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TNG HP DU DIESEL SINH HC T DU M U


Nguyn Vn t1, Lu Cm Lc2, Bi Th Bu Hu1, Dng Kim Hong Yn1, Trn Pht t1, Phm Vn Thanh1, Nguyn Vn Nh1 v L Vn Thc3

ABSTRACT
In this study, a three-step process was developed to produce biodiesel from Calophyllum inophyllum oil. The first step, pre-treatment of feedstock with methanol was done. The second step, acid catalyzed esterification reduces the FFA (Free Fatty Acid) content of the oil to less than 2%. The final step, alkaline catalyzed transesterification process converts the products of the second step to its mono-esters and glycerol. The major factors affect the conversion efficiency of the process such as molar ratio (methanol/oil), amount of catalyst, reaction temperature and reaction duration are analyzed. It has been found that the conversion was over 90% under temperature condition of 60oC, methanol/oil mole ration of 6:1, catalyst amount (catalyst/oil) of 1%, reaction time of 2 hours and agitation speed of 600 rpm (revolutions per minute). Gas Chromatography Mass Spectrometry (GC-MS) analytical result showed that methyl oleate (C18:1) and methyl linoleate (C18:2) were the two major components of Calophyllum inophyllum oilbiodiesel (CaloBDF). The important properties of biodiesel such as gross heat combustion, flash point and kinematic viscosity at 40oC are found out and compared with that of diesel. Keywords: Biodiesel, Calophyllum inophyllum oil Title: Biodiesel production from calophyllum inophyllum oil

TM TT
Mt quy trnh tng hp du diesel sinh hc t du m u gm ba giai on c thc hin trong nghin cu ny. Du m u th c x l s b vi methanol c thc hin trong giai on u tin. Trong giai on hai, qu trnh ester ha xc tc acid nhm lm gim ch s acid ca du m u v gi tr thp hn 2% c tin hnh. Giai on cui cng l qu trnh transester ha xc tc base nhm chuyn sn phm ca giai on hai thnh mono-ester (biodiesel) v glycerol. Nhng yu t quan trng nh hng n hiu sut ca qu trnh tng hp nh t l mol (methanol/oil), hm lng xc tc, nhit v thi gian phn ng c nghin cu. T kt qu nghin cu, hiu sut tng hp t c trn 90% di iu kin nhit 60oC, t l mol 6:1 (methanol/oil), hm lng xc tc 1% (catalyst/oil), thi gian phn ng l 2 gi v tc khuy 600rpm. Kt qu phn tch GC-MS cho thy, methyl oleate (C18:1) v methyl linoleate (C18:2) l hai thnh phn chnh ca du diesel sinh hc tng hp t du m u (CaloBDF). Nhng tnh cht quan trng ca biodiesel nh nhit lng tng, im chp chy v nht ng hc 40oC c phn tch v so snh vi gi tr ca nhng i lng tng ng ca du diesel. T kha: Diesel sinh hc, thnh phn acid bo

1 T VN Bin i kh hu ton cu l mt nguy c, c th tr thnh thm ha cho nhn loi do s tc ng ca n ti nhng yu t c bn ca cuc sng con ngi trn ton
1 2

Khoa Khoa hc T nhin, Trng i hc Cn Th Vin Cng ngh Ha hc ti Tp. H Ch Minh 3 Nevorie Crescent Maroubra, Australia

