Application of metal triflate catalysts for the <i>trans</i>‐esterification of <i>Jatropha curcas</i> L. oil with methanol and higher alcohols

Daniel, Louis; Rasrendra, Carolus Borromeus; Kloekhorst, Arjan; Broekhuis, Antonius; Manurung, Robert; Heeres, Hero J.

doi:10.1007/s11746-013-2364-3

Cited by 10 publications

(8 citation statements)

References 28 publications

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“…16 For instance, the viscosity of EJO (0.23 Pa s) is about one order of magnitude higher than the viscosity of JO as previously reported in our group (0.034 Pa s). 37 As such, a low viscosity should correspond with a low amount of epoxide groups and this is indeed the case.…”

Section: Synthesis and Properties Of Epoxidized Oils (Eo)mentioning

confidence: 95%

Synthesis and properties of cross‐linked polymers from epoxidized rubber seed oil and triethylenetetramine

Abduh

Iqbal

Picchioni

et al. 2015

J of Applied Polymer Sci

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A series of epoxidized oils were prepared from rubber seed, soybean, jatropha, palm, and coconut oils. The epoxy content varied from 0.03 to 7.4 wt %, in accordance with the degree of unsaturation of the oils (lowest for coconut, highest for rubber seed oil). Bulk polymerization/curing of the epoxidized oils with triethylenetetramine (in the absence of a catalyst) was carried out in a batch setup (1 : 1 molar ratio of epoxide to primary amine groups, 100°C, 100 rpm, 30 min) followed by casting of the mixture in a steel mold (180°C, 200 bar, 21 h) and this resulted in cross‐linked resins. The effect of relevant pressing conditions such as time, temperature, pressure, and molar ratio of the epoxide and primary amine groups was investigated and modeled using multivariable nonlinear regression. Good agreement between experimental data and model were obtained. The rubber seed oil‐derived polymer has a Tg of 11.1°C, a tensile strength of 1.72 MPa, and strain at break of 182%. These values are slightly higher than for commercial epoxidized soybean oil (Tg of 6.9°C, tensile strength of 1.11 MPa, and strain at break of 145.7%). However, the comparison highlights the potential for these novel resins to be used at industrial/commercial level. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 42591.

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Section: Synthesis and Properties Of Epoxidized Oils (Eo)mentioning

confidence: 95%

Synthesis and properties of cross‐linked polymers from epoxidized rubber seed oil and triethylenetetramine

Abduh

Iqbal

Picchioni

et al. 2015

J of Applied Polymer Sci

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“…Another advantage of our catalytic procedure is the mild conditions employed. Under harsher reaction conditions it has been shown that when using an unsaturated FFA, such as OA, isomerisation, and cyclization can occur producing the lactone , and/or butyoxylation of the double bond by the excess butanol . 1 H and 13 C NMR analysis of our esters revealed that no cyclization or butyoxylation of the double bond in OA occurred under the employed reaction conditions (see ESI Figs.…”

Section: Resultsmentioning

confidence: 83%

Effect of water and lipophilic alcohols or amines on the 4‐dodecylbenzenesulfonic acid‐catalyzed esterifications, trans‐esterifications, and amidations

