Cobalt-catalyzed synthesis of ε-caprolactam and nylon-6 from aminopentene and carbon monoxide

Shengsheng Liu; Ayusman Sen; Rudy Parton

doi:10.1016/j.molcata.2003.09.011

Cobalt-catalyzed synthesis of ε-caprolactam and nylon-6 from aminopentene and carbon monoxide

Shengsheng Liu, Ayusman Sen, Rudy Parton

Research output: Contribution to journal › Article

4 Scopus citations

Abstract

ε-Caprolactam and nylon-6 oligomers were synthesized from 4-pentene-1-amine and/or 3-pentene-1-amine and carbon monoxide using Co ₂(CO)₈ as catalyst. The results show that the volatile fraction of the product mixture is composed of ε-caprolactam, 3-methyl-2-piperidinone and 3-ethyl-2-pyrrolidinone, while the solid residue mainly consists of nylon-6 oligomers. The addition of excess PEt₃ as ligand can significantly improve the regioselectivity to ε-caprolactam. Using 3-pentene-1-amine as starting material leads to the same results as 4-pentene-1-amine due to rapid C=C bond isomerization.

Original language	English (US)
Pages (from-to)	69-77
Number of pages	9
Journal	Journal of Molecular Catalysis A: Chemical
Volume	210
Issue number	1-2
DOIs	https://doi.org/10.1016/j.molcata.2003.09.011
State	Published - Mar 1 2004

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All Science Journal Classification (ASJC) codes

Catalysis
Process Chemistry and Technology
Physical and Theoretical Chemistry

Cite this

Liu, S., Sen, A., & Parton, R. (2004). Cobalt-catalyzed synthesis of ε-caprolactam and nylon-6 from aminopentene and carbon monoxide. Journal of Molecular Catalysis A: Chemical, 210(1-2), 69-77. https://doi.org/10.1016/j.molcata.2003.09.011

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abstract = "ε-Caprolactam and nylon-6 oligomers were synthesized from 4-pentene-1-amine and/or 3-pentene-1-amine and carbon monoxide using Co 2(CO)8 as catalyst. The results show that the volatile fraction of the product mixture is composed of ε-caprolactam, 3-methyl-2-piperidinone and 3-ethyl-2-pyrrolidinone, while the solid residue mainly consists of nylon-6 oligomers. The addition of excess PEt3 as ligand can significantly improve the regioselectivity to ε-caprolactam. Using 3-pentene-1-amine as starting material leads to the same results as 4-pentene-1-amine due to rapid C=C bond isomerization.",

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N2 - ε-Caprolactam and nylon-6 oligomers were synthesized from 4-pentene-1-amine and/or 3-pentene-1-amine and carbon monoxide using Co 2(CO)8 as catalyst. The results show that the volatile fraction of the product mixture is composed of ε-caprolactam, 3-methyl-2-piperidinone and 3-ethyl-2-pyrrolidinone, while the solid residue mainly consists of nylon-6 oligomers. The addition of excess PEt3 as ligand can significantly improve the regioselectivity to ε-caprolactam. Using 3-pentene-1-amine as starting material leads to the same results as 4-pentene-1-amine due to rapid C=C bond isomerization.

AB - ε-Caprolactam and nylon-6 oligomers were synthesized from 4-pentene-1-amine and/or 3-pentene-1-amine and carbon monoxide using Co 2(CO)8 as catalyst. The results show that the volatile fraction of the product mixture is composed of ε-caprolactam, 3-methyl-2-piperidinone and 3-ethyl-2-pyrrolidinone, while the solid residue mainly consists of nylon-6 oligomers. The addition of excess PEt3 as ligand can significantly improve the regioselectivity to ε-caprolactam. Using 3-pentene-1-amine as starting material leads to the same results as 4-pentene-1-amine due to rapid C=C bond isomerization.

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10.1016/j.molcata.2003.09.011