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Evaluation of biodiesel from ovatum (pili) pulp oil and Psophocarpus tetragonolobus (winged bean) oil

Article in Philippine Agricultural Scientist · September 2007

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The user has requested enhancement of the downloaded file. BiodieselTHE PHILIPPINE from Pili Pulp AGRICULTURA Oil and WingedL SCIENTIST Bean Oil J. P. G. BicolISSN and L.0031-7454 F. Razon Vol. 90 No. 3, 215-221 September 2007

Evaluation of Biodiesel from Canarium ovatum (Pili) Pulp Oil and Psophocarpus tetragonolobus (Winged Bean) Seed Oil

John Paul G. Bicol and Luis F. Razon*

Portion of the M. S. thesis of the senior author. Funded by a grant from the University Research Coordination Office of De La Salle University (DLSU) and the DLSU Science Foundation.

Department of Chemical Engineering, De La Salle University, 2401 Taft Avenue, Manila, *Author for correspondence; e-mail: [email protected]

Biodiesel, or fatty acid methyl esters (FAME) derived from triglycerides of oils of vegetable or animal origin, is an attractive alternative fuel because of its low ecological impact and ease of manufacture. However, some concerns remain about the cost and availability of feedstocks. Studies were con- ducted on biodiesel derived from two novel sources of oil: the pulp of Canarium ovatum (pili) and the seed of Psophocarpus tetragonolobus (winged bean). Oil was extracted from pili pulp and winged bean using hexane. The pili pulp oil and the winged bean oil were found to have a free fatty acid content of 4.0% and 1.0%, respectively. Thus, a combination of acid-catalyzed esterification and base- catalyzed transesterification was necessary to convert the oils to FAME. Pili pulp FAME was found to have a kinematic viscosity of 4.44 mm2s-1, a density of 0.887 g mL-1, cloud point of 7 oC, flash point of 155 oC, free glycerol of 0.01%, total glycerol of 0.06%, acid value of 0.31 mg KOH•g-1, sulfated ash of 0.001%, -1 sulfur of 0.02% and an iodine value of 69 g I2 100g . Winged bean FAME was found to have a kinematic viscosity of 4.93 mm2s-1, density of 0.879 g mL-1, cloud point of 29 oC, flash point greater than 160 oC, free glycerol of 0.02%, total glycerol of 0.07%, acid value of 0.26 mg KOH g-1, sulfated ash of 0.001%, -1 sulfur of 0.02% and an iodine value of 82 gI2 100g . The FAME were found to comply with key standards (ASTM D6751-07, EN14214 and PNS2020:2003) except for the kinematic viscosity of the FAME from winged bean, which was above the maximum limit for the Philippine standard (i. e., PNS2020:2003).

Key Words: biodiesel, Canarium ovatum, fatty acid methyl esters, feedstock, pili, Psophocarpus tetragonolobus, sigarilyas, winged bean

Abbreviations: AOAC – Association of Official Agricultural Chemists, AOCS – American Oil Chemists Society, AR – analytical reagent, ASTM – American Society for Testing Materials, CME – methyl esters, CN – cetane number, FAME – fatty acid methyl esters, FFA – free fatty acid, IV – iodine value, PNS – Philippine National Standard, SN – saponification number

INTRODUCTION gitimate concerns about the impact on vegetable oil prices. Already, a rise in vegetable oil prices has been observed Biodiesel, defined as fatty acid methyl esters (FAME) de- and the usual reason given is the use of oils for biodiesel rived from oils of vegetable or animal origin, has attracted (Anonymous 2007). Hardly a day goes by without a new interest as an alternative to petroleum-derived diesel fuel biodiesel being announced somewhere in the world. (“petrodiesel”). It is biodegradable, renewable, non-toxic Availability is another concern. A simple comparison and carbon-neutral. Compared to other alternative fuels, it of coconut oil production and demand for diesel fuel shows is easy to manufacture and requires only small changes in that coconut oil production can only fill a small fraction of the distribution infrastructure. In blends with petrodiesel, the diesel requirements (Tan et al. 2004). it can be used in unmodified present-day diesel engines. Jatropha curcas (locally known as “tuba-tuba”) has Despite these advantages, there are still some con- been widely promoted as a possible alternative to food oils cerns over the widespread use of biodiesel. Most of the (Foidl et al. 1996; Gubitz et al. 1999). Indeed, it offers the present feedstocks are also food oils. Hence, there are le- advantage that it can be grown on marginal lands. How-

