Catalytic epoxidation of methyl linoleate

Du, Guodong; Tekin, Aziz; Hammond, Earl G.; Wood, L. Keith

doi:10.1007/s11746-004-0926-3

Cited by 65 publications

(44 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Nevertheless, many heterogeneous catalysts and enzymes have been suggested and employed to augment the effects of organic acids and hydrogen peroxide to enhance the yield. It was also found that peroxy formic acid was more efficient than peroxy acetic acid (Du et al, 2004, Mungroo et al, 2008.…”

Section: Introductionmentioning

confidence: 96%

“…Traditionally, an organic acid such as acetic or formic acid is used with hydrogen peroxide to generate per oxyacid as the oxygen carrier for the epoxidation of oils and fatty acid alkyl esters (Du et al, 2004). These per oxyacids can be employed as a separate reagent or can be synthesized insitu, but the most common method is the in-situ generation of peroxy acid.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Epoxidation of methyl esters derived from Jatropha oil: An optimization study

Mushtaq¹,

Tan²,

Nadeem³

et al. 2013

Grasas y Aceites

View full text Add to dashboard Cite

RESUMEN Epoxidación de ésteres metílicos derivados del aceite de Jatropha: Optimización del estudioSe ha evaluado la optimización de la reacción de epoxidación de ésteres metílicos obtenidos a partir de aceite de Jatropha. Se ha empleado para el diseño experimental una metodología de superficie de respuesta (RSM), basada en un diseño compuesto central giratorio (CCRD). Cuatro variables de la reacción fueron evaluadas: relación molar peróxi-do de hidrógeno/C=C, relación molar ácido fórmico/C=C, temperatura de reacción y tiempo de reacción. Las condiciones óptimas de epoxidación calculadas por el modelo cuadrático fueron 3.12 moles de peróxido de hidrógeno/C=C moles, 0.96 moles de ácido fórmico/C=C moles, una temperatura de reacción de 70.0 °C y un tiempo de reacción de 277 minutos. Una reacción optimizada mediante los parámetros propuestos del proceso proporciona un rendimiento de 92.89 ± 1.29% en peso con un tiempo de reacción relativamente mejorado. La concentración de peróxido de hidrógeno y la temperatura de la reacción fueron las variables más significativas, además la temperatura de la reacción y la concentración de peróxido de hidrógeno mostraron fuertes interacciones. Los ésteres metílicos epoxidados se analizaron mediante FT-IR, 1H RMN y RMN de 13C. Este estudio indica que se requiere una proporción molar relativamente mayor de ácido fórmico que la propuesta en la literatura. PALABRAS CLAVE: Aceite epoxidado de JatrophaCaracterización -Metodología de superficie -Optimización -Respuesta. SUMMARY Epoxidation of methyl esters derived from Jatropha oil: An optimization studyThe optimization of the epoxidation reaction of methyl esters obtained from Jatropha oil was appraised. Response surface methodology (RSM) based on a central composite rotatable design (CCRD) was employed for the experimental design. Four reaction variables namely hydrogen peroxide/ C=C mole ratio, formic acid/C=C mole ratio, reaction temperature and reaction time were evaluated. The optimum epoxidation conditions calculated by the quadratic model were 3.12 moles of hydrogen peroxide/C=C moles, 0.96 moles of formic acid/C=C moles, a reaction temperature of 70.0 °C and a reaction time of 277 minutes. A reaction optimized by the proposed process parameters provided a yield of 92.89 ± 1.29 wt.% with relatively improved reaction time. Hydrogen peroxide concentration and reaction temperature were found to be the most significant variables while reaction temperature and hydrogen peroxide showed strong interactions. The epoxidized methyl esters were analyzed using FT-IR, 1 H NMR and 13 C NMR techniques. This study suggested relatively higher molar ratio of formic acid required than was proposed in the literature.

show abstract

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Epoxidation of methyl esters derived from Jatropha oil: An optimization study

Mushtaq¹,

Tan²,

Nadeem³

et al. 2013

Grasas y Aceites

View full text Add to dashboard Cite

show abstract

“…The signal at 7.27 ppm referred to the solvent D 2 O for LA, MEOA and diepoxide LA [7]. Indeed, it appears that the signals were present in the MEOA, as four peaks of roughly equal intensity (132.89, 132.72, 130.15, and 124.02 ppm) were observed in the alkenic carbon region in the 13 C-NMR spectrum, [5], while they had disappeared in the di-epoxide LA.…”

