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Title:	Chemo-enzymatic modification of Jatropha curcas oil for biolubricant and antimicrobial applications
Authors:	Moghaddam Roshanak Rafiee (P51335)
Supervisor:	Jumat Salimon, Professor Dr.
Keywords:	Jatropha curcas Biolubricant Antimicrobial activity Jatropha-biotechnology.
Issue Date:	24-Nov-2014
Description:	High potential of Jatropha curcas plant from two different applications, industrial and biological was investigated. In part one, esters that have been synthesized through two steps reaction include chemo-enzymatic epoxidation reaction and ring opening reaction of oleic acid, and J. curcas seed oil investigated for biolubricant base oil application. Epoxystearic acid (9,10 epoxy octadecanoic acid) was synthesized using immobilized Candida antarctica lipase (Novozyme 435). The optimal conditions for this reaction were confirmed at H2O2 : C=C bonds 4:1 mol, 7 mg/mmol enzyme, temperature 50˚C and reaction time 6 h. Under this conditions, the relative conversion, RCO was 99.5% and 5.5% of OOC. For enzymatic epoxidation reaction of J. curcas seed oil to obtain oil epoxides (JCOE), the OOC obtained was 5.7% at RCO of 93.6%.The oxirane ring opening reaction of epoxystearic acid to obtain monoester 9(10)-hydroxy-10(9)- ricinoleioxy-octadecanoate (HYROA) was done by ricinoleic acid in the presence of ptoluene sulfonic acid (PTSA). At the optimal conditions yield was 86%. For ring opening reaction of epoxystearic acid by sebacic acid to obtain monoester 9(10)- hydroxy-10(9)decanedioxy-octadecanoate (HYSOA) at the optimal condition, the yield was 73.5%. At optimal condition for ring opening reaction of JCOE with ricinoleic acid, yield was 73.7% and using sebacic acid the yield was 69.1%. FTIR results showed ester group in 1735 cm-1 and the results confirmed by peaks at 4.13 ppm in 1 H NMR and 173.56 ppm in 13 C NMR spectra, respectively. HYROA, HYSOA, compounds showed significantly improved in physicochemical properties. Through the branching group at the main chain and increasing the molecular weight of biolubricants had improved the viscosity index (VI), flash point (FP) and oxidative stability (OT) compared to initial material. For HYROA, HYSOA, (as monoester), the VI values were, 127.42, 136.87 and OT values were 220.66, 203.48˚C respectively. For JCOE-Ric and JCOE-Seb (as polyester), the VI were 138 and 134 and OT were 225 and 229˚C respectively. Flash point for products were between 185-223˚C. In part two, synthesis of methylfattyhydroxamic acid (MFHAs) based on Jatropha curcas seed oil was carried out and antimicrobial effects of MFHAs and their two complexes [Cu(II)-MFHs] and [Fe(III)-MFHs] were studied. At the optimal conditions for hydroxylaminolysis the yield of MFHAs was 93.9%. Antimicrobial activity of Cu(II)-MFHs is higher than some commercial antibiotic such as ampicillin, chloramphenicol, against E. coli, and for Fe(III)-MFHs is higher than streptomycin against the E. coli and MFHAs are higher than ampicillin against the S. epidermidis. In general, these two complexes showed higher antimicrobial activity than many commercial antibiotics.,Tumbuhan Jatropha curcas yang berpotensi tinggi daripada dua penggunaan berbeza iaitu industri dan biologi telah dikaji. Pada ujian pertama, ester yang telah disintesis melalui dua tindak balas pengepoksidaan kimia-berenzim dan tindak balas pembukaan gelang asid oleic, dan minyak biji J. curcas telah dikaji bagi kegunaan minyak asas biopelincir. Asid epoxystearic (9,10 asid epoksioktadekanoic) telah disintesis menggunakan Candida antarctica lipase (Novozyme 435). Keadaan optimum bagi tindak balas telah dikenalpasti pada nisbah H2O2 : ikatan C=C, 4:1(mol/mol), 7mg/mmol enzim, pada suhu 50˚C dan masa tindak balas 6 jam. Dalam keadaan ini, penukaran relatif (RCO) adalah 99.5% dan kandungan oksigen oksirana, OOC adalah 5.5%. Bagi tindak balas pengepoksidaan kimia-berenzim minyak J. curcas untuk menghasilkan minyak Jatropha tepoksida (JCOE), nilai OOC adalah pada 5.7% dan RCO adalah 93.6%. Tindak balas pembukaan gelang oxirane bagi asid epoxystearic untuk menghasilkan monoester 9(10)-hidroksi-10(9)-risinoleioksi-oktadekanoat (HYROA) telah dihasilkan oleh asid risinoleik dengan kehadiran p-toluene asid sulfonik (PTSA). Dalam keadaan optimum, hasil adalah sebanyak 86%. Untuk tindak balas pembukaan gelang asid epoxystearic dan asid sebasik untuk menghasilkan monoester 9(10)-hidroksi-10(9)dekanedioksi-oktadekanoat(HYSOA) pada takat optimum hasil adalah sebanyak 73.5%. Pada keadaan optimum tindak balas pembukaan gelang bagi JCOE dengan asid risinoleik, hasil ialah 73.7% dan dengan menggunakan asid sebacic hasil adalah 69.1%. Keputusan spectrum FIIR menunjukkan kumpulan ester di dalam 1735cm-1 dan keputusan ini mengesahkan puncak pada 1HNMR pada 4.13 ppm dan 13CNMR pada 173.56 ppm masing-masing. Sebatian HYROA, HYSOA, menunjukkan peningkatan sifat fizikkimia yang sangat signifikan. Melalui kumpulan percambahan rantaian utama dan dengan meningkatkan berat molekul biopelincir telah memperbaiki indeks kelikatan (VI), takat kelikatan (FP) dan kestabilan pengoksidaan (OT) berbanding bahan asal. Bagi HYROA, HYSOA (sebagai monoester), nilai VI adalah 127.42, 136.87 dan nilai OT ialah 220.66, 203.48 ˚C masing-masing. Bagi JCOE-Ric and JCOE-Seb (sebagai polyester), nilai VI ialah 138 dan 134 dan nilai OT ialah 225 dan 229˚C masing-masing. Titik isyarat produk ialah diantara 185-223˚C. Dalam bahagian kedua, penghasilan asid lemak metilhidrosamic (MFHAs) berasaskan minyak biji Jatropha curcas telah dijalankan dan kesan antimikrobiologi bagi dua kompleks MFHAs, Cu(II)-MFHs dan Fe(III) MFHs telah dikaji. Peratus hasil MFHAs pada keadaan optimum hidrosilaminalisis adalah 93.9%. Aktiviti antimikrobiologi bagi Cu(II)-MFHs adalah lebih tinggi berbanding sesetengah antibiotik komersial seperti ampisilin, kloramfenikol menentang E.coli, dan Fe(III)-MFHs adalah lebih tinggi berbanding ampisilin menentang S.epidermidis. Secara umum, aktiviti antimikrobiologi bagi kedua-dua kompleks ini adalah lebih tinggi berbanding kebanyakan aktiviti antibiotik komersil.,Ph.D
Pages:	171
Call Number:	TP248.27.P55 M637 2014
Publisher:	UKM, Bangi
Appears in Collections:	Faculty of Science and Technology / Fakulti Sains dan Teknologi

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