The Philippine Agricultural Scientist Vol. 90 No. 3 (September 2007) 215 Biodiesel from Pili Pulp Oil and Winged Bean Oil J. P. G. Bicol and L. F. Razon ever, both the oil and the seed cake are toxic (Martinez- MATERIALS AND METHODS Herrera et al. 2006). A large spill or a bad poisoning incident could easily turn public opinion against jatropha. Materials A prudent course of action would be to develop other Pili pulp was purchased from Leslie Pili Products, possible sources of feedstocks. Indeed, researchers have City, Sorsogon. The separation of pili pulp (depulping) tried a wide variety of plant oils (Rahman and Raherman was performed by soaking the pili in hot water for 2004; Bouaid et al. 2005; Encinar et al. 1999; Ghadge and about 15 min. Winged bean seeds were purchased from Raheman 2006; Ajue and Obika 2000; Zullaikah et al. 2005; Green World Agri-Farm Center, a supplier of seeds in Ramadhas et al. 2005; Antolin et al. 2002; Usta 2005; Karmee Malate, Manila. Bioactiv® brand coconut methyl esters and Chadhu 2005; Oluwaniyi and Ibeyimi 2003), animal (CME) was purchased from a UniOil gas station in Makati (Zheng and Hanna 1996; Reyes and Sepulveda 2006) and City. even marine algae (Miao and Wu 2006; Chisti 2007). This Analytical reagent (AR) grade hexanes were used for paper describes tests of biodiesel from two new sources of oil extraction from the pulp and the seeds. AR grade metha- oil: the mesocarp (fruit pulp) of Canarium ovatum (“pili”) nol, sulfuric acid and sodium hydroxide were used for the and the seed of Psophocarpus tetragonolobus (“winged esterification and transesterification reactions. bean”, Philippine name: “sigarilyas”). Winged bean was very widely studied in the 1980s, Preliminary Calculations being hailed as the “ of the tropics”. The primary Literature values of the fatty acid profiles of pili pulp oil attraction to the winged bean is its content (30– and winged bean oil (Table 1) were used to calculate key 42%) and yield (2–5 tons per hectare) (De la Peña et al. properties of FAME derived from these two oils. The key 1981). Modest compared to that of coconut, the oil content properties computed were the cetane number, saponifica- of winged bean is similar to that of soybean. Moreover, tion value, iodine value and the viscosity. winged bean oil, though edible, is not very highly valued Cetane number was estimated with the following equa- as a food because of its high behenic acid content. On the tion (Krisnangkura 1986): other hand, the fatty acid profile of its oil seems to indicate 5458 CN = 46.3 + – 0.225 x IV that it may yield biodiesel of acceptable quality. This will SN (1) be discussed further in the next section. Since the primary IV, the iodine value, can be computed from the fatty use of winged bean is its protein, an additional use for its acid profile via the following equation (Kalayasiri et al. oil could make cultivation more economically attractive. 1996): n 254D x Another feedstock that may be studied is the oil from IV = Σ i i (2) i=1 M the mesocarp or the fibrous middle layer of the pili fruit. i The pulp is 33.6% oil, by weight (Coronel 1996). While the where Di, xi and Mi are, respectively, the number of double kernel (commonly called the “”) is also a very rich source bonds, mass fraction and molecular weight of the ith fatty of oil, it is already highly prized as an ingredient in confec- acid. Similarly, SN, the saponification number, may be com- tions, cakes and . On the other hand, the pulp puted through the following equation (Kalayasiri et al. (which makes up 64.5% of the weight of the fruit) is usually 1996): n 560x discarded (Coronel 1996). If the pulp can be used as a source SN =Σ i (3) i=1 M of biodiesel feedstock, a waste stream will have been elimi- i nated. Equation (1) has been very popular, having been used In this paper, key physicochemical fuel properties of in at least six other studies (Encinar et al. 1999; Kalayasiri biodiesel derived from winged bean seed oil and pili pulp et al. 1996; Azam et al. 2005; Karaosmanoglu et al. 2000; oil are determined and compared to biodiesel standards Machacam et al. 2001; Tomasevic and Siler-Marinkovic and predictions from empirical equations. Some observa- 2003). However, only three data points were used to obtain tions are also made on the steps necessary to convert the Equation (1). Hence, any numbers obtained from it should oil to biodiesel. be treated as mere rough estimates.

Table 1. Fatty acid profile of pili pulp oil and winged bean seed oil from literature (wt %).

