Synthesis of 1,4‐Cyclohexanedimethanol, 1,4‐Cyclohexanedicarboxylic Acid and 1,2‐Cyclohexanedicarboxylates from Formaldehyde, Crotonaldehyde and Acrylate/Fumarate | Zendy

Hu Yancheng | Zendy; Zhao Zhitong | Zendy; Liu Yanting | Zendy; Li Guangyi | Zendy; Wang Aiqin | Zendy; Cong Yu | Zendy; Zhang Tao | Zendy; Wang Feng | Zendy; Li Ning | Zendy

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Synthesis of 1,4‐Cyclohexanedimethanol, 1,4‐Cyclohexanedicarboxylic Acid and 1,2‐Cyclohexanedicarboxylates from Formaldehyde, Crotonaldehyde and Acrylate/Fumarate

Author(s) -

Hu Yancheng,

Zhao Zhitong,

Liu Yanting,

Li Guangyi,

Wang Aiqin,

Cong Yu,

Zhang Tao,

Wang Feng,

Li Ning

Publication year - 2018

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201801287

Subject(s) - crotonaldehyde , acrylate , formaldehyde , chemistry , organic chemistry , hydrolysis , catalysis , polyester , polymer chemistry , monomer , methyl acrylate , polymer

Valuable polyester monomers and plasticizers—1,4‐cyclohexanedimethanol (CHDM), 1,4‐cyclohexanedicarboxylic acid (CHDA), and 1,2‐cyclohexanedicarboxylates—have been prepared by a new strategy. The synthetic processes involve a proline‐catalyzed formal [3+1+2] cycloaddition of formaldehyde, crotonaldehyde, and acrylate (or fumarate). CHDM is produced after a subsequent hydrogenation step over a commercially available Cu/Zn/Al catalyst and a one‐pot hydrogenation/oxidation/hydrolysis process yields CHDA, whereas 1,2‐cyclohexanedicarboxylate is obtained by a Pd/C‐catalyzed tandem decarbonylation/hydrogenation step.

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