Wallis

Cerny

Lacroux

et al. 2017

Euro J Lipid Sci & Tech

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4‐Dodecylbenzenesulfonic acid (DBSA) was employed in the esterification of oleic acid (OA) and the trans‐esterification of oleic oil (OO) with 1‐butanol as alcohol in the presence of various degrees of excess water. Under these conditions DBSA was found to be a highly active esterification catalyst regardless of excess water content, but was found to be a less effective for trans‐esterification reactions. Lipophilic alcohols of differing straight and branched C3‐6 chains were also tested on mixtures of OA/water (1:1) in DBSA‐catalyzed esterifications; OO/water (1:1) in trans‐esterifications; and OA/OO/water (1:1:1) in simultaneous esterifications and trans‐esterifications. While longer straight chain alcohols generally gave a two‐fold increase in yield of their corresponding alkyl oleates to 80%+, we observed a doubling from 30–50% to 60–95% of alkyl oleate yield for the OO/OA/water mixture. DBSA‐catalyzed amidations of OO and methyl oleate emulsions in water were conducted with 1‐butyl and 1‐heptyl amine where it was found that the more lipophilic the ester moiety the higher the yield of alkyl amide. Practical applications: The practical advantages of DBSA as catalyst are high conversions to the desired product along with its tolerance to high quantities of water, emulsified within the lipid material. A capacity to transform a range of substrates with varying lipophilic character in a range of condensation reactions. In addition, we demonstrate that esterification and trans‐esterification reactions could be performed simultaneous and in the presence of high quantities of water. This is of direct interest to the transformation of waste sources of lipids that often contain a mixture of triglycerides and free fatty acids in various concentrations, emulsified with waste water. Furthermore, we demonstrate that all of the value‐added products/co‐products can be separated by an effective and industrially relevant methodology, including recovery of the DBSA catalyst as well as the water and water soluble co‐products, such as glycerol. A 4‐Dodecylbenzenesulfonic acid (DBSA) is demonstrated to be an effective polyvalent catalyst for the recovery of aqueous emulsified lipids by conversion into value‐added products. DBSA proved to be a polyvalent catalyst showing high activity using a range of substrates, performing esterification, trans‐esterification, and amidations reactions efficiently despite the potential detrimental presence of high water loadings. The commercial incentive of our system is the phase separation of the product mixture into the converted lipids for use as biofuels and glycerol for resale as a fine chemical.

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“…The quality of these oils is shown in Table . Jatropha biodiesel was made from JO4 according to the transesterification method described in L. Daniel et al . The antioxidants with a purity of 95–99.9% were bought from Sigma–Aldrich (Amsterdam, The Netherlands) with exception of Ethanox 4702 (4,4′‐methylenebis‐(2,6‐di‐ tert ‐butylphenol) which was kindly donated by Albemarle (Amsterdam, The Netherlands).…”

Section: Methodsmentioning

confidence: 99%

Screening of antioxidants as stabilisers for Jatropha curcas L. oil

Subroto¹,

Manurung

Heeres³

et al. 2013

Euro J Lipid Sci & Tech

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The effect of antioxidants on the oxidation stability of oils extracted from Jatropha curcas seeds was measured by the accelerated oxidation test specified in EN 14112 using commercial Rancimat 873 equipment. To find the appropriate antioxidant for jatropha oil, fourteen different antioxidants were screened at concentrations of 500 and 1000 ppm. Pyrogallol (PY) and propyl gallate (PG) significantly improved the oxidative stability of jatropha oil and PY was further studied at concentrations of 50-1000 ppm. Even at concentrations as low as 50 ppm, PY was found to fulfill the specifications set by the DIN 51605 norm for plant oil as biofuels. Mixtures of antioxidants were tested at concentrations varying between 100 and 1000 ppm, showing a synergistic effect for the combination of PY and N,N 0 -di-sec-butyl-p-phenylenediamine at all concentrations and ratios tested. It further was found that the quality, i.e. the history of the oil in terms of processing, age and storage conditions, strongly affects the performance of PY as the antioxidant. PY in particular improved the oxidative stability of oxidized and highly acidic oils. PY was found to be a good antioxidant for both jatropha oil and the derived biodiesel.Practical applications: Jatropha oil is one of many potential triglyceride feedstocks suitable for the production of biofuel or other consumer products. Finding the best antioxidant for this particular resource is important since the resistance to oxidative degradation depends on the chemical structure of the triglyceride. Pyrogallol was found to be the preferred antioxidant with beneficial results found for oxidized and, as a result, highly acidic oils. The results of this study are useful for companies involved in jatropha oil-derived products such as biodiesel, lubricants or other non-food applications.

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Application of metal triflate catalysts for the trans‐esterification of Jatropha curcas L. oil with methanol and higher alcohols

Cited by 10 publications

References 28 publications

Synthesis and properties of cross‐linked polymers from epoxidized rubber seed oil and triethylenetetramine

Synthesis and properties of cross‐linked polymers from epoxidized rubber seed oil and triethylenetetramine

Effect of water and lipophilic alcohols or amines on the 4‐dodecylbenzenesulfonic acid‐catalyzed esterifications, trans‐esterifications, and amidations

Screening of antioxidants as stabilisers for Jatropha curcas L. oil

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