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Título del libro: Metathesis Transformations Of Natural Rubber: Cross-Metathesis Of Natural Rubber With Essential Oils Using Ruthenium Alkylidene Catalysts

Autores UNAM:
ARACELI MARTINEZ PONCE; SELENA GUTIERREZ FLORES; MOUKHAMED TLENKOPATCHEV;

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Autores externos:

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Idioma:
Inglés

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Año de publicación:
2016

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Palabras clave:

Butadiene; Catalyst activity; Chemical analysis; Chlorine compounds; Isoprene; Manganese; Molecular weight; Monoterpenes; Oligomers; Rubber; Ruthenium; Ruthenium compounds; Styrene; Cross metathesis; Efficient catalysts; Hoveyda-Grubbs; New applications; Orders of magnitude; Poly(styrene-co-butadiene); Ruthenium alkylidenes; Second generation; Essential oils

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Resumen:

Natural rubber (NR) and essential oils are very attractive terpene based compounds. A wide variety of bio-based structures are synthesized by transformations of terpene units. The transformations of terpene based molecules using efficient catalysts are of great interest for the development of new applications for these biomass-derived compounds. In this perspective matathesis transformations are becoming more attractive as the availability and choice of effective catalysts increase. In this research we reported the cross-metathesis of NR with essential oils and monoterpenes such as d-limonene and ß-pinene using ruthenium alkylidene catalysts the Hoveyda-Grubbs second generation [Ru(Cl2)(=CH(o-isopropoxyphenylmethylene)) (1,3-diphenyl- 4,5-dihydroimidazol-2-ylidene) (I), the Grubbs second generation (1,3- diphenyl-4,5-dihydroimidazol-2-ylidene)(PCy3)Cl2Ru = CHPh) (II) and the Grubbs first generation (PCy3)2(Cl)2Ru = CHPh (III), and ruthenium vinylidene catalysts [RuCl2(=C=CHR)(PCy3)2] (R = -p-C6H4F (IV), -p- C6H4CF3 (V) and -C6H9 (VI). The isolated oligomer products with yields ranging from 94-96% and molecular weights around Mn x 102 g/mol were obtained when the reactions were carried out at 50 °C and 80 °C in the presence of alkylidene catalysts I and II. When the ruthenium vinylidene catalysts IV-VI were used at 50 °C NR was depolymerized two orders of magnitude Mn x 104 g/mol. An enhancement of the catalytic activity was achieved at 80°C. The composition and yield of NR cross-metathesis products were determined by GC/MS (EI) analysis, and it was found that the oligomers obtained have primarily one vinyl group and one terpenemonocyclic group at the chain end with isoprene units Am = 1-3. Experiments also demonstrated that the poly(styrene-co-butadiene) depolymerized in the presence of essential oils and d-limonene to give the butadiene oligomers with molecular weight values of approximately Mn = 270-770 g/mol. According to GC/MS (EI) analysis, the main products of the poly(styrene-co-butadiene) cross-metathesis with d-limonene were limonene-terminated butadiene oligomers with m = 1-3. The cross-metathesis of NR using organic solvents and essential oils proceeded with similar efficiency and resulted in the same molecular weight isoprene oligomers. © 2016 Nova Science Publishers, Inc.

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Entidades citadas de la UNAM:

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Fuente:


ISBN:
9781634854726
Editorial:
Nova Science Publishers, Inc. Nombre de la publicación:
Metathesis transformations of natural rubber: Cross-metathesis of natural rubber with essential oils using ruthenium alkylidene catalysts
Página inicial:
165
Página final:
192

Tipo de producto:
Capítulo de un Libro