Source C14:0 C16:0 C16:1 C18:0 C18:1 C18:2 C18:3 C20:0 C20:1 C22:0 C24:0 Reference

Pili pulp 0.10 23.90 4.70 2.6 60.80 6.60 0.8 0.20 0.30 Pham (2004) Winged bean 10.90 4.5 37.10 19.00 3.60 18.50 4.20 Homma et al. (1983)

216 The Philippine Agricultural Scientist Vol. 90 No. 3 (September 2007) Biodiesel from Pili Pulp Oil and Winged Bean Oil J. P. G. Bicol and L. F. Razon

µ The viscosity of the FAME ( m) was estimated using bottom flask with a magnetic stirrer for 1 h at 60 °C. If a an equation by Allen et al. (1999) lower methanol:oil ratio of 20:1 and a lower amount of H2SO4 n (5 wt %) were used, four reaction steps were necessary to µ µ ln m = Σ xi ln i (4) reduce free fatty acid content to below 0.5%. After the i=1 esterification step, the FAME-oil mixture was separated µ where i is the viscosity of fatty acid i and xi is the mass from the methanol-water mixture using a separatory fun- fraction of the ith fatty acid. This equation may be consid- nel. The moisture from the FAME-oil mixture was further ered reliable as its authors showed that it is accurate up to removed using a procedure described in Van Gerpen et al. within ±2%. (2004), in which the procedure is attributed to Keim (1945). The results from these calculations were used to de- Using this procedure, the FAME-oil mixture was dried by termine whether pili pulp oil and winged bean oil are poten- heating to 60 °C for 15 min and then allowed to settle for 24 tially suitable feedstocks for use in biodiesel production. h. After settling, a maximum of 90% of the bottom layer was taken and used as feed for the transesterification reaction. Oil Extraction and Purification A 6:1 methanol-to-oil molar ratio and 1% sodium hydroxide Mechanical pressing of the seeds and pulp was attempted by weight were used to perform the transesterification re- but the amount of oil was very small. Therefore, oil extrac- action in a round-bottom flask. The transesterification was tion was carried out using hexane. The solvent was mixed done at 60 °C for 1 h. The resulting mixture was allowed to for at least 12 h at a 1:1 by weight ratio and was separated separate in a separatory funnel for at least 24 h. The top in a rotary evaporator. Separation was performed at a maxi- layer, which consists of the FAME, was washed with dis- mum temperature of 80 °C. tilled water. Degumming was performed for the oil obtained from winged bean due to the presence of solids believed to be Biodiesel Fuel Testing phospholipids or gums. Degumming was performed by The tests performed on the FAME, the methods used and adding 2% by volume of distilled water and agitating for 30 the laboratories that did the testing are summarized in Table min at 70 °C. The hydrated gums were removed by passing 2. Because the batch size was small (400 mL), the tests on the oils through a filter paper. Two successive degumming the FAME were performed on a composite of four batches steps were sufficient to remove all visible gums present in of pili pulp oil and five batches of winged bean seed oil. the solvent extracted oil. Unfortunately, due to cost considerations and the large sample size required, cetane number testing was not pos- Oil Esterification and Transesterification sible. The free fatty acid content was obtained using Method Ca 5a-40 of the American Oil Chemists Society (AOCS). Both oils were found to have a free fatty acid content greater RESULTS AND DISCUSSION than 0.5%. Hence, an acid-catalyzed esterification reaction was done to reduce the free fatty acid content. A methanol- The results from applying equations (1)-(4) to these fatty to-oil ratio of 40:1 and 10 wt% H2SO4 were used so that the acid profiles are shown in Table 3 along with the relevant free fatty acid content could be reduced below 0.5% in one standards from the European Union (EN14214), the Ameri- step. The esterification reaction was conducted in a round- can Society for Testing Materials (ASTM D6751-07) and

Table 2. Tests, methods and laboratories used for FAME testing.

