A new route to α,ω-diamines from hydrogenation of dicarboxylic acids and their derivatives in the presence of amines

Yiping Shi; Paulus Clemens Jozef Kamer; David John Cole-Hamilton

doi:10.1039/C7GC02838E

A new route to α,ω-diamines from hydrogenation of dicarboxylic acids and their derivatives in the presence of amines

Yiping Shi, Paulus Clemens Jozef Kamer, David John Cole-Hamilton

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

Abstract

A new and selective route for the synthesis of polymer precursors, primary diamines or N-substituted diamines, from dicarboxylic acids, diesters, diamides and diols using a Ru/ triphos catalyst is reported. Excellent conversions and yields are obtained under optimised reaction conditions. The reactions worked very well using 1,4-dioxane as solvent, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. This method provides a potential route to converting waste biomass to value added materials. The reaction is proposed to go through both amide and aldehyde pathways.

Original language	English
Pages (from-to)	5460-5466
Journal	Green Chemistry
Volume	19
Early online date	11 Oct 2017
DOIs	https://doi.org/10.1039/C7GC02838E
Publication status	E-pub ahead of print - 11 Oct 2017

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Shi_Green diamines_revised final
Copyright © 2017, The Royal Society of Chemistry. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1039/C7GC02838E
Accepted author manuscript, 645 KB

Clean catalysis for sustainable develop: Clean catalysis for sustainable development
Kamer, P. C. J. (PI)
EPSRC
1/11/12 → 31/10/17
Project: Standard

Conversion of renewable feedstocks into polymer precursors and pharmaceutical drugs
Shi, Y. (Author), Cole-Hamilton, D. (Supervisor), Kamer, P. C. J. (Supervisor) & Smith, A. (Supervisor), 6 Dec 2018
Student thesis: Doctoral Thesis (PhD)

Cite this

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title = "A new route to α,ω-diamines from hydrogenation of dicarboxylic acids and their derivatives in the presence of amines",

abstract = "A new and selective route for the synthesis of polymer precursors, primary diamines or N-substituted diamines, from dicarboxylic acids, diesters, diamides and diols using a Ru/ triphos catalyst is reported. Excellent conversions and yields are obtained under optimised reaction conditions. The reactions worked very well using 1,4-dioxane as solvent, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. This method provides a potential route to converting waste biomass to value added materials. The reaction is proposed to go through both amide and aldehyde pathways.",

author = "Yiping Shi and Kamer, {Paulus Clemens Jozef} and Cole-Hamilton, {David John}",

note = "We thank the EPSRC for the critical mass grant 'Clean Catalysis for Sustainable Development' (EP/J018139/1), Sasol Technology, UK for a case studentship (Y. S.) and the EPSRC UK National Mass Spectrometry Facility at Swansea University for mass spectrometric analysis",

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AU - Cole-Hamilton, David John

N1 - We thank the EPSRC for the critical mass grant 'Clean Catalysis for Sustainable Development' (EP/J018139/1), Sasol Technology, UK for a case studentship (Y. S.) and the EPSRC UK National Mass Spectrometry Facility at Swansea University for mass spectrometric analysis

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AB - A new and selective route for the synthesis of polymer precursors, primary diamines or N-substituted diamines, from dicarboxylic acids, diesters, diamides and diols using a Ru/ triphos catalyst is reported. Excellent conversions and yields are obtained under optimised reaction conditions. The reactions worked very well using 1,4-dioxane as solvent, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. This method provides a potential route to converting waste biomass to value added materials. The reaction is proposed to go through both amide and aldehyde pathways.

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A new route to α,ω-diamines from hydrogenation of dicarboxylic acids and their derivatives in the presence of amines

Abstract

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Projects

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Student theses

Conversion of renewable feedstocks into polymer precursors and pharmaceutical drugs

Cite this