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th gii. Hng trm triu ngi c th lm vo cnh i ngho, thiu nc, l lt, hn hn,...V vy, c nhng gii php ng ph l iu cn thit. Vic s dng ngun nguyn liu ha thch thi ra mi trng mt lng ln cc kh nh SO2, CO2, NO2,l nguyn nhn gy ra hiu ng nh knh. Chnh v vy vic tm ra ngun nguyn liu thn thin mi trng thay th cho ngun nguyn liu truyn thng l iu ht sc cn thit v cng ng ph vi bin i kh hu l vn ang c quan tm nghin cu nhiu ni trn th gii. Phn ng gia du thc vt hoc m ng vt v mt alcohol vi s c mt ca base mnh to ra nhng hp cht ha hc mi c tnh cht tng t nh du diesel gi l biodiesel (Demirbas, Ayhan, 2009). Biodiesel c th dng trc tip (B100) hoc pha trn vi du diesel vi bt k t l no m khng cn phi thit k li ng c (c bit l thng cha nhin liu). M u thuc h Clusiaceae v c tn khoa hc l Calophyllum inophyllum L. Loi thc vt ny c nhiu ngun gc nh ng Phi, n , ng Nam , Australia v Nam Thi Bnh Dng. Cy cho sn lng 100-200 qu/kg (J. Hemavathy and J. V. Prabhakar, 1990). Lng du c ly ra khong 2 tn/ha trn mi din tch b mt t. Du c mu xanh, c, v c mi hp dn. Theo truyn thng, du m u c s dng nh mt loi thuc iu tr cc bnh l v da, lm x phng, du t n v m phm (C. Morel, 2000; S. Crane, 2005). Mi y, m u c xut nh l mt ngun biomass cho sn xut nhin liu sinh hc (B.K. Venkanna, 2009). n nay c vi cng trnh nghin cu sn xut du diesel sinh hc c cng b (B.K. Venkanna, 2009; Vasanthakumar SathyaSelvabala, 2010). Indonesia cng thnh cng trong vic sn xut v a vo s dng du diesel sinh hc t du m u. Tuy nhin, hu nh cha c thng tin v nghin cu tng hp du diesel sinh hc t du m u ti Vit Nam. Trong nghin cu ny, du m u c s dng lm nguyn liu cho tng hp biodiesel bng mt qu trnh qua ba giai on (1) tin x l nguyn liu u, (2) ester ha xc tc acid v (3) transester ha xc tc base. Cc iu kin phn ng nhm thu c hiu sut ti a c nghin cu. 2 VT LIU V PHNG PHP NGHIN CU 2.1 Vt liu Du m u nguyn liu c mua ti mt c s sn xut c a ch ti phng Hng Li, qun Ninh Kiu, thnh ph Cn Th. Ha cht dng trong tng hp v phn tch c xut x t Merck, c. 2.2 Phng php nghin cu 2.2.1 X l s b du m u nguyn liu vi methanol Du m u nguyn liu v 30% th tch methanol (so vi th tch du) c cha trong phu chit ri lc u khong 1 pht, sau yn phu chit chng 15 pht cho tch lp, ri chit ly lp du pha di, sau em du i un 110C loi b lng methanol v nc cn trong du.
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2.2.2 Tng hp du diesel sinh hc t du M u qua x l s b Du m u sau khi x l s b c FFA cao (19.25) c tin hnh tng hp biodiesel qua hai giai on. Giai on ester ha xc tc acid, cc iu kin phn ng c c nh nh sau: nhit 60oC, thi gian phn ng l 4 gi, tc khuy l 600 vng/pht, phn trm khi lng acid sulfuric so vi du l 1%. Kt qu thu c du M u c FFA bng 1.575 (2%), thch hp tin hnh giai on transester ha xc tc base. Khi lng du m u sau giai on ester ha xc tc acid mi th nghim c dng khng i l 100 gam, khi lng methanol ly theo t l mol (methanol/du) t 4:1 n 10:1, hm lng xc tc thay i t 0.5 n 1.5% (tnh theo khi lng du). Qu trnh th nghim c tin hnh nh sau: cn lng methanol cn thit cho vo bnh tam gic 250 mL. Thao tc cn cn phi nhanh v methanol d bay hi. Sau , cn mt lng xc tc base cn thit. Thao tc cn phi nhanh v KOH d ht m. Cho lng base trn vo bnh tam gic cha sn methanol, do KOH rt kh tan trong methanol nn cn s dng my khuy t khuy. Cn chnh xc lng du cho vo bnh phn ng v t ln my khuy t, iu chnh nhit cn thit. Rt t t dung dch KOH trong methanol vo bnh phn ng trn, tin hnh khuy vi tc mnh to iu kin cho phn ng xy ra nhanh hn v theo di qu trnh phn ng. Sau khi phn ng xong, hn hp phn ng c n nh trong phu chit v tch lp. Sn phm biodiesel c tinh ch bng cch ra nhiu ln vi nc m nhm loi b xc tc, methanol v lm khan bng Na2SO4 khan. 2.2.3 Phn tch tnh cht ha l v thnh phn methyl ester Sn phm biodiesel c phn tch thnh phn ha hc bng sc k kh ghp khi ph GC-MS ti phng th nghim Ha sinh thuc B mn Ha hc, khoa Khoa hc T nhin i hc Cn Th. Bn cnh , mt s ch tiu ha l khc ca sn phm nh: nht ng hc ti 40oC, nhit lng tng, im chp chy c phn tch ti Trung tm Phn tch th nghim CASE chi nhnh ti Cn Th. 3 KT QU V THO LUN 3.1 Nhng tnh cht ha l ca du m u nguyn liu
Bng 1: Tnh cht ha ca du nguyn liu tng hp biodiesel

