Microwave-Assisted Nickel-Catalyzed Rapid Reductive Coupling of Ethyl 3-iodopropionate to Adipic Acid

3-iodopropionic acid (3-IPA) can be efficiently synthesized from the glycerol derivative glyceric acid (GA), which is a potential biomaterial-based platform molecule. In this report, ethyl 3-iodopropionate was rapidly dimerized to diethyl adipate in a microwave reactor using NiCl 2 ·6H 2 O as a cata...

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Bibliographic Details
Published in:Catalysis letters 2021-08, Vol.151 (8), p.2339-2345
Main Authors: Zhang, Linfeng, Zheng, Jing, Zou, Wenya, Shu, Yongqi, Yang, Weiran
Format: Article
Language:English
Subjects:
Acids
Adipic acid
Biological products
Biomedical materials
Catalysis
Catalysts
Chemistry
Chemistry and Materials Science
Coupling
Glycerin
Glycerol
Halides
Industrial Chemistry/Chemical Engineering
Nylon
Organometallic Chemistry
Physical Chemistry
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Summary:3-iodopropionic acid (3-IPA) can be efficiently synthesized from the glycerol derivative glyceric acid (GA), which is a potential biomaterial-based platform molecule. In this report, ethyl 3-iodopropionate was rapidly dimerized to diethyl adipate in a microwave reactor using NiCl 2 ·6H 2 O as a catalyst, co-catalyzed by Mn and the 1, 10-Phenanthroline monohydrate ligand. Under the optimum reaction conditions, diethyl adipate can be obtained with 84% yield at 90 °C in just 5 min. Diethyl adipate was hydrolyzed to obtain the adipic acid (AA) in 89% yield with an acid catalyst. AA is an important chemical and a monomer for producing a wide range of high-performance polymeric substances. This rapid coupling method is also applicable to other alkyl halides. Graphic Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-020-03496-2