Synthesis of renewable high-density fuel with isophorone

Abstract 1,1,3-Trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane, a renewable high density fuel, was first produced in a high overall carbon yield (~70%) with isophorone which can be derived from hemicellulose. The synthetic route used this work contains three steps. In the first step, 3,3,5-trimet...

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Autores principales:	Wei Wang, Yanting Liu, Ning Li, Guangyi Li, Wentao Wang, Aiqin Wang, Xiaodong Wang, Tao Zhang
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/ad35789c3a334ca8abcbea39b378093c
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spelling	oai:doaj.org-article:ad35789c3a334ca8abcbea39b378093c2021-12-02T15:06:21ZSynthesis of renewable high-density fuel with isophorone10.1038/s41598-017-06556-72045-2322https://doaj.org/article/ad35789c3a334ca8abcbea39b378093c2017-07-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-06556-7https://doaj.org/toc/2045-2322Abstract 1,1,3-Trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane, a renewable high density fuel, was first produced in a high overall carbon yield (~70%) with isophorone which can be derived from hemicellulose. The synthetic route used this work contains three steps. In the first step, 3,3,5-trimethylcyclohexanone was synthesized by the selective hydrogenation of isophorone. Among the investigated catalysts, the Pd/C exhibited the highest activity and selectivity. Over this catalyst, a high carbon yield (99.0%) of 3,3,5-trimethylcyclohexanone was achieved under mild conditions (298 K, 2 MPa H2, 1 h). In the second step, 3,5,5-trimethyl-2-(3,3,5-trimethylcyclohexylidene)cyclohexanone was produced in a high carbon yield (76.4%) by the NaOH catalyzed self-aldol condensation of 3,3,5-trimethylcyclohexanone which was carried out in a round bottom flask attached to the Dean–Stark apparatus. In the third step, the 3,5,5-trimethyl-2-(3,3,5-trimethylcyclohexylidene)cyclohexanone was hydrodeoxygenated under solvent-free conditions. High carbon yield (93.4%) of 1,1,3-trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane was obtained over the Ni/SiO2 catalyst. The 1,1,3-trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane as obtained has a density of 0.858 g mL−1 and a freezing point of 222.2 K. As a potential application, it can be blended into conventional fuels (such as RP-1, RG-1, etc.) for rocket propulsion.Wei WangYanting LiuNing LiGuangyi LiWentao WangAiqin WangXiaodong WangTao ZhangNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-6 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Wei Wang Yanting Liu Ning Li Guangyi Li Wentao Wang Aiqin Wang Xiaodong Wang Tao Zhang Synthesis of renewable high-density fuel with isophorone
description	Abstract 1,1,3-Trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane, a renewable high density fuel, was first produced in a high overall carbon yield (~70%) with isophorone which can be derived from hemicellulose. The synthetic route used this work contains three steps. In the first step, 3,3,5-trimethylcyclohexanone was synthesized by the selective hydrogenation of isophorone. Among the investigated catalysts, the Pd/C exhibited the highest activity and selectivity. Over this catalyst, a high carbon yield (99.0%) of 3,3,5-trimethylcyclohexanone was achieved under mild conditions (298 K, 2 MPa H2, 1 h). In the second step, 3,5,5-trimethyl-2-(3,3,5-trimethylcyclohexylidene)cyclohexanone was produced in a high carbon yield (76.4%) by the NaOH catalyzed self-aldol condensation of 3,3,5-trimethylcyclohexanone which was carried out in a round bottom flask attached to the Dean–Stark apparatus. In the third step, the 3,5,5-trimethyl-2-(3,3,5-trimethylcyclohexylidene)cyclohexanone was hydrodeoxygenated under solvent-free conditions. High carbon yield (93.4%) of 1,1,3-trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane was obtained over the Ni/SiO2 catalyst. The 1,1,3-trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane as obtained has a density of 0.858 g mL−1 and a freezing point of 222.2 K. As a potential application, it can be blended into conventional fuels (such as RP-1, RG-1, etc.) for rocket propulsion.
format	article
author	Wei Wang Yanting Liu Ning Li Guangyi Li Wentao Wang Aiqin Wang Xiaodong Wang Tao Zhang
author_facet	Wei Wang Yanting Liu Ning Li Guangyi Li Wentao Wang Aiqin Wang Xiaodong Wang Tao Zhang
author_sort	Wei Wang
title	Synthesis of renewable high-density fuel with isophorone
title_short	Synthesis of renewable high-density fuel with isophorone
title_full	Synthesis of renewable high-density fuel with isophorone
title_fullStr	Synthesis of renewable high-density fuel with isophorone
title_full_unstemmed	Synthesis of renewable high-density fuel with isophorone
title_sort	synthesis of renewable high-density fuel with isophorone
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/ad35789c3a334ca8abcbea39b378093c
work_keys_str_mv	AT weiwang synthesisofrenewablehighdensityfuelwithisophorone AT yantingliu synthesisofrenewablehighdensityfuelwithisophorone AT ningli synthesisofrenewablehighdensityfuelwithisophorone AT guangyili synthesisofrenewablehighdensityfuelwithisophorone AT wentaowang synthesisofrenewablehighdensityfuelwithisophorone AT aiqinwang synthesisofrenewablehighdensityfuelwithisophorone AT xiaodongwang synthesisofrenewablehighdensityfuelwithisophorone AT taozhang synthesisofrenewablehighdensityfuelwithisophorone
_version_	1718388472870338560

Synthesis of renewable high-density fuel with isophorone

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