- Electrochemical cross-coupling of biogenic di-acids for sustainable fuel production
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Direct electrocatalytic conversion of bio-derivable acids represents a promising technique for the production of value-added chemicals and tailor-made fuels from lignocellulosic biomass. In the present contribution, we report the electrochemical decarboxylation and cross-coupling of ethyl hydrogen succinate, methyl hydrogen methylsuccinate and methylhexanoic acid with isovaleric acid. The reactions were performed in aqueous solutions or methanol at ambient temperatures, following the principles of green chemistry. High conversions of the starting materials have been obtained with maximum yields between 42 and 61% towards the desired branched alkane products. Besides costly Pt electrodes also (RuxTi1-x)O2 on Ti electrodes exhibited a notable activity for cross-Kolbe electrolysis. As some of the products are insoluble in water, easy product isolation and reuse of the reaction solvent is enabled via phase separation. Several side products have been identified to evaluate the efficiency of the reaction and to elucidate the factors influencing the product selectivity. The yielded alkanes and esters were assessed with regard to their potential as fuels for internal combustion engines. While the longer alkanes constitute promising candidates for the compression-ignition engine, the smaller ester represents an interesting option for the spark-ignition engine.
- Holzh?user, F. Joschka,Creusen, Guido,Moos, Gilles,Dahmen, Manuel,K?nig, Andrea,Artz, Jens,Palkovits, Stefan,Palkovits, Regina
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p. 2334 - 2344
(2019/05/21)
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- Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica
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Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.
- Tai, Akira,Syouno, Emi,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Higashiura, Yasutomo,Kakizaki, Masashi,Hara, Hideho,Naito, Tikahiko
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p. 111 - 121
(2007/10/03)
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- Coupling Reaction of Grignard Reagents with α,ω-Dibromoalkanes in the Presence of Copper(I) Bromide-HMPA: Preparation of α,ω-Bis(vinylaryl)alkanes
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The coupling reaction of Grignard reagents with α,ω-dibromoalkanes took place smoothly in THF/HMPA (12:1) in the presence of a catalytic amount of copper(I) bromide and gave the products in 60-100 percent yields.Several α,ω-bis(vinylaryl)alkanes were prepared in reasonable yields by the application of this reaction.
- Nishimura, Jun,Yamada, Noriyuki,Horiuchi, Yuzuru,Ueda, Eiji,Ohbayashi, Akihiro,Oku, Akira
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p. 2035 - 2037
(2007/10/02)
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