Test Method Used Laboratory

Density ASTM D1298 De La Salle University Free glycerol AOCS Ca14-56 De La Salle Univeristy Total glycerol AOCS Ca14-56 De La Salle University Acid value (AV) ASTM D974 De La Salle University Kinematic viscosity ASTM D445 Chevron, Philippines, Inc. Flash point ASTM D93 Chevron, Philippines, Inc. Sulfur ASTM D4294 Department of Energy Sulfated ash ASTM D874 Department of Energy Cloud point ASTM D2500 Department of Energy Iodine value AOAC 921.158 (Ch. 41) First Analytical Services Technical Cooperative

The Philippine Agricultural Scientist Vol. 90 No. 3 (September 2007) 217 Biodiesel from Pili Pulp Oil and Winged Bean Oil J. P. G. Bicol and L. F. Razon

Table 3. Predicted FAME properties from fatty acid pro- ues. While the winged bean seed content is similar to files compared with the standards. the literature value, the pili pulp fat content is considerably lower. This may be due to the manner by which the pulp Kinematic Iodine Cetane was separated from the kernel – by soaking in hot water. Viscosity, Value, IV, Number -1 The drastic reduction in the expected oil content of pili 40 °C g I2.(100 g) from mm2sec-1 from Eq. (1) pulp is a potentially important issue if the material is to be from Eq. (4) Eq. (2) used commercially. The free fatty acid content obtained from actual test- Pili pulp 4.33 66 59 ing is similar to that reported in the literature (De la Peña et Winged bean seed 4.46 87 55 al. 1981; PCARRD 1997). Based on the free fatty acid con- ASTM D6751-07 1.9–6.0 - 47 min tent, it was determined that a preliminary acid-catalyzed EN14214 3.5–5.0 120 max 51 min esterification step was necessary. This was carried out in PNS2020:2003 2.0–4.5 - 42 min one step as described in the Methodology. FAME – fatty acid methyl esters Biodiesel Fuel and By-product Testing the Philippine National Standard (PNS2020:2003). Table 3 The fuel test results are summarized in Table 5. Also in- shows that, for the parameters that can be computed via cluded are tests performed on a commercial sample of co- these empirical equations, winged bean biodiesel and pili conut methyl esters (CME) (Bioactiv® brand, Chemrez biodiesel may be expected to be acceptable to these three Corp.). It can be seen that the pili FAME and the winged standards. bean FAME complied with all standards with one excep- tion. Specifically, the viscosity of the winged bean FAME Physicochemical Properties of Oil exceeded the PNS2020:2003 standard although it complied Table 4 shows the fat content and free fatty acid content of with both the ASTM D6751-07 and the EN14214 standards. the raw material and a comparison with the literature val- This may be because the standards agencies are using

Table 4. Fat content of feedstock and free fatty acid content of oil.

Fat Content (%, Dry Basis) Free Fatty Acid Content of Oil (%) Source Actual Literature Actual Literature

Pili pulp 8.0 33.6 (PCARRD 1997) 4.0 4.2 (PCARRD 1997) Winged bean seed 13.1 15-20 (De la Peña et al. 1981) 1.0 2.3 (De la Peña et al. 1981)

Table 5. Summary of fuel property results testing.

Material Specifications Property Pili Winged CME PNS ASTM EN ME Bean ME

Kinematic viscosity (mm2s-1) 4.44 4.93 2.61 2.0 - 4.5 1.9 - 6.0 3.5 - 5.0 Density (g mL-1) 0.887 0.879 0.870 - - 0.86 - 0.90 Cloud point (°C) 7 29 -1 - - - Flash point (°C) 155 160+ 106.5 100 min 130 min 120 min Free glycerol (%) 0.01 0.02 0.01 0.02 max 0.02 max 0.02 max Total glycerol (%) 0.06 0.07 0.11 0.24 max 0.24 max 0.25 max Acid value (mg KOH.g-1 ) 0.31 0.26 0.20 0.5 max 0.8 max 0.5 max Sulfated ash (%) 0.001 0.001 0.001 0.020 max 0.020 max 0.020 max Sulfur (%) 0.02 0.02 0.02 0.05 max 0.15 max 0.10 max . -1 Iodine value (g I2 (100g) ) 69 82 10 - - 120 max

ASTM – American Society for Testing Materials, CME – coconut methyl esters, EN – European Union, ME – methyl ester, PNS – Philippine National Standard

