was obtained on raw untreated banana peel (420 mg/L) and sugarcane bagasse (400 mg/L) with the yields significantly higher (52–68 mg/g of fermented biomass) than those for glucose (32 mg/g). The FAMEs showed major presence of monounsaturated methyl esters (41.7 %; C18:1, C15:1, C17:1, C14:1) and methyl linoleate (C18:2, 36.8 %) and 20 % as saturated fraction when sugarcane bagasse was the substrate for fungal strain. For banana peel, the saturated fatty acid methyl esters (48.6 %; C16:0, C18:0) were abundant, methyl oleate (C18:1, 25 %) was the major monounsaturated fatty ester while methyl linoleate (C18:2, 19 %) and methyl arachidonate (C20:4, 3.8 %) were prevalent as polyunsaturated methyl esters. Biodiesel fuel properties (density, kinematic viscosity, iodine value, cetane number, free and total glycerol) were in accordance with international(ASTM D6751, EN 14214) and national (IS 15607) biodiesel standards, suggesting their suitability as biodiesel fuel.The results in our study indicate the potential suitability of A. candidus IBBG4 biomass grown on raw untreated banana peel and sugarcane bagasse waste and its conversion to FAME by direct in situ acid transesterification. This would help improve process economics for a green and sustainable production of biodiesel.

Abstract 113: Phospholipid Physical State Determines the Efficiency of Cholesteryl Ester Transfer by Cholesteryl Ester Transfer Protein between Discoidal High Density Lipoproteins

The transfer of cholesteryl ester by recombinant cholesteryl ester transfer protein (CETP) between reconstituted discoidal HDL was studied. Particles contained apolipoprotein A-I, unsaturated palmitoyllinoleoylphosphatidylcholine (PLPC), palmitoyloleoylphosphatidylcholine (POPC) or saturated dipalmitoylphosphatidylcholine (DPPC) and cholesteryl ester up to 3 mol% as cholesteryl 1-pyrenedecanoate (CPD) or cholesteryl laurate (CL) in donor and acceptor rHDL, respectively. The concentration dependencies of excimerization upward deviated from a linear dependence, being more curvilinear for DPPC. Separately for DPPC complexes, monomer fluorescence compared to excimer was more efficiently quenched by acrylamide. The nonradiative energy transfer between apoA-I tryptophan residues and CPD molecules was more efficient for PLPC compared to DPPC complexes. Data fulfilled the quenching sphere-of-action model, the sphere with adjacent probe molecules being larger and more distant from apoA-I tryptophan residues in DPPC complexes. CETP-catalyzed cholesteryl ester exchange between donor and acceptor HDL followed by probe excimerization was characterized by a heterogeneous kinetics; the fast exchanging CPD pool was much higher in a case of POPC compared to DPPC complexes. Probe fraction accessible to CETP increased with temperature, suggesting a more homogeneous probe distribution. The noncompetitive inhibition of probe transfer by acceptor particles seems to satisfy the zero off-rate compatible with probe tunneling. The values of V max (0.063 μM·min -1 ) and k cat (0.42 s -1 ) together with a similarity of K m (0.9 μM CPD) and K I (2.8 μM CL) values for POPC-containing rHDL suggest the efficient cholesteryl ester transfer between nascent HDL with unsaturated phosphatidylcholine in vivo opposite to much less efficiency with HDL with saturated phosphatidylcholine. The physical state of phospholipid matrix may underlie CETP activity with discoidal HDL through self-association and location of cholesteryl ester in the bilayer, the availability of cholesteryl ester to cholesterol-binding site in apoA-I structure and the binding of apoA-I-interacting cholesteryl ester to CETP. We are grateful to Dr. A. Tall for providing the recombinant CETP.

Synergistic effect of mixed methanol/ethanol on transesterification of waste food oil using p‐toluenesulfonic acid as catalyst

In this study, inexpensive waste food oil was used as raw material, the p‐toluenesulfonic acid as catalyst, the methanol/ethanol as a transesterification agent to prepare biodiesel was reported. The results indicated that the mixed methanol/ethanol contributed to improving the biodiesel performance. Specifically, when mole percentage of ethanol in the total alcohol was 30%, the yield reached 99.55%, and heating value reached 40.47 MJ/Kg. It was higher than that of single methanol and single ethanol as transesterification agent, respectively. The concentration of saturated fatty acid esters in the biodiesel were also increased by mixed methanol/ethanol as transesterification agent (i.e. increase in the proportion of H in C/H), resulting in higher biodiesel heating value. The mixed methanol/ethanol also showed a good synergistic effect in the biodiesel preparation process. The solubility of ethanol in oil is superior to that in methanol, and ethanol plays a double role of the cosolvent and the transesterification agent. Methanol weakened the drawbacks of the steric effect and emulsification effect of ethanol. This study showed that the methanol can be partially substituted by ethanol. It reduced not only the dependence on methanol, but also the yield and heating value of biodiesel can be increased. © 2015 American Institute of Chemical Engineers Environ Prog, 34: 1547–1553, 2015

