Reactivity of the biphasic trichloroacetonitrile-CH&lt;sub&gt;2&lt;/sub&gt;Cl&lt;sub&gt;2&lt;/sub&gt;/H&lt;sub&gt;2&lt;/sub&gt;O&lt;sub&gt;2&lt;/sub&gt; system in the epoxidation of soybean oil

Gerbase, Annelise Engel; Brasil, Márcia Campos; Gregório, José Ribeiro; Mendes, Ana Néry Furlan; Holleben, Maria Luiza Ambros von; Martinelli, Márcia

doi:10.3989/gya.2002.v53.i2.301

Cited by 6 publications

(4 citation statements)

References 19 publications

(14 reference statements)

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“…Our group has studied different methods of functionalizing vegetable oils to obtain new raw materials for the preparation of biorenewable materials (11,12). In this study, we prepared formiated epoxy soy polyols in a one-step synthesis and investigated their influence on the mechanical properties of PU networks.…”

Section: Introductionmentioning

confidence: 99%

Polyurethane networks from formiated soy polyols: Synthesis and mechanical characterization

Monteavaro

Silva

Costa

et al. 2005

J Americ Oil Chem Soc

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Polyurethanes can be prepared using polyols obtained from vegetable oils in natura, such as castor oil, or from functionalized vegetable oils, such as hydroxylated soybean oil. These polyurethanes have different valuable properties, determined by their chemical composition and cross-linking density. In this study, soy epoxy polyols with different OH contents were prepared through a one-step reaction using the method of in situ performic acid generation. Polyols with OH functionalities from 1.9 to 3.2 were reacted in bulk with different diisocyanates at a NCO/OH molar ratio of 0.8 and 60°C for 24 h. Mechanical properties of the polyurethanes were determined by dynamic mechanical thermal analysis, hardness (Shore A), and swelling measurements. Polymer networks with glass-transition temperatures (T g ) from -13 to 48°C were obtained. We observed that the higher the OH functionality of the polyols, the higher the T g and cross-linking density of the polyurethane network. The influence of diisocyanate structure (rigid or flexible chain), curing temperature, and curing reaction time on mechanical properties was also investigated.Paper no. J10956 in JAOCS 82, 365-371 (May 2005). KEY WORDS:Hydroxylated soybean oil, mechanical properties, polyurethane, soy epoxy polyol.The use of renewable resources has attracted the attention of many researchers because of their potential to replace petrochemical derivatives (1-3). Soybean oil is an inexpensive, readily available, renewable resource and provides an excellent platform for polymeric materials. Soybean oil is mainly composed of TG molecules derived from unsaturated FA such as oleic acid (22%), linoleic acid (55%), and linolenic acid (7%). Although they possess double bonds, which are the reactive sites for coatings and paints, they need to be functionalized to prepare polymers (4). Polyurethanes (PU) have been prepared from vegetable oils in natura, such as castor oil, or from polyols obtained from vegetable oils, such as corn, sunflower, and soybean oils, and show a number of excellent properties because of the hydrophobic nature of TG (5,6). To use natural oils as raw materials for PU production, multiple hydroxyl functionalities are required. Usually these are obtained by reacting epoxidized oils with low-M.W. mono-or polyfunctional alcohols or acids.Recently, Petrovic et al. (7) reported the effect of the NCO/OH molar ratio on soy-based PU network properties using a methoxylated soy polyol (OH functionality = 3.7) and 4,4′-methylenebis(phenyl isocyanate) (MDI). Glassy polymers were produced when the NCO/OH ratio was between 0.8 and 1.05. Higher cross-linking densities, glass-transition temperatures (T g ), and tensile strengths were observed as the NCO/OH ratio increased. The influence of the diisocyanate structure on the properties of these soy-based PU was also investigated (8).Guo et al. (9) reported the physical and mechanical properties of soy polyol-derived PU prepared by the hydrogenation of hydroformylated soybean oil. When the hydroformylation reaction was rhod...

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Section: Introductionmentioning

confidence: 99%

Polyurethane networks from formiated soy polyols: Synthesis and mechanical characterization

Monteavaro

Silva

Costa

et al. 2005

J Americ Oil Chem Soc

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“…Continuing our effort in developing new environmental friendly epoxidation catalysts [11][12][13], the Fe-acac/silica was tested as heterogeneous catalyst for the cis-cyclooctene epoxidation, in the same conditions of homogeneous Mukaiyama system [14].…”

Section: Introductionmentioning

confidence: 99%

Iron acetylacetonate complex anchored on silica xerogel polymer

Brasil

Benvenutti

Gregório

et al. 2005

Reactive and Functional Polymers

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“…All chemical shifts quoted are relative to tetramethylsilane using the positive downfield convention. The NMR methodology for iodine determination has been described previously (20)(21)(22).…”

Section: Methodsmentioning

confidence: 99%

Castor oil hydrogenation by a catalytic hydrogen transfer system using limonene as hydrogen donor

Martinelli

Schneider

Baldissarelli

et al. 2005

J Americ Oil Chem Soc

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The hydrogenation of castor oil was investigated using a catalytic transfer hydrogenation system in which palladium on carbon was the catalyst and limonene was the solvent and hydrogen donor. The highest percentage of castor oil modification occurred at 178°C using 1% Pd/C and an oil/limonene ratio of 1:3. The optimized system presented very good reproducibility and 100% conversion of the ricinoleate. GC using a mass spectrometer as detector and 1 H NMR spectra of the products indicated that hydrogenation was accompanied by dehydrogenation leading to a mixture of 12-hydroxy and 12-keto stearic derivatives.Paper no. J10895 in JAOCS 82, 279-283 (April 2005).KEY WORDS: CTH, hydrogenation of castor oil, hydrogen donor, hydroxy stearic ester, keto stearic ester, palladium catalyst.

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Reactivity of the biphasic trichloroacetonitrile-CH<sub>2</sub>Cl<sub>2</sub>/H<sub>2</sub>O<sub>2</sub> system in the epoxidation of soybean oil

Cited by 6 publications

References 19 publications

Polyurethane networks from formiated soy polyols: Synthesis and mechanical characterization

Polyurethane networks from formiated soy polyols: Synthesis and mechanical characterization

Iron acetylacetonate complex anchored on silica xerogel polymer

Castor oil hydrogenation by a catalytic hydrogen transfer system using limonene as hydrogen donor

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