218 The Philippine Agricultural Scientist Vol. 90 No. 3 (September 2007) Biodiesel from Pili Pulp Oil and Winged Bean Oil J. P. G. Bicol and L. F. Razon their “experience base”, that is, standards are based on are reasonable. The rather large error for the kinematic vis- typical results obtained from fuels that are known to the cosity of the winged bean FAME can be explained by the standards agency. Indeed, it can be seen that CME would fact that the viscosity data for the longer chain fatty acids not pass EN14214 because of its very low viscosity though such as behenic acid are not available because they are it is well known to be an adequate fuel in the Philippines. solid at room temperature. Hence, the viscosity of these The high viscosity standard in EN14214 may be because fatty acids was estimated using the viscosity of the clos- the European Standards Agency has probably not had est related fatty acid. enough experience with lower viscosity FAME to conclude that they can indeed be used in diesel engines without any harmful effects. Similarly, the Philippine standards are also CONCLUSION AND RECOMMENDATIONS probably set to a lower viscosity because the Philippine experience is based primarily on coconut. FAME derived from both complied with all stan- The repeatability of the tests for kinematic viscosity, dards with the exception that the winged bean FAME did density, free glycerol, total glycerol, acid value and flash not comply with the PNS2020:2003 kinematic viscosity stan- point were all found to be within the repeatability specifi- dard. Since the winged bean FAME complied with the cations of the tests used. Other properties including sul- ASTM D6751-07 and EN14214, no actual problems are ex- fur, sulfated ash and cloud point were not included since pected from the use of winged bean FAME in diesel en- these tests were contracted to other laboratories; the latter gines. Comparisons of actual measurements with values did not report any trial data. predicted from empirical equations have been shown to be Also worthy of discussion is the cloud point. The within reasonable agreement. cloud point of the winged bean FAME is high and is al- The authors recommend that economic feasibility stud- ready close to room temperature. Hence, some “winteriza- ies be conducted on these materials now that it has been tion” may be necessary if the fuel is to be used in a pure demonstrated that adequate FAME can be obtained from state or a large percentage blend although some loss of these two plants. The production volume of the pili nut material may be the penalty for winterization (Knothe 2005). has shown a steadily upward trend with a peak production Some observations may also be reported on the color of 5402 metric tons of nuts recorded in 2005 (BAS 2007). of the products. The pili pulp FAME is greenish yellow Using the literature value that the fruit contains 64.5% pulp while the winged bean FAME is yellowish red. These prob- and 35.5% nut (Coronel 1996), this figure translates to about ably originate from the natural pigments of the raw materi- 9300 MT of pulp and 3500 MT of oil. This is a modest als. Similarly, the glycerol from pili pulp has a black or dark amount compared to total diesel demand but this volume gray tint while the glycerol from winged bean is light yel- may be enough to sustain a small facility because the pro- low. These observations are relevant because glycerol is duction of pili is concentrated in the and an important by-product of the biodiesel process and a Eastern . significant price premium is paid by end users for colorless The total production of the immature pods of winged glycerine. bean for the past 10 yr has remained roughly constant at about 1800 MT per year (BAS 2007). However, the figure Comparison of Predicted and Actual Results reflects only the use of the plant as a vegetable. Winged A comparison of the model prediction versus actual values bean has a potential yield of about 400–1000 kg of oil per for iodine value and kinematic viscosity is shown in Table hectare (De la Peña et al. 1981). This would rank it on more 6. While not strictly in agreement, the percentage errors or less the same level as soybean and rapeseed but lower

Table 6. Comparison of predicted iodine value and viscosity with the actual value.

Iodine Value Viscosity . -1 2 -1 (g I2 (100g) ) (mm s ) Material Predicted Actual % Predicted Actual % (Eq. 1) Testing Error (Eq. 4) Testing Error

Pili ME 66 69 4.3 4.33 4.44 2.5 Winged bean ME 87 82 6.1 4.46 4.93 9.5

ME – methyl ester

The Philippine Agricultural Scientist Vol. 90 No. 3 (September 2007) 219 Biodiesel from Pili Pulp Oil and Winged Bean Oil J. P. G. Bicol and L. F. Razon than coconut and palm. The economic feasibility of winged The winged bean, a high-protein crop for the tropics. 2nd ed. bean FAME will hinge on both the feasibility of the use of National Research Council (USA). its protein for foods and feed and the use of the oil for fuel. ENCINAR JM, GONZALEZ JF, SABIO E, RAMIRO MJ. As before, the trellis requirement for winged bean works 1999. Preparation and properties of biodiesel from Cynara against the compatibility of this plant with large-scale cardunculus L. oil. Ind Eng Chem Res 38:2927-2931. FOIDL N, FOIDL G, SANCHEZ M, MITTELBACH M, mechanized agriculture. HACKEL S. 1996. Jatropha curcas L. as a source for the Further studies need to be conducted on the winged production of biofuel in Nicaragua. Bioresource Technol bean and pili FAME. 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