Methyl Esters (Biodiesel) from and Fatty Acid Profile of Gliricidia sepium Seed Oil

AbstractIncreasing the supply of biodiesel by defining and developing additional feedstocks is important to overcome the still limited amounts available of this alternative fuel. In this connection, the methyl esters of the seed oil of Gliricidia sepium were synthesized and the significant fuel‐related properties were determined. The fatty acid profile was also determined with saturated fatty acids comprising slightly more than 35 %, 16.5 % palmitic, 14.5 % stearic, as well as lesser amounts of even longer‐chain fatty acids. Linoleic acid is the most prominent acid at about 49 %. Corresponding to the high content of saturated fatty acid methyl esters, cold flow is the most problematic property as shown by a high cloud point of slightly >20 °C. Otherwise, the properties of G. sepium methyl esters are acceptable for biodiesel use when comparing them to specifications in biodiesel standards but the problematic cold flow properties would need to be observed. The 1H‐ and 13C‐NMR spectra of G. sepium methyl esters are reported.

Determination of lipid content of oleaginous microalgal biomass by NMR spectroscopic and GC-MS techniques.

Direct methods based on (1)H NMR spectroscopic techniques have been developed for the determination of neutral lipids (triglycerides and free fatty acids) and polar lipids (glyceroglycolipids/phospholipids) in the solvent extracts of oleaginous microalgal biomasses cultivated on a laboratory scale with two species in different media. The chemical shift assignments observed in the (1)H and (13)C NMR spectra corresponding to unsaturated (C18:N, N = 1-3, C20:3, C20:5, C22:6, epoxy) and saturated (C14-C18) fatty acid ester components in a complex matrix involving overlapped resonances have been unambiguously confirmed by the application of 2D NMR spectroscopy (total correlation spectroscopy and heteronuclear single quantum coherence-total correlation spectroscopy). The study of the effect of a polar lipid matrix on the determination of neutral lipids by an internal reference blending process by a systematic designed experimental protocol has provided absolute quantification. The fatty acid composition of algal extracts was found to be similar to that of vegetable oils containing saturated (C16-C18:0) and unsaturated (C18:N, N = 1-3, C20:N, N = 3-4, C22:6) fatty acids as confirmed by NMR spectroscopy and gas chromatography-mass spectrometry analyses. The NMR methods developed offer great potential for rapid screening of algal strains for generation of algal biomass with the desired lipid content, quality, and potential for biodiesel and value-added polyunsaturated fatty acids in view of the cost economics of the overall cost of generation of the biomass.

Chemical Composition, Antioxidant, Lipid Peroxidation Inhibition and Free Radical Scavenging Activities of Microwave Extracted Essential Oil from Allium sativum

Various chronicle diseases are associated with oxidative stress caused by free radicalsand reactive oxygen species in the living cell system. In the present study, the chemical composition and antioxidant capacity of Allium sativumessential oil (ASEO) were investigated using different scavenging models including 1,1-diphenyl-2-picryl hydrazyl (DPPH), nitric oxide, superoxide, and hydroxyl radicals. Also the ASEO was evaluated for its lipid peroxidation inhibition efficacy, reducing power ability and total phenolic contents. The ASEO was obtained by the hydrodistillation of the dried rhizomes of A. sativum using a microwave-assisted extraction technique. Gas chromatography-mass spectrometry analysis of the ASEO resulted in the determination of 17 different compounds, representing 92.46 % of the total oil. The major components in the ASEO were phenolics, saturated fatty acids, sugar alcohols, esters, hydrazine, quinoline and isoquinoline derivatives along with some other essential phytochemicals. The ASEO showed the antioxidant capacity as the inhibition of DPPH, nitric oxide, superoxide, and hydroxyl radicals by 72.06 %, 79.96 %, 72.66 %, and 71.21 %, respectively. Moreover, the ASEO displayed concentration-dependent reducing power ability and remarkable ferric ion-induced lipid peroxidation inhibitory effect in bovine brain extract. In addition, the ASEO yielded 5.75±0.21 mg/ g gallic acid equivalent phenolic content. The findings of the present study confirm the efficacy of A. sativumas a potential source of natural antioxidant.