Thng s FFA*), % nht ng hc 40oC (mm2/s)


*)

Du M u 26.25 60.24

Diesel 3.06

Acid bo t do (Free Fatty Acid hay FFA, g oleic acid/ 100 gam cht bo)

Du m u sau khi trch ly c tin hnh nh gi cht lng thng qua mt s ch tiu ha l c bn. Kt qu c trnh by trong bng 1. Bng 1 cho thy vic s dng trc tip du m u lm nhin liu cho ng c diesel s gp kh khn do mt s l do sau y: nht ca du m ng thc vt cao hn diesel 10-20 ln s lm cho u phun d b tc nghn v qu trnh chy xy ra khng hon ton. khc phc nhng nhc im trn ca du m ng thc vt,
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mt s phng php c p dng nh pha long, nh tng, crcking nhit, hay phng php ha hc nh trao i ester thnh ester ca cc alcohol mch ngn. Phng php ha hc c nghin cu v s dng nhiu nht trong cng nghip v lm gim ng k nht v ci thin tnh bay hi ca du m (Barnwal. B. K, 2005), (Lotero. E, 2006), (Ma. F, 2009). Hm lng ca nc v FFA ng vai tr quan trng trong phn ng trao i este. Khi s dng xc tc base, FFA c trong du m s tham gia phn ng x phng ha vi xc tc lm hao ht v gim tc dng ca xc tc, tng nht ca hn hp phn ng, gy phc tp v tn km cho qu trnh tch thu hi glycerol v ra sn phm. Nhiu tc gi a ra gii hn hm lng FFA (%) c trong du m nguyn liu thch hp cho phn ng transester ha nh Ma v Hanna (< 0,06) (Ma. F, 2009), Ramadhas ( 2) (Ramadhas. A. S, 2005). Du M u sau khi x l s b vi methanol c FFA bng 19.25 (2%). Do , qu trnh tng hp CaloBDF phi qua hai giai on: (1) ester ha xc tc acid nhm chuyn acid bo t do v dng ester lm gim ch s acid v (2) phn ng transester ha xc tc base. Cc nghin cu cn cho thy ngoi du m, cc tc cht cng cn phi c khan nc. Khi hm lng nc ln hn 0.5%, hiu sut c th gim xung di 90% (Canakci. M, 1999). 3.2 X l s b du M u nguyn liu vi methanol Du m u ban u c mu xanh sau khi x l ngm vi 30% th tch methanol th thu c du c mu vng FFA gim khong 25%, mu du sng hn, thun li cho cc bc tip theo trong qu trnh tng hp thnh biodiesel. Tuy nhin, FFA ca du m u vn cn kh cao, nn phi tin hnh ester ha xc tc acid FFA gim n mt gi tr thch hp ( 2%) (Ramadhas. A. S, 2005).

