Nylon Intermediates from Bio‐Based Levulinic Acid

Use of ZrO2/SiO2 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 hydrofo...

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Vydáno v:Angewandte Chemie International Edition Ročník 58; číslo 11; s. 3486 - 3490
Hlavní autoři: Marckwordt, Annemarie, El Ouahabi, Fatima, Amani, Hadis, Tin, Sergey, Kalevaru, Narayana V., Kamer, Paul C. J., Wohlrab, Sebastian, de Vries, Johannes G.
Médium: Journal Article
Jazyk:angličtina
Vydáno: Germany Wiley Subscription Services, Inc 11.03.2019
Vydání:International ed. in English
Témata:
Amination
biomass
Caprolactam
heterogeneous catalysis
homogeneous catalysis
Intermediates
Isomers
Levulinic acid
Nylon
rhodium
Selectivity
Silicon dioxide
Vapor phases
Zirconium dioxide
biomass
heterogeneous catalysis
homogeneous catalysis
nylon
rhodium
ISSN:1433-7851, 1521-3773, 1521-3773
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Abstract Use of ZrO2/SiO2 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. Green nylon: Use of 25 % ZrO2/SiO2 as catalyst allows the gas‐phase ring‐opening of bio‐based γ‐valerolactone with methanol to a mixture of methyl pentenoates containing 81 % of the 4‐isomer, which could be selectively hydroformylated from the mixture to methyl 5‐formyl‐valerate, an intermediate for ϵ‐caprolactam. The remaining isomers were converted into dimethyl adipate.
AbstractList Use of ZrO2 /SiO2 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.Use of ZrO2 /SiO2 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.
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.
Use of ZrO2/SiO2 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. Green nylon: Use of 25 % ZrO2/SiO2 as catalyst allows the gas‐phase ring‐opening of bio‐based γ‐valerolactone with methanol to a mixture of methyl pentenoates containing 81 % of the 4‐isomer, which could be selectively hydroformylated from the mixture to methyl 5‐formyl‐valerate, an intermediate for ϵ‐caprolactam. The remaining isomers were converted into dimethyl adipate.
Use of ZrO2/SiO2 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.
Use of ZrO /SiO 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.
Author Amani, Hadis
El Ouahabi, Fatima
Kamer, Paul C. J.
Kalevaru, Narayana V.
Wohlrab, Sebastian
de Vries, Johannes G.
Tin, Sergey
Marckwordt, Annemarie
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Issue 11
Keywords biomass
heterogeneous catalysis
homogeneous catalysis
nylon
rhodium
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Snippet Use of ZrO2/SiO2 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‐,...
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‐,...
Use of ZrO /SiO 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...
Use of ZrO2 /SiO2 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-,...
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StartPage 3486
SubjectTerms Amination
biomass
Caprolactam
heterogeneous catalysis
homogeneous catalysis
Intermediates
Isomers
Levulinic acid
Nylon
rhodium
Selectivity
Silicon dioxide
Vapor phases
Zirconium dioxide
Title Nylon Intermediates from Bio‐Based Levulinic Acid
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201812954
https://www.ncbi.nlm.nih.gov/pubmed/30650227
https://www.proquest.com/docview/2187595898
https://www.proquest.com/docview/2179400861
Volume 58
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