Nickel-catalyzed reductive Heck type coupling of saturated alkyl halides with acrylates and oxabenzonorbornadiene

The Heck reaction is a well-established transition-metal catalyzed reaction for coupling alkenes with sp2 alkyl halides to give novel unsaturated compounds. Herein we report an analogous Heck-inspired, simple efficient coupling of sp3 alkyl halides with electron-withdrawing alkenes to form reductive coupling products where saturated esters are obtained. A range of acrylates were coupled with sp3 alkyl halides in the presence of Ni(PPh3)2Cl2 catalyst, Zn metal powder, CH3CN solvent, and water, at 80 °C to form the reductive Heck type saturated ester products in good yields. This strategy was further extended to couple oxabenzonorbornadiene with the alkyl halides resulting in ring opening to give rise to bicyclic alcohol products. The mechanism for both the reactions appears to be the usual oxidative-addition driven alkene insertion reaction where the water appears to act as the protonating agent.

Construction of Skeletal Oxidation Mechanisms for the Saturated Fatty Acid Methyl Esters from Methyl Butanoate to Methyl Palmitate

A series of skeletal oxidation mechanisms for the saturated fatty acid methyl esters (FAMEs) from methyl butanoate to methyl palmitate were developed on the basis of a decoupling methodology with special emphasis on engine-relevant conditions from low to high temperatures at high pressures. When detailed H2/CO/C1, reduced C2–C3, and skeletal C4–Cn submechanisms are introduced, the final mechanism consists of 42 species and around 135 reactions for each methyl ester. Both the high-temperature reactions of the methyl ester moiety and the low-temperature reactions of the aliphatic chain of the ester are included in the mechanism. The skeletal mechanisms were verified against experimental data in shock tubes, jet-stirred reactors, flow reactors, and premixed and opposite flames over the temperatures from 500 to 1700 K at pressures of 1–50 atm from fuel-lean to fuel-rich mixtures. An overall satisfactory agreement between the measurements and computational results was achieved for all of the saturated methyl esters, especially for the large saturated methyl esters with a long aliphatic main chain. The results also indicate that the ignition delay time and the consumption of reactants could be reproduced by employing a skeletal C4–Cn submechanism reasonably well. In addition, the evolution of major products and flame propagation and extinction characteristics were satisfactorily reproduced because the detailed H2/CO/C1 mechanism was used. The compact size makes it easy to integrate the mechanism into multi-dimensional computational fluid dynamics (CFD) simulation.

An experimental and modeling study of the combustion of tetrahydrofuran

Tetrahydrofuran (THF) is a well suited starting point fuel to study the combustion chemistry of saturated cyclic esters that are being considered as promising bio-fuels. To better understand the combustion chemistry of THF, laminar low-pressure premixed flame structure, atmospheric adiabatic laminar burning velocities, and high-pressure ignition delay times were investigated. The structure of laminar premixed low-pressure (6.7kPa) argon-diluted (78%) flames of THF were studied at three equivalence ratios (0.7, 1.0 and 1.3) using on-line gas chromatography analyses. The results consist of temperature and mole fraction profiles (about 40 species) measured as a function of the height above the burner. Ethylene, propene, formaldehyde, acetaldehyde, and dihydrofurans were observed as important intermediates. Aromatic species were detected in very low amounts. The adiabatic laminar burning velocities of THF–air mixtures were measured using the heat flux burner method at atmospheric pressure (initial temperatures from 298 to 398K, at equivalence ratios from 0.55 to 1.60). The maximum burning velocity of THF was comparable to that of ethanol and diethyl ether. The ignition delay times of THF–oxygen–argon mixtures were measured behind reflected shock waves (temperatures from 1300 to 1700K, pressures around 8.5atm, mixtures containing 0.25–1% of fuel for equivalence ratios of 0.5–2.0). A new detailed kinetic model for THF combustion was developed using a combination of automatic generation (EXGAS), Evans–Polanyi correlations (for H-abstraction kinetic data), and CBS-QB3 theoretical calculations (for unimolecular initiation, H-abstraction and β-scission kinetic data). An overall good agreement between simulations and the present experimental results has been found. The main THF reaction pathways under flame conditions have been identified from flow rate analyses.