Hnh 1: Du m u ban u FFA = 26.25

Hnh 2: Du m u sau khi x l methanol FFA = 19.25

3.3 Ester ha xc tc acid Cc iu kin giai on ester ha xc tc acid c c nh nh sau: nhit phn ng 60oC, tc khuy l 600 vng/pht, thi gian phn ng l 4 gi, phn trm th tch methanol so vi du l 35%, xc tc acid H2SO4 1%. Kt qu sau giai on ny, FFA ca du m u t 1.575, thch hp tin hnh giai on transester ha. 3.4 Cc yu t nh hng n phn ng transester ha xc tc base Biodiesel l cc mono ankyl ester dn xut t acid bo mch di ca du m ng thc vt c s dng cho ng c diesel. Biodiesel tinh khit gi l B 100 c
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dng trn vi nhin liu diesel theo cc t l khc nhau. Biodiesel ch yu c iu ch t du m bng phn ng transester ha (tranesterification) cn gi l phn ng alcohol gii, hay chuyn v ester. Phn ng transester ha l phn ng thun nghch. Xc tc thng c s dng lm tng vn tc ca phn ng. Alcohol c dng d cn bng lch v pha to ra nhiu sn phm biodiesel. Nhiu cng trnh nghin cu cho thy rng phn ng transester ha ph thuc vo cc thng s (1) loi v hm lng xc tc, (2) loi alcohol s dng v t l mol alcohol/du, (3) nhit phn ng, (4) thi gian phn ng, (5) mc khuy trn, (6) hm lng FFA v nc c trong nguyn liu du m (Sharma. Y. C, 2008), 3.4.1 nh hng ca t l mol methanol/du Alcohol bc nht nh methanol, ethanol, propanol, butanol u c th s dng tng hp biodiesel. Cc biodiesel ny khng khc nhau nhiu v tnh cht ha hc v u th p ng c yu cu ca cc tiu chun nhin liu. Bn cht ha hc ca alcohol nh hng ng k n phn ng tng hp biodiesel. Alcohol c kch thc phn t cng ln th phn ng cng kh xy ra do phn ng thng c tin hnh nhit kh cao. Alcohol phn nhnh phn ng km hn so vi mch thng tng ng. So vi methanol, ethanol c th to hn hp ng ph vi nc nn kh thu hi hn v nc lm cho hiu sut phn ng thp. Nh tng c to thnh trong qu trnh phn ng ca methanol khng bn, d b ph v hn ca ethanol nn thi gian tch pha ngn hn (Zhou. W, 2003). Do , mc d c hn ethanol, ngi ta vn thng s dng methanol lm nguyn liu cho sn xut biodiesel. Mt trong nhng thng s quan trng ca phn ng tng hp biodiesel l t l mol gia alcohol v du. T l ny ph thuc vo bn cht nguyn liu v tnh cht acid, base ng th hay d th ca xc tc. Hiu sut phn ng tng khi t l alcohol/du. Tuy nhin nu s dng qu nhiu alcohol, ha tan glycerol trong alcohol d tng dn n vic tch ra kh khn lm gim hiu sut phn ng. T l mol methanol/du l mt trong nhng yu t quan trng nht nh hng n hiu sut phn ng. Trong nghin cu ny mt lot cc th nghim c thc hin vi t l mol methanol/du thay i t 3:1 n 10:1 v c nh cc yu t cn li nh sau: nhit l 60oC, tc khuy 600 vng/pht. Yu t thi gian c c nh l 2 gi. Kt qu c biu din bng th hnh 3.
100
Hiu sut, %

92.1 83.95

90 80 70 60 50 3

88

86.65

10 11

T l mol (methanol/du)

Hnh 3: nh hng ca t l mol methanol/du n hiu sut tng hp CaloBDF

Theo th hnh 3, theo hng tng t l mol methanol/du th hiu sut cng tng. Khi t l mol (6:1) th hiu sut t cao nht, tuy nhin, nu t l mol cao
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hn (6:1) th hiu sut c khuynh hng gim, iu ny do methanol c nhm OH phn cc ng vai tr nh mt cht nh ha, lm tng kh nng ha tan ca glycerol trong dung dch phn ng. Glycerol cn li trong dung dch phn ng s lm cho cn bng chuyn dch theo chiu ngc vi hng to mono ester, hiu sut s gim. Mt nguyn nhn khc na l do methanol ha tan c c glycerol v alkyl ester, nn mt lng alkyl ester s theo methanol vo trong pha ca glycerol v do hiu sut s gim. 3.4.2 nh hng nhit Vn tc phn ng chuyn ha ph thuc vo nhit . Khi nhit tng, kh nng khuch tn vo nhau ca tc cht tng lm cho phn ng din ra nhanh hn. Khong nhit ca phn ng transester ha tng i rng thng t nhit phng n gn nhit si ca alcohol hoc cao hn na p sut kh quyn. Nhit ti u ca phn ng chuyn ha ph thuc vo bn cht, cht lng ca nguyn liu du m v cc iu kin khc phn ng (Yuan. X, 2008) Trong nghin cu ny alcohol c s dng l methanol (nhit si ca methanol 65oC), nn cc th nghim c tin hnh nm nhit khc nhau 30, 40, 50, 60 v 70oC vi vic c nh cc yu t nh: nng xc tc KOH 1% (theo khi lng du), t l mol methanol/du l 6:1, tc khuy 600 vng/pht, thi gian khong ng l 2 gi. Kt qu c biu din bng th hnh 4.
95.0 90.0 85.0 80.0 75.0 70.0 65.0 60.0 55.0 89.6 82.3 92.1 89.8