Section: Ftir Analysis Of Meoamentioning

confidence: 96%

“…Increasing the temperature up to 60 °C also improved the rate of epoxide formation. The monoepoxidation of methyl linoleate was examined using transition metal complexes as catalysts [5]. With a catalytic amount of MTO (4 mol%) and pyridine, methyl linoleate was completely epoxidized by aqueous H 2 O 2 within 4 h. Longer reaction times (6 h) were needed with 1 mol% catalyst loading.…”

Section: Introductionmentioning

confidence: 99%

Epoxidation Synthesis of Linoleic Acid for Renewable Energy Applications

Abdullah¹,

Yusop²,

Salimon³

et al. 2016

MJAS

View full text Add to dashboard Cite

Monoepoxidation linoleic acid (MEOA) has advantages for industrial applications. MEOA was synthesized using immobilized Candida antarctica lipase (Novozym 435 ® ). At optimum conditions, higher yield (82.14 %) and medium oxirane oxygen content, OOC (4.91 %) of MEOA were predicted at 15 µL of H 2 O 2 , 120 mg of Novozym 435 ® and 7 hours of reaction time. Fourier Transform Infrared Spectroscopy (FTIR) spectra of the MEOA showed monoepoxide group at 820 cm -1 . 1 H NMR analysis confirmed the monoepoxide group at 2.92 -3.12 ppm while the monoepoxide signals of 13 C NMR appear at 54.59 -57.29 ppm. LC-MS analysis shows that of MEOA gives m/z at 296.22 as final product. MEOA exhibited good pour point (PP) of -41 ºC. Flash point (FP) of MEOA increased to 128 ºC comparing with 115 ºC of linoleic acid (LA). In a similar fashion, viscosity index (VI) for LA was 224 generally several hundred centistokes (cSt) more viscous than MEOA 130.8. MEOA was screened to measure their oxidative stability (OT) which was observed at 168 ºC. It is evident that increasing the hydrogen peroxide amount has a strong effect on the reaction kinetics; however, a large excess of hydrogen peroxide results in accumulation of peracid in the final product. Keywords: linoleic acid, Novozym 435® , self-epoxidation, renewable energy Abstrak Mono-pengepoksidaan asid linoleik (MEOA) mempunyai kelebihan untuk aplikasi industri. MEOA telah disintesis menggunakan Candida Antartika lipase (Novozym 435 ®) pegun. Pada keadaan yang optimum, peratus hasil MEOA sebanyak 82.1 % dengan kandungan oksigen oksirana (OOC) sebanyak 4.91 % diperolehi dengan menggunakan 15 µL H 2 O 2 , 120 mg Novozym 435 ® dan 7 jam tindak balas. Analisis 1 H NMR mengesahkan kumpulan terepoksida pada 2.92 -3.12 ppm manakala isyarat 13 C NMR menunjukkan bacaan pada 54.59 -57.29 ppm. Analisis LC-MS menunjukkan bahawa MEOA memberikan m/z 296.22 sebagai produk akhir. MEOA menunjukkan takat tuang yang baik pada suhu -41 ºC. Takat kilat MEOA meningkat pada suhu 128 ºC berbanding pada suhu 115ºC oleh asid linoleik (LA). Dalam keadaan yang sama, kebiasaanya VI untuk LA pada 224 beberapa ratus sentistok (cSt) lebih likat daripada MEOA 130.8. MEOA mempunyai kestabilan oksidatif pada suhu 168 ºC. MEOA berpotensi untuk dijadikan sebagai produk pertengahan dalam aplikasi tenaga keterbaharuan.

show abstract

“…27 35 A presença de epóxidos cis ficou evidenciada pelo sinal dos hidrogênios oxirânicos observados em 2,9 ppm, sendo este característico de um autêntico grupo epóxido cis, pois os hidrogênios de um epóxido trans ressonariam em 2,63 ppm. 36 Isto indica que a configuração cis, presente na maioria dos ácidos graxos insaturados de matérias-primas renováveis, é mantida no correspondente epóxido. A reação 6 da Tabela 2 foi realizada com o catalisador no líquido iônico após ter sido utilizado na reação 5.…”

Section: Reação De Epoxidaçãounclassified

Epoxidação do óleo de soja com o sistema catalítico [MoO2(acac)2]/TBHP EM [bmim][PF6]

Farias¹,

Martinelli²

2012

Quím. Nova

View full text Add to dashboard Cite

Catalytic epoxidation of methyl linoleate

Cited by 65 publications

References 18 publications

Epoxidation of methyl esters derived from Jatropha oil: An optimization study

Epoxidation of methyl esters derived from Jatropha oil: An optimization study

Epoxidation Synthesis of Linoleic Acid for Renewable Energy Applications

Epoxidação do óleo de soja com o sistema catalítico [MoO2(acac)2]/TBHP EM [bmim][PF6]

Contact Info

Product

Resources

About