UV-B辐射增强对拟南芥表皮蜡质的影响

Due to the depletion of stratospheric ozone( O3),the quantity of UV-B radiation reached the earth's surface has increased significantly. Enhanced UV-B radiation influenced plant growth,development and productivity by damaging DNA,RNA,and proteins. Plants are thought to employ a variety of UV-B protective mechanisms,including accumulation of a range of secondary metabolites and adaptive changes in plant morphological features. As the outer surface of aerial plant tissues,the epicuticular wax is believed to play an important role in protecting plants against ultraviolet-B radiation.Epicuticular wax was composed primarily of saturated free fatty acids,aldehydes,alkanes,primary alcohols,secondary alcohols,ketones,and wax esters. Arabidopsis,as a model system to study the genetics and the molecular biology,has the typical structure and composition of cuticle,and it should be a model system to study the ecology of epicuticular waxes.However,little is known as to the responsees of different wax constituents to enhanced UV-B radiation,and the role of epicuticular waxes in providing protection for Arabidopsis from UV-B has not been examined either. Therefore,in the current study,seven wax mutants( CER1,CER3,CER4,CER6,CER10,CER20 and KCS1) and wild type of A. thaliana were selected to analyze the responses of epicuticular wax in crystalloid structure,content and constituents,and wax related gene to UV-B radiation( 50 μW / cm2). The plants accepted UV-B radiation 2 h every day for consecutive 10 days. The resultsshowed that enhanced UV-B radiation altered the crystalloid structure of epicuticular wax on Arabidopsis stems. Under the enhanced UV-B radiation,amounts of pine needle-shaped crystalloids( CER1),columnar-shaped crystalloids and rods( CER3、CER10 and KCS1) decreased significantly. Some small globular-shaped crystalloids appeared on the surface of CER6 mutant. Some irregular plate- and membrane-shaped structures covered the surface of KCS1 and CER10. No significant change of crystalloid types was observed on the stem of the Arabidopsis wild type; however,many horizontal rod and tube crystalloids accumulated in specific zones,which increased the thickness of cuticle. Enhanced UV-B radiation also altered the secretion quantities of wax constituents. Under UV-B radiation,the contents of primary alcohols,fatty acids and aldhydes in Arabidopsis wild type increased significantly,the contents of alkanes,secondary alcohols and ketones decreased significantly,while the contents of total wax changed insignificantly. Under UV-B radiation,the increase of primary alcohols and the decrease of secondary alcohols and ketones were universal in Arabidopsis mutants. Enhanced UV-B radiation upregulated the expression of CER3,CER4 and KCS1,which promoting the accumulation of primary alcohols,fatty acids and aldehydes. The decreased expression of CER1 under UV-B radiation might lead to the reduction of products from alkanesynthesizing branch of the pathway,including alkanes,secondary alcohols and ketones. The decreased expression of WIN1 under UV-B radiation had no effect on the content of total wax,implying that the accumulation of total wax was a result of comprehensive effects of multi genes involved in wax synthesis pathway. Enhanced UV-B radiation shunted wax precursors away from the alkane-synthesizing branch to primary alcohol branch of the pathway.

Ru-Sn-B/Al2O3Catalysts for Selective Hydrogenation of Methyl Oleate: Influence of the Ru/Sn Ratio

This study focuses on the influence of the Ru/Sn ratio on the catalytic hydrogenation of methyl oleate to oleyl alcohol using Ru-Sn-B catalysts, notably on the catalytic activity and selectivity. Sn addition acts positively over the oleyl selectivity by reducing the rates of C=O and C=C saturation but also decreases the global activity. The catalyst with the highest activity and selectivity towards oleyl alcohol is Ru(1%)-Sn(2%)-B/Al2O3. At a low Sn loading (0.5%) the catalyst has high activity for hydrogenation of the carbonyl group and the carbon-carbon double bond. As a consequence stearyl alcohol is produced with high yield. At a high Sn content (4%) the catalyst has lower selectivity to oleyl alcohol due to its low capacity for hydrogenating the carbonyl group. However it has enough activity for hydrogenating the C=C double bonds to produce the saturated methyl ester.

D222 ラーメン残渣汁からのバイオディーゼルの製造(OS5 バイオマス・新燃料・環境技術(2))

This paper describes how to produce a biodiesel from the waste soup of ramen, especially focused on the process of the separation between oil and water and amount of oil in the soup. As a result, from the waste soup with ton-kotsu type the tri-glyceride was gained about 25.7g/L, and biodiesel was produced from this oil by using ordinary alkyl catalyst method. The biodiesel from the waste soup of ramen has low cold flow properties, due to the high content of the saturated fatty acid methyl ester such as C16:0, C18:0 and so on. The amount of BDF from a ramen restaurant is about 2.4L if the customers is around 300 per day, and this means the 9.9kW co-generation system is worked for an hour per day. About energy profit ratio (EPR) analysis, if the oil separation process is modified, EPR will become more than 6.8, and from the waste soup to biodiesel, EPR will be more than 2.8.