Theo th trnh by hnh 4, cho thy hiu sut cao nht t ti 60oC. Khi tng nhit hiu sut phn ng to CaloBDF tng. Tuy nhin, nhit tng cao hn 60oC, th hiu sut phn ng c khuynh hng gim, iu ny c th do phn ng x phng ha du xy ra trc khi hon tt phn ng transester ha. Mt khc, nhit cao dn n tht thot methanol lm gim hiu sut.

Hiu sut, %

30.0 40.0 50.0 60.0 70.0 80.0 Nhit , o C

Hnh 4: nh hng ca nhit n hiu sut tng hp CaloBDF

3.4.3 nh hng ca hm lng xc tc KOH


100 90 81.95 87.95 92.1 90.5 78.5

Hiu sut, %

80 70 60 50 40 0.4 0.6 0.8 1.0 1.2

1.4

1.6

N ng KOH, %

Hnh 5: nh hng ca %KOH n hiu sut tng hp CaloBDF 113

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kho st nh hng ca xc tc KOH, cc th nghim c tin hnh vi nng xc tc KOH thay i t 0.5 n 1.5% (so vi khi lng du) v c nh cc yu t cn li nh sau: nhit 60oC, tc khuy l 600 vng/pht. Yu t thi gian c c nh l 2 gi, t l mol methanol/du l 6:1. Kt qu c biu din bng th Hnh 5. Hiu sut phn ng cao nht khi hm lng xc tc KOH l 1%. nng KOH nh hn 1%, lng xc tc khng phn ng hon tt. Ngc li, khi nng KOH ln hn 1%, hiu sut phn ng c khuynh hng gim bi v khi tng lng xc tc th lm tng lng x phng to thnh, t hiu sut thu sn phm gim. 3.4.4 nh hng ca thi gian Hiu sut phn ng transester ha ph thuc vo thi gian phn ng. Thi gian phn ng cn thit ph thuc vo bn cht nguyn liu v xc tc s dng. Cc nghin cu u cho thy, sau khi phn ng t hiu sut chuyn ha cao nht th vic tip tc tng thi gian s khng lm tng hiu sut. Cc th nghim c tin hnh vi vic c nh cc yu t nh: nng xc tc KOH 1% (theo khi lng du), t l mol methanol/du l 6:1, tc khuy 600 vng/pht, nhit 60oC v thay i yu t thi gian t 30 pht n 180 pht. Kt qu c biu th Hnh 6. Theo th Hnh 6, hiu sut t cao nht thi gian 120 pht, nu thi gian trc 120 pht phn ng xy ra khng hon ton mu ca biodiesel thu c ti hn so vi mu ca biodiesel thu c 120 pht. Tuy nhin, nu thi gian di hn 120 pht, lng biodiesel thu c c khuynh hng gim. Tm li 100 92.1 90.9 Vy iu kin ti u cho phn ng 87.63 84.25 90 transester ha tng hp CaloBDF 80 nh sau: 70 - Hm lng xc tc KOH: 1% (so 60 vi khi lng du) 50 - T l mol methanol/du: 6:1 40 - Nhit phn ng: 60oC 30.0 60.0 90.0 120.0 150.0 - Thi gian: 120 pht Thi gian, pht - Hiu sut cc i: 92.1%
Hnh 6: nh hng ca thi gian n hiu sut tng hp CaloBDF
Hiu sut, %

3.5 Nhng tnh cht ha l ca CaloBDF Bng 2 trnh by nhng tnh cht ha l ca CaloBDF c so snh vi diesel. Nhng tnh cht nh: nht ng hc ti 40oC, im chp chy, ch s acid ca CaloBDF u t yu cu tiu chun JIS, EN, ASTM. Nhit lng tng ca CaloBDF thp hn nhit lng tng ca diesel khong 10%, iu ny do s c mt ca nguyn t O trong phn t methyl ester. im chp chy ca CaloBDF cao hn im chp chy ca diesel tng ng, iu ny s an ton cho vic tn tr v vn chuyn biodiesel.
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Bng 2: Nhng tnh cht l ha ca CaloBDF c so snh vi diesel

