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Nylon Intermediates from Bio‐Based Levulinic Acid
Author(s) -
Marckwordt Annemarie,
El Ouahabi Fatima,
Amani Hadis,
Tin Sergey,
Kalevaru Narayana V.,
Kamer Paul C. J.,
Wohlrab Sebastian,
de Vries Johannes G.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812954
Subject(s) - levulinic acid , selectivity , chemistry , adipate , yield (engineering) , methanol , organic chemistry , isobutyraldehyde , catalysis , caprolactam , reductive amination , hydroformylation , ring (chemistry) , polymer chemistry , rhodium , materials science , metallurgy
Use of ZrO 2 /SiO 2 as a solid acid catalyst in the ring‐opening of biobased γ‐valerolactone with methanol in the gas phase leads to mixtures of methyl 2‐, 3‐, and 4‐pentenoate (MP) in over 95 % selectivity, containing a surprising 81 % of M4P. This process allows the application of a selective hydroformylation to this mixture to convert M4P into methyl 5‐formyl‐valerate (M5FV) with 90 % selectivity. The other isomers remain unreacted. Reductive amination of M5FV and ring‐closure to ϵ ‐caprolactam in excellent yield had been reported before. The remaining mixture of 2‐ and 3‐MP was subjected to an isomerising methoxycarbonylation to dimethyl adipate in 91 % yield.
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