Thermophysical study of methyl levulinate

Lomba, Laura; Lafuente, Carlos; García-Mardones, Mónica; Gascón, Ignacio; Giner, Beatriz

doi:10.1016/j.jct.2013.05.025

Cited by 38 publications

(34 citation statements)

References 29 publications

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“…In a previous paper (Lomba et al 2013;Lomba et al 2011) values of the logarithm of 1-octanol/water partition coefficient, log P, were computed in silico using the ALOGP method (Ghose and Crippen 1986;Ghose et al 1988;Viswanadhan et al 1989) with values of -0.14 for LA, -0.17 for ML, 0.38 for EL and 1.36 for BL. We have compared the computed log P values to those predicted with the KowWin method (available on http://esc.syrres.com/esc/est_kowdemo.htm) (Meylan and Howard 1995).…”

Section: Physico-chemical Properties Of Levulinates Related To Toxicitymentioning

confidence: 99%

“…Although 4 some data exist regarding their molecular behavior (Guerrero et al 2011;Lomba et al 2013;Lomba et al 2011), information regarding their toxicity and ecotoxicity is scarce.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, we have evaluated the shortterm toxicity of levulinates to the photosynthesis of Chlamydomonas reinhardtii using fluorimetry. The results were analyzed and related to the physicochemical properties previously reported for these compounds (Guerrero et al 2011;Lomba et al 2013). We have also provided the first approaches for risk assessment of these compounds in aquatic and terrestrial environments.…”

Section: Introductionmentioning

confidence: 99%

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Ecotoxicity studies of the levulinate ester series

et al. 2014

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Abstract:The increasing interest in the development of novel green solvents has led to the synthesis of benign alternative products with minimized environmental impacts.However, most of published studies on green solvents focus primarily on their physicochemical properties, with limited emphasis on absence of ecotoxicological assessment. In this study, we evaluated the acute ecotoxicity of four levulinates (levulinic acid, methyl levulinate, ethyl levulinate and butyl levulinate) on freshwater algae (Chlamydomonas reinhardtii), bacteria (Vibrio fischeri), daphnids (Daphnia magna) and earthworms (Eisenia foetida) using various dose-response tests. As a general trend, the toxicity of levulinate esters in aquatic exposure (assessed as the EC 50 ) increased as a function of increasing alkyl chain length; accordingly, the most toxic compound for the aquatic organisms was butyl levulinate, followed by ethyl levulinate and methyl levulinate. The most toxic compound for Eisenia foetida (terrestrial exposure) was methyl levulinate, followed by ethyl levulinate, butyl levulinate and levulinic acid; in this case, we observed an inverse relationship between toxicity and alkyl chain length. Based on both the lowest EC 50 found in the aquatic media and the ratio between predicted environmental concentration (PEC) and the predicted no-effect concentration (PNEC), we have estimated the maximum allowable values in the 2 environment for these chemicals to be 1.093 mg L -1 for levulinic acid, 2.761 mg L -1 for methyl levulinate, 0.982 mg L -1 for ethyl levulinate and 0.151 mg L -1 for butyl levulinate.

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Section: Physico-chemical Properties Of Levulinates Related To Toxicitymentioning

confidence: 99%

“…Although 4 some data exist regarding their molecular behavior (Guerrero et al 2011;Lomba et al 2013;Lomba et al 2011), information regarding their toxicity and ecotoxicity is scarce.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Ecotoxicity studies of the levulinate ester series

et al. 2014

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“…Values for these properties were gathered from bibliographic data [11,[13][14][15] for the 3 studied families of chemicals. Thus, there will be a correlation between this type of information and the ecotoxicological effect, which, as is well known, is a reflection of the molecular structure and interactions with the surrounding molecules.…”

Section: Physicochemical Propertiesmentioning

confidence: 99%

Exploring the usefulness of key green physicochemical properties: Quantitative structure–activity relationship for solvents from biomass