Cc tnh cht ha l Ch s acid, mg KOH/g Nhit lng tng, MJ/kg im chp chy, oC nht ng hc 40oC, mm2/s

Cc tiu chun JIS EN ASTM 0.5 0.5 0.5 130 min. 130 min. 130 min. 3.55.0 3.5-5.0 1.9-5.0

CaloBD F 0.310 39.690 140 4.822

Diesel 43.80 76 3.06

3.6 Thnh phn methyl ester acid bo ca CaloBDF Thnh phn methyl eseter acid bo ca CaloBDF c phn tch bng sc k kh ghp khi ph. Kt qu phn tch thnh phn acid bo c tm tt trong bng 3. Thnh phn acid bo ca CaloBDF ch yu l C16 n C20. Thnh phn C18:1 chim nhiu nht (41.19%) v C20:0 tn ti lng vt (0.45%). Hm lng ca a ni i C18:2 chim mt hm lng kh ln (29.07%), nn c kh nng bn oxi ha ca du m u s km.
Bng 3: Thnh phn methyl ester acid bo ca CaloBDF

Tn methyl ester acid bo Acid palmitoleic(C16:1) Acid stearic (C18:0) Acid oleic (C18:1) Acid linoleic (C18:2) Acid eicosanoic (20:0) Methyl ester acid bo bo ha Methyl ester acid bo cha mt ni i C=C Methyl ester acid bo cha nhiu ni i

CaloBDF 15.54 13.75 41.19 29.07 0.45 14.20 56.73 29.07

4 KT LUN tng hp c CaloBDF vi hiu sut 92% quy m phng th nghim theo quy trnh ba giai on. Nhiu c tnh ha l ca sn phm CaloBDF t c yu cu v cht lng theo tiu chun ca ASTM, EN v JIS. TI LIU THAM KHO
Barnwal. B. K, Sharma. M. S, 2005. Prospects of biodiesel production from vegetable oils in India, Renewable and Sustainable Energy Reviews, 9, 363378. B.K. Venkanna, C. Venkataramana Reddy, 2009. Biodiesel production and optimization from Calophyllum inophyllum linn oil (honne oil) A three stage method. Bioresource Technology 100 - 51225125 Canakci. M, Knothe. G, 1999. Biodiesel production via acid catalysis. American Society of Agricultural Engineers, 42(5), 1203-1210. C. Morel, et al. New xanthones from Calophyllum caledonicum, Journal of Natural Products 63, 14711474, 2000. Demirbas, Ayhan, 2009. Biofuels: Securing the Planet's Future Energy Needs. Springer J. Hemavathy and J. V. Prabhakar. Lipid composition of Calophyllum inophyllum kernel, JAOCS 67, 955957, 1990. Lotero. E, Goodwin. J. G, 2006. The catalysis of biodiesel synthesis, Catalysis, 19, 41-83. 115

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Ma. F, Hanna. A, 1999. Biodiesel production: a review, Bioresource Technology, 70, 1-15. Ramadhas. A. S, Jayaraj. S, Muraleedharan. C, 2005. Biodiesel production from high FFA rubber seed oil, Fuel, 84, 335340. Sharma. Y. C, Singh. B, Upadhyay. S. N, 2008. Advancements in development and characterization of biodiesel: A review, Fuel, 87, 23552373. Vasanthakumar SathyaSelvabala, Dinesh Kirupha Selvaraj, Jalagandeeswaran Kalimuthu, Premkumar Manickam Periyaraman, Sivanesan Subramanian, 2010. Two-step biodiesel production from Calophyllum inophyllum oil: Optimization of modified b-zeolite catalyzed pre-treatment. Bioresource Technology. Article in Press Yuan. X, Liu. J, Zeng. G, Shi. J, Tong. J, Huang. G, 2008. Optimization of conversion of waste rapeseed oil with high FFA to biodiesel using response surface methodology, Renew Energy, 33,16781684. Zhou. W, Konar. S. K, Boocock. D. G. V, 2003. Ethyl esters from the single-phase basecatalyzed ethanolysis of vegetable oils, Journal of the American Oil Chemists' Society (JAOCS), 80, 367-371.

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