Synthesis of Adipic Acid, 1,6-Hexanediamine, and 1,6-Hexanediol via Double-n-Selective Hydroformylation of 1,3-Butadiene | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

4726097

Reference Type

Journal Article

Title

Synthesis of Adipic Acid, 1,6-Hexanediamine, and 1,6-Hexanediol via Double-n-Selective Hydroformylation of 1,3-Butadiene

Author(s)

Mormul, J; Breitenfeld, Jan; Trapp, O; Paciello, R; Schaub, T; Hofmann, P

Year

2016

Journal

ACS Catalysis
ISSN: 2155-5435

Volume

Issue

Page Numbers

2802-2810

DOI

10.1021/acscatal.6b00189

Web of Science Id

WOS:000375894500009

Abstract

A method for the synthesis of the industrially relevant monomers adipic acid, 1,6-hexanediol (HDO), and 1,6-hexanediamine (HMD) via isomerizing hydroformylation of 1,3-butadiene is described. The aldehyde intermediates are protected in situ as acetals to avoid hydrogenation to pentanal. Adipic aldehyde diacetal is obtained in good yields, and the first examples for the conversion toward adipic acid, 1,6-hexanediol, and 1,6-hexanediamine are shown.

Keywords

hydroformylation; 1,3-butadiene; adipic aldehyde; acetal; adipic acid; 1,6-hexanediol; hexamethylenediamine; rhodium