Catalytic conversions in green aqueous media. Part 8: Partial and full hydrogenation of renewable methyl esters of vegetable oils

Bouriazos, Achilleas; Vasiliou, Christiana; Tsichla, Angeliki; Papadogianakis, Georgios

doi:10.1016/j.cattod.2014.08.021

Cited by 21 publications

(25 citation statements)

References 141 publications

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“…Several pathways for synthesizing polyols from soybean oil have been studied, for instance, thiol–ene reactions, hydrogenation, ozonolysis, hydroformylation, transesterification, and the ring opening of epoxidized oils . The last consists of a two‐step procedure in which, first, the double bond of the triglycerides are epoxidized and, second, oxirane rings formed are opened by a so‐called ring‐opening agent (ROA).…”

Section: Introductionmentioning

confidence: 99%

Highly functional lactic acid ring‐opened soybean polyols applied to rigid polyurethane foams

Herrán

Amalvy

Chiacchiarelli

2019

J of Applied Polymer Sci

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We synthesized polyols with high hydroxyl functionalities (F OH s), between 9.0 and 12.6, and characterized them with differential scanning calorimetry, thermogravimetric analysis, and size exclusion chromatography after we parametrically studied the ringopening reaction of epoxidized soybean oil with lactic acid (LA) as a function of the reaction temperature and lactic acid equivalent fraction (f LA ). An increase of only 20 C in the reaction temperature (from 80 to 100 C) caused changes in the hydroxyl number (+17.8%), F OH (-25%), viscosity (-14.0%), and oligomeric content (-24.1%). f LA mostly affected the ring-opening yield, and only for f LA values above 0.4 was possible to achieve values higher than 80%. Rigid polyurethane foams (rPUFs) were synthesized and characterized with scanning electron microscopy, dynamic mechanical analysis (DMA), and compressive mechanical tests. rPUFs with a very high specific compressive strength (7.8 kPa kg -1 m 3 ) were synthesized solely with biobased soybean oil. DMA revealed a compromised relationship between the specific compressive strength and its temperature dependence. To increase the first one, the most relevant method was to increase F OH . Instead, to increase the latter one, the OH number had to be maximized.

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Section: Introductionmentioning

confidence: 99%

Highly functional lactic acid ring‐opened soybean polyols applied to rigid polyurethane foams

Herrán

Amalvy

Chiacchiarelli

2019

J of Applied Polymer Sci

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“…On the other hand, the methylation of oleic acid (entry 2) occurred together with the C=C bond hydrogenation, yielding a 95% of methyl stearate. This result is significant, because there is an increasing interest in the fully hydrogenation process of FAMEs [40,41].…”

Section: Esterificationmentioning

confidence: 84%

Esterification, transesterification and hydrogenation reactions of polyunsaturated compounds catalyzed by a recyclable polymer supported palladium catalyst

Dell’Anna

Capodiferro

Mali

et al. 2016

Journal of Organometallic Chemistry

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“…136 The same type of result was obtained using a water soluble Rh/TPPTS complex (TPPTS = sodium salt of trisulfonated PPh 3 ) in a biphasic hydrogenation process under moderate conditions (120°C , 50 bar H 2 , 60 min) from mixtures of methyl fatty esters from three different vegetable oils. 137 Another classical reaction for fatty acid derivatives is hydroformylation. 138 This technology is considered to be mature enough to produce hydroformylated fatty esters and triglycerides, and in the last few years the objectives have been focused on the recycling of the catalyst 139 and improvement of the selectivities.…”

Section: Hydrogenation and Hydroformylationmentioning

confidence: 99%

Synthetic Transformations for the Valorization of Fatty Acid Derivatives

et al. 2017

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Oleochemistry is a growing field from the industrial point of view, and one of the basis for a more sustainable chemical production, less dependent of fossil sources. From this point of view, the development of selective and efficient synthetic transformations of triglycerides and fatty acids and esters is an active research field. This short review describes an overview of the most recent advances in the synthetic transformations of fatty acid derivatives into valuable chemicals. 1 Introduction 2 Triglycerides 2.1 Reactions on the ester group and multistep processes 2.2 Epoxidation 2.3 Ozonolysis 2.4 Cross metathesis 3 Reactions on the ester group of fatty acids and esters 3.1 Synthesis of free carboxylic acids 3.2 Synthesis of carboxylic esters 3.3 Reduction to alcohols and aldehydes 3.4 Synthesis of nitrogenated derivatives 4 Oxidation of Unsaturated Fatty acids and esters 4.1 Epoxidation and reactions of epoxides 4.2 Allylic oxidation 4.3 Synthesis of ketoderivatives 4.4 Oxidative cleavage 5 Addition reactions of unsaturated fatty acids and esters 5.1 Hydrogenation and hydroformilation 5.2 Cycloadditions and related reactions 5.3 Addition of carboxylic acids 5.4 Hydroalkylation 5.5 Radical additions 6 Other reactions of unsaturated fatty acids and esters 6.1 Cross metathesis 6.2 Isomerization 7 Conclusion and outlook

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Catalytic conversions in green aqueous media. Part 8: Partial and full hydrogenation of renewable methyl esters of vegetable oils

Cited by 21 publications

References 141 publications

Highly functional lactic acid ring‐opened soybean polyols applied to rigid polyurethane foams

Highly functional lactic acid ring‐opened soybean polyols applied to rigid polyurethane foams

Esterification, transesterification and hydrogenation reactions of polyunsaturated compounds catalyzed by a recyclable polymer supported palladium catalyst

Synthetic Transformations for the Valorization of Fatty Acid Derivatives

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