Zuriaga

Giner

Ribate

et al. 2018

Enviro Toxic and Chemistry

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In recent decades there has been a growing interest in the development of new solvents from biomass. Some of these new solvents have been classified as green because of their renewable and sustainable source. However, characterization from the ecotoxicological and physicochemical points of view is needed to categorize them as green solvents. We have selected several key physicochemical properties that can reflect environmental features (density, boiling point, critical aggregation concentration, and log p) and explored their usefulness for preliminarily assessing the green character of the studied solvents. Specifically, we have studied several solvents from biomass: lactate family (methyl, ethyl, and butyl lactate), furfural family (furfural, 5-methylfurfural, furfuryl alcohol, and tetrahydrofurfuryl alcohol), and levulinate family (methyl, ethyl, and butyl levulinate). To fill the gaps and complete some toxicity data for the environment, we have measured the ecotoxicity using 2 of the most common and versatile biomodels, bacteria Vibrio fischeri and crustacean Daphnia magna, for furfural- and lactate-derived compounds. The results indicate that solvents from biomass can be categorized as green because their toxicity for the environment is low. Finally, a quantitative structure-activity relationship (QSAR) study was performed with the selected key properties and the ecotoxicological information. Despite the different structure of the chemicals under study, good correlations were found for the studied organisms. It seems that log p and critical aggregation concentration reflect the greatest part of the ecotoxic behavior, whereas density and boiling point cannot reflect toxicity signals. However, these properties are rather useful for assessing the final environmental fate of the studied chemicals. Environ Toxicol Chem 2018;37:1014-1023. © 2017 SETAC.

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“…Given the density for the humins/ML blend and a density of 1050 kg/m 3 for ML [66], a density of 1339 kg/m 3 can be calculated for neat humins; assuming the volume of the blend equals the volume of its components. Combining the lower heating value (LHV) and density, one finds a volumetric energy density of 28 MJ/l, vs. 41MJ/l for HFO.…”

Section: Heating Valuementioning

confidence: 99%

Spray Combustion Analysis of Humins

Feijen¹,

Klink

Jong

et al. 2017

SAE Technical Paper Series

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Second generation biomass is an attractive renewable feedstock for transport fuels. Its sulfur content is generally negligible and the carbon cycle is reduced from millions to tens of years. One hitherto non-valorized feedstock are so-called humins, a residual product formed in the conversion of sugars to platform chemicals, such as hydroxymethylfurfural and methoxymethylfurfural, intermediates in the production of FDCA, a building block used to produce the polyethylene furanoate (PEF) bottle by Avantium.The focus of this study is to investigate the spray combustion behavior of humins as a renewable alternative for heavy fuel oil (HFO) under large two-stroke engine-like conditions in an optically accessible constant volume chamber. To reduce the viscosity to HFO levels of the otherwise crystalline humins, methyl levulinate (ML), another side-stream from the same sugar dehydration process, is blended to the former compound at 25 wt.-%; a ratio comparable to that actually produced in many dehydration processes.Various fuel properties of interest, including elemental composition, heating value, density, ignition quality, acid number, flash point, pour point, carbon residue, sediment, water and ash content are measured for the resulting humins-ML blend.The blend is injected into an optically accessible constant volume chamber, the dimensions, injector characteristics and prevailing ambient conditions of which are representative of those found in large two-stroke marine engines. Commercial HFO is used as a benchmark.The combustion process is evaluated by means of shadow imaging and OH*-chemiluminescence. The former and latter optical techniques are used to determine the phasing and overall magnitude of the heat release event, and ignition delay/location and flame lift off length, respectively.From the results becomes clear that the average ignition delay is comparable to that of HFO, albeit at a higher cycle-to-cycle variation. Notwithstanding a longer lift off length and more downstream ignition kernels, the overall results suggest that the proposed bioblend is a feasible renewable alternative for HFO in terms of technical feasibility.

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Thermophysical study of methyl levulinate

Cited by 38 publications

References 29 publications

Ecotoxicity studies of the levulinate ester series

Ecotoxicity studies of the levulinate ester series

Exploring the usefulness of key green physicochemical properties: Quantitative structure–activity relationship for solvents from biomass

Spray Combustion Analysis of Humins

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