Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1

Qingyan Chu; Guangke He; Yang Xi; Ping Wang; Haoxuan Yu; Rui Liu; Hongjun Zhu

doi:10.1016/j.catcom.2018.01.022

Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1

Qingyan Chu, Guangke He, Yang Xi, Ping Wang, Haoxuan Yu, Rui Liu, Hongjun Zhu

School of Chemistry and Moleculai Engineering

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A green and efficient one-pot method has been developed for the synthesis of low-carbon chain nitroalkanes via a novel TS-1 catalyzed tandem oxidation of ketones with H₂O₂ and NH₃. The tandem reaction including ammoxidation, oximation and oxidation of oximes, afforded up to 88% yield and 98% chemo-selectivity requiring only 90 min, at 70 °C and atmospheric pressure. Moreover, this method was even amenable to 100-fold scale-up without loss of chemical efficiency with 87% yield, represents a significant advance towards industrial production of nitroalkanes. Furthermore, the plausible mechanism of TS-1 catalyzed tandem oxidation of ketones to prepare nitroalkanes was proposed.

Original language	English
Pages (from-to)	46-50
Number of pages	5
Journal	Catalysis Communications
Volume	108
DOIs	https://doi.org/10.1016/j.catcom.2018.01.022
State	Published - Apr 2018

Keywords

Catalyzed oxidation
Green synthesis
Nitroalkanes
TS-1
Tandem reaction

Access to Document

10.1016/j.catcom.2018.01.022

Cite this

@article{56a7844e4be84a6ea5ab80248e1e8000,

title = "Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1",

abstract = "A green and efficient one-pot method has been developed for the synthesis of low-carbon chain nitroalkanes via a novel TS-1 catalyzed tandem oxidation of ketones with H2O2 and NH3. The tandem reaction including ammoxidation, oximation and oxidation of oximes, afforded up to 88% yield and 98% chemo-selectivity requiring only 90 min, at 70 °C and atmospheric pressure. Moreover, this method was even amenable to 100-fold scale-up without loss of chemical efficiency with 87% yield, represents a significant advance towards industrial production of nitroalkanes. Furthermore, the plausible mechanism of TS-1 catalyzed tandem oxidation of ketones to prepare nitroalkanes was proposed.",

keywords = "Catalyzed oxidation, Green synthesis, Nitroalkanes, TS-1, Tandem reaction",

author = "Qingyan Chu and Guangke He and Yang Xi and Ping Wang and Haoxuan Yu and Rui Liu and Hongjun Zhu",

note = "Publisher Copyright: {\textcopyright} 2018",

year = "2018",

month = apr,

doi = "10.1016/j.catcom.2018.01.022",

language = "英语",

volume = "108",

pages = "46--50",

journal = "Catalysis Communications",

issn = "1566-7367",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1

AU - Chu, Qingyan

AU - He, Guangke

AU - Xi, Yang

AU - Wang, Ping

AU - Yu, Haoxuan

AU - Liu, Rui

AU - Zhu, Hongjun

PY - 2018/4

Y1 - 2018/4

N2 - A green and efficient one-pot method has been developed for the synthesis of low-carbon chain nitroalkanes via a novel TS-1 catalyzed tandem oxidation of ketones with H2O2 and NH3. The tandem reaction including ammoxidation, oximation and oxidation of oximes, afforded up to 88% yield and 98% chemo-selectivity requiring only 90 min, at 70 °C and atmospheric pressure. Moreover, this method was even amenable to 100-fold scale-up without loss of chemical efficiency with 87% yield, represents a significant advance towards industrial production of nitroalkanes. Furthermore, the plausible mechanism of TS-1 catalyzed tandem oxidation of ketones to prepare nitroalkanes was proposed.

AB - A green and efficient one-pot method has been developed for the synthesis of low-carbon chain nitroalkanes via a novel TS-1 catalyzed tandem oxidation of ketones with H2O2 and NH3. The tandem reaction including ammoxidation, oximation and oxidation of oximes, afforded up to 88% yield and 98% chemo-selectivity requiring only 90 min, at 70 °C and atmospheric pressure. Moreover, this method was even amenable to 100-fold scale-up without loss of chemical efficiency with 87% yield, represents a significant advance towards industrial production of nitroalkanes. Furthermore, the plausible mechanism of TS-1 catalyzed tandem oxidation of ketones to prepare nitroalkanes was proposed.

KW - Catalyzed oxidation

KW - Green synthesis

KW - Nitroalkanes

KW - TS-1

KW - Tandem reaction

UR - http://www.scopus.com/inward/record.url?scp=85041480220&partnerID=8YFLogxK

U2 - 10.1016/j.catcom.2018.01.022

DO - 10.1016/j.catcom.2018.01.022

M3 - 文章

AN - SCOPUS:85041480220

SN - 1566-7367

VL - 108

SP - 46

EP - 50

JO - Catalysis Communications

JF - Catalysis